Bay Street Bull Magazine: Luxury Business and Lifestyle


How to Find Fulfilment

Illustration by Deshi Deng

Before the first phone ring had even finished, I catapulted the headset excitedly to my ear. This is the moment that I had been anxiously waiting for.

"Hi Alan. This is Jonathan from Google calling for our first scheduled interview."

His voice rang sharp over the phone, but was still friendly. It was thoughtful, yet playful (a unique combination that I would later learn was referred to as, “Googliness”.)

I, on the other hand, was really nervous.

Ever since I was a little kid, I had dreamed about working in technology, filling out all the prerequisites required in order to achieve optimum nerd status. I went to computer camp and even wrote a 5,000 word essay during high school on how breaking up Microsoft would impact technology. Suffice to say, I dreamed of the chance to work at Google.

So, I took a deep and tense breath as Jonathan lobbied a question my way.

"What would you do if I gave you a million dollars?”


I spent the next seven years working at Google, first in Corporate Strategy at headquarters, and then running a business unit in Asia. And, for the most part, I loved it. Not because of the perks, but because I was competitive and I wanted nothing more than corporate success. There was no daytime beach volleyball for me, but rather late nights filled with coffee and spreadsheets.

I got promoted, I made more money; lather, rinse, repeat. It was my entire life. I did this because I wanted praise. I wanted people to think I was smart, and winning at work was the only way I knew how to do this. Until it wasn’t.

All of a sudden, I was 30 and found myself feeling very, very lost.

It’s not a situation that I think is uncommon for people going through that stage of their lives. Even so, it was an existential situation that proved to be agonizing. I spent a long time working at Google and in my last year there, I had this revelation with my own personal struggle. For my entire life up until that point, I had spent it optimizing for success at work, as opposed to winning at life — there is a huge difference there. I had focused on getting promoted and making more money while placing meaning and happiness on the backburner. When I came to that conclusion, I had a hole in my stomach that I didn’t know how to fill. It was something that honestly caused me an immense amount of pain. For years, I felt like I had focused my whole life on one goal only to realize that it wasn’t my goal at all, or at least shouldn’t be my goal moving forward. I struggled with that for a while. It was months and months of trying to understand what I wanted to do. For the first time in my life, the excitement of another promotion or more money was non-existent. What was the end goal? I had achieved the goal of corporate success that I originally set out for myself, but it had left me feeling incredibly unsatisfied. I found myself feeling empty and in need of change, despite having the dream job that I had always wanted.

At the time, I was lucky to have gone on this project that Google has where they send people off to a far flung office that is completely unrelated to your job. So naturally, I went to Ghana for a month to work on a project. While I was there, I had this great moment of crystallization where I knew there were things out there that were going to make me more happy. But, I needed to put in the work to find out what those were. I didn’t want to leap into the void, but something had to change and I knew I had to leave Google. So, I created my own project called Time On (because I thought it was weird when people quit their jobs or went on vacation that they called it “time off”.) I spent a couple months trying to understand what was important to me and would be fulfilling beyond money. I put together a big spreadsheet where I documented everything I did every day. I wrote down how much money I spent, who I met and more; it was basically a tally of my happiness, meaning and fulfillment in order to help me optimize winning at life, as opposed to work. I had to constantly remind myself to optimize for life, not for work. Work is not my entire life. I realized that if my goal was to be a 10/10 at work, it might mean that I would be a 4/10 in my life. Through this, I discovered three things that were truly critical for my happiness:

1. Deep Challenges

It is important to be constantly challenged. I had to do scary shit, and when I did, I was happier. It didn’t always work out, but pushing boundaries helped me to continually grow.

2. Deep Relationships

When I cultivated and built relationships, I was happiest. So often when I was overwhelmed with work, I would focus more on promotion and opt out of friendship and family. I had to spend time with those I loved to be happy.

3. Deep Reflection

I had to be true with myself about who I was and what I wanted to focus on. I loved technology, but I also loved design. I loved uncertain and messy emerging markets, and I loved cannabis.

Those insights led me away from Google and towards creating something altogether new. They led me towards a new journey of being a CEO, working with my father and working in an area that I love. Most importantly, they led me on a path of discovery that has helped me find fulfilment and happiness, or at least a direction towards it.


So, I finally exhaled deeply and answered Jonathan’s question.

“With a million dollars, I’d build my own business.”

Alan Gertner is the co-founder and CEO of Tokyo Smoke.