As I announced earlier this week, I quit a great job at TicketLeap, one of Philadelphia’s most promising young companies, without any idea of what I would do next. I hadn’t even started the search.
It’s either brave or foolish, depending on who you ask. It’s also hard to understand, especially for my mother. I think she worries that I’m too proud to move in with her — that she will see me on the news one day holding a sign that says, “Will bring you customers for food.”
So I want to share the story of why I left and why I did it without a parachute. I also want to give you some ammunition in case you find yourself in a similar situation. After all, it’s hard to explain your apparent insanity to everyone you know. It’s also hard to ignore that voice inside your head that will say anything to talk you out of it.
The million dollar question
Before we go any further, let’s acknowledge the elephant in the room: it seems insane to jump without a parachute, especially in a recession. It seems insane for one simple reason.
Why would anyone leave a good job at a great company without a plan?
Fair question, right? Unless you have a good answer, people tend to assume one of three things: either it wasn’t a good job, it wasn’t a great company or you must have had something else lined up.
As it turns out, I really liked my job. I saw a bright future for myself with the company and hadn’t begun to consider alternatives. I just had to leave. But before I explain why I had to leave, let me share all the reasons I told myself not to leave – and why those reasons were hard to ignore.
Why I didn’t want to leave
First of all, I enjoyed my work. I had the opportunity to build a high-octane marketing engine from scratch and use that engine to help drive several multiples of growth. I got to do it with one of the most talented teams I’ve ever worked with. I learned more from the problems we solved together than from anything else, and that collaboration is the thing I’ll miss most.
On top of that, TicketLeap is thriving right now. I could have ridden that success to a top-flight marketing career if that was attractive to me. The company is on track to be a leader in long-tail ticketing, a market larger than the arena ticketing space controlled by TicketMaster. I had the opportunity to run a giant marketing department and build a nice nest egg for myself in the process.
Within the company, I was at the peak of my productivity and relevance. I had just kicked off arguably the most important project for the company’s future growth: building a marketing machine that drives ticket buyers to our marketplace, rather than depending on event organizers to bring their patrons.
I had several breakthroughs as I started this project that grew into a roadmap for how TicketLeap could dominate long tail ticketing. I left behind a slide deck that I’m quite proud of. The deck’s title should give you a sense of how badly I want to see them succeed: “How to dominate long tail ticketing (and kick even more ass after I’m gone!)”
My heart was no longer in it
As much as I wanted my friends at TicketLeap to succeed, and despite all the good reasons to stay, I felt a sense a sense of dread as I sat my desk during my final weeks.
At first, I didn’t understand the feeling and willfully ignored it. After all, my team and the company were depending on me. And this job was good for me. The things I was learning would help me build companies and movements in the future, and the splash I made at TicketLeap would show others what I could do.
But all this eat-your-vegetables self-talk did nothing for the dread. I didn’t want to be there anymore. As soon as I realized that this feeling wasn’t going away, I started to listen to it.
Building a business without making a difference
As much as I love building businesses, my first love had been politics, service and social movements before I discovered entrepreneurship. Deep down, I still wanted to change the world.
But I had given up on changing the world, at least for a while. My experience in politics and non-profits had been frustrating and tedious. Most of the organizations I joined were bureaucratic and slow. They were so worried about getting things wrong that they didn’t dare to get things right.
In entrepreneurship, I found the aggressive drive to innovate and get things done that I had been longing for. I discovered that I liked solving problems with entrepreneurs more than with anyone else. And I liked that I could solve problems without so many obstacles and constraints.
The challenge of entrepreneurship and the spirit of teamwork inspired me for three solid years. It kept me working 90 hours each week while I built Anthillz (my first company), Philly Startup Leaders (my first movement) and the marketing machine at TicketLeap.
But more recently, that passion began to fade. I had started to understand the puzzle of building businesses and organizations, and I was no longer interested in solving the Rubik’s Cube just for the challenge of it.
I also discovered that I’m happier when I’m a leader and a generalist rather than when I’m in a specialist role, as I was at TicketLeap. I knew this already but it helped to have it confirmed. After all, I had changed in many ways in the years since my last typical job.
As I lost interest in TicketLeap, the existential questions began to creep in. Why put in so many hours and so much stress just to give our clients better ticketing? What if we chose instead to direct our talents and energies towards solving a bigger problem?
Don’t get me wrong, I love and understand the drive to build businesses. That’s why I pour so much of my life into Philly Startup Leaders. Startups like TicketLeap are the foundation for the economy and quality of life we all depend on. Without this foundation, there would be more suffering in the world than a million non-profits and political movements could ever hope to solve.
The problem is that, at this point in my life, I don’t want to build businesses just for the sake of building businesses. I realized this as I sat at my desk at TicketLeap, looking at the project ahead of me and imagining the next year of my life there.
It kept me up all night on the weekend before I gave notice, the worry and panic fighting me tooth-and-nail as I made my final decision. And then the next morning, a Monday, I walked into my boss Chris’s office and told him I was leaving.
There was only one way to jump
I didn’t have to leave so abruptly. I could have waited until I figured out where I wanted to land. That would have allowed me to use up my vacation days and collect the stock options that were only a month away from vesting.
But that seemed wrong, both for the company and for me. My role at TicketLeap was critical and demanded everything I had. How could I do what they needed while I searched for the next thing? Likewise, given how seriously I took the search for my next opportunity, how could I do it right while working more than a full-time job at TicketLeap?
I didn’t see a way to square the circle.
Plus, there was the issue of my psychology. Some people can spend their time doing one thing while their mind is checked out, thinking about something else. I can’t. If I was going to spend most of my waking hours working at TicketLeap, my mind was going to be focused there as well.
If I was going to jump at all, I had to do it without a parachute.
Working on my landing
It’s been a few weeks now since I jumped. While it’s far too early to declare victory, a few things have started to fall into place.
I’ve lined up some consulting work even though I wasn’t seeking it out, which buys me time and may placate my understandably worried mother. My friends and colleagues have been extraordinarily generous in connecting me with opportunities in social entrepreneurship, service and politics. And I’m starting to come up with ideas for projects of my own.
If I was still a betting man, I’d say the odds are good that this was the right move. But the great thing about being an entrepreneur is that I don’t have to take this bet.
This time, unlike when I was a playing poker professionally, I get to set my own odds. And I’m really looking forward to that.
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