A Tale of Two Years: The Struggle Between Freelancing and Entrepreneurship

My 2018 year in Review

It was the best of times, it was the worst of times. It was the year of personal growth, and it was the year of personal stagnation.

It was a great year for personal projects. Place Card Me—my SaaS product for making  — grew steadily, and made revenue that meaningfully contributed to my annual income and earned me a solid hourly wage. And it was a terrible year for personal projects. I built nothing new, learned very little, and my one big new product idea barely got off the ground.

It was a year of abundance. I had more work opportunities than I knew what to do with. I had job offers up the wazoo. I greatly surpassed my annual income goal. And it was a year scarcity. I barely had any time, headspace, or energy to make significant progress on any large, open-ended goals. Time came at a premium all year.

This is the tale of two 2018s. A great year and a disappointing year. Mashed together, rolled up into a ball, and impossible to disentangle from each other. Let’s get into it.

How I spent my time

“The true currency of life is time, not money, and we’ve all got a limited stock of that.” — Robert Harris

People like to think of themselves as having principles; priorities; things that define us which are intrinsic to who we are. And we do. But the only real manifestation of those principles is how we choose to spend our time. Everything else is just talk. So for me, understanding where my time went last year is the first and best place to start with in understanding the year itself. Here’s how that looks:

My professional time breakdown in 2018 The first thing that’s notable here is that of the ~1,600 hours of “work” I did this year, more than 70% of those — about 1,130 — were spent working for (my “day job”) or doing freelance work.

Of the remaining 30% I spent on personal projects, about a quarter went to Place Card Me and the remaining three quarters went to everything else — a bucket that includes writing and all of my other side projects.

By comparison, let’s take a look at the same data for the previous year:

My professional time breakdown in 2017. Unfortunately the colors aren’t the same as the 2018 graph. It’s almost completely flipped! In 2017, 65% of my time went to Place Card Me and personal projects, and only 35% went to Dimagi and freelancing.

Thus, emerges the first theme of the year: In 2018 I prioritized working for other people much more than working for myself.

Why did I prioritize working for others?

So, I spent 70% of my time last year working for other people. Surely that must have been a deliberate decision, right? Right?!?

Well, it wasn’t exactly something I sat down and sought out at the beginning of the year, but surely each individual moment was a result of some sort of mental arithmetic in my head. So why did I work for others so much?

Reason #1: Money, money, money

It turns out that a person literally handing you $100 bills in exchange for an hour of your time is pretty hard to resist.

I’m going to be honest — 2017 was stressful.

For several reasons, but one of the biggest was that feeling every month of not earning any money. Even though — thanks in large part to my wife who was supporting us — I was never close to running out of cash, it was still stressful as hell to see my bank account balance going down month after month with no end in sight.

Going into 2018, one of my important goals was to make sure that I didn’t put us in that position again. I would earn more money than I spent.

And earning money?

Well it turns out that when you do freelance you have a very real, very tangible dollar value on every minute of your time. So when I sat there looking at my afternoon thinking “well… I could spend 2 hours working on that blog post, or I could do this freelance thing thing that will immediately put $200 in my pocket,” it was pretty compelling to take the money and run.

Reason #2: The exposure to new things

Here’s another wonderful thing about working for other people: they’ve already done a huge amount of the work.

What this means is that instead of starting a new project from scratch and having to learn every little detail yourself, you get to jump into the middle and reap the benefits of everything they’ve already invested. You come in standing on the shoulders of giants. Taking an example from last year: ever since I started flirting with entrepreneurship, I’ve been interested in learning more about the Silicon Valley VC-funded startup scene. Now, if I wanted to get that exposure on my own I might quit my job, find a cofounder, pitch to VC’s, raise money, build a product, do sales, etc. etc. It could take years!

After spending a couple weeks working for a startup in in San Francisco I can say that watching the TV show is also a surprisingly good proxy for understanding Silicon Valley life. On the other hand, if I do a two-week freelance engagement at a friend’s startup in San Francisco who has already gone through all of those steps I can get a pretty good slice of Silicon Valley with virtually zero additional effort! Plus, I help out a friend and learn some new tech. So that’s exactly what I did. Want to understand the startup scene in South Africa? Work for a South African startup! Want to learn about data warehousing? Find a data warehousing gig! All of these things happened to me in 2018 and there’s no way I could have gotten those experiences on my own.

In reality, the causality ran the other way. That is, the opportunity first presented itself to me and the exposure became a reason to take it. But still, freelancing has been a great way to see different organizations and grow my technical chops, while helping out other people on great projects and getting paid to boot. Everybody wins!

Reason #3: It kept me from facing my entrepreneurial fear

2017 was one of the most pivotal years of my life.

