Everyday Decisions: Getting Started with Working for Yourself


Anna wrote in with a common question: how to get started working on your own?

I hear these questions a lot, and they come in all shapes and sizes. Despite the variations, most of them have a common theme. Here’s how Anna put it in her message, which I’m sharing with her permission:

I was recently laid off after working in a middle management position for the past four years. The layoff was sad, but not completely unexpected. The company has been losing money, and while I’d like to think I was irreplaceable, I know the truth is that they simply had to eliminate some positions.

My job was tolerable—I didn’t love it and didn’t hate it. I’m not opposed to going back into the workplace, but the job search is difficult. Many people are looking for work in my field, and some of them are much more experienced than me. I was making a good salary and might have to take a lower one if I was actually able to find a new job.

Besides, what I really want to do is work for myself. I want to find a way to create some kind of small business that pays the bills. I’m not trying to get rich, but I do like the idea of establishing my own security. I don’t know where to start, however. There are lots of things I’m excited about, from writing to making crafts to helping people with their taxes (I know, that’s weird), but I have no clue how to “monetize” these things.

I have a college degree in Psychology. I don’t have any debt except for a student loan that is low-interest and can be deferred for a while. I’m a fast learner and can afford to spend a few months without income while I’m starting up, but not much longer. What should I do?

I’ll share my advice to Anna in a forthcoming post … but first I’m wondering, what would you suggest?

What are the first things she should do to begin creating more self-reliance? Feel free to share your ideas in the comments.

Keep your advice as specific and helpful as possible, and remember: it’s not just Anna who wants to solve this for herself. LOTS of other people are thinking about the same things and looking for ideas.


Update: Thanks for the great input. We’ll announce the winner in a follow-up post within the next week.

*Free prize! Our biased judges will choose one answer from the comments and award a $50 gift certificate to All answers must be in by Wednesday at 9am PST.

Image: Matthew

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  • Jenifer Payne says:

    The first step is very simple, pick something. How to pick? Evaluate the many skills you have and pick one that you yourself could use, were you to not already possess that skill. Once you have picked something, test your idea. Depending on whether its a product or service, there are many ways to find out if your idea is marketable. Once you have a product or service that you truly believe is marketable, establish yourself as an expert and get your idea, product, service, etc out there and available to the general public. After that it’s about management and marketing, (make yourself and expert on these too), if you do these things right, you can’t fail, only learn.

  • Jane Rutherford says:

    There are many venues where you can actually turn your talents into income. If you’re into crafts, I would suggest (it’s a huge and wonderful place). But no maytter what niche and what business you decide on, you should get a website (one with a blog). It will make use of one of your passions – writing. List all the things you’re passionate about and brainstorm 20 blog topics about each of those things. That’s how I found my niche, the topic you’re most passionate about will produce a lot of ideas.

    Once you have a website, get on social media and start meeting people.

    Google other blogs/websites in your niche. Start getting involved with other people in your niche (“get established as an expert”).

    But most importantly: believe in yourself. Believe that you can make it and you can achieve your goals. Experiment with strategies other people are talking about, try out new things and don’t be afraid to not get everything the first time you try it.

  • Erika Giulianini says:

    Hi Anna. While I was reading your message I was thinking “Damn! What’s happening? The entire world is falling apart! There’s no place left where one can feel secure”.
    I’m going through the same mess, I haven’t lost my job yet, but it’s just a matter of months, the company already told us so.
    So, in these months I’m trying to figure out what really are my aspirations.
    I’ve been a creative designer in a huge company for ten yrs and now I find myself worn out by exhausting working hrs, expectations, burocracy an finally rejection.
    I don’t know if I’m approaching this situation right, but I’m really going back with my memories trying to find what really makes me happy.
    I’m checking out what other free lances do, how they sell themselves, how the tax system works…but I think the most important think should be figuring out what kind of work could make you wake up in the morning with exitement.
    I’m still processing this part though, I look farward to read all the comments to this.
    Good luck from Italy.
    A big hug

  • Jet says:

    Everyone has a weakness. Figure out your weakness–and make sure you have a way to compensate for it. In my wedding photography business, I did a good job in marketing and sales and had all the work I could handle. What I was NOT good at was paperwork and accounting–and believe me, there is plenty of it, even in the smallest business.

    The first thing I should have done was hire a good accountant and bookeeper. BTW, there is a very good book called Small Time Operator (available on Amazon) that can help with this.

    Good Luck!!!!!

  • Marvin says:


    Kudos to you for the courage to pose this question. So glad to be able to help. Here are some possible actions to take. I hope they will help you in your journey to self-employment.

    1. Baseline your Finance – cut non-essential expenses immediately (e.g. TV, DVD rentals, gym memberships, daily lattes, etc.) You can add them later, but right now priority is on giving yourself more time to get your business started.
    2. Self-Reflection – What do most of your friends and family come to you for advice on? What are you most known for outside of your occupation? Most likely this is a passion of yours.
    3. Market Research – Are others monetizing your passion? I see you are into crafts and also helping people. Do you have the skill to teach crafts? If your forte is the crafts themselves, check Etsy to see if there is a market for what you are creating.
    4. Test – Put up a simple page that has some of your crafts for sale. A different page for selling craft-making instruction. Use analytics to see which has more traction.
    5. Act – Seek out others who are also selling crafts or related services. Find out how they got started. Keep learning. Try things out. Keep motivated by networking with other entrepreneurs and feeding your mind with information to keep you moving.
    6. Rest – Every week, give yourself a rest day. You need to re-energize so you’ll have the stamina to keep moving. Also, down time allows your mind to wander and new ideas and insights find their way onto your plate.

  • Matthew Thompson says:

    Considering her passions, I think Anna really has a lot to work with. Specifically, something for her to consider would be to explore the idea of selling her crafts on An (older) article to get her started comes from another valuable entrepreneurial site, Her love for writing will obviously help with a blog where she can talk about her process of crafting, techniques, tips, inspirations, etc. Or the blog can talk about the same for taxes and she can generate income through affiliate links for TurboTax. I would think that her degree in psychology would lend itself to helping her relate easier to her readers/customer base. Finally, spread the word through social media.

    Lessons from this for anyone else looking for more freedom:
    -Identify your passions
    -Research how others have put those passions to use for themselves
    -Blog about the experience, what you know AND what you learn
    -Monetize the blog through affiliate links, ads, linking to a personal store showcasing your work, etc
    -Use social media to spread the word! It’s FREE advertising!

    And a final lesson to both her and everyone else: DON’T WAIT! Go for it now

  • Josh says:

    I hope both Anna and Chris’ special feline assistant are reading.

    I’ve been working on this too and realized there are multiple paths and opportunities:

    -Freelance in the same field you were previously in. Perhaps your old company still needs your help, just for a few hours/week. Call up old colleagues, vendors, or customers for coffee and ask about their needs. You could also call up jobs you’ve applied for or were rejected from and offer part-time services.

    -Take a look at freelancing for writing or the skills you want.

    -Find the intersection of your interests+skills+audience who wants to pay. Chris’ 279 Days to Overnight Success talks about this. So does Jonathan Mead’s guide which helped me “figure it out.” Once you know this, start building that audience.

    -If you really love tax forms, then temp at H&R Block or for a local accountant, especially this time of year. You need to be careful with this one because of the credentialing requirements.

    Best of luck on your hunt. Keep us up to date on how it’s going.

  • Paul Nash says:

    Congratulations! This is one of the finest moves that you can make.

    Like any journey, it starts with the first step. And then just putting one foot in front of another.

    The simplest/easiest/”best” way is just to get started. Tax season is coming up, contact everyone that you know (friends, family, ex-colleagues, ex-customers, etc) and ask them whether they want or need help with their taxes. Explain that you are recently unemployed, and nominate a price (either hourly or flat rate) that you think is sensible. If you are unsure of what to ask, talk to friends and family first.

    Don’t overcharge, but don’t get suckered into a race to the bottom. If you charge low, no-one will value your service.

    Dress well and act professionally, on the phone and in person. Treat this as if you were working for someone else. Try to keep track of what works and what doesn’t.

    Don’t try to do more than this at first, or plan further than a week ahead, or you’ll get swamped. If the list above is too much, then just do the minimum — get out and talk to everyone you know and offer your various services.

    That’s it.

  • Helena says:

    To pick something to start with, I think Anna should ask herself: “If I had all the money I could wish for, what would I still be happy to do or work with?”

    I also would tell her to take a month (or more if she can afford it) off of thinking about anything and just be, just get to know herself, and to just do whatever makes her happy. This time off is so incredibly important to not only let go of losing her job and all the baggage that goes with it, but start well on the road of making her own decisions of what she should do next ( and not follow what somebody wants her to do as in when you work for somebody)

  • Ali says:

    If you’re not sure how to monetise your skills/what to offer try thinking about it from the other end. Grab a pencil & paper & write or draw whatever comes to mind: what sort of people would you like to work with? What do they do? What are they like? What do they need? What will they be willing to pay for? How can you give them that? Whatever you offer, you’ll only make money if people buy it, so flip things around & think about your customers first. Good luck!

  • Derek says:

    I think *THE MOST* important thing for working for yourself is to earn your first $100 to $500. That means that in the first few weeks, skip:

    – Branding
    – Buying business cards
    – Establishing LLCs
    – Complicated strategies
    – Etc

    Skip everything except things that will generate immediate cash. Why? Because the very first time you make tangible money as a freelancer or solo entrepreneur, it suddenly becomes a lot more real. You’re no longer just experiencing it as a dream or a hope, but you’re actually on track to making it happen.

    So all your attention should be focused on creating or identifying a product or service that you can provide and marketing it. Explore marketing avenues and try at least 3 different ways to get clients.

