Anything Is Possible: Key Lessons From Singapore Olympic Gold Medallist Joseph Schooling’s Retirement

Joseph Schooling’s retirement press conference is a masterclass on how to live life.

Joseph Schooling olympics win

The guy who beat all odds by winning the legendary Michael Phelps to clinch gold in the men’s 100m butterfly final in a then-Olympic record time of 50.39 seconds is retiring.

Yes, Singapore’s Olympic gold medallist Joseph Schooling is packing up his swimming bag.

I just took the time to watch his 20-minute press conference and I must say Joseph’s maturity clearly comes through in how he spoke and fielded the media questions.

He covered various topics, from lessons learnt in his life to his parents’ sacrifices. If you get the time, you should watch the press conference too (there’s also a transcript at the end of this post for who prefer to read).

Here are a couple of key lessons I took away from Joseph Schooling’s sharing.

Listen to Your Inner Voice

Schooling started swimming at a very young age. He used to be excited going into the freezing pool, but he doesn’t get the same excitement anymore. He listened to his feelings and realised it’s time to move on.

The Olympic gold medallist revealed how he used feelings to guide him:

“I did not enjoy the grind anymore. And one day I went to the office with mom, started encroaching onto the work aspect of life, and I started feeling that same sense of excitement again. And you start questioning yourself, okay, is this going to last for a day or two, a week, a month? But that feeling kept going on, and it kept burning brighter and brighter. So that’s when you really know that it is time to move on.”

What Schooling shared reminded me of the Conversations With God book that my uncle recommended. In it, it also talks about using feelings as your guide:

“My [God’s] most common form of communication is through feeling. Feeling is the language of the soul. If you want to know what’s true for you about something, look to how you’re feeling about it.”

Use Past Experiences to Light Your Future Path

Sometimes in life, we may have to take a career change. I have pivoted my career a couple of times, and I’m in the midst of another pivot.

Each pivot may have felt like I was doing something entirely different, but I came to realise they are more like building a tower of Lego blocks. I can use my past career experiences to help me do my future work better. No experience is ever wasted.

Schooling is pivoting from competitive swimming to something else for his next phase. However, he’s going to use his past experience to shape his future.

“I don’t like the connotation of retirement per se. I don’t like it because it sounds like there’s nothing to look forward to next. As an athlete, we need to have missions, we need to have goals. That goes the same for everyone. I want to be the best in my field no matter what I do, and I will continue putting the same amount of effort, dedication, focus, everything I’ve learned from the pool, the people I’ve met along the way into this next phase of my career.”

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Anything Is Possible

Schooling’s David-versus-Goliath achievement is a master class in how we should live our life.

“To all the young swimmers or young athletes, or it doesn’t matter artists, whatever field that you’re in, I hope when they look back at my career, they will just think there’s one thing that nothing is impossible. There’s no reason why a person half a foot shorter than everyone else in the Olympic final or around the world should be where I am today, physiologically unlikely but yet here we are. So I hope to the young kids or even parents or whoever it is watching, everyone that you can draw some inspiration, confidence, and comfort in knowing that the impossible is actually possible.”

There Are No Losses in Life. Either You Win or You Learn

When asked by a journalist if Schooling has any regrets in his career, he said:

“So there are these questions of what if, and I guess that’s what makes life interesting. But do I feel a sense of regret? No. You win or you learn, and that’s something I learned from one of my coaches.”

He also added:

“I think with everything in life, there are lessons, right? Some people believe they’re predetermined to hit XY or Z. Life isn’t such. Life throws you curveballs, you make decisions, and you have to live with those consequences or decisions that you’ve made. But no one is perfect. So do I regret it? I regret putting my loved ones and my family through all the angst and the scrutiny of it [on taking cannabis]. I think in hindsight, the best way I can move forward is to know that there is a lesson to be learned in that. And if I’m better tomorrow than I am today, I’ll take it.”

Whatever Happens, Happens

Life is a journey. It’s like taking the front seat of an underground train and watching through the glass window as the train moves.

There are only certain things within our control (for example, boarding the train), but there are many other things not within our control (whether there will be a track fault, whether the person sitting beside you will fall asleep on your shoulders, etc).

I believe we should make decisions based on what we know and control, and leave the rest for life to happen and unfold.

