On September 27, 2018, I made the difficult decision to turn down the job I had been working towards, to run operations for a large tech startup, and to rather “discover discomfort” — go travelling to unfamiliar places, learn languages, and try to connect with foreign cultures.
It was, as you might be able to tell from my tone, also one of the easiest decisions I had ever made in my life.
The job was, on paper, what my whole career (across multiple companies, countries and languages) had been leading up to. It was to run operations for a transport tech company across a huge geography, spanning what would eventually be over a hundred cities, and with a total pay-check of a million dollars in a year — with upside that might lead to “screw you” money in a few years.
Also, it was working with a great friend of mine, someone I trusted completely and with whom I knew I could have fun.
Why’d I turn it down? Am I an idiot? Maybe.
Read the other posts in this series on my path as a travelling entrepreneur:
In part, I turned it down for these views:
But not really. Yes, it was a dream job. The problem was, my dreams had changed, and I no longer wanted a job. I wanted something quite different.
I chose my own destiny
As I said in my goodbye letter to Lyft earlier in 2018, I’m not a great employee.
Perhaps that’s why I’d have been good at this job. They specifically did not want to manage me. However, I’d still have been building someone else’s dream, when it was time for me to follow my own.
Earlier in 2018, I had promised myself and my partner that we would start our own businesses and go travelling. We made this decision after going away for a weekend and re-assessing what was important to us in our lives. What did we want?
When we were younger, it was easier. We wanted to run companies. Now, we had the backgrounds for this, with advanced degrees and years of management experience. But as we advanced towards this goal, we found ourselves less and less interested in it.
We looked back at our lives and thought about our most vivid memories: they were all when we had struggled. The times we were forced to learn and adapt. Like when living abroad in a foreign environment, learning a difficult language like Chinese, or trying to overcome a fear like that of public speaking.
More recently, time seemed to be speeding up. With the same pattern week-to-week of rushing through the work week to live on the weekend, the weeks blurred into one another.
We thought about the kinds of things we wanted to learn.
- More languages. I had always dreamed of learning Arabic. We both became enamoured with the idea of learning an African language, Swahili, as a gateway to East African culture.
- More life skills. We wanted to spend time mastering Latin dance, beyond occasional one-hour Salsa classes. We wanted to learn martial arts, musical instruments and emergency motorcycle repairs (ok, that’s me).
- More foreign cultures. We wanted to spend time living in distant places, becoming familiar with the unknown until the people around us become our friends and those places feel like home.
So the question became: Could we do this?
Could we travel to unfamiliar, uncomfortable places, studying languages and skills, and learning more about the world, as our life?
Yes, we could.
So we started Discover Discomfort, a journal of living outside our comfort zones with the intention of intensely learning more about the world.
The plan became to travel, learn languages and pick up skills, and develop it into a self-sustaining blog business. That may work, if our plans go as we think they will. But if they don’t, after a year we’ll be able to say:
“We spent a year intensely learning a variety of awesome skills and wrote about how you can learn to do anything you set your mind to, publishing several books on the topic in the process.”
Ironically, as I spoke to one of the company’s founders (who had previously founded other companies), I more identified with him than as one of his employees. So it was easy to say no — I wanted to be in his position more than in my own.
(Oh and in case you’re wondering how much all this costs: about $50K for a year. We didn’t need a million dollars. So why take another job?)
I chose the scarier option
Often when presented with two choices, I find that one is certain but boring, and one is uncertain but fascinating.
I knew how to do the job that was offered to me. I methodically could go between cities, set up operations and build them into machines. I had done it before.
And while I had lived in unfamiliar places before, I had never done it as a way of life. I also didn’t know how unfamiliar the world could become. I had my ideas of what living in remote parts of the Middle East, Africa, Asia and Latin America would be like, but wasn’t sure.
Partly this is my huge appetite for risk, but I have learned that fear for me has two other meanings.
The first thing that fear means is an opportunity to learn. When I am afraid of something, it’s usually because I don’t know how to succeed in it yet. However, I’ve succeeded in enough things that I know that success is a choice and requires only one thing: to act as if I’m going to succeed.
The second thing that fear gives me is the opportunity to stare it down and show that I can stare down future fears. The more mountains I conquer, the more I know I can conquer in the future. This is exactly what brought me to this opportunity in the first place, and what gives me confidence that it won’t be the last – should I even want one again in the future.
Paradoxically, fear nearly pushed me to take the job. What if it was the last chance I ever had? What if I was throwing away what my whole life had led up to?
It’s important, in these situations, to know that it’s fear talking, to acknowledge it, and to let experience take over. While I felt like it was my last chance, I knew that it wasn’t. I know more opportunities will arise in the future. Better ones.
I chose my relationship
I predicted that the effect of me travelling for work, rapidly changing our life commitments and also abandoning what we were going to build together was going to dramatically affect my relationship with my partner.
This wasn’t just a guess, it was intuition built on experience. I knew the stress that this job would bring. I knew it’d mean time apart, and that takes its toll. Finally, it was difficult to consider breaking a pledge to do something that I was excited to do together.
Even though we both carefully considered the option together, knowing that a pile of money now could change the way we think about money in the future, I knew it’d never be a happy choice.
The way we finally thought about it was: what would be an amount of money that would be stupid and irresponsible (to future generations) to pass up? We decided on that number but never got to it in negotiations, so it was easy to say no.
