The Five Best Moments of Your Life

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

« Previous Post
Next Post »


If you liked this post you can receive future updates to the Ignited Leadership blog by email.

11 COMMENTS ON THIS POST To “The Five Best Moments of Your Life”

  1. Isaiah Collier October 7, 2014 at 4:15 pm

    You know Jason I use to live my life around making money, then I remember something my mother said to me “you can’t take it to heaven with you”. That statement really resonated with me and made me look at my life from a different perspective. I know now the true treasure in life is happiness and surrounding yourself with an abundance of love. A lot of people never get to this point or when they do it seems to be to little to late. So in the words of Olivia Pope, I am a Gladiator and I choose to Stand in the Light. I interpret that to mean, I choose to be the best me ever and never give up.

  2. Jason October 7, 2014 at 5:31 pm

    Isaiah – so good! You’re right, in my experience as well the trick is to find happiness (often a side effect of finding the courage to be true to myself) and love (often a side effect, for me, of vulnerability) and that has shaped my life much more positively than money and success. It is a shame people don’t realize it sooner, but I’m glad to know you’re out there fighting the good fight as well. And I’ve never heard that Pope quote before, but it’s great. Thank you.

  3. Tori October 7, 2014 at 6:09 pm

    Jason, great read! First, I recently discovered Settlers of Catan and I LOVE IT! Also, I think societal values play such a large part of this meaningful moments vs. success thing. I would like to think that most money driven people started from more humble beginnings. They started to live a dream, fulfill their purpose, or provide for those they spend those meaningful moments with, but while they were in it, society told them to push harder, be stronger, get richer and they listened. I feel that way sometimes in higher education and the push for a PhD. The farther we get from our core and support system, the more closely we listen to society.

    • Jason October 7, 2014 at 6:22 pm

      Hey Tori, thanks so much. And Next time our paths cross, I’m totally taking you on in Settlers! You make a good point, a huge part of the disconnect comes from societal influence (vs being in touch with yourself). I love your phrasing “The farther we get from our core and support system, the more closely we listen to society”. Really insightful stuff!

  4. Becky October 7, 2014 at 7:11 pm

    I totally love this blog! You are spot-on! And I hope that you NEVER scale back on your writing!

    • Jason October 7, 2014 at 8:20 pm

      Thanks so much Becky. I’m working to slowly scale up my writing and am super appreciative of the encouragement.

  5. Andrea October 7, 2014 at 7:23 pm

    This post made me think a lot – thanks :). One thing that I realized a few years ago just before having my second child is that I didn’t want to regret not spending enough quality time with them. And by quality I mean being in the moment as much as I can and focusing only on THEM, not my dirty floors and my sink full of dirty dishes, or how to perfect my power-point presentation for my class the next day. It also means that I’ve found so many ways to have fun with them without going too far from home or spending a lot of money. I’m far from consistent but I’m working on it and I’ve had many amazing moments with them. The result if that I’m happy a lot and proud of the values I’m teaching them.

    Another thing that this post made me think of was the time we drove to Montreal together from Maine. I barely knew you and was frankly a little worried about your driving skills, but to my surprise, I had a blast and it’s a time I’ll never forget.

    • Jason October 7, 2014 at 8:24 pm

      Hahahaha, I’m awesome at driving. And that was fun.

      And thanks for the kind words. Obviously, I don’t have experience as a parent, but it sounds to me like you’re doing it right. A decade ago or so parents were lining up to buy their kids Tickle Me Elmo toys for Christmas. I always thought that was the stupidest thing ever because I’m pretty sure what a child would love more than an electronic stuffed animal is for their parents to play with – and tickle – them.

      To be fair to you, I think very few people are truly consistently present in anything these days. I bet you’re crushing it. 🙂

  6. Tyler Scherer October 7, 2014 at 8:34 pm

    This article was perfect for me right now.At 24 there is so much pressure to find your career and become successful. The world puts so much pressure on being “successful” and possessing material goods. However, that comes at a cost of time with family and friends. My last 5 most important moments have been when I spent time catching up with family or hanging out with friends. Your writing helped me realize I need to find that equal balance. Money can only get you so far, but family lasts a lifetime.

    • Jason October 7, 2014 at 8:47 pm

      Thanks Tyler, you made my day. When I was 24 I felt the weight of the world on my shoulders. I thought that unless I got my professional life exactly right, I would basically mess up my entire future. Looking back (and looking forward) I realize that there is no truth at all to that. In our 20’s we’re still coming right out of the gate. We have 50ish years of work ahead of us to be “successful”. I think you’re smart to put your relationships up front. It’s what I’ve been working to do for the past year or so.

Leave a Reply