Pilgrims

This week in the U.S., we celebrate Thanksgiving, a holiday built on a story most of us only know by the highlights. We are taught the Pilgrims fled England for America because of religious persecution. That is true, but not the complete picture.

I recently came across a thread on X about the Pilgrims that made me realize how much we oversimplify journeys. Before the Mayflower, the Pilgrims spent ten quiet years in the Netherlands, an entire chapter that rarely makes it into the story.

Our histories are like that. They are retold through peaks and valleys, leaving out the slow and unremarkable stretches that shape us just as much.

Business stories follow the same pattern. We remember Apple starting in a garage and Jobs returning later to revive the company. What we forget is the long, uncertain middle filled with wandering, mistakes, and doubt.

This week, I spoke with two companies I advise. One is emerging from the typical messy middle. The other reflected on a forty-year origin story. Their paths are very different, filled with different wins and setbacks. Both wished they had made fewer mistakes or moved faster.

But that is the part we tend to leave out. The struggle, the stalls, the chapters we would erase if we could.

I think that is a mistake. Those forgotten stretches are not detours. They are the journey. And this week, more than any other, they deserve our gratitude.

If we want to feel genuine gratitude, we cannot limit it to the highlights. We have to embrace the full story, including the chapters that felt slow, confusing, or unfinished.

Why do I believe this is so important?

The parts we tend to skip over are often the ones that change us the most. They build our resilience, refine our judgment, and prepare us for opportunities we likely could not have handled earlier.

The following are five reasons to be grateful for your journey, whether it’s business or personal:

Sliding Doors

In the 1998 film Sliding Doors, Gwyneth Paltrow plays Helen, whose life splits into two parallel timelines based on a single moment: catching or missing a subway train. In one timeline, she uncovers her boyfriend’s infidelity and begins rebuilding her life. In the other, she stays with him, unaware and held back. The film captures how tiny, seemingly insignificant moments can completely redirect the course of a life.

We all have decisions we wish we could redo. But even if we had the power to change them, we have no idea what new path those decisions would create.

Maybe things would have turned out better. Maybe you would have reached your goals sooner. Or maybe the alternate version of your life would be far worse. There is no way to know.

The point is that life is not a fixed track. It is an unfolding timeline with countless possible outcomes at every moment. Whatever your journey has been, there are infinitely more versions that you would never trade for the one you know.

You can’t cherry pick a moment and pretend the rest of the timeline stays the same.

Hidden Gems

My twenty-two-year-old son recently took a CPR course. Afterwards he said, “They taught us the same techniques you used on me when I was choking.”

My first career was in medical research. Working in the lab required CPR certification. Over the years, I occasionally wondered how my life might have been different if I hadn’t “wasted” those early years as a lab rat.

The truth is, I have many reasons to be grateful for my science background. But none comes close to this: when my ten-year-old son was choking, I knew exactly what to do. That CPR training, which I likely would not have had otherwise, helped save his life.

Take a moment to reflect on your own path. What hidden gems are buried in jobs, skills, or seasons that once felt boring, random, or like detours?

Contrasts

The next time you’re scrolling social media, notice how often before-and-after videos capture your attention. Transformation is powerful because contrast is powerful. The “after” only hits because you’ve seen the “before.”

Our lives work the same way. The wins feel bigger because of the setbacks that came first. The breakthroughs feel sweeter because of the plateaus that nearly broke us. The seasons of progress are meaningful precisely because we remember the stretches where nothing seemed to move.

If every moment were exciting, none of them would be. Without the boredom, the struggle, the repetition, or the waiting, the high points would lose their shape.

Contrast gives your journey depth. It gives your victories context. It gives your growth a storyline.

This is why the mundane parts of your path matter. They are the backdrop that makes the brightest moments shine.

Exclusivity

No matter what your journey has been or how it has unfolded, it is uniquely yours.

No one else has lived your exact combination of choices, setbacks, chances, values, and timing. In a world that increasingly pushes people toward the same goals, the same opinions, and the same paths, your story is one of the last things that cannot be replicated.

Your struggles give you insights no one else will ever have. Your detours have shaped instincts and perspectives that no shortcut could produce. Even the parts you wish you could erase contributed to a worldview that is impossible to copy.

That uniqueness has incredible value. It sets you apart. It becomes your advantage. And it is something worth being grateful for, especially in a time when creativity and judgement are being outsourced to A.I. algorithms.

Unknowns

Between my early career in medical research and my leap into building companies, I spent nearly two decades managing money. Growing up in West Virginia, Wall Street felt as far away to me as Mars.

Even though I worked in the sciences, I was obsessed with financial markets. I read the Wall Street Journal before heading into the lab and spent my free time with investment books instead of science texts. That interest had to start somewhere, and surprisingly, it started in Hollywood.

When I was thirteen, I watched Trading Places, the 1983 comedy with Eddie Murphy and Dan Aykroyd. In the film, two wealthy brothers switch the lives of a privileged commodities executive and a street hustler. Eventually, the two team up and take the brothers down by outsmarting them in the commodities market.

What hooked me was the final scene. They shorted frozen concentrated orange juice futures. In other words, they sold them without ever owning them. At thirteen, that idea blew my mind. I didn’t fully understand it until business school a decade later, but the seed was planted.

And that seed shaped nearly twenty years of my career. I could never have planned it. I certainly couldn’t have predicted it. Yet it became a defining part of my journey.

That’s the power of the unknown. The moments you never see coming often end up shaping the path more than anything you planned.

The Next Step

As you move through this week, take a moment to reflect on your own journey with gratitude.

Not just the high points, but the slow chapters, the missteps, the detours, the surprises, and the moments you never would have scripted.

All of it counts. It’s the raw material of who you’ve become.

Your journey is richer and fuller than it appears from the highlight reel.

So as you give thanks, give thanks for the whole story.

My goal with The Leap is to provide you each Saturday with the knowledge, tools and lessons learned to help you get started and keep going toward building your future. 

Whether you are making the leap to startups, solo-entrepreneurship, freelancing, side hustles or other creative ventures, the tools and strategies to succeed in each are similar.