What's Your Pivot Point?

On the Fourth of July, 2010, I stood on a friend's rooftop overlooking the city of Chicago. Behind me were two years I could hardly believe. Working for the White Sox. Traveling the country with PlayStation. The dream job had found me at 24. Now, about to turn 26, I was living what many might deem a dream life. And it was amazing. It also came with a cost. While I was on the road, my friends were building lives back home. I missed birthday parties. I missed get togethers. I missed weddings. Somewhere between cities, a quiet thought had found me: I love this season, and it is a season.

So I stood on that rooftop, looking out over the whole city, and I felt how much life I still had in front of me. I knew there was so much more ahead. And I said it out loud: "My future wife is probably down there somewhere. I just have no idea where to look."

One week later, she walked into my life. That rooftop was my first pivot point.

Then came the corporate ladder. A Fortune 500 company, a clear track, a title to chase. I thought that was my moment. I was going to climb. It took time inside those walls to see the truth: I wanted a life bigger than that ladder could reach. Another pivot point.

Then a friend pushed me toward entrepreneurship, and my then girlfriend, now wife, said go. We opened a business and put our life savings into it. A calculated risk, and still very much a risk. We built that business for twelve years. I poured my heart, soul, and blood into it. Along the way we got married. We welcomed our first two kids. I became a new version of myself more times than I can count.

Then the pandemic arrived and held up a mirror. I was missing bedtimes. I was missing mornings with my kids. The life I said I wanted and the life I was actually living had drifted apart.

Mentorship changed that. I started investing back into myself, and I grew more in that stretch than in the decade before it. My wife and I took a massive trip through China and Thailand. I went on a sailing trip I will be telling stories about for the rest of my life. And when the opportunity came to move our family, we said yes. Another pivot point. Another door. Another yes.

Here is what all of it taught me:

Life is a series of pivot points.

A pivot point is the moment one season ends and a new one becomes available. The rooftop was one. The pandemic was one. The move was one. A few of them announce themselves loudly. Most of them whisper.

Three things I believe about pivot points

1. Pivot points reward attention.

Every pivot in my story started as a feeling I could have easily ignored. The restlessness on the road. The thought on the rooftop. The ache of missed bedtimes. Awareness comes first. When you slow down enough to actually listen to your life, the pivot points get loud.

2. Doors open for the people who open them.

A friend pushed me into business ownership. My wife backed the leap. Mentors showed me what was possible when I was stuck. Every pivot in my life ran through a person and a door I chose to walk through. Surround yourself with people who push you forward, and keep your hand on the handle.

3. Plan in seasons, and keep them short.

I believe deeply in clarity. Design your ideal week. Know exactly what you are building toward, and work backwards from it. And keep the frame tight: one year or less, three years at the absolute most. Life is too full and too short for a stack of five year plans. Short seasons keep you present. Present people catch their pivot points.

I used to think my path would be a straight line. PlayStation taught me otherwise. The rooftop taught me otherwise. Twelve years of building, a pandemic, and a moving truck all taught me otherwise.

The straight line was always an illusion. The pivots were the whole story.

So here is my question for you

What's your pivot point? The one you are standing in right now, or the one that has been whispering to you for months.

Hit reply and tell me. I read every response.

More clarity, more money, more life.