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.
***
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.
Also read:
- Top 5 Mistakes That May Sink Your Crowdfunding Project
- The 7 Mistakes Crowdfunders Make the Day Before They Launch
If you gain value from the 100 articles Jamey publishes on this blog each year, please consider championing this content! You can also listen to posts like this in the audio version of the blog.
41 Comments on “The 10 Best and Worst Decisions I’ve Ever Made”
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Last year I purchased Wingspan Asia, then Libertalia (after playing it at the convention), then Expeditions Ironclad Ed. A couple of days ago I was given Fan Art Pack as a late NY gift. Great games, all of them shipped and delivered through I don’t know what. I don’t think your decision to cut your Russian audience off your product is made out of love, kindness, and compassion. Why would you ever punch down when you could lift up (or not say anything at all)? Why would you ever exclude when you could include?
Our decision to not contribute tax dollars to a military that is actively invading another country is very much made out of love, compassion, and empathy…for Ukraine. I also empathize with the people of Russia who do not support the effort to conquer Ukraine, and I greatly look forward to the opportunity to work with our Russian localization partners when Russia halts the invasion (and hopefully pays for the recovery costs for the damage they’ve done).
I’m not punching anyone, but sometimes we need to speak up for those who don’t have a voice, especially in situations of oppression and destruction like this. I very much wish there was a way to include people in Russia who don’t support the war. Are you among them? I appreciate your support of our products, which indirectly supports Ukraine, as we have continued to work with localization partners in Ukraine.
Thanks for highlighting this one again as I had missed it! Great read, especially the “whats your why” part and the bad decision on acting on not following compassion. These are really valuable reminders.
Love that you could, and would, share this with us. Appreciate what you do.
[…] The 10 Best and Worst Decisions I’ve Ever Made: This was probably the most helpful article for me to write this year, and I’m glad it resonated with others too. The list features 7 good decisions (like my commitment to consistent communication with my parents and my choice to study abroad in college) and 3 bad decisions (a bad mortgage, a lack of romantic commitment, and any time I’ve chose to act out of anything other than love, kindness, & compassion). Interestingly, the article may have gotten the most traction for a comment from a stranger who was 100% convinced that my disinterest in having children is a massive mistake. […]
Jamey, this list was helpful but also really got me a bit emotional. The mortgage decision I know was weirdly specific but I was in a similar boat. My husband and I bought at house in 2011 when we were only 23 and a lot of that was due to perceived pressure and not what we actually needed. We ended up having to sell 3 years later and didn’t quite break even. It bothered me for years and years and made me nervous to make any big decisions at all. Reading things like this is so assuring because I often assume people I look up to, like you, aren’t making these kinds of dumb mistakes and that’s why you are successful. I noticed quite a few leaps of faith in your best decisions list too – it’s good to be told again that at some point, we all have to make big decisions that could go wrong, and that’s usually the only way you meet your big goals in life.
Thanks for this blog. Your thoughts are very helpful to see written out. I’m proud to be a Champion and Ambassador here!
I appreciate you sharing this, Kendra, and I’m sorry you had such a rough experience with your first home ownership. I can definitely relate to that, and to be honest, I’ve made plenty of dumb mistakes–I just try really hard to learn from them, not repeat them, and share them so others can avoid the same mistakes. :) I hope you have better fortune with your next big decision!
This was a wonderful post. It paints a picture of you, and there’s a lot of virtues and strengths included here that explain why you got to be where you are. Wonderfully revelatory and insightful, thx:)
A remarkable post, Jamey. I have read so many of your blog posts over the last few months (trying to figure out KS and other related stuff), I have never been moved to leave a comment until today. As I sit here reading things that make me happy or excited because they are game related, your post made me stop and think of how lucky I am to have landed here – a place where my worst fears are about shipping costs and my dreams don’t have to include simply being safe, fed, and healthy. Your last note about acting out of love, kindness, and compassion really hit home – what possible reason would I have to act out of anything other than those? What possible reason would I have for wanting to make someone’s life harder, or to feel bad in any way? It is such a simple way to live life – make others’ lives easier, make others’ have a reason to feel good, to smile, to laugh. Thanks for the reminder to keep it all in perspective and simply share the joys in life with others.
Thanks so much for chiming in, Anthony. I absolutely resonate with what you said about love, kindness, and compassion. I think the human in me doesn’t always act the way I want–that’s the challenge. But it was helpful for me to write down what’s really important to me as a reminder, especially for those moments of weakness and vulnerability.
