Best and worst decisions I’ve made

26 January 2023 | 22 Comments

Today’s post is a little more personal than professional (in fact, this started off as a post for my personal blog), but there’s still plenty of overlap into entrepreneurship and crowdfunding.

I turned 42 a few weeks ago. Ever since then, I’ve been reflecting on my life so far and how I’d like to use those experiences to grow, learn, and improve over the next 42 years (or however long I have). This started out as a list of mistakes and regrets–let’s face it, I’ve said and done plenty of dumb things over the years–but as I populated the list, I realized that there are more decisions that I’m happy with, particularly in terms of the impact on me and the people around me.

Best Decisions

Communication commitment to my parents: When I headed off to college in 1999, for reasons I don’t entirely understand, my parents were worried they’d never hear from me again. So they made me promise to write or call once a week. College boy Jamey struggled with this at first, but forming this habit turned out to be one of the best things I’ve ever committed to, as it allowed my relationship with my parents to grow, evolve, and improve despite the distance between St. Louis and Virginia. My dad passed away around this time last year, and I’m so grateful for the hundreds of hours we spent continuing to get to know each other over the phone.
Studying abroad: By far the best decision I made in college was to spend my entire junior year in Japan. Not a few weeks, not a few months, but the full academic year. I had studied Japanese since middle school, and I had an amazing time fully immersing myself in the wonderful world of Kyoto for those 9 months. I feel like it was the only time in my life where I felt the freedom to live someplace so different to where I was born and raised (not just visit or be a tourist), and I’m grateful I had the opportunity to do that in 2001.
Getting a pet: Other than a few months with gerbils, I didn’t grow up with pets. I knew nothing about cats and dogs, and honestly, I was a little afraid of them because I never took the chance to understand them. Then I adopted Biddy as a kitten from a shelter in 2007, and having this little guy in my life for the last 16 years has been such an amazing blessing. I’ve really learned how to put someone else’s needs before my own as a result of raising Biddy (and eventually Walter too). Perhaps it’s trivial to put a pet on this list, but I’ve known for a while now that I don’t want kids, so this is the closest to fatherhood I’ll ever get, which is a big deal for me.
Starting a business: In 2011 I became enamored with Kickstarter and the idea of creating something to share on that platform. It’s the type of thing I easily could have put on my “someday” list and never actually tried, but instead I committed to designing a game and making it happen. Along the way, I found a business partner (something I didn’t know I needed, but I did!), wrote a novel, and individually thanked all 942 people who backed the campaign–most of whom were complete strangers–who brought Viticulture to life. I’d always fancied the idea of entrepreneurship, and I’m really glad I took a chance at it, as I think one of the biggest barriers to doing anything is actually deciding to do it! It also helped me find my “why” of trying to bring joy and add value to others.
Quitting Kickstarter: Right up there with my decision to try Kickstarter is my decision to stop relying on Kickstarter after we fulfilled the Scythe rewards in the summer of 2016. This had very little to do with Kickstarter itself and more about the impact of selling the promise of something many months before delivering on that promise. No matter the reason, I don’t think it’s a coincidence that Stonemaier Games has been far more successful at delivering joy to tabletops worldwide since quitting crowdfunding. Or maybe it is a coincidence! I don’t know. It’s also ironic that with the Nesting Box, we learned that there are some people who actually prefer to “set it and forget it” than waiting to buy a new product after it’s available at fulfillment centers.
Publishing games I didn’t design: I designed the first few Stonemaier Games, but I soon realized that I would severely limit our potential to bring joy to tabletops worldwide if we only published my games. There are so many other designers who are talented in ways I can never even begin to approach myself. This actually started with Between Two Cities, My Little Scythe, and Between Two Castles, but I have to acknowledge that developing and publishing Wingspan by Elizabeth Hargrave is one of the most impactful decisions I’ve ever made (on me, Stonemaier Games, and millions of people around the world). I’m forever grateful that Elizabeth gave me the chance to work with her to turn Wingspan into the game it is today.
The choice to floss and exercise every day: A long time ago I heard that people who don’t floss will someday lose all their teeth. Whether or not that’s accurate, it didn’t sound fun to me, so I committed to flossing every day, and I’ve done so for the last 23 years. Similarly, throughout most of my 30s, I spent a lot of time sitting at a desk, and instead of playing soccer or working out a few times a week as I had in my 20’s, sometimes weeks would past without any substantial physical activity. The impact on my body was incremental, so I didn’t really notice until, well, I noticed! A friend gently encouraged me to find a way to reincorporate 20 minutes of exercise into my daily routine. So I started taking a little break from my 12-hour work days to lift a few weights, focus on my core, and run up and down the stairs in my building. I also added a weekly activity out of the house (indoor rock climbing at first, then disc golf). This small change has had a hugely positive impact on my health and wellbeing.

Worst Decisions

As I mentioned at the beginning, I’ve made many bad decisions in my life, decisions that hurt me and others. The brevity of this part of the list is not intended to downplay those decisions or the harm they caused in any way. In fact, I tend to dwell on even the smallest bad decisions over the course of my life more than I reflect on the positive.

But when I look back at most of the decisions I most regret, I actually see a lot of good things that ended up emerging from them (and hopefully more to come). You may disagree, though I truly hope for anyone out there that your worst decision list is shorter than your best decision list.

Signing a bad mortgage: When I was in my mid-20s, I bought a small condo (this was around 2006). I had a steady job making around $40k/year. When I was presented with the mortgage documents, the lender mentioned that there was a variable rate that could go up or down and that there was a prepayment penalty–they brushed over these elements (which are now viewed as predatory and a big reason for the recession of 2008) as if they were standard practice. I thought they sounded a little odd, and I should have called my dad to get his thoughts. But I didn’t. I signed the mortgage, and the financial implications over the next few years (surprise: the rates went up, not down) were really bad. I was fortunate to turn things around by eventually accepting the prepayment penalty and refinancing to a fixed-rate mortgage, but it took me years to break even.
Not committing to a partner: I’ve always romanticized the idea of romance–I’m the type of person who cries in any romantic comedy when the main character realizes they’ve found their person. I don’t think this has had the healthiest impact on my romantic relationships, though, as I either (a) felt like something was missing if I wasn’t swept away by a girl or (b) if I was swept away by a girl, I felt like I was giving up on other creative pursuits (writing, game design, etc). It wasn’t until I was 38 that I realized that if someone (Megan) chose me, I could choose her too and continue to choose her every day.
Any time I’ve ever acted out of anything but love, kindness, and compassion: This includes a lot of bad decisions within the same category, but it’s an important one to me, because these are the choices that eat at me the most. Why would I ever punch down when I could lift up (or not say anything at all)? Why would I ever exclude when I could include? Why would I spend my time and energy talking about what I dislike when I could share something I love? It’s when I’ve broken from these principles that I’ve felt the least like myself.

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Does any of this resonate with you? What are a few of your best and worst decisions? I’m sure I’ve missed some big ones here–I may update this list over time.