The Secrets To A Successful Side Hustle

The term side hustle comes across as a hobby, or half-serious pet project, or even wasteful distraction, but in the entrepreneurial world, such a thing often evolves into something career changing—heck, even world-changing. For example, some of the products I, and probably you, use day in and day out were started as side hustles. Here are just a few examples:

  • Gmail
  • Adsense
  • StumbleUpon
  • Instagram
  • Unsplash

They frequently will unexpectedly surge in popularity, or emerge as priceless gems that were hiding in plain sight all along, supplementing, overshadowing, or even supplanting the primary project.

In fact, the team at Crew, who made Unsplash as a side project for sharing high-quality, copyright-free images, say side projects saved their startup.

The Crew team was struggling to keep the lights on. Their product, a marketplace for hiring freelance designers and developers to build your product, wasn’t gaining the traction they’d hoped it would.

When you’re starting out, remember to start small and try to think of your side hustle as an experiment. After all, not every side hustle will be a winner.

But when Unsplash was launched as a Tumblr created in an afternoon, the response was overwhelming. Here’s what CEO Mikael Cho said about the experience:

More people cared about us in a few hours than in the entire last year. We made Unsplash to give something valuable to people. We thought even if a few hundred people find it useful, that’d be a win. But we didn’t expect it could have this level of impact.

That day, we not only experienced the immediate benefits of creating value but also a much bigger shift in how marketing needs to be done today in order to be heard.

The Crew team has since gone on to launch various other side projects. These projects have become the main sources of referral traffic to the Crew website, and Cho now sees them as an important part of Crew’s marketing approach, right alongside content:

Marketing today is defined by how useful it is to your customers. And the bar for useful has risen substantially. Where blog posts, infographics, and webinars were once marketing gold, websites, apps, and tools are taking over.

But running successful side projects doesn’t come easily to everyone, and it’s kind of an art. It requires a combination of zen and dedication, letting things percolate and develop on the periphery, while steadily nudging the idea forward. To help you get the most out of your side projects, I’ve compiled wisdom from some of the best side hustlers out there.


So how do you choose a side hustle? What makes it different from any other project? Here’s what serial side projectors have to say about getting started.


David Hieatt is primarily focused on making jeans at Hiut Denim Co., but he’s no stranger to side projects. Hieatt and co-founder Clare Hieatt started another clothing company called Howies in 1995, but it wasn’t until 2001 when they first received a paycheck from the secondary project.

In those six years, both David and Clare worked their day jobs to keep the bills paid, and ran Howies on the side. But it caught on and picked up speed. Eventually they sold Howies to Timberland, using the profits from that sale to fund other side projects.

David has three rules for starting a new side project:

  1. No pressure to make money
  2. No deadline
  3. Labor of love

The first rule fits with the Hieatts’ approach of keeping a day job while building a side project. If you don’t put pressure on your side project to pay your bills, it doesn’t matter if it fails. This gives you more freedom to experiment without risk, one of the core reasons side projects tend to be so creatively rich.

Having no deadline similarly opens up possibilities for experimentation, since you have room to breathe and try on new approaches. As David says, “As there is no time pressure, you don’t revert to your usual formula.”

And finally, Hieatt says side projects need to be a labor of love, because “this thing will require you to keep plugging away at it, maybe, for years.” Working on something you care about will make it easier to keep coming back when there’s more work to do. Think of it almost like an old roadster in the garage you tinker with for relaxation, or a yacht you sand and polish on the weekends with a twinkle in your eye.

Yar, she’ll have a beautiful IPO one day…

Unlike the common startup mantra of “fail fast,” David says side projects are all about “succeeding slowly.”


Having built more than a handful of side projects mentioned above while at Crew, Mikael Cho has some great advice for getting the ball rolling. He has two main rules for designing a side project for your company (though they’re equally useful for individual entrepreneurs):

  1. Small scope
  2. Minimal updates

Cho says for side projects, “The best approach is to keep it simple.” Each project you create should be just 1–2 pages, minimal complexity, minimal coding, rather than a sprawling web app.

Nothing wrong with being small.

Cho also suggests looking for a way to solve a problem with a much simpler approach than what anyone else is doing. “Reduce features to the minimum,” he says, and don’t worry about handling user accounts. Make the project simple to build and simple to interact with.

Simple will be your edge.

In terms of maintaining the project, Cho also insists on simplicity. The smaller your initial scope, he says, the more you’ll reduce the need for maintenance in the future.

“We only update one of our projects if it’s doing exceptionally well and the update has the potential to make it much better,” Cho says. “Exceptionally well” for the Crew team generally means the project is one of their top five sources of Crew referrals.

Unsurprisingly, Cho is a fan of moving on to building new side projects when possible. He says before working on a project you’ve already released, you should ask yourself whether your time would be better used building something else.

It’s often more efficient to move on to a new project, he says, if you release something that doesn’t resonate with your audience.


If you’ve worked on a side hustle before, you’re probably thinking this all sounds great, but how will you ever find the time? I hear you.

As if working your day job or running your company isn’t enough, you’ve got family and friends to spend time with, hobbies to work on, and your health to look after. In what dream world does it make sense for you to add even more onto your plate?

Well, aside from the previous advice of maintaining small scope, simplicity, and a lack of deadline, there is some prioritization and logistical tips that can help you manage a successful side project.

“We find the time for those things we place importance on,” says Rachel Andrew, founder of edgeofmyseat.com. If you have many important things competing for your time and attention, you’ll inevitably make a decision about which ones take priority. If your side project is at the top of the list, you can be sure you’ll find a way to make time to work on it.

Andrew says if you’re struggling to make progress on your side project due to lack of time, “take a reality check: is this something you really want to achieve?”

To stop a project from stagnating, Andrew believes it’s important to make it a “first class citizen.” Even if you can’t spend as much time on it as you do on your existing business, Andrew says giving it the same priority as your other work will ensure it keeps moving forward.

She also suggests setting aside regular time each week to work on your project so it doesn’t get overlooked, and finding ways to make better use of downtime, as she did in her studies:

Several years ago I earned a degree with the Open University in the United Kingdom, via distance learning. I did all of the reading for my courses while waiting outside my daughter’s ballet classes.

Andrew says the best way to make better use of your downtime is to always keep an up-to-date to-do list for your project, so you know what needs to be done whenever you have some free time. She also suggests making sure your workspace is prepared ahead of time, since we tend to find small slots of free time to work on side projects:

Spend some time at the start setting up a great workflow for the project, sign up for any API access you need, install any software. Make sure that those short bursts of activity on the project can be used to drive it forward.

Product manager and entrepreneur Jason Shen also has some advice about finding time for your side projects. He suggests focusing on consistency more than intensity. So, rather than working on your project for several hours once or twice a month, try putting aside half an hour, or even 10 minutes every day.

You’ll make more progress in the long run if you keep at it a little bit each day, than if you immerse yourself once every few weeks.

Before Shen built his first web app, he says he spent around 100 hours over several months to learn enough programming for a prototype. But if he squeezed all that effort into 50 hrs/week for two weeks, Shen doesn’t think he could have stuck at it.

He also points out how small chunks of time can easily add up in the long term:

You really only need average 35 mins a day on your side project to net 4 hours a week on your side hustle. That’s 200+ hours over a year – which would allow you to do a tremendous number of things.

Whether you want to build the next Gmail, or broaden your company’s marketing approach like Crew did, side projects can be extremely valuable to you as an entrepreneur. Even if your projects don’t blow up into huge hits, simply pursuing them helps you learn new skills and lessons you can apply to your main business.

When you’re starting out, remember to start small and try to think of your side hustle as an experiment. After all, not every side hustle will be a winner. But keep at it every day, and you’ll be surprised at the things you can accomplish on the side.

Got a question or tip for running a great side hustle? Let’s hear it in the comments below!