“You know, when I look back on the story of my life I wonder whether 2017 will end up being the year that everything changed.”
—me to my wife, December 26, 2017
One hobby I developed in 2017 was taking pictures of myself looking out over grand vistas to incorporate into my blog.
Drakensberg, South Africa, September, 2017.
It’s funny the things that feel important.
In 2015 I moved to Africa. In 2016 I got married.
You’d think those would be big, transformative experiences,
and yet I’m pretty sure that in the story of my life, 2017 will outstrip them all by a long shot.
The most succinctly I can say it is that while every year till now has been marked
by changes in events, 2017 felt like the first time in my adult life I developed a completely new perspective.
In 2017 I ended up doing a whole mix of things. I left my job. I started a blog.
I built and launched a bunch of projects. I learned to surf. I hiked. I traveled.
I started freelancing.
Eventually, I ended up back almost exactly where I started.
Only everything is different now.
This post is about that journey of perspective change—a journey of slowing down, discovering purpose, and searching for happiness.
Hopefully by the end it will be clear why I feel this was the most important year of my adult life.
But to get to there we have to start from the beginning.
The year I realized something was wrong (January)
A year ago today I was working as CTO of Dimagi, a title I had held for the previous ten years running.
I was working 60-hour weeks regularly, attempting to run a 30-person technology team, lead the coding and architecture of
CommCare HQ, and keep some of our biggest projects from redlining—all at the same time.
I was deeply invested in the work—tying up a lot of my own personal and professional identity in the success
of Dimagi and my own contributions to the organization.
I was also stressed out, burnt out, and probably not that fun to be around most of the time.
Sensing something was amiss, I decided to take a sabbatical from Dimagi starting in March.
I would give myself six months, during which I would… figure it out.
Figure what out, exactly?
At the time I wasn’t sure. I just had the sense that there was something that needed to be figured out,
since I wasn’t feeling particularly happy or positive by my work anymore.
In that exact moment it was hard to see past the burning fires still in front of me and plan out that future.
I hoped that once I had the time and space to escape the pressures in front of me things would become more clear.
The year I took a break (March)
More than anything, 2017 will be defined by my sabbatical. For the very first time in my career, I decided to take a break.
The first two weeks of the sabbatical were a gloriously disconnected vacation.
Traveling without computers, my wife and I took a late honeymoon to Mauritius and Mozambique.
We dived with manta rays, swam with dolphins, climbed mountains, and ate our faces off.
Trying on relaxation for size. Bazaruto, Mozambique, March, 2017.
Between activities I spent a lot of time staring into the blank pages of a new notebook and trying to figure
out what the hell I was going to do with the next six months.
It was scary, freeing and fun. I had literally no responsibilities,
and found that the absence of responsibility created a deliberateness of purpose.
Gone was the daily grind of checking email and fighting fires, and in its place was planted
a seed of a question that started growing within me.
What did I want to do with my life?
This question, despite it being the most obvious, most core, most cliche of questions,
was something I hadn’t really thought about in years.
It’s a hard question to care about in the middle of the daily grind.
I didn’t get to an answer, but that feeling stuck with me, and became a lesson that would carry me through to the rest of the year.
Space is important. Rest is important. Big, hard questions are important.
I decided that disconnecting was an important way to get to insights previously out of reach and resolved that slowing down
would be a major priority moving forwards.
I also had a mission: figure out my life. Easy, right?
The year I decided to try solopreneurship (March)
I came back from that two-week vacation feeling both inspired and disoriented at the same time.
Inspired by the idea of choosing my own fate; disoriented by the vastness of choices in front of me. I needed focus.
I knew I wanted something slower and less stressful than what I’d been doing before.
I wanted something that had the possibility of providing me enough income to live on, and enough freedom to
set my own terms, hours, and responsibilities.
That was when I came up with the idea of pursuing solopreneurship—a
very specific type of entrepreneurship focused around staying small (one person-sized, to be precise).
It’s a subset of bootstrapping that appealed to me because after running a large team for so
long I had no interest in having employees or even collaborators.
I wanted to do this thing on my own—with all of the autonomy, freedom, and accountability that came with that.
I didn’t need a billion dollar exit, just enough money to keep a roof over my head and food in my belly while
I enjoyed the flexibility of no longer having earnings tied to hours worked.
At least that was the plan.
So I decided to give myself the six months to build something that was passively generating income.
It wasn’t the loftiest of goals, but I had no idea what I was doing and so I set my targets low.
I really just wanted to earn a single dollar in six months.
The year I made myself get comfortable in public (March)
If you didn’t know me before 2017 you might be surprised to learn that I am historically a pretty private person—one
who, prior to 2017, had almost no presence online.
Prior to the sabbatical starting, my previous tweet was from November, 2013.
In the three years since joining Instagram in 2014, I’d posted exactly six times.
My website at the time was literally a single page that said “This place is a barren wasteland”.
This is the entirety of my personal website from 2012-2017.
The word “currently” contains five years of failed optimism.
So why did that change?
