How to Blast the Mediocrity Mindset with Sebastian Terry

August 31, 2021
James Whittaker

Check out this episode on the Win the Day Podcast

“Being realistic is the most common path to mediocrity."

Will Smith

Our guest today used tragedy to adopt a mindset that has become a powerful catalyst for change around the world. 

In his mid-20s, Seb was travelling overseas when he received a call that changed his life forever. One of his best friends had passed away at the age of 24. That tragic moment made Seb ask himself a simple question, “Am I happy?”

The answer was a resounding “No.” 

Immediately after, Seb wrote out a list of 100 things he wanted to do, which he hoped would transform his life – and it’s done exactly that.

Now, more than a decade later, Seb has been diligently hunting the goals on his list and, through his 100 Things community, is empowering others to do the same. He’s married a stranger in Las Vegas (Item #2), delivered a baby (#23), and even walked across a country (#36). 

With his inspiring message spreading like wildfire, Seb has become an in-demand keynote speaker where he helps individuals, associations, and companies tap into connection, grow meaningfully, and make a difference.

His 100 Things keynote has been delivered on all seven continents to over 250,000 people, and he’s raised more than half a million dollars for various charities.

Seb is also author of ‘100 Things: What's on Your List?’, host of the 100 Things podcast, a TEDx speaker, and featured in ESPN documentary ‘100 Things to Do Before You Die’.


Check out the YouTube or podcast version where Sebastian Terry does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


In this episode, we’re going to go through some of Seb’s craziest experiences, including being shot in the chest in Colombia and booking a one-way flight from Australia to Oklahoma to visit a stranger on death row.

Seb will also share:

  • His moment of reflection after tragedy
  • Why people wait so long to seek what makes them truly happy
  • How to create YOUR list of 100 Things, and
  • What you can do to blast the mediocrity mindset once and for all. 

Before we get started, remember that the right bit of inspiration can completely change the trajectory of someone’s life, so if there’s a friend or loved one who needs to hear this episode, share it with them right now. 

Let’s WIN THE DAY with Sebastian Terry!


James Whittaker:
Seb, great to see you! Thanks for coming on the Win the Day show.

Sebastian Terry:
Mate, that was great. What an intro! Wow.

Just getting you pumped up!

Thanks so much.

Where do we even begin with you!? Where I would like to begin with your amazing story is that moment in high school when you were sitting down with a career advisor who had basically suggested to you that going to university would be a great path for you. How did you feel at that time and how comfortable were you with that path?

Mr. Tebble was his name, a really lovely guy. But yeah, I think he just said the same thing to everyone. "What do I do?" "Go to university." At that age, I just had no idea. I was 17 or 18 years old, and I kind of just went with it. I didn't question it.

I was quite sheltered growing up, and I didn't really think outside the lines. So I went to university, but didn't learn a lot. I got this kind of odd degree called 'human movement,' which they then changed to 'exercise science' because they realized it sounds a lot better than human movement. 

But yeah, it was kind of this dull sort of path that I walked for three and a half years. I actually remember coming back from England where I had been backpacking, and getting the degree. I came back for graduation and I thought, "Oh, this'll make my dad really proud." And my dad, at graduation, just looked at me and was like, "Cool, well done." And I was like, "Oh. Well if it meant nothing to him, why did I do it!?" So yeah, I had one of those moments.

What's the problem with people who go straight to university and attach their happiness to a piece of paper that they're going to get at the end of it?

Well, I don't know if it's a problem that everyone suffers from. I mean, for some people perhaps it's good. Some people are lucky enough to know exactly what it is they want to do out of high school, I imagine. I don't know too many, but in that case, fantastic. I can only speak for myself, but I do think it ranges far wider than just me.

How are you meant to know? How are you meant to know at that age what you want to do? And I think committing a lot of money to a degree that's quite niche might work out. I mean, I have friends who did my degree, and they ended up as teachers. Actually, one of my friends here in LA, he's the head trainer for the LA Galaxy soccer team.

So it works out for some. But I think the majority of people, and, again, myself, I ended up $19,000 in debt three and a half years later at my graduation, with this bit of paper. I remember thinking, "What on Earth does this even mean?" I actually applied to be an engineer, because my dad was an engineer. That's how little I knew about myself. I'm not an engineer. I have many other skills, but I don't have those ones!

I ended up $19,000 in debt three and a half years later at my graduation, with this bit of paper. I remember thinking, "What on Earth does this even mean?"

