Everyone asks me to write things for them. In fact, it was the question I get asked most often until the last few years when the top spot was replaced by, “what’s your plan?” I know it’s code for curiosity about how I’m navigating a nomadic life. They want to know if van life feels as good as the pictures look on Instagram. 

Sometimes, the question is filled with their own fear. Will you settle down soon? When will you get tired of this? This comes from that place where most people associate “nomadic” with “homeless,” and technically they’re right. I don’t have some home to go settle back into. I’m not operating with a 10 year plan. The whole idea is scary to them. Which, me too. 

I’ve never been asked so often about my plan until I gave up on having one. Growing up, I always had a plan. From the age of 6 or so, I knew what I wanted to do when I grew up (doctor) and where I would go to college (Harvard). The direction changed a bit before I actually went to college. 

When I started college, I still didn’t have any idea what all this money and time would add up to. I was doing what I was supposed to do, or at least that’s how it was sold to me. Hell, I didn’t even want to go to college. I did all the things I was supposed to do. I got married, moved to a big city for a big name job, and bought a house. Still, the only constant were the changes to my big plan. I lost my job in the big city, the marriage ended, and suddenly I felt stuck in this beautiful home that was all I wanted at one point. 

When my plans turned into a burden it fucked me up. Those unpredictable changes to my plan made me more scared to stray from the plan in the first place. I couldn’t imagine doing anything wildly different. I just kept chasing everyone else’s dreams. I found myself taking the same big name jobs with the same narcissist managers and wondering why I wasn’t happy at work. Getting married again even when I wasn’t right with myself yet. The list goes on. 

It took extreme exhaustion with a side of soul crushing behavior from a manager to snap me out of the cycle. I had 0 interest in starting a business, and 0 plans to start one, either. I quit my job without a backup offer in hand. I had never done that before. I always had a plan. Now I had no idea where my next paycheck was coming from. As much as living a nomadic life might be scary to some people, quitting my job was far scarier. Everyone was asking me about the plan. I confidently answered every time with whatever bullshit I could muster to interrupt myself from blurting out that I had absolutely no clue what I was doing. 

I still don’t know what I’m doing most of the time, but here’s what I do know. Not having a plan won’t kill anyone. Risks won’t either. The way I see it, the only guarantee is that things change: You. The work. The world. You have two choices. You can do what everyone’s doing or you can be more nomadic about your plan. Allow yourself to float toward what’s right instead of responding to the tug to do something “normal” every time they ask, “what’s your plan?” You have no idea what will happen when you stop trying to fit in and just try to be happy. 

Weekly Letters life plan