On September 27, 2018, I was offered a job that would pay over a million US dollars — multiple times my last pay-check and equity package — with upside that might lead to "screw you" money in a few years.
I said no.
And what the hell? That's a lot of money. Am I stupid? What was the job? Were they going to just flog me for a year?
Without breaking confidentiality, it was to help build a marketplace business in another part of the world, covering around 100 cities across a large geography. It would be an executive role with a huge budget, almost unlimited authority and a lot of independence. Finally, it was working with a good friend of mine, someone I trust and like and would never let down (as he wouldn't me). The company founders (entrepreneurs and VCs) de-risked it for me.
It was a dream job. The problem was, I no longer wanted a job, so I chose to turn it down.
I chose my own destiny
As I said in my goodbye letter to Lyft earlier in 2018, I'm not a great employee. That's why I'd have been good at this job. They specifically did not want to micromanage me. However, I'd still have been building someone else's dream, when it was time for me to follow my own.
Earlier in the year, I had promised myself that I would start my own business and go travelling with my partner, Jo Hyun. 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, we had both aspired toward similar things: to run companies. 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 weren't sure what we wanted any more, so we went away for a weekend.
We looked back at our lives and thought about our most vivid memories: when we had struggled. The times we were forced to learn and adapt. Like when living abroad in a foreign environment, or trying to overcome a weakness. 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. More life skills, from Latin dance to emergency motorcycle repairs. More cultures, 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 spend a year travelling to unfamiliar, uncomfortable places, studying languages and skills, and learning more about the world? 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 is to do this, 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."
How's that for a résumé?
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.
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.
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 Jo.
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, didn't get to it, and so it was easy to sayxw 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 sustainable future.
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, she didn't keep to her promised 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.
For a good decision: 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 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 paycheck during university... bring it on. But I was afraid it 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, 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.
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.
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