    I’d also suggest lowering your price by 30% in the beginning. This is just so you can start establishing a client base, build your reptuation, get experience, get testimonials and hit that first $500 goal.

    Specifically for Anna:

    Writing – Check out I’ve made over $30,000 writing, all through the internet. eLance is a good place to start.
    Crafts: Check out

    Cheers 🙂

  • Brad Farris (@blfarris) says:

    I would tell her to seek out some mentors, just 1-2 who are already in the business field she is interested in. She could intern for them for pay or for free, but that experience is going to be invaluable. Is this right for her? Does she enjoy it? This also starts building her network (essential for success).

    Entrepreneurship is more caught than taught, get close to other entrepreneurs.

  • Ruth says:

    I’ve been s/employed for 16 years. I have learned a lot and still continue to do so. I have one employee, with me for 10 years. My main mistake that you could learn from is to NOT try to do everything yourself. I tried doing everything myself to save money, but actually outsourcing a lot of things to those that are more expert in certain fields is a really really good thing. It makes you work smarter and not harder and keeps you better focused on what it is that you are really wanting to do and gives you time to find your niche. So putting the ego aside and not trying to be the ‘jack of all trades’ is a good thing, not matter how many other skills you have. Concentrate on what you know and hone it.

  • Si Hui says:

    First of all, to cut down on all unnecessary expenditure and downscale where she can. Increases the margin for error.

    Secondly, to write down all of the things she would like to do. Then circle those which she has proficient skills at – and if possible, examples to show it. Then cross out those for which there are no demand. Those remaining are viable options.

    The rest, I think, is miscellany: Talk to people who run their own small businesses and avoid the pitfalls, set up a website, work like a self-employed professional daily to become a self-employed professional.

  • Jac says:

    Go into the consulting business, as a tax consultant.

  • Rebecca Kane says:

    What worked for me?

    1) Starting a blog where I just talked about my struggles. It’s amazing how writing about being lost can help you find yourself.
    2) Do the thing that sounds the MOST. FUN. The more fun the better. You can surf for a living. You can sing for a living. Hell, if taxes are fun, you can do that for a living.

    If you get to choose, choose fun. You’re going to be doing that work a lot. Might as well have a blast doing it. 🙂

  • rixturey says:

    Look for a part-time, temp or consulting job in your field so you can keep the cash flow coming in while you establish your client base and, trust me, deal with the slow times when nothing is coming in. Many times those jobs can become clients. It did for me when I was starting my freelance graphic design.

    Also, network with your friends, co-workers, church, gym, relatives, etc. to see if they know anyone who needs your services. Word of mouth is still the best advertising in my book.

  • Amanda says:

    Anna I am so proud of you for looking to build yourself up instead of running to the next job. Think of things you like, organizations you are part of and thing you are intrested in. Then think of something that community is missing that you can give. You mentioned your degree in psyc. Have you overcome a hardship? You could write about it. Or is something like human trafficking or the like bothering you? Write about it. You could also consider doing Self Help DVD and selling them online. Best of luck. If anything start counceling others for side cash. Everyone needs someone to talk to.
    Living Life Crazy and Beautiful
    Amanda Foltz

  • Jennifer Bennett says:

    I would encourage Anna to sit down and write out what she could do to begin making money this very minute, with no further education or overhead costs. What kind of writing could she do that would swiftly bring in cash flow? What kind of crafts has she already done that have had people swooning? Doing what she already knows and (at least somewhat) enjoys right now could give her more freedom and cash for self-discovery and exploration in the near future.
    Good luck, Anna!

  • Keith says:

    In going through the same emotions and questions as Anna a couple years back – it came down to one thing for me!

    I HAD to eliminate FEAR. Fear of failure, fear of not being successful, fear of looking like a lazy bum to your friends and family. Fear will stop us in our tracks of doing anything meaningful. The best advice I would have is to make a decision to go for it and do not look back. You do not have to have all the answers now and you can change your model, your services, etc. once and if you find it necessary.

  • Shari Margolin says:

    I think you have to first figure out something to do – doesn’t have to be the be all end all, but something that you can monetize for now while you play around with other things and figure it out. Then just start telling people you do it. Friends, family, Facebook, etc. You’d be surprised at how many people come out of the woodwork needing what you do or knowing someone who’s buying what you’re selling.

    That was the case with me anyway. I’m a graphic designer, and I started doing freelance on the side when I had a job. Just based on telling people I was available to do it. I got a few clients. Then I was laid off and really spread the word that I was now full-time freelance. That was about a year ago, and about 6 months in, I had to start turning down work b/c I had so much. I also started a dog collar company and do some freelance writing b/c I love that stuff – they certainly don’t pay the bills, but the hope is that eventually they can contribute to them!

    Best of luck!

  • Sandy says:

    Anna, Congratulations on taking the first steps. You’re one step ahead of me : ) I look forward to hearing more of your journey.
    Thanks for sharing.

  • David Delp says:

    Identify 3 or 4 things you feel you must pursue before you die, and make sure every week that your plan includes a step toward those pursuits.

  • Zak says:

    Anna— I don’t have any advice, per se, but just wanted to encourage you. I’m kind of in the same boat, so just know that you’re not alone. Sometimes it helps knowing you’ve got more friends than those you started out with 🙂

  • Krishan says:

    Dear Anna, I can relate to you more than ever. I quit my job and want to begin working on my own. To that end, here are the steps I have taken:

    (1) Meaning, Pleasures and Strengths (based on Tal Ben-Shahar): Write down the things that give you meaning, Write down the things that give you pleasure, and Write down what your strengths are (or, go to UPenn’s Website and take the VIA Strengths Test.) The purpose of this is to give some general guidance

    (2) Create something — anything — and get it in front of a potential customer. If you think you want to help people with their taxes, create brochure. If you want to do arts and crafts, make something and post it on Etsy. If you want to start writing, start a blog on posterous and send it to all your friends via email and ask them subscribe and share it.

    (3) Engage: Talk with your friends, family, old coworkers and talk to them about what you are thinking about. You will have some naysayers, but you will assuredly have some supporters. Eventually something will stick, feel right and the money will follow.

    I hope these thoughts are helpful and it leads to something positive for you and me both! 😉

    All the best,


  • Candice says:

    There’s such good advice in the comments. May I suggest two things NOT to do as you start on the path to self-sufficiency? Don’t pursue an area just because you’re good at it or like doing it, or because other people suggest it. And don’t assume you can’t make money doing what you love just because others have a hard time making it work.

    Instead, sit in absolute silence without distraction for a full hour. No coffee. No water. No cell phone. Ask yourself what you’re most passionate about. What can you delve deeply into, day after day and week after week, without feeling like you’re working?

    I initially made the mistake of going with a hobby/interest that should’ve remained on a the level of a hobby, just because other people saw me as the expert. I wasted a lot of time and effort. Since then, I’ve found ways to make my deepest passion my primary job. I had fallen for the myth that I couldn’t make money at it (writing, esp. fiction writing), but once I decided to reject that myth, so many possibilities opened up.

    Good luck to everyone starting on their new paths!

  • Penelope says:

    Make crafts to sell immediately and post through Facebook. See what the demand is for your products through your personal connections. Then evaluate and move forward…

  • Hugo Gomes says:

    I would say: think in 3 things you would do for free. Or a combination of the 3. Those are the things you should concentrate and monetize it.

  • Gregory says:

    Take a vacation. Go on a small trip to someplace you like, and watch everything — the sky, water, and, especially, what people do.

  • Jennifer Blair says:

    Anna said: “There are lots of things I’m excited about, from writing to making crafts to helping people with their taxes.” She can probably do all 3, which would be a wonderful way to make a living & never get bored. But first, pick the “low-hanging fruit”. What will bring in income fastest? Probably the taxes job. Then crafts. Then writing. When tax season is over, switch to crafts. Write in your spare time, perhaps starting with a blog tracing your journey – since many can relate. Go to and you can create a free website in an afternoon. It’s easy – drag & drop. Join Twitter & find like-minded people by searching for key phrases. Then Tweet about your blog. You can even do teleclasses on Make up small, free eBooks to give away on your website & start building a mailing list. (Then when you write your first book, you’ll already have a built-in following.) Finally, can you *teach* what you already know? Maybe at a local adult ed. class, community center, or business school? And, if possible, join or create a Success Team. (a la Barbara Sher). Read what she says about Idea Parties, too. Best of luck! You can do it!

  • Michelle Ainslie says:

    Here is my two cents worth:

    Garrett LoPorto (author of The Davinci Method) said that the old cliche of do what you love and the money will follow, should actually read, “Share what you love and the money will follow.” It is through the sharing of what you love that value is brought into the world – the doing is only a fraction of the process.
    So I think you should focus not so much about what you’re going to do, but what you’re passionate about and how you can share that with the world.

    “Don’t ask what the world needs.
    Ask what makes you come alive and go do it.
    Because what the world needs is people who have come alive.”
    – Howard Thurman

    You need to figure out how doing what you love can actually help other people. Figure out what your main passion is (is it taxes, writing, crafts or something else entirely?)
    Now, think of how you can use this passion to reach other people and help them solve a problem, or learn something new, etc.

    Next, get committed.
    “Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then providence moves too. A whole stream of events issues from the decision, raising in one’s favour all manner of unforeseen incidents, meetings and material assistance, which no man could have dreamt would have come his way…Whatever you can dream you can, begin it. Boldness has genius, power and magic in it!” – W.H. Murray

    Then, you must simply do the work. Create your own job. Do the work.
    Get an online presence and a following. The future is online, even for crafts. Give away free advice, make people fall in love with you.

    Package your work and your love as far as possible in a digital format so that it can reach a global market.

    And then sell, sell, sell.

    If you do this with all of your heart for the next couple of months you won’t need to look for another job.

