2014 Annual Review: Lessons in Entrepreneurship & Unconventional Work


And… the Annual Review continues! Today’s post builds on Monday’s, with some more specific lessons related to entrepreneurship, writing, and work.

You’re welcome to share your lessons too, and—new bonus!—we’ll award a $100 Powell’s gift card to the person who leaves the best comment by the end of the week, as determined by our cats and biased judges.

Previous Posts

2014 Annual Review Process & Template
Looking Back on a Complicated Year


As is the case every year, 2014 was a busy and active year of work. Despite the various personal challenges (see: sad, late, unreliable, etc.), I still managed to be moderately productive.

Sometimes people ask what exactly I do and how I get paid. Well, I do a lot of things. I essentially have several different careers that operate in tandem, and for the most part, I wouldn’t want to choose between them. When it comes to 2014:

I wrote and published a new book, The Happiness of Pursuit. As regular readers know, this book is about quests and adventures, including my own journey to every country, as well as the quests of many other people around the world.


I published several guides through the Unconventional Guides brand I founded six years ago.

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I gave some talks, at reader events in 40 cities and an additional dozen events, conferences, and organizations around the world.


This year I spoke at several fun conferences (highlights: Alive in Berlin, The Art Of, AwesomenessFest, Copyblogger, CoStarters, Frequent Traveler University), a number of great groups and organizations (highlights: Gumroad Studio, General Assembly) and even a few companies (including my third visit to speak at Google—they have an awesome free lunch there!).

I worked with a great team to produce two big events, the inaugural Pioneer Nation and the fourth annual World Domination Summit.


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and overall I tried to improve, with mixed results. As I said in the overview post, you can be successful and still struggle. But the corollary is: you can struggle and still be successful. A lot of things happened in 2014, and some of them were pretty good!

Nevertheless, in looking at lessons learned, it’s good to look at frustrations, failures, and anything that just feels difficult.


A Few Lessons & Observations

T’was a complicated year, and here are a few things that I learned.

In a changing world, winners stay ahead.

When asking, “Why are things so hard lately?” it helps to take a step back. Are you going against the flow? That’s a great thing to do in life. Fight the power, think for yourself, etc.

But in independent work in general, and especially in entrepreneurship, you want to be leading people forward. Value is created by being helpful and offering genuine solutions to problems. You can’t create a problem; you have to identify problems and fix them.

A few weeks ago I received some great advice from a trusted friend, who said something like:

“The context for much of this world—independent work, life planning, nomadism, and such—is not stagnant. It changes over time, and there are clear shifts in how it’s perceived and applied. You’ve been part of changing it. Part of the reason that it’s evolved comes from you. But you also need to stay ahead of the curve. Your job isn’t to support a status quo that you helped create; it’s to look to the future and speak to what’s ahead.

Now that I think about it, she didn’t actually say all of that. But she gave me the first part, and then I immediately realized the rest. Of course things won’t remain the same! Why should we expect them to?

It reminds me of that old saying of Einstein’s: “Insanity is doing things the same way and expecting different results.” We hear this and think, well, naturally. Who would do that? But then that’s exactly what we do, because we don’t know any better and because it worked before.

As Flannery O’Connor once wrote, everything that rises must converge. To mix metaphors, the world can’t stay flat forever. So we, too, need to change how we approach this beautiful and unconventional world of living unconventionally.

Just because you’re good at something doesn’t mean it’s what you should do.

This is the logical extension of the first lesson. There are lots of things that any of us could be good at. But thanks to higher education and the general privilege of being able to forge our own destiny, selecting the right work to pursue is a major challenge for many of us.

In my case, I could probably be a decent technical writer, jotting down user tutorials or software manuals, or a competent middle-manager, leading a team in a large company and generally exceeding expectations from my superiors. Thankfully, I’m not doing either of those things! No, the challenge is to find what we’re great at and do that thing.

So I’m thinking about that a lot lately, and how it applies to the future of all the different projects I’ve built and want to build. Just because I’m good at something (well, let’s say decent) doesn’t mean it’s how I should choose to invest my limited time in 2015 and beyond.

No matter the endeavor, I always hit a ceiling of success… and then settle.

I’m pretty good at starting. I’m pretty good at delving into problems and finding interesting solutions. But as I discover over and over, I’m just really not good at sustaining the same project over time. For some reason, I always hit a ceiling of success. I don’t really know why.

This blog is the exception. For six years I’ve found joy and fulfillment in writing here. When I started to feel stagnant, I changed up the format this summer—and now I’m just as energized as ever. Aside from that, though, everything seems to grow to the “Wow, that’s impressive!” level… before fizzling out or settling into a long period of, “Oh, that’s okay.”

My good friend Jonathan Fields once told me that the problem was “too many wells”—as in, too many places to properly devote the attention that any one of them needs to grow. And he’s probably right, as he usually is.