At the end of the day, nothing matters, so you hope that everyone rolls out in this space where they are really comfortable, and they find themselves, and their purpose, and all those wonderful words. But it's not guaranteed.

So perhaps the journey is, you just get rough and ready, and who cares if you do a degree or not? But I came out feeling a little bit underwhelmed, and I thought, "Well, that's given me no clarity on anything." So I kind of went on a bit of a journey to try and figure out why I felt like that.

I was always envious of those people who knew exactly what they wanted to be when they were young, "Oh, I'm going to be a doctor, I'm going to be a lawyer, an accountant," whatever it might be, and had a very linear path ahead for them. But for people who don't have that linear path — such as the ones who have entrepreneurial tendencies — it can make that frustration and discomfort so much more significant.

Yeah, I think so. I mean, I don't know if I'm an entrepreneur. People keep saying that more and more, but I don't know. I'm creative! Maybe entrepreneurs are creative. I don't know.

But you know what I mean? There's stuff out there that I'm trying to explore all the time, even now. I just turned 40 last month, and I've been trying to do a handstand, which is really hard! I guess when you do a degree, you just get put down this path, which is just sort of very within these lines, and that wasn't what I needed. So I opened it up a little bit.

What I love about your journey is that you have been so open to the universe, different possibilities, and different pathways. After university, you found yourself drifting aimlessly overseas for a few years. How was your mindset at that time when you were doing the drifting? I'm sure you were having a lot of fun along the way, but were you full of enjoyment and happiness in the present, or was there always an uncomfortable feeling deep down that you had a responsibility that would eventually require your fill attention?

Well, I knew I was drifting, I knew that. Yeah, I finished, went backpacking for about a year and a half, as a lot of Australians do. I went to South America, America, into Europe, a little bit of Africa. I was kind of in the moment just enjoying myself, and I was figuring out a lot about myself too. You just have little conversations or events that happen, you're like, "Oh, I didn't know that about me," or whatever.

But I remember I was actually on a bus in Morocco, and we were driving through the Atlas Mountains. I remember looking out the window about 18 months into backpacking as a 23 year old, and just thinking, "Oh, I need to get home. I'm done with this."

So I ended up going home, getting a myriad of random jobs. I was teaching surfing, I was working in bars, I was working at radio stations as the guy on the street giving away free donuts. I was just doing anything and everything. And I knew I wasn't doing what I perhaps was called to, but I was having fun at least.

Back then, I also thought that you either work for somebody or you start a business. And so I ended up starting an inflatable movie screen business, as an event company, with a friend of mine in Australia, just because I thought that's kind of what you do. Two and a half years into that, I was really miserable. I didn't care if we made a billion dollars, which we absolutely didn't, or nothing. I was just unhappy, and again, that was part of the catalyst of me starting this list of 100 things.

You were backpacking overseas when you received that tragic phone call about what happened to Chris. Can you take us into the moment when you heard about it, and how it impacted your mindset at the time?

Yeah, so I was in Canada staying with some friends, Roddy and Janita, and the phone rings the middle of the night, and it's a friend of mine from the Northern Beaches in Sydney. Borfo is his nickname. And Borfo tells me, "Yeah, Chris has passed away." And I don't remember much of the phone call after that, in honesty. The news completely shook me, and it did for so many people in the Northern Beaches. I remember getting out a pencil and a piece of paper, just jotting down stuff. When I'm processing stuff, I like to write, it helps me.

I remember thinking, "Well, what's really important?" I have this degree, I'm backpacking, I'm in Canada in the middle of nowhere, what's actually important? And to me, I believed Chris was happy. If he got his life again, would he do the same things, or would he change it all?

My conclusion was I don't think he would change anything. I think he lived a really good life. It was values-driven. He lived on the Northern Beaches, he loved his mates, he loved his family, he loved team sport. He loved having fun, he loved having a beer. Rightly, wrongly, by anyone else's code, he just lived his authentic kind of life through his values. It was a life far too short, but one really well-lived.

In Canada, in the middle of the night, I thought about that question for myself, "Well, if I died today, what could I say about what I've done up to this point?" And I thought about it, for the very first time, because it's important to take a step away to get a different perspective on things, of course, and I just hadn't done it before with me.

I thought, "If I had my life again, I would completely change it."

I realized, "Oh my God, I would change everything." I spent three and a half years doing a degree that meant nothing to me, I was backpacking, which seemed great, but again, I was just doing it because other people said, "You should go backpacking," so I did. I just didn't know who I was, and I was unhappy. I didn't know anything about myself. I thought, "If I had my life again, I would completely change it."

