For 28 years I ran a pretend baseball team in a simulation baseball league that used a tabletop baseball game (charts, cards, and dice) and all I have to show for an effort that spanned more than half my life is this blog post.

The Internet Baseball League was a hobby that consumed my life for almost three decades. I find it very hard to explain to people who are not competitive by nature why I did this for so long. I wanted to win. I wanted to prove I was smart about baseball, smart about building a team, smart about playing. This part of my personality has caused multiple blowouts in my personal life, and has come up when playing Magic: The Gathering as well. I eventually had to stop doing any kind of "competitive play" with Magic too because it was turning me into a raging lunatic.

In this post I wanted to take a deep dive into this particular hobby, and show you how a person who thought they were good at something turned out to not really be good at it all. I got stuck in a loop I was only starting to break out of but decided to stop doing it because I was miserable.

At the highest level to look at this hobby, you are running a baseball team through an entire season. You are competing against 23 other people in a scenario where only one person wins the very last game of the season.

If you zoom in a little bit, it really is a simulation revolving around long-term resource acquisition and resource management. Can you identify players who can help your team? Once you have those players, can you use the rules of the game (and rules surrounding who you can and cannot keep on your team) to win more games than you lose in pursuit of a league championship season?

As I write this, I finished the last games of our 2025 regular season. I ended up going 87-75, but likely finishing 4th and last in what is the hardest division in the league. With the end of this season, I missed the playoffs in 10 of my last eleven seasons (last made it in 2020).

In 2009 I made it all the way to our World Series. I lost in 6 games. Since that time, I made the playoffs an additional 4 times. I only won one playoff series in that time. 16 years of being incredibly mad at the end of every season. I would print out the cards we use for the game every years and when the season was over, I would angrily dump them in the garbage and tear up the rules. I wanted to win. I could not accept the constant lack of positive results.

For many years my wife asked me why I did not just quit if the experience was making me unhappy. I never had a good answer other than "I want to win". Which is what it really was. It was a selfish answer.

So where did it all go wrong? Why was I never able to get the results that I wanted? I'm sure there is enough here to make a therapist wealthy but I will attempt to explain what I think happened.

I believe I failed at the resource allocation stage which caused any opportunities to have successful resource management to be few and far between.

One strategy for roster construction is that if your team is not already a "playoff contender", you are better off focusing on "resource acquisition" than "resource management". In the league it means acquiring players who have a "bad card" in the year you play but will have a "good card".

After losing the division title in the last week of 2016 I decided to try and "build a better team" by committing to a plan as described above. If the team wasn't already a contender going into the season, spend that year trying to improve the roster and focus on the next season.

That culminated in a series of 3rd and 4th (out of 4) finishes in the division and a wild card playoff spot in 2020 where I went 94-68. 4 years to make it back. My team had multiple players drop from being good to being mediocre, and we were back in the "resource collection" phase.

Given how talent enters the league, for your team to remain good you can only have a few holes on your roster every year. Need a new CF? You can probably get one via our "first card and guys teams could not keep" draft. Or maybe you trade some excess talent you have for something you don't have.

My issue became that, for a variety of reasons, I always had more holes to fill than I could replace via the draft. When you draft players, you are getting prospects (for the most part) and it can take several years to see if who you picked becomes a positive contributor. In my case, I had several picks turn out to be duds. Pitchers who did not develop. Position players who turned out to not have what it took to be positive contributors in the optimized player pool that exists when you have 30 teams worth of players but only 24 rosters to fill. When core players on your team become bad, replacing them while also keeping the talent level going becomes difficult.

Trading is another way to fill those holes but I never had enough "extra" to trade to fix things and because my teams were bad, I would be giving away draft picks to another team that could be used to draft building blocks.

I got stuck in a loop.

So, every year became "oh well, I guess next year is the year to try" from 2021 onwards. But I never got to the point where it was time to shove hard, trade away some future, and make a run to be a playoff team. In both 2023 and 2024 I thought I had teams that were on the fringes of being a playoff team so I felt I would play the games and see what happened. "Your team looks pretty good" was something I heard a lot. Instead I finished 73-89 and 81-81.

I'd finally had enough of my own inability to generate good results despite what I had been told by other people was the "correct process". Being results-driven is hard, but in a league where we are counting wins and losses, I just could not avoid being angry at the outcomes.

So at the beginning of the year I decided this was going to be my last year. I felt I had a team that was close to being a playoff team. I used my best draft pick on one of the best prospects in the game at a position where I needed help but their current card in the game would be terrible.

"Let's play it out and see where we are after the first third of the season" is what I said. If I felt I was still in it, then I would shovel some resources into improving the team and make a run for the playoffs.

After week 8 of 25 of our season, I was still in it. I traded away my two best prospects to try and patch holes. I grabbed a great starting pitcher, two outfielders, and some bullpen help.

The chase was on. Then the team stumbled hard. I had a stretch where I lost 13 of 18 games and that was it. I got as close as 2 games out of a wild card spot. I had one of the league's best offenses for most of the year. In the end, variance and inexplicably bad luck with my pitching pushed me out of contention. 13-22 in games decided by 1 run is how I ended up missing the playoffs as well.

It was a terrible end to a long participation in the hobby. I spent the first 14 years trying to figure out how to win in the league. I spent the next 14 years chasing that and failing to develop pitching good enough to contend while always having too many holes to fill on an ever-changing roster. There are people in this league who are really good at this. In the end I was not good at it.

I ended up managing 4600 games in this league. I went 2141-2455 in them. Roughly half the time I finished .500 or better. The times I didn't my teams were very bad. I could never figure out how to win consistently in this league and it stopped being fun a long time ago. I hung in there in a misguided attempt to "make it work".

It didn't work. I'm very sad that a core part of what I did for so long turned out to be such a misery-inducing failure for me.

When I announced to the rest of the league I was leaving (just after our trade deadline so any deals I made would not be suspect) I got some nice emails from people telling me they understood why I was leaving and thanked me for helping them over the years.

That was nice but there is a big hollow part of me now. I clearly cannot fill it with other competitive hobbies because it will lead to the same outcomes from where I sit now.

Thanks for reading all the way to the bottom of this post. Learn the lesson that took me too long -- a hobby that you no longer enjoy is now a job. Your hobbies need to have positive outcomes to them, or else they are just a job. Something you resent doing. Something your loved ones have to hear you angrily complain about.

I am mad at myself for subjecting my friends (and league members) to my unhappy rants about my team. I wanted to win. I couldn't figure it out. Leaving is the only way for me to break that loop and try and pour the energy into wanting to succeed into other hobbies where I can have a much healthier relationship with them.

Failure at something you really want to succeed at hurts. It is never eased by being reminded "it's just a game". It wasn't just a game. I ran the league for a decade. I build the league web site. I even helped build the game we use.

In the end, all I have is this blog post.