Title: “Stop ‘Shoulding’ All Over Yourself”

Good morning everybody, you’re listening to the Mindset Matters podcast, I’m your host Riley Jensen and today I want to talk about how the word “should” is dangerous, and it should be handled carefully.

Let me ask you something:

When was the last time you didn’t meet your own expectations?

Be honest… how did that feel?

If you're like most high performers I work with—athletes, entrepreneurs, parents—you felt like you were failing.

And the wild part is, you weren’t even failing… you just set yourself up with unrealistic expectations.

I work with athletes who will PR in three events, but they’ll go home upset because they “should have” done better in the 4th one.

Sound familiar?

We carry around this invisible scoreboard in our minds—built from other people’s voices, Instagram highlight reels, and our own brutal self-talk. We get stuck in the loop of:

“I should be further along.”

“I should have more wins.”

“I should be better by now.”

Let’s stop shoulding all over ourselves.

Ok let’s do a quick check in:

Grab your phone or a pen and write down one thing you’re proud of that you used to dream about but now take for granted.

Pause this for 10 seconds if you need to. Do it.

It matters.

Why?

Because when we don’t acknowledge progress, our goals become weapons instead of motivation.

There’s a quote that I think originates from Socrates, but I am not sure.

“What screws us up most is the picture we have in our head of how it’s supposed to be.”

Let that sink in.

You thought your career would look different by now.

You thought you'd be more confident, more successful, more stable.

But the gap between where you are and where you thought you'd be?

That’s not failure—that’s the space where growth happens.

You’ve heard me share this before. Roosevelt’s “Man in the Arena” speech still hits hard:

“The credit belongs to the man who is actually in the arena… who errs… who comes short again and again… who fails while daring greatly…”

Let me ask:

Are you in the arena right now?

If so, you're already winning—even if you’re bloody and bruised and still chasing the win.

It’s important to understand:

Unrealistic expectations often come with unrealistic timeframes.

You want to write the book, start the business, win the starting job… this year.

But maybe that goal needs three years. Maybe that dream is a marathon, not a sprint.

And when you don’t hit it right away, you punish yourself for no good reason.

I call it mental masochism.

We beat ourselves up because we “should be” further along—based on a clock no one else is even watching.

So here’s your challenge this week:

Catch yourself “shoulding.”

When you hear “I should be further along,” replace it with:

“I’m learning.”

“I’m progressing.”

“I’m doing the work.”

Set a realistic timeframe.

Ask yourself:

What’s the goal?

What’s truly in my control?

What’s a realistic time frame for that outcome?

Remind yourself: failure is fertilizer.

Not poison.

Your stumbles today are the soil where greatness grows.

Look—dreaming big is never the problem.

Expecting yourself to sprint a marathon with no water breaks? That’s what burns people out.

Be honest with where you are. Be flexible with how you get there. And most importantly, stop shoulding all over yourself.

Your story’s still being written—and it’s going to be a good one.