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The Bucket Interview

Raging Against the Clock

Scott O'Leary, Founder of

By David Abend

Scott and I worked together at an ad agency in Boston in the early 1990s. He recently started a blog called, a project “dedicated to telling the stories of inspiring people over age 50 who rage against the clock and openly rebel at the norms of age.”

TB: What prompted you to start OVER50badasses?

SO: Millions of related and unrelated paths led me here. It’s truly the result of a complex  three-year journey both physically and spiritually. Failures and successes were equal partners in its making. This just felt like the right thing to do. It felt like a focused  expression of spirituality, creativity, optimism, inspiration and purpose. A celebration of a life lived and being lived.

TB: You say that your mission is to “tell the stories of inspiring people over age 50 who rage against the clock and openly rebel at the norms of age. Be heard.” Why do you think these stories need to be told?

SO: I’m going to use you as an example. I go to Boston for a race. You are kind enough to make time in your life to share lunch with me. Before your clam chowder has arrived, we are talking about how you nearly died and how that has changed the course of your life. Your story shifts my world, my perspective. Changes me. That’s why. We, you, me, are all amazing beings. And we know so little about one another or ourselves. This is just a vehicle to tell a story like that table at The Barking Crab was for me to hear yours. I guess I fundamentally believe stories like this need to be heard. I only want to put good out in the world. This feels like good.

TB: What kind of feedback have you been getting about OVER50badasses (O50B)?

SO: I’ve been gifted with three kinds of feedback. From the amazing humans who shared their stories. I have been given thanks and gratitude. From people who have been kind enough to read the stories they seem very appreciative and inspired by the level of vulnerability and honesty that is being expressed. I’m also receiving unsolicited ideas about this mission. Ideas about how I could expand it, which I find inspiring because it’s engaging people I respect. A few people have contacted me who aren’t 50 yet, but hoped they can make the club when they do. That felt like a good thing.

TB: “Turning 50 was my declaration of independence.” “Fear is the enemy.” “The clock is ticking and man, I want to get a lot of things done.” There are a lot of great quotes that show up on O50B that share a lot of the same perspective of The Bucket — helping people live more fulfilling lives by acknowledging their own mortality. Do you think most people have this perspective already and just need a nudge? Or do you think they need more of a wake-up call?

SO: The teachers I have learned from believe we are born with infinite knowledge and perspective. So yes, I believe we deeply understand our mortality. I believe as we grow and are students of a modern society we get further away from that universal knowledge and perspective. We fall asleep to consumerism, fame, ego, money, technology until something drastic happens. Death, near death or the threat of death and our real selves get shaken awake. I just think it’s worth putting another message out there as a reminder. Waking up, truly waking up is such an individual decision. It’s going to happen. For most it happens on their death bed.

TB: Did something drastic happen to you?

SO: The answer is no and yes.

No, I have not stared directly into the mirror of death, near death, or the threat of death.

Yes in this sense. I was fortunate enough to find a path. A spiritual one. The path of Buddhism, Taoism and stoicism. These paths made me very aware of impermanence. This could be my last day and being grateful for every minute. This was a drastic shift in perspective for me personally. With that perspective every encounter is drastic.

I will again use our encounter as a simple example. When we had lunch that day in Boston. You told me of your experience. What you had gone through. My old reaction would have been more like this: “Wow. I feel sorry for you. I’m glad that didn’t happen to me. I can’t think about this.”

David Abend and Scott O’Leary at the Barking Crab

What I actually felt that day: “He’s so incredibly fortunate. He’s here and I’m so grateful for that fact and his life will never be the same, it will be better. I admire him. This could happen to me and most likely something will. I’m so glad he told me this because it only strengthens and inspires me.”

Drastic is everywhere. You just have to be open to it. You can be awake and experience it as much as you want or you can close your eyes and only see what you want to see.

TB: Has this perspective — the one you now have about life, and impermanence — changed the way you approach your art direction?

SO: That is a very strange and wonderful question. It has not changed how I art direct but it has heavy influenced how I think. Create.

I like to make things that have a positive ripple in the world. That is challenging in the advertising ecosystem but I have been lucky to have been given projects that have allowed for that to happen.

The universe gives back what you try and give.

TB:  It is easy to see how this perspective has influenced your life philosophically. Has it also influenced your life practically?  Like in buying a car? Deciding where you live? Where you go on vacation?

