Chapter 1: A Journey Through Time

Recently, I found myself speaking to a group of aspiring entrepreneurs at a local university. As I recounted my journey in the world of startups, I revealed that I had embarked on my first venture at the age of 20. Now that I've reached 40, it struck me that I've been engaged in building companies for longer than I haven't.

"Wow," I remarked, somewhat surprised, "I've been at this for more than half my life. When did I get so old?"

The audience chuckled, and I continued with my presentation, momentarily forgetting this epiphany. However, the following day, I received an email from a participant. She expressed her gratitude for my talk and posed a thought-provoking question:

"If you could hop into a time machine and revisit your very first day as an entrepreneur, what advice would you share with your younger self?"

Admittedly, I took nearly two weeks to respond, not for lack of trying. I crafted numerous replies, each one failing to resonate because the question was more complex than I anticipated.

In one attempt, I emphasized the importance of teamwork. In another, I suggested not taking life too seriously. A third draft included some overused advice about savoring the journey. Yet, everything I wrote felt cliché, and I realized that the question required deeper reflection.

Eventually, I stumbled upon a piece of wisdom that I believe my 20-year-old self would find valuable. I felt a sense of pride in articulating it until I recalled that time travel isn't possible. Nevertheless, I decided to share my insights with all of you instead.

Here's a letter I would pen to my younger self, just as I embarked on my entrepreneurial path. I hope these words resonate with you as much as they would have with me back then.

Dear Aaron,

Greetings from your future self, 20 years down the line! Congratulations... your hair is still intact!

However, you've ventured down a path that diverges from a conventional career, and I want to caution you about this, as it may lead to years of feeling like a failure. Trust me, you're not a failure, but here's why you might feel that way.

Your journey will begin as your friends graduate and secure "real jobs." Unlike them, you won't follow the traditional route, and this will instill a sense of inadequacy within you.

You’ll watch your peers earn steady paychecks and gradually ascend the corporate hierarchy while you hustle through various clients and a series of random gigs. As you observe their progress, it may seem like your life is off course, leading you to believe that everyone else is thriving while you struggle.

But don't fret! You're not on the "wrong" path; you're becoming an entrepreneur.

At this moment, that term might not hold much significance for you. In fact, it will take another 15 years for you to even refer to yourself as an entrepreneur—merely a convenient label for someone who has chosen an unconventional career trajectory. It signifies that, rather than clocking in for a 9-to-5 job, you are embarking on the journey of building your own businesses.

Before you get too carried away with dreams of striking it rich, I must warn you: the path of entrepreneurship will still leave you feeling like a failure.

Many of your ventures will not succeed. Even those that do may not feel like triumphs, as you will always find comparisons to other entrepreneurs who appear to have achieved more, making you feel disheartened.

Do you see the recurring theme? Regardless of your endeavors, you'll constantly compare yourself to others who seem to be thriving, which will cultivate a sense of perpetual failure.

And let’s be clear—you will experience failures. But that’s perfectly fine! Just because many of your attempts will falter does not define you as a failure. Each setback is an opportunity for learning, and learning often involves failure.

The moment you grasp that failure is a part of learning is when you'll truly start to appreciate life.

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Chapter 2: Embracing the Entrepreneurial Spirit