The alternative to scaling yourself (and therefore stretching yourself too thin, inevitably) is to specialize and deep-dive into something. When done well, this is a beautiful thing. A few people (who are also good friends) that do this well are Amy Hoy, Marie Forleo, Ramit Sethi, and Nathan Barry. I’ve been inspired by each of them, in addition to others, who all started as generalists but have become more and more successful over time as they’ve chosen to specialize.

Ultimately I know it’s a choice, with no right or wrong answer for everyone. It’s also the ultimate first-world problem, just like being served packaged nuts in First Class (the horror!).


Three Goals As I Evaluate Future Work

I’m not quite to the “looking forward” part of the review—that will come over the weekend and early next week. But there are a few things I already know I want to do.

Consider “what sparks joy” in my projects. In one of the most popular posts from this fall, I wrote about Marie Kondo’s model of discarding everything that doesn’t spark joy. She applies this model to the decluttering of a physical space, but If you’re self-employed or can otherwise determine many of your priorities at a job, you can also apply it to work in general.

I’ve been thinking a lot about what I am uniquely good at—not just what I can do, because I’m a bit of a generalist and I’ve found lots of ways to fill my time and make money as an entrepreneur—but about what best suits the limited amount of time available each day, as well as what brings the most joy.

Return to 1,000 words a day. On book tour, everyone asks about this: “How do you manage to write 1,000 words a day?” Well, the honest answer is: sometimes I don’t. Somehow I acquired this reputation, probably because I told everyone I did it every day with no exceptions. And I did, for a long time, but then I fell behind.

Over the past few weeks, I’ve taken drastic measures in this regard, and they’re actually working. Yay. I am a writer, and a writer writes. I’ll share more about how I addressed this discrepancy in an upcoming post of its own.

As always, consider the bigger picture of “what really matters.” Going forward, I’m going to be more relentless in paring down. I’m going to remember the cost of small things. I’m not sure I’ll ever fully embrace the “only do things that are at least a 90 out of 100” philosophy, but I’ll try to be more selective one way or another.


Your Turn

Next year I look forward to much more writing, including completing a full manuscript of my next book (more on that at some point, but not just yet).

I want to do a better job of serving you, dear readers, and everyone else associated with our awesome community. I want to look to the future and not remain stuck in the past, even when the past has been good.

How about you? What did you learn about work in 2014?

Comments here.


Image: Kevin

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  • Meg Schneider says:

    I learned the importance of negotiation and knowing your own value. I started from taking the first offer that was accepted to now carefully negotiating my freelance clients.


  • Bruce Hoag says:

    For me, it’s less about what I learned in 2014 and more about what I’m learning. It’s to focus relentlessly on what matters. Greg McKeown calls “essentialism.”

    There are so many legitimate things to do that it’s hard to recognize them for what they are: distractions. Separating the most important for the acceptable, the okay, the all right, is the challenge. I imagine that it always will be.

  • Zicky Villette says:

    This is something I manage to learn every year but always seem to forget. That there is a huge difference between what you don’t know and what you don’t understand. Things you don’t know, you can go to Google to learn more about and try to understand them. For the things that you don’t understand that is where I believe you need a little help and collaboration to get you over the edge.

    This has been an interesting year for me because I have learned that I have a tendency to settle but also regress. It has been difficult for me to come to terms with but great for me to learn. Although I have well defined goals, I usually have poorly structured plans of obtaining said goals. I am working at this point to develop that structure so that I can obtain my major goals, especially in my health.

    It has a been a great year for productivity, I have learned what works best for me in regards to work and getting things done. Learning a little more about myself everyday. Thanks for prompting the mini self reflection

  • L. A. Silberman says:

    I learned that just because the time is finally right to do something it doesn’t mean that ‘the voices’ that held you back have been silenced.

    So “Fasten your seat belts. It’s gonna be a bumpy ride,” and take it anyway.

  • Anita Chase says:

    This year, I am learning the value of slowing down and paying more attention to details. I am used to juggling many projects and people at once. I am a quick learner (although I don’t always retain as much as I should) and I get along with almost everyone, so I am used to getting positive reviews with almost everything I do, but this year I switched jobs from an executive assistant to working with publications, as I felt it would line up better with my long time goals of being able to take my job with me on the road. As one of my roles is editorial assistant, it has forced me to slow down and really pay attention to concrete details, instead of just using a friendly personality and willingness to help everyone to keep things in motion. This has also made me look at many other areas of my life where “good enough” and a friendly smile has been good enough to get me by for a very long time. I don’t think that being friendly is a problem, just that I need more measurable quality for my work, without my personality. It needs to be able to stand alone.

  • Susan Tripp says:

    I learned a key lesson.. it’s not about having the resources, it’s about being resourceful.
    Happy 2015!

  • Caelan Huntress says:

    This year I learned that working for myself can be exhausting and result in mediocre work, and working for someone else can give me the energy and creativity I need to make better things. It was a surprising revelation.

