They say you learn when you’re out of your comfort zone. Well, nothing is more uncomfortable than when you make a mistake. I’ve had my fair share of those. Why do you think I seem to have all the answers?

It was my worst failure, and yet the best thing that ever happened to me.

You can only learn so much in school or in books. Sometimes you just have to make mistakes to really learn important lessons.

Failures and mistakes are the greatest lessons in life. They can make you cringe. They can hurt. And sometimes, they can strip you of any dignity you thought you had. But they are also very humbling.

And the biggest mistakes? You never, ever forget them. The trick, though, is to learn from them.


My worst failure ever was when I quit UCLA after my Freshman year. Part of it was that my mom died on the 2nd day of Freshman Orientation. After that, my first year at this great university was a complete and utter flop — I got As and Fs. I either showed up to class or didn’t. I was 18 and lost. I didn’t know what to do with my life.

When I came back home, I started partying (never did that before), so my dad gave me an ultimatum. He was mowing the lawn and said, “If you want to live under my roof, you follow my rules.” Having no impulse control, I bought a one-way ticket to San Francisco. My next mistake.

Little did I know that in 1997, when I impetuously moved to the Bay Area, the Dot Com Boom was happening. To make ends meet, I started working as an Admin Assistant at a Y2K consulting firm — a tech firm! That was the beginning of my tech career and the beginning of my love for tech.

1. If I hadn’t failed my first year at UCLA

2. My dad wouldn’t have kicked me out

3. I probably wouldn’t have moved to San Francisco

4. When the Dot Com Boom was happening (and it was happening there!)

5. I might have never gotten into tech at all

6. I might have never gotten into any Fortune 500s, which ended up paying for the last year of my Bachelor’s degree.

7. I might have never met a lot of wise people, who taught me to job hop the smart way.

8. I might have never made as much money as I did before.

9. I might have never done a career change into career advice

10. I might have never met you.

It was the WORST failure of my life. Because it took me 6 schools and 10 years to finally get my Bachelor’s degree from CSULB.

But it was also the BEST thing that ever happened to me. Because it landed me in San Francisco in 1997, right when the Dot Com Boom was happening.

How did this happen?

Below is a modified Celebration Grid, which was based on Jurgen Appolo’s Management 3.0 principles, which was in turn, based on Donald Reinertsen’s The Principles of Product Development Flow: Second Generation Lean Product Development. This chart is pretty phenomenal — I revised the text and added some blue graphics, but it really explains the science behind why failures can be successes.

Basically, I made a huge mistake by dropping out of UCLA, but I was LUCKY because it landed me right in the middle of the Dot Com Boom! I experimented with success methods, learned a lot over the years, and refined my practices until it got me to here — to you.

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So never forget