Managing Your Time as a New Freelancer

Boba Fett Freelance

“When you come to a fork in the road, take it.”

This series poses questions from readers. You’re invited to answer! You can also send in a question for a future post.

Today’s question comes from Maria in Italy. Ciao, Maria!

One year ago I lost my job, and instead of looking for another I decided to try working independently. I was able to convince my former boss to let me work on a contract basis two days a week, and then I picked up another assignment that requires another day or two. Most of this time is flexible, which is great. I’d rather have the ability to choose my time 2-3 days a week than work every single day in the office.

However, this flexibility has also been challenging. I find myself in a constant hurry to get everything done and shifting from project to project. Working for yourself in Italy doesn’t seem as normal as in some other countries. I’m struggling a bit … how can I manage my time?

This is tough! After more than 15 years of working for myself, I still struggle with it.

One thing that helps me is to focus on the deliverables. What do I have to get done, exactly? Those specific outcomes are far more important than whatever time it takes to achieve them.

It sounds like you have a similar situation in that the hours don’t matter but the outcome does—which is great. When you’re struggling, try to get to the next milestone or deliverable… and then take a short break or just do something else.

That’s my $0.02, but I’d love to hear what other people think. What would you suggest?

Share your comment below. We may feature some comments in a future post.


Image: Scott

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  • Nick says:

    I totally love the recognition that flexibility is challenging. I keep an 8:30 to 5:30 but have several projects on nights and weekends, and with a wife and two kids who I’ve committed to being “present” with. I’ve involved them in several projects, which has been fun. But that leaves limited time. With a seemingly-never-ending to-do list, prioritizing items and focusing only on activities that move forward and are able to be repurposed has helped me move forward in a seemingly big way.

    For example, instead of writing one blog post and moving on, I’ll record podcasts and send out interview requests, which can provide networking contacts, audio recording, transcriptions that can be used to spread word about our message, and more ideas for other interviews, products, and services.

    Having a well-defined goal and then focusing on high-impact items has been critical for me. Great, great post, Chris!

  • Jacqueline says:

    Get your to do list ready. Seriously. I keep a list of what needs to be done and I check stuff off. I have been working solo for 10 years and without it (or when I don’t want to do a list because I am a rebel) I flounder. I have tried everything to keep focused and the humble yellow pad with a list and a place to check stuff off or cross it out when it is done is what keeps me motivated and on track every day. I also allow that some days are just foggy and I am unfocused – that is ok as long as they don’t last too long.

  • Karla says:

    I find it helpful to track the major non negotiable in my schedule, the must do’s each week. As a freelance social media content coordinator, I have a calendar for each client, to help keep me focused. The flexibility can be daunting without an action plan!

  • Joshua Tilghman says:

    I don’t freelance full-time, but I have the summer off and I also run into this problem during those 2 months. I have to focus on and accomplish one task at a time, until it is complete. If I try to multitask, I lose a lot of productivity.

  • Britt Reints says:

    Concentrating on the deliverables helps, and I think it’s how I manage my big “trick”: maintain a manageable to-do list.

    People are always shocked to hear I never have more than 3 things a day on my to-do list, but those are three important things, not three time fillers. I find this helps me keep a good balance of focus and flexibility.

  • Ratana says:

    I’ve been freelancing full time for the past 3 years, and what’s helped me the most is to keep my day structured (almost) like I’m still working a 9-5. It sounds counterintuitive, but what this means for me is: I still get up early & get my a.m. run in, then use my morning to work on key projects (e.g., major client deliverables), and my afternoons for meetings and marketing (drumming up more business)! Since I’m my own boss, I can be flexible – run an errand if I need to, schedule that doctor appt., but it helps me to have a general structure so that I don’t give in to the temptation to slack off or work on something that isn’t fully productive. I hope this helps!

  • Joel Pitney says:

    Great post. I’m new to the freelancing game and have grown my business to an almost overwhelming level over the past 8 months. . . . so naturally I’ve struggled with time management. I agree with you Chris that the main goal is to focus on deliverables, not time, because that’s all your clients really care about. One thing I would add to that point is making sure to always put yourself in your clients’ shoes. Think of the work from their perspective and then decide what to focus on for them each day. I’ve found that my own feeling about what needs to be done is often different from theirs, and to be honest, in most situations, I’m actually expecting more than they are…which leads me to put in too much time. I try to make progress (in my clients’ eyes) every day for every client. . .and that seems to be working so far :).

  • Tamara says:

    I struggle with this sometimes too, Maria. Have you ever heard of the Zorro Circle? It’s like what Britt suggests, but even more focused. (Do you know the story of Zorro? He was too unfocused/drunk/blinded by rage to learn proper swordsmanship, so his teacher drew a small circle in the sand and told him nothing existed outside of it until he’d mastered what was within the circle. Here’s one blog post about it:

    Basically, draw a circle on a piece of paper or a white board and write down the one, most important thing you should focus on. Nothing exists in your world until that thing is complete. It should be bite-sized, like, “Write first draft” or “Make five follow-up calls.” Once you’ve completed it, take a break to reward yourself… then make a new one!

  • Anthony Gold says:

    I can completely relate to the challenge of managing time. And at one point in my career, I could have spent my entire working hours simply replying to email and still never stay on top of it all.

    I agree with Chris’ suggestion of focusing on the deliverables as well as the big-picture stuff (goals, relationships, growth, etc.). A technique that I’ve found helpful is a kanban-like system with projects for each major area (and client). Probably the easiest way to explain what I mean is by way of example. (Everything I describe below is pretty easy to implement with Gmail or countless other free systems.)

    Action -> This Week -> Today -> Now

    I have four queues (buckets) to manage everything I do. The first is called Action, which is anything that I have to take some action on. If I get an email that requires some response or some work that I need to do which will take me more than a few minutes to complete – then it goes into Action. All of the tasks that I need to do for all my work go into Action. Obviously this is a big list – oftentimes around 100 or so deep.

    The second queue is This Week – and those are all the tasks that I want to accomplish this week. So, at the beginning of each week, I scan through my entire Action bucket and select those that I want to get done this week and move them into This Week.

    The third queue is Today – those tasks I want to get done today. So, each morning I will select those items from the This Week queue that I am committing to completing today and move them into Today.

    Finally, I have a Now bucket. The reason I do this is because multi-tasking was killing me. I got way too distracted and kept bouncing from one distraction to the next. So, my Now “queue” contains just one task – the one I am working on Now. So, throughout the day, I look at my Today queue and select one item to put in the Now bucket – and then that is all I work on at that time. If I need to stop working on that particular task (for whatever reason), then I stick it back in the Today bucket. This process forces me to be very selective about what I’m working on, and has helped me greatly from getting too easily sidetracked.

    And that’s mostly it. There’s a bit more to it like using project labels for each client, handling the steady flow of incoming email, and other buckets for completed tasks, someday tasks, and tasks I’m waiting for others to complete – but overall this system enables me to easily see what commitments I’ve made to clients and to myself – and to be very intentional about how (and where) I manage my time.

    Hope this helps.


  • Natasha says:

    These are great – like Ratana above, I also try to structure my day into a 9-6ish, but with the flexibility of getting to an early workout class, or a longer lunch meeting, etc. I love the idea of mornings for key projects and afternoons for meetings/marketing – will put that into action, as that will give my day a better structure. I try to set my weekly goals and break those down into actionable to-do’s every Sunday, so I know what I need to accomplish each week. Lately, I have found that organizing each hour has been helpful, so that each task has a time limit, as I tend to way overthink and overanalyze things, especially when it comes to my own marketing (making calls, social media posts, etc). I also make it a point to attend at least one “event” an evening each week to continue building community, converse with new people, etc..

  • James Canali says:

    I find the year I did freelance work entirely I struggled with the amount of freedom and felt a sense of never finishing work. I wanted to try some new things and have been working at Starbucks as a supervisor. To me this for a season, is helping develop me as a business person. What constrictions like a 9-5 job could help you guys for a season?

  • Joe says:

    Hi Maria and Chris
    I recommend tracking your time for client work; the direct paid work that is not paid by the hour (pay per project is much better).
    I use Toggl which is a neat desktop and mobile application that is quick to start and run.
    When the timer is on, I know to put my head down and get it done. The more efficiently you work, the quicker you will get it done. The more you procrastinate, the lower your hourly rate. You can’t cheat the system, that’s why it works.
    I might do 2 hours of one project. Then 2 hours of another. Then 2 hours of another again depending on my mood. Afternoons are for my own ideas and fun, of course.
    I think this reinforces what a lot of others have said. Fantastic, I’m on the right track 🙂
    Hope that helps,

  • lavinia says:

    Hi Maria,
    I understand your feeling very well as i’m a freelance in Italy where everything seems (and is!) much more difficult than anywhere else in the world… And I also feel that sometimes, as you described, we tend to be overwhelmed by our to-do lists (which are, by the way, necessary and very useful)
    Anyway, i recently found a strong support on this worderful website (sorry for the soloenglish speaking, it’s only in italian! C+B means Casa più Bottega something like Home+Work, i.e. people who live and work in the same place, your home).
    They always have very useful (and funny!) posts on how to manage your time among freelance working, housekeeping, kids, family, everything (!!!)
    Hope that helps, ciao!

  • Daisy says:

    I teach online. We work in an office full of cubicles, but there is a definite time management element. Those of us who master the art of prioritizing are much more relaxed and more likely to meet deadlines like progress reports and grades.

    I, too, focus on results. I need to make certain phone calls on schedule, so I make a point of scheduling those in blocks, leaving me with blacks of work time. I use the blocks of work time to handle grading and creating lessons for my virtual classes. My to-do list and my outlook calendar are my friends, not my enemies. Having those tools in place lets me focus on the work I’m doing rather than wasting brain space worrying that I might forget something important.

  • Jake Jorgovan says:

    I had this same problem when I went out on my own. I felt like I was all over the map and I wasn’t getting anything done.

    Ultimately I ended up diving into several productivity books for creatives which completely changed my life.

    Manage Your Day to Day – By 99u – This book is incredible and features stories from some of the most successful creative professionals in the world sharing their stories about productivity and time management

    The Accidental Creative – By Todd Henry – Amazing book as well that will completely help you manage your time and creative efforts better

    Getting Things Done – By David Allen – It is a bit more dated, and more focused on business professionals but it is a great read as well. As few tactics from this book completely changed my life.

    I ended up combining all of these elements into my own productivity system and wrote a free ebook on it called ‘The Focused Creator: Learn the Art of Follow Through & Achieve Your Goals’. Here is a link if you are interested:

    If you spend a bit of time every day learning about ways to become more productive, over time you will get much better at managing your time. There is no silver bullet but you just need to build a system that works for you!

  • Gray says:

    I would agree with almost all of the above comments – though I found that David Allen’s GTD system didn’t work so well for my creative endeavors, and neither has pomodoro techniques (too much interruption of flow).

    The worst part for me is the “never done” scenario. There’s always something else you could be doing, some other way you should be hustling to improve your brand, get a better client, increase your skills… There are two things that have helped me.

    One is, an iphone/Chrome app that works as a to-do list with almost the same kinds of buckets as listed above. It has the ability to schedule tasks, to add in people, and gives a satisfying swipe so that I never feel like I’m going to misplace the list but can still feel good about completing things.

    The other is embracing Mailbox Zero. I used some of Merlin Mann’s suggestions and also the Mailbox iphone app and every day I clear out my inbox at least once. That gives me a feeling of being in control.

    As for scheduling, the hardest thing to remember was that breaks are mandatory in the “real” world, and they should be for freelancers too. I take a long, hour-and-a-half lunch, and while I’ll let myself start work early I never work late any more. As they say, no one ever dies wishing they’d spent more time at their desk. I spend time with my partner, with my grandkids, and people who are important to me.

    Good luck!

  • Gray says:

    Ack! Forgot one more thing! I do a weekly “SitRep” with another freelancer (who lives across the country). We talk to each other about projects we may be working on, about challenges, and basically keep each other on task. That weekly meeting is essential to both feeling connected and remaining focused. I highly recommend you find a partner who you can do that with.

  • Samantha Attard says:

    Wow! Anthony – I cannot wait to try your system with the buckets!!

    The most important thing I have learned is to actually take my breaks, and to shut down my work in the evening. Working from home, it’s incredibly easy to work on and off from 6am to 10pm, rather than working hard from 9 to 5 (or whatever hours you choose), and then to be done. I like having events or people to meet with in the early evening, so I have a deadline for when I have to stop my work day, and turn my attention to the other important areas of my life.

    Thanks for the great tips, all!!

  • Patty Golsteijn says:

    A big one for me is that I started looking at the bigger picture. We tend to think small, only checking our daily to-do-lists. But you have to also take time to zoom out. What do you want to do this week, this month, this year? Then work from there.

  • Valerie Urso says:

    First of all, congratulations on your new independence! It takes a lot of resilience to work for yourself.

    Personally, as I am a freelancer myself, Evernote has been a godsend. I use Notebooks to organize client work, then can create subcategories for each project with that client. You can also use tags to make everything extremely searchable.

    I keep a running master to do list in a Notebook called “Daily”. Every morning I copy over my previous to do list to a new Note, title it by the date, review what I accomplished yesterday and look at what is a priority to get done today. I use the strike through feature to check off the things I did so I can look back at any given day and see what I did. (I can’t remember what I eat for breakfast half the time, so this is so important for me.)

    I try to incorporate the advice to tackle the most important projects first (especially as a writer, this means getting copy down and out the gate before email) and avoid letting email run my life, but your mileage may vary. I have yet to be able to do this consistently…sometimes the inbox takes over.

    Being organized in this way cut down on the massive amount of planning I had to do to manage dozens of clients. If I need to see where a project was, I can just open their Notebook and go to the appropriate note. If I forget a password or a name or a conversation, I can search for the tag and my note comes up. It’s like outsourcing your brain to a more reliable narrator.

    Good luck with everything!

  • Fabio says:

    Hello Maria,
    I am facing a similar situation, with the only difference that I have not been fired but I came to a breaking point with my professional life. I think that between the two there is no difference if we both decided not to seek another option like me to seize our lives.
    I raised the issue that you have written (how to manage my time and do not find myself living worse than when I was an employee) coming to the conclusion that even in Italy (I am from Verona) you can create a good relationship between income and time taken to produce it. Maria I think that people like us have to identify activities that can be managed in just a few hours a week, if you feel pressure in your activity should reconsider and rationally evaluate if it’s worth it.
    Otherwise we risk to be self-employed only on paper and in reality always be really employed

    Best wishes for your future

  • Kevin Peter says:

    Nobody understands the value of time better than freelancers. Time being money needs a right tool to track and get paid 🙂 without getting hit on the pocket!

  • Catys Sun says:

    A big one for me is that I started looking at the bigger picture. We tend to think small, only checking our daily to-do-lists. But you have to also take time to zoom out. What do you want to do this week, this month, this year? Then work from there.

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