The Master Plan

My 2019 year in review

This is the third installment of my “year in review” series. For a recap, here’s 2018 and 2017.

In the story of my life, 2019 might be the year I found my footing—the year I solidified my path and started walking it. Maybe even the year that laid the groundwork for the rest of my life.

It’s all part of a master plan that’s been brewing in the back of my mind for the last several years—written down for the first time below.

But before getting into the master plan, I want to take a moment to look back on the year past.

2019 Recap

What Got Done

Above all else, 2019 was the year of Pegasus—my Django SaaS boilerplate project.

I spent the overwhelming majority of my “personal project” time working on it, especially in the first half of the year leading up to its launch.

Pegasus Hours by Month in 2019

Pegasus hours by month. The official launch happened June 28, 2019.

Pegasus was my top priority for the year—the thing that if everything else failed I wanted to make sure happened.

And it did!

I had a moderately successful launch followed by a steady stream of customers through the second half of the year. And it feels like just the beginning in terms of the project’s potential—something I’ll talk about more later.

Other accomplishments from the year:

2019 Time

My high level time breakdown for the year.

Side Project Income

At the beginning of the year I set a goal of hitting $30k income from personal projects. The reality was closer to $26k.

Still, I’m not complaining about this!

Here are the details by project:

Project Profit Change from 2018 Hourly Rate
Place Card Me $19,918 +81% $275
Pegasus $4,126 +% $17
Chat Stats $1,747 +140% $235
Total $25,791 +120% $75

Income and other details by project. Note this is profit, with expenses and Stripe fees removed.

Every product has gone in the right direction this year, with the overall income number more than doubling from last year’s totals.

And the data looks even better broken by hourly rate! $75 / hour is still substantially less than I charge for freelance gigs, but it’s definitely enough to sustain me if I can get the hours to full time. Also—as with all projects—Pegasus had a huge up front investment that is now starting to pay down dividends. (For a more visual representation of this, check out my side project dashboard.)


Here are a few key themes and takeaways that emerged from the past year.

I have less time to work than before.

Of course, I should have known I’d have less time after having a kid, but in December of last year my son Lockwood was only two months old, I was just starting to work again, and I really had no idea what “steady state” life with a baby was going to be like.

Fast-forward a year and it’s clear that I have fewer productive hours in a week—probably 1-2 less per day.

The reason is simple: the amount of child care coverage is less than the amount of time I’d previously allocated to work and self-care. After exercise, meals, etc. I’m down to about 7 productive hours a day in my new life—half of which go to my day job at Dimagi.

This means I have even less time for personal projects than I expected, which also means I have to be smarter and more efficient with the limited time I do have.

Freelancing remains a double-edged sword.

Last year I wrote extensively about the ups and downs of freelancing, and that theme carried forward this year. In the beginning of the year I was quite diligent about my “50% personal projects” 2019 goal and kept freelancing to a minimum, but after I launched Pegasus I started ramping it back up.

Freelancing Time in 2019

Hours spent freelancing by month. Observant readers might note that it’s the exact inverse of Pegasus time.

And on the one hand, it’s been a great experience. I launched a new site using Pegasus and learned a ton from the process. I helped Dimagi deliver a high-profile, mission-critical piece of functionality that probably no one else could have done on the schedule we were facing. And the extra cash never hurts.

On the other hand, it’s really sucked my time and energy away from Pegasus, Place Card Me, and my other projects. And if I look back on my personal accomplishments in the second half of the year, I’m a bit disappointed.

I stumbled into the perfect flywheel product.

This is the takeaway from the year that I’m the most excited about. And it was a complete accident.

Pegasus is the perfect flywheel product for my own goals.

What’s a flywheel product, you ask?

Well, it’s a riff on the “flywheel” business concept: a circular feedback loop in your business in which every element feeds into other elements in a virtuous growth cycle. Once you have a flywheel business you just have to get it spinning and then it grows and improves from there—almost on its own.

The most popular example of the flywheel comes from Amazon, as depicted below.

The Amazon Flywheel

The famous Amazon flywheel, where each factor of the business grows the other factors. Starting at the inner top, more product selection improves the customer experience, which in turn brings more customers, who then attract more sellers, further increasing the selection of products and continuously growing the flywheel. As the whole business grows, the upper loop of the flywheel activates, reducing costs and prices and feeding back into an even better customer experience.

A flywheel product takes the concept of this virtuous growth cycle and applies it to product development. Here’s how that works for me and Pegasus.

So my current professional strategy boils down to a simple plan: I want to launch projects and earn a living from them.

Sometimes those projects are my own revenue-generating ideas. Sometimes they’re paid gigs I take on for other people. But either way, it’s a perfect fit for Pegasus. The whole point of Pegasus is to help people launch SaaS applications faster; and it turns out I’m one of those people!