I began writing down just a few things I would do that would make me smile more. It just dawned on me that my priority is to be happy. So on the list went marrying a stranger in Las Vegas. Why not!? I was always curious about it. Another one was to live on a deserted island, and so on, so forth.

It was just so profound to me. I was like, "What could be more important than being happy?" Nothing. To this day, that's all I want.

There's an Earl Nightingale quote that says, "Most people tiptoe through life waiting to make it safely to death." Obviously there's a place for safety, but if you're living that authentic life it inspires other people around you to do the same.

And there's a passage that stood out to me in your book that said, "Death sparks reflection, first of the deceased, and then of yourself." That really stood out to me. What was your process of self-reflection in the days immediately after receiving that news?

So interesting. I thought about Chris and his life — what would he do it differently? I don't think he would've done anything differently. I thought about my life — would I do it differently? 100%, was my realization. So I created the beginnings of what was 100 Things, my list.

Chris's funeral was like four or five days later. I was in Canada, but the funeral was in Sydney. And I was so inspired by this thought of, "Oh my God, I just need to do things that make me smile," whatever that is for me. Then I looked at my list, the beginnings of it, and thought, "I'm going to go to Las Vegas and marry a stranger" since I was in that part of the world anyway. So I flew to Vegas, and I did that.

Now, I did that as opposed to going to Chris's funeral, which sounds weird, and it was an interesting decision. Because obviously there's the respect part of going to a funeral and paying your respects, but I thought, what better way to kind of honor Chris than by doing something which he directly inspired me to do? So I did that.

By coincidence, the day I got married to this stranger was actually the day of his funeral. And then I flew home a few days after, and I saw his family and our friends straightaway.

But yeah, that was it, the direct result of that was two or three days later, I married a complete stranger. It was such a great story. Her name was Shivali. I actually had her on my podcast recently, and I hadn't spoken to her in 11 years.

You're a horrible husband, aren't you!

Well, it didn't work out, it lasted a day! But yeah.

Out of everything that you included on your original 100 Things list, like skydiving naked, setting a Guinness World Record, and getting married to a stranger in Las Vegas, what was the one that scared you the most to even contemplate it or put it on the list?

Well, they're all pretty scary. The theme of my list is hopefully they make me smile more, or learn something about myself or the world, I guess. But the majority of them were also out of my comfort zone. What's the point otherwise? In this evolution of growth, you need to get out of your comfort zone. I think you feel your edges, and suddenly you realize, "Oh, I'm a bit more capable than I thought I was."

They all kind of scared me. I mean, posing nude in art class, obviously. It was very confronting. Living by myself on a deserted island for a week was really confronting. Doing an ironman, like a long-form triathlon, that was scary. They're all scary in different ways. I mean, some are physical, some are emotional.

In this evolution of growth, you need to get out of your comfort zone.

Learning French is scary in one. Even now, I'm still learning, it's ongoing. And I had a virtual Zoom date with a French girl, actually French Canadian, about a month or two ago. I was just sweating. My French isn't that good, it's definitely not good enough for a conversation. So that was awful. I told her I had a red car halfway through the date, and the date finished shortly after!

Twelve years into this journey, the death-defying and adrenaline-pumping stuff isn't really me anymore. My values have changed over time. There's far more important things now than risking breaking my neck.

In your book, you mentioned that you grabbed a piece of paper, and you wrote, "Death puts things into perspective. We only have one life." And you've touched on perspective a couple of times so far today. How can people receive a similar jolt you did without having to wait until it's too late, or going through the tragedy that you went through?

It's such a great question. The common narrative is that we all know someone who has almost lost their life, lost someone close to them, has been diagnosed with any number of terminal illnesses like cancer. And it's those people, only after a dark moment, who go, "Hang on, what do I want to do?" They then look at the light, the opportunity. "What's happiness to me?"

Why do we wait to do what makes us happy? It's an interesting question. The answer, of course, is we don't have to.

So I'm really fortunate. I speak to lots of people who do incredible things, as you do, and as many people I'm sure who have been in this seat on your Win the Day podcast have done as well. As often as I can, I try to ask, "What allowed you to do that? Why you?" And none of these people ever really say, "Because I'm special," or, "I'm brave," or, "I'm lucky."

Well, some of them do. But the majority say something to the effect of, "I just gave myself permission." A split second decision to think about themselves, then they choose to move forward. So my answer to your question is, how do people take a moment to change their lives or consider what else could be different? Choice. And that's it. Just choose to. It's as simple as that.

