2013 Annual Review: Lessons in Independent Work

Annual Review-Work Lessons

Hi, everyone—the 2013 Annual Review continues! All posts will be open for comments from readers.

In this post: a few thoughts on the world of work.


On general struggles.

As mentioned in the first post on looking back, I had a few general disappointments that overshadowed much of the year.

I know I’m my worst critic, but isn’t that how it’s supposed to be? We should always be looking within, questioning our failures and seeking to improve. I have a restless heart and I’m disenchanted with slow progress.

These days I’m working on things that are built in stages. I’ve experienced a shift in “just get things out of the door” toward projects that require more time, in some cases multi-year efforts. The outcomes aren’t always apparent from the outside, and the fix isn’t always a quick one.

It’s not all bad—the business actually grew during this time. I’ll regroup, as I always do, and make a better plan for 2014.

Lesson: Move on and get back to work!

On starting projects and not scaling well (a recurring theme).

One of my challenges is that I start projects that are fairly ambitious. I charge ahead and work non-stop during the creation stage. I’m still excited to get them started, but then I want to start something else.

Since most of my projects are successful, it’s not a terrible problem to have. Everything works and is fine. But it does create the question of scale.

I hope to fix this tendency, or at least continue to improve it. But mostly, I plan to keep doing. I’m very motivated by making things and have no plans to stop.

Lesson: Fix it or live with it.

On having multiple careers.

At this stage in my career, I could make a living entirely from writing books or entirely from creating small business projects—but I like both activities and don’t want to choose. I don’t have to create new Unconventional Guides or invest in side projects or host additional events. I do these things because I like to, not because I have to.

I like the security of earning income from multiple sources, and I like the ability to mix it up by doing different kinds of work.

Lesson: Stick with the diversification as long as it continues to feel right.

On writing… that thing I’m supposed to do.

Long ago I began the habit of writing 1,000 words a day, a practice that others have adopted and adapted in their own way. It’s good that others have taken it on, but I’ve somewhat fallen behind.

I believe in maintaining a balance of writing and other kinds of work, but this year I think I shifted too far toward the other kinds of work.

Lesson: A writer writes. I want to get back to writing more, so I’ll work to create structure that supports a regular writing practice.

On events (producing and hosting them).

WDS 2013 was fantastic! I feel very fortunate to be part of this gathering. We’ll be doing it again next year and I’m just as excited about it.

When something’s going well, it’s good to ask yourself if there’s any logical extension or addition to it. Every year we spend many months leading up to a global event that lasts less than a week. Inevitably, we learn a lot of lessons each time—how to facilitate engagement with thousands of people, how to balance official activities and independent meetups, how to work with the city, and so on.

But then, after working so hard and learning so much, we have to wait an entire year to do it again. Starting up with a new event, Pioneer Nation, allows our team to work together more cohesively throughout the year.

Of course, that’s not the main reason we decided to create another production that will require hundreds of hours of work. We’re doing it because there’s a clear need for education and community among independent entrepreneurs, and we think we can meet this need.

Lesson: Continuing serving attendees through WDS, and launch the new event well.

On events (traveling to them).

I had fun speaking at various events, organizations, and companies, including SXSW, LeWeb, Frequent Traveler University, Facebook, and a dozen or so $100 Startup stops that were facilitated by reader co-hosts.

Without question, the best part is always meeting with readers and seeing them connect with others. Most of the events and commitments were in the first half of the year. In the second half, I focused on writing a new book and rebuilding the business.

Lesson: Host more meetups! Fortunately, we’ll solve this in 2014 with … 30+ events after my new book comes out.


Legacy can’t just be what we do, it has to be what remains after everything that is temporary fades away. I’m trying to make sure the side projects I take on matter, or at the very least that they don’t take all my attention.

It’s been a strange year overall, but I won’t lose heart. I’ll regroup and be more strategic next year—wait and see. Onwards!

What about you—what did you learn or experience in your work this year?

Feel free to share your own lessons or comments with other readers.


2013 Annual Review: Introduction & Invitation
2013 Annual Review: Looking Back
2013 Annual Review: Travel Roundup

*We’ll be publishing a roundup post of reader blogs before the end of the year. Link to any of the 2013 Annual Review posts, and we’ll share a selection at the end.

Image: Paloetic

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  • Robin Raindropcatcher says:

    2013 was very strage to me too. Ironically, I had started the year off with an illustration of a phoenix and the words ‘ashes to ashes’. That was mainly due to the break up with my ex. I wanted to see it as something like a new start. Now, I’m getting the feeling I had to burn all year to find new birth in 2014.

    Basically, the business I had grown to support my lifestyle full time collapsed after a few months, due to some changes one of my partners made in our contract. Sadly this happened shortly after I settled down after years of travelling, leaving me in a dream flat that’somewhat unaffordable now. Which fires my wanderlust again. So I feel a bit like I was in a golden cage.

    But three months ago, I started a new project. The first big step of it will be done by new year to bring in the cash again. Also, I’ve met my ex again after months and it seem as if I’ve come over the whole thing finally.

