“I wish I had your confidence,” a friend said to me recently.


That’s funny, I mean maybe not, but I don’t think it’s about confidence (although I can see how it could come across like that). I definitely have a pattern of what you might call random acts of boldness: buying a triplex to renovate in Detroit in 2014 and run it as an Airbnb, say. Or moving to Paris by myself in the dead of winter. And a couple of years ago buying on a straight-up whim a 130-year-old shotgun house in a severely disinvested neighborhood.
The confidence comment made me think about what is really at play here. And it’s good timing; today marks a year since we sold that shotgun house I called Cherry Pop. As soon as I got the house done and we moved in, I wanted out, you see. Why?
Was it beautiful? Oh, was that house gorgeous. I know I shouldn’t say that about my own renovation and design work but I was so freaking proud of how this place turned out. It was a massive confidence boost to see what I was able to do, dreaming up the vision and executing a transformation like that.
But living there did not align with what I need, where I needed to be. And that was clear immediately. Also clear immediately: after the expense of the to-the-studs renovation investment wasn’t going to pay off financially.



But being there wasn’t right, and I felt it in my marrow. I had to cut losses and go. And being able to face it when something’s not right is what lets me take these gambles to begin with (and to keep taking them). If I thought I always had to stay stuck, pour all my energy into forcing something to work that isn’t meant to, these big things I do, the ones people seem to want to call crazy or brave, these things would eventually destroy me.
So we moved. Sold the house. And anyone who was following the saga knows I didn’t sell it for asking price. As is often the case, they may not have known the whole story.
We had multiple offers that even went above asking price, starting the day of the open house. Then an appraiser literally said to me standing in the back yard “you know where you are, right?” Banks wouldn’t lend what buyers were willing to pay. This was a painful lesson in the limitations of what I can achieve singlehandedly. Transform a house? Yes. Change the trajectory of an entire neighborhood and sway the opinions and biases of lenders? No.


Quitting something because it turns out to not be true to who you are (or who you’ve become), when nobody but you knows the whole story, comes with the very real fear of people thinking you’ve failed. I’m not immune to that. I just … don’t care. I DID try, so I don't let what people who don't try think about me guide my decisions. And I try really hard to not let what they might think contaminate how I feel about what I’ve accomplished.
I don’t attempt big things because I think I have any control over how they’ll turn out. That wouldn’t even be confidence -- just hubris. None of us, at the end of the day, have ANY control over outcomes. I do this stuff because the worst thing I can think of isn’t failure, or changing my mind. The worst thing I can think of is always wondering what if.
Sometimes I do act with haste and repent at leisure. But if I didn't have that ability to act even when I’m not sure how it’ll turn out, nothing would ever change, and I would never do anything worth doing.
What if I hadn’t gotten in over my head in Detroit and ended up learning how to fix up an old house, and set expectations in a hospitality endeavor, and how to work on an extremely limited budget, and most of all, how to build resilience? What if I hadn’t gone to Paris alone and found out that the fairytale I believed wasn’t true, but that reality was even better?
What if I hadn’t bought that house and created a beautiful new life for it and shown myself what I’m capable of doing?
I had ideas of how all those things would turn out. None of them proved to be the case. But I didn't go in with confidence that I could control what happened. I went in with faith that I could handle whatever did.