2025 Issue #15 ♟️

Happy Sunday, Reader!

Greetings from Sheboygan, where we have heard rumors about the start of spring but remain skeptical.

Candyland is the worst game ever. It's generous to even call it a game, for there is no strategy involved. I still cringe thinking about the times my kids begged to play it.

Of course, although it may feel like a modern-day torture device to torment adults, it was designed for children. It introduces the basics of gameplay: following instructions, taking turns, and counting spaces.

Eventually, we graduate to a game like checkers, which offers more strategy but is simple enough to pick up in a short amount of time.

And then there are games like chess, which are infinitely more complicated and reward long-term thinking.

As we make our way through life — not the game, the real thing — we encounter a similar progression, starting with the basics in childhood and advancing as we grow in knowledge and experience.

There are times when it feels like you're playing chess. You've got the rules down, and are confident thinking a few steps ahead. You're making great progress. After a series of strategic thinking and many well-executed moves, you're starting to feel like a Russian chess master.

Then all of a sudden, life takes a left turn.

You lose someone close to you.

The pregnancy test declares you'll soon have a new mouth to feed.

You get downsized and are struggling to find a new job.

Your doctor just delivered the kind of news no one wants to hear.

Suddenly, strategy goes out the window. Instead of dominating the board like a Grandmaster, you're getting tripled-jumped and running out of checkers. You're no longer thinking three steps ahead. It takes everything you have to get out of bed and advance even one space.

Meanwhile, it's easy to feel frustrated and resentful to be forced to play a game that seems so basic and beneath you. At least that's how I felt.

A few years ago, I was in the midst of a very long, multi-year chess match. Momentum was on my side. I was finally winning. Then a very non-metaphorical storm came along that overturned my chessboard, and with it, my family's life and finances.

The season that followed left a dried-up cash flow and a depleted savings account. It felt like I was back in the early days of my business, when our checkbook was always running on fumes and I didn't know how we'd pay next week's bills.

After years of financial success and business growth, this was a huge step backward. We were back in debt at no fault of our own, and here I was, having to get creative to pay bills and worrying about the future. I was angry, frustrated, and resentful. Just as I was finally getting the hang of chess, I found myself back playing checkers.

Heck, some days felt like I had been banished to Candyland.

Maybe this describes your current season of life. In situations like these, it seems as though no one can resist telling you what you "should" do. I don't know your situation, so I can't offer an opinion about what you should do. But here's what you shouldn't do: Keep trying to play that old game.

Sometimes life doesn't go the way we expected or hoped. Sometimes there are setbacks. Sometimes it feels like we're stuck in Molasses Swamp. It's common to feel resentful about being in the position you're in, especially if you think you should be somewhere different. I know I did.

I figured I had two options. I could be all frustrated that I was forced to play checkers. I could shake my fists and throw a tantrum, screaming, "This is not how it’s supposed to be! I am beyond this. I should be playing chess!!!"

Or.

I could choose to remain calm and play the game in front of me.

It was obvious that I currently wasn't winning anything. Being angry that I wasn't playing chess wasn't helping me win at checkers. So I let go of my long-term plans and spent a good year getting back to basics, making one uncomplicated move at a time. As our situation improved and the game evolved to allow for more strategy, I found that not only was I finally playing chess again, but I'd become a better chess player.

If you're in a season where your chess pieces got replaced by checkers, remain calm.

Maybe later you’ll get another chance to play chess, or backgammon, or something else entirely.

But for now, just play checkers and try to win.

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🤔 I wonder...what game does it feel like you're playing these days? Hit reply to share your thoughts with me, or join the conversation in the Escape Adulthood League!

Stay young and stay fun,

P.S.

Join us this Tuesday, April 15th @ 7:45 pm CT for a brand-new episode of EA Live! On the Adultitis-ridden holiday known as Tax Day, we’re reviewing highlights and handing out awards for the first-ever Festival of Shenanigans!

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