But the majority say something to the effect of, "I just gave myself permission."

I think we try and overcomplicate it. Especially in this world that I've accidentally found myself in, which is like personal development or something, which is so funny to think. But we overcomplicate it.

We do this accountability group every Friday, with people from all over the world. And they come in and we say, "Share a goal, and how you're going to do that." And so they share a goal, and then they say, "I don't know how I'm going to do that," so we talk through an action plan. We say, "Just do it. We'll catch up next week to see what happened." Everybody starts doing these things.

So every week now, we’re flooded with people who say, "You won't believe what I achieved this week!" No matter how big, or small, or complex, or simple. For me, it's just giving yourself permission to choose or consider what you want to do. That's it.

And the work that you're doing, it gives people that external accountability too, right?

Yeah, they say that by writing down a goal, you're 42% more likely to achieve it. If you share that goal with someone, you're 65% more likely to achieve it, and if you share that with somebody ongoing — like an accountability buddy — you're 95% more likely to achieve it. Which is remarkable. So having accountability in some shape or form when it comes to your goals is crucial.

How do you believe people would change their lives if they knew when their time on the earth would end?

So interesting. On my list was to see a fortune teller, but it was the most underwhelming goal for my list. I asked her, "Do you know when people are going to die?" She points and me and goes, "91 years old."

I was like, "I didn't ask you!"

The acknowledgement that we are going to die does add a healthy urgency to living.

I don't like using the term bucket list, even though we get what that means, and that is essentially what I do. Because it puts all the emphasis on death, things to do before you die, and it's very fear-driven, "You're going to die, so make sure you..." So I tend to stray away from that. Having said that, the acknowledgement that we are going to die does add a healthy urgency to living.

I'd like to think that the majority of people would cut away the fat (i.e. the things that are a bit more useless), and focus more on what's important, which I think we are unfortunately losing a lot of right now with social media.

Often, you talk about the importance of putting on your own oxygen mask first. Why do so many people find it easier to concentrate on someone else's life than their own?

Well, I think, yeah, so I think the theory is, if you put your own oxygen mask on, you're okay, and then you're okay to help other people. That's been my journey since I've started the list. But a lot of people are either one or the other —they're either incredibly selfish, or incredibly selfless. But either of those aren't good; it's the combination which is healthy.

To your question of people helping other people more so than themselves and why, I think it's easier because it takes the pressure off you. You can also tell yourself subconsciously, well, "Oh, I can't do the thing, because I'm just being such a good person elsewhere."

I get a lot of emails from mums who look after their kids and do all the things, which is absolutely gorgeous and needed. But they do forget about themselves, and a common email I get is, "My son / daughter has just left the house, they're 18, and I don't know who I am."

I think that highlights the problem of imbalance. You need to look after yourself a little, and others a little, and put them together, otherwise you end up a little bit devoid of something that's really important.

If you were sitting down with someone to help them make their 100 Things list, what would you say are the most important attributes of what makes a good list?

Well, as we teach it, there's eight steps: four to create your list, and four to activate it.

Step one is permission. Just giving yourself permission to think about yourself. It's not selfish, it is not negative, it's really selfless, ultimately, because it makes you a better person for other people.

Step two is to reflect on your life. You can't change what's happened beforehand, but you can certainly live full now. We actually get people to write a eulogy and highlight things about themselves. And if you understand that stuff, which can be quite confronting, you can go, "Oh, right. I need to change X, Y, and Z."

Step three, then, as we teach it, would be your spokes to your wheel of life, kind of like a value thing. If you imagine a wheel with spokes, and that's your life, what are your spokes that make your life stronger? It could be anything, but typically it's family, connection, adventure, education, and maybe spirituality. There's a million things. But if you're able to identify those spokes to your wheel of life, let's just say health is on everyone's list, I think, you can then go, "Right, what's five health-related goals?" And that's how you start a list.

And that's step four: creating a list, going from those four previous things. Permission, reflection, spokes, list.

The idea of traditional goal-setting would be that you have something specific and measurable that you write down, but in my experience people will say, "Yeah, I want to have a million dollars in the bank," but they don't put a timeframe around it, they don't talk about the how, and they certainly don't make it emotionally-charged (i.e. why do I want to achieve that goal).

How does the 100 Things list intertwine with traditional goal-setting?

