When Dreams Die

Do you have dreams to become a billionaire? I did. I no longer do, although I might eventually end up one anyway if I live long enough (I’ll explain later). But I no longer hold that dream. And that is a good thing.

In my TED talk, I talked about my dream of becoming Bill Gates from an early age. I constantly read books and news articles about tech entrepreneurs making it big. I visualized taking the company I built from the ground up to IPO, ringing the bell at Nasdaq, being featured on Businessweek (used to be my favorite magazine), owning multiple mansions across the world, and joining Bill Gates’ billionaire philanthropic pledge whiling shaking his hand telling him how much he has inspired me.

Then I once heard Bruno Mars’ song, Billionaire, and viscerally hated it. How dare he stared into my soul and perfectly described my feelings, and mercilessly portrayed a desperate asshole with this beautifully written song?

Listen to this thing!

“That can’t be me,” I thought to myself. I am the cool guy, not the money-chasing douchebag.

So, my mind adjusted my image. It’s not about the money, but the impact I am making on the world. When I die, the world will be a much, much better place. And the billionaire bank account will be a by-product, and I don’t even care (although I deeply cared in reality.)

Then, I ran into this episode of Silicon Valley, in which every wannapreneur claimed that they were revolutionizing the world and making it a better place, no matter what they were making. It once again assaulted my self-image.

“OK, screw all these songs and shows. How dare they so accurately described my feelings,” I thought to myself. I will just focus on building the tech company that will lead me to billionaire status then. Who cares if I’m mocked or not. Maybe one day I’ll fund my own record company and own my own TV show. What’s up?

So that’s all I did for the past 10 years. I quit my job and threw every ounce of energy and creativity I had to build a successful tech company. And I read hundreds of books, listened to thousands of hours of podcasts, ideated and prototyped countless concepts, networked with thousands of people, invested and fundraised hundreds of thousands of dollars, built multiple apps, pitched to numerous clients, attended several conferences, hired and fired plenty of people. In the end, it didn’t work. The money ran out and the people left. And that was that.

I read and tried it all

Statistically speaking, 90% of startups fail. But I was so sure I was no ordinary man, and I would will my way to become the 10%.

Nope, I was the 90%!

Should I have never followed up on my dream and quit my job, and pursued the safe route of a steady job income instead?

Not in a million years!

But here is the interesting part: not only did I not consider my entrepreneurial journey a spectacular failure, but an awesome success. Here are three reasons:

  1. I have no regret… at all. Throughout the process, I gave all I had. In fact, I would have had huge regret by not going through the journey. The people with the most devasting regret are the people who wanted to try something but didn’t do it for various reasons. Maybe they were afraid of failure; Perhaps they didn’t want to look foolish; Or they wanted to live up to others’ expectations rather than their own dreams. When they get old, they will always be tortured by what-could-have-been. You can’t minimize failures in life, but you can indeed minimize regret, which is way more damaging than failures. And when I get old, I will look back at my tech entrepreneur dream in my 30’s as a beautiful journey that led to…
  • A world of unexpected opportunities opened up to me. I started blogging, and it was a wild success. My 100 Days of Rejection blog accumulated over 10M views, which opened the door to a bestselling book, a popular TED talk, and becoming a sought-after speaker. The income coming through all these venues are very satisfying. It wasn’t the F U money that a tech founder would have dreamt, but way more than I could have ever hoped for working for someone else. Now I have expanded my business into personal coaching and used my credibility to launch another blog of my passion – this one. Everything beautiful and exciting started when I first took the step of becoming an entrepreneur.
  • I have developed an entrepreneur’s mindset. Entrepreneurship is not just about the eventual success, but the discipline and thinking that came with it. It’s about fearlessly trying new ideas, measuring data to make decisions, and learning and adapting from failures. It was precisely that mindset that led me to experiment with and develop the Love Investor methodology. In the past 10 years, my investment’s compound annual return of 25% not only made me a multi-millionaire, but also gave me the skills and confidence to launch this blog teaching others how to invest.

Speaking of Love Investing, truth be told, I don’t expect my return to stay at 25% every year. It will probably drop back to around 15% over the long run while still crushing the S&P 500. But even with more realistic expectations, I still have a slight chance to reach that billionaire status through investing, thanks to the art of Love Investing and the miracle of compound interest. No, I won’t be a cool young billionaire, but a grizzly old one.

But money is honestly no longer my dream anymore. When you reach 40, you know you are at the half-time of your earthly life. My wife and I are devoting the second half of our time to things way more important than money: spiritual contribution to our faith, teaching the world about investing and fulfillment, and indeed, making the world a better place.

They say life is a journey, not a destination. It’s indeed a journey influenced by many decisions along the way that would impact the path and the destination. Following my dream to become an entrepreneur was the best career decision I have ever made, even if it didn’t lead to the original definition of success. And if that’s your dream, you should make that decision too.

Now, tell me an example (through comments or reply) where you failed at something you passionately loved, but used the learning to achieve success later.