I chose life
In the month since I had left my last full-time job at Lyft, I had regained so much of my life. I was focusing on things that I was passionate about — studying languages, building businesses, becoming fitter and healthier, reading, travelling, helping people — and woke up every day excited about the future.
I knew that if I took a temporary detour of a year building someone else’s business, the possibility was that it might quickly become two — for the same reasons. And every year I helped build someone else’s business would be a year less of building my own future and living my own life.
And that delay would come with another cost, which would be a year of me working 60+ hour weeks to build something else. Trading time for money (or “skills for skrills“, as I prefer to say). Even if it’s a lot of money, it’s the same deal.
I chose to listen to my gut
In the past, I had made terrible decisions because of money, and I had made great decisions when ignoring money.
As an example of a bad decision: In 2012, I accepted a job as COO of a family office/private wealth management company. I was wary about the opportunity because I wasn’t sure I fully trusted my potential boss, but the promise of wealth was huge.
Unsurprisingly, the person who offered me the job didn’t keep to the contract, and the payout was much less than what was promised (and documented), and brought with it torturous psychological games and requests for me to compromise my ethics. I learned what I could about finance (quite a lot, the good and bad), and left.
As an example of a good decision I made, ignoring money: In my earlier years, in 1998, I was offered a full-ride scholarship to the Australian Defence Force Academy (ADFA) to join the Air Force after graduation.
The Defence Force scholarship came with a huge stipend and a great guaranteed job. It was extremely tempting. The allure to serve my country, a job, a uniform, a pay-check during university… bring it on.
But I was afraid that a military job conflicted with what I really wanted, deep down, which was to travel during my university years and to live the life of a vagabonding student. After a lot of soul searching (consulting with others, I learned quickly, wasn’t useful – everyone is supportive of any choice I make because I have an amazing family!) I cancelled on the last day.
And, true to my word, I did travel, spending four years in total in Israel, Spain, France, New Caledonia and Italy. Yep. I made the most of it.
A second good decision: In 2016, knowing I needed (emotionally) to leave Hong Kong at the end of a long relationship, I took a job at Lyft, ignoring the lowest pay I’d had in years and knowing it’d be a place I could make friends and bask in the community. It paid off and I had no regrets.
I know I can’t always trust my gut, because of the lack of experience. But once I have experience, I need to acknowledge it, take the plunge and listen.
I chose to ignore my ego
I have a huge ego. It can get in the way of good decision making, and it nearly got in the way here.
For me, ego is vanity, the desire to impress others. Usually, this is impressing a group of other people that only exist in my head, and who I don’t even need to impress (either they’re already impressed, or whether they’re impressed or not bears no impact on my life).
The first thing I had to do was to acknowledge my ego is there, even though I shush it. I did this by saying to myself, actually writing down, then saying it out loud:
“I want to take this job to show all those jerks that I AM worth this much money. You think what you’re building in some other company as an employee is cool? How’d you like it if I did that, but all over half the world, with a huge budget and unlimited power and a massive title? Hahaha take that! See! You should have paid me multiple times what you were paying me! Your loss, suckers.”
Scary. There’s a part of me actually saying that. I’m embarrassed by it, but trying to own it. Who am I even saying it to? I think I’m saying it to the corporate world in general. To some degree I’m saying it to every former employer, stuck in its bureaucratic hiring and management process.
Ego is a terrible way to make a decision. It blinds us. I’ve had to learn the difference between values-based decision making and egotistical decision making. Values are things like wanting to be honest, to contribute, to learn, to be inspired. Ego is things like power, lust, wanting to do something because it sounds cool to an imaginary audience, to impress someone in your head.
How did I isolate my ego? I asked myself one question.
“If nobody knew what I was doing, what would I personally want to have done in my life?”
The answer: I’d want to choose my own destiny.
The final word… I chose to follow my heart
Every time I describe Discover Discomfort to a new person their eyes light up. “You have to do this!” they cry.
And while I don’t want to see the world through other peoples eyes, it certainly reminds me of how I feel myself.
Every time I presented the option of a new and well-paying job, people who knew me best would advise me not to. People who listen to their hearts, from mentors to family members.
Ultimately, when I thought about taking a job and giving up what we were doing, part of me wanted to just lie on the bed and cry.
And if nothing else was the nail in the coffin, that was it.
Retrospective — 18 months later
It has been 18 months since I made that difficult decision in September 2018.
Since then, we have
- Learned Egyptian Arabic
- Learned Swahili
- Gone running in Kenya, in the “Home of Champions”
- Learned to dance salsa in Colombia
- And… fled home to Australia due to the emerging Coronavirus pandemic.
During those 18 moths I did a few contracts for Wind. I got in, did some magic for a month or two, and got out. I was very happy to leave each time — the jobs were rewarding on a personal level, but the company had a level of top-down chaos that was quite unmanageable.
After finishing a few contracts, they offered me the COO position again. I spoke to a few people, but concluded that wasn’t the right move for them or for me.
Meanwhile, our blog is making money and we’re starting more and more web projects. The idea of going back to a 9-5 job seems further away than ever, which is why I tell people that maybe they don’t need to get a job.
The purpose of Discover Discomfort, meanwhile, has broadened. Our mission now is to connect people around the world and help us see through each others eyes, via language, culture, and guides to living in distant destinations.
If you want to join us on our mission, visit us at Discover Discomfort.