How I *Actually* Finished My 19-Month Side Project

Published on
January 20th, 2020
"It’s now clear to me why so few side projects see the light of day."
On a Wednesday morning in May of 2019, I posted my side project, Outro, to Product Hunt. It marked the end of a 19-month journey. By 9 a.m., I sent 114 personalized emails to my entire network. In celebration, I took the day off work (as a PM at Hello Alfred). By 12 p.m., I was biking to Central Park in NYC, where I spent the afternoon reflecting; this was a big day for me and I felt an extraordinary weight lifted off my shoulders.
Outro is an app dedicated to hosting team retrospectives in an entirely new way, based on eight years of my own learnings running weekly retros. I’ve got a very unique way of running retros (which I’ve written about here), focused on celebration and accountability instead of “agile methodologies.” I thought, what if I build an app purpose-designed to host retrospectives *my* way? I’ll infuse it with personality, make it easy for other teams to learn how to run retros, and I’ll do it all as a side project because…how difficult could that be?
It was an order of magnitude more difficult than expected. Of course building software is hard, but that was easy compared to the challenges I faced juggling my job at Hello Alfred (which I care deeply about), finding the motivation to work on weekends, and balancing some semblance of a social life. It’s now clear to me why so few side projects see the light of day.
If you’re considering or are in the middle of a side project, these are the practices that helped me launch Outro:
  • Find value in the journey itself (not just the end product)
  • Embrace the “slow and steady” approach
  • Recognize the outsized importance of finishing

Finding Value In The Journey

A side project is not a glamorous or easy endeavor, and you won’t make it far in your journey if your only goal is to be done with it. To succeed, you must find value in the journey itself, which effectively acts as the fuel needed to get through all the lows.
Start by asking yourself why you want to do this. Is it the creative pursuit itself? Is it to learn a new skill or industry? Is it to solve a personal pain point? Assume (if only for a second) that your project will be a commercial failure. What value will you extract from this journey so that it was a personal success?
Here’s why I wanted to start a side project:
  • I wanted to see how far I could push myself. My first side project was a baby one — I created
  • I was craving something creative that would make me look forward to tomorrow.
  • I genuinely wanted Outro to exist for myself. I’m so crazy about retros that if I ended up being Outro’s only user, that would have been enough.
During this journey, I found it imperative to reward myself to continue to stay motivated. About halfway through building Outro, I was working on a “make or break” feature that had me feeling anxious and avoidant; I was stressed about the moment in the user journey when a user finishes a retro, which to me needed to feel like a celebration because the retro was over.
I came up with a clever way to solve my procrastination: a reward. I booked a thermal bath for Sunday evening, which meant I had to finish the feature by Sunday or else I wasn’t going to the spa.
It was the best spa experience of my life because I felt like I truly deserved it.
But rewards don’t need to be so lavish. Most of my “rewards” fell into the following categories:
  • I deliberately picked coffeeshops in neighborhoods I could enjoy exploring around after
  • I planned activities for after I was finished, like a museum or a movie, or dinner with friends

Slow and Steady

One rule of thumb for software development timelines is to double your estimate. Then add two weeks. In side-project land, it’s safe to quadruple it. When building Outro, I felt about two months from being done for nineteen months.
I spent 16 hours building Outro’s “Kudos” button, which is just a couple days of full-time work, but netted out to a few weeks at my pace. A few weeks on one little button! But I wanted the “Kudos” button to be significant during retros, and explode with excitement from a UX perspective. It’s now the single feature I get the most positive feedback on.
Your side project will take longer than you expect. Here’s how to avoid burnout and keep a slow and steady pace.
I recommend picking consistent blocks of time to focus on your side project. I carved out Saturdays and Sundays from around 12-5pm. This meant having to turn down plans with friends constantly, leaving parties early, or skipping the gym. I consistently felt like a bad person doing this, but this was my optimal time for working, and there would be life after Outro was launched after all.
Also consider taking a side-project-cation. Getting into a flow for multiple days straight to make step-function progress can be a fantastic change of pace. I actually started Outro while on vacation in Montreal!
It’s also helpful to use a timetracker. I spent exactly 506 hours working on Outro before launch. I know this because I used a time tracker to record all of my sessions. I started doing this to understand what kind of time investment a side project like this would take, but I ended up developing a bit of a Pavlovian habit that turned out to be super productive.
As soon as I hit the start button, my brain would shift into work mode. I found this particularly helpful on days when I was procrastinating. All I had to do was hit “start.”
Time-tracking was a small habit that had a surprising impact on keeping me going. Plus, you get a graph like this:
While you’re working on your side project, shelve your other brilliant ideas. Write them down in a notebook to get the ideas out of your head, and then put the notebook away for later. The silent killer of so many side projects is the shiny-new-object of a fresh idea.
New ideas don’t have any constraints. They’re not fraught with problems, and their possibilities seem limitless. Meanwhile, your side project is hitting wall after wall.
The two aren’t comparable, so be aware of that discrepancy ahead of time, and shelve your other brilliant ideas until you’ve finished.