  • Anthony Day says:

    Hi Anna,

    I worked for a company for 12 years. Just like you it was a love/hate relationship. Loved the profession, hated the job. Should have worked there for 6 years and not 12. Took voluntary redundancy.

    To start with it was VERY hard. Specially the first 12 months. And with ups and downs it took me 2 years to settle down into a successful position. In fact I couldn’t decide on the best route, so I took both paths: freelance and online business. And after 2 years of starting on my own, both are so successful that I am not able to give up on either of them.

    Keep trying and don’t settle until you find a path that makes sense and makes you happy. 2011 net profit for both businesses was a cool $2 million – DOING SOMETHING I LOVE!

  • John K. Lunde says:

    Sell something. I agree with the comment above that branding, marketing and a whole lot of other things that big companies do don’t matter when you’re first starting out.

    The first goal should be to sell something. In the process of selling your first xx, you’ll discover a lot of other things that matter in selling more than one thing (like how customers perceive your services/pricing/etc.) and will help you no matter what you end up doing.

    Once you’ve done your first sale, complete the sale by delivering the value to your customer/client.

    This is all that really matters to starting your business. Every time you complete the cycle, focus on understanding why the customer bought from you, and what you can do to attract more customers like that one (or different if you didn’t like this one). And every time you have a potential customer say no, spend a moment (but not too long) thinking through why.

    Constantly improve.

  • Heather says:

    The number one piece of advice that I read over and over is to network. Not just when you need something, but to network all the time, constantly. Tell your family and friends about your ideas, get feedback, and share any progress you make. Your friends and family will “promote” your ideas for you and your network will begin to grow. Most business is earned through word of mouth, so get out there and talk to people. Develop your 1-minute “elevator pitch” and start practicing it! Once you find your passion for something, it’ll become contagious!

  • Jarie Bolander says:

    This is a bold move and I applaud you for taking it.

    1) Figure out your lifestyle burn rate. This is important because this is what you need to survive month to month and will frame the next step.

    2) List all the things you know how to do and want to do. Circle the ones that can actually make you money and cover your expenses. Be honest about this because it’s important to be realistic.

    3) Make a list of all the people you know like friends, ex-coworkers, etc. and ask them if they need your services. Don’t be pushy or anything like that, just say “Hey, I’m doing this now. Can I help you with it?”. BTW, it can be for multiple things or you can send different emails to different people (e.g. some might get the tax help while others the marketing help or whatever).

    4) The first skill or service that gets 10 positive responses is the one you should pursue. The rest drop.

    Good luck and keep up posted.

  • Jason Ford says:

    One technique in working for yourself is to start making money off a skill of yours. The idea is pretty straight forward and looks something like this…

    1. Identify skill.
    2. Find people or companies in need of your skill.
    3. Sell said people or companies a solution that utilizes your skill.
    4. Do it again. 🙂

    I’m going to use an example of a gentleman who is doing exactly what you are looking to do that I recently hired. I was in the office and a rather slim buff guy walks by my desk and asks what I am doing here after hours on a Friday. I told him I was making a workout plan because I wanted to get fit. He told me he was studying to be a personal trainer and was looking for his first client. BAM! We have a winner! I hired him on the spot and he got his first client.

    Here is a second example. My fiancee LOVES to cook. Its very strange to me, but I don’t question because I reap some fantastic food from this relationship. 🙂 One day a coworker stops by and asks if she does more than just bake. ‘Hell yeah!’, my fiancee replied. The coworker was grossly overweight and she learned it had a lot to do with the food he ate. She knew the south beach diet and now cooks his food for him.

  • Scott says:

    I think you are asking the wrong question. You should look inside first. Ask the question what makes you come alive. If your not careful you will create just another JOB.
    Figure out your pasions, skills, abilities, personality traits, then find patterns. Use your imagination, dream, set some goals, create an plan of action. Then most importantly ACT (do something).
    Good Luck!

  • Susan McDiarmid says:

    The answers to your question(s) lie inside of you. The first and most important step is to stop and breathe. Focus on the air coming in and out of your nose, throat, ribcage, and lungs. When you are able to sit and be in a place of calm ask yourself these questions. What do I want? Write it all down. Then ask what do I really want and why? And write that down. Because what you really want is a feeling. For example, to feel security, to have fun, to find meaning or purpose.

    Yes, I think you want the money because it pays the bills, but I think you want something more than that, something deeper (tell me where I’m wrong?). When you have to come to the place of feeling what you really want, ask yourself will doing taxes, making crafts, writing, etc… give you the feeling you are looking for? If not, what would? When you get to the place of knowing what really lights your heart on fire then ask “yourself” what is the next best step to take you in that direction? Then wait. It could be a minute, an hour, or a few days, but the answer will come. It could come from your inner voice, a friend may say something, you might see an a on tv, read a magazine… The answer could come from anywhere. Be open to it. And you know it will be the right answer because of the feeling you get inside. You will just know it was meant for you. That is how the universe works. It will always support your deepest desires. Good luck- but you won’t need it 🙂

  • Ron T says:

    Excellent, vital question! And the answer is remarkably easy. DO something. NOW. Today. TRY something. And don’t worry about it! Yes, that’s what I said-Don’t Worry about it. Just do something. There are zillions of us just like you, also in the same situation. We’re not dying. We’re not starving. We’re making it, maybe only barely, but making it. And if the 1st activity doesn’t work, do another.

    Once you have the $$$ coming in, THEN you can worry about business setup, etc. Do something first; if it’s not the best, do something else. There is nothing like desperation to generate tremendous creativity. And don’t think you have to stick to ONE activity only all the time. Life’s not like that.

    I’ve done consulting, writing, and I did some short IT jobs, then taught a class, then did a corporate tax return and am back to some contract IT work. Life’s a variety, don’t waste it on just one thing unless you really, really like just one thing.

    You’ll do good. I’m sure of it. I GUARANTEE it! Why? Because you want to and are smart enough to ask for help. Try some stuff. Enjoy it. Laugh at yourself, your efforts. You’re trying. Have fun with it.

  • Carol says:

    It begins with the Why? Why do you want to run your own business? Running your own business is hard. Some days, REALLY hard. The way to survive the challenges is by knowing why you’re doing it.
    If you’re on the fence about going back to a corporate job than that may be your best choice for the moment. Once you’ve got the bills paid, perhaps you’d consider starting a blog on two of your favorite topics. Having to find interesting things to share will help you decide if you’re motivated enough to pursue that topic/business idea in a more determined way.
    I know this is not what everyone else is telling you to do. But being realistic about the road ahead is important, be sure you pack a solid Why?

  • Dwayne Cossey says:

    There’s alot of great advice on the nuts and bolts of going out on your own, but what helped me when I was faced with a very simular situation/decision was you have to ask yourself, “What is the absolute worst thing that could happen? And can I live with that?” If the answers “yes” then I suggest moving forward, if not, perhaps you need some time to figure out why you couldn’t live with the worst happening. Most the time framing the worst, actually looking at it, we find that it’s really not that bad, and as with most things, temporary.

  • Tricia White says:

    Over the years, I have counseled many businesses from start-up, marketing and growth to exit strategies and (sadly) shut down. Normally the difference between success and failure is a plan. Consider doing the basics…
    1. Identify your passion (product or service)
    2. Is there a need for that product or service? If there is then-write a business plan.
    a. Identify a market profile – WHO will buy your product/service?
    b. Write a market strategy – HOW will I get them to buy the product/service?
    c. Who is my competition and what are they doing?
    d. Where will I be located? Home or Location
    e. Professional Guidance – Do I need a lawyer or accountant?
    f. Start-up costs – What will it cost to start my business?
    g. Fixed costs – What will it cost me every month whether or not I sell my product/service?
    g. Projections – Can you estimate the type of income you can produce?
    h. Cash Flow – Can I make money at this?
    3. Contact your local Small Business Development Center (SBDC) or SCORE. They offer FREE technical business assistance and can further guide you in the process.
    Good Luck!

  • Franci Claudon says:

    Yay Anna!

    My advice comes from my personal experience.

    I have a degree in Finance and a 20+ year in Human Resources. I was head of HR for a mid-sized software company in Silicon Valley when I was set free (aka FIRED) unexpectedly (well, in hindsight I may have actually been asking for it) in Oct 2009.

    I spent almost two years running away from doing what I KNEW I wanted to do – make a living from my art.

    I spent a lot of time, money and energy dancing around my truth while jousting with the should, can’t and other assorted well meaning limiting voices held court in my head.

    While I intentionally don’t say wasted I can recognize that there was opportunity to accelerate my trajectory if I had COMMITTED earlier.

    What whispers to you on the edges of your mind when your first awaken? What scares you the most? What’s your vision that you can’t unsee?

    Get clear and get committed (not to the asylum but to the work).

    If you can hire a great coach do it.

    Follow the bread crumbs that appear on your path. Learn to live in the paradox of questioning everything AND trusting everything.

    Claim what you want, ask for help, share your story. Take credit. Have fun.

  • Sonja says:

    Anna, I am in the same boat. I lose my not so awesome but pays the bills jobs on Feb 29. There is no passion in me to go find another J-O-B. The only passion in me is to help people help themselves and get paid to do it.
    All the comments by everyone are great. They are right. Do what you love and know, do the work, and everything will fall into place.
    Peace and love

  • Sara D Bancroft says:

    From the bottom of my heart; don’t get caught in the “shiny object syndrome” trap.

    All the information you need is available free online. SOS is a psychological phenomenon whereby say you’re struggling, you buy one of those push button magic software products and the money isn’t coming in yet.

