The Trap of Overthinking and How to Escape It

Portugal looks perfect in the photos. Smiles in Lisbon. A first surf lesson in Madeira. Ocean views in the Azores. Wine in the Douro Valley.

But here’s the truth: I didn’t sleep for a week. A brutal HR platform transition cost me my appetite, my peace, and, honestly, my sanity.

It wasn’t even about the software itself; it was about what it controlled. The livelihoods of my team. That weight doesn’t disappear just because I’m staring at the Atlantic with a glass of wine in hand.

Behind every sunny photo was a COO trying to keep it together while her brain replayed every scenario like a broken record.

The Trap of Endless Loops

Rumination is sneaky. For high-achievers, it can feel like diligence. If I just keep thinking about this long enough, I’ll find the answer. But in reality, it’s the same thought circling back again and again.

Ethan Kross, in Chatter, calls it “getting stuck inside your own head.” That was me in Portugal: standing in wide-open beauty but mentally trapped in HR purgatory.

When the Body Keeps the Score

You can tell yourself you’re just being thorough, but your body will call your bluff. Sleepless nights. No appetite. Stress shows up in your skin, your health, and your energy.

As Bessel van der Kolk writes in The Body Keeps the Score, unresolved stress doesn’t stay in your thoughts; it imprints itself physically. My body kept score all week, and it wasn’t pretty.

The False Picture of Freedom

Travel should feel like freedom. Instagram makes it look that way. But freedom isn’t walking European cobblestones with a mind you can’t escape.

If you’re mentally checking boxes at 3 a.m. while the rest of the city sleeps, that’s not freedom. That’s captivity.

And leaders? We’re especially prone to this. We mistake rumination for care. But as I remind myself often: “Caring doesn’t mean circling. It means having the clarity to choose, act, and then recover.”

Breaking the Cycle

So how do we step out of the loop? It’s not another checklist. It’s not another late-night mental marathon. The reset happens when we choose less control, not more.

Here’s what helps me:

• Catch It Early. Name it for what it is: a loop, not a solution. Awareness interrupts autopilot.
  
  
• Give Anxiety a Job. As Matthew Hussey says, anxiety needs something to do. Thank it, tell it you’re safe, then redirect it.
  
  
• Interrupt the Pattern. Movement, journaling, or even stepping outside breaks the cycle.
  
  
• Widen the Lens. Ask: Will this matter tomorrow? In a month? Perspective shrinks the loop.
  
  
• Choose Rest. The best leaders aren’t the ones who never sleep. They’re the ones who know rest produces better decisions than rumination ever will.
  
  

Choosing Clarity Over Chaos

As my trip wrapped up, I realized both the smiles in the photos and the exhaustion behind them mattered. Both were real.

Leadership isn’t about pretending stress doesn’t exist. It’s about knowing when to step back, stop the spiral, and reclaim the clarity your team actually needs from you.

Cheers to figuring this out one messy, real step at a time.

At StringCan, we believe leadership clarity drives business growth. If you’re ready to stop the spirals and move forward with focus, let’s partner to make it happen.

Casa Dos Barros Winery, Sabrosa, Portugal