Most people drift through life, allowing their lives to simply happen to them. Days turn into months, months into years, and one morning they wake up wondering how so much of life passed without them really living it.
Napoleon Hill called this “the drift” in his book “Outwitting the Devil”, the tendency to let life carry you along instead of steering your own course. And truth is: if you don’t consciously design your life, someone else will do it for you. Your schedule will be filled by other people’s priorities, your dreams will be replaced by other people’s expectations, and your potential will be buried under the weight of comfort and fear.
The Cost of Playing It Safe
I’ve seen this firsthand. When I visit home, relatives who’ve just retired tell me the same thing: “You’re right to enjoy life while you’re young. I wish I had done the same.”
My father-in-law worked hard his entire life, sacrificing so his family could have a good life. Just before retiring, he had a stroke-like episode and is now disabled. He always dreamed of going to India. He won’t be able to now.
This isn’t unique. In “The Top Five Regrets of the Dying,” Bronnie Ware shares what people say at the end of their lives:
“I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
“I wish I hadn’t worked so hard.”
“I wish I’d had the courage to express my feelings.”
“I wish I had stayed in touch with my friends.”
“I wish I had let myself be happier.”
Notice a pattern? These aren’t regrets about taking risks. They’re regrets about NOT taking them.
How We’re Conditioned to Conform
We all enter school full of innocence, dreams, and ambitions, wanting to be astronauts, artists, adventurers. But then our creativity gets tamed and controlled. We’re told to sit down, be quiet, and learn the same things as everyone else, despite being different little humans with different skills and interests. We kill our individuality and become sheep. By the time we exit the school system, our transformation is complete, we’re good cogs ready to enter the machine somewhere.
If you don’t fit the mold, you’re seen as an outlier, a disrupter, a problem.
Then comes the traditional path: get a degree, land a 9-5, fall in love, get married, buy a house, have kids, climb the career ladder to afford a bigger house and car. Rinse and repeat for 40 years until retirement, when you can finally do what you want - except by then you’re old, tired, and maybe not healthy enough to enjoy it.
The media reinforces this. The system rewards this. Society celebrates this.
But here’s the thing: most of these major life decisions aren’t really yours. They’re made for you by expectations, conditioning, and the drift of doing what everyone else does.
My Rules I Broke
I’m not special. I’m just a regular guy who decided to question the default path a few times.
At 22, during my first year of my Master’s degree, I had to do a 6-month internship. 95% of my classmates looked for something nearby in France, ideally with a company that would hire them after graduation. Safe. Predictable. Expected.
I decided to go to Australia to work in a robotics lab at the University of Sydney. I barely spoke English. I didn’t have a passport. It was terrifying. But I knew English would be key to my future, and I wanted to experience a new culture.
Best decision ever. I came back fluent, which opened doors to living in Miami and now traveling the world. I also met my wife Rosie there.
A few years later, I joined an early-stage startup in 2014. I had just bought an apartment in France and was planning a wedding. The company had raised money but was barely generating revenue. Risky as hell.
It ended up being one of the best decisions of my life. Six amazing years where I learned more than I ever could have in a traditional corporate job. I lived in Miami for 3+ years. I wouldn’t be where I am today without that experience.
Then in 2021, I left that well-paid job - which gave me freedom and security - to chase my entrepreneurial dream and embrace a nomadic lifestyle. My family wasn’t supportive. They didn’t understand.
Four years later, I have zero regrets.
What Breaking Rules Actually Means
Here’s what I’m NOT saying: quit your job tomorrow, sell everything, and become a digital nomad.
What I AM saying: stop following the script by default. Start questioning what you actually want.
Breaking rules doesn’t have to be earth-shattering. It can be:
Moving to a new city while keeping your job
Leaving law to start a food truck
Starting a side hustle or hobby you’re passionate about
Becoming a podcaster, YouTuber or TikToker
Coaching a local sports team
Selling your crafts on Etsy
Or yes, selling everything and traveling the world
The point isn’t the specific choice. The point is that it’s YOUR choice, made intentionally, not because it’s what you’re supposed to do.
What’s Really Holding You Back
In my coaching work, I see the same fears over and over:
Other people’s opinions. Especially from people you love. You don’t want to disappoint them by not meeting their expectations or by failing after taking a risk.
Self-limiting beliefs. “It’s not for me.” “I can’t do that.” “I don’t know how.” “I’m not good enough.” You build walls around yourself and see no way out.
The myth of “someday.” People push enjoyment to retirement, assuming they’ll have time and health and money then. But life doesn’t always work out that way.
Here’s the truth: pursuing what you love doesn’t have to be costly. It’s actually cheaper for me to travel the world than to live in France, with a much better quality of life. Age is just an excuse. I see plenty of people 50+ embracing alternative lifestyles and thriving.
The Real Problem
Few people actually question what they really want.
They pick a college major at 17 to satisfy their parents or teachers, not out of passion. They take a job in whatever city they land, not because it’s where they dream of living. Then the trap closes. You keep making decisions based on previous decisions you had no real control over.
Life happens TO you instead of being designed BY you, FOR you.
Start Here
You don’t need more time. You need fewer distractions. You need to stop letting life just happen and start shaping it with courage.
The first step? Start thinking for yourself about what you actually want. New thinking triggers new actions, which create a new life.
But I’ll be honest, this is hard. The drift pulls you back easily. It’s easier to follow the crowd than to forge your own path.
That’s why I created a free guide called “Break Free From Autopilot: A Guide to Living Life on Your Terms” to help you start this process.
And if you want support figuring out your path, I work with people one-on-one to help them break free from living on autopilot.
Most people don’t need permission to live differently. They need someone to remind them it’s possible. Someone to show them they’re not crazy for wanting more. Someone to help them actually DO it instead of just dreaming about it.
So here’s my question for you: What rule have you been following that doesn’t actually serve you?
Think about it. Then do something about it.
Because at the end of your life, you won’t regret the risks you took. You’ll regret the ones you didn’t.
I must confess to not ever being a person who conforms - from being the only person in our crowd that played the violin, to jumping off the corporate ladder at 23...
And whilst Davina and I have no doubts about moving to Thailand, your last sentence says it all for me.
"Because at the end of your life, you won’t regret the risks you took. You’ll regret the ones you didn’t". We can't wait..
Great post. Very inspiring!