    You open another sales email at the start of your workday and you think back (probably unconsciously, in a nanosecond) to the last time you felt good. It was when you pushed that “buy now” button, your spirit full of hope, excitement and a renewed sense of strength. So you push that button again. And again…

    Habits are said to take 30 days to form and hearing over and over when you read list emails and open links how easy it is to make $5K, $6K a day can make one’s brain immune to the reality of large credit card debt.

    A big pitfall is information overload. Set yourself a short time limit to get an overview. Read say “internet marketing for dummies” if there is a 2012 edition for big picture. Then pick one method to learn: stick with implementing that diligently until you are making money.

    Derek’s method is golden if you think you could be susceptible to the above.

  • IPBrian says:

    Follow your heart, but pay your bills.

  • Leanne Regalla says:

    I’ve been in business over 8 years. This is what I’d do if I was in your situation and why.

    1. Start making offers now and get the cash flowing in. Tax season is upon us. Contact everyone you know and let them know that you are available to help with tax return preparation. Price yourself competitively (not super low). You want to get success now and a feel for what it takes to generate income. You also want to protect that small savings cushion. Bootstrap!

    2. Pick up this book – it’s written by a friend. I have no interest in it & it’s not an affiliate link, but I’ve read it and it’s excellent. Exactly what I would do if I was starting from scratch, knowing what I know now. It will help you get a sense of the direction you should go in, your passions, strengths, and how to monetize them. It will also help you pick your top priorities. It’s easy to get distracted and overwhelmed.

    3. Finally (some may disagree)- don’t be afraid to take a part-time job if you need to. Busy people are efficient people. It’s great you have some cash saved up. Get good at generating income, find your sweet spot, and best wishes to you. NOTHING is more rewarding!

  • Gene Krop says:

    What’s missing in your life? What are you looking for that you can’t find? That’s how Restoration Hardware was started. Someone who had a need and couldn’t find the goods they were looking. And it doesn’t have to be goods it can be services too.

    Two things to keep in mind. Attitude is far more important than skills. You can learn anything you need to learn but unless you’re curious, resourceful and resilient, you’re not going anywhere. Look for another job instead. The second thing is that whatever you decide to do how unique will it be? Even in a crowded field there’s room for another hamburger joint (Five Guys), a pizza place, healthy foods and beverages, even coffee if what you’re going to offer is different enough from the rest.

    Have fun and ENJOY the ride.

  • Kay says:

    I agree with some things that have already been said – taking a bit of time to work out what you truly want to do. Ignoring popular myths that you can’t make money out of that passion is important too, because if you approach it in the right way then you can.
    Once you have worked out what it is you are most passionate about, try to ensure that you know what the clients are targeting actually need. Is there a problem they want resolved, a type of item they can’t find anywhere else, etc. Figuring out should be easy enough as often, when your work comes from your passion, the people you are trying to figure out are a lot like you.
    Good luck – hope you love being self employed as much as I do!

  • Adam says:

    One of the best bits of advice I can think of is to remember that life is hard – but it’s supposed to be. So, to quote Steve Pressfield, “shut up and keep humping”. It’s a brilliant thing to pursue your own career on your own terms, but there’s no other way to make it work than to get up every day, work hard, with humility and total commitment.

    Choose to do things which excite you, and in the early weeks, don’t forget to give yourself time off to wander, explore, meet friends and think – without feeling guilty about doing it! 🙂

  • Julie Kucinski says:

    This is quick and dirty but it is gleaned from 2 wild years on my own:

    1. get honest about what you are really, really good at and can do right away or at least very soon — things that people you can find are willing to pay money for.

    2. Make sure it is something you are willing and excited to spend the vast majority of your waking hours doing and supporting — for years.

    3. Ok – that was fun and exciting! Now the unfun part — Before you do anything else– sit down and decide how much money you need to bring in each month. What can you cut out for now?

    4. Get honest about the stuff you are really, really bad at and figure out a plan for how to deal with it.

    5. Go for it

    6 find like-doing friends and allies to share, vent and support — people who have never done it for longer than 1 year don’t totally get it.

    7 correct mistakes and shortcomings as quickly as possible. It’s far harder to hide on the outside.

    Best of luck!!

  • April says:

    Look for non-profits that help people start a business, like the one I work for called MicroEnterprise Resources, Initiatives, and Training (MERIT). We are located in Oregon, but other non-profits of this kind exist in other areas. Also, there are small business development centers in every state in the US. Organizations like these have business advisers and workshops that can help you think through a business idea and create a business plan and more.

    Good Luck

  • Emily Wenstrom says:

    So exciting – this is something I’ve dreamed about too. I’m not there yet, but I’ve started some steps so that I’ll have a platform to work from.

    First, it’s fantastic that Anna has such diverse passions, but I would recommend either choosing one to start with or finding a common ground that they all come together around (for example, I’m a creative writing hobbyist with roots in journalism, almost five years at creative agencies and I’m currently in PR. I’ve made my niche the creative process).

    Then, make your platform & marketing materials. Others have already recommended a website and blog. Amen. I also strongly recommend business cards and an informational marketing kit that works both on paper and digitally.

    From there, I think the only mandatory ingredients are outreach and persistence. Network, network, network. Organize a blog tour. Attend conferences. Cold call companies you think your services could be of value to. You just have to keep doing it.

  • Matt says:

    First and foremost, I would say that if you are not doing what you are passionate about, you will burn out. Of course it has to be something you are good at and something there is a market for, but ultimately, people are best at what they are passionate about.

    “I am not sure what I am really passionate about…” – People ask this a lot too.

    There is an exercise which I’ve found very helpful. I made a video to help people align their life with their own values. If you click on my name, it will take you to the video.

    This was eye opening for me and now I am working on meshing my business and lifestyle together.

    I hope it is helpful 🙂

  • Felice says:

    Well, you should just take the next step.

  • Sara says:

    Sorry that you lost your job, but it sounds like you’re in a good place. You’re not beating yourself up, nor are you bitter and upset, which are all good things.

    You have a ton of interests and skills, but note that some arehobbies and some can be viable businesses that sustain you and lead you to a comfortable and happy life (even if you never become 1% wealthy). Prime example, I enjoy knitting, but not enough to make hats to sell on Etsy for a decent profit. Needless to say, I keep knitting as a hobby.

    I think you should also consider your strengths. What makes you want to get out of bed in the morning? If your strength is math, and doing work in accounting and taxes is rewarding, maybe you can start a blog about all things related to that and offer a tax company. You may even look at volunteer programs that help people do their taxes and maybe you’ll gain some insight on how you can take that passion and combine it with helping others and flip that into a business.

    Sometimes the first part is stepping out into the unknown. My recommendation for you is to think about what you really love doing and proceed in that direction. Good luck!

  • Bradford Glass says:

    What a beautiful opportunity to STOP (do nothing instead of something), and REFLECT (look inside instead of outside). It’s a gift to have the space, even a few months, to discover the natural, innate creative essence you are on the inside. For when you find the authentic “you” — the “who you can’t help yourself being no matter what” — you find a beacon of light inside you that can illuminate your path wherever you go in life. Honoring and trusting that source of guidance, a “job” will find itself. The “coolness factor” here is that it will be “work” you always wanted to do, offering your uniqueness to the world and getting paid for it.

  • GG says:

    Congrats for the first step, I´m very jealous that you are “forced” to get self-employed, hehe. I personally would love – and pay for – someone who combines tax-matters with psychological / counselling skills, as taxes and money are highly emotional and overwhelming things (in my point of view). If you do like to help people with their taxes, you could ask in adult education centers if there´s any need for “psychological” tax seminars (overcome procrastination e.g.), and you could write articles, books and so on about it. I wish you the best from Germany, have fun!

  • Kitty Brown says:

    The first step is recognizing what courage it takes to go it on your own! Congratulations! I know how hard it can be to go against everything you’ve been taught and strike out boldly on your own. Don’t ever forget that! Don’t act like that isn’t a big deal! Always remember that you boldly chose to go against conventional wisdom and do it YOUR way!

    The second step would be to figure out what moves you. What are you passionate about? What makes you feel alive? What do you want to accomplish? Is there someone, something, or a group you would like to help?

    The third step would be to create an action plan, then act on it. Now that you have what you want to do figure out how you’re going to do it, where you’re going to do it, and with what. Consider: How are you going to reach people? What is your budget for this? How much do you need to be bringing in to live comfortably? Who can you learn from? Where are you going to be physically doing this work?

    I hope that helps! Again congratulations on striking out on your own! I wish you the best of luck!

  • robin says:

    get comfortable with money!…….

    add zero’s…they are free

    that is advice that shifted my pattern of ‘just making what i needed for next step’… saw me go from the comfort of a 500 bank balance to 50000….to buying a 500000 business in a very short time

    it was the area i had ‘issues’ in…the ‘following ones passions is the easy part!check where the blocks are inside…the internal messaging re worth/needs/money…….<3 may you be uplifted and fly

  • Linda Gilbert says:

    It looks like you are already on the first step to freedom,

    4 years ago I was in a similar situation, I have always worked (in jobs i didn’t particularly Like ) Just to pay the bills ,I was never very academic and left school young so was always limited in what work i got, but when i desided i had enough and actually believed i could get paid for doing what I loved it was like a breath of fresh air, I am now running a small children’s entertainment company, it is still in it’s infancy but getting better and more lucrative every year.

    When I first had the idea I was suprised at how many people, some of whom I would have considered my closest friends and family thought It was ridiculous and I am so glad now i didn’t listen to the negativity , But my partner and daughter gave me so much encouragment and their belief in me soon made me believe in myself, Now my partner and daughter actually work with me , and I have never been happier.

    I have had some of my scariest, nervous, but most exciting and proudest moments in the last 4 years and i would never look back. Believe it will work for you and don’t let anyone knock your ideas and your bravery.

