The Case for Living Life Backwards

Take advantage of hindsight before you get there.

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Last week, 40,000+ investors, from hedge fund managers to college students, flocked to Omaha, Nebraska to attend the Woodstock of Finance: Berkshire Hathaway’s annual meeting.

While the only requirement to attend this meeting is ownership of Berkshire Hathaway stock, few investors made the trip to Omaha to learn more about their company’s Q1 revenue beat or forward guidance. No, they traveled to Nebraska to learn from Warren Buffett and Charlie Munger.

Each year, Buffett and Munger spend hours answering questions from the crowd about all sorts of things, from the impact of Covid-19 on the economy, to the implications of interest rate hikes, to the duo’s skepticism about cryptocurrencies.

But their most valuable insights have little to do with macroeconomics, and a lot to do with life.

This year, when asked about the key to living a good life, Buffett offered a prudent suggestion:

“You should write your obituary, and then try to figure out how to live up to it.”

At first, this recommendation might seem weird. Morbid, even. Why the hell would you spend even a moment of your 20s contemplating what a local newspaper might write about you 60 years from now?

But there might be something to this idea, considering that Buffett isn’t the only billionaire who subscribes to this doctrine of planning one’s life in reverse.

Years ago, when asked why he left his hedge fund job to start Amazon, Jeff Bezos said the following:

“I wanted to project myself forward to age 80 and say, ‘OK, I’m looking back on my life. I want to minimize the number of regrets I have.’ And I knew that when I was 80, I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed, I wouldn’t regret that. But I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day.”

And stepping away from the realm of billionaires, I first heard something similar two years ago from a mentor of mine: Dr. Jim Jackson.

Let’s turn back the clock back to February 2021, a few weeks before my 24th birthday. (Stick with me, I’m about to get ridiculously introspective for a moment.)

The first 23 years of my life were heinously simple:

Make good grades in high school and graduate as Valedictorian. Play football in college, keep my grades up, and get accepted to a top business school. Maintain a solid relationship with my girlfriend and work a steady corporate finance job for 2-3 years until I can start business school.

The rest of my life seemed pretty straightforward, too.

When I’m 25, move to New York, enjoy my first year of business school, and land a coveted internship for the summer. Finish school, accept the return offer, and bask in that sweet, sweet, post-Columbia paycheck. Climb the corporate ladder, get married, probably move to Alexandria, VA, Alpharetta, GA, or Charleston, SC. Have some kids, make bank, coach a little-league softball team, send my kids to the school of their dreams, and live happily ever after. The end.

But there was one problem: As I approached my 24th year on this planet, I wasn’t so sure about the whole “rest of my life” plan. In fact, I was drowning in indecision.

A lot happened between February 2020 and February 2021 that changed my perspective on, well, pretty much everything. As some of you know all-too-well, I made a lot of money trading gambling on SPACs. There’s nothing like making 7x your salary by mashing buttons on your phone to make you reevaluate your career ambitions, and I became pretty lethargic toward my job. Of course, the money itself also made me miserable because I couldn’t take my eyes away from my brokerage account for more than 10 minutes.

Then let’s bake in the monotonous cycle known as my weekly routine: look at spreadsheets, pretend to be busy during work, hang out with my girlfriend a couple of times, and go out with my friends at the same bars every weekend, rinse and repeat.

After a year, I was doing the exact same thing in February 2021 that I was doing in February 2020, and that terrified me. Sure, I had made some money, but I was miserable. Worse than miserable, I was bored. Seriously, who gives a damn about money if you aren’t doing anything interesting with it?

This induced an existential crisis of apocalyptic proportions as I saw myself cruising through life on autopilot, doing the same stuff for the next 40 years until I retired at 65 wondering, “Where the hell did my life go?”

Combining this realization with the stress of moving to New York for business school in 18 months, now having no idea what I wanted to do with my career, my relationship, and pretty much every other variable of my life, and my thoughts became consumed by one question that just wouldn’t go away: What the fuck am I going to do with my life?

*Pardon my French, but come on, we’ve all had that thought*

Still with me? Cool.

Thankfully, my mom must have sensed my underlying existential angst, because that February, she introduced me to Dr. Jim Jackson, a friend of my grandparents who had spent his career as a pastor, author, and, most recently, executive coach.

Not a bad guy to chat with.

We scheduled a call, and after spending a few hours aimlessly driving around Atlanta, I pulled into a parking garage and dialed his number. I wasn’t really sure what to expect going into this conversation, but after we made our introductions, he asked me, “So, what’s going on?

I then proceeded to hit him with a borderline-schizophrenic word tsunami covering everything that had been weighing on me for the last several months.

There was a pause, and I half-expected to hear the dial go click. But he didn’t hang up. Instead, he chuckled, took a deep breath, and said, “You’re going to be alright,” and we spent the next hour breaking everything down.

