You Won’t Find The Best Opportunities on a Linear Path

My unemployed younger brother reminds me of a multi-billionaire.

One night, my parents called me ready to plan an intervention. My brother, who recently graduated from college, is living at home with them. He wakes up every day around noon. His days are filled with two primary activities: videogames and outdoor sports. He has no motivation to apply for jobs. And, my parents are going crazy.

My sister and I were a lot more ‘pro-active’ and ‘responsible’ in that sense. We were box-checkers. We did everything we were supposed to do.

So, on a typical day, I would have jumped on my parent’s bandwagon, hoping to shake some sense into him. But not that day. That day I realized that maybe I was wrong. Maybe my brother was right. Maybe this traditional path to success that most of us are on doesn’t lead us to success at all.


That morning I had watched Larry Ellison’s commencement speech at the University of Southern California. And I realized that most of us are looking for the wrong thing.

Coming in fifth on Forbes’ 400 list in 2020, Larry’s net worth is estimated to be $80 billion. He is a renowned tech-investor, co-founder, executive chairman, and CTO of Oracle.

And his trajectory was far from traditional.

Much to his family’s disappointment, Larry dropped out of med-school and moved to Berkeley, California, searching for adventure. He fell in love with the Sierra Mountains and bought a sailboat on which he would sail in the Pacific.

He didn’t need much. He was blissfully living pack-check to pay-check, working as a river-guide in the mountains. He just wanted enough to live a peaceful and active existence, immersed in nature. He wanted to experiment. He spent his 20s trying different things; racing bikes, sailing, constantly changing jobs.

He was still in his 20s when his wife divorced him for his lack of ambition.

And he was still in his 20s when he began to work for his first Silicon Valley start-up.

Unlike most people, he wasn’t chasing career advancement. He wasn’t chasing higher status or better pay. Just like my brother, those things weren’t important to him. He was looking for joy. He just wanted to have a good day every day.

And since conventional opportunities weren’t feeding this desire, he created his own.

“I liked my work most of the time, but I didn’t love it. I searched and I searched, but I just couldn’t find a software engineering job that I loved as much as I loved sailing. So I tried to create one. I put together a plan to start my own company. That way, I could completely control my work environment. I would hire the most talented programmers I knew, and we would all work together on the most challenging and interesting software projects. My goal was to create the perfect job for me. A job I truly loved. I never expected the company to grow beyond 50 people”. — Larry Ellison

Today, Oracle employs over 130,000 people worldwide.


Most of us have walked a pretty linear path in life. I don’t mean we’ve all walked the same one. But if you were raised in a traditional education system or were involved in any extra-curricular activities, sports, music lesson, you name it; there was always an obvious progression.

If you’re in first grade, the next obvious step is second grade. If you excelled in your current job role, the next obvious step is a promotion (to whatever role comes next).

When you’ve been with a partner for a few years, you might be asked: when are you getting married? Or, are you thinking of having kids? It’s the next ‘obvious ‘progression.

We view life as though it’s a linear path that we need to keep walking on, or we’ll get left behind.

You don’t want to be the only friend that’s not promoted. Or the only friend that hasn’t bought a house before you’re 30. Or the single friend with no kids.

All we see are milestones along the linear path of life.

But life isn’t linear.

It’s not about reaching certain pre-determined milestones.

In reality, there are no pre-determined milestones. There can’t be because there isn’t yet a future.

Your ‘path’ only goes as far as where you’re standing right now. You’ve walked your past, and you’re standing in your present.

But your future is yet to be defined, and anything can happen. You don’t have full control. But you can choose to walk with intention. You can define the milestones that you want to welcome onto the path that you create for yourself.


So I told my parents not to worry. Their son might just become a multi-billionaire. It’s too soon to tell; he needs to move to Berkley, get married, and divorced first. But maybe his mind-set is all set. Maybe he just realized this sooner than I had.

He spent fourteen years in school, then another four at University studying chemical engineering. He checked the boxes he was expected to check. But when will it stop? He’s decided — now.

He looks for joy in his day today. He wants to go rock-climbing, ride his bike, go for a hike, laugh with his friends. He has savings for now. So why does he need to apply today?

He’s thinking about what he wants to do. He’s meeting new people that could teach him about new opportunities. He’s reading to learn more about what’s out there, beyond what he’s been fed at university.

All this time, I thought I was ‘headed in the right direction,’ doing all the things I was told I was supposed to do. But was it what I wanted to do?

I wanted to become someone that others considered to be ‘important,’ a ‘reputed professional’ that was ‘socially accepted.’

And there it is — I was depending on other people’s approval for success. I hadn’t defined what success was for me; I followed what I thought was a pre-defined path towards success.

This meant that my commitment to keep going was driven by fear as opposed to a purpose. The fear of falling behind kept me going, as opposed to the desire to achieve something. I thought, so long as hit the milestones that I’m expected to, I’ll fit within society’s definition of ‘success.’


The truth is there is no single path to success. Your definition of success is different to everyone else’s. And it’s the only one that matters.

You don’t need to depend on other people as much as you think you do. You don’t need a piano teacher to learn to play the piano. You don’t need a publicist to write and publish a book. You don’t need to apply to a ‘fast-track’ graduate job to become a manager. And you don’t need anyone else to consider you successful. This all depends on you.

Don’t keep jumping through hoops if they’re not the right hoops.

The other day, my cousin came for dinner and explained that she had been offered a promotion. A promotion she had worked hard to get. But when she got it, she realized — maybe she didn’t even want it. She’s a young mother of two, and this job requires frequent travel, less time with her family, more responsibility, and added stress. Sure, to everyone else, she had just become a little bit more successful. But had she? Had she become more successful by her definition of success? She didn’t feel it.

As Niklas Göke once wrote“we think of opportunity cost as the missed reward for choosing only one of two options, but, actually, it’s the combined reward of all alternatives that’s missing — even the ones we haven’t created yet.”

If my brother had applied to a graduate role straight out of university, my parents, like most people, would probably consider him ‘successful.’ But my brother is right. Why would he take that opportunity when it only presents an opportunity cost?

If he doesn’t know what he wants to do, surely his time is better invested in trying to figure that out. He’s not socially secluded, doing nothing all day. He’s active, he’s happy, he’s social. He’s doing what he loves. People may think he’s crazy. But maybe that’s a good thing. Because –

“When you start telling people that all the experts are wrong, at first, they call you arrogant, and then they call you crazy. So remember this…when people start telling you that you’re crazy, you might just be onto the most important innovation in your life”. — Larry Ellison

Define your own success. Detach it from the status quo. What do you want to achieve? Once you know this, you can start shaping your path in the direction you want. You can seize the right opportunities for you and create your own along the way.

The only person who needs to think it’s a good opportunity is you.

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