  • Vicki Madden says:

    Call together several people who know you well, from both work life and personal life. Think of them as the Advisory Board of Your Life. First, have some fun…play Two Truths and a Lie. Then ask them when they have seen you most passionate, in the moment, in flow. What do they think you do best? What are your biggest gifts – in all areas: relationships with people, content knowledge, etc.?

    Then ask them where have they you struggle, what shuts down your best self, what kind of work (either subject area or function) do they think you shouldn’t pursue? Are you best working alone? Or does a group bring out your best self?

    You will learn a lot and it will help you focus your vision.

  • Sharon says:

    1. Estimate your target annual income (living expenses, periodic bills, insurance, car payments, retirement, etc.). Include 2-4 weeks of no income for vacation.

    2. Define your DREAM JOB; the type of work you like to do, the skills and talents you most enjoy using, the environment you’d like to work in, the self-employment characteristics you like most, etc.

    3. List all your business options in order of desire and how much they fit your dream job characteristics.

    3. Research other businesses or jobs in those areas to determine what the going pay rate is for that type of work.

    4. Decide which options you could reasonably earn a living.

    5. Pick one to pursue. Pursuing multiple businesses can be overwhelming and dilute your results. If you like multiple options, how can they be combined into one business? Or pursue others on the side, such as tax preparation during tax season. But, if tax preparation takes time away from your main business, it should bring in at least the same amount of income or be as enjoyable.

    6. Prepare a basic business plan for the selected option. Describing your business in this way can help reinforce your choice or negate it.

    7. Start! Go for it!

  • Brian Storey says:

    Remember, when you are choosing a vocation (whether your own business or when working for someone else) to “Let thy trade be thy sport”. This is paraphrased from some writings by Henry Thoreau. Conversly, your favorite activity will not necessarily be a feasible business, but there is always a balance that works. Choose carefully.

  • Karin Lehmann says:

    What a great opportunity to get going with your own business, especially if this is a dream of yours.

    I would NOT run where the money is first but take your time figuring out what it is you’d enjoy doing in the long run. If you start something just for the money chances are you’ll get stuck doing that and run out of steam a few years down the road. Not fun.

    Find out what brings you alive. Ask yourself what you’d love doing even if you didn’t get paid. Do that.

    Once you are clear on this step, you can start setting up a first project. I’d keep it small at the beginning. That way your business will grow with your experience.

    For example, if you’d like to help people with their taxes, find out who exactly you’d like to work with and what this specific group of people needs. This will help you to tailor a service uniquely to them and start selling it. Listen for feedback so you can adjust your plan.

    There is lots of great advice online about starting your own business and once you narrowed down your service / niche you can start doing research and get input directly related to your field.

    Hope this helps and good luck!

  • Megan Merchant says:

    My advice is NOT to work for yourself, yet.
    Very few people apprentice anymore, but EVERY workplace needs people willing to start at or near the bottom and learn their trade, and one day even take their place. My advice to you is to pick your passion, go where people earn a living doing that job, and ask what education/skills you need just to get in the door. Then GO GET IT! I’m so excited for you!

  • Rachel says:

    I admire Ana’s courage. The best thing she could do for herself is to really have a game plan with what she wants to accomplish with her new found freedom. It can be terrifying to start. Where does she begin?

    The dreaming and wishing is the first step, but what next? For me, when I was starting out, I really need to volunteer or work part-time so I wasn’t spending 20 hours a day worrying about my new business. Plus, varying up the day with activities that you actually want to do is a perfect opportunity to get inspired to do what you love. For example, painters should explore nature. Writers should have diverse experiences and interact with others in order to produce amazing stories. Business people should network and learn from other experts.

    It’s never too late to go for your dreams, but it’s better to start with a plan and a time frame.

  • Duane Brown says:

    I’d recommend Anna pick one things she’s going to secure her income on. From past experience it’s hard for friends/family to refer business to you if you do to many things (taxes, and writing and craft).. they’ll be confused about what business you’re in.

    You can do the others as a passion, however, only one should be your main income. Then start letting your friends, and family know you’re in this business. Start networking with likeminded people within that industry (especially if you’ll do taxes). I’d not ask friends/family if they’ll pay for this service as most will just say yes. You need them to actually buy & put real money in your hand.

    Lastly, I’d look into a small business lawyer & accountant if you plan to setup a company/corporation. Investing in them will provide you with legal & accounting advice you will find valuable & unbiased. They’ll want you to succeed, so you’re around for the long-term. Friends may be able to refer you to one.

  • Daniela says:

    How I would loooove someone to teach me how I could do my taxes and stay joyous, positive and at ease or even EXCITED!

    That is the niche!

    Aren’t taxes the thing most people have instant stomach and head ache just by the sound of it. The word tax probably provokes negative feeling from 99,9% of all the people world wide. And the 0,1 % are probaly working for the IRS.

    Turning fear into power, fuel or anticipation is something that can only happen if we change our thinking. For these big changes we need new tools, metaphors and psychological support. Wouldn’t it be great to spearhead the new ‘tax for fun’ movement?

    So what a great combination, taxes and psychology. But it all depends on your passion of course. That step No 1 we all have to go soulsearching for first. If your passion is more within the craft part, then maybe handmade IRS woodoo dolls are the way to go ; )

    All the best for an exciting journey.

  • Brandon W says:

    There is a lot of good advice already here that I won’t repeat, but something to consider:
    Decide whether you want to be self-employed or if you want to own a business. There is a big difference. Either way can be the right way for individual people. But decide whether you are a solo individual providing a service (like writing, or graphic design, etc.) or whether you are creating a system where a product (or service) is being provided for customers, and you are the one who manages the system.

    I have done both, and I prefer the latter. My business provides a wide range of business services but I personally do none of them. I find clients, manage the work distribution, hire/fire/replace service providers, and make sure my clients’ work gets done correctly, on time, without the trouble of managing everything/everyone. So owning a business doesn’t necessarily mean products. It just means owning a system and managing it.

    But I have a friend who does interactive media design and refuses to hire anyone else to do the work, because he loves being hands-on and doing it himself.

    Either way can succeed, but it should fit what you are best at and how you would like to work.

  • Andrew Robinson says:

    Offer your talent with taxes in the form of shares. A limited number of people can buy in to your DIY tax boutique—as easy as Turbo Tax, but relational and, dare I say, fun.

    You’re on the verge of some of the most rewarding, challenging chapters of life. Congratulations!


  • Emerson says:

    Tons of good advice here. It really depends on your situation. There’s a lot more you can do if you have some money socked away.

    I’ll just add that, when I lost my Hollywood job, my girlfriend at the time sent me a link to this movie, and I recommend it to you.

  • Janelle says:

    Everyone has provided excellent advice; I’ll chime in with a few points:

    Finances – It’s not clear from your message how much you have set aside. You want to make sure you have enough to sustain you while you figure things out. The last thing you want to do is worry about money. Here’s what I would do:
    a. Take on a part-time temp job. Whether it’s H&R Block or a something else, the goal is to stack some cheese.
    b. Set aside at least 6 months of expenses. If you already have this, skip step a.
    c. Downsize. If you rent, move into a smaller place. If you own, rent out a room. Sell what you don’t need and add the proceeds to your emergency fund.

    Study – While you’re working part time, learn the basic skills necessary to make money writing, selling crafts, etc. Check out The Well-Fed Writer from the library.

    Act – Don’t worry about perfection, focus on quality. Help clients who know less than you, then scale up as you learn more. Move beyond fear one step at a time.

    Ready, Fire, Aim – Try several things, then focus in on the one or two that you enjoy and are profitable.

    Listen – Acknowledge & follow the good feelings!

    I sincerely wish you well on your journey.

  • Laura Simms says:

    Working for yourself can be awesome, but it doesn’t sustain you overnight. I would find an enjoyable non-entrepreneurial source of income for starters. Something part-time or a little left-field would be just fine. Something that will give you a paycheck for just showing up. Because once the money gets tight and your basic needs feel threatened, it’s really hard to take the risks/summon the guts required to go out on your own.

    Then I’d invest in a career coach who gets you. Biased? Sure, because I’m a coach. But I’d enter into self-employment with a fairy guide-mother so you get off to a great start with something that you’re well-suited for and that suits your personality, interests, and financial goals.

  • Christine says:

    Since you are currently being driven by some overriding passion of what you want to do, I would say to take the thing you mentioned that would be the easiest to make some money on–and to me, that would be helping people with their taxes—especially right now! In fact, you could probably get a temporary job doing just that, to see if it is something you really wanted to do or not. And you might also be able to make a plan for creating your own business out of it while being employed doing it for someone else. Then , in the meantime, start delving into what you really have juice for. I am an artist & have been doing that for years, sometimes working several jobs to keep myself afloat. The idea of making & selling crafts is nice, but trying to do that without a clear plan of how to proceed and no job to back you up while you figure it out is not the best idea financially. If you have a driving impulse to create, that’s different. But not for the faint of heart Good Luck!

  • patrick says:

    You are deluding yourself. Being self-employed does not necessarily lead to any more ‘security’ than being employed. What leads to security, in any kind of employment, is having scarce skills that other people need/want and are willing to pay for. Since I didn’t hear you mention any of those, I would guess you don’t have them. So my suggestion would be to develop scarce skills that other people need/want- and then the money and security will take care of themselves as long as you are a halfway decent human being.

  • Jen East says:

    Speaking as a student & college instructor, with sidelines as a weaver, artist, designer, & writer — who has been doing all of those things for the last few decades and works with college students of all ages facing much the same choices — I’d say you have great prospects. Most often it’s fear that keeps us from breaking past the procrastination barrier, and since taxes seem to be one of the biggest potential benefits in starting one’s own business and the biggest fear factor, you could easily use your psychology/writing/tax skills immediately to begin a tax-time blog for start-up solopreneurs, and offer your services. I’m sure you can trade those skills for a lot of your own start-up needs as well to save money and start getting word-of-mouth referrals. I’m a graphic artist who desperately needs a tax consultant — want a logo, business ID package, brochure? Let’s trade! I’ve been tying myself to part-time jobs for “security” and keeping business activities at “hobby level” for fear of doing the taxes wrong, which is the most common hold-up I hear from peers and students. You can always pursue the crafts as a sideline and see if that becomes another stream of income too.