You're right, I think a lot of people put things on list because, "A million dollars would be good." In fact, I just interviewed people in Venice Beach, California. I walked around the boardwalk, and I said, "What's on your list?" And so many people said, "Money. A million dollars." And it's like, okay, cool. What then? And if you keep asking, "Why, why, why," it gets to, "I just want to be happy," right? That's ultimately what we all want. So that's why the reflection part is really important. You only want things on your list that are meaningful to you, otherwise what's the point? So you have to think about yourself as an individual.

So the Will Smith quote you started with, "Being realistic is the most common part of mediocrity," it's so interesting, right? Traditionally, the R in the SMART goal-setting acronym is being realistic. Will Smith, the guru, says, "Well, actually, that's just going to lead you to mediocrity." I agree. I think once you have your goal, let's assume you've done a course and it's very meaningful to you, because you've understood that your mum has an illness that you want to get a million dollars to help with that illness, that's meaningful. It's then about, again, simplicity.

So once you've got this list, these goals that are meaningful to you, it doesn't have to be overly complicated. At that point, there was just three things that we would teach, understanding the who: Who were the people involved? Is it just yourself? If you're running a marathon, do you need a trainer, do you need to then speak to the events coordinator to buy a ticket? Do you need to speak to your partner to say, "Hey, I'm not going to be around for the next six months much, because I'm training." Whatever it is.

Just to reiterate this, I don't think goals need to be realistic.

Then you the go to the what: what are the specific things that happen? I mean, quite literally, that's all you need. You need a pair of running shoes, you need to train, you need to buy a ticket, you need to turn up to somewhere on a certain date, or whatever.

Finally, the when: what's the timeframe? Can you start right now? The answer is usually yes. If it's a marathon, there's a specific date, so now suddenly you have a timeframe, and you can work on everything. I think it's just simply the who, the what, and the when.

Just to reiterate this, I don't think goals need to be realistic. Richard Branson just went to space, as did other billionaires. That seems completely unrealistic as a child, because they wanted to, and they did it. So I think you're very much limiting yourself to what you think is your capacity, which of course isn't right. We're far more capable than we think.

Where you have to be specific is in the planning. That's where, if you want to get healthy, the goal can't just be like, "Get healthy." You need the how, specifically how. And obviously action is the key.

Yeah, put that energy into the plan.

Of course. There are so many lists out there that just go unachieved because action was never applied.

How often should people revise their lists, and how often do you revise your own 100 Things list?

Well, I'm just revising it now, actually. The need to revise a list is based on the premise that we change as people over time, our values change. I'm different to how I was when I started this 12 years ago. As I said, it was about breaking the shackles, it was about liberation, and freedom, and all this stuff, and now it's not. It's more about connection and trying to serve.

In my experience, anytime you achieve something that's quite noteworthy, it's like that coming down off a high, where you might feel a fleeting moment of, "Wow, this is a pretty cool moment," but you're right back down, and in some cases you can feel pretty low afterwards. Have you had a feeling like that with any of those experiences that you've been on?

Never. And I'll tell you why — and it's because I'm special! That's the brilliance of the list. If you have a list of things where each thing is meaningful, you check one off, and then you go, "All right, what's next?" That's life. Like, just linking this all up. This bucket list, it's not something that sits aside to life, it is life. It's career, it's personal, it's professional, it's within the community, it's internal psychology, it's all of those things.

You hear of post-expedition blues, and of course I get it — you do something incredible, and then you come back and you're like, "What's next?" — well, what a great question, what's next? Think about it. Come up with a goal and go for it, and you'll be just as excited.

One of my biggest learnings from my whole journey is I that thought it would take me 100 Things to be happy, but I couldn't have been further from the truth. Although I'm somewhat celebrated for having this list of bizarre list, that's the tip of the iceberg. My list is purely a vehicle for me to get closer to understanding who I am, and it allows me to get closer to that every single day.

I dare say the secret to actual happiness is just finding out who you are and being that every single day, no matter what the situation — if you're by yourself, if you're with your partner or loved one, friend, social, if you're on a stage. If you're just yourself, that's happiness. Not whether you've jumped out of a plane naked, or climbed Everest, or done any number of other things, which are all great and needed for the process, but that's not it. Who cares if I've done 100 things!?

The secret to actual happiness is just finding out who you are and being that every single day, no matter what the situation

Like this sounds weird, but I think about like this. So I'm on stages speaking, and I always think as I look out at the crowd, "They pay you money to speak about a list of..." If an alien came down from wherever he is, and he stands at the back of the room, or floats, and he says to the person next to him, "What's he talking about? Why are all these people listening to him?" And the person goes, "Oh, he's doing the things that he wants." The alien would go, "What, are you not!? It's not everyone doing that?" It's ridiculous. So we should all just be doing the things, because ultimately it brings us slightly closer to who we are.