    Thanks for opening your playbook, Chris, and sharing your introspection with the world. It’s always an inspiration to see inside your process.

  • Wendy Reese, whole being inc says:

    Chris, as always, you inspire me (and so many others) in how willing you are to show up vulnerably and transparently. When I interviewed you for The Whole Being Zone last month, it was a dream come true because you have been my mentor from afar for so long. You spoke about wanting to improve and I must confess, it really bothered me because of the energy behind it. Improvement is an interesting and somewhat flawed concept. How can you improve perfect? You can’t. We are not here to improve, we’re here to remember. Which brings me to my lessons learned.

    1. I remembered why I started playing small in the first place- to feel safe, loved, and accepted by people who were also playing small. My light shining fully triggered a reminder of how they have managed to dim their light, posing a threat to their illusion of being less than perfect. I can see how my choice has played out all these years. Awareness is the powerful first step to change.

    2. I asked for help- from people who had managed to break free of their illusion to shine brightly again, from my angels and guides (yep, I’m pretty woo-woo), and through my actions with each tiny step I took in showing up fully.

    3. I became acutely aware of how I use excuses and read them as facts to support me playing small. Now I ask, “is that true?” and “what would it take to shift?”. This requires courageously bold honesty, accountability, and responsibility. It requires me to do something different every time I catch myself making an excuse. In that way, I am re-mapping my mind so my internal GPS doesn’t keep me stuck in old maps and routines.

    4. I realized as long as I have been doing what I do, I am great. The problem is I am the best and oldest player in the little league and it’s time to move up to the next level. This is scary because I won’t be the best anymore, I will have to do the work and pay my dues, I’ll have to learn. New routines and discipline are required in order to become world class. That takes effort and commitment, but if I ever want to stand on one of your stages as a presenter, I must do the work.

    5. Actions speak louder than words. I must show up day in and day out, focusing on what will bring my dream to fruition, participate in the conversations and relationships of the people I want to serve, celebrate my successes and learn from setbacks. Just thinking about it won’t get me there….ever.

    2015 will be an epic year for those of us who are upleveling and intentionally striving to be whole. Thank YOU for being a pathfinder for remembering wholeness, greatness, and already existing perfection.

  • Tricia says:

    This past year has been very personally and professionally challenging. In the midst of my slump, I have sought inspiration from your blog and books. I have really learned to treasure and appreciate my own happiness. I have been more proactive at trying to change around my own professional dissatisfaction and leave my toxic work environment. I’ve increased my faith in my own skills and expertise, which has helped me launch a start up during the past two months. I feel so empowered to work on something I am passionate about and have autonomy over my own future!

  • Rudiano says:

    Hey Chris, I admire your candour! Well for my part, most of my lessons were learned in the second part of 2014, from July the 17th, when I launched my site. No wonder… You can only learn when you stretch yourself a bit. 🙂

    First lesson: Technology is a tool, I shouldn’t let it lead me.
    I realise the clarity of my message has suffered as I was following the stats on my site, the retweets and the like (You said it before, but I still had to make that mistake, aaaargh!)
    In 2015, I’m making sure I stick to my guns, digress less.

    Second lesson: Content is great but action is better. If I make time to grow rather than just share what I learned over the years, I will stay ahead of my audience and will be able to deliver value week after week.

    Third and last lesson: give something away to grow my email list! Actually, writing this comment gave me an idea! Aha…
    Stay tuned.
    Thanks for the inspiration!

  • Will Spencer says:

    2014 was my first full year in business. I saw the ups, the downs, and even a few sideways. I learned that the worst case scenario never happens and looking forward to 2015 that loftier goals will be set and bigger risks taken. I took one passion and turned it into a business and learned that I could bring all of my passions with me to work everyday. Not only has this grown a better business, it has become a crucible for enhancing my own personal growth. For me 2015 starts right now!

  • David Orman says:

    This year, I am not creating specific goals. I will simply be happy, creative and open to helping others. In the process, what I am to do and how I am to do it, will unfold. To me, that is the perfect way. No stress. No strain. Just going with the flow of Nature.

  • Carrie says:

    I am at the end of my first year as a freelance web designer/developer. I have wanted to work for myself for over a decade, so finally making it happen is huge for me. I’ve gathered excellent resources with solid advice and guidance on starting a business and living a balanced life. I tend to over prepare and research obsessively before beginning any endeavor and becoming a web designer/developer was no exception. I just knew that by the end of the year I’d be living the dream… ha!

    This year I learned that no matter how much I researched, studied, observed, planned or mentally prepared, there are pitfalls that have to be experienced first hand. The good news is, the lessons learned were hard won and I am better for them. I have so much more assurance in setting boundaries and expectations and ‘sticking to my guns’ because the outcome otherwise gets messy.

  • Jake Kot says:

    Earlier this year I heard a quote from Eben Pagan, a simple play on words with a message we’re all familiar with. He stated: “The goal, is an extraordinary journey.” I just can’t seem to find any philosophical rhetoric needed after that statement – something I rarely experience.