The motivation for working in public started as a result of the desire to pursue solopreneurship.
You see, once I’d decided on this solopreneur thing, I started consuming lots of advice on
places like Indie Hackers about how to get started.
One of the first things I read was from Nathan Barry, who had the following advice:
build an audience first, and then figure out what you want to sell to them.
Since I had no idea what I wanted to sell, this sounded perfect. I’d just start with the whole audience thing.
Unfortunately, that meant putting myself out there.
So, I made my very first project my own website.
I would use it to establish my own little corner of the internet, and I’d build an audience by blogging
about whatever it was I was doing. I would do this until I figured out what I actually wanted to make and sell.
The website launched much as it is today at the end of my first sabbatical week,
and shortly thereafter I published my first post about the solopreneur idea itself.
My very first attempt at audience building on Indie Hackers.
The year I realized I can create things of value (April)
I’ve mostly documented my journey this year with Place Card Me—an online place card maker,
and the project I invested the most time in over the course of my sabbatical.
However, the first product I launched back in April was Chimp List Helper—a
tiny tool to help manage pending subscribers in MailChimp.
I made it to solve a problem I had: people signing up for my newsletter but never confirming their email addresses.
After Googling around and realizing there wasn’t a better solution out there, I decided to make the tool public
and post it in a few places.
After this, I very quickly saw a slow trickle of people successfully using the tool,
and over time I started getting some positive feedback from people who found and used it successfully.
A few of the adoring Chimp List Helper fans. Source: this Facebook thread.
About 20,000 email addresses have been subscribed since its launch in April.
This small step was super motivating!
It made me realize that despite how saturated and crowded the internet is today,
there were still small things I could build that would solve people’s problems better than anything else out there.
This gave me the confidence to believe that if I just came up with something worth
building that I’d be able to add real value to the world.
The year I became the “place card guy” (May)
I would be remiss if I didn’t talk about place cards at least a tiny bit in this post.
May marked the initial launch of my place cards MVP and the first people successfully using Place Card Me!
It also marked the beginning of my online identity becoming more and more tied up in place cards, for better or for worse.
The most ironic thing about building a product for the wedding industry was how little I knew about it.
I ended up embracing my ignorance and it worked out okay.
The year I remembered I love writing
In high school and college I dreamed about becoming a writer.
However, coming from a family of engineers and having a penchant for math and science it never felt very practical.
By the time I’d graduated from university with a CS degree it seemed my path had been chosen,
and as I got into software development I found product-building and engineering to be a similar creative outlet for my energy.
Still I enjoyed writing, it just mostly took the form of emails, speeches, and the like.
Remember that whole “audience building” plan?
Well it turns out for that to work you have to build a product that relates to your audience.
In my case I ended up making a product for the wedding industry and writing about becoming an indie hacker/solopreneur,
which didn’t really work. At all.
Still, publishing things on the internet regularly had a major side-effect: it rekindled my interest in writing in a big way.
The idea that I could actually attract the attention of people on the internet was such a magical concept.
A person on the other side of the world thought that this thing I wrote down was valuable enough to give me their time and
attention—and sometimes even respond! That’s amazing.
At the outset, riddled with insecurity and self-doubt, I never really felt like I would produce anything of actual value,
and so the fact that even a modest amount of people engaged with it was super motivating.
This created a positive feedback loop of writing and publishing that motivates me to this day.
Stats for my ten most-read stories on Medium.
In total I’ve probably had around 12,000 story-reads, which is a modest but motivating enough number to keep at it.
The year I got my memories back (June)
In June, feeling like I might have chosen poorly with the whole place cards idea,
I decided to take some time and build something else, mostly for myself.
The result was Photos New Tab—a Chrome extension to show you photos from your
Google account in your new browser tabs. The result?
I now get to see the pictures I’ve taken throughout the course of my day.
To embrace an ongoing goal I had of getting outside my own comfort zone, I also did something scary and
published myself on YouTube to try and promote it.
Me awkwardly attempting to talk up my chrome extension.
Like most of my projects, Photos New Tab got modest traction, showing about 180,000 photos to 375 active users
since its launch in June.
The year I figured out there are many paths (July)
At around the midpoint of my sabbatical I started getting a little nervous.
I hadn’t made any money from any of my products and it didn’t look like I was going to any time soon.
I came to the realization that there was no way that I’d be “successful” as a solopreneur by the time my six-month window was up.
This made me think about what really goes into a career,
and I was able to boil my needs down to basically two simple requirements.
I needed to make money, and I wanted to enjoy what I did.
Attempting to model my future career. July, 2017.
This opened up my mind to to an entirely different future—one where I could design my life from scratch
in a way to meet these requirements.
I realized that income was going to be the first requirement I needed to solve,
and so started figuring out whether I could generate income via freelancing—and also whether I liked it.
I also started thinking seriously about the types of attributes I wanted from my future career,
and how I might be able to find work that fit the bill.
In the second half of the year I would manage to land gigs from five different freelance clients and earn over $32K
in freelance software development, proving to myself that it would be a totally viable future, if I wanted it.