SO: Very interesting question. Yes, it has. You named the biggest one. Vacation. At the beginning of every new year the first thing I do is plan my vacations. This is priority one. I get a whiteboard and I write down my plan. Vacation time falls into two buckets if you don’t mind me using that word. Bucket 1: Connection. We rent a beach house on the east coast very near to where Pam my wife and I grew up. My mom and dad stay with us the entire time. I have 2 weeks where I truly connect with my parents. I hate math but I have done it. They are 73. If they live until they are 90 and nothing happens to me I will only see them 13 more times. I will only see my mom and dad 13 more times in this lifetime. Death is informing life. Those 2 weeks at home with them are not up for debate. My vacation is about seeing them and being with them. No regrets.

Bucket 2: Living hard. Racing, traveling and growing. I plan out my race schedule. Ultra-marathons and Spartan races. I pick the races and places that I think will make me a better human and athlete and I use my vacation time to do just that. This has been an amazing and beautiful use of my vacation time. I’ve met amazing people, and see some beautiful places and have been pushed physically and spiritually. My vacation time has purpose. I don’t take a vacation to escape my life, I take a vacation to engage in it.

TB: That is a great way to look at things. That concept of the preciousness of time is articulated so well in the article “The Tail End” by Tim Urban of Wait But Why which we both had found on our own. I think that does a great job of putting your time left on the planet in perspective.

SO: Tim Urban’s math shows you the solution. The problem is me. I like that kind of math. So I’m 53. If I live until 90 and don’t move back to the east coast I will see the Atlantic Ocean a minimum of 37 times. That is just pure facts. So, I am clear on two things. If I want to raise that number, get home more often, move back or when I am there be aware and grateful for every minute I can be in that water or looking at it. That is how I think. That is how I live.

Again, I use our lunch in Boston. That could be the last time I ever see you face to face in this lifetime. You made time for me, I made time for you. I knew when we were sitting there that could be our last personal encounter unless we both know this math and we do something about it. I cherished that time at the Barking Crab. Even knowing the math, I had a friend and we had a bit of a parting of the ways. Very unfortunate. I thought a lot about what to do. I thought if I died or he died would I be okay with it. I was for a long time. I kept putting it through the lens of death and as time went I felt less and less sure. I was talking to a mutual friend about reaching out to him. About a week later he had a massive heart attack. The widow maker. He miraculously lived. I reached out to him almost immediately after I found out. Our friendship has never been better. I will say this about Tim Urban’s math. If you accept it and use it, it is very humbling. Like tragic events. Like death. Being humble and humbled is the gateway for gratitude. Tim’s math is humbling and makes you feel gratitude — or possibly denial. “I don’t want to hear this. I don’t want to talk about death it bums me out.” It’s hard on the ego just like death is hard on the ego. The math is simple. Accepting it hard.

TB: The “lens of death”. I love that. In creating The Bucket, I have gotten a lot of advice from people with whom I shared the concept. Often people tell me that they love the idea. They just have one suggestion: Don’t talk about death. It’s just too depressing. For me, death/mortality has to be the leverage point for The Bucket.

SO: I don’t know how you can have a conversation about life and living without including impermanence. We are all going to die. Everything dies in the universe. It’s the way this works. Someone gets told they have 6 months to live. What do they do? They drop all these societal chains and they run out and do all the things they wanted to do. Why not just accept that reality as it is and get to work living? If the idea of your death depresses you then I would question how you are living.

TB: I think it is fair to say that you feed off your own impermanence. You use it to motivate yourself. And keep things in perspective. Has this perspective also motivated you to deal with the practical side of that? Do you have a will? Do you have a plan for income in retirement? Have you decided where you want to be buried? Or, if cremated, where you want your ashes to end up?

SO: I do not have a will. Not because the subject is depressing or oppressive. I keep saying I have to get to it and I don’t. In the same way I really should paint that room. I guess it should be more important than that but it never rises higher. I should reflect more deeply on that. Thank you.

I do have a financial advisor. I started somewhat late compared to my peers.

He’s a great guy. He understands my goals and he doesn’t pressure me to do things I don’t feel comfortable doing and I don’t pressure him at all. It’s been a rewarding relationship beyond the accumulation of money.

I think about the final act quite a bit actually. I do want to be cremated. But I love the idea that has been floating around in cyber space about being planted with a tree and what is left here because food and part of a trees life. (read our Capsula Mundi interview) I love trees. If I were cremated, I’d love my ashes to end up in the Atlantic Ocean. On the beach and in the water. That feels like home.


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Jeremy Hager
Jeremy Hager
4 years ago

Wow! Thanks for sharing this. Lots of great ideas here, and it left me with things to think about.