Think Longer

An early mentor at one of my internships gave me the advice to “Think Longer”. It might be the best piece of advice I failed to take seriously.

During university, life happened in 4-month increments. 

Every 4 months alternated between school and internships. Thinking ahead meant considering the next term before it happened. During a school term, you would interview for your internships, and during the internship you would pick your classes for the next term.

This made life rather simple. At the beginning of a term you had clear goals and objectives: work hard, learn as much as you can, and don’t fail the class or get fired. This system became so deeply a part of our lives that we would joke about the mythical “5th month”: the feeling to be in a job past the 4-month deadline.

When I graduated, I joined an early-stage hardware company called Mosaic Manufacturing. I moved to the big city, rented an apartment, and began my career. I had mastered the 4-month project cycle and thought it would apply to my first job. I quickly realized the problems we were solving required years of development. 

My plan was to build a product with Mosaic, and then leave for bigger adventures. I expected it to take 18 months. I remember meetings where we confidently said things like “We should have this in production in 9 months.” How naive we were.

4-month cycles didn’t apply in this new paradigm. I ended up working at Mosaic Manufacturing for over 3 years before moving to Nymi where I’ve been for the last 2. I never thought I would live in Toronto for a combined 5 years of my life, but that’s how these things go.

Looking back there is a clear trend that I was too naive to see: the time horizon gets longer.

In grade school, life happened days at a time; in high school, weeks at a time. University happens 4 months at a time, and when you graduate and get your first job, the projects will take years, so that’s how you’re likely to start thinking about your life.

Now that I’m 5 years into my career, I’ve started seriously thinking about what the next 5, 10, and 20 years look like. Careers tend to happen in decades, and when you think about having a family and doing work that lasts, time horizons can look even longer.

Over the course of a career, your time horizon will grow organically. 4-month chunks will grow into projects, years will grow into decades. Long-term thinking is a superpower, and for most people, it takes a lifetime to come to this realization. You can short circuit that development by starting now.

Long-term thinking forces you to consider lasting consequences. It encourages losing the battle in order to win the war. 

A classic example is investing: don’t spend your money now, put it away so it will grow and be worth more later. 

But perhaps a more subtle example is relationships: asking yourself if you would want to be in a relationship with this person for the next 20 years is a powerful filter. Naval Ravikant has encouraged his followers to “play long-term games with long-term people”. For me, this means finding people who are willing to stick things out when times get tough. 

Even in business, long-term thinking flexes its effectiveness. Warren Buffett’s investment strategy has famously been to buy and hold, and hold, and hold. He buys into companies for the long term. 

For me, the most difficult area to apply this was my career. In finding my first job, it was nearly impossible to think about how it was going to affect the trajectory of my professional life. I was far too concerned with paying my student loans to think about my legacy.

Coming straight out of school, it’s easy to think that the rest of your life will happen in 4-month increments; that planning your life one season or quarter or project at a time will get you where you need to go.

In my experience, that is not true. 

It’s tempting to chase that next promotion, to optimize for the shortest path up the hill, only to discover you have arrived at the top of the wrong mountain. 

Without the clarity to think about where you are going, it’s easy to find yourself led astray.

As your career unfolds, you’ll begin to realize that each step on the journey takes you closer or further away from the person you want to be. One day you’ll wake up, older, experienced, and nowhere near where you expected to be.

Setting aside time to think about the future on a regular cadence is a strategy I have found incredibly useful. Asking the question of where I want to be when I’m 50, 60, or 80, has provided consistent clarity on the path, and helps me look past the daily difficulties. Pausing, and asking the question “Will I be proud of this choice in 20 years?” is often enough to give you a nudge in the right direction. Doing this consistently, day after day, is how to build a life you are proud of.

The future is full of uncertainty, and planning can often feel like a fool’s errand. Many of your best plans will run aground on the rocks of could-have-been. You’ll have to change and adapt and roll with the punches. But all of that said, nearly every bad decision I’ve ever made can be distilled down to thinking too short-term. Consequently, nearly every amazing decision I’ve ever made was a long-term choice. 

Long-term thinking is the only reliable strategy I know to predict the future. 

So my advice is this: think longer. 

Slow down. 

Take a deep breath. 

Don’t sweat the small stuff, and it’s mostly small stuff.

Plan, even if everything is bound to change.

And start thinking about your life in decades, because the decades are going to come faster than you think.

Thanks to Dylan Trebels and Emma Bartel for editing drafts of this essay.