    With that in mind, it’s become abundantly clear to me that every moment of a personal transition (which quite honestly never ends) deserves my attention, striving to make it as gratifying and fulfilling as the envisioned outcome – the rewards become ubiquitous.

    This type of life and/or work-life approach if you will, has changed everything.

  • Jen Zeman says:

    It’s humbling for me to read this Chris because it makes me realize I’m not the only one who struggles with reaching a plateau (not that I’m celebrating your struggle!). The biggest lesson learned for me was with launching my first business (South Pacific Bound). Despite all the reseach I completed, I found myself delving too deeply into the world of advertising and marketing (specifically, social media marketing) and being swayed by the shiny, loud “experts”. I also didn’t have any real solid plans written down, basically winging it from day to day. I’ve been an avid follower of yours for awhile now (along with Leo Babauta, and Scott Dinsmore) but ended up doing a 180 from the advice and lessons the three of you have provided us. Long story short, SPB tanked rather quickly, I racked up $10K in credit card det, and now how about 200 t-shirts stored in my spare bedroom. *FACE PALM*

    But, this failure allowed me to rediscover my original love of art (something I gave up right out of high school). I’ve never been happier! I’m in the process now of writing my review of 2014 and setting forth solid (written!) goals for 2015 – the first time I’ve ever completed this. I already feel like I have a solid start to 2015 because of this focus.

  • Janice Pridgen says:

    I have had a productive and trying year. Although it is still not over. January is still a few weeks off. During the summer, (on the weekends) I have started to build furniture from pallets on our property in Springdale Washington. We currently live in Sudden Valley (Bellingham) Washington. I did not finish the projects mainly because of time and money. We came back to the property in November after my seasonal job had ended and the weather had started to change to winter. I now know that trying to build wood furniture when it is cold outside is stupid. I think I broke it because I heard it crack but it was 10 degrees outside and I decided to leave it alone till spring. Can’t wait to see what damage I did. Nonetheless, it was an interesting experience and now in the winter we sit waiting for unemployment money to trickle in until my seasonal job starts back up in February or until I get a full time year round job in something else. Either way it has been difficult knowing we are moving but not being able to do anything about it because we are building from scratch and we don’t have anything built to keep us warm in the winter. Torn between the two properties has made me extra emotional and that is never a good sign. Course I could be menopausal too but that’s just crazy talk. Either way I think I have learned that in order to get what I want I have to settle with working for someone else at least for 3 more years or more. Only because I cannot be creative with my spouse being who he is ( type “A” personality) where he needs to be in control of everything and my time is his time. It’s been a tough decision but this winter, while being at home alone, I have had the opportunity to enter 3 writing contests. Of course, I could have used the money for groceries now but I took a chance on them so we shall see. I know I am babbling but it has been a rough year. Hope next year is better for me and for you. Merry Christmas and Happy New Year. It’s been a pleasure reading your blog.

  • Ryan J. Pelton says:

    I am learning… ready… profound… just start. I can live in my head waiting for the perfect time to start that business, write that post, or have that conversation. The time is now. Right now. Not five minutes from now, five years from now, right now. There will never be as good of time as now. Then, once you start, correct as you go. Nothing is perfect. Nothing ever will be. But, now is the time to start.

  • Sara says:

    I had a big year. I quit a dreadful job – one that paid relatively well, but when it came down to it was crushing me and my happiness – to go to a friend’s wedding in Chicago. I chose happiness. And then, well the rest of the year went to shit. Okay, maybe not to shit. But I’ve struggled more than ever. I spent months driving 60 miles round trip to a retail job, interning at a not-for-profit book center in NYC, walking dogs, and doing errands for another small business owner in NYC to stay afloat. I didn’t do very well at all, and yet, I’m still here. I haven’t lost my car, or my apartment. I’ve asked for help and I’ve received it. In all of this “working”, I’ve lost a lot of my own sense. I’ve lost the spark and motivation. I’ve doubted whether I could have my business – I had a melt down on a street corner and almost moved in with my Mom.

    I’ve also learned that it’s time to say no. Time to say no to all the things that keep me from doing what I should be doing – from reaching my goals for my own dreams and passion.

    Work is about what we love doing. Running around trying to tie up lose ends is not helpful. It is not even work. It’s work in the traditional sense sure, but it is work that keeps me from doing the real work – the work I am meant to do.

    Work is also about us. It’s an expression of who I am. Who you are. Who we all are. When I’m not working on the things I love, I’m not working. In fact, I’m getting farther from my work, my values and myself.

  • Chelsea says:

    This line right here, “No matter the endeavor, I always hit a ceiling of success… and then settle.” Hits home for me. I haven’t been able to figure out what happens to me once I achieve some part of my goal. I never thought it would be that I settle, but your words really stuck a chord and I have to only agree that I don’t keep looking for more ways to better my success, I just relish in what I accomplished and consider myself “arrived”. Kind of unfortunate. On a happy note! Thank you for sharing lessons learned! You are my inspiration. Blessings.