    It all looks like 2014 will be the year of my rising from the ashes 🙂

  • Michelle C says:

    Because we’re currently serving with Peace Corps, my husband and I are somewhat limited in our work to the job descriptions we committed to. It’s been worth it to be able to integrate into a Jamaican community that we’d otherwise never have the chance to experience, but it does feel like we’re in a holding pattern for the time being.

    Next year, as we wrap up our term of service, we’re looking forward to branching out and pursuing more variety as well as location independent work.

    I have a similar tendency as you, Chris, in terms of really enjoying the planning and creation phase of projects, but then wanting to move on to something else. I applaud you for what you HAVE finished and the level of quality and value you’ve been able to achieve across the various projects I’ve seen. It’s a motivation to your readers to follow suit.

  • Beth H says:

    I just returned from two years working in South India. I now have a new bi-coastal marriage and figured out that I can’t really get ahead in India making Indian wages (I was hired as a resident of India)…long story.

    Anyway, after my kids left the house for college, I took off to do what I like to do best, travel and live abroad. I also did a Peace Corps stint in East Africa in the 1980’s. I have been scribbling away at a book idea but wonder if anyone really wants to read another “Eat, Pray, Love’ type of book and it feels a bit, “Look at Me, Ain’t I Great?” so I have been wondering how to proceed. I have had to take work in cubicle-land for the time being to get some money saved up. I’ll be back in India with my husband during the month of Feb. Yes, 2013 was a wacky year for me. It is nice being home with my family in Boulder, CO for the holidays though…never thought I’d be saying that 🙂

    Thanks for the inspiration your site brings to me and many others!

  • Pernille Norregaard says:

    2013 have been a great year in many ways, but like you I haven’t spent enough time writing. I have made up for it in the past couple of months, and 2014 will be all about the writing.

    2014 will also be the year where I do my first really long trip. I’ve already visited 60+ countries, but next year I’ll do a slow trip (11 months) around the world, so I have time to soak in the culture of the places I visit.

  • Martin says:

    I learned this in your book and even much more so during the year that you have to make money. If your business doesn’t make money, it is just a hobby. Who wants another hobby?

    You have to find a way to make money and execute it ruthlessly.

  • Mitch says:

    Hey Chris! I saw this on Eben Pagan’s FB page today, I thought it might provide insight into your struggle of starting projects and not scaling well.

    “A key to Entrepreneurial Productivity is an important mindset shift. Growing up we learn the laws of cause and effect, Newton and all that. But then we get into the job world and we get programmed through habit that when we show up and do our work, we get a paycheck. We learn the mindset “Do work = get paid.”

    But the way to achieve huge success is to shift from focusing on work, to focus on results. That’s how you get more success. Then to go to the next level, we stop focusing on results and start focusing on creating value. And then we refine our focus even more and only spend our energy on the thing that makes the MOST possible value, and focus on that for a long period time.

    It’s important that Entrepreneurs don’t have the mindset of “working for a pay check” -they’re playing a bigger game. They’re focused on creating massive results and massive value, as measured by the customer.”
    – Eben Pagan

  • Kathleen Pedersen says:

    A big lesson for me was that having multiple careers was possible for me. It always seemed like focusing on one traditional job was the safest bet. Now diversifying income seems like the more prudent approach. And even better – it’s a lot more fun, too. I’m really excited to see what that takes me next year!

  • Katherine says:

    On the recurring theme of project scaling. Maybe you just need to team up with a finisher, since you are a starter and love to get things going on the initial stages why not find someone who is just as enthusiastic about seeing projects through to completion. So, take a load off, it may mean letting go of some control and not always knowing if the finished product will be as you envisioned, but it rarely is, sometimes it’s even better 😉

  • Fraser says:

    This year has been very different from any other so far in almost every way. I quit a well paid job in July, launched a new blog and began cycling round the world at the start of August.

    My work now is to write about the journey and the lessons I learn about the world around me, and within me. It’s a four year project and the ultimate goal is to raise enough money to build a school through the charity Room to Read.

    I also aim to create an income from writing books and creating courses to sell through my blog.

    So far I’ve cycled over 4000 miles (just another 36, 000 to go!) and started to write my first book which will be released on or before February 16th 2014 – no pressure. …

    My next post, due out next week, will link to your end of year review.

    Thanks for sharing Chris, have a great holiday season.


  • Lucy Chen says:

    2013 was an important year for me. I learned to paint with oil and found my “style”.

  • Susanne Hansen says:

    2013 has been a crazy year for me. I jumped into my creative business ventures (writing. blogging,photography) full time this past summer. Sink or swim mentality. I started too many things and completed few which leaves me somewhat doubtful how 2014 will start off. But in terms of finding my courage and my voice – 2013 was it!!

  • Deb Southworth says:

    2013 I learned to play the ukulele. I now have a YouTube channel and have posted 2 videos. I have another planned for Valentine’s Day. The character playing is one I created when I taught school. Here is the link to my channel:

    It is called Maude’s Music. It will bring a smile to your day.

  • Edmond Taylor says:

    My main problem is that I start quite ambitious projects, but I don’t finish the job, I quickly burn out

  • David Young says:

    When I’m planning goals and new results for my projects, I always try to set them globally. But then when I review and reread the results, I understand that I could have squeezed out much more! And all because priorities can change even in a short time.

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