If you're going to work your ass off, you should at least enjoy yourself.
I believe the answer to purpose, freedom and motivation is to do work that feels like play.
And if you don’t believe that’s possible, you’re not thinking creatively enough.
ABOUT JON
The Proper Bio
Jon Tan is a life and business coach for Asians who followed the plan and wound up with a life that looks good on paper but feels off. He helps them figure out what's wrong and build a life that actually excites them.
His clients include corporate hotshots in the top 0.1% of their industry, heirs to family empires, the former head of private banking at one of Southeast Asia's largest banks, and a globally acclaimed, award-winning clown.
He gets it because he's lived it: a very Asian upbringing crossed with a very un-Asian path. He went from Singapore's top 1% academic stream to skipping university and formal employment altogether. He's been running creative businesses since he was thirteen, with a highlight reel that includes directing campaigns for global brands like Raffles Hotels, short films that bagged awards at festivals worldwide, and playing a dad in a national McDonald's commercial with a fake wife, a fake son, and real burgers.
He was born and raised in Singapore and now lives in Bangkok. He is the author of I Should Be Happy but I Feel Like Shit.
MY MISSION
My mission is to reduce the amount of regret in the world.
I think what I’ll regret the most on my deathbed is not having done what only I could have done. To have wasted my talents, my gifts, my privilege on work that didn’t better the world in any meaningful way.
And few things hurt more than watching brilliant, hardworking people with big dreams, stuck in lives that offer nothing more than a good salary. It’s regrettable.
My theory is that capable people tell themselves “I can’t” because they’ve never met anyone who makes it feel possible. There’s no shortage of success stories, but it’s hard to relate to someone who’s already made it to the top of their mountain. We look at them and think “that’s not me”.
That’s why I believe what the world needs is more people living their dreams. When you do that, you become living proof for the people around you. The way a kid looks at a successful parent, relative or neighbour and thinks that’s possible for me. You become a catalyst for the people around you.
That’s why I think the way to reduce regret is to be living proof for the dreamers around me, and to create more living proof in the world by helping others live their dreams. May we ripple outwards and change the world.
MY ORIGIN STORY
I became a coach by accident
What I didn't realise was I've been coaching for most of my life. I’ve run a very wide range of businesses throughout my life, but the same thing always happened. Clients would hire my company for creative work, but I’d inevitably wind up being their go-to confidante and informal advisor for their personal lives. My mentors and peers would tell me this was ridiculous behaviour that had to stop.
I’d nod and then do nothing about it, because it was in hindsight always my favourite part of the job, and I could justify it as good customer service. Still, I never wanted to become a coach. I’d always believed in the power of coaching and I’ve had coaches of my own. But I was sure that I was too unserious for the job. Coaches were poised, proper and intellectual. I, on the other hand, am frequently described as a cartoon character.
Then, while on a sabbatical (I was burned out after seven years of running a prior business), I trained under my favourite of all the coaches I'd worked with. The plan was to learn to coach myself and save a couple thousand dollars a year. As part of my certification, I had to coach three people. I put up an Instagram post with a booking link and went to sleep.
I woke up booked out for a month and a half.
It was an unexpected mix of people. An ex-client's wife who'd witnessed how I’d helped her husband get through a rough patch. Acquaintances I had spoken to once who said that single conversation had changed their lives. Friends of friends who were told they absolutely had to speak to me.
But that wasn’t my “oh my god this is it” moment. My initial reaction was damn it I’m supposed to be on sabbatical!
That omg moment arrived when I realised these sessions were fundamentally no different from what I'd been doing all my life. The work felt like effortless play, but lives were being changed. Where I’d always needed discipline to get started with work, when it came to this I needed discipline to stop. And I knew, in a way I couldn’t argue myself out of, that I could be one of the best in the world at this.
Without a plan, I shut down my business and went all in.
Often, what we do best comes so easily to us that we struggle to think of it as special. A fish isn’t surprised it can breathe underwater, it’s surprised you can’t. I was fortunate enough to have a moment where I could see my gifts early enough in life to build something with them. Most people aren’t that lucky. My work boils down to creating that moment for others.
THE FUN STUFF
Things that are true about me
WORK WITH ME
If I sound like your kind of person, you’re probably mine too.
Come and tell me what you’d actually do with your life if nobody was watching.