5 Brutally Honest TRUTHS That Gave me an Unfair Advantage in My 20s

Your 20s aren't what you think they are.

And there are five ways you might be ruining them.

This is because what society says matters in your 20s has almost nothing to do with what actually leads to long-term success. I know this because I went from homeless to MIT grad to multi-millionaire entrepreneur and have now been the CEO, board member, investor at tech companies that created billions of dollars in value. But if I could go back and give myself advice on how to find wealth and success a lot faster, these are the five mistakes I would tell myself to avoid.

The single biggest mistake I made in my 20s was not taking the shortcut. I learned this lesson the hard way. When I came out of Boston with a master's degree in math, I had no mentors, nobody to guide me or show me the next career move.

So, stupidly enough, I just accepted the first job that came my way, which paid me about $30,000 or $33,000 a year.

But if someone had told me, "Hey, take your skills to a hedge fund in New York.

They'll pay you 8 to 10 times more," my entire trajectory would have been different.

Of course, eventually things worked out totally fine. But I can literally look back at a chart of my life and it was flat until I found the right mentors and then suddenly everything took off. Within a decade of having some great CEOs as my coaches and guides, I was able to step up and become a CEO myself. And it's not just me.

The data backs it up. Only about 37% of employees have a mentor, but those who do are five times more likely to get promoted.

So, you can do the math, right?

If you don't have a mentor, you're putting yourself at a 500% disadvantage in your career.

Why would you want to do that? Same thing for entrepreneurs and founders as well.

Steve Jobs, Jeff Bezos, Google's founders, they all had Bill Campbell as their mentor who was known as the trillion dollar coach. And my personal favorite, Oprah had Maya Angelo as her mentor.

Oprah used to say Maya was the mother she needed and the friend everyone deserves.

She reshaped Oprah's entire world view with four simple words.

Baby, you're enough.

And when Oprah heard that, she was confused and she asked enough of what? And Maya said, "You don't need another person, place, or thing to make you whole." God already did that.

Your job is to know it.

I think it's such a powerful message.

Mentors are the shortcut to growth, success, clarity.

They don't just give you answers.

They hold up a mirror.

A mirror that shows you not just who you are, but who you can become.

Mentors are like time machines collapsing years of painful trial and error into a direct path forward.

So please don't wait as long as I did to get one. Look for them everywhere, anywhere.

Your temple, your church, your community, extended family, job fairs, alumni, neighborhood, it doesn't matter.

Even if you find someone who's just a few steps ahead of you, that's okay.

Just ask them, "If you were me right now, what would you do differently?

" That single question has the power to save you years of wasted trial and error. Take the shortcut now.

You won't regret it. Mistake number two is choosing the dead end road.

There is one piece of advice that everybody repeats.

Celebrities, billionaires, motivational speakers, and I am here to tell you it's absolutely nonsense.

In my 20s, I was a trained musician.

I traveled the world and performed concerts and practiced for hours and hours every day. You know, music was obviously my passion. But here's the truth.

The more I tried to monetize it, the less I loved it. It stopped being joy.

It became a chore, a stress.

I used to have panic attacks wondering if I was good enough, if someone was better, or will I survive as a musician.

I wasted years trying to make it work.

I practiced a lot. I took all the gigs.

I taught music side hustles. Even my first startup was in music. But every time I forced my passion into paycheck, it failed me.

And I eventually realized finding your passion is not enough.

You have to find something that you can be so good at that you can make a career out of it. And I'm not the only one.

Look at the numbers. More than 80% of artists, actors, and musicians earn less than $22,000 a year. That's what passion pays.

Psychologist Paul O'Keeffe found in his 2018 study that people who treat passion as their career goal give up faster when things get harder.

On the other hand, people who build skills first tend to develop passion for what they become good at and they stick with it longer.

Cal Newport wrote the best book on this idea. so good they can't ignore you.

Most people who say they found their passion only discovered it after years of skill building.

Even Steve Jobs, the guy who made follow your passion famous in his Stanford speech, didn't know what his passion was in his 20s.

He dropped out of college, quit jobs, went to India searching for meaning of life. His so-called passion only became clear much later.

after building skills, after succeeding as sales rep, after Apple, after Pixar, Steve Jobs in his 20s did not follow the advice of Steve Jobs in his 40s.

So don't waste your 20s waiting for that passion lottery ticket to pay off.

Build math skills first. Be so good they can't ignore you.

Or as Mark Cuban says, don't follow your passion, follow your effort.

Because effort reveals what you actually care enough to suffer for. I love that quote.

That brings me to mistake number three, the impatience tax. If I had to put a dollar figure on this mistake, it probably cost me tens of millions over my lifetime.

And the worst part, I made it in my 20s when it was easier to avoid.

In my 20s, I thought the stock market was just gambling. So, I didn't invest.

I waited too long before I put money in the market. And that was mistake number one. Mistake number two was even worse. In 2008, during the financial crisis, our portfolio dropped 30%.

I panicked, pulled everything out and stayed out of the market.

When the market came roaring back, I was still sitting by the side. That single move cost me about 40% of my long-term net worth.

Eventually, I learned the hard way.

You cannot time the market, and the data proves it. JP Morgan found that if you miss just the 10 best trading days in 20 years, your returns are cut in half.