I think that's a great definition of happiness.

Getting shot in Colombia, tell us about that experience in particular!

I was hitchhiking across America, which was I think number 43 on my list. I went from Ft. Lauderdale to San Diego. And in every single car, pretty much every car out of the 13 rides I got over six days, everyone had a gun. And on this one occasion, this Mexican guy, he was so funny, I can't remember his name, he was so fun. He goes, "I have a gun in my glovebox if you want to play with it." And I was like, "Okay, that came out weird!"

And I did, so I got out this gun, and he's like, "It's not loaded."

I was just holding a gun, and I'd never held a gun before. I just pointed it at myself so I could look down the barrel. Then I was like, "Oh my God, oh my God," and I put the thing away. It freaked me out. So I was like, "How do I get over that? What is that?" So I said, "Well, I'm going to get shot. I'm going to get shot, I'm going to have one pointed at me and someone shoot me wearing a bulletproof vest."

So I then googled “bulletproof clothing factories” and the first one that popped up was in Colombia, this company called Miguel Caballero. They do bulletproof clothing for like the Taiwanese Army, the president of the US, suits and shirts and whatever.

I emailed them and I said, "Hey, I want to get shot, would you mind?" And he emailed me back and went, "I'd love to." So I flew to Colombia, got picked up by these guys in Bogota, taken to this factory where he makes all this stuff, and yeah, I put on like a leather jacket. It was bulletproof, of course, and he allowed me to pick a bullet.

I emailed them and I said, "Hey, I want to get shot, would you mind?" And he emailed me back and went, "I'd love to."

So I picked a bullet, and he stood at point blank. Then he asked me to count to three, and on three just exhale, and he would shoot me.

I go, "Okay."

I saw his finger on the trigger pull it quite tightly, and I just saw his knuckles go a little white. I remember in that moment, thinking, "What if this goes wrong?" Because I didn't think about this — what if I die? What if he shoots me, and I die?

This happened to me 18 months after I started this journey. I started the journey because I asked myself, "What happens if I die today?" And my answer was, "Oh, I'd be pretty unhappy, I don't even know who I am."

But on that day, 18 months into the journey, with this guy about to shoot me, I thought, "What happens if I die today?" And I realized, I'd be happy.

I realized, "If this goes wrong," it'd be pretty funny, actually, because it's completely my fault, but I'd die happy.

He said, "Count to three," and I said, "One," and he shot me.

He shot me and it worked, of course, and that was interesting that you can do that.

What a planet we live on!

Would it almost be better not knowing when the gunshot was going to go off!? Obviously I'm sure the bullet would've been quite painful too, with the force and everything, but the wait of someone to shoot you must seem like the hardest 10 seconds of your life.

Yeah. It was very strange. It was a factory, there were like 500 people working on sewing machines, putting the Kevlar or something in all these suits and shirts. And he'd shot them all! When they get the job, he's like, "Congratulations," bang."

They were all looking at me. It was just a eerie silence as it happened. He had his daughter in there who was wearing a pink tutu and roller skates. She was just skating around the whole time. Here I am getting shot, and she skates past.

Just another day in the factory!

It was so strange. After that, I flew straight to San Diego to check off something else on my list, which was be an ordained wedding minister and marry two people together. I was already a minister, and I got invited to marry some people I'd never met together. So I did that. Life's brilliant and weird.

You had a moment where you booked a one way ticket to Oklahoma in the US to visit a death row inmate named J-Loc. Was that experience about ticking something off the list? Or were you thinking it might be a more profound moment?

Well, I have to frame it. My friend passed away, and I married a stranger in Las Vegas. I went back to Australia and went, "Wow, this list is unbelievable, I'm going to do this." And then I completely conformed back to normality, and I started this business, and whatever.

Two and a half years later, I was really upset, I started crying in the back of the cab, actually, because I had no money, and a friend had paid for my dinner, and I just felt like shit. Then I was like, "Huh. I wonder what happened to that list of things." So I went home got it out of my drawer, put it on the wall, got a map, and put 100 tags all over the map. I was like, "That's it, I'm going to go back to this list. As soon as I pay the company off, I'm done."

So I looked at what I could start working on, and one was visit an inmate on death row. The reason being that I wanted to chat someone who had a completely different reality to mine. So I just googled “death row pen pals”. Google is an incredible tool.

