“The Robots Are Coming for Your Job” screams the headline.

You skim through the article on Twitter (you’re never calling it X) — partly grateful you’re not replaceable yet, partly pondering AI’s broader impact on employment and society. You sip your oat latte, while checking the clock for morning meeting time. Unlike Gen Z, you have discipline. You don’t wanna be late.

Something about the year and month catches your eye. Then you realize it. It’s been 20 years. 20 years since you first clocked in at the skyscraper where you started your first job. 20 years in the blink of an eye.

You have mixed feelings. You check the clock again. Still 15 minutes till morning standup and there’s nothing interesting on Twitter anyway. You allow your mind to drift…

Most Will Fail To Get Fast Money

Somewhere along the way, maybe around Year 16, you realized it.

Most of the side hustles didn’t work out. Most of the day traders lost money.

Everyone loves outlier stories, but the odds are against it. Your peers who actually made money did it in two ways:

• They launched a business and scaled it.
• They did it the old-school way. Earning more money by job upgrades and promotions, keeping their expenses reasonable, and saving + investing wisely.

You thought about launching a business yourself, but never dared to go all in — the risk/reward calculation didn’t make sense. Perhaps that’s why they say courage is the most important thing for a smart person. Otherwise you would rationalize yourself out of doing anything.

Should you have been braver and taken on more risk?

The old-school way of getting rich remains underrated. It’s tough to see because nobody wants to get rich in 20, 30 or 40 years. Everyone wants to get rich next month. But compounding is magical. What was once a flimsy concept is now real wealth you see among your friends who managed money wisely.

The Path Less Taken Is Also the Harder Path

It’s 2018. Year 13. You join a startup as Employee #1.

You’re a rebel — you hate doing things because everyone else does it that way. Everything is figureoutable. Even improbable career transitions. You prove a man’s education and history do not dictate his future.

But looking back, you’ve grudgingly learned there can be wisdom in the conventional path.

In another universe, you would have played pro football. Or toured the world with your band. Your talents however, were more suitable for the boardroom than the stadium.

Born to be an artiste, forced to create PowerPoint decks.

You made decent money though. Your parents were right. A top 10% guitarist in the country doesn’t make money from music. A top 10% accountant still drives a BMW.

You rebelled against the thought of maintaining a job just to survive. You once wrote, “tolerating a day job, using money and the periodic vacation as motivation is a bullshit way to live.”

But you’ve never struggled. You’ve been privileged your whole life.

When younger people ask you for advice today, you try not to judge. You try to understand.

If they remain humble and open — something that took you too long to learn — they’ll eventually figure out their own path.

The Business of Life Is the Accumulation of Memories

It’s 2013. Year 7. You’re cruising down the streets of Dhaka with Flo Rida blasting from the Toyota Harrier’s JBL speakers. You’re on your way home after an installation of fiber optic sensors on a gas well. You don’t know it but it’ll be the last field job you’ll ever do.

You’re thankful for music. The memories fade, but the songs always bring you back.

Like the first time you heard Avenged Sevenfold’s “Dear God” as you were finishing a job in Brunei.

Normally things are quiet in the work cabin as the delicate fiber optic work needs concentration. But as the project winds down, the captain loosens up and music plays.

After all these years, the lyrics still get you. It’s perhaps the quasi-loneliness that every traveler knows:

“A lonely road, crossed another cold state line.
Miles away from those I love, purpose undefined.”

Back then, your field work allowed you to quickly see the fruits of your labor. Psychologists say that direct feedback loop is important for work satisfaction. You’re much further away now — half in the boardroom, half working from home in your underwear — it’s hard to feel the impact of your work.

Maybe that’s why you’re restless. Maybe that’s why your mind asks difficult questions.

Were Your Work Friends Really Your Friends?

Are they really your friends if your WhatsApp group only lights up during Christmas and you meet once every two years?

You smile, recalling the slop article you read last week — saying you should NEVER share anything personal at work, and colleagues are not your friends. Well maybe, if you’re a psychopath.

You’ve learned that you can go through life being cynical and risk-averse — protecting yourself from every imagined danger and hurt — but the cost is steep: It won’t be a well-lived life.

Instead, you chose a life where you’d rather risk pain than feel nothing.

The memories continue to flow, but it’s hard to place when exactly everything happened. It’s a collage of faces from different times in your life. It’s all good. You miss your team. Your friends. When you see them, you’ll all have moved to different things in life and grown into different people. Yet if you believe that memories can be alive, that they’re not merely a pleasant mix of brain signals and hormones, you’ll always be connected somehow.

You hope they think of you once in a while.

The Truth About Working for Passion

Does being good at something arouse passion, or does passion make you get better at something? Like many “life” things, it’s a mix of both. A virtuous cycle.

It doesn’t mean you’ll be great though.

It’s 2016. Year 11. You quit your high-flying job to pursue a new career path where you have that direct feedback loop with an audience you love. It’s even for a charitable cause. It’s the perfect job, except you realize you aren’t very good at it. Within two years, you’re out. That’s okay, you loved and lost. You have no regrets.

The concept of Ikigai is true. It is however, idealistic. Progress is more important than absolutes. Nudge yourself in the direction of what you’re good at, what the world needs, what you love, and what makes money.

But don’t forget that as an individual you have worth. You’re not just the sum of titles you’ve held and battles you’ve fought. Yes, you have missions in life — you need to serve. But you also have needs.

The happiest people have balance.

Can You Be a Good Manager Without Being an Asshole?

People management is the hardest thing. But anything worth doing is hard. Easy things get displaced at work. Replaced by the cheaper, more efficient thing.

AI can replace many things, but it won’t replace leadership.

How do you drive higher performance from people whose cost-benefit calculation is lowest amount of work for the same pay? You haven’t figured that one out yet. No amount of bestselling pop management books seem to help.

You blame cynical slop articles aimed at Gen Z. There used to be honor at work — it wasn’t just about doing the bare minimum to get paid. As Andy Sachs says, “I worry about this generation.”

You’ve betrayed and been betrayed.

Okay, in your case you didn’t really betray. You merely made the least-bad decision in difficult circumstances. Warning letters, redundancies, strategy pivots. Tough, but someone had to do it. Ultimately, you’re the hero in your own story. You can’t think of yourself as a villain. It would destroy you.

Nothing Lasts Forever (Except Maybe Love)

You’ve seen fads come and go. In 2015, everyone talked about how video was gonna be the next big thing on Facebook. Well, short-form video did take over the world, but who could have foreseen nobody uses Facebook anymore.

Nothing is certain. Nothing lasts forever. Not your job scope, not your boss, not the president.

You’re thankful you realized a universal truth early. Year 10. You were only 31. With age, you know it to be truer than ever: The most important thing is love. Strong relationships with your family and friends.

Ideally, your work integrates these well. At the bare minimum, your work should support your social wealth. If your work allows your relationships to thrive, that’s priceless.

But because you change and things change, it’s a never-ending question. Every day you wake up and ask yourself if your work serves you anymore. You’re comfortable, but wonder if there’s more to life than this.

It’s Year 21. You’ve been working for 20 years now. It’s 5 minutes till your next meeting.

You boot up Claude and ask, “What’s next?”

– – –

Pic from Pexels: Scott Webb