2 Million Miles Later: Was It Worth It?
On a recent flight to Los Angeles, United handed me my 2 Million Miler recognition.
And to celebrate? A handwritten note from the pilot, a free snack box, and a free drink. The plaque and pen arrived in the mail later.
I laughed out loud.
Not because it was not kind. It was. But because in that moment, with a snack box in hand and a lifetime of boarding passes in my bones, the question surfaced instantly.
Was it all worth it?
I started flying United in 1995. Die-hard brand loyalty. Nearly three decades later, I have racked up enough miles to circle the globe many times over, and enough memories to fill more than one life.
The Real Perks Were Real
There were genuine rewards along the way. Business class upstairs on a 747. Lounges that felt like small oases between meetings. Extra bags, extra grace, fewer lines. A rhythm to the road that eventually became its own kind of comfort.
And the world itself was a gift. I played golf at the pyramids. Went on safari in Kenya. Sat in the homes of the people I was coaching in order to understand their cultures and challenges in ways no briefing document could capture.
How do you measure that?
But Miles Do Not Only Measure Distance
They measure absence.
A first home run I missed.
The day braces came off and a kid could not stop smiling.
The quiet, ordinary nights that become precious later.
I held one boundary without exception: I never traveled on Kourtney's birthday or the boys' birthdays. Not once. But life does not schedule its hardest moments around birthdays.
It seemed like every time I was out of town, that was when something happened. Cars breaking down. Emergency room visits. Milestones and meltdowns and moments I wish I could have been present for. Through nearly five of those years while we were living overseas, Kourtney held down the fort. There were 13 more after we returned to the USA. I am deeply grateful for her steadiness, and I also mourn what I missed.
The road gave me new friends, people I was able to help, and a front-row seat to a big, complicated world. It also cost me things I cannot get back.
I Do Not Have to Force a Verdict
Some days I feel grateful. Some days I feel regret. And the older I get, the more I realize I do not have to choose one or the other.
Two things can be true at once. I can mourn the time I missed with my wife and kids, and be genuinely thankful for the adventures that shaped me. Both are real. Both deserve to be held.
So was it worth it?
I honestly do not know.
But I know this: whatever value came from those miles is not going to end with me. I want to share the stories, the lessons, and yes, the upgrades with my family. Including the Boy Scouts on our trip to Northern Tier, where each scout got to fly first class on one leg of the journey. That memory alone was worth a few thousand miles.
Because the real reward is not 2 million miles.
It is who you become along the way. And who still wants to be close to you when you finally come home.
What This Has to Do with Leadership
Every leader who has built something significant has a version of this question. You gave a lot to get here. Was it worth it?
We have found that the most grounded leaders are not the ones who force a confident answer. They are the ones who can hold the tension honestly, who can name what they gained and what they lost without needing one to cancel out the other.
That kind of integration is not weakness. It is wisdom. And it is the foundation of the kind of leadership that lasts.
A Moment for Your Own Reflection
If you are a leader who has been on the road, literally or figuratively, sit with these questions:
What have you gained from the sacrifices your ambition required? What did those same sacrifices cost you?
Are you holding both sides of that ledger honestly, or are you only counting one?
Who still wants to be close to you, and are you making room for them now?
The real reward is not the milestone. It is who you become along the way.
And who still wants to be close to you when you finally come home.
If you are navigating the tension between ambition and presence, we would love to think through it with you.