I wrote to one guy, and for 12 months we conversed, written letters back and forth. Then he invited me in, and it's coincidentally at the same time that I paid the company off. I was like, "Right, I'm going." So I flew to LA, one way ticket, and then to McAlester, Oklahoma, to see J-Loc. Because I'm really curious about life, and I like to see the differences, and I like to feel that, and understand, and try and gain perspective.

That day was, it was immense. It was immense. It was in the middle of a boiling hot place called McAlester, this penitentiary up on the hill, glistening barbed wire as I'm driving up to it. You have to relinquish all your goods: take your belt off, your phone, your wallet, and what have you.

They let me in, and I went three levels underground. And then there's these doors, you open and you walk through, it shuts behind you, you walk through another one, and it shuts behind. Like something out of Maxwell Smart.

So he is in his cell for 23 hours a day. The one hour a day he gets out, it's in a cell which I think was three levels underground, but there's no ceilings. So it's basically a skylight right up to the sky, which you can see. And he said if he's lucky, he gets in there, and the sun will be crossing the top of it. If he's lucky, he'll be able to see the sun. I think it is a security thing, from my understanding.

So I looked at what I could start working on, and one was visit an inmate on death row.

I went into this room, go through the doors into another room, and there's three windows on either side, and in front of each window's a stall. Next to each window is a telephone on the wall. So I sit next to the second one on the right, there's reinforced glass, there's bars, there's a telephone here. I look through and it's an empty, tiny room.

Suddenly the door opens, in walks J-Loc who I've been chatting to for 12 months via letter. He comes in, puts his fist up against the window, and we do a fist bump. And I pick up the phone and we chat for five and a half hours about everything. Everything. I learned about what he did, he had never told me over letters. I told him what I was up to, he showed me all these letters from girls that he's been chatting to in there. All these photos, he's like, "This is my Sunshine, this is my Sweet Pea," he had nicknames for all of them.

J-Loc is saying, "Yeah, that dude next to me, he's getting killed tomorrow." And I was like, "Wow. Why?" And he goes, "Well, he murdered someone, he doesn't care, he's very open about it. He has no remorse."

So it was just a very real, real conversation. I love writing, so I wrote a big story about that, and put it on a blog I had. That was the story that Random House read, and they were like, "We would like you to write a book about your experiences."

What did J-Loc say about this crazy Aussie who'd flown, I guess including transit time, almost 30 hours to be at a prison to see someone who he had never met before?

I don't remember what he said about that. I think he just appreciated the contact.

Life's just amazing. Quite clearly, it's got nothing to do with seeing an inmate on death row, it's something else. It's something about connection. I remember when I left, I went out to the car, it was a boiling hot day in this tiny town of McAlester. Dead armadillo on the side of the road. I walked to the car, and I looked up to the sky. It was vast out there, because it's a tiny place. It was blue, it was hot, and I was like, "Oh my God, I'm free." I got such an appreciation for being free.

I was wearing a pair of underwear, of course, but I took everything else off, for some reason, and I just sat on the trunk of my car, and I was looking up to the sky, go, "I'm free. How special is that?" And then a police officer came up and asked me to put some clothes on. But again, it's got nothing to do with that, it's kind of like what you get from the experience.


Check out the YouTube or podcast version where Sebastian Terry does the Win the Day Rocket Round, answering questions about his favorite quote, what advice he’d give his 18-year-old self, the one thing on his bucket list, and a whole lot more🚀


How do we balance responsibility of things like diligent study that set us up for a fulfilled and meaningful life in the future, with that yearning to want to tick all of those things off the list?

They're the same thing, aren't they? You're studying because you choose to, because your goal is to, as you say, be diligent, and successful financially, or whatever it might be.

So it's getting everything in your life and putting it in alignment and creating your 100 things list based off that?

Yeah, absolutely. Again, I think some people think, "I don't have a list." If you have goals, more than one, you have a good start. Essentially, it's a list. And everything should be aligned to what you want to do, not what others think you should do, or what you think others would want of you. So I think it's the same thing. Skydiving nude is the same as doing a spiritual study, or career development. They're goals, and therefore on a list, and a list, again, should be comprised of meaningful things so that they all live together in this ecosystem.

In my experience, evaluating risk can be the very thing that keeps people stuck in the mud their entire life, and it can leave people with a lot of regrets later on. Risk management obviously has a place in the right setting, but so does action. So how do you balance that risk mitigation with taking unrelenting action the whole time?

That's a great question. Maybe that bar is set different for different people. There's an assumption as well that I'll do anything, because I'm crazy. And you say someone got shot with a bulletproof vest, you go, "Oh, they are crazy."

