Another Leap

I’ve taken three significant steps into the unknown in my life. The latest was a month ago, when I decided to leave my job.

The first came a year after my wife and I got married. Living in Chicago and having grown up in Michigan, we were eager for sunshine, warm weather, and a fresh start. We decided to move to Texas, a place where we didn't have jobs or know a single person. It’s been our home ever since.

The second leap was a few years later. I had one of those awful jobs—an owner who couldn’t be trusted and checks that sometimes bounced. I found my dream job, but it was only part-time. For a few weeks, I did both, but I sensed that committing to a better future was part of making it reality. I quit my full-time job, despite having a house and child, and no idea if my part-time job would ever be more than that. Within two weeks, I was offered a full-time position and my career began in earnest.

When I tell those stories, I cast them as tales from the distant past. As time passes, stability grows in importance and leaps into the unknown seem unwise. The person who took those chances feels like a character in a story.

I poured myself into my most recent job for eight years. I joined as the team was just taking shape and later became the VP of Product. I hired the first designer, data scientist, office manager, support advocate, customer success manager, and content strategist. I encouraged our inclusive, supportive culture and championed remote work, hiring the earliest remote employees. I led the adoption of Shape Up and got to work with some of my best friends.

I also grew and learned and made mistakes.

Joining the company was one of the best decisions I’ve made, and so was deciding to leave.

A few months ago, I read this post: 5 Signs It’s Time to Quit Your Job. It’s a great prompt to look at your current job through the lens of your career.

I had long thought I couldn’t leave—the people, product, and history meant too much. Plus, I feared the uncertainty of a job search. Two realizations shifted my view.

First, I realized that the job's importance and my own were overinflated. The best job is still a job and can be replaced. The same is true for an employee. Life will go on.

Second, I asked myself, "Would I apply for my current job?" Put that way, the answer was clearly no. I was valuing the past at the expense of my present and future.

It sunk in one morning as I was watching this U2 performance of all things: it’s time to leave and take another leap. I had to make that commitment to myself and trust that what doesn't make sense right now will later, just as it had before.

Not long after, I celebrated those eight wonderful years with coworkers past and present on a beautiful Austin evening.  

I accepted an offer for my next job a week later.

I’m overjoyed, filled with gratitude, and happy to tell a new story.