  • Chris Allen says:

    I made a huge work change in 2014. For the past 6 years I was working full time for a company that was good, not great. I also had a 90-120 minute commute each day. Last month I took the leap to work part time for our church as a project manager. It is a job I have always wanted to do, at a great organization working with great people. I also get to spend much more time with my family, which is worth more than money can buy.
    Next year I look forward to adding value and expertise to my coworkers and finding (and doing) what I am great at.
    As I was reading I noticed the “too many wells” analogy. I am in a men’s group and next year we are launching a program called Into The Deep. Your idea about finding the best well and deep-diving really struck a cord in my life.

  • Sara Everett says:

    In 2014 I have finally learned to say “no”. As much as I want to, I can’t physically do it all. My curatorial business is going very well – enough that I’ve faced three solid months of near burn out. I appreciate all the blessings and opportunities, but I also had to recognize when I had reached the point where I had to turn down a potential client. Hard one, but good one.

  • Artyom Aushev says:

    That’s why I’m here and reading a lot of these posts:
    It’s not only about achieving your goals etc.
    It’s about life style!
    Making changes that will be positive and constructive.
    It very interesting to have challenges. It will make you better at the end.

  • Toni Banks says:

    I learned to set definable goals when it comes to increasing my income. I’m learning to appreciate doing work that I enjoy. I learned that I can get paid to help people. Social service doesn’t mean I have to remain poor. 2014 was a year of disappointments. I want to thank you for the Annual Review because it make me look forward to a new year for the first time in my life. Thanks for all the time you put in it.

  • Karen Talavera says:

    I learned the importance of developing and cultivating partnerships and aligned business relationships. I don’t have to be it all for my clients; I am often just as or more powerful as a sherpa or connector for them. I don’t have to be fiercely independent to be successful and build a name or brand. In fact, it’s not only more fun but a lot less lonely to be in collaboration than isolation.

    We all have an innate need for belonging and community, and I’ve found the more I connect with my peers, partners and competitors alike, the more I create a community of my own that is meaningful to both me and my clients, and the more my clients and business thrive.

  • Nancy says:

    I learned that the flame of passion I thought had been tamped down by forces out of my control, and by battles I did not choose, remained a spark just waiting for the storms to pass. I took my first big leap of faith nearly 30 years ago. I’ve taken many since, but early next year I will be taking one that feels like the first, stepping into a void without a plan or a clue of where I will land.

    It is true that, just because I am good at something, it doesn’t mean I should be doing it for a living. Sometimes it is lonely embracing the new and breaking the old mold way of doing things. I know, however, that is what I must do if I’m to find my personal joy. In 2014, I discovered this blog and it has made it a little less lonesome. Thanks, Chris.

  • Jerry Sterzinger says:

    2014 what I learned …. I better be doing something that matters. If not then I need to find something else that does. All the best to you in 2015.

  • Chad says:

    Love the “open kimono” Chris. Quick question, what does 1000 words mean? Is it a 1000 words of publishable content or do you find any 1000 words (even top of mind, stream of consciousness ramblings) is enough to keep you moving forward? Keep moving forward motivator!

  • nathalie says:

    Very inspired by your annual review as I am myself slowly working toward my own review (scheduled on the bridge between 2014 and 2015)

    So far, I’ve learned that switching perception is what makes the difference between feeling like the sky is the limit, and feeling stuck and overwhelmed by about everything or anything.

    Another lesson following that first conclusion was that cultivating the ‘art of being present’ is the best gift I can offer myself to feel peaceful, grounded, more focused in my work and available for the people I love and care about.

    Last but not least, I learned that I only need to work on something with commitment and being professional -by my very own standards-, to open doors to universes that can only be unlocked with me being active and in movement. The reasons why I decide to work on a project might become irrelevant along the way, but I learned that this is irrelevant. As long as my reasons made enough sense for me to start in the first place, and as long as I stay professional along the way, my chances to connect dots in surprising and fulfilling ways increase exponentially.

    I had many small payoffs this year that resulted from years of smaller projects that lead me to other -slightly bigger- projects that took me where I am today, and looking back I now realize that those dots couldn’t have been connected together to form today’s bigger shape, had I not started with drawing the first dot. And then drawing some more.

  • Maureen says:

    In 2014 I learned:
    1. having a plan makes a HUGE difference in how successful I am with any given project
    2. setting measurable objectives helps keep me focused
    3. tracking my progress helps me stay motivated and accountable
    4. coming from a place of really wanting to help people puts what I do & why I do it in perspective
    5. doing what makes my heart sing makes it all worth while

  • Randy says:

    Just because you’re good at something doesn’t mean it’s what you should do.
    Definitely agree with this point.But the problem is,a lot of people even do not know what they are good at because of lack of self awareness and development.They have no idea of what is their strength that can freely support themselves and their families in a way with fulfillment,happiness and neccessary payment.A person has to do something for a living then gradually can focus on his/her unique talents to lead a happy and successful life.Life is a quest full of setbacks,loneliness,joy and pride.
    Thanks for your wonderful posts,Chris.