And if you miss the best 30 days, you're almost at zero. You'll miss 90% of your upside. So, how do you know which 10 days are those 10 days?

Well, you can't know that. And a Fidelity study actually found something even more interesting.

The best performing accounts are the ones people forgot about by mistake.

Ironically, that's exactly what happened to me. One of my best investments was a retirement account I forgot even existed. One of my old companies 401k from one of those very early days wasn't a big number then, but because I didn't touch it, compounding did the work for me.

That's the psychology of money.

Fear and impatience kills wealth.

As Warren Buffett said, the stock market is designed to transfer money from the active to the patient.

And compounding only works if you give it time.

If you invest $100 every month, starting at 20, you will have over $1 million by 65.

You start at 30, you'll end up with less than half.

That 10-year delay costs you about $700,000.

That is the time value of money.

So, what's my genius investment banker MBA MIT financial advice? I think it's pretty silly and stupid and simple.

First, invest early, stay consistent, and don't touch it. Don't try to time the market.

Second, stay in the game, and let compounding do its job.

And above all, don't save what's left after spending.

Spend what's left after saving.

Mistake number four is falling into the safety trap. In your 20s, the riskiest move you can make isn't quitting your job or moving to a new city.

The riskiest move is staying exactly where you are. I learned this lesson in two ways. First, when I decided to stay in Boston for 16 years after graduating, it was safe.

It was comfortable, familiar. There were lots of great startups coming out of MIT and Harvard and other schools, but everybody knew then what we know now, the real explosion of opportunities at least in tech and AI was happening in Silicon Valley in San Francisco. And I wanted to be a part of that. As a matter of fact, I moved to San Francisco for a year, but then I decided to come back because my fiance at that time, my wife now had ended up matching at Harvard Medical School.

But when I look back, I also realized that I had many, many opportunities after that to move to the West Coast, but I don't think I had the courage to make the move and make that big gamble.

And I still to this day regret it.

The second way I learned this lesson was when I stayed too long under a toxic boss. He undermined me constantly at every juncture.

But instead of leaving, I stuck it out.

I wasted 18 months feeling completely trapped and it literally slowly drained every ounce of joy and confidence out of me.

That's what risk avoidance does.

It's like carbon monoxide.

You don't notice it at first, but it will kill your growth if you stay with it for too long.

And the data backs this up.

Urban economics research shows that people who move to opportunity hubs like San Francisco or New York or London or Mumbai or Bangalore, they see their lifetime earnings grow significantly faster than those who stay in smaller markets.

Would Elon Musk be this successful if he had never left South Africa?

What if Satya Nadella had never left India and decided to work in some random IT services firm as one of their engineers?

Both Elon and Satya wouldn't be where they are today if they hadn't taken huge risks and they were doing that even today even after becoming successful.

They keep taking risks.

That's why they and their companies keep on growing.

So don't confuse stability with safety.

If your boss, your city, your environment is draining you, move.

You're not a tree, you can move.

Ask yourself, am I growing here or just standing still.

If it's the ladder, take the risk.

Go where the opportunities are.

Especially in your 20s when you have more freedom and virtually nothing to lose.

This brings me to mistake number five.

We've talked about the safety trap, but there is another trap that's even harder to see. I call it the invisible cage.

Because the toughest prison to escape in your 20s is not your job, your city, or even your finances.

It's the one you build inside your own head.

You know, in my 20s, I thought I wasn't talented.

I was shy. I had no presence.

Yeah. Hard to believe.

I thought I was ugly. Was too skinny.

And later, years later, I realized that those weren't even my thoughts.

They weren't my words. They were my father's.

Here's the thing. When you're young, sometimes you build your entire identity out of labels someone else puts on you.

That's exactly what I did. I was in my own emotional prison. My identity was formed by those labels. It took years of reflection and journaling and self- therapy and struggle to even begin to break out of it. And even today, I wonder if I'm completely out.

I still fight self-doubt, loneliness, and I crave for attention.

Some wounds take a long time to heal. And today I have some different set of labels.

MIT this, CEO that investor blah musician blah board member blah whatever but there are still labels deep down do I feel I have any intrinsic worth without any of those labels that's the question I always ask myself and I know I'm not alone the American Psychological Association found that 70% of 18 to 29 year olds frequently doubt themselves and their future 70% and The Journal of Behavioral Science says 82% of people experience imposttor syndrome in their careers.

8 out of 10. So if you feel stuck or feel like you don't belong, that's how all of us feel.

We all struggle with selfworth whether we admit it or not. The danger is when shame hardens around those doubts.

Shame is like a scar tissue. You know, it protects you, but it also numbs you and blocks you from growing, from feeling, from connecting, from being vulnerable.

So, if you're in your 20s, ask yourself, are the labels in your head really yours?

Or were they handed to you by someone else?

Journal about them, challenge them, shed that skin, even if it takes time, and don't be ashamed of who you are while you are in that process, right?

Because no external success, no degree, no job title, no bank balance will ever fill that gap inside you.

Only self-compassion and self-love will do that.

So accept yourself now as you are, not someday in the future, not based on some conditions.

Because sooner you do that, the freer you will be to live the life that feels truly yours. As Maya Angelo said, "Baby, you're enough." If you like this video, please don't forget to subscribe.

And if you want to start building the skills to get ahead in your 20s, check out my video on why you working hard and still falling behind.

I'll see you there. Thank you and I love