The Two Doors
Navigating Transitions, Defying Expectations,
and Creating a Life on Your Own Terms
There’s no faster way to fuel imposter syndrome
than giving voice to an unusual or unrealistic sounding dream.
“Ever had that moment when someone asks, “What do you do?” and you catch yourself flinching? I know I do. My career path has zigzagged from teaching to poker to summer camp and beyond. If you’re grappling with a non-traditional career or exploring new paths, you’re not alone. I’m James Davis!,Let’s dive into the unconventional and embrace the journey through Door 2. Ready to explore the road less traveled? Let’s get started”
I always flinch just a little bit when someone asks
“what do you do?”
I think it’s a reflexive response based on 20 years of rarely having a straightforward answer. In college I got certified to teach high school English. I then played poker professionally for 6 years, before making the natural transition into running a sleepaway summer camp.
When it was clear that my family wasn’t a great fit for long term country living, I helped a friend start a sports data analytics website. When COVID made that less viable, I stepped away from the business and became a homemaker, setting aside all professional work to stay home and raise my three children.
While answering the world’s most common icebreaker is rarely a good time, it’s especially uncomfortable during those times of transition.
“College has been great and all but my real passion is poker, so I’m going to try gambling for a living.”
“Uh, yeah, I play poker, but I’m thinking about getting into running a sleepaway summer camp.”
You can imagine the looks, the objections, the skepticism.
The concern on a well-meaning friend’s face who thinks it would probably be best to just do what “everyone” does - get a normal job and work it until you retire.
There’s no faster way to fuel imposter syndrome than giving voice to an unusual or unrealistic sounding dream.
So we get to pick our pain.
Door 1
Door 1 means resigning ourselves to push through the pain of working a job that doesn’t fit our lifestyle, we’re burnt out on, or bored by.
Door 1 feels safe because this is pretty much what everyone does. When you say, “I hate my job, it’s so boring,” most people will nod knowingly. You’ll be one of them. The line leading up to door 1 is long. You’ll have company there.
Door 2
Door 2 means choosing an unusual pain. Opening it involves self-reflection, taking risks, and taking steps toward dreams that will make some people roll their eyes. Door 2 feels risky because we’re setting down the “known” and trying the “unknown.”
Even walking up to door 2 feels stupid because it appears to be abandoned. There’s cobwebs over the front of it. Everyone has heard stories of people who haven taken door 2, but they sound like a sales pitch. “Walk away from your safe job and chase your dream? If you believe that, I’ve also got a bridge to sell you.”
But for some of us, door 2 is the only option. We know we need to walk through it eventually, because the alternative would drive us insane.
Door 2 is for the Undeclared.
Door 2 myths exposed!
Myth #1: There is no way to minimize risk when starting a new thing.
The first thing you’ll hear when you tell people you’re trying door 2 is how risky it is. “How could you try stand-up comedy! It’s so risky!”
These people view the world through a binary lens. In their world, your career is your identity. When my business partner at the sports data analytics company left his tenured teaching job, you can imagine the kerfuffle. He was leaving the most secure job imaginable to… run an internet website??
Don’t get me wrong - there would be really risky ways to do what we did. If we had both quit our relatively secure jobs the moment we had the idea to start that company, it would have been pretty reckless! But we didn’t. Instead, we tried on this new career by starting small. We got website hosting for $3 a month, and started writing a blog. We started making connections in the space. We tried to figure out if we were any good at what we were doing. If people cared what we had to say. If we had an idea for what to sell them. We made a minimum viable product, and it was well received. We looked where things seemed to be headed, and THEN we walked away from security and tried door 2.
Myth #2: Once you try door 2, you can never go back.
Here’s the thing. Our sports data analytics company COULD have failed. We were in a specific niche that would eventually consolidate into a few big players, and while the business still exists, it is a shadow of what it once was. What if that had happened much earlier?
Well, it’s not like all the skills and connections you build in past experiences just go away the moment you try something new. I could have found another summer camp to run. Doug could have gone back to teaching. And yes, there would have been costs in both of those cases. But it’s not a terrible fail case.
Myth #3: You’re not qualified to do a new thing, because you’ve spent so much time doing your old thing.
I really felt this one when I was trying to find a new path after getting burnt out on poker. What marketable skills had I acquired, exactly?
The thing is, I HAD acquired skills that were relevant to running a summer camp, I just didn’t know it at the time. Becoming a poker expert means accepting that you will be making the same sorts of decisions repeatedly, and trying to get better at making the most common and most important decisions. You identify the highest leverage decisions that come up most frequently, and prepare yourself to make better decisions in the future. It turns out that this skill translates very well into most things, and running a summer camp is no exception.
If you’re like me, you have something you’ve invested a lot of time and energy into. If you’ve thought deeply about anything, chances are good that the truths you’ve unearthed will apply to your next pursuit as well.
And don’t get discouraged if the thing you’ve invested time into isn’t currently fashionable! If you got really good at video games, for instance, you took some path to get there that absolutely applies to getting good at something else.
Careers don’t exist in a vacuum - the important skills in life tend to be important everywhere. Start by being curious about how your current skill set can apply to your next thing rather than being discouraged that you “wasted your time” getting good at something you’re not as invested in anymore.
Myth #4: Door 2 means going all in on one specific thing.
While my path looks fairly direct in hindsight, in practice it was anything but. When I knew I was going to stop playing poker, I took master gardener classes, volunteered at an afterschool program, volunteered as a dog-walker for an animal shelter, joined the board of the summer camp where I grew up, looked in to opening Subway franchises, considered starting a school, considered farming for a living, and probably 3 other things I don’t even remember any more.
I took all of those things seriously. When I showed up somewhere, I tried to show up with enthusiasm and positivity. I walked away from most of those things having met a few good people and learned a few new things. My role on the summer camp board wound up opening the opportunity to be a camp director, and the rest, as they say, is history.
Door 2 - It’s better together!
The coolest thing about how the world has changed since I first approached door 2 as a college graduate 20 years ago is that we’ve exposed the biggest door 2 myth of all - that walking through it has to be lonely.
I faced door 2 with Jack about 10 years ago when I was leaving my summer camp director job. We were both involved in starting Camp Stomping Ground and camp consulting together, but that wouldn’t be my path. He took that path, and I took a different one. But I can tell you that approaching door 2 with other people feels a heck of a lot better than going at it alone, and the friendship we formed during that struggle is much stronger as a result.
Undeclared is a program for people who are ready to take on the challenges of Door 2 together, with a leader who has braved the door less traveled many times.
