For Jon Leland, the years after college did not move in a straight line. Like many recent graduates, he wandered. Perhaps “wandering” doesn’t fully capture it. Jon was all over the place. After graduating, he turned down a cushy job as marketing director of a company in Washington, D.C., to become a busboy at a crappy restaurant in Bar Harbor, Maine.
It was the best decision he ever made. In Maine, he got to know an alum from his school who was starting a nonprofit in South Africa, and Jon agreed to help her get it off the ground. The nonprofit, Thanda, provides education to orphans and vulnerable children whose lives have been marginalized by the HIV/AIDS epidemic. He spent the next three years moving around, building a computer lab and teaching a computer course, building freelance websites, and teaching the LSAT.
If you think you know where this story is heading, you might be right: Yes, Jon eventually became an entrepreneur. But he didn’t stay one. There’s no shortage of popular narratives out there about ambitious, purpose-driven people who don’t find much fulfillment climbing the corporate ladder and instead wind up starting their own businesses or working for themselves. That was the case for Jon, too—temporarily.
What many of these anecdotes—shared over networking cocktails, rehearsed during panel talks, or recounted in Medium posts—don’t show is that it’s actually sometimes preferable to pursue your personal mission inside a company than to do it on your own.
Upon returning from South Africa, Jon enrolled in law school at Stanford but quickly learned that he didn’t actually want to be a lawyer. So he took what seemed at the time like the next logical step and decided to start a tech company with a few other Stanford students. At the same time he was finishing law school and studying for the bar, Jon was building MyProject.is, a site that allowed people to use their network to help crowdsource ideas, information, and resources to help realize their projects.
“Once I saw the opportunity to create something to help people make things, that just became so much more compelling to me than being a lawyer.” Recalls Jon:
I had gone to law school in the first place because of the way of thinking that law schools value. In retrospect, it was a stupid thing to do. Starting a company after graduating instead of being a lawyer wasn’t easy, to say the least. I graduated with more than $150,000 of debt and spent the first year racking up credit card debt, scraping by, and constantly worrying about my ability to keep myself and my company afloat financially.
“Eventually, as we continued to struggle with a core piece of the technology under the platform,” he continues, “I accepted an associate attorney position at a big law firm in Manhattan. That meant I also had to take the bar exam, while I still had the company in San Francisco. It was impossible.” Jon was burning out. “I was flying back and forth when I could,” he remembers, “meeting potential investors at all hours, and working every moment. I wasn’t fun and I wasn’t healthy.”
Many books that tell you to “do what you love” or “start the business of your dreams” don’t tell you how hard it is to actually run a startup. Jon and his cofounders discovered that running a business was too taxing on their bank accounts (and their sanity), and they couldn’t afford to keep MyProject.is going. There wasn’t a good option for selling the company, though, so Jon ended up taking a job offer from Kickstarter, a much larger startup that, like MyProject.is, helps creatives make their dreams come true.
In the last two years, he has worked as the director of community engagement and the director of strategy and insights, helping Kickstarter grow its community of creators and backers, developing strategies for international markets, and helping the company grow. Jon learned a hard truth most career advice books rarely teach you: Sometimes you can make more of a difference when you work for someone else.
“The impact I have now is so much greater than the impact I had running my own startup.” Jon explains:
Honestly, the mythologized “scrappiness” of being an entrepreneur in reality means being constantly focused on just keeping things afloat—particularly when you have employees to take care of. Now I have a large role to play in helping shepherd the path of one of the world’s most culturally impactful technology companies. Kickstarter is a small, independent company (120 people and founder-controlled), so everyone’s voice matters. I am learning more, worrying less, and serving the vision of my startup better through my work at Kickstarter.
Rather than being preoccupied with getting press, building a consumer base hand over fist, scraping together funding, and managing the inevitable coolness factor of being an entrepreneur, Jon is more focused on the impact he wants to have: helping creatives make their ideas become reality.
His experience hints that it’s okay to be a wanderer—as long as you’re wandering with intention. We can’t know exactly how our path is going to unfold. Jon’s resume doesn’t make much conventional sense; his first decade in the workforce included being a busboy, helping a nonprofit in South Africa, going to law school, starting a tech company, and then going to work for a tech company. In some ways, it’s the “job-hopping” nightmare trajectory that younger workers are often warned against. But Jon listened to the voice within whenever it told him it was time to jump.
Jon’s advice in retrospect?
Don’t feel like you have to figure out the thing you should be doing with your life. Just find a thing to do for a time. It can be on the side; it does not have to be everything. Don’t martyr yourself. It’s good to have goals or a vision of where you want to be—it helps orient and motivate you on your journey. But as you go toward that vision, be very open to new paths and opportunities that open up along the way.
You don’t have to know “the thing.” There may not even be one thing for you. What’s more important is being open to making mistakes and course-correcting when you do. And sure, that may ultimately lead you to work for somebody else. But that may turn out to be the most meaningful thing you can do. And you’ll know it when you’re doing it.