How to Finish

The point of this blog post is to offer tips and guidance on how to actually launch a side project, because so many projects don’t make it there. But, if you can finish, you’ll have developed a relatively rare skill that will make it easier to finish the next time. That skill is worth about as much as the side project itself.
A few of my recommendations to get past the finish line:
Tell others what you’re working on, as well as what milestones you’re trying to hit. This was uncomfortable, but I did it to hold myself accountable. Questions like “How is it coming along?” and “When are you going to finish?” were sometimes painful for me to answer but nonetheless helpful.
I felt especially accountable to my team at Hello Alfred. We started using Outro while I was still developing it. Every week after retro I’d hear feedback from them. To avoid hearing the same feedback repeatedly, I’d move quickly. I built Outro’s weekly recap email feature in just a week, because of feedback from team members that they couldn’t remember the retro concerns they were assigned.
It's important to build that finishing muscle. More specifically, practice these two exercises:
  • Button up all the loose ends that are needed for launch
  • Cope with the anxiety that is building up as you get closer to the end
These exercises almost feel purposefully designed to hold you back.
The list of things you forgot or put off can get long, especially if this is your first side project. Do you have a privacy policy? Is your landing page SEO-friendly? Do you have marketing collateral ready to go for Product Hunt? I was scrambling on all these items, convinced that I was missing ten others that would ensure my complete failure at launch.
Then there’s the anxiety. Nineteen months of working on Outro, and the results of all that work on display, ready to be judged. I’m no expert on anxiety, but I do know that exposure therapy is a common treatment. And the only way to get exposure to finishing is to finish.

Was Outro worth it?

Outro has seen over 200 signups, ten of whom converted into paid customers, taking a chance on a new way to run retros with Outro. I get to read feedback like this from happy customers:
"It was clear to me after a few weeks that every team should be using Outro. It's magical the discussions it creates. [The Branch] exec team has even started using it for our meetings." - Joe Emison, CTO at Branch
I am incredibly proud. I built something people use, love, and even pay for. But we can all agree that ten customers is by no means a commercial success!
Thankfully, Outro’s value comes not just from the number of paying customers. It comes from the journey. But somewhat unexpectedly, it created new journeys too. Like the one I’m on now to grow Outro’s reach and customer base. This means I need to flex into areas I’m much less skilled at, including sales and marketing, public speaking, and (*cough cough*) writing.
It’s daunting to think about the journey ahead. I’m a Product Manager by trade, so building a great product is what I’m good at. Sales, marketing and everything else is entirely new to me. But it’s obvious to me that working on these skills will be immensely valuable. And now I have a toolset that I can leverage to navigate my way through it, slowly but surely.
Side projects are uniquely challenging, but immensely rewarding. If you can figure out how to cross the finish line, you’ll have something that will pay you dividends personally, professionally, and maybe even financially.
Published on
January 20th, 2020
Comments (3)
Taylor Crane
Founder @ Clubs Poker
Hey all - Taylor here. If you’re interested in kicking off a side project of your own, and have questions/concerns, I’d love to help you. Or, if you want to give Outro a shot with your team, I’d also love to talk. and @taykcrane on Twitter is how to reach me
Raj Mahal
Travel Enthusiast
Congrats! I know the struggle. My side project PlanMoreTrips, I started in 2014 and now after 6 years, I just finished it haha.
Anna Filou
Geek, Designer, Illustrator, Web Dev
Wonderful article. I so needed to read this <3