  • Amanda says:

    Personally, as a freelance writer, small business owner and entrepreneur (living on a little island at the bottom of the world), I’ve found it very difficult to find book-keepers/tax experts/business advisors etc who understand the special requirements of a creative person in an isolated place (I’ve even had to educate my accountant on new developments in the industry!).

    While I realise that Anna may not have the credentials to operate as a freelance consultant in these areas, she may still be able to provide a valuable service to freelancers and creative small businesses (since she is creatively minded herself) on the business of being creative.

    For example, I’d buy an ebook/subscribe to a newsletter created by someone who delivered all the ‘Inside Secret on the Business of Being Creative’, for example. I’d also potentially hire their consulting services.

    Essentially, Anna could set herself up as a ‘Creative Business Consultant for Creative Small Businesses’. She could use herself as a great case study, promoting her journey (which personalises her services).

  • Brianna says:

    Hi Anna. I’m so sorry you lost your job. I’ve been there, done that. My best advice to you is to just pick something. Do some volunteer work – that might lead to a job. Network as much as you can. Step back from what you did previously and evaluate your hobbies. What can you use to market yourself? Do you have a skill that you can sell?

  • Mary H says:

    I’ve run several of my own businesses and started and run 2 non-profit corporations, too, over the years. However, this advice is not from me, but taken from Farrah Gray, who has a couple of very interesting books. He says, start with thinking about these three questions. 1. What comes easy to you, something that you are good at, that is hard for other people? 2. What would you do, day after day, year after year, without any pay whatsoever (assuming you had the ability to work without pay)..and 3. What can you contribute to the world? What do you want your legacy to be? (I kind of added that last thought. Also, from me…don’t go into debt to do whatever you do….keep a day job for awhile if necessary and ease in…

  • Devon says:

    This is the perfect time of year to cut your teeth in the individual tax prep market! So many people *abhor* taxes, so you’re bound to have potential clients nearby. Do a little homework on setting up your business (entity type, software, certifications, etc.). Even more important, make a plan for what you’d like each of your clients to experience from intro to payment (How can you deliver convenience throughout? Can you throw a personal touch in there to make the experience memorable so they’ll think of you again next year?)

    Then *unashamedly* put the word out to all of your friends and family. Unapologetically and kindly offer to relieve busy people of a headache-waiting-to-happen for a reasonable fee (you could check out HR Block rates and and see if you can learn what the local firms charge to gauge the going rates). Marketing is the biggest challenge while you build up a clientele of course. Brainstorm to get ideas….I would put some kind of sign on my car with my business logo and number to start.

    Do you live near a college? I’m an administrator at a state college where I’m also an accounting grad student. The international postdocs and grad students are constantly asking me for tax advice…if you have a college nearby, see if you can reach out to that community. Trust me – most academics *loathe* paperwork more than anything…taxes are just cruel to them! The international employees are downright desperate for assistance…their visa paperwork is already exhausting. Also, ideals about supporting the local economy tend to resonate with them so they’re relatively keen on alternatives to big businesses/franchises.

    I’ll bet that your first tax season would empower you for your other ideas too, and you can diversify your income stream from there. You’ll have contacts, business savvy, and the only thing that’s holding you back now…confidence! Btw – you’re obviously articulate, discerning, creative and smart so there’s no need for trepidation. When I feel overwhelmed, it always helps me to remember the sage words of my mother – “Give ’em hell!” 🙂

  • Carolynn says:

    I second Derek’s advice to skip the expensive LLCs and branding in the beginning.

    I agree with everyone else hear that you have to identify your target audience, but I want to take this a step further: you have to go out and meet them. Offer talks and workshops, attend business breakfasts and luncheons through BNI, Meetup and Franklin Covey. If you got 3 new clients a week as a result of this strategy, you got the beginnings of a business there, especially if they’re repeat clients! If you have something people want, consider it a great service to let the world know what you do. I am always excited when I find something or someone who can make tax-time simpler for me!

  • hilory says:

    Interesting responses. I think that the basics have been covered, but I just wanted to ask a simple question. Since there are so many who desire to be self-employed, why not have a forum where those with similar interests and complementary skills could join forces? We all know that doing it all is not effective. For anna, perhaps collaborating on a business with another interested in crafts-Anna could handle bookkeeping and blogging, perhaps her partner could handle social media and face-to-face networking. Both could work on items to sell. This is just an example – I just wonder why more people don’t collaborate to maximize success.

  • Mary says:

    It’s terrific that you’re not fighting much debt. You don’t sound desperate. And you have time to experiment.

    I’d recommend as a first step writing for content mills online. There are a multitude of them, from Demand Studios to Textbroker to Wise Geek. This is putting your toes in the water.

    You’ll get to pick from a variety of topics, write a set amount of words, and get it in on deadline. And you get paid! Not much, like $10 or so.

    You’re being paid to learn how to write for the web. You’ll become familiar with keywords, deadlines, writing concisely. It’s great training.

    You don’t need to stay there long. Just get a feel for the different types of writing for the web.

    Then pick a niche, like helping people with their taxes! What a great service, and truly in demand. Blog about how to make it a less emotionally demanding experience (this is no joke, I speak from personal experience!) Blog about how to organize the information, about what to look for in an accountant. About all the things you’re comfortable with and the rest of us aren’t.

    Write an ebook and sell it to your list. The possibilities are endless.

    Good luck!

  • Michael says:

    There’s a lot of terrific suggestions. Somewhat similar to the previous post from Scott, I start by going inward. The simplest and most direct access to doing this in the realm of work/career/craft is to ask yourself, “What would I do if there were no rules?”

    Typically, I come up with a decent answer out of the gate but then to get deeper I ask a follow up question at least once or twice, “If I had already accomplished that (the answer to the first question) then what I would I do if there were no rules?”

    By the time I get to the third answer, I’m at the heart of what most would inspire to leap out on my own.

    Plenty of folks above and elsewhere write about what to do next, but having an authentic inner flame is what has sourced my transition on three occasions.

    Best of luck!

  • Peter Cresswell says:

    It does not feel like it yet but the day you were let go was the greatest day of your life! You are now one very difficult step closer to being the happiest you have ever been in your life.

    To get started, do one simple thing. Right NOW!

    Cancel your cable subscription.

    That’s it.

    Your TV is a time wasting, fear inducing, consumerism pushing box. You didn’t need it before and now that you are taking this leap of faith into self employment, you certainly DON’T need it now.

    Get rid of it.

  • Audrey Reynolds says:

    Great advice on here – I agree with “just start”, “test/experiment”, “don’t try to do everything yourself” and “rest”.

    A few more things I learned during my recent layoff:

    Don’t dismiss creating your first business based on what you did in your last job. I see a lot of advice about dreaming and it’s important to define your dreams and vision. But it can be overwhelming to create a client base from scratch when you feel $/time pressure. There is nothing wrong with generating quick income using connections/skills you already have. You are not selling out your dreams, you are giving yourself the experience of SUCCESS and COMPLETION. You can then expand into whatever “your thing” is. Speaking of Your Thing, check out Tanya Geisler’s Thing Finding Thursday series.

    If you collect unemployment, containerize the job search is as much as possible. 1x/week, set a timer and knock out your apps. Do the bare minimum and forget it. And don’t feel bad – your job is CREATING your own. Find large companies with a lot of jobs, create a profile & apply to several jobs at once.

    Do mindset work. I am still early in my entrepreneurial journey but I’ve found a lot of worthiness stuff has come up.

  • Ian Robinson says:

    Start with a blog and write everyday about what you love.

    (Sometimes the simplest advice is the best. You have an awesome opportunity. Do it!)

  • Dan says:

    Do it! I was laid off 3 years ago just at the start of this recession, and in an industry at the middle of it: real estate. At first i found temporary jobs related to what i was doing. After 2 years of this i realized what i was doing was “consulting” and that i liked the lifestyle. Now i have a few clients, paying the bills, and building MY business. While it is scary to go out on your own, and I am still anxious, what really scares me is having a full time job where all my income is coming from one source. Now that’s scary! Best of luck!

  • Willem says:

    Being self-employed for nearly two years, I’d suggest:

    Start now! Don’t wait for your perfect business idea. Get started now with whatever you’ve got on your hands and like doing. You can change course when already afloat if necessary.

    Make sure you can pay yourself and your bills. Being your own boss is really great. Just make sure your business generates enough income to pay 1) yourself, 2) your bills and 3) perhaps even make some profit.

  • Helen says:

    I have just moved to South Africa from the UK to be with my partner and I decided to pool all of my skills and start my own online business. I had some savings (about 6 months worth) so I thought I’d be OK, up and running, starting to bring in a little money, even if only a little by now. One thing I did not count on is that everything takes AGES. It may just be South African red tape which doesn’t help but it has taken me 6 months and I haven’t even launched yet.

    I am not saying this will happen to you however the biggest piece of advice I would give you is to get a side job. Not something that will take much brain power or energy away from your business, or much of your time and something that you won’t end up getting “stuck” in. Maybe waitressing or helping people with their taxes freelance like you said. Just something to take the edge off worrying about money and enough to give your business a mini cash injection when needed. I wish I had done this 6 months ago while I have been trying to get set up as now I am left in a position where I am just about to launch but I have run out of money and so I need to get a job. So just don’t give up but remember cash is king!

