The one question that I ask myself

When I was young, I avoided risk and conflict.

My brother broke his arm while playing. He was climbing a tree and lost his grip. That just wasn’t me – I would never do that. I would never climb a tree!

When my parents argued and their shouts became intolerable to my ears, I would retreat to my room. I turned up my CD player to drown out the sounds of fighting.

Even though I was the older brother, my brother was physically stronger than I was. So I never wanted to fight him. Why get hurt?

I never wanted to try anything that was new, because that might make me look stupid. Or incompetent. Or cause either emotional or physical pain to myself.

I stayed inside my comfort zone for many years. Each day, I would be content with where I was. It was enough to be where I was, but not where I needed to go.

Fast forward to the start of my working life. I was working in Vancouver, Canada for a large national corporation. The company was one of the biggest telecoms in the country, and I was enrolled in its Leadership Development Program for new university graduates. After the Development Program ended, I found a permanent role in the company as a project manager.

It was hard work. I made lots of mistakes and wondered if I was causing too much emotional anguish on myself. Others in the program had picked easier paths to “graduate” into. And here I was, feeling like I didn’t have a good grasp of where the project was going. Everyone I worked with on the project team was significantly more experienced than I was. I wasn’t even sure if I had their respect.

Some days, I left the office completely drained. My instincts told me that I could have picked something much easier. After all, I was making the same paycheck as a lot of other people did in different roles. Why did I choose this? Why did I choose to suffer?

Nonetheless, I stuck with the role for about a year. A year turned into a year and a half. Eventually, I became competent at what I did, and the feedback from my peers provided validation.

You might be thinking – is this all that I am going to write? That one should stick with a challenging role and level up in one’s career? To never give up?

No, that would be too easy and self-serving. The hard thing is what came next.

I had “made it” as a project manager in this company. I was junior but learning the ropes. Things no longer felt overwhelming.

John Lennon said, “Life is what happens while you’re busy making plans.” Sometimes, opportunities materialize and you have no choice but to react to them. It is not about being ready or not – it is about timing. And reacting meant making quick decisions and then living with them. Owning the decision for the rest of your life. It meant eschewing comfort zones that previously existed – the virtual room that I made for myself that I could retreat to. The virtual CD player that I could rely on to drown out the sorrows in my life.

My boss decided to leave for a startup. He was going to be one of the co-founders of a new venture, and asked me if I wanted to join him there. If I joined, I would be the first project manager at this new startup. I would be employee number fifteen.

I was concerned, confused and secretly afraid. Was I really going to leave a “stable” job at this national corporation and go on the path less travelled? I concocted nightmarish scenarios in my head:

What if the company bankrupted six months into my stay there?

What if my current experiences were a complete waste?

What if the one-and-a-half years I spent here were completely inapplicable to the new environment? 

What if I couldn’t get along with my new coworkers?

What if I had to work an extreme amount of hours there, to the point where I wouldn’t get enough sleep? (This one was actually true.) 

What if what if what if what if what if—?

Before I had to make my choice, I talked to a senior colleague on my team. He was a mentor figure for me and someone I had a great deal of respect for. I observed how he handled situations; he was always cool under pressure. He wore his emotion on his sleeve, but he was as cool as they came. He seemed to have the answers, anyway.

I told him about my “dilemma” and asked him what I should do.

He thought about it for literally two seconds. “James, you have nothing to lose. Take this startup job, and if it doesn’t work out, you can always come back. You’ll learn so much there that it will be worth it, guaranteed.”

At that point, a light bulb went off in my head. I realized that my problem all along had been the fear of failure. I was afraid of what others would think. What my family would think. If I stopped bullshitting myself and was honest…the worst case scenario was not even that bad. I could always figure something out. But what I needed to do first was break out of my cocoon.

The question I started asking myself then – and continue asking myself to this day – is:

What’s the worst thing that could happen?

Is the worst thing just the fact that I might have to find a new job?

Is the worst thing just the idea that I might be fired, and not have a paycheck?

Am I really just concerned about the money?

Drilling into my concerns, one by one – and figuring out the “worst thing” that came from the previous “worst thing” – brought clarity. And I started to think about it another way:

What’s the worst thing that could happen—and what’s the best thing that could happen?

Not pain avoidance. Not anxiety avoidance. Rather, balancing the short-term uncertainty versus the long-term reward. I knew from my time as a project manager that one had to work for certain things. From the moment I joined the company, we were told one thing: “the rewards would come.” I always perceived that statement as trite, but now it made sense.

Fast forward to now. I live in China and am married to a wonderful woman. I am also just starting a new path in my career with a team of great people.

I have developed so much as a person – both professionally and personally. I have broken out of that safe zone that I once occupied in my Vancouver, Canada bedroom. Where I tried to drown out the sounds.

Over the past few years, I’ve worked on a number of mobile product management roles. I’ve worked with hundreds, if not thousands, of amazing talents from all over the globe.

The tipping point for all this was joining that startup company. If I had not done that, I would not have known how to work with clients. I would not have known how to build and promote mobile apps. I would not have been exposed to subsequent opportunities, and meeting my wife.

I still go back home. Vancouver is still important to me. That bedroom still exists in my mom’s home. But I am in a different place now.

What I did was ask myself: what’s the worst thing that could happen?

We all have our definition of what is tolerable. My only suggestion is to define what your “best” and “worst” thing is. Figure out what that is, and then push yourself to take chances. Be comfortable with facing your inner “worst thing” straight in the face, and not walking away.

It is the only way to live. And you can be so much more than you are now. The option is always on the table – you just have to reach out and grab it.



One Comment

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  1. Nice article, James! Very encouraging !


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