But you have to assess the risk, just to what degree. I see a lot of people, and I absolutely was this too, I used to do nothing. Before my list, I did nothing. I was scared, I was really fearful, the risk was too much. I didn't want to risk being embarrassed, I didn't want to risk failing, I didn't want to risk looking like an idiot, and so I never did anything.

Now I kind of blow past those, I don't really care about that sort of stuff. I think the only real risk we should consider is if it's risking your life, and then you can make a decision. And also, is it risking some sort of moral compass, or some ethical decision, or the health and wellbeing of other people.

Everyone would be impressed with themselves if they put risk to one side and just went for it.

But past that, when you get those negative thoughts out of the way, you realize, "Oh my God, I can do that. I actually can." It completely reshapes what you think you're comfortable doing, and also what you do and what you shoot for next. I really feel I could do anything on the planet. Within reason, obviously. I'm not going to be the fastest runner in the world, of course, but I can be much faster than I am now. I just need to commit to it.

I only think in this way because I've done plenty of stuff that I'm like, "Oh, I'm so impressed with myself." Everyone would be impressed with themselves if they put risk to one side and just went for it.

You're living it up now in sunny LA. What happens on those days when you wake up and you just don't feel great? How do you handle those bad days?

LA's amazing. I love it. I'm in Venice, which is a very unique spot. If you've got a structure in your life, or things that are meaningful to you, on a list, and you have some kind of action plan around them, even on those days where you feel a little under the weather or less than 100%, you have this safety net of, "Okay, cool. Should I choose to just lean into these little plans or daily things that I want to be doing?" And that can get you out of it.

But at the same time, a day of doing nothing is fantastic. I sometimes do that. If you are committed to things that are really important to you, even on those days where you feel like shit, you're still doing something that you know deep down is good for you, and that helps, I think.

What are you working on now that you're most excited about?

I'm learning French, still. Actively doing that. I can't play piano, so I want to learn a classical piano piece, because I had a friend and we went to a bar once, and it was a hotel lobby bar. There was a white grand piano in the middle, and the waitress came over, and he said to her, "Do you mind if I play the piano?"

She said, "Can you play?"

And he went, "Ah, I can."

This dude goes up, and I mean, it was incredible. He played for 30 minutes, all improvised. I later found out, he was a friend of a friend, he was some kind of piano virtuoso, and I was incredibly jealous. I was like, "I want to learn a classical song!" So I'm learning Clair de Lune at the moment, and I'm four months into learning. I'm 1:45 into the song. I love it.

So what else? The world's greatest prank is on my list, I'm working on that. I can't tell you, obviously, what it is, but if it works you'll hear about it. So there's all that sort of stuff.

Also from a business perspective, for 10 years, this has just been a beautiful, organic kind of accident. I was just living a very lovely lifestyle in Sydney, and I thought, "Well, hang on, this is great," but I started very early on getting emails from people saying, "My life's changed." I get emails from people who are on the brink of taking their life who choose not to because they started a list. We've connected strangers to help each other in acts of kindness. We found a kidney for someone who needed a kidney recently, it's unbelievable.

So I think it'd be a shame if it didn't get bigger. It'd be a shame if there wasn't more impact. How do I do that? Well, I'm not great with business, so I brought on a business person. So top of mind, and what I work on every single day, is furthering the business, growing it, developing it. James, you've been very kind, actually, and helped in various ways, which I'm so appreciative for. 

I want to impact a million people with lists, so that's kind of what I think about.

Final question: what's one thing you do to Win the Day?

I do like a little morning dance, which I like. And I surf — that makes me feel good too.

Seb, thanks so much for coming on the show!

Oh, mate, thank you so much! It was great.


If you enjoyed this episode with Seb, share your favorite takeaway on the YouTube version.

Remember, to get out there and win the day. And perhaps that begins with creating your 100 Things list!

Until next time...

Onwards and upwards always,
James Whittaker


Resources / links mentioned:

📚 ‘100 Things: What's on Your List?’ by Sebastian Terry.

⚡ 100 Things website.

✔️ Sebastian Terry on LinkedIn.

📝 100 Things on Facebook.

📷 Sebastian Terry on Instagram.

🌎 100 Things - What’s On Your List? TEDx Talk.

🚀 Win the Day group on Facebook.

🔥 Do you want to Win the Day every day? Learn more about The Day Won Mastermind, tailormade for entrepreneurs who want to 10x their income, impact, and influence.

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