What I Learned from the First Round of Ship Your Side Project

As you may remember, earlier this year, Amanda Phingbodhipakkiya and I ran a six-week bootcamp for midcareer tech professionals called Ship Your Side Project.

Our thesis was that there are tons of people out there tinkering on passion projects who have maybe gotten a little side tracked and lost steam, but with just some structure and accountability, they could launch a v1 of their project. The 300+ upvotes we earned on ProductHunt and the thousands of visits to our site told us that we were onto something that might have legs.

In January 2016, SYSP kicked off its first batch with 13 designers, engineers, product managers, and entrepreneurs hailing from Brazil, Canada, San Francisco, NYC, and Portland. They busted their asses for six weeks, made some incredible progress, and we all had a pretty good time along the way.

I definitely learned a lot from that first batch, both on running a program like this and the process of shipping a side project.

Set up a Schedule and Stick to It

Every one of the six weeks of Ship Your Side Project had two assignments, an interview with an expert side project professional, and a weekly Google Hangout. One of our first assignments is to pick a specific time in your calendar, ideally earlier in the day, where you focus on side project. Our philosophy is that even just 15 minutes of consistent progress every day makes a huge difference.

As one of our participants put it:

“The biggest winner for me has been consistent time blocks on my calendar. Sometimes these have been pushed for other things that come up, but the fact that I’ve planted a stake in the ground makes me much more likely to hit it.”

The same held true for SYSP itself. Knowing that I had to send out a homework assignment every Monday and Wednesday night and be ready for a Google Hangout every Saturday helped me plan my time and not get confused about when I was doing what.

SYSP weekly calls

Amanda and I in one of the weekly hangouts

People Crave Personal Attention

One of the things Amanda and I did was record individual 1-2m videos three weeks into the program that was personalized to every single member. While we found talking into the webcam a little awkward at first, it started feeling natural after the 2nd or 3rd one and wasn’t particularly time consuming or costly (compared to say, scheduling an interview with an expert, recording the interview, getting the transcript of the conversation, etc).

However, we found that people really resonated with these videos. Even though we were responding to people’s questions and comments in the email list and on the weekly calls, this one-on-one video was called out in our final feedback as something they really valued and wanted more of.

That’s why in our next round of Ship Your Side Project, we’ll be incorporating mentors who will work more closely with a handful of participants to

Cut It Down

The longer you work on something, the more ideas you have for it. This is generally a good thing, but when it comes to side projects, small is beautiful. We get into our projects because we’re passionate about them and we have a vision for how awesome our game / tool / service / program could be when fully realized. But when we compare what we have ahead.

As I wrote in my article Start Smaller:

Small products do not always succeed, but they are easier and faster to build, test, and tweak than bigger products.

The participants that did the best were the ones who cut down on their original idea until they had something manageable to ship as their V1.

During Ship Your Side Project Adam Duvander launched a site called EveryDeveloper, an API comparison site, which is an idea he’s been tinkering with for more than a year. He originally wanted to launch with the content for 12 different APi categories, but ultimately cut it down to six, reducing his time to launch from months to weeks, and helping him validate and get feedback sooner.

This next round of Ship Your Side Project is going to be immeasurably better, but only because I cut down some of the things I wanted to do in V1 so I get it out the door.

Set a Date and Work Backwards

I set the Jan 18th date for Ship Your Side Project in September 2015, giving us five months to develop 12 assignments, conduct and transcribe interviews with experts, design a brand and program materials, and recruit & evaluate participants. Not everything went according to plan, but by working backwards from the Jan 18th date, we were able to figure out what needed to happen by when to have a successful program.

Hopefully not what ends up happening

Hopefully not what ends up happening

A date really has to feel real to be effective. We found that the students who really committed to launching by the end of the program were the ones that really got things done. Most of that pressure was personal, and within the community, but I think I’m going to experiment with ways of adding to the pressure in this next batch.


So as you might guess, I’m getting ready to launch a Fall 2016 cohort of Ship Your Side Project. This cohort will be especially geared towards engineers, programmers, and technical side projects and it’s going to be awesome. We’re taking everything that worked about the first cohort and making it more fun and more effective.

To hear about when applications open for the new cohort and get a free tool for evaluating side project ideas, click here.

creative process image via Toothpastefordinner.com

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