When asked about what’s going to happen with Schooling’s existing sponsors, he said:

“The existing sponsor and endorsement deals, the futures are promised to no one. But for right now, this very given moment, I’m proud to say I have great sponsors that stick by me through thick and thin. Whatever happens in the future happens.”

Go with the Flow

When asked about his National Service (NS) obligations, Schooling, using the swimming parlance, eloquently put it:

“All of a sudden, one morning, after I finished more or less halfway through my BMT [Basic Military Training], I don’t know what happened, I woke up and felt like, okay, you know what, you are in this situation, like I have been countless times in a swimming sense. You just gotta roll with it. You don’t fight the tide, you swim with it. As Singaporeans, this is something that we all have to do. So you come to terms with that or you’re going to have a really hard time. I like to choose the path of least resistance.”

Many Roads Lead to Rome

I feel our system encourages people to go to good schools, get good grades, and get stable jobs (basically play safe and not take risks). Anything other than this norm is frowned upon. Let’s challenge that and do what is right for our own self and not others.

“Looking back, hindsight 20/20, I hope that this is a source of inspiration. I hope that this means that we can challenge the traditional career pathways. There is more than one way to be successful. And most importantly, we’ve got to do things that we ourselves are proud of. … So I want Singaporeans to be proud of what they’re doing and not just go into a field or career just because my mom or my dad or my friends think that this is cool.”

Unexpected Lessons Galore

I didn’t expect to take away so many notes in the short 20-minute interview. I was seriously astonished by Schooling’s maturity of thought and how he so calmly fielded questions.

Oh one last thing for the curious Singaporeans. When asked by a journalist if politics is part of the plan, he said:

“I mean, never say never, but for right now, I’m focused on the business ventures on the personal side. If I am lucky enough one day to be in that spot, then so be it. You know, you can’t put a limit on anything. But for right now, I’m very happy…”

I think Schooling will make a good politician with his kind heart, experience, and level-headedness.


Here’s the full transcript from Joseph Schooling’s retirement press conference (the transcript is reproduced in full from ChatGPT so accuracy is not guaranteed):

Thank you for coming here today, sorry we’re a little behind. First things first, I really appreciate everyone making some time on this morning to be here and cover this event. It’s quite an emotional time not only for myself but the people around my family, my loved ones, my friends, my whole team. To say this is a bittersweet moment doesn’t really do this justice. It’s been filled with a lot of ups and downs. I’m sure by now you guys have already heard I’ll be retiring from competitive swimming. But with every end of one chapter, turn the page to a completely new journey and new chapter. And although a lot has happened in the last 25, 26 years of my competitive career, I am looking forward and beyond excited to the next 25, 30, 40 years of my future career. And this is where the real work starts all over again.

I still remember when I was 4 years old, I used to be so excited hopping into an unreasonably freezing pool, seeing my brothers, my sisters, my teammates. And being an only child, that strikes a different chord for myself. So fast forward to where we are today. I woke up not feeling the same excitement to go to practice. I did not enjoy the grind anymore. And one day I went to the office with mom, started encroaching onto the work aspect of life, and I started feeling that same sense of excitement again. And you start questioning yourself, okay, is this going to last for a day or two, a week, a month? But that feeling kept going on, and it kept burning brighter and brighter. So that’s when you really know that it is time to move on. I don’t like the connotation of retirement per se. I don’t like it because it sounds like there’s nothing to look forward to next. As an athlete, we need to have missions, we need to have goals. That goes the same for everyone. I want to be the best in my field no matter what I do, and I will continue putting the same amount of effort, dedication, focus, everything I’ve learned from the pool, the people I’ve met along the way into this next phase of my career.

Today, I want to say there for everyone here, there are no questions off limits. Let’s have some fun with it. Today is a sharing session. There is a reason why we didn’t call this a press conference in the invites. Obviously, this looks like one, but we wanted the vibe and the feel to be more family-oriented. The media has played a really, really big part in my career. A lot of people speak negatively about being in the media shadow or the media lens, excuse me, but I think the other way. I think this is a great chance, a great platform to inspire others, to help the next generation get better. So this is exactly what I’m going to do. I’m going to do my best at inspiring the next generation. To all the young swimmers or young athletes, or it doesn’t matter artists, whatever field that you’re in, I hope when they look back at my career, they will just think there’s one thing that nothing is impossible. There’s no reason why a person half a foot shorter than everyone else in the Olympic final or around the world should be where I am today, physiologically unlikely but yet here we are. So I hope to the young kids or even parents or whoever it is watching, everyone that you can draw some inspiration, confidence, and comfort in knowing that the impossible is actually possible. Thank you.