  • Thomas Carney says:

    I would not jump directly into running my own business. I would first find a job that will cover the bills. Then I work on cutting the bills down. At the same time I would start freelancing on the side. The target would be to earn a modest sum of money a month. Then, over time, I’d transition into working full time for my own business.

    And yes, I am copying Ramit Sethi’s Earn1k approach!

  • Roger Ellman says:

    The quality of advice here is so good, and fortunately the big themes are repeated (quite rightly!).

    I won’t duplicate what has already been said, so I wish you well Anna, and everyone who has written offering such valuable, practical and usable advice.

    Live long and prosper!

  • Matt Staples says:

    Mine is a simple piece of advice; find and follow the passions of your life that you take most for granted. Often when a person is umming and arhhing over what particular avenue of business to follow the thing that they’ll love doing the most is usually staring them right in the face.

    When people want to start in business they usually fall into the mindset that the business venture they want to follow is something special or unique and they wait for a Batman-like epithany to come to them before doing anything (I shall become… A BAT… psychologist).

    Don’t wait for this. You know the things you like. Follow the stuff you find yourself doing that you don’t even realise you’re spending time on them. For me it was comics. I was reading and drawing so much that i didn’t really click on the fact that i was devoting huge portions of my day to them. As soon as i acknowledged this focusing them into a business was so much easier.

    Hope that helps.

  • Martin Pigg says:

    find your Passion. pursue it with Intention. and live with Gratitude and Grace.

  • Travis Hellstrom says:

    Leave the country.

    All of the above suggestions are wonderful, I just didn’t see anyone mention this one. You don’t have to leave the country of course, it just sounds like this could be a good time for you if you’ve ever considered it.

    Joining the Peace Corps and living in Mongolia has opened my eyes to how affordable it can be to “follow your passions” in another country, at least at first. You can always come back home anytime.

    It can be hard to leave a good job to travel or live abroad, but if you aren’t tied down to a job currently this could be a great time. All the things you mentioned that you enjoy can be done anywhere (even taxes with a computer and Skype), so going international seems like it could be a fun option for you.

    Good luck Anna!

  • Gustav, the Modern Nomad says:

    It is not easy. It takes time. And therefore, the most important thing you can do for yourself is buy yourself more time by reducing your costs! Seriously. This equation has two sides, and one is a lot easier to affect than the other.

  • John Liddle says:

    Good luck Anna. It’s clear that there are a lot of people wishing you well and wanting you to succeed. Just the sort of friends to have!

    The only thing I’d add to the good advice you’re already received is the value of your feelings as a guide to action. When I’ve felt something has been right it has always turned out well, though not necessarily in the way I was expecting. Equally, when I’ve overruled my feelings and gone ahead with something that didn’t feel right it always led to problems.

    It’s good to know that you’ve got an internal guidance system when you’re setting out into unfamiliar teritory.

  • Holly Em says:

    It will take more than just a few months (the time she has) for her to get started. She will need to have a short-term game plan that will tie her over (income-wise) until her small business idea is developed and starting to earn decent cash. It will be a lot of hard work, especially in the initial period when she is doing that one thing that pays the bills whilst at the same time learning, developing and setting up her small business. It’s definitely worth a go, as you learn so, so much more when you go it on your own. However her expectations need to be managed so that she is prepared for he amount of effort it will take. With that said, most of the ‘work’ she does for her small business will not feel like work, as it will be for herself:-)

  • Gary says:

    I would read Cal Newports blog

  • Brian Storey says:

    Your friends and advisors will tend to tell you that they “love the idea”. Often they are not being honest because they want to support you and your enthusiasm. It is easier and more comfortable for them to agree with your idea. Get some professional help in determining the path, or, in this case, your ideas can be judged by people who care about your future, but don’t know you. We can be honest with you with no fear of offending.

  • Josie says:

    1. Answer two questions: what do you want, and what do you have to give? Use as much rich detail as possible. Get more info by doing self-discovery exercises.

    2. Use this info to choose what you want to sell. Consider combining your skills to form a unique new business, such as tax prep for other full-time crafters/writers, or writing about how to create fictional characters with realistic psychological profiles.

    3. Research all resources available to you. Are there programs in your area to assist new small businesses? Grants for specific education? Do you know anyone in a similar business who would be willing to give or barter advice?

    4. Find places to sell your product or service. This might be a craft site like, or Articles can be posted on a pay-per-page-view site like or sold at If you have a collection of articles, they could be sold together as an eBook.

    5. Set a clear goal. Start with something generic (I want to make a full-time living) and then fill in the details to create a plan.

    6. Launch! One of the fastest ways to learn is to try something and get feedback.

  • Amber says:

    Start with who you are. Think about who you are, and what really matters to you. and what kind of life you want to build. Start with one thing, then build up to the next.

    Good luck!

  • Lorrie Kueffer says:

    Chris, THANKS for the opporunity to comment. Lots of good suggestions above. My husband and I are leaving our jobs to have the freedom and independence we want, and transitioning into new lines of income. I won’t repeat what I’ve read so many people say, all very good advice. I would also like to add that there are some wonderful network marketing opportunities that are worth looking into and are very helpful to others. I have become a Juice Plus rep, a natural transition for me becoming vegan for the last several years. I love the product and the company, and it’s value to people’s health. One other thing I’d like to mention is to simplify, simplify, simplify…the fewer expenses you have, the easier you can live financially, and still live a very abundant fabulous life.

  • michael says:

    Anna, do not panic, keep calm. Breathe and Smile. Make somebody else smile. Write out a gratitude list…….. EVERYTHING you are Thankful for. From this foundation you will be inspired. Best Wishes for the future.

  • Sylvia says:

    My suggestion is to find an inspiring mentor who understands how to guide you in discovering what totally makes your spirit yell, “Hell YES!”

    My motivational muse is Amber Rae. Like Anna, I had many passions I wanted to explore. I didn’t know where to begin. Working with someone who fully grasps how to unleash your full potential and give YOUR dreams direction is liberating! I’ve gained new perspective on my vision and am uncovering emotional blocks that I wasn’t even aware were guiding my decisions.

    I followed Chris’ blog for a 1 1/2 years before I finally took the leap. 4 months ago I packed up whatever I could fit into my Nissan Juke to leave my blingy South Florida life behind and move to Boulder – the scariest, most thrilling decision I’ve ever made.

    Months of personal reflection had awoken me to the fact that everything I called “Family” and “Home” no longer fit me. If I was going to be totally honest with myself, it never had. And so, I decided to stop living life on the surface and dive in.

    There have certainly been tough moments since “the big jump” but my heart has never been happier. Today, I am living my life on MY terms. And it FREAKIN’ ROCKS! 🙂

  • Manan says:

    Do what Steve Jobs did..find something you fall in love with,become passionate about it and follow it through and through…In life,you can focus on one thing at a try anything that you find interesting and worth spending more time on …it has to be trial and error.How can you expext to stumble across your passion in first go(very few have found).. And then,there has to be cannot sell people what is already out there in the world.. It has to be different.And that usually happens when you have spend some time researching about it..but if you love your job,you end up inventing new stuffs thats exciting.. Its like study hacks motto:be so good at something that its too hard for the world to ignore.And I do not understand..if you want money,never say I dont want to be that rich..Have the right attitude.Listen to think and grow rich by Napoleon Hill audiobok everyday..spend fifteen to twenty minutes at night thinking about ideas and ask yourself how am I to spend the next three months..try getting as many answers as possible..I ll tell you something..This Chris is writing blog because he know the trick of his trade..he is focussed on travelling for a couple of years..Now what did he do first?travel or create a blog to attract like minded people?He first asked himself what he really wanted to do..he travelled.Because of his passion for travelling,now he earns a living out of it..its what he chose for himseldlater things connected and money poured in…so mOral:you cannot cOnnect the dots now..but if you think ten or twenty years from now,then life will make more sense…

  • MelodyO says:

    Here’s my advice coming from someone who has been successfully self employed for 15 years and now has a heart-shaped cube of ice where my heart used to be. :0P

    I know people are going to tell you to follow your heart. I’m really, really not. Anybody can take a hobby and try to make a business out of it. Very few can make a living at it. It can be done, but your passion for that hobby better be white-hot, because you’re going to have to work harder and longer than everybody else to make a go of it. Maybe do the tax return thing AND the craft thing, as multiple income streams are always of the good. Having said that, here’s my advice after you decide what you’re going to do:

    – The internet is your friend, plus a cheap date. Use it to sell, and use it to network. Network your ass off! You’ll be assless, but you won’t be sorry.

    – If you make crafts, don’t make the crafts you think of while you’re in the shower. Figure out what sells well already and make your own version of that (don’t steal the ideas, steal the categories). Don’t reinvent the wheel, especially if it’s crocheted.

    – Don’t give up! Be the one who makes it. /

  • Alain says:

    Self employed for 20+ years. First thing you need is to be ABSOLUTELY comfortable with uncertainty. Regardless of what you decide to do, being self employed you will rarely know where the next few checks are coming from. You need to be real honest with yourself that you can deal with this. In twenty years of self employment [successful 6 figure hospitality consulting/lobbying] I rarely could tell where my money was coming from 90 days out. I simply did the work, persisted and it all worked out but the anxiety never left. Your partner, children, family, friends, bankers etc are usually not that accepting.
    If you want to be self employed because you hate looking for a job you probably are not cut out for self employment because every single client, every single piece of work is another “job search” – over and over again.
    If you want to test the waters with little or no risk try volunteering. “Social entrepreneurship” is not the latest or greatest but the barriers to entry are low even if there is no remuneration. Good luck.

  • Kanwal Sarai says:

    The first and most important step is to take some time and determine what is your passion, what are your natural talents and abilities.

    What comes easy to you that others would find hard to do?

    What do you enjoy doing?

