2025 Issue #9 ☠️

Happy Sunday, Reader!

Greetings from Sheboygan, where I am thrilled to be back in the studio painting after a busy (but awesome!) run of speaking engagements.

Recently, I had a wonderful, tremendously productive day that felt like a failure thanks to one crucial mistake.

It’s a mistake you and I make all the time.

I’ll start by saying I find it incredibly helpful to plan my day the night before. As I’ve gotten older, my approach has gotten wiser. Rather than trying to squeeze everything into unbending blocks of time, experience has taught me to build in breathing room for the inevitable swerves that arise.

Still, some days never have enough breathing room.

On this particular day, one project took waaaay longer than I expected, blowing my plans to smithereens.

The thing is, although some tasks got pushed to another day, I accomplished a few other things I hadn’t planned and took advantage of the unseasonably warm day to enjoy an invigorating walk in the sunshine. It ended with a delicious dinner with my beautiful bride.

By all objective measures, it was a very good day.

The thing that soured it?

My expectations.

The day simply didn’t line up according to the timing and order of my expectations. Because some to-dos were left unchecked — even though other great elements were added — somehow it felt like I failed.

This is not a cautionary tale against planning or a list of pro tips to bulletproof your plans. It’s a reminder that it’s hard to appreciate accomplishments when they are in the same room as even one unmet expectation, one missed goal, or one unforeseen event that was out of your control.

In the battle between reality and expectations, reality is undefeated.

I began to ponder this phenomenon when I heard someone claim that expectations are the thief of peace.

I recoiled at the idea at first, because I associate expectations with hope, and hope is good. If expectations are the thief of peace, is the antidote to become a pessimist? Lower the bar? Settle for mediocrity? Slack off? That seemed less than ideal.

Then it occurred to me: An expectation is a prediction.

It’s a prediction about what you think — and maybe even hope — will happen. Sometimes it’s little more than wishful thinking, but more often it’s an educated guess with actual data to back it up. And sometimes your prediction is correct and your expectations are met.

But it’s still a prediction.

One you might be making with a wildly insufficient lack of information.

Take a quick review of your life right now. How much current frustration, pain, or sadness is the result of circumstances turning out differently than what you expected?

Is holding on to what didn’t happen keeping you from appreciating all the great things that did?

Here’s an example that’s bigger than one day. Like many people, when I was a young adult I expected my career to go a certain way. It went a different direction, filled with opportunities and experiences I didn’t even know were possible when I was an 18-year-old kid. But thirty years ago, if I had been given the choice between my original expectations and a full picture of how my life turned out, I’d choose my current reality.

Every. Single. Time.

And yet, here’s the crazy part: because it doesn’t match up with my original expectation — you know, the one I had when I was a naive, inexperienced teenager — I am sometimes tempted to wonder where I went wrong.

Bye, bye peace!

Here’s another example. One winter, instead of taking what had been our traditional trip to Florida, we decided to save money and take a staycation instead. A time of hibernation that included playing games by the fire and watching movies under cozy blankets turned out to be exactly what our family needed that year. But it was a struggle to appreciate the gift because I was tempted to sulk over unmet expectations (that we’d go to Florida every winter!)

I may be a slow learner, but I’ve discovered that holding on to expectations that don’t match reality is a terrific way to go through life frustrated and disappointed.

Expectations really are a thief of peace.

When we become resentful of missed expectations, we are in danger of also missing other opportunities and blessings we didn’t see coming.

Letting go of expectations is not about being pessimistic. One can be optimistic without becoming a slave to expectations. My optimism is grounded in the fact that God has ALL the data, loves me more than I deserve, and tells the best stories. We can make plans and hope for things to go a certain way, while still holding loosely to them, trusting that God may have different (and better!) ones.

If you want more peace in your life, don’t abandon hope.

Don’t stop striving for greatness.

Just stop putting faith in your predictions.

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🤔 I wonder...after reading this, what's an expectation you can finally let go of? Hit reply to share your thoughts with me, or join the conversation in the Escape Adulthood League!

Stay young and stay fun,

P.S.

Are you infected with a winter strain of Adultitis? Get ready! The first official Festival of Shenanigans is coming on March 17th. The ultimate Adultitis fighting challenge is going to be the silliest seventeen days you ever did see. (And you could win a year's worth of ice cream!) More next week!

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