Rich people say money doesn’t buy happiness. Beautiful people say looks don’t matter. Smart people say talent is overrated.

One reason: People often underestimate the privilege they hold. It’s easy to downplay something when you don’t realize it helped make you.

Another angle: You get used to things. The first time you stayed at a Ritz-Carlton, your mind was blown. The second time, you got annoyed the room was too cold, and wondered how to upgrade to Club Level. Your expectations change, as does your perception of what “normal” means.

The scientific term for this is hedonic adaptation. It’s useful for evolution, but also creates challenges.

A couple of thoughts around levelling up, but not getting blindsided by its downsides:

Be Careful of What “Life Stage” Advice You Take

When seeking advice from people who’ve made it, don’t ask what they do today.

It’s a fun question, but not useful if you’re in vastly different stages of life. Also, they might have forgotten what it’s like to struggle — especially if they’ve been successful for a long time.

Instead, ask what they did when they were once in your position. Or what they’d do today if they had to start from zero.

To Not Forget Where You Came From — Write Things Down

Keep a record so you can look back and evaluate your life.

Many angles to consider, but I find the money lens fascinating: How did you behave when you were earning $x? How do you behave now that you’ve surpassed $y?

I’ve been keeping spreadsheets of personal budgets since I started work. Over time, I’ve realized a budget isn’t just useful to plan my spending for the month. It’s also useful to reflect about what kind of person I was 15 years ago.

To predict your future, reflect on your past.

To Stay Happy, Fight Ever-Increasing Expectations

When it comes to improving your quality of life, I like the idea of enjoying, but not expecting. You can appreciate a Michelin Star Omakase, while not taking a simple sandwich for granted.

It’s hard — goes against human nature. You have to work at it.

But I’m convinced that practicing gratitude for the simple things is how to keep your expectations reasonable. And stay happy.

Don’t Punish Your Present by Overinvesting in the Future

I love listening to timeless wisdom from older people. Even more as I’ve gotten older. So much that I wonder if I’m developing blind spots:

If all you do is take advice from 94-year-old billionaires, is there risk of spoiling the fun of your youth?

Young Money creator Jack Raines writes about how you can’t backpack in hostels when you’re 35 years old. (Of course you can, but it’s weird.) There’s a time and season for everything. There are silly things you did 10 years ago which you can’t do now. Doesn’t mean you should do it today — but you were probably right to stay up all night and deal with that hangover when you were 22.

There’s wisdom in finding balance between short-term side quests and long-term destinations.

It also reminds me about the debate around FIRE (Financial Independence, Retire Early). I understand the need for conscious spending and discipline. But if taken to the extreme — depriving yourself of a good life today for “retirement” >10 years away feels silly.

Save for retirement, but go out this weekend. You can do both.

Earn Some Privileges (But Harvest Your Gifts)

An interesting life hack for men: it’s pretty easy for the average guy to boost his position on the physical attraction scale. Get a good haircut, put effort into grooming and dressing well, invest time at the gym, and you’ll be ahead of many others.

This is harder for women — because on average, women spend more (time and money) on grooming than men.

What advantages do rich/beautiful/talented people have that you could also get, with some work?

Okay, maybe you think I’m an idiot for talking about looks. What about using AI tools to augment your abilities? So you’re smarter, wiser and more efficient.

The reverse angle is also interesting. What comes so naturally to you that you don’t even think about it?

I recently saw a unique take on Twitter (which I unfortunately can’t find¹ anymore) — sharing how to figure out where your unique strengths and natural talents would shine:

“In what field do you feel the majority of people have bad taste?”

How To Make Growth Less Scary

Growth is scary. Change is scary.

Playing with perspective can help.

Reflecting on the past: think about how you’ve levelled up before — whether it was learning to swim, or giving your first public presentation. It was hard at first, but eventually you got used to it. You just forgot how hard it was.

Zooming into the future: Sometimes we fear how difficult something important will be. So it might take five years. But five years is gonna pass anyway — might as well do it.

“Stop worrying about how long it will take and get started. Time will pass either way.”

– James Clear –

Pull People up the Ladder Behind You

Harvard professor Arthur C. Brooks once wrote a thought-provoking article called “Your Professional Decline Is Coming (Much) Sooner Than You Think“

Everyone gets old. Your abilities fade and you eventually lose your edge.

What should a high achiever do? Strive harder to maintain your position as king of the hill? Professor Brooks has a different take:

“The biggest mistake professionally successful people make is attempting to sustain peak accomplishment indefinitely.”

Instead, you can find fulfilment in later stages of life — not by looking ahead for more and more mountains to conquer — but by looking behind to help others: teaching and mentoring the next generation.

This goes beyond work. When you’ve made it, don’t forget the people behind you.

– – –

Footnotes:

1. Closest I could find was this one from Shaan Puri — quoting Ben Kuhn of Anthropic.

Pic from Pexels: Stefan Stefancik