    Going out on your own is hard work at first. Running your own business is definitely more than a 9-5 job. If you use your natural talents and abilities, the work won’t feel like “work”.

    The next step is to research if there is a demand for your product/service. Can you make money?

    Based on what you described, I think you will have to return to the workforce (at least for a little awhile), but you can certainly start your business venture right now and then continue to work on it on the side. I know you mentioned you “can afford to spend a few months without income”. But as with any start-up you will probably make $0 in the first 12-24 months (or maybe even longer). I’m not trying to scare you, but rather prepare you for reality.

    The only way you can avoid a 9-5 job is to have funding either from:
    – your own savings
    – family/friends
    – or a spouse

    Going out on your own is exciting and energizing if you love what you do, so figure that out and go for it!

  • The Creative Beast says:

    WOW! so much great advice is here for the picking and I’ve been gobbling it up since I too am in a similar position as Anna having been laid off and starting to figure out how to be a self-sustaining self employed artist/entrepreneur.

    Here is my 2 cents for what it’s worth…

    Penny#1 – I have to agree with Helena, Gregory and Travis on the “take time off/ take a vacation/ leave the country” line of advice. Sometimes you really do need to take some time off to put distance between you and the life you previously lived so you can begin to ease into the life you really want and that time might also help to clarify what you want to do with your life that will bring the most joy for YOU

    Penny#2 – Though I have been with the same tax man for over 6 years and greatly appreciate him, I’d LOVE to have a tax person who was attuned to creative entrepreneurs, who could make taxes more FUN and less stressful! If you do choose to go this path, PLEASE let me know if I can hire you to do my taxes in the future =-)

    Much luck to you Anna!

  • Javier Munoz says:

    Brilliant! Crowdsourcing advice…

  • Carmen Mak says:

    Start with the thing you honestly BELIEVE you can do well and go ahead! However if you are not certain, don’t rush into anything but give deep thoughts about why you want to do it and what you want to get out of it, whether people can benefit from it greatly and what is your ultimate purpose doing it.

    Otherwise you may either end up giving up in the middle of the way or defeated by challenges. A clear picture of what you want to do help you with persistence and courage! Good luck to us all! 🙂

  • Mavis says:

    There’s so much great advice laid out for you here, and I’ll try not to repeat any of it, except to say, again: live without what you can live without. Cut expenses, cut them now.

    One of my favorite online resources/mentors is Marie Forleo and she calls herself a “multi-passionate entrepreneur”. I suggest you check out her site for online business advice.

    Etsy and/or becoming a tax consultant for creative entrepreneurs sounds like a fantastic idea! But if you wanted to also get writing in there (and why not? I do it and love it), get a-searchin’ on craigslist, too. Will you find paid work there? Maybe/not. But I’m pretty sure you’ll find somebody to write for and the goal here is to get your work published and online, fast. You need to build a portfolio. In the beginning that may mean writing for free. Having even just one piece online will help get you the next gig. Start with a blog and write for yourself first, but get your perfectly spelled, grammatically correct words and sentences out there for people to check out.

    Passion and inspiration are great. Discipline and skills are better. Work begets work. I promise this is true.

  • Joseph says:

    Congratulations, Anna! Most people aren’t lucky enough to get laid off!

    My advice to find your life work? Imagine that someone very close to you is dying too young from an incurable disease. Really get into the feeling, close your eyes and imagine it. Then think about your life and how you want to spend it. This exercise will put everything in perspective for you more quickly than any other method out there.

    Good fortune…

  • Cindy Fortin says:

    Read Barbara Winters book – Making a Living without a Job.

    I am excited to come back and read more answers from the other comments here. What a great question.

    I am at a half way point. Some income from self-employment but still waiting tables part-time. I need to push to the next stage.

    Good luck to everyone who is taking this journey.

  • Charles Franklin says:

    First of all, know who yourself and what you have to offer really well..

    Secondly, Create a plan to provide that service better and faster than you did before.

    Third, Budget for your plan

    Fourth (and Lastly) Grow your business and your services by interacting with educational courses, mentors, and your customers.

    Charles Franklin
    (Future Administrative/Research Specialist Extraordinaire…)

  • jon r says:

    Find out what puts you in ‘flow’, and find out if it’s marketable. Focusing on flow activities will keep you inspired and enthusiastic, which is essential for you to succeed.

    George Bernard Shaw’s words, made famous in a Robert Kennedy speech, are good to personalize, “You see things; and you say, ‘Why?’ But I dream things that never were; and I say, ‘Why not?’”

    When I ask myself “why not?” it broadens my vision, I’m optimistic and I see exciting possibilities. If I’m negative, it narrows my focus, and I feel stressful, and it becomes impossible for me to think creatively.

    Go on a learning binge! Listen to audio programs. Read as much as you can, about your craft, about business, about planning, about success, and about others who have succeeded despite all obstacles. And never, never, stop believing in yourself.

    Once you truly decide what you love to do, and feel you have the ability to get the resources needed to launch – follow your plan and don’t look back.

  • Carol Todd says:

    Congrads on making this monumental decision and turning a negative into a positive.

    Regardless of the path you take you will need to focus on your new business venture without fear of living in your car of not being able to eat. This means realistically look at your finances and decide how little you need to live for the next year. If you are single you may need to make adjustments that will reduce your expenses. i.e. a smaller apt. or a room mate.

    Be in love with your business no matter what it is. Being self employed is rewarding and stressful. If you don’t like change or uncertainty then hook up with your local employment department and get a day job. If you are adventuress and can take a risk then go for it.

    Good luck and best wishes!

    A former entrepreneur who likes her day job. LOL

  • Adele says:

    First, sit still and picture your future self. What does she look like, where does she live, what is she doing at that very moment. She will probably be alone but that’s normal. We all see ourselves as alone so ignore that part. Is she writing, teaching, filing… ? Just observe. Afterward, write everything down. Look at your notes and try to figure out what her career is. Then figure out how to do that. Pick that one thing and don’t look back. Dig a deep well, not a million 2-foot holes. And don’t deny your vision. Deep down, you know the you that you long to be. Trust yourself.

  • Sayan Sarkar says:

    This is the perfect time to start your own business! You are eager to learn and have adequate time to work on your own. Also, it’s a down economy, and if you can start and succeed now, just think of the outcome when the economy improves!

    Based on your situation, here are my thoughts:

    – Start consulting in the field that you previously worked. How? ONLINE OUTREACH. Start a blog and give away quality, free content that is useful for those in your field. While doing this, either develop a ebook/audio/video product for sale, or start freelancing as a consultant. When your blog is well known, the purchases or consulting requests will start rolling in!
    – Or build a personal finance practice. Begin a blog/site with quality, free content about how to live and maintain a debt free life. Just think of how many people out there (especially now) are debt-ridden, strapped for cash, and trying to find reliable thoughts and tips on how to better their financial situation. Lead by example!

    Best of luck to you!

  • James Harrington says:

    Don’t put pressure on yourself by needing to succeed immediately, unless pressure is what you need. Some people do, for others it is just a hindrance. Whatever you decide to do, devise a plan b where you can still pursue it even if you go back to work. That means it has to be something you love. That way, if it doesn’t work right away – and for most people it doesn’t – you can improve at it and have the option of pursuing it full-time in the future.

  • Tony Fuentes says:

    Congrats on your lay off! It’s the beginning of a new path, for sure!

    My vague advice would be to start. The reason you don’t know where to start is because you have more than one option. So just pick one, and start. The path will become clearer as you walk it.

    My more specific advice would be to choose tax prep services, specifically for people who are recently unemployed. Since you just got laid off, you can totally sympathize with people who are in the same position and can’t afford to pay full price to do their taxes. Offer your service at a discount and ask for referrals from everyone you work with. Build your book organically and let them know you work with the gainfully employed as well. You can literally find your first clients at the local unemployment office! It’s like someone did all the work for you!

    While you’re doing that, start a blog and write about tax prep for the unemployed.

    My two cents.

  • Heather says:

    Fortunately, you already have some excellent habits in place (no debt). Kudos! Money tends to run out quickly, so the first thing I would recommend you do is to cut your living expenses to the bone (no cable TV, little to no eating out, no Starbucks), leaving yourself very limited discretionary spending.

    Unlike many other folks here, I’m not going to recommend you dig deeply into yourself and follow your heart. You need to create a business that meets your financial needs and rewards you with all the benefits of self-employment. Yes, you can create a business around your skills and interests, but at the end of the day it’s still a business and must be treated as such. You need your work, and you need your hobbies. Do you think Chris writes when he feels like it, or do you think he is disciplined and focused about his work?

    You must be analytical if you enjoy doing taxes. I would suggest you spend several intense days brainstorming all the business ideas which interest you. Pick your top three or four and flesh out business plans. Seek mentors, advisors and business people for input and then go for it!

  • betterthanliving says:

    The biggest problem is that you only have a few months before you will need income. Unless you are unbelievably lucky or already well-positioned, you will not be able to generate a good income in that time frame while undertaking a new venture.

    I suggest getting a part time job to just pay the bills, but not enough money such that you lose the urgency to push forward. If you have few responsibilities, you can maintain such a lifestyle for a year or more and give yourself the time to find a winning business idea, without having compromise too early due to lack of funds.

    From that point, following a lot of the advice already suggested becomes reasonable, such as just trying something and seeing what happens or following your existing network.

    The most efficient but possibly least fun business growing strategy is to work directly from what you already know and can do. Anything that requires new expertise or learning may take longer before the real business opportunities can be seen and developed.

  • David Urmann says:

    All the advice here is great. I think the toughest course might be just to focus on one thing and act. Its possible you will get a lot of ideas but spend a few weeks thinking things through and then put one idea into action and do it well. You can make a great living without getting a paycheck.

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