Surpassing Expectations

Navigate expectations like Odysseus.

O. Crowe

Apr 11, 2025

Transcript

I’ve recently realized how greatly, to an extreme, I internalized a phrase from my youth. It goes:

“Surpass expectations. It’s the only way you’ll make a difference in this world.”

For me, this phrase has generally proven convicting, yet powerful.

Focusing on surpassing expectations—whether yours or others—can amplify your abilities and contribute to making micro-decisions that can incrementally accumulate over time into powerhouses of momentum.

When I first took on this adage, I was right around 15 or 16 years old, so when a teacher offered this reflection, I perked up and listened.

I thought I’d found a secret of the universe.

If I created projects and homework assignments that made 100%, that meant I’d “objectively” surpassed expectations, and that I was well on my way toward making some form of mark.

The principle got me to and through a cool college, yet life in the real world after graduation ushered in patterns of dysfunction.

From housework to personal appearance to professional writing to personal writing, there were suddenly too many areas of life to be able to apply the principle to all of them, or any of them. Ever since, it’s been a conscious daily struggle to decrease the arenas of dysfunction.

Then along comes a week like the one that just passed.

I’d made sacrifices to write, record, cut, and EQ a podcast episode so that it would be ready to release Wednesday.

I listened to it one last time, ready to deploy . . . and just couldn’t.

In my revisions, I’d ended up cutting out “the point” of the episode.

I’d been “killing my darlings” as they say to do in creative writring classes, but taken it so far that it wholly missed the underlying purpose altogether.

I was therefore at a crossroads.

Upload an episode that I know, in my gut, to fall short of my expectations, and those of listeners? Or withhold the episode, and restart the next week?

I decided to withhold the episode, because surpassing expectations isn’t actually the only way to make a difference in this world.

Establishing the right expectations, at the right place, for the right reasons, at the right time, does make a difference for yourself, here, now; and yes, can have ripple effects that can continue outward, affecting whomever comes close.

In this particular context—that of a podcaster who needed to choose between “consistently” releasing on time or consistently speaking words that I, at least, feel to be reasonably purposeful at the time that I release them, I chose the second option . . . . even for a podcast presumably on finishing what your start.

Here is what I learned.

One. Offer yourself anchors.

Whether you are new to a discipline or an old pro, it’s easy to become unmoored as a raft at sea, with emotions as the winds and unrealistic expectations as the waves.

Different projects and pursuits require different types of anchors. Is the type of anchor that applies to your situation an outline? A blueprint? A to do list? A series of sticky notes on a mirror?

Whatever the trick is for you, check in on your anchor periodically throughout the project. Don’t wait for the end.

Two. Recognize when you’re on the wrong shore, and respond accordingly.

The ancient Greek hero Odysseus landed on a number of wrong shores before reaching the right one. Dallying always came with brutal penalties.

In your case, if your gut says that you must redirect your energy, don’t postpone the redirection. The sooner you confront your error, the sooner you can continue to grow.

Three. Go for the strawberry milkshake.

When a friendly waiter sees you scribbling your next script late at a Denny’s and suggests a strawberry milkshake to wash down your coffee, roll with it. A life striving for discipline and continuous creation should still permit room for serendipity and delight.

Four. Set a schedule

As the same strawberry milkshake waiter advised, set a schedule. You should do this, because:

Five. Expectations and schedules are what you make of them.

A three hour mainframe can make all the difference. Yet so can a mainframe of thirty minutes. Or three.

You are the one who is proceeding on your journey, after all.

The expectations you are striving to surpass may feel like a cyclops trying to eat you, or an enemy trying to entrap you, or an ally trying to help you, or friends strapping you to a mast to keep you from steering your ship toward sharp rocks at a siren’s call like an idiot, because you were too proud to cover your ears beforehand (another Odysseus reference, there, btw).

Expectations can help you or they can harm you.

Yet with the right schedule, honorable effort, and attitude that keeps your eyes on what’s possible, you might just find that victory tastes like coffee washed down by a strawberry milkshake—unexpected, but balanced.

It will all work out, the bitter and the sweet.

And tomorrow, you’ll finish what you start just a little more easily.