I recently re-watched Moneyball. I remembered not really enjoying it the first time, yet it gets referenced often enough in popular culture that I felt it was worth revisiting.
I’m glad I did. This film is absolutely heartbreaking. Spoilers ahead.
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Billy Beane is the GM of the Oakland Athletics. He doesn’t have the budget to outspend his competitors, so he uses metrics other teams largely ignore to identify undervalued players and build a competitive team.
Oakland has incredible success during the regular season but loses in the first round of the playoffs. One of the large-market teams recognizes the value of Billy’s methods. They offer him enormous money to bring his approach to their team. He turns them down. He doesn’t win a World Series, and the team that wanted to hire him does in short order.
The final scene of the film is him listening to a recording of his daughter singing a song. And while it’s not explicitly said that he gave up the job in Boston to stay closer to his daughter, it may have influenced him. If we look purely at his resume from that point forward, life does not reward him for his choice.
He ushers in a revolution to the sport he loves. Yet never gets the payday, and never gets the championship. Damn. This is heartbreaking. And likely why I didn’t enjoy the first watch. I was too young, I didn’t know what I didn’t know.
Before you’ve had the experience to try something you believe in and work through challenges in a way you can be proud of, it’s hard to appreciate that the quality of your effort does not guarantee your desired result.
When I was operating my massage practice during the pandemic, I made sure I never sacrificed the wellbeing of my staff for my own benefit. It’s easy enough to do. Fire some people, cut back on payroll expenses, life goes on. But I always saw the staff as people. People with children to support, mortgages to pay, people who believed in me, trusted me to provide a stable environment for them to earn a living.
Those decisions contributed to my current debt. It cost me most of what I had built up until that point. My marriage failed. The business failed. I had to start over.
So I can’t say that those decisions were wise. Far from it. And in the end everyone ended up being let go anyway, which was what I desperately fought to avoid for so long. The question I so often come back to is: was I wrong to do it?
There is a scene at the end of the movie where we see a player hit a home run and not realize it. He rounds first, stumbles, and scrambles on the ground to get back to the base. He’s panicked, thinking the ball is still in play and terrified of being thrown out.
It turns out, he hit a home run.
I’m at a chapter in my life where I get to rebuild. There are often thoughts where I think that I need to right all the wrongs, redeem myself through impressive achievement and persistence.
Pay off my debt as fast as possible. Make savvy financial choices so I’m on pace with my peers at retirement. Make income from my writing to justify the time that I put into it. Grow my business to the point where I again have multiple staff and employees. Sell the business. Transition into a new career that provides me the same freedom and flexibility that I am currently experiencing. Get married. Raise kids.
How different are those from winning a World Series? Becoming the highest paid GM?
And is there still value in the efforts that define my life if I never get the outcomes that I’m striving for? Or is it all for naught?
I failed five people the day I closed my business. And I tried my hardest to avoid that outcome. I don’t think the decisions were sound. They didn’t support the long-term growth of the business and they didn’t consider my needs or boundaries.
But now I say no in my life. Because I know the cost of saying yes. It’s so much easier to be agreeable in the moment. And so much more heartbreaking to finally accept the consequences of all the moments when I didn’t. That pain is so deep, so terrible, that I feel a lot better about the small discomfort created by setting a boundary.
I would not have that wisdom without the “failures.”
So maybe 10 years from now I’m not married. I don’t have kids. My career has changed and I have less freedom. Discover Wellness closes without selling. I still have less than 50 subscribers and no revenue from writing. I pay off my debt but have no retirement savings despite being in my mid-forties.
Did I fail?
Maybe.
But maybe I was true to myself. Maybe I’m doing meaningful work. Maybe I’m in a committed relationship where I’m honest about my needs and I don’t overcommit myself. Maybe I laughed, watched the sunset, and rested when I was tired.
Maybe I looked up from the base in front of me long enough to see the ball go over the fence.
If this resonated, share it with someone who might need it.
Thanks for being here.
Jack
P.S. I’ve been thinking a lot about pressure and freedom lately.
I recently published a short essay called The Freedom Paradox.
It goes deeper into some of what I’ve been working through.
eBook + audiobook here:
https://jackjohnstonwrites.gumroad.com/l/freedom-paradox


