Strategic Pessimism

I’m an optimist to my core. I teach positive thinking for a living. I genuinely believe things tend to work out.

And sometimes a little strategic pessimism is incredibly helpful.

Let me explain.

If you’re a people pleaser, you probably know this moment well:

You want to say no. You should say no. But your brain jumps straight to, “What if they’re upset? What if they think I’m difficult? What if I disappoint them?”

Instead of forcing yourself into fake positivity (“It’ll be fine, it’ll be fine!”), try this instead: Ask yourself: What’s the worst realistic outcome if I say no? And could I handle it?

Most of the time, the honest answers sound like this:

They might be annoyed for a bit.

They may feel disappointed.

There could be a slightly awkward moment.

And then, life goes on.

Here’s why this works so well:

When you actually look at the downside, you usually realize the fear isn’t danger, it’s your own discomfort. Emotional discomfort. Temporary discomfort. And, although it’s not fun, you can handle that.

This is strategic pessimism done right. You’re not assuming the worst will happen—you’re simply acknowledging that even if it does, you’ll be okay.

Strategic pessimism isn’t about expecting failure. It’s about reminding yourself that even if the “worst” happens, you’ll be ok.

PS Saying yes to things you don’t want to do also causes a lot of discomfort in the form of overwhelm and stress. Choose your discomfort wisely :)


PPS Are you on LinkedIn? I’ve been hanging out there a lot lately, and I’d love to connect with you. 

HOT OFF THE PRESS

“Suffering lies in the gap between our expectations and reality.”

We assume alignment.

We assume agreement.

We assume people want what we want.

And when they don’t… we call it frustration, stress, or feeling “off” — when really, it’s unmet, uncommunicated expectations quietly running the show.

Learning to notice your expectations is one of the most powerful shifts you can make for your time, your energy, and your peace. It’s the kind of insight that changes how you experience relationships, weekends, work, and even small everyday moments. Listen now and save yourself some self-inflicted suffering!

Check out episode 222 here: https://tinyurl.com/OWWPod.

“Rules aren’t the enemy. Blind obedience is.”

My guest this episode, author, speaker, and leader Lauren Wittenberg Weiner, knows that when you truly understand the rules — written and unwritten — you earn the right to question them.

Not from ego.

From clarity.

That’s where things like imposter syndrome stop being a flaw and start becoming a signal.

A signal that you’re stretching.

That you’re growing.

That you’re doing something that actually matters.

And when you pair that discomfort with rational optimism — not blind positivity, but clear-eyed courage — you stop freezing… and start choosing.

Not every rule needs to be followed.

Not every rule needs to be broken.

But some rules absolutely need to be challenged.

This episode shows you how to think differently about rules - what to question, what to keep, and how to move forward with confidence.

Listen to episode 223 here: https://tinyurl.com/OWWPod! 

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