The Future of You

How to not regret your career in ten years.

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Tetris is one of the most popular video games ever created. The point of the game is simple: different shapes fall from the top of your screen to the bottom, and you rotate the shapes to fill horizontal rows. When a row is filled, it disappears. The goal is to eliminate all pieces before any of them reach the top of the screen.

As you progress through Tetris, the game gets more difficult. New pieces appear and fall quicker and quicker. Eventually, no matter how skilled of a player you are, you will lose.

You can't beat Tetris. You can set new high scores, and you can compete with your friends. But you can't win.

We humans are attracted to shiny objects: prestigious job titles, high salaries, material goods. But these ambitions are rarely driven by a pursuit of happiness; they are often driven by a pursuit of status.

Status is a dangerous game, because status is relative. If you win this level of the status game, whether that means making a certain amount of money, working for a certain company, or landing a certain job title, you merely enter a new level. Now you are comparing your status to even more successful individuals. Maybe you win that level as well, but the cycle never stops.

You can spend your entire career playing this status game. Grinding away for years to achieve brief moments of satisfaction, just to hop back on the treadmill and repeat the cycle once again. It never ends. Even the richest men in the world, Elon Musk and Jeff Bezos, have petty disputes with each other.

Your career is Tetris: no matter how well you do, you will never win.

If your primary motivation for pursuing a career path is to "win" the game of success, you have lost before you left the starting block. If you "win" the rat race, you're still a rat.

You shouldn't play the game to win, you should play the game for the sake of playing.

So the correct question isn't "How do I win the game?" The correct question is "How do I find a game worth playing?"

Predicting the Future

Are you going to be satisfied if you stay on your current career path for 10 years?

A heavy, but important, question. From ages 22 - 65, we spend the majority of our waking hours working. You don't want to wake up at 45 and realize you wasted half of your career chasing vanity.

Say you're a 24-year-old analyst for McKinsey & Company. For someone fresh out of college, your pay is great, and your resume is stellar. The work might not be the most engaging (no one's highest calling in life is updating decks that tell companies to lay off staff to cut operating costs, after all.)

However, you do have to earn your stripes. As you move to associate, manager, and principal, the work will grow more interesting. The pay will increase. Tedious deck updates will become engaging strategy planning.

Or at least you tell yourself that.

Sure, the pay is better. But do you really want to fly business class to different cities every other week ten years from now? Is the increased compensation worth the stress and pressure of dealing with difficult clients and demanding deadlines?

Will you actually enjoy this? Or do you just like the idea of this?

There's no way to know, with 100% certainty, if you will be satisfied if you stick with your current career for 10 years. But we can develop a pretty strong hypothesis.

Just look at those who are ten years ahead of you.

The managers and principals who already went down the path where you find yourself now. Are they satisfied and content? Or stressed and in denial?

Are they pursuing the career that they want, or does inertia have them trapped on a hedonic treadmill they can't escape?

Your career experience in ten years will likely be similar to that of your superiors now. If most of your higher-ups seem happily engaged, that's excellent. Stop reading this now.

But if your superiors seem disinterested, stressed, and above all else, stuck, that should be a massive red flag. If you're on a train and you see a "DANGER: BRIDGE OUT AHEAD" sign, are you going to ride the train off the cliff?

Don't assume you are the exception to the rule. If the majority of your supervisors aren't happy with their careers, there is a good chance that you won't be happy in the same role in the future either.

Invert, Always Invert

The first step to finding what works is avoiding everything that doesn't. Charlie Munger uses the term "invert." To quote the investor:

Invert, always invert: Turn a situation or problem upside down. Look at it backward. What happens if all our plans go wrong? Where don’t we want to go, and how do you get there? Instead of looking for success, make a list of how to fail instead. Tell me where I’m going to die, that is, so I don’t go there.

Charlie Munger

To find the path that you should take, you need to actively avoid the paths that you know you shouldn't take. This doesn't necessarily mean quitting your job on a whim. You do still need an income, after all. But this does mean you shouldn't look for new opportunities on paths that present the same problems as your current one.

If the consulting lifestyle sucks, you won't find the solution to your McKinsey problems at BCG. By actively eliminating the wrong paths, you are only left with potential right paths.

This idea of inverting works across all facets of life. Don't want to be overweight? Avoid unhealthy foods. Don't want to be a deadbeat? Avoid friends that sit around and smoke weed all day. Don't want to get cheated on? Don't date someone with a history of cheating. The most effective method for a good life is simply avoiding a bad life.

Finding The Right Path

Derek Sivers is a fantastic writer and all-around interesting human. His personal site is a goldmine of information. One of his life philosophies (and book titles) is "Hell Yeah or No."

Overwhelmed? If you feel anything less than “hell yeah!” about something, say no. We say yes too often. By saying no to almost everything, you leave space and time in your life to throw yourself completely into the few things that matter most.

Derek Sivers

Inverting is the "no." We actively invert to avoid the suboptimal outcomes. By avoiding the no's, we have the bandwidth to both find and pursue the "hell yeah's."

That's great, Jack. How do we find the "hell yeah's?"

Good question, hypothetical reader.

Find individuals who are making a living pursuing interesting paths, and see how they do it.

Here's an example from my own life. Around ~one year ago, I found myself entirely disengaged with my work. Beyond that, I saw my path to an unfulfilling future. Get my MBA, work in finance/consulting/banking, make a good salary doing things I didn't particularly like to impress people I didn't particularly care about.

I needed an escape plan.

I had been writing finance and satire articles online, and I realized that 1) I liked writing, and 2) I was good at writing. So I started looking around. Who was making money in this space, how did they do it, and did they seem content?

Over the next few months, a few examples stood out:

  • Packy McCormick and Mario Gabriele had turned their personal newsletters/blogs into high-cash flow businesses.

  • Morning Brew and The Hustle sold for millions to Insider and HubSpot.

  • Litquidity's Exec Sum newsletter was bringing in great money through ad revenue and merchandise sales.

  • Morgan Housel was hired by Collaborative Fund to write full-time for them.

Four very different paths, but they all shared three similarities:

The "business" was online written content. They were all making good money. They all seemed to enjoy what they were doing.

Path found.

The next step was obvious: I needed to write. A lot. Which led to the creation of this blog that you are reading now. I didn't know where this writing thing would go. Hell, I still don't know where it's going to go. But I do know one thing:

I value autonomy and creativity, and writing provides a way for me to make a living while hitting both of those targets.

Most of you won't be writers, and that's okay. This framework is career-agnostic. Figure out what interests you, find people pursuing that path who appear both satisfied and successful, and see how they did it. No two paths are identical. But you can derive lessons from others and inject your own flair.

I'm not going to be the next Packy, Mario, Morning Brew, Hustle, Litquidity, or Morgan. But I can take lessons from all them to create the best "me."

Ask yourself four questions:

What interests you?

Who makes money doing that thing?

How do they do it?

Do they seem happy?

Once you find your "Hell yeah," go all in.

Life rarely offers us a clear glimpse of the future. If you can see yours, don't ignore it.

- Jack

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