First off, Pegasus itself is an accelerator. And this will sound salesy, but it’s true: I can launch an MVP of a new project exponentially faster using Pegasus.

It’s funny, because I honestly didn’t totally get the need for a SaaS template when I built a SaaS template. I just saw that there were lots of bootstrappers building SaaS templates and that there weren’t any based on Django.

But now that I have a SaaS template? Sign me up for that! Pegasus really does save hours, if not days of work. (Admittedly, it helps to also understand the template at the “author” level and to use it several times. YMMV.)

So that’s part of the flywheel. The other part is that every new project I launch is an opportunity to improve Pegasus itself. My first experience using Pegasus led to a handful of new features and a lot of improved set of setup docs and code cleanup. Next I’m going to add subscriptions to one of my other products, and you bet your ass that’s going to end up back in Pegasus as soon as I figure it out.

Literally every new thing I build is an opportunity to make Pegasus better. For everyone. Forever.

The Pegasus Flywheel

The Pegasus Flywheel. A SaaS template accelerates my ability to launch new products, which in turn provide lessons and features to improve the template, and the cycle continues…

So I’m super stoked about this. Because I really enjoy building and launching new things. And getting to use and improve Pegasus with every new product launch just makes it all that sweeter.


2020 and Beyond

So that was my 2019. Fingers crossed—things mostly appear to be clicking into place.

Now before I get into concrete details about 2020, I need to first outline…

The Master Plan

Regular readers of my blog (“There are dozens of us! Dozens!”) probably won’t be too surprised by anything in this section, but I think I’ve never completely articulated it outside my own head. So here’s my master plan in three simple points.

1. I’d like to not have to work by 2023.

Yep. FIRE, baby!

To unpack that a bit—I fully intend to be doing something productive for 35ish hours a week in 2023, but I’d like for that to be a choice. So, basically, I need to be earning enough passive income to sustain my current lifestyle and savings goals by then.

For the sake of round numbers, let’s call that target $100k / year. Here’s how that might look broken out by year.

Year Passive Income
2016 $0
2017 $1,000
2018 $10,000
2019 $25,000
2020 $42,000
2021 $65,000
2022 $90,000
2023 > $100,000

My past and projected passive income from 2016-2023. Projections were made completely arbitrarily.

Does that look achievable? It does to me!

I just need to achieve growth levels that aren’t wildly out of line with my last three years and I should get there. And if it ends up being 2024 or 2025—well, that’s fine too. 2023 just feels like a good aggressive-but-not-impossible target.

Income by Category, 2017-2019

My complete income breakdown for the last three years. Side project revenue is creeping up and already at 25%! I’m hoping to get this number to 100 over the next 3-5 years—or substantially increase my annual income.

2. I don’t want to stop learning and challenging myself.

The second part of the master plan revolves around a continued interest in learning and personal growth. And two implications come from that.

The first applies to how I should strive to hit my passive income goal, and means that I should do it in a way that includes learning and personal development.

Thus, I should keep trying new and different things or upskilling myself in new areas, rather than e.g. inheriting millions of dollars and investing it in Bitcoin.

The second implication applies to what happens after I achieve financial independence. Specifically, it means I should have a plan for how to continue learning and/or challenging myself even when I don’t need to do so in order to earn a living.

I’ll touch more on both of these points in my 2020 plans.

3. I want to enjoy the ride.

Honestly, at least half of my motivation for all of this passive income stuff is just that I’m having a blast doing it.

Putting products out in the world, having people use them, receiving thanks and positive feedback, and eventually having that turn into dollars in your pocket is a magical feeling; a crazy combination of fear, anticipation, satisfaction, pride, and joy.

The analogy has been used before, but it really is like riding a roller coaster. Except you’re also building the track and driving the car. And yes, it’s been frustrating, and puzzling and difficult at times, but overall, it’s been a blast.

So, I know for sure that whatever I do professionally, I want it to feel as fun as this whole experience has felt so far.

Why this master plan?

Passive income. Personal growth. Fun.

Why these priorities? Why this plan?

Well, I don’t necessarily consider myself a philosophical person, but the crux of the master plan comes from one core tenet: our time on this earth is short and we should make the most of it.

A person could have many possible reactions to that statement, but an obvious (to me) one is that the more time you control, the better you can spend it. Passive income is really just a vehicle to eliminate one of the largest draws on my time: the 35-60 hours a week I’ve spent working for my entire adult life. Once that’s in place I won’t have any external forces pulling on those hours and I can do whatever I want with them. Which, admittedly, might be the exact same thing, but at least it will be a clear choice.