Hannah from MIP, I have one question for you for now. Do you have any regrets over the course of your whole career? Do you mind sharing?

Sure, any regrets? You asked me that 5 years ago, I’d probably say yeah. After the Olympics 2016, I kind of took my foot off the gas and I was head and shoulders above everyone, got complacent. And I don’t regret that right now, but I still wonder what if we just kept going along that path? So there are these questions of what if, and I guess that’s what makes life interesting. But do I feel a sense of regret? No. You win or you learn, and that’s something I learned from one of my coaches. Sorry, just a follow-up to that, what about the last couple of years, your cannabis taking? Do you think that has affected your career?

I think with everything in life, there are lessons, right? Some people believe they’re predetermined to hit XY or Z. Life isn’t such. Life throws you curveballs, you make decisions, and you have to live with those consequences or decisions that you’ve made. But no one is perfect. So do I regret it? I regret putting my loved ones and my family through all the angst and the scrutiny of it. I think in hindsight, the best way I can move forward is to know that there is a lesson to be learned in that. And if I’m better tomorrow than I am today, I’ll take it.

Hi Glenn from Money FM. Given the massive personal and financial input that your mother and your late father had to sacrifice for you, would you like to see a different way forward for emerging athletes in Singapore? Would you like to see a different way for people to be able to study and to train overseas without having to literally use their life savings and their family savings to do that?

Absolutely, I think it’s all a numbers game, right? In Singapore, fortunately, we don’t have the numbers to be able to make mistakes. We need a better formula than everyone coming from the US NCAA. There are thousands, tens of thousands of college athletes and only 1% of those college athletes make it to the pros. And maybe 10% of those 1% start flaming out in the year after that. Differently, I would be cautious to use the word differently. And this is why, whenever we try to have systemic change and we use the word different, people that have established the system naturally feel cornered. We need to understand that we play for the same team, we fly the same flag, and things can be done better. There’s always a way to improve. If we have an existing solid base, which we do, it’s gotten better. And I can attest to this from early 2000s coming to now. SAQ, for example, better people, better support structures. We are moving in the right direction. And one of the things that I’d like to do and I will be doing moving forward is helping our sports ecosystem grow. I’ve had chats with Minister Edwin Alan Go and they’ve been very receptive. So it’s nice to see that I am transitioning into this phase where people are willing and receptive to taking our country to the next level. But different? No. Get better? Yes, absolutely.

Hi Joe, Steve from S&V. Sport is something you’ve done every single day of your life since you were what, six, seven years old. What are your emotions now as you walk away from that in this whole open space that’s the rest of your life? I mean, how do you feel? Is it fear, trepidation, excitement? I mean, just want to know what your emotions are.

Yeah, man, I’d say emotions are definitely running pretty high right now. Almost comparable to after 2016, but just in a different manner, you know? I mentioned a bit about bittersweet part, but also to go one step deeper into your question, it’s a sense of identity, right? You’re crossing over to a different sphere, a different realm. And a lot of the issues athletes face or anyone really is, hey, once I leave my job, who am I? So that’s something that I’ve had to mentally prepare over the last few years and cultivate this new identity, something that I can be proud of, something that I can go to bed at night and sleep, wake up the next morning, look forward to, and know that I’m adding value, not only to myself but most importantly to the people around me. So how do you grasp with this identity change? It’s tough, and it’s an ongoing process every single day. But I’ve learned that if you’re open, you’re honest, people can see that you’re genuine, they’re more willing to help. And I’ve had some really, really good people help me forge, cultivate, and have that confidence to build this new identity over the last few years. And that’s something also we spoke about, the sports ecosystem. An athletic career is going to end. You know, everything comes to an end one day. But how do you give these athletes, especially the pipeline, the youth athletes, that reason to and confidence to go forth and say, hey, I’ve learned a lot of cool things when I’m swimming or playing a different sport. How do I use that skill to go to the business world, where you community service inspire the people around you? So yeah, the identity change is an ongoing process every day, but we’re getting there.

Hi, Joseph R from today. Would you say national service played a factor in your decision to retire? How much of a spanner did it really throw in your plans? And second question, what’s going to happen with your existing endorsement deals and sponsors?

