Why You Should Chase Interesting Problems, Not Money


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In the HBO television series, Silicon Valley, there’s a roof where employees go to “rest and vest.” The show displays engineers who don’t do any work, but stay employed to allow their stocks to fully vest. Engineers presume to stay at the fictional company until their stocks turn into life-changing money. You might be thinking, “there’s no way this is true in real life.” The funny thing is, FAANG companies do this all the time with engineers. One of the most common reasons is to make sure engineers don’t leave to work for a competitor. To do this, the company will give the engineer stock and lighten their workload.

For some, the “rest and vest” life is the dream. I acknowledge that life-changing money is a strong motivator to stay with a company. That said, if you’re looking for a satisfying career, money won’t help you. My contention is that you should focus on solving interesting problems over money. You should do this when given the choice. The rest of this article will cover the untold truth behind chasing money. I’ll also unpack why solving interesting problems will foster more life fulfillment money. Finally, I’ll provide a few edge cases for where my logic breaks down 🙂

The Dirty Truth Behind Chasing Money

A job where you make a lot of money can be a great asset. You can buy a healthier lifestyle and spend more time doing the things you enjoy most. Money can also create opportunities for your kids to have a turbulent-free life. There’s no doubt that having a job that pays well is a good thing.

That said, when it comes to life satisfaction in a career, money only goes so far. Money helps you rationalize staying at a job where you’re not happy. But in the long-term, no amount of money will make you love your job. The hours of unhappiness add up over time. Every email, meeting, or project you take part in will only exacerbate the fact that you don’t like where you are. If you’re working ridiculous hours the money you’re making begins to feel like a lot less. You’re working more hours and decreasing your hourly rate. But you’re also taking on the opportunity cost of being able to do something else. This cost could include things like hanging out with family and friends.

If you’ve had the privilege to work on something you love, then any job thereafter will pale in comparison. You’ll know exactly how it feels to do something you’re genuinely passionate about. Every day feels like something great could happen. You’re filled with an optimism that things are going to move forward. You’re excited about the possibilities and opportunities in front of you. Once you’ve experienced these things, it’s hard to work a job without them. You’ll feel this way no matter how much money you’re getting.

Why You Should Chase Interesting Problems

Years ago I was struggling with my career. I didn’t know where I was going and I didn’t like where I was in life. I made a few money-driven decisions and I didn’t expect how unhappy those decisions would make me. A friend happened to drop into town and texted me to grab dinner. I ended up sharing how I was feeling and she gave me the advice I’m about to share with you here.

She asked me, “what kind of problems do you enjoy solving?”. The question caught me by surprise. It had never dawned on me that solving interesting problems could fix my dissatisfaction. At that moment I started thinking about the problems that sounded most interesting to me. I started thinking about talent acquisition inefficiencies and community development initiatives. That week I began to work on solutions to problems I found the most interesting. I started experiencing a deep sense of worth and passion that drove me to wake up each day with expectation. The crazy thing? No one was paying me to work on those solutions, yet I was happier than I’d ever been.

This is my encouragement to ask yourself the same question. If you’re struggling with satisfaction in your work, what kind of problems do you enjoy solving? Those problems don’t have to be a different job. What problems can you solve in your current role? Who can you collaborate with to make your current situation better?

Edge Cases and Why I Could Be Wrong

There are several edge cases that prove my contention is wrong. The first one that comes to mind is a job where you make a lot of money, but it’s also a job you enjoy. In this case, the recommendation to chase interesting problems doesn’t quite apply.

Another edge case that comes to mind is situations where you have to chase money. I get it. We all have bills. Prioritizing interesting problems is a privilege that not everyone gets to experience.

The third edge case that comes to mind is situations where you don’t know what problems you’d like to solve. This is very valid. In this case, I recommend you start trying to try different things. Try to better understand what problems interest you the most.

Interesting Problems FTW!

At the end of the day, you have to make your own decisions. After all, it’s your career! When I started chasing interesting problems over money I felt happier. I don’t know if I’ll ever “rest and vest”, but I know that I’m not dependent on money to determine my happiness. I’m looking forward to the interesting problems I’ll have the opportunity to solve!

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