2025 Issue #41 🧑‍🚀

Happy Sunday, Reader!

Greetings from Sheboygan! A quick note that there are only a few more days to order your *personalized* 2026 Celebrate Everything calendars. They're in production, and if you help us cover the cost of the print run by ordering now, I'll personalize them with a special drawing and message on the day of your choice! (Thursday is the deadline.)

I have a confession to make.

I fully expected to marry a brunette. I was pretty vocal about it, even. No blondes for me!

In retrospect, the women who caught my eye when I was young — Princess Leia, Lois Lane, Wonder Woman — were all brunette. Most of the girls I dated in high school were brunettes.

But after I met Kim, who was most definitely not a brunette, I didn't waste any time wondering if I was making the right choice in spending time with her. I didn't delay my decision to propose because I was holding out for a brunette to come along. I didn't miss the opportunity of a lifetime because "this wasn't the way it was supposed to go."

I wish I could say I was that flexible with all my expectations.

When I graduated from college with a degree in illustration, I expected I'd make my living as a freelance illustrator. A year into that pursuit led me to realize that I really hated taking orders drawing what other people wanted me to draw.

So I shifted all my attention to a comic strip I had been developing called Kim & Jason. I expected that I'd make my mark in the world by following in the footsteps of Charles Schulz and Bill Watterson.

I put everything into it for six years. Along the way, I fell into speaking, and it started to bring in money. Way more than the comic strip. I eventually made the difficult decision to retire Kim & Jason so I could double down on what was working.

With that decision, it felt that the naysayers were proven right: I really couldn't make it as an artist. But the only reason they seemed right is that my expectations were wrong.

I once heard a talk by Fr. Mike Schmitz in which he said, "Expectations are a 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 it could be a legitimate 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.

Before I actually started freelancing, I didn't know how I'd feel creating things that didn't light me up. When I began my comic strip, I didn't realize how quickly the internet would decimate newspapers and change the landscape. And back then, I didn't know anything about the business of professional speaking.

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 and are happening now?

Maybe you can relate to this simple example. Recently, I had a wonderful, tremendously productive day that felt like a failure. One project took waaaay longer than I expected, blowing my to-do list to smithereens. 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. But it didn't feel like it.

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.

Expectations really are a thief of peace. They can ruin a day or derail our dream if we're not careful.

I believe that God plants dreams in our hearts. The details we imagine in the early stages create enthusiasm that serves as fuel to get moving. But oftentimes, those details reflect immaturity, a lack of imagination, or are limited by the fact that we don't yet have the relationships, technology, or knowledge that will eventually help us to get there.

Art was my first love; the first talent I discovered, and the one that was most nurtured early in my life. It's easy to see why I would have the expectation of making it as an artist.

But that was before I took a creative writing class in high school.

It was before I discovered a gift for public speaking in college.

It was before I realized "professional speaker" was an actual job.

And it was before I figured out that my art, writing, and speaking could be combined to create something unique and bigger than the sum of their parts.

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.

Expectations are a thief of peace.

Holding on to expectations that don’t match reality is a terrific way to go through life frustrated and disappointed.

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

The astronaut in this painting represents a dreamer.

This dreamer has always possessed a spirit of adventure and imagined a life spent exploring the unknown, pushing past the boundaries of human understanding, and experiencing the supernatural enchantment. The dreamer expected this would happen as an astronaut in the context of space.

Instead, the dreamer's story ended up in the ocean after a visit to Sea World, and now days are spent adventurously exploring the unknown and experiencing enchantment in encounters with sea creatures.

So...did this dreamer's dream go unfulfilled?

My friend Jessica has some good advice about how we should handle our expectations: “When you write that first story, print it as a draft, triple-spaced with extra wide margins. You do this because you’re anticipating edits.”

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...what's an expectation you need to revisit or release? Reply to share your thoughts with me, or join the conversation in the Escape Adulthood League!

Stay young and stay fun,

P.S.

Did you like the Great Expectations art above? The original painting sold at Wondernite, but we now have prints of various sizes in the store.

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