Time to Turn Things Upside Down? 🙃


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Happy Sunday, Reader!

Greetings from Sheboygan, where we are thrilled with the early response for the 2027 Celebrate Everything Calendar. BIG thanks to everyone who has supported us with their order! Today is a great day to secure yours, as the price goes up $1 tomorrow, and each day until we close reservations on October 31.

This week, I've got a new installment of Echo Base Dispatch, the video series from my studio. You can watch it here, or keep reading. :)

When I'm working on a portrait, I always do something my wife thinks is weird.

After I block in the major shapes and outlines, I turn my reference photos and artwork upside down.

Then I keep drawing.

The reason I do this is that during the course of a portrait, my brain tries to be helpful and goes into autopilot mode. Because I've seen millions of faces over the course of my life, it steps in, overrides my eyes, and has me draw the nose the way it thinks it's "supposed" to look.

The problem is that when it comes to capturing a likeness in a portrait, a generic nose won't do. Everybody's different. I can't rely on generalizations; I need to see what's real, and draw that.

If my portrait is not successfully capturing the likeness of the person I'm drawing, it means that somewhere along the way, I started drawing my assumptions, not reality.

Turning everything upside down takes my brain off autopilot.

I no longer see this as a face, but areas of shape and form. To nail the likeness, I need to focus on values and lines, not noses and eyes. I need to rely on reality, not assumptions. This simple trick almost immediately allows me to see where I went wrong so I can make any necessary adjustments.

Here's the cool thing.

You can use this same strategy to improve your life, relationships, or business.

Our assumptions come from our brain working on autopilot. We just need a way to turn things upside down so we can see what's really real.

Spend the day doing the work of a frontline employee.

Watch someone else use your product without your instructions.

Experience your clinic as if you were a new patient.

Sit in your student's desk and imagine a day through their eyes.

Or maybe swap chores with your spouse for a week.

The point is to let go of your assumptions and experience things as they really are. As Isaac Asimov said, “Your assumptions are your windows on the world. Scrub them off every once in a while, or the light won’t come in.”

Sometimes we don’t need new ideas, but a new perspective.

If something you care about isn’t quite turning out the way you’d like (such as your business, a relationship, or a project at work), let go of your assumptions.

Turn off autopilot by turning things upside down.


What in your life could benefit from a new perspective? Share your thoughts with me, join the conversation in The Wonderground, or spend time recording them in your journal this week.

Stay young and stay fun,

P.S.

Don't forget that if you order 5 or more calendars, you save $5 per calendar. Perfect for holiday gifts as well as team and client appreciation gifts!

2027 Celebrate Everything Calendar

Filled with Jason's whimsical art, the stories behind them, and 365 real holidays to celebrate in 2027! Don't dilly dally; this year, we're only taking orders through October 31, 2026.

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Jason | Escape Adulthood

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.

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