update #2: It's my birthday and a reflection on the last ten years

I  just turned 32.

It was ten years ago I had just graduated from college.

A lot has happened between then and now.

• I moved to Austin, TX, to work on another startup.
• There, I made lifelong friends, one of whom I married.
• I moved to Seattle, so my wife could become a therapist.
• I saved a lot of money; some years, I saved 70%+ of my income.
• I made 5,000% on some investments I made.
• I lost $70k in one year.
• I was laid off from my job last year, which was the best thing that could have happened to me.

Why? 

I was unhappy at my job. I knew I wanted to do something on my own. I had the resources, the experience, and the disposition to create something, but I was stuck. What was stopping me?

To answer this, I need to go back 20+ years to when I was a kid in school.

I struggled a lot in school.  Everything was hard for me. I couldn’t read, write, or color inside the lines. I felt really stupid. I would spend hours on homework, see my classmates' homework, and throw mine in the trash because I was so embarrassed. I’d rather get zero than for my teacher to see how bad it was.

I was eventually diagnosed with dyslexia.

I had to work my ass off to get Cs. 

Eventually, I learned how to , launched a product for thousands of businesses, and started to care about my salary, title, and influence in the organization. That’s and write. After a few more years of hard work, I got better grades. I got 5 on my first and only AP test. I got into college and even graduated Magna Cum Laude. It wasn’t Standford, but I didn’t think I’d attend college.

After several failed startups, I got a job at a big tech company. I doubled my salary in a year, launched a product for thousands of businesses, and started to care about my salary, title, and influence in the organization. That’s when things started going downhill.

I stopped building because I wanted to make something; I joined teams because I thought it would benefit my career. I was a career man now. My dreams of blazing my own path were a distant memory. That part of me that felt like an outsider was lost after I tasted the drug of a regular, growing paycheck and positive manager reviews. I was working for other people, not myself.

Then I got laid off.

At first, I was excited. I traveled a bit. Started thinking about what I’d work on. I even started selling this ultralight-down dog sleeping bag.

Then I started to feel depressed; I even started looking for a job. I didn’t need a job, but I thought, “What the hell am I doing with my life?”

It took a few months, and being a part of this 11-week program in San Francisco called buildspace, I realized I needed the affirmation I got from a paycheck and a manager's approval. I cared more about the number in my bank account than following my dreams.

I said, fuck that. It might have served me most of those ten years, but it wasn’t for me anymore.

What is different now? 

• I have 35 friends doing the same thing and understand the struggle to trust yourself.
• I’m enjoying the journey more than the destination.
• I’m following my excitement and trusting my intuition.

The funny thing is that while my bank account number is decreasing, some of my investments are increasing a lot. The value of those investments grew more in the last nine months than I made in salary the year prior at my job. Crazy!

Life is funny that way.

Someone wise told me: “I try to live my life as if I don’t know what will happen because the truth is you don’t know what's going to happen.”

I’m living the next ten years like I don’t know what will happen. 

The only certainty in life is uncertainty…and death.

I’m going to try to remember that last part.