That said, on a day-to-day basis, I spent most of the year operating in various states of pure terror and self-doubt. Fear of quitting my job and losing my identity. Fear of putting myself out there by writing publicly. Fear of launching a product that was dumb and completely failing at my already-kind-of-pathetic goal of making at least $1 on the internet. Every step of the way was a) terrifying and b) caused me deep, deep self-doubt and anxiety — though I did try to hide it as best I could.

Looking back, the fact that I was terrified all the time is central to what made 2017 a pivotal year. I was doing things that were truly new. Putting myself out there in ways I never had before. And really challenging myself on my own terms and with my own agenda.

“Don’t do what you want. Do what you don’t want. Do what you’re trained not to want. Do the things that scare you the most.”  — Chuck Palahniuk

In 2018? Honestly, I did very little this year that terrified me, thanks in large part, to freelancing.

Sure, I did plenty of freelance work that was hard, but the level of personal stake and sense of self-worth weren’t tied to that work in the way they are with my own projects. I knew that I wouldn’t fail with my part, and if the project as a whole failed? Well, that was someone else’s problem to deal with.

In short, it was safe. And choosing safe over scary is pretty easy.

Working for others became the easy choice.

So what did I lose by prioritizing working for others?

So we now see how the allure of working for others led to it being a priority — conscious or not — for 2018. What was the cost?

The short answer is that my personal projects languished. Big time.

All that time I spent working for others? That was time that could no longer go towards pushing out new personal projects, writing, etc. And not just the time but the headspace — that elusive energy necessary to do meaningful work. So, while it was pretty easy to continue to add small features to Place Card Me and other existing projects, it was much more difficult to find the time and space necessary for a thoughtful blog post or for launching a brand new thing.

Yes, Place Card Me had a great year and I’ll talk about that more in a bit, but everything else I’ve worked on has been a real struggle. Here’s a quick run down:

Chat Stats: A I launched in late 2017 actually became my second monetized product. I made a small push to add a paid tier in April and then did nothing to improve or promote it for the rest of the year. This has resulted in completely flat and uninspiring revenue of about $80/month.

Chat Stats monthly revenue from April-December was basically a flat line around $80. : Expected to be one of my big efforts for 2018, I was going to create an awesome Django resource on the internet and then figure out a way to make money from it. It’s been almost a complete failure, consisting of a single blog post around an open-source library that I created, and — until the last few weeks — literally nothing else.

Photos New Tab: I added a sad little “buy me a coffee” link to my in hopes of getting some donations (which — incidentally, no one has ever used). More recently I added a few small product improvements, but overall have done basically zero to promote or do more with the extension despite a modest, growing, and happy user base.

: On my personal blog I wrote four blog posts this year (five if you count this one) compared to twenty-four last year. I’m not all that proud of any of them, nor did any of them really get any broader traction beyond the audience I built last year. Even worse, I feel like I’ve completely forgotten how to write well and feel embarrassed and insecure about everything I produce now. Possibly for good reason?

Beyond that, and most depressingly, I didn’t create a single new product of note for the entire year. Build With Django is the closest thing to a new project and it’s a glorified blog with two posts. Compare that to last year when I arguably launched six different things (seven if you count this website) and it’s a huge let down.

But don’t worry — it’s not all doom and gloom! This now brings us to the fun part of the year.

The magical upsides of building products

Remember those time wheels at the beginning of this post? If you were looking closely, you might have noticed that I spent almost three times as many hours on Place Card Me in 2017 (283) than I did in 2018 (102).

However, because it’s a product those hours are not directly correlated with earnings at all (as opposed to working for others which is obviously almost 1:1).

This decoupling of effort from money — also known as the mythical passive income stream — results in some pretty magical behavior over time. In fact, when all’s said and done in 2018, Place Card Me will have out-earned itself by more than 10x from last year despite the reduced time investment. Here’s the monthly revenue for the entire history of the site.

Revenue from from its launch through 2018. Data as of December 26, 2018. From the . Here are some other fun figures about Place Card Me for comparison:

[1] As of December 26, 2018 To summarize, in 2018, I was able to continually improve the product and increase revenue while working a totally manageable amount of hours and getting paid a solid wage on-par with my freelance rate! And it’s not just the revenue that compounds on itself. Although the product today is largely the same as it was 12 months ago, I’ve made tons of small improvements throughout the year: tripling the number of place card templates, adding support for different card layouts and paper formats, improving the UX of card making and fixing a whole bunch of bugs. I also experimented and tested my pricing constantly, eventually landing on a pricing model that seems to be working well.

What’s wonderful about all that is that the effects of the changes are additive and permanent. The site is always getting better, and once it does it is better forever.

Achieving entrepreneurial success in spite of myself

When I look back on 2018, I suspect I’ll think of it as the year I tried to juggle freelancing and entrepreneurship and failed. And yet somehow succeeded in entrepreneurship anyways. From a freelancing perspective 2018 was a success by any metric. I helped more people, worked more hours, earned more dollars, and learned more than I ever thought I would. From an entrepreneurship perspective 2018 is more complicated.