The year I started taking care of myself
The number one goal of my sabbatical was to try and figure out the elusive quest for happiness.
And while a lot of that effort ended up getting directed professionally, a second huge component was my health and psyche.
I realized pretty quickly I felt better whenever I did the following two things:
- Get outside
- Do something active
So with this knowledge in mind I set a goal of doing something outside and active five times a week.
Thankfully Cape Town is a place that makes this goal as easy as possible.
I took up surfing, bought a book of hikes all around me,
and ran in the hills around my home regularly.
The iconic Table Mountain from Wally’s Cave on Lion’s Head. Cape Town, South Africa, August, 2017.
I wasn’t completely successful in hitting five times a week (I ended up averaging about 4.7),
but I was successful in feeling healthier—physically and mentally—than I ever have before.
The year I got my priorities in order (July)
In late May my father checked himself into a hospital in Taiwan because he was nervous about his heart.
By June it became clear that something was wrong and a major intervention would be necessary.
I live a long way from my parents—7,723 miles to be exact. But I decided to go home for the surgery.
The result was what ended up being one of the best experiences of the year:
an opportunity to live with my parents for over a month while my dad prepared for, underwent,
and recovered from what ended up being a wildly successful heart surgery.
The opportunity to spend more time with my dad, support my mom, and ultimately be there while fear,
emotions and tensions were running high ended up feeling like the most important moment of the year.
Driving my parents home from the hospital post-my father’s quintuple bypass. Boston, USA, July 2017.
I attribute the fact that I was there at all almost entirely to the sabbatical.
In another world, the goings-on at home for what doctors were calling a “routine heart surgery”—which sounds a lot like an
oxymoron—might have felt far away and inconvenient in the face of a mountain of work.
In reality they were obviously the most important things happening in my life,
and I felt very grateful to have the time and headspace to realize that and act accordingly.
Hearing my dad mutter “piece of cake” moments after a breathing tube was removed from his mouth post-quintuple-bypass—and
seeing my Mom’s relief and happiness—is a memory I’ll hold onto for the rest of my life.
The year I officially became an entrepreneur (August)
On August 24 I made my very first place card sale and officially became an entrepreneur!
A week later I made two more $1 sales and remember saying to my wife
“You know I think if I get lucky and keep at it, this thing could be making $100 a month in a year!”
Little did I know that it would make $100 just two months later,
and would bring in $500 by December—flirting with $1,000 in total for the year (still modest, but trending well).
Place Card Me’s usage stats and first five months of revenue, as of December 28, 2017.
Sadly, it will likely not crack $1,000 by year’s end.
The year I didn’t forget my past (October)
As the allotted time for my sabbatical drew to a close I was faced with a choice:
pursue the new freelancing/entrepreneurial journey I had started for myself, or return to Dimagi—the
place I’d invested my heart and soul into over the previous ten years.
I realized I wanted both things.
Like two sides of a coin, both were a part of me and the life I had established.
Dimagi occupying my past and yet still growing and pressing forwards to
staggering (for us) scale,
while my solopreneurial projects loomed bright in my future dreams of having fully-sustaining passive income.
If you want to do both, divide your time in half.
Thankfully I was able to sort out an arrangement with Dimagi where I was able make this happen,
and in October I returned to Dimagi part-time in with a cool new title: “Chief Accelerator”.
This new role allows me to continue giving back to the organization I helped get off the ground while
remaining independent enough to enable my other professional life.
The year I established a new normal (November)
Monday: Dimagi, make new place cards, surf, write.
Tuesday: Freelance, run, work on new side-project.
Wednesday: Hike, Dimagi, write, fix bug in chrome extension.
My days are now varied with a wide mix of different personal and professional activities.
And yet there’s consistency in the variability. Each week I work about 40 hours.
About 40% of that time goes to Dimagi, 25% goes to freelancing, and the rest goes wherever I want.
I’m also still trying to get outside five times a week.
My time split so far, post-return to Dimagi at 40%.
This “new normal” has been going on for about 10 weeks and seems to be becoming as close to a routine as I’ve had since
the sabbatical started in March.
Between my part-time Dimagi work and freelancing, I’m making about what I made when I was full time at Dimagi.
But everything else in my life is far richer.
How long will this feeling of stability last?
I’m not sure—and I think the answer is not “forever”. But for now it’s pretty great.
The year I redesigned my life (instead of letting it slide by)
2017 started with a low point, a question (“what do I want?”), and the space to find an answer.
With this space I was able to reassess my life from first principles.
What did I want? What did I need? How could I find those things?
The answers—once I started looking for them—ended up being simple.
Slow down. Keep learning. Stay active. Seek autonomy. Explore.
And above all else, be intentional about how I live my life.
2017 by the numbers
That’s it for this post! For fun, I thought I’d throw up a few quick numbers from my 2017.
Hours worked on
Place Card Me
Hours spent running / surfing / hiking
from Place Card Me
from all other projects