What I Wish I Knew In My 20s

Success Ahead

My twenties were arguably the best decade of my life.

As most young people tend to be, I was full of energy, optimism, and ambition.

I also had a solid job with a fantastic work-life balance, which left enough time to lift weights, have fun with my friends, and even try my hand at entrepreneurship.

Most importantly, I was dating a beautiful girl, who subsequently became my wife and the mother of my children.

In other words, my life was nearly complete.  Nearly – because one thing was missing.


Now, I had a pretty clear view of how I wanted to design my life.  I wanted to travel the world, have a successful career, start a family – and hopefully get rich along the way.

The problem was, I just didn’t know anyone who could guide me on that journey.

Over the years, I (kind of) figured things out.  Mostly through trial and error, a willingness to give different things ago, as well as a healthy dose of luck.

That being said, here are some things I sure wish I knew when I was starting out twenty years ago.

On Building A Successful Career

Choosing a big, fast-growing industry is critical to your career success.

It doesn’t matter how good you are at your job.  You can be a math savant, a salesperson extraordinaire, or the most talented engineer in the world.

But regardless of your ability, swimming against the current is NEVER a good idea.

To give you a pointed example: over the past ten years, the average performers at Amazon have ended up light years ahead of some of the most talented employees at American Airlines.

Simply because they chose to swim downstream, not upstream.

Take your cue – because there’s something magical about combining a healthy dose of talent with the wind in your sails.

In other words, identify the trend – and make it your friend.  You won’t regret it.

It’s critical to get a solid brand on your CV early on in your career.

Like it or not, but getting a role with a large, established, blue-chip company is an automatic stamp of approval.

If nothing else, it proves that you were able to successfully navigate a competitive and rigorous selection process.

Now, you don’t have to spend more than a couple of years in that role.  But when you do exit, the aura of having been good enough to make the cut at McKinsey or Goldman will open more doors than you could ever imagine.

People will try to convince you of the merits of working in a small, nimble environment.  Of the difference you can make when you are not a part of a big corporate machine.  Of the value of taking a different path.

In fact, the better you are, and the more they want you to join their business, the harder they will work to persuade you of all these things.

I don’t dispute any of those arguments.  But only after you’ve got the right brand on your CV.

Confidence and energy will always trump ability.

There are millions of talented, highly qualified individuals toiling in dead-end jobs.

The problem is that either they don’t really believe in themselves – or don’t put the right level of energy behind their efforts.

At the same time, there are millions of folks with average (or worse) talent – yet brimming with confidence and boundless energy.

They are the ones who keep promoting themselves, who keep giving things a go, who find champions – and who ultimately end up miles ahead of their far more capable peers.

On Getting Rich

If you want to get rich you need to follow the money.

What that means in practice is putting yourself as close as humanly possible to the revenue-generating “engine” of the business you work for.

In an investment bank, that means an M&A advisory or a sales & trading role.

In a consumer packaged goods company, marketing is an important nexus.

And in a technology firm, product design/development is usually a good bet.

Whatever it is, you need to be able to influence the amount of cash coming in through the front door.  It is the absolute best way to make the big bucks.

It’s all about skin in the game.  The one fundamental rule of building wealth is that that if you want to get rich, you NEED to own assets.  

Whether it’s the stock market, real estate, private equity, crypto, digital media, company equity, stock options – look for all and any ways possible to accumulate as many assets as possible, as early as possible.

If you can, amplify your holdings with responsible leverage – and then let your investments ride for as long as you can.  At least a decade – but ideally a couple.

It will feel scary.

Most of the time, you will feel like you are buying assets at the top.

But over time, owning those very assets will feel like being on a magical carpet journey to wealth.

There’s always a bear case.  In your life, you are guaranteed to come across many smart, articulate people who will give you highly compelling reasons not to invest.

High valuations. Geopolitical uncertainty.  Technological disruption.  Interest rates.

Show me an investment and I will give you fifty great reasons not to buy it.  It’s like walking around with a hammer looking for nails.

What you’ve got to remember is that pessimists will ALWAYS sound smarter.  But optimists will ALWAYS get richer.

On Life

You will never have as much energy as you do in your 20s.  Like it or not, but it’s a biological act.

Don’t waste it.

Cherish the mornings when you leap out of bed, ready to take on the world – despite having gone to sleep 3 hours earlier.

Relish the ability to pull off an 80-hour week, and cap it off with a wild night out.

You won’t always feel that way.

And on the same somber note:

Your health will go quicker than you think.

Yes, apparently Tom Brady is performing better in his 40s than in his 20s.

Well, you are not Tom Brady.  Neither am I.

“Health is wealth” is one of the most cliché metaphors out there.  It’s also deadly accurate.

Exit quickly.  Whether it’s a bad job, or a bad relationship, a bad friendship, or any other bad experience, don’t ever wait to pull the ripcord.

There are many things in life that start well and end badly.

But if things are bad to begin with, they almost never end up well.

And most importantly:

A unit of leisure is worth far more when you are young than when you are old(er).

I don’t remember who said it, but this is one of the most astute observations I’ve ever heard.

A cheap, fun-filled beach holiday with your best friends at 22 will knock the socks off having an entire tropical island to yourself when you are 70 – not least because it will also give you a lifetime of memories to enjoy.

If you are in your 20s and reading this, you’ve already got the most amazing gift life can offer.

It’s up to you to make the most of it.

About Banker On Fire

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Banker On FIRE is an M&A (mergers and acquisitions) investment banker. I am passionate about capital markets, behavioural economics, financial independence, and living the best life possible.

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9 thoughts on “What I Wish I Knew In My 20s”

    1. No regrets, but hopefully a younger person (including my kids, someday) reads this and learns something in one blog post that I’ve learned over 10+ years

  1. I agree with most of this.

    To build capital, it’s good to choose a career that’ll maximize it with the least amount of effort. And when in that career, if you need to play politics to maximize the profits there, then it might be prudent to do so.

    The main thing I don’t agree with is that “I have the most energy in my 20s.”

    I say, it depends. I was less healthy in my early 20s than my late 20s. And as of late (I’m in my 30s) I feel way more energetic than my 20s. In my 20s, I do 12-16 hour school days and I’m chronically exhausted.

    Nowadays, I do ~16-hour days on my own projects and I basically have to force myself to sleep.

    1. Fair enough

      I am lucky enough in that I’ve always been quite healthy and fit. And against that baseline, I certainly feel my energy levels have dropped off quite a bit vs my 20s.

      I still do 80-hour weeks at times, but you certainly won’t find me in a club or a bar at the end of one of those!

  2. “Confidence and energy will always trump ability.”

    I found this to be so true for myself personally, but also in employees. Right out of college, my boss would say something like “We need someone to do XYZ” and I would say “I can do it!” – In reality, I had no idea how, but I went and figured it out. That confidence and energy to take it on is what ultimately propelled my career and helped me to land ownership of assets in companies that I was not the founder of.

    1. Fake it till you make it.

      Reminds me of Andre Agassi’s autobiography too. He mentions a coach who made him watch how he walked (head high, shoulders back) when he was playing winning matches. He then made Agassi replicate the same walk in every match, even when he was losing, which apparently massively upped his game and winning %.

    1. Sorry to break it to you!

      The good news is that you get MUCH better at managing your energy levels and also much, much more productive.

      It doesn’t net out but makes a big difference.

      Enjoy your 20s while they last!

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