On the surface of everything it looks great. I made almost $13,000 from not one but two online products, despite not trying too hard on them. That sounds amazing, right?!

In reality, I think I achieved this success in spite of my efforts, not because of them. This year, I largely rode the coattails of the work I did in 2017, and that momentum carried me into a good place. But I don’t expect it to hold.

Already copycats for Place Card Me — apparently inspired by that sweet $1,500/month — are springing up out of the woodwork. Meanwhile, I’ve exhausted all the easy ideas I had in mind to increase revenue. So looking to 2019, unless I come up with something new to do, revenue will stay flat or possibly even drop if I start losing sales to competition. And now — unlike 2018 — I don’t have a new project ready to start pouring gasoline on to fill the gap. Essentially, I’ve burned through all my 2017 capital reserves and failed to make any new ones. What does that mean? I think it might mean that 2018 was a fluke. And if I want to succeed at this whole passive income/entrepreneurship thing I’m going to have to expect to work quite a lot harder on it moving forwards.

So what’s in store for next year?

The theme for next year — I hope — will be reinvesting in personal projects.

My primary goal/plan for the year is to have a 50/50 split of my time between working for others and working for myself. I figure if time is the only true currency then all I have to do is spend mine properly and I can figure out how to sort out the rest. Practically, that should lead to a few major consequences. Less time freelancing. Substantially less income generated — unless I manage to overachieve on the product side. More uncertainty. More fear. More investment in myself. More at stake to lose. Should be a fun year!

Appendix: My 2018 Goal Report Card and 2019 Goals

In my beginning-of-the-year post, I set four high-level goals for 2018. Now that the year’s over I thought it would be fun to see how I did. Here’s my self-graded report card:

Explanations for the grades follow.

Diversity: Have at least one more project generating some passive income

Grade: B.

I did succeed in generating passive income from a second project. As I mentioned,  — my GroupMe chat analytics platform for narcissistic millennials — has earned $770 or about $80 / month since I added a paid tier in April. I gave myself a “B” instead of an “A” despite hitting the goal because I kind of feel like I cheated. I had already built out about 80% of the functionality of the site by the end of last year and I basically just added one new feature and a paid tier and — voila! — a few dollars started trickling in.

The intention of the goal was that the diversity would come from a new product, and I had hoped it would be a substantial proportion of my passive income, but this was neither.

Growth: Get to $20k total or $2k monthly passive income by December

Grade: A-

Again, I hit the goal — specifically the “or $2k monthly” part of it, with Place Card Me passing $2k in November and December this year. I’m giving myself an A- instead of an A because it’s a seasonal product and I don’t think I will hit $2k/month consistently, just once or twice during the year. I’m still excited about this revenue, obviously — and I hope that I’ll be able to pass $20k next year — but I wouldn’t feel right not giving myself a small ding on this one.

Sustainability: Make $80k of total income (including salary/freelance work)

Grade: A

I set my target at $80k of income for the year and I substantially beat that due to the aforementioned increase in freelance earnings! At the end of the day I expect my 2018 income to be right around $100k, with about 40% of that coming from Dimagi, 50% coming from freelancing, and 10% coming from my own products. From a sustainability perspective, I could live off of this level of income indefinitely! Hooray.

Dynamism: Continue to reflect and iterate on my life regularly

Grade: C

The poorly-worded, and impossible-to-measure goal here was “continue to reflect and iterate on my life regularly”. And while I did do some reflection — including a quick bout where I  — I really didn’t do a whole lot to make any major sweeping changes in my life the way that I did last year.

My life at the beginning of the year was a mix of Dimagi, freelancing, and side projects, and at the end of the year it is basically the same (including the same side projects).

So was this because I didn’t need a change or because I wasn’t open-minded and reflective enough to accept change? I’m not sure, and that’s why I’m giving myself a C. Regardless, I hope that this end of year reflection will result in a substantially new course, and I feel it at least partially meets the intention behind this goal.

My 2019 Goals

And finally, here are my goals for 2019:

1. Commitment: Achieve a 50/50 time split in working for myself vs working for others
2. Financial Growth: Earn $30k income from personal projects
3. Diversity: Make at least one sale of my new project: a
4. Personal Growth: Do more things that scare me

These hopefully fall naturally out of the above and don’t require a whole lot of explanation.

I’m also asking myself a lot of questions about 2019, including how best to prioritize my time between growing Place Card Me versus continuing to create new things, how much I should be writing (and what value I get from it), as well as what I should be cutting out of my life.

I don’t know the answers yet, but it’s nice to have the questions bouncing around in the back of my brain. That’s it! If you made it this far, bless you and thanks for your persistence. Happy 2019!

Our first Christmas as a family. December 24, 2018. Lion’s Head, Cape Town. — Cory (and Rowena and Lockwood)

Originally published at .