I’ll answer the second one first. The existing sponsor and endorsement deals, the futures are promised to no one. But for right now, this very given moment, I’m proud to say I have great sponsors that stick by me through thick and thin. Whatever happens in the future happens. I wish I could give you a better answer for that. And to answer your first question about NS, when I went in, I had a really negative mindset about being taken out after the Olympics, having to adjust to this new way of life. For the first three months, it was probably one of the hardest three months of my life. All of a sudden, one morning, after I finished more or less halfway through my BMT, I don’t know what happened, I woke up and felt like, okay, you know what, you are in this situation, like I have been countless times in a swimming sense. You just gotta roll with it. You don’t fight the tide, you swim with it. As Singaporeans, this is something that we all have to do. So you come to terms with that or you’re going to have a really hard time. I like to choose the path of least resistance. To answer your question directly about NS, there’s a spanner in my career. Looking back, I wouldn’t like to think so. No, are there better things we can do in terms of timing, going to NS, supporting athletes? From what I’ve seen inside, people are doing a pretty darn good job of supporting their men in their units. That part was a huge surprise to me, and I gained a lot of respect for the SAF, the Navy, for my fellow Navy men. I didn’t think I would be feeling that way two years ago, to be quite frank, but I am today. And I’m proud to call them my friends as well. We have to understand that the people taking care of us in NS, this is their livelihood, this is their rice bowl. And they’re our military, they need to be bound by very strict sets of rules. They need to defend us, that is their job. It’s the same thing for me in swimming. Go all out when you can. Their job is to make sure we’re safe. The fact that they are willing to put their livelihoods and their careers, it may sound a little dramatic for athletes or anyone to train, hats off to them. Like a lot of respect. Can we do things better? Yes. But no, NS did not end my career per se. I ended it on my terms.

Joseph Rishan from Money FM, good to be here with you. Firstly, I think I speak for most Singaporeans when I want to say thank you for putting us on the global map. We know how big a part your dad played in your career and everything you went on to achieve. He’s not here with us physically, but I’m sure he’s with you. What do you think he’s thinking as you make this decision? And what would you like to say to him to convince him that it’s the right one?

He’d probably be saying, “Come on, one more Olympics.” What I’d say to him is, I think there’s a point in time where it’s time to do something else. And also on the flip side, get to spend more time, play golf with you. Definitely pull that card. I think you’d see things my way.

So, during a time of competitive swimming, what do you think you meant to Singaporeans then? And going forward, what do you think you mean to Singaporeans now?

I think when I was swimming, I was so engrossed in my own career, I didn’t really know or set aside the time to think about what Singapore has thought of it. The honest answer, the real magic is what happens now. Looking back, hindsight 20/20, I hope that this is a source of inspiration. I hope that this means that we can challenge the traditional career pathways. There is more than one way to be successful. And most importantly, we’ve got to do things that we ourselves are proud of. That’s all I can ask for. Whether or not it’s donating all your time for a nonprofit organization or being a big-time CEO of a company, I used to draw a really hard line between, you know, I’d rather be a CEO than donate my time. That’s a 16, 17-year-old kid speaking because those were the traditional norms that I saw in society. But now, I really think it’s, yes, you need to earn a living to eat, right? We all gotta eat. But at the end of the day, when we start, when we pass on, it’s not going to matter. And I think my dad’s passing really opened my eyes to this as well. Mom, dad, family, they sacrificed a lot. They could have lived comfortably. They didn’t have to mortgage the house and send me to the US, but they did so anyway. And that got me thinking, wow, this is a next-level love. So I want Singaporeans to be proud of what they’re doing and not just go into a field or career just because my mom or my dad or my friends think that this is cool. You know, and this should be done. And I think we’re making good progress in that field. We can always do better, but I’m happy with the direction that we’re taking right now.

Hey, over here. Thank you for your contribution and your service and for being an all-around nice guy to us in general. Congratulations on moving on to your next phase of your career. Just want to ask, is politics in the equation at any time, any point of time in the future for you?

I mean, never say never, but for right now, I’m focused on the business ventures on the personal side. If I am lucky enough one day to be in that spot, then so be it. You know, you can’t put a limit on anything. But for right now, I’m very happy, like Royce said, playing golf, going to my VC Zoom school, and helping mom out in the office. Yeah, just it’s my turn to be a normal kid, normal guy.

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Author: Sudhan P

I simplify investing concepts to help you navigate the stock market jungle.

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