The Five Best Moments of Your Life
Last winter: It’s nearly 2:00am. I’m sitting across the table from an extremely successful investor at a 24/7 dinner. I order a decaf. He orders a house salad and a milkshake. I can’t figure out if this is the smartest thing I’ve ever seen, or the most pointless. I still don’t know.
This guy is made of money. Before he was an investor, he was an executive at a Fortune 500 company. If he stopped working today, several generations of his family would still be able to live in luxury. Easily.
But he doesn’t stop working. Instead, he presses forth. He tells me that he aims to make his current startup (in addition to being an investor, he’s building a tech-business) a $100,000,000 endeavor.
That’s hard. Almost no one does that. Maybe he can. I don’t know. But I’m not even sure it matters. His business won’t particularly improve the quality of life for other people, and he doesn’t need the money.
No matter how hard I try to put myself in his shoes, I can’t seem to understand why he spends his time this way.
He’s in the process of moving to a new city. He tells me that the other night he was packing boxes and looking at old photos of his children.
Reflecting on the photos, he says, “You know, I missed a lot of cool moments in my children’s lives while I was busy building companies.” He goes on to describe his relationship with his wife as, “Two ships passing in the night.”
It’s funny, because when we were having this conversation, I had just hit a milestone in my business and life that would prompt me to change almost everything.
At that point, Ignited Leadership had become unequivocally “successful”: I was taking first class flights, I had a waiting list of clients, I spoke before audiences of 1,000+ people. I had become the entrepreneur that most entrepreneurs think they want to be.
But I realized something: when I looked back across the arc of my life, none of the best moments were the big glitzy ones. In fact, a lot of the time I spent building Ignited Leadership distracted me from the things I loved the most.
The best moments for me, so far, have often been the quieter moments of human connection:
- A late night conversation with my brother at the beach in Maine
- Lying in bed on Saturday morning reading and drinking coffee with my girlfriend
- Playing Cranium on Christmas with my family
- The time Stephen did the big fart while we were all hanging out, or when Will pegged Larson with the angry bird
- Sitting in a cafe and watching the leaves fall off the trees
- Spitting marshmallows at deLone while Pete watches on both proud and amused (summer camp is a magical place…)
- Playing Settlers of Catan while Conor babbles on about the non-existent “Three Sheep Shepherd” rule
That’s where life lives, those little moments. And it was right around then when I decided to scale the speaking back a bit and invest more in my relationships and my day-to-day.
So I ask the investor, “Is it worth it to you to sacrifice huge parts of your family and personal life to endlessly build businesses?”
He pauses, and thinks about it, and says, “Yeah, yeah it is. By building businesses, I create jobs and improve the economy. That’s the greater good.”
But I don’t buy it. He doesn’t seem happy. I’ve known him for a while, and he seems stuck on an endless treadmill waiting for someone to say, “Hey, you’re a good guy. I would still love you even if you weren’t successful. You should love yourself too.” Or actually, it seems like he’s stuck waiting to say that – and believe it – to himself.
And I think he’s got it exactly wrong. One of the biggest problems with the world today is that we’ve been sold on the idea that there are things more important than ourselves and our relationships.
So we neglect our people and ourselves and pursue money. Status. A bigger apartment. A more relaxing vacation. Whatever.
But really, most of us would be happy with eight hours of sleep a night and some good time each day with people we love who love us too.
I don’t mean to say that there is anything wrong with ambition. I’m ambitious as hell. It’s just that ambition and success should be secondary to yourself and your people. But it’s hard to keep that in focus when life revolves around material goods and hard work.
What I suggest you do: ask yourself, “What were the five best moments of my life?”
Sit down and make a list of the times when the world made you sit up and think, “Whoa, life is pretty amazing right now.” You’ll start to notice patterns. For me, virtually all of my best moments include people I love with ample space for us to be together.
Once you see the commonalities in the best moments of your life, shape your life to create more of those moments. Move to be closer to your friends. Quit your job. Reduce the unnecessary. Start travelling. Do what you have to do, because even though life can feel really long at times, it’s way too short to dwindle away being a slave to an artificial master.
After you’ve built a life that’s close to who you are, then all that stuff we normally talk about – leadership, success, building better communities – will be far, far easier. We often think success precedes happiness. Not true. Happiness makes success achievable.
Of course, you can pursue success without building a great life for yourself; that’s totally your prerogative, and it’s exactly what the investor has done. A lot of people do that. But I just can’t help but wonder: what’s the point?
Photo credit: Snow + Friends by Darren Webb