Be ruthlessly honest about why you work

Q: What is your relationship to work?

My answer to this Q has changed drastically over the years. I used to believe:

1. Work is about being successful. To climb the career ladder, get a corner office, and earn a prestigious title.
2. Work is about getting rich. To become financially independent and have F you money.
3. Work is about enabling our ideal lifestyles. To dictate where to live, when to work, and what to work on.
4. Work is about having a good-enough job. It shouldn’t be your life mission.
5. Work is about balance. We need to make $ to survive and pursue our real lives (friends, family, hobbies) after work.
6. Work is about finding meaning. To give us a reason to wake up in the morning.
7. Work is about using our biggest gifts. To naturally express ourselves in any job we do.
8. Work is about security. To have a steady paycheck, health insurance, and a retirement plan.
9. Work is the best opportunity to have a positive impact on the world. To solve the world’s most pressing problems.
10. Work is an infinite game. To find work that feels like a game you never want to stop playing.

I’ve spent YEARS trying to figure out the right answer. The smart answer. The ideal answer. I thought that once I picked something, I can optimize my life around it, and then forget about it.

Turns out, it's not always that simple.

Your relationship with work isn't a math problem

My career used to be my #1 priority. So I optimized everything to develop my skills and build my network in the startup world. Then I had a taste of being a digital nomad and all I wanted was freedom. I rejected chasing status, prestige, and fame in pursuit of owning my time and location. I wrestled with the guilt of privilege, esp. during the pandemic, and considered working for a non-profit or joining the Peace Corps.

I accepted a job to set roots in Toronto and build community there. I took two different sabbaticals playing chess and dancing bachata where I barely “worked” but I used my natural gifts every day. Today I currently have a FT job that gives me balance with a mix of freedom, meaning, and making $.

(This is the tl;dr verion of my career.)

There’s no straight and pretty trail to the top of some mountain.

I'm jumping on different lily pads. Swimming in the ocean. Getting lost in the city. Biking along the coast. Making dozens of seemingly random pit stops.

OK my life isn't actually that cool. But my point is that I'm constantly experimenting. I correct my course whenever I feel misaligned (which is always happening).

Our relationship with work isn't a math problem that can be solved.

Sure, there are frameworks to guide us. And questions to help with introspection. But it's up to the individual to go out in the real world and test out what works for them.

We're all just seeking permission to live differently

I remember working remotely for the first time in 2016. I thought it was so freeing and amazing.

• I never dealt with traffic.
• I went to the gym and grocery stores during non-peak hours.
• I had the opportunity to travel if I wanted to. Or to work locally from my favorite cafe.

I told my friends about working remotely at that time but no one gave it much thought. Working in an office was always the norm.

My mom drove 2+ hours every day for work. I told her that she can work remotely and not drive in rush hour traffic anymore. But she didn't want to rock the boat with her employer and reassured me the drives weren't that bad.

Then COVID hit and her company finally had to let their team work remotely. And my mom LOVED it.

No more driving in rush hour traffic. More flexibility. Ample time to pick up my little brother from school and walk in the park. I told her, "Mom, this is what I was trying to tell you. back in 2016!" Nowadays, this is all mainstream and people are turning down jobs that don't prioritize remote working.

But I have a sneaky suspicion that my mom always wanted to work remotely. She was just waiting for permission.

Even though I've chosen an unconventional life path, I relate a lot to my mom. I remember asking my coach,

“I want to do X, Y, and Z with my life. Am I allowed to live like this!?!?”

My coach: “You can do whatever the F you want lol.”

OK she didn’t use those exact words. 🤣

I was basically seeking permission from my coach.

Can I do this thing that I really want to do but it's a bit different from my friends' paths and kind of niche? Pretty please with a cherry on top??

Luckily I've had many supportive friends, mentors, and coaches who have wholeheartedly encouraged me to follow my bliss. I know everyone may not have that kind of social support.

I believe a lot of people know what their ideal relationship to work would look like. But there's a resistance to course-correct, even when they know they're misaligned. There are likely opportunities to

• Take a sabbatical with no agenda
• Accept a lower-paying job to be able to work remotely
• Move down from a more senior role to a junior role, but learn something you're actually interested in

Some people may respond with,

“But what about the $ I’m leaving on the table if I take a sabbatical? How will I find another job again?”

“How am I going to explain to my parents that I make $Xk less at my new job?”

“My senior role pays me well and people respect me. Doing a junior role again would feel like I’m starting all over.”

It’s always the same thing–the immediate costs of one’s decision.

Some of the concerns are legitimate and worth thinking through. But what’s equally important but not nearly talked about enough is the flip side–the cost of inaction.

If you don’t make this change, where will you be in one year? Five years? Ten years? You’d probably be repeating a version of your miserable situation. This is hell on earth for me.

On the upside, what can potentially happen if you make this change? What would your life look like in five years? Ten years? Potentially transformational.

"We think a lot about those black lines, forgetting that it’s all still in our hands." -Tim Urban

Humans grossly overestimate risk.

• Leaving a job can be risky. But if you have savings and a roof over your head, taking 3 months off every 5 years will probably not ruin your life. If you need to you can live cheaply, maybe in a different country, and see where your heart takes you.
• Starting a business can be risky. So don't invest $50k in fancy branding or a storefront. Start with small, low-cost experiments to validate your ideas. You can do this while you're still working your FT job. Most ideas will fail but keep trying new projects, and then double down on what's working.
• Dropping out of university can be risky. Every older person told me that I'd regret dropping out one day. But it actually wasn't risky at all. At 19 I lived at home, didn't go into debt, and ironically earned $ from my internships which led me to real startup jobs.

A lot of things actually aren't as risky as we may perceive them to be. To help calm my anxiety, I like to ask myself: what's my worst-case scenario?

• I take a sabbatical and learn nothing. Or I run out of money. OK time to find another job.
• I take a year to find a profitable business idea. But the experiments don't lead anywhere. OK I gave it a shot and it didn't work out. Time to find another job.
• I drop out of university and I'm not making any progress in my career. Or I'm not learning things I want to learn. OK I'll enroll back in school.

We overestimate risk when in reality, it's rarely life or death. We're not on a submarine here, people. (is this joke too soon?)

I don’t recommend you to “quit” or do anything drastic right away. Just don’t be like my mom who continued to drive hours in rush hour traffic every day for 30+ years before discovering remote work.

Get ruthlessly honest with yourself.

1. What is your ideal relationship to work?
2. What's the cost of inaction of staying where you are?
3. What's the upside of doing a small experiment? Or making a big change?
4. What's the worst-case scenario? What do you really have to lose? And at the end of the day, who cares what other people think?

If you're looking for permission, this is it. Your writer friend Tam waving a magic wand granting you a signal to go for it.

Think about it, but not for too long. Best of luck. 🪄