I am a professional reminder-er and permission granter who moonlights as an artist, author, professional speaker, and publisher of The Adultitis Fighter, which helps people create lives filled with adventure, meaning, and joy. I enjoy Star Wars, soft t-shirts, and brand new tubes of paint. My wife Kim and I homeschool our three weird kids and live in Wisconsin, where we eat way too many cheese curds.
Greetings from Sheboygan, where I recently stopped at a lemonade stand, because that's my rule. They also had freeze pops for sale, and I bought one because it had been years since I had one. As I was enjoying it, I was reminded of this painting, and thought it would be worth sharing the story behind it this week, because it's a reminder we all need to hear every so often.
Speaking of reminders, I remembered that Rachel shared an Adultitis Free News segment about how freeze pops are made, which was quite fascinating and reminded me of the segments on Mister Rogers' Neighborhood when he would visit factories to see how things were made. And finally, I wanted to remind you that this art is one of four timed-release Mini*Prints in our Summer Collection that will only be available for a few more weeks.
Now, I like to think of myself as an optimistic person. After all, I am a lifelong Cubs fan who always believed in the hope-filled power of next year. Then again, when they lose three games in a row, feeling certain that they’ll never win another game again seems pretty pessimistic.
The truth is, I’m probably a little bit of both.
The optimistic side of me believed that Penguins Can’t Fly would be a New York Times bestseller. It wasn’t.
This defeat, along with several other epic failures in my career, bolsters the popular argument that I should minimize the risk of pain and defeat by keeping my expectations low.
This strategy of operating with low expectations is employed by many. The thinking goes that if you don’t get your hopes up about something, then you won’t be as disappointed if it doesn’t work out. And if it turns out well, you’ll get the enjoyment of being pleasantly surprised.
As it turns out, it’s a flawed strategy.
According to neuroscientist Tali Sharot, people with high expectations always feel better because how we feel depends on how we interpret the event.
When a person with high expectations succeeds, they attribute it to their own traits. When they fail, it wasn’t because they were dumb; it was because the exam was unfair, and next time they’ll do better. When a person with low expectations fails, it was because they were dumb, and if they succeed, it’s because the exam happened to be really easy, and next time reality will catch up with them.
Secondly, regardless of the outcome, anticipation makes us happy. It’s why people prefer Friday to Sunday: it brings the anticipation of the weekend ahead.
Finally, optimism acts as a self-fulfilling prophecy. Believing we will be successful makes us more likely to be so, and optimism reduces stress and anxiety, leading to better health.
When a container is at 50% capacity, it is half full.
But technically, it’s also half empty.
Both are absolutely correct assessments of the container in question.
If the label you give it is completely subjective, I say go with the one that gives you the best chance of going somewhere beyond what you thought was possible.
So many of our life experiences could be seen in the same light. We lose a job. We break a leg. We get dumped by the one we thought was The One. Is that unexpected, unwelcome thing that just happened in your life an obstacle or an opportunity?
Yes.
Both are absolutely correct assessments of the event in question.
Deciding what you call it can make all the difference.
Was Penguins Can’t Fly a failure?
Upon further review, believing it had a chance of being a bestseller led me to put in a lot of effort. It pushed me to think of new, creative ways to promote it, and it got me out of my comfort zone by asking for help. All of these things made a difference. No, it wasn’t a NYT bestseller, but three printings later, and after having outsold my advance (something most published authors never do), it was a success.
It turns out that optimism is attributed to that success. Without it, I would have always wondered what might have been.
I don’t know if I’m naturally optimistic or not. These days, even though I still feel fearful about getting my hopes up only to have them dashed, I’m realizing it’s more of a choice than a disposition.
We all get to make that choice every single day. To me, there’s really no contest.
I choose half full.
Do you consider yourself more of a half-full or a half-empty person? Is there something coming up in your life that might benefit from a more optimistic appraisal? Share your thoughts with me, join the conversation in The Wonderground, or spend time this week recording them in your journal.
Stay young and stay fun,
P.S.
We had a fun hangout this week with the Founding Collectors of The Collector Club, who are receiving the inaugural print release as we speak. If you like my art, and enjoy receiving fun things in the mail, you should consider joining. Subscribe by August 31 to get the September print!
NEW! Summer Mini*Print Collection
Check out the new set of summer-themed Mini*Prints only available until September 1, 2026.
On a mission to help people break free from Adultitis to build better lives, businesses, and teams.
I am a professional reminder-er and permission granter who moonlights as an artist, author, professional speaker, and publisher of The Adultitis Fighter, which helps people create lives filled with adventure, meaning, and joy. I enjoy Star Wars, soft t-shirts, and brand new tubes of paint. My wife Kim and I homeschool our three weird kids and live in Wisconsin, where we eat way too many cheese curds.
View online • Get this from a friend? Subscribe here! Shenanigating Since 2000 | 2026 Issue #29 ✈️ Happy Sunday, Reader! Greetings from Sheboygan, where I can hardly believe it's August already! Yesterday, August 8th, was Escape Adulthood Day. You won't find it on any calendar, unless it's a Celebrate Everything calendar (the 2027 edition is coming soon!) We invented it because the idea that you can't make up your own holidays is a rule that doesn't exist. It coincides with the launch of our...
View online • Get this from a friend? Subscribe here! Shenanigating Since 2000 | 2026 Issue #28 🍩 Happy Sunday, Reader! Greetings from Sheboygan, where I am ecstatic and humbled to be welcoming well over ONE HUNDRED Founding Collectors to The Collector Club!🎉 Thank you to everyone who jumped in on this new adventure. The fun is just beginning! But fun was nowhere to be found when Kim and I were trying to get home from Fort Worth recently. Every single airplane was grounded by the storms...
View online • Get this from a friend? Subscribe here! Shenanigating Since 2000 | 2026 Issue #27 🏆 Happy Sunday, Reader! Greetings from Sheboygan, where we're down to the final days to join The Collector Club as a Founding Collector and receive the inaugural print! I'm not sure which is the bigger sell - fun mail every month or new artwork every month. Put them together & I'm sold. :) —Mary Beth Updike Twenty-five years ago, before kids, when Kim and I were living on Hamburger Helper and...