This is also why I want to enjoy the ride. Life’s too short to spend doing work you don’t love. For those of us who have the privilege of choice in our careers, it seems natural to think this way; though I should note that there are other equally valid conclusions one could draw—e.g. to always focus on doing charitable, meaningful work. Perhaps, if I were a better person that’s what I’d do instead. But for me, for right now, doing what I love—at least with the time I fully control—is more important than being charitable. (Also, thankfully I get to experience a fair share of do-gooding via Dimagi.)

Live as if you were to die tomorrow. Learn as if you were to live forever. Mahatma Gandhi

Turns out Gandhi was a pretty wise dude. Who knew.

And personal growth? I view that as an investment in future me. The more skills I have, the more practice I get, the more effective I’ll be with my time moving forwards. Much like software products, investment in yourself is a one-time cost that pays dividends for the rest of your life. So the better the human I want to be in 2030 the more I should invest in myself today.

Of course all of this is just on the “professional” side of life. The tenet also applies in other ways, like exercise, investing in my own mental health, spending time with family and friends, etc. But that’s a separate set of priorities that are out of scope for this post.

Plans and Goals for 2020

So now that you understand my master plan, it’s time to get concrete for 2020.

Here are my 2020 goals:

  1. Achieve $42k profit from side projects.
  2. Get my first ever recurring revenue.
  3. Launch one substantial new thing (> 80 hours invested).
  4. Seriously explore at least one non-standard project that I might do if I didn’t have to work.

Let’s quickly touch on each of these.

Achieve $42k profit from side projects.

Given that the master plan goal is to get this number up to $100k or higher, it makes sense to have some profit target as a goal. I suspect this will carry forward every year until I hit financial independence.

As for how I chose $42k? Well, mostly because I think $40k might be too easy, $45k might be too hard, and $3.5k / month makes a nice round target to shoot for.

It’s worth also noting that this is profit, not revenue, which means that things like Stripe fees and refunds don’t count. $42k profit is probably closer to a slightly more ambitious $45-$47k+ revenue from my current products.

Get my first ever recurring revenue.

Currently all my revenue comes from one-time sales (place card templates, Pegasus licenses, and Chat Stats upgrades). For several reasons, I’d like to get into the recurring revenue game.

The first is obvious, but worth stating: recurring revenue is much more predictable and consistent. While all my businesses are currently growing, it’s true that if Google decides to change its algorithm and Place Card Me disappears from search, my revenue could drop to zero almost overnight. And that’s just one of a million possible ways things could change very quickly. So, despite the historical trendlines of the past, I shouldn’t have any confidence that they’ll carry forward to the future.

However, if that revenue is recurring, it’s much easier to predict and protect. Subscriptions renew with predictable rates, and customers aren’t just going to disappear overnight even if you no longer show up on Google.

The second reason to pursue recurring revenue goes back to the Pegasus flywheel. Recurring revenue is still the game in town for many SaaS software companies. So for Pegasus to truly be the best SaaS template out there it has to support subscriptions. I’m planning on building subscriptions at least once for myself, then adding them to Pegasus.

The third reason is tied to personal growth. Simply, recurring revenue is harder and I think it will be good for me to keep climbing those stairs.

The Stairstep Approach

Am I finally ready to jump to Step 3? Image courtesy of Rob Walling’s Stairstep Approach to Bootstrapping—which I’ve inadvertently been following to a tee the last few years.

Launch one substantial new thing (> 80 hours invested).

An underwhelming 2018 led me to conclude that I should have at least one big new project each year. These keep me sharp and engaged, and honestly are just a lot of fun. So I’m hoping to do another one next year.

I’ve got a few ideas in mind, some of them revenue-generating, and some of them not at all. What I ultimately end up doing remains to be seen, and a number of these have totally different motivations which makes it hard to tie to a specific “master plan” tenet. But at a high level the things I’m considering are:

  1. A small B2B subscription SaaS product
  2. An educational site designed to make a big complex issue I know a lot about easier to understand
  3. A completely fun/frivolous thing in a creative space

Seriously explore at least one non-standard project I might do if I didn’t have to work.

One thing I keep asking myself is “once I achieve financial independence, what’s next?” And it’s amazing how I have no idea what the answer to that question is despite having spent the last few years marching diligently towards that goal.

So, this one is here to get me on a path to exploring that question more seriously. The main criteria is that it should be something that is not designed to make money (at least as a primary objective) that I might work on even if I had unlimited cash. Ideas 2 and 3 above would probably fit the bill for this and check both boxes. Other possibilities include upskilling myself on a hobby like cooking, surfing, or music production, leading hikes up Table Mountain, or seriously pursuing some kind of big writing project.

Or something else I haven’t even thought of yet!

Hoping to keep this one very open-ended and see what takes shape in the year to come.


That’s the year! As always, if you made it this far, thanks for following along, and if you’d like to see how this all goes you can sign up for my newsletter below. I send about one mail a month.

Family Photo

Happy New Year from our family to yours!