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Startup Report

Don't Quit Your Day Job (Yet): My Year In Part-Time Entrepreneurship

When you're building your startup on the side, everything takes longer than you want it to.

Don't Quit Your Day Job (Yet): My Year In Part-Time Entrepreneurship

[Photo: Jacob Ammentorp Lund/iStock]

I've been in the process of becoming an entrepreneur for a little over a year now. As some may see it, that means I've already failed. Certain business gurus will tell you categorically that entrepreneurs are born, not made. Their experiences are worth listening to, but I disagree. I suspect that many more people could start their own companies. They just have to find an idea they care enough about to be willing to confront the thousand obstacles that arise trying to make it happen. Last year, I found mine.

Roughly 15 months since I first brought in my cofounder, followed by our first few employees, we're now finally on the eve of launching a startup that connects enterprise-software product managers to users in their potential markets. And so far, all the work it's taken to get here I've done part-time.

I know I'm not alone. Plenty of entrepreneurs toil on nights and weekends—hanging onto their full-time jobs—before devoting themselves completely to their new business. The goal is to save money and prove that the idea has legs before pushing all your chips in. For those of us who aren’t independently wealthy and/or have dependents who rely on us for a steady income, it’s often a necessary period—and one that can take longer than hoped for.

And it often kind of sucks. Here's how I've gotten through it so far.

Tested Patience, Steady Paycheck

Working part-time on a startup is frustrating. The emotional ebb and flow of starting a business is already intense, but part-timing also tests you as a manager in some ways I didn’t anticipate.

For instance, I’ve never felt a larger gap between what I wanted to do and what I'm able to do in the time available to me. Things I usually take for granted, like being able to coordinate schedules, is just harder in the off-hours.

And with time being so scarce, even minor delays are magnified—they can set you back much more than you'd expect them to. That's an infuriating and impotent feeling when you just want to get to market fast.

The main advantage, of course, is that you aren’t burning through savings while you figure out whether you've got a viable business in the works. About eight months into development, I decided we stood a better chance of succeeding if we shifted our product's emphasis. It was a pretty fundamental change that I knew would add months to our timeline to make, but after taking admittedly too long to decide, I finally concluded that it was the right decision.

If I hadn’t had a paycheck in eight months, though, I might've tried to talk myself into staying the course. I know myself well enough to realize that I’m no more immune to making bad decisions under pressure than the next person. So having my day job was a crucial resource—not just financially, but for making smart choices, too.

If you're lucky, the skills you build leading a nascent company through the part-time phase will lead to success as a full-time CEO. (That's what I'm hoping, anyhow!) But in my experience, being prepared for the challenges of the part-time phase can raise the odds of making it there. If you’re at that stage right now, or thinking about taking your side project to the next level, here are a few things worth keeping in mind.

Goals Still Matter

It sounds obvious, but accountability is harder than usual while you're building a startup part-time. When we’ve missed the milestone dates I've set for myself, it’s usually been because of a huge workload at my own or one of my startup team member's day jobs.

I hate it when this happens, but I can’t tell anyone to ignore their boss (and I can't ignore mine). After all, you can only push other people or yourself so hard before it backfires. And that's especially true when your team is already giving up most of their free time and often a good deal of sleep.

That’s why you have to commit—as a group—to milestones you think you can hit, then hold each other accountable to keep up morale. Remember, without schedules, your side business will quickly regress into being a mere side project.

Don't Be Fooled By Fake Progress

As a part-time entrepreneur, I’ve often found myself sympathizing with my former bosses. Previously, while working as a product manager, I had the relative luxury of insisting on doing things right, not fast. But as a CEO, I've had to fight the urge to rush into development just to see progress, even before we knew what we needed to build.

That need to see tangible progress can be dangerous, and it doesn't help that the progress is always slower than you want during this period. Rushing or skipping steps isn't the answer, though. The fastest way to the finish line is still to do things right rather than to do them twice.

Look For Motivating Wins (Even Small Ones)

You can't just keep pushing people indefinitely when they're already tired and facing yet another night with only a couple hours' sleep. This definitely got a bit easier as we brought more people onto the team, because they could encourage each other, and it wasn’t just my voice they heard.

Boosting sprits matters. Look for those milestones wherever you can. In the part-time phase, getting over even small hurdles is worth cheering. Finalizing our logo was hugely galvanizing because it made the effort we were making feel more real. During rough patches, you can start to doubt that it is.

Building a startup part-time doesn't mean you aren't serious about it, though. If anything, it's the reverse: Staying committed, focused, and deliberate while keeping an eye on the long game is what it's all about. That's a mind-set that comes in handy for any entrepreneur, full-time or otherwise.


Christian Bonilla designs analytics software at Resonate, despite having no formal engineering training. You can follow his business ramblings at SmartLikeHow.com or on Twitter at @smartlikehow.

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