The last one really resonated with me. My ex-girlfriend always used to say that because of my kindness, i let people walk all over me. But i decided to prioritise kindness and it’s truly one of my core values. And I surround myself with people I know will not take advantage of that kindness. (And I dumped that girlfriend and found a girl who loves my kindness and then I married her and I will continue to be kind to her until the day we die (or until she breaks any of my boardgames) :p!
Tom: I really like this, particularly the combination of choosing kindness and choosing friends/partners who don’t take advantage of it.
I was waiting to read the board game you designed that you had the most conflicted feelings about.
I have a video kind of along those lines here: https://youtu.be/P3P70PrE8i4
Yep, definitely resonates.
One of my best decisions was marrying my wife. She helps me become a better person, and I try to do the same for her (which indirectly helps me to improve, as well). I also romanticized a lot of stuff, including romance, when I was young; but I’d personally rather have a real woman with real love over the *idea* of something any day.
Worst decision might have been not taking fitness seriously enough until mid-way through adulthood. I found out the hard way that for me, it’d have been easier to avoid losing fitness than it was to get it back. Count Rugen said, “If you haven’t got your health, then you haven’t got anything.” — which to me is one of the top 10 pieces of movie-quote wisdom ever.
Others’ mileage may differ, of course.
Thanks for sharing this, Chris–this resonates right back with me! :)
I just turned 40 last week and I’m myself trying to find the next chapter in my life and find ways to be around for it as well lol. I just got a new dog last year, a rescue pitball who has taught me just how unfair preconceptions can be. She is the kindest, gentlest, and smartest dog I’ve ever had. Fiercly loyal but not an aggressive bone in her body. I try to keep that in mind when I approach people or even situations.
I’ve also experimented with so many things in my life to try and find my passion. For the longest time, I was trying to find a way to be a writer. I did stand up/improv/self published a book. I have all this experience from that but that little voice in my head keeps telling me anything I will try will fail and to quit. I want to start doing board game design and a podcast exploring what I love and want to learn in this field but it’s so hard to keep that beast at bay especially at the beginning.
I feel like as I get older, it gets harder to fit that feeling that you’ve missed your shot.
But on the plus side, I’ve moved to a new place to leave negativity behind and I hope to use a similar mindset to you in my work and my private life.
Anyways, I’m digressing. Thank you for sharing your story and hopefully in a year from now I can enjoy more of your journey and hopefully I can also say that I’ve moved forward in a meaningful way in my goals and not let the voice be right.
Thank you for sharing, Tony, and happy birthday! I can understand the fear of failure and the feeling that it may be too late. One thing I mentioned in a post earlier this year is that a framework I find helpful for creation is to frame failure as an absence of creation, nothing more. That is, it isn’t about your game being good or published or a best seller; it’s about you putting in the work to create a playable version of the game. There is still the chance to fail, but it’s entirely in your control: You either create the game or you don’t. Everything else is just a cherry on top. :)
Since you asked…
Worst:
1. Arguing with my wife (the bad kind) in front of my child. Never do this. An imprint is left and I can never erase it.
2. Not having a stable job and not having enough money to help my mother while she was dying. Those were the darkest years of my life.
Best:
1. After my mother died, I accepted defeat for my “passion” job (art director), and went back to school to focus on a more lucrative career (software). After 3 years of intense study and humility, at the age of 43, I was able to find an excellent job, erase 10 years of debt, pay back my school loans, and become somewhat financially stable. I now preach how no one is too old to study and re-train for a new career.
2. Buying a house. 30 years of renting was a massive financial and emotional drain. Buying a house, where the mortgage was less than our rent, finally left me with financial stability I had dreamt about for years.
3. Rejecting religion. For years in my youth, I was conflicted and confused from heartless Christian rhetoric. Once I realized religion was only one perspective to view life, I could more clearly see how I fit into this world. Herman Hesse’s Siddhartha helped me see a perspective I’d never seen before. (I realize this isn’t for everyone, but for me religion was hurtful.)
Adam, thank you so much for sharing your list–I appreciate your vulnerability. I’m really sorry to hear about those dark years, and I hope you’re in a good place now (it sounds like it from your Best #1).
Excellent post. I’m nearing 63 and I can tell you that #3 under Worst is the most important thing.
