When It Feels Impossible

Today at a Glance

• Why challenges always feel bigger than they are.
  
• A simple swipe file to remind yourself you’ve already overcome worse.
  
• A practical template you can save to your phone and use for life.

It’s been a special few weeks for our family. We just welcomed our fifth child into the world.

I took some time off—late nights, early mornings, and a lot of special moments (and coffee). I’m easing back into writing and excited to get back into the swing of things with you.

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Here’s the thing about life and business: challenges are guaranteed.

It doesn’t matter who you are, how much money you make, or how successful your company is. The longer you live, the more curveballs you face.

A failed deal.

A relationship ending.

A natural disaster.

A brutal negotiation.

In those moments, your mind reacts as if the world is collapsing. You feel trapped, hopeless, convinced this time is different—that there’s no way out.

But the truth is… you’ve been here before.

You’ve faced hard things. You’ve gotten through them. Six months later, you were not only okay—you were thriving.

The problem is, when you’re in the middle of the storm, it’s easy to forget that fact.

That’s why I built a simple tool: a Challenge Swipe File.

It’s a running log of the hardest things I’ve faced and how I got through them. Anytime life feels unbearable, I can scroll through it and remind myself:

“You’ve done this before. And you’ll do it again.”

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The Challenge Swipe File Template

Save this as a note or album in your phone. Every time you make it fully through something hard, take 3 minutes and log it. Future-you will thank you.

I’m part of a CEO group, and the #1 takeaway I’ve had from hearing other leaders’ stories is this: everyone goes through extremely challenging moments. They feel impossible in the moment, but three months later—or sometimes nine months later—they’re in a completely different place, feeling amazing.

The Swipe File is a powerful tool because it reminds you of that truth. It calms your mind in the storm. It proves you can handle far more than you realize.

Here’s how to make your own:

1. The Challenge

What happened? Keep it simple and specific.

2. How You Felt

Write down the raw emotions—panic, fear, anger, hopelessness.

3. What You Did

What actions, choices or steps did you take?

4. Six Months Later

Looking back—how did things turn out? What’s the perspective you gained?

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Personal Example Entry

1. The Challenge

Our home was evacuated during the Los Angeles wildfires on January 7th.

2. How I Felt

Overwhelmed, my wife and I moved from location to location with 4 kids (while she was pregnant), not knowing when or if we could go back. At the same time, I am still running a company.

3. What I Did

Focused on a sense of safety for the kids, with daily activities for the family. Found temporary housing for those six weeks. Worked at night when everyone was asleep.

4. Six Months Later

We moved to Westport, CT (something we’ve talked about for years). Kids are in their new school. Work is thriving. What felt unbearable in the moment turned into a major positive move for our family.