To be completely honest, I don’t remember many specific details from the rest of our conversation, but I do recall one quote word for word:

Begin with the end in mind. What do you aspire to be and do before you would be willing do die?

Sound familiar?

I believe that when you hear good advice once, you should pay attention. When that same advice is repeated twice, you should implement it in your own life. And if it’s echoed three times? Well, you would be a fool to ignore it. And I would hate to be a fool.

“Well damn,” I thought. “I have no idea what I aspire to be and do.”

But that was okay. No one really knows what they want to do at 23. But after this conversation, I began to reframe how I looked at life.

I’m impulsive, sometimes to a fault. I’ll say yes to a trip without first checking my calendar, I won’t hesitate to make an ass out of myself if I think it can generate a laugh, And I have no qualms with occasionally spending an irresponsible amount of money if I think the experience will make for a good story.

I am an evangelical supporter of “living in the now,” so you might think that “starting with the end in mind” is hypocritical.

It’s actually the opposite. The truth is, starting with the end in mind is what empowers you to take full advantage of the present.

We have never had more optionality in our careers, relationships, hobbies, and life pursuits, which makes commitment and focus damn-near impossible. It’s easy to get caught up in the day-to-day hustle of life, either saying yes to any and every opportunity that emerges or retreating to our routine in the face of overwhelming optionality.

But the “yes man” and the “no man” are just two sides of the same coin: instinctual reactions to an abundance of freedom.

That’s why starting with the end in mind, or living life backwards, is so powerful: it helps you define which choices you should and shouldn’t make in the face of unlimited variability. Once you define the final product, you can reverse engineer it to make it a reality.

After my chat with Dr. Jackson, I spent some time identifying my values, and more specifically, the things that I wanted to have accomplished or experienced by the time I was 80. A few of those values and goals are as follows:

  • Make enough money to never have to worry about finances.

    • Don’t sacrifice freedom and control over my time for additional income that won’t meaningfully improve my life.

  • Don’t take life too seriously, and don’t surround yourself with folks who do.

  • Maintain lifelong relationships with my closest friends.

    • Call your close friends at least 2x per month, even if it’s just to say what’s up.

    • Make at least 1 trip annually with your college/graduate school friends.

  • Time is finite, money isn’t, so never turn down an invitation for something that could make a good story because it “costs too much.” Money is worthless if you don’t use it, after all.

  • Travel as much as possible throughout your life, the world is a lot bigger than the state of Georgia.

    • Take at least one extended solo trip when you’re young so you can see the world as it is without the influence of others.

    • Travel cheap when you’re young, because hostels and dive bars are filled with more stories and friends than resorts and Ritz Carltons.

    • If you’re traveling with others, good company always beats a “good location.”

  • Learn a foreign language. Most of the world can speak at least two languages, and it’s bullshit if you die without acquiring a new one as well.

  • In your career, never choose short-term financial upside over long-term leverage.

  • On a similar note, never make a career decision out of fear of uncertainty or perceived “risk.” You’re already dead anyway, who cares about “risk?”

  • Opportunity costs drive everything, and life is defined by seasons. Do the dumb, fun, adventurous stuff when you’re young, so you can laugh about it when you’re old.

    • Spending your 20s rejecting adventure for the sake of security, and spending your 40s chasing the adventures you missed when you were younger is a recipe for misery.

  • Never stop writing.

  • Stay in good physical shape for as long as possible.

    • Play sports for as long as possible.

  • Have a loving, fulfilling marriage.

    • Don’t stay in a relationship just because it’s comfortable or you think it’s what you’re “supposed to do.”

    • You never know when you’ll meet the “one,” and you’re already not going out with the girl across the bar, so you should probably say hey. It’s not like you “can’t go out with her” more.

  • Never stop reading.

  • Being scared to do something is a very good sign that you should do that thing.

There’s more to this list, and these ideas have evolved over time, but you get the idea. When you start with the end in mind and define what will have been important to you 60 years from now, it’s much easier to cut through the noise in life and optimize for the stuff that really matters. It’s like taking advantage of hindsight bias before you actually get there.

No one’s obituary ever said, “In his golden years, he was happy that he played it safe,” you know.

- Jack

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Jack's Picks

  • I’m co-hosting a VC/startup/anyone doing cool stuff Breakfast Club meet up with Morgan Barrett and Ariel Purnsrian on Wednesday, May 24th! Want mingle with 200+ folks doing cool stuff? Check the link here.

  • My man Danny Miranda had a great chat with Tucker Max, the author of I Hope They Serve Beer in Hell.

  • The Atlantic’s Annie Lowrey interviewed sociologist Jacy Reese Anthis to break down what sentience actually means, with regards to AI.

  • I enjoyed this Tim Ferriss interview with Kevin Kelly.

  • I also just finished Kevin Kelly’s Excellent Advice for Living, a compilation of life-advice quotes that he has published over the last few years.

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