Thank you, Roger. I’m inclined to agree with that–a lot of the others connect back to it.
This is a beautiful post. Thanks for sharing.
Thank you, David!
I imagine when you are older you will realize that not having children was your #1 worst decision.
Or, if you care about the impact of anthropogenic global warming on the planet, it is your #1 best decision ever. Why people feel the need to breed or encourage others to breed is beyond me. Most people aren’t capable of taking care of themselves properly, much less another human being.
I really find both this comment and this reply troubling.
For some of us, having children is an absolutely wonderful experience, and I can see where someone who is in that boat would think that not having children will be a big regret. But has this person really been so lucky as to never come into contact with children whose parents feel they were a mistake? Have you not seen what that does to a child?
On the other hand, framing the choice of children in environmental terms I find to be a red herring. The climate problems that we have caused are too big to be solved by the adults of today. We can (and desperately need to) do more work that direction, but we cannot finish that work and there will be a burden passed to future generations. If we truly care about the planet long term, we need those future generations to understand these problems and their importance and be willing to work on those solutions. If environmentalists stop having kids, who does that leave in those future generations?
As to the original post, I love the underlying theme of the value of taking care of yourself _and_ taking care of others. :)
That sounds a lot like you’re just pushing the problem to the next generation which is really irresponsible. Issues that humans have created can be fixed. But we’re too selfish because we want everything now. Not having kids and reducing the human population is one of the best ways to reduce human waste. But clearly we’re too selfish to even do that.
I feel pretty old at 42, and I’m much happier with my life and the impact I’ve tried to have on others by simply being a father to 2 cats and an uncle to 6 little kids. We’ll see if my thoughts on that change over the years–it’s certainly possible–but I think we might just be very different people in those regards, Jack.
What if he had kids and figured out it was the worst decision and it wrecked both his and their lives ?
This is, best I can tell, a rather interesting assumption. Not all people need children to fulfil their lives. Not all people want children. And I know many who feel this way and are quite happy in their lives. You do you, Jamey.
+1
How is this a helpful comment? Are you acting out of kindness or compassion when wishing or predicting regret upon a person? People have many reasons for choosing not to have kids. I have two young children, and it is extremely difficult sometimes. Of course I love them very much and couldn’t imagine my life without them now, but I also recognize the profundity of the decision and would never fault a person for acknowledging that and deciding against it.
It is profoundly selfish to think the way you’re describing. The thought that someone might have kids for fear of regretting not having them is astounding. You don’t know anyone’s reasons for choosing not to make this decision. There are countless valid reasons, and it is arrogant and presumptuous to say something like this. And it is certainly not kind.
This comment has spun a conversation that has begun to deviate far from the topic of this post, and I’d ask that we move on from this thread (if it continues, I’ll just delete the comment and all responses with it). While the post is about MY best and worst decisions, the discussion topic is YOUR best and worst decisions.
Please keep in mind the commenting guidelines on this website: “Antagonistic, rude, or degrading comments will be removed.”
Jamey its not easy for a person to see and say out loud what bad decisions he/she made, and even by doing so that moves you forward.
Thank you.
Well said, Jordan. I’m always trying to learn and grow to the best of my ability.
Such a great post! I’m a gamer at heart, but the points that hit home for me most were #2 and #3 under worst decisions. However, waiting for the right person for me was the best decision ever. In my thirties, I really started thinking that “movie” love was just a pipe dream I was chasing and that it just didn’t exist. And then I met my wife (18 years strong so far). I can’t even describe in words what the connection is, I think it’s a bit different for everyone. But I’m just glad I found it. And I totally agree on the third point… I like myself the least when I act in any way that is not kind. I try to learn and be better every day, mainly so I can look in the mirror and see someone I admire. Maybe one day I’ll get there.
Definitely appreciate this post. Like everyone, I also have a list like this, but I find some of the worst decisions have definitely set me on the path to the best ones.
One particular thing I need to work on is the habit of not acting on those creative urges to write a story or design a game, etc. I’m only in my early-to-mid thirties, but with my second just having been born, it’s had me thinking a bit more about these things.
Thanks for sharing that, Daniel. I agree about how some really bad decisions have changed my path for the better. I hope you find a way to tap into the desire to create!
This is good. Thanks for sharing, Jamey.
Good decision? :) Thanks, Wes!