  • Daniel Clay says:

    Chris, thanks for sharing your 2014 annual review and 2015 annual plan! I really appreciate you being honest about sharing the struggles that you had, and the tendency to look upon what felt like a “year of failure.” I had a similar year in that respect, yet looking back, it may have been the most productive year ever.

    The other thing I really appreciate about what you’ve shared is that it helped me to plan not only for “work,” but for all of life! Thanks!

  • Kate says:

    This is the year I learned (not just in my head, but in operations and execution) that while excellence is a great thing to go for, waiting for perfection is killer (for creativity, fulfillment, my bottom line). I made a lot of mistakes this year, and had a lot of wins. I’ve also produced more than ever and have learned soooo much about how I operate, what I and my people like/don’t like, and where I can go from here!

  • Kristin says:

    I just went through my what went right and what went wrongs for 2014. This is the first time I’ve done this sort of annual review and it’s helped me understand the base reasons for why I have been unhappy with my life trajectory. It was because I had not made any solid goals beyond just get a new job that pays more. Which was an entirely needed thing as I was sorely unhappy before I got my new job. However, that being said, I haven’t achieved anything, I’ve started many things that went no where, I ended up all over the place, because I have been managing my status quo and not looking upward and outward. I’m just riding the tides where ever they take me and not steering the ship of my life. I’ve got to make it go where I want and not let it wander off. The theme of 2015 is “Want New? Do New!” That is boiled down from the quote “If you always do, what you always did. You always get what you always got.” I don’t like what I’ve got completely, so I’m going to have to do new things. With this annual review, it will be the first time in my life to actually make my goals and start working towards them. I’m the Captain of this ship!

  • Suzanne Schiller says:

    What I learned this year is that reinventing myself has required LETTING GO and a commitment to excruciating honesty (not in-my-head-what-a-great-idea-that-is! honesty, but whole-body-deep-in-my-bones-lived-and-breathed honesty.)

    And during the process I have often felt like a bonsai, over-pruned and impatient, wondering when my leaves were going to sprout.

    I have found during this dark wintertime the greatest joy and faith in my own guiding, shimmering light, knowing that all I ever need to do is preach what I practice, one tiny human step at a time.

  • Brooke says:

    Hi Chris,

    I learned a lot this year, but I’m going to clip this line from you and talk about this in particular, because it’s big and I took action on it this year. I realized a long time ago, why I wasn’t happy with what I was doing, and how I kept getting sucked into doing the same thing over and over again
    ‘Just because you’re good at something doesn’t mean it’s what you should do’ (from your above post) was what I realized and struggled with trying to break free from being stuck in a career I was doing because I was good at it, not because I liked it.
    I realized a long time ago that people were always wanting me to do things because ‘I was so good at it’. They recognized certain talents in me, and focused on those and offered me opportunities based on those. When I sometimes would try to branch out and do other things, the employers that I had would always want me to go back to what they perceived to be the most valuable thing I could offer to them(but that I didn’t want to do), and so I continually remained in positions doing what I didn’t enjoy, but that I was good at because people perceived me as being more valuable to them in that capacity.
    Of course, it feels good to be good at something and to have people recognize you for that so it’s easy to let everyone elses’ recognition of your talents decide for you what you should pursue. But after a number of years of being seen as someone who was really good at a particular type of job and who had this particular skill set, I realized that I was only doing it because I was good at it ,and that in fact it was keeping me from doing anything bigger. From doing all of the bigger things I really wanted to do. I couldn’t grow or evolve or ever get to where I wanted to be, if I kept doing this. So a few months ago I made the leap and got out of a line of work which to be honest, is the only line of work I have a strong resume for, to go back to school, try to build a business I can make a living on and really stretch those muscles I haven’t used in a long time. I’m building up the me I actually want to be vs letting myself remain the person others see me as or the person it’s easier for them to categorize and utilize. It’s tough suddenly being the person who is a beginner. Who isn’t successful (yet). Who can’t just walk in and manage everything overnight. It’s tough to explain to people why I’m taking the risk. It feels like if I fail everyone will say ‘well what did you expect taking risks like that’. But I still had to do it. It was just that moment when I finally said ”***** it. Just because I’m good at something doesn’t mean I should do it. And what I’ve been doing has been making me miserable’

  • Sam Hunter says:

    This year has been one of stretching growth, but also of reflection about the things I’ve been doing to attain the growth. In the “damn proud” column I published a book, moved to PDX, and have done a good job of finding a new tribe to call friends. My business is growing, and I hit the milestone of choosing to pay someone else to do things that I’m just not that great at. I also fired a couple of clients (and had stiff chats with a couple more) when the data supported that they were costing me more than it was worth to do business with them. I’m proud that I’ve learned how to figure those things out, and equally proud for standing up for myself. The one thing I haven’t done well is nurture my own art – I’m good at pulling the creative rabbit out of the hat for business purposes, but I’m intensely horny for my own creative stuff. And I can see that I’m getting a bit wonky around the edges for not taking care of this (I’ve been too busy “doing business”). So I plan to get good at refinement for 2015 – figuring out what must be done, or delegated, or discarded. I’m not naive enough to think that every moment of every day will be bliss, but I want to be sure to note the parts of 2014 that sucked, and plan actively to not find myself repeating them!

  • Jessica Emerson says:

    I learned only recently, and am still working to keep this lesson in mind, that sometimes it’s not enough to chase after your dreams. Sometimes you gotta lasso them b*tches down and make them into reality.
    Which is just another way of saying that dreams don’t just come true, a lot of hard work and effort goes into it. However, I’m very much looking forward to the coming weeks and months and what’s in store for 2015.

  • Jennifer Hooper says:

    What I learned in 2014:

    * I learned to wrap my arms around what I want and need, rather than turn a cold shoulder to my soul work and wedge myself into a conventional life.

    * I learned that stretching myself—emotionally, physically, and spiritually—brings me extreme discomfort…followed by extreme satisfaction.

    * I learned that the pain of heartache (still) sucks, but its contrast to joy makes joy more joyful.

    * I learned to walk away from nay-sayers and surround myself with like-minded spirits…to help keep my juju flowing.

    * I learned to say thank you, each and every day.

    * I learned to (finally) say with confidence, “I am a writer.”

    <3 Jennifer

  • sonja says:

    A year of change, courage, and campy (for me!) I went to the Firefly Festival alone and camped in a tent (courage and campy)! I put in a proposal at work to go part time so that I could spend more time in my painting studio (change and courage) – the big international corp actually said yes!!! One thing I have never done is review, plan, set goals for the next year, but the idea of doing this has been composting for some time now. So that is my next short term goal – to plan a direction for 2015. I have gathered a lot of free planning strategies from you, Scott Dinsmore, Nicole Antoinette, and others (THANK YOU all!!) and plan to read and put together a plan that works for me. Change and courage, and knowing me, a little campy thrown in! This will be a living document that I create, finding what works and modifying what doesn’t. But always taking steps forward with the goal of growth, risk, and living every moment with a heart broken wide open and love flowing unconditionally. EXCITED!!!

  • Michelle says:

    Chris, that joke in your newsletter was sooooo corny. Reminds me of my dad’s Kansas cornball humor. hahahahaha!!!!

    I would say that you’re excellent at sustaining many projects over time. The blog, WDS, your books, your book tour, your world tour. Cut yourself some slack in 2015. You’re awesome. 🙂

    What did I learn in 2014. All work and no play make Michelle a very dull girl. I need to figure out a way to resurrect more space, fun, and play in my life in 2015.

    You mentioned in your recent post about reading and how it feeds your creativity. Ditto. (Powell’s is the greatest bookstore in the Universe, by the way. Well… alongside Changing Hands. 🙂 )

    And for me, I also need to carve out unstructured time for exploration and play. Michie is about to get her spark back.

    May our days be merry and bright in 2015!

  • Dr. David Powers says:

    Like you, I read a lot less this year. I hit a high of over a hundred books a few years back, and I was really proud of that, but I couldn’t remember much of what I read. So I backed off that pride I felt at the number of books and read more thoroughly to understand more.

    I read on average about 30 books a year now. As a matter of fact, I’ve been reading and rereading Antifragile for most of this year so I can really get it. It’s a deep one.

    PS…The Happiness of Pursuit was one that I read this year and certainly in my top 3!

  • Andrea says:

    I’ve learned to not have fear of success. Or mistakes.

  • Christine Westermark says:

    I’ll first say, I want to win the Powell Books gift card! I only made a small dent in my first visit at WDS 2014. I had no idea a store like that was possible. Truly amazing. What a treasure.

    My year was great and kind of bad all at the same time. There were moments of bliss and in the next I thought I was having a heart attack. I realized, this year, I can’t afford to carry the stress anymore. If for no other reason than it is simply too heavy. My Doctor may think otherwise, but I know, these things are in my control.

    I tried, so very hard, to be present and capture in my memory, moments of joy and gratitude. For the most part, I am extremely fortunate. I have the world by the tail, as my Dad used to say. I could never see that. I often forget to enjoy the journey. And then, look at that, time has whizzed by.

    And so I learn to practice. More of the good stuff. Let the bad moments slip through my fingers, blowing them away to the wind.

    I’m grateful for so many amazing things which happened this year, but what pertains to this the most would have to be WDS 2014. In particular, giving the gifts of resources to all the folks on stage. It was so kind and meant so much to the recipients. I cried along with them, for the pure joy of it.

    Keep up the amazing work! That applies to all of us!


  • Cathy says:

    I remember seeing fairly recently a kind of quote that basically “do whatever, no one else expects you to do” – so far I have done at least three things…and I’m working on the next grouping. All which have actually not been that far off the edge but all of which have made me happier.

    My summer is just getting underway, I’m in the Southern Hemisphere and I have a huge chunk of time available just for me… which is very useful when you need to achieve the “unexpected”

  • Martha says:

    I learned to take better care of my body. Which is a difficult thing for me to admit; so simple, so “duh,” and yet so hard for me to do. There’s lots of reason for that.

    And so I worked hard (and played hard) with a new body-centered therapist. I learned to slow down. I am never going to be a Zen master–I am a restless Gemini, after all. But I began to notice before I was about to blow my stack with tension. I noticed when I wasn’t going to the gym, or when I needed a walk. I noticed. And I was kinder to myself.

    I /did/ lots of stuff this year: I went to WDS for the second time–and did the yoga challenge, with great trepidation–and loved it, and it brought me back to yoga (thanks to all who were involved). I published several essays, working with an editor I adore. I was more honest with my husband. I started cooking again. Learned some code. Wrote some sketches for a play I want to write.

    But what I’m most proud of is meditating nearly every day for 10 minutes (while my coffee brews–Gemini, remember?). For having courage to continue even on the days I am uncomfortable. My words for 2015 are: cherished, consistent, and badass. Thanks for the chance to talk about this, Chris.

  • bryan danger says:

    “Unconventional Work”…well said, i love it!
    we struggle so much now to fill out forms that ask for “employment”, or when people ask “what do you do back home?”.

    I would have never thought it was possible a few years ago, but we are now living (and traveling) off our unconventional work with great help from our “creative home use plan”.

  • Geoff Hall says:

    As ever, thanks for sharing what’s working through your heart, Chris.

    I’m a writer (who doesn’t write a 1000 words a day) so my work is pared down to this one thing, because creativity isn’t a problem, it’s resources. This isn’t a unique problem, it’s something I think every artist goes through. We have the imagination, but not the resources to produce what we have created for the public domain.

    I’ve currently got three projects ready to go; a supernatural thriller novel, a film about sex trafficking and organised crime and a TV pilot that takes me into the supernatural noir genre. (Yes I’ve been busy). 2014 was supposed to be about realising those projects, but each in different ways has run into resource issues with publisher, investment consultants (film) and working with an Exec Producer (TV Series). In a nutshell, life got rather complicated.

    So when everything is in the doldrums what does a writer do? A friend said to me that if I was put on earth to write, then I need to “keep on writing”. And so, I’ve started another writing project, for film, because when you pare everything down, what I’m here for is what I need to do. It may seem like a lonely pursuit, but the truth is I’m never lonely, because I have lots of friends. Okay, as you’ve probably guessed, they are imaginary ones(!) but if I don’t have the resources I need to mass produce these projects, the only resource left is my imagination, and that seems boundless, unless of course the government starts taxing creatives for using it!

  • Audrey Reynolds says:

    First, thanks for sharing this series – it’s always an enjoyable read and good preparation for my own annual review (I give myself the first part of January – December is too damn busy). Thanks in part to the status quo you helped create 🙂 I quit my job in Dec 2013 and spent the first 4 months of 2014 traveling and seeking rejuvenation. This summer, I switched work modes to be an independent contractor/consultant, with the goal of allowing me to travel more. Frustratingly, despite all the amazing experiences and insights I had to share, I didn’t update my blog once. Needless to say, establishing a daily writing practice and posting regularly is on my 2015 short list.

    Chris, this comment really struck me (because I can relate): “I’m pretty good at starting. I’m pretty good at delving into problems and finding interesting solutions. But as I discover over and over, I’m just really not good at sustaining the same project over time. For some reason, I always hit a ceiling of success. I don’t really know why.” Do you, like me and many in our community, identify as a multi-passionate or “scanner”, as Barbara Sher calls us? This year I read her book called Refuse to Choose and found it has some excellent tools for recognizing if you are a scanner and working with our unique gifts and shortcomings. For me, this self-awareness directly correlated to “more units of joy” because by learning what makes me tick – which parts of projects and life make me happiest. I’ve started to consciously structure things so I don’t get stuck down in the icky boring phase >> this raises my joy factor. I did a pretty good job for my first pass last fall and for 2015 I am actively focused on tweaking it. Onward and upward in 2015!

  • Cole Enabnit says:

    Great insights! It seems a main theme of your work is consistent application to the craft–whatever the craft may be. This is something I will really try to embrace in my law practice. So often, I get caught up with a particular set of issues for a particular client, I stop studying and improving in some of the more theoretical (but overarching) aspects of the law. Thanks!

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