I recently shared the idea of doors for moving your career ahead. That there are doors you can try to open—or offer someone, if you’re in a leadership role— besides “quit” or “get promoted.” Almost immediately, someone asked, “But which door is for me? Please help me choose.”

How did I respond? Before I get to that, I have a story to share.

Once upon a time, I packed up all my belongings in my tiny Geo Metro, threw myself a going-away party, and drove all the way from Austin, Texas, to San Francisco for a job. Less than three weeks later, I was back in Austin. I was embarrassed, devastated, homeless, and, more importantly, had no job.

I was a travel agent at the time (yes, this was before you could book your ticket online all by yourself), and I had a dream of taking my experience to a company creating software that would—you guessed it—let people book travel online. I’d taken a chance on what I call “The Learning Door,” and things did not work out.

Roll forward a mere four years. An executive at the company I was working for called to offer me a role. There was no job description; he guaranteed only three months of employment and no real safety net. He told me upfront, “I have no idea what might manifest, but are you game to try?” Oh, and by the way, he said I’d need to pack up all my things, leave my cute boyfriend in Austin and move to Chicago.

Did the humiliation of explaining the “San Francisco fail” to friends and family cross my mind when I got that offer? Absolutely. (Honestly, the incident still stings today.) Did I go for the new role anyway? Yes.

Eventually, about twenty other people joined that project. We all laugh now because none of us on the “Chicago Project” had a clue what we were doing. And yet, each one of us willingly had chosen to jump into the “vat of vagueness”.

Over the years, these twenty people reinvented their career paths multiple times. I’d call them “Professional Experimenters,” people who can navigate vagueness while forging a path, and all the while, continue providing value to their customers. They’re an impressive bunch. I’m proud to be among them.

So what’s the lesson here? When you have the opportunity to move cities and get on a no-idea-what-might-manifest project, you should go for it? No. The “vat of vagueness” isn’t for everyone.


The lesson is that I would have never jumped on the Chicago opportunity had I not failed epically at making it in San Francisco. Not all slammed doors are dead ends. Some are beginnings.

Returning to Austin the first time had been horrible. I was ashamed to show my face. Explaining to people why I was back was painful each and every time. But what I learned from trying the San Francisco door was so valuable.


Even if I failed, I’d be fine eventually. While I was homeless and unemployed for a couple of weeks, I figured it out. I landed in a home and a job that ended up shaping my future for the better.


The opportunity to learn something new was exciting and fun for me. Yes, the initial try was an abject failure. But the experience taught me that “The Learning Door” held a lot of meaning for me—so much so that I wanted to try it again. Access to “The Learning Door” became, and still is, a core value in the work that I do.

So back to the question I got about which door to take. My answer? Experiment with intent.

Just about every business success story has a protagonist who started down one path, then learned something from customers that made them reconsider. They’d tweak and tweak and tweak the idea, learning more and more along the way. Sometimes, frustratingly, they’d head down paths that wasted time and resources. But ultimately, somewhere along the journey, something would synthesize, and the experimentation would shift into success.

Listen to any episode of How I Built This with Guy Raz, and you’ll notice this pattern. Every time I listen to one, I think about how, while I haven’t been an entrepreneur (until now), I’ve absolutely experimented with what I wanted to do with my career.

At the end of each episode, Guy asks his guest, “Was it luck or hard work that got you where you are today?”

Not surprisingly, almost every guest credits the balance of both. But I want to suggest that it’s intentful experimentation, not luck, that’s the secret sauce to their magic.

Look around at the people you admire. Did they experiment? Better yet, if you have a mentor, advocate, or advisor, find out how they experimented in their career.

If you’re intrigued at all by this intentful experimentation idea, I’d like to challenge you. Find an experiment YOU can do. No, I’m not asking you to quit your job and move across the country. Find something smaller and more manageable.

And this challenge isn’t just for those of you drawn to the “The Learning Door.” Those of you intrigued by the “Security Door” or the “Redeployment Door” can run experiments, too. Maybe it involves shifting your schedule a tiny bit to get more quiet hours. Perhaps it’s volunteering for a cross-departmental project. There’s a lot of room to get creative.

If you’re game, we’d love to hear what you’re going to do.

Click on this link and record an audio message telling who you are and what you’re going to do. I’d love to hear from you.

Intentional experimentation. It’s a thing. Let’s try it together and see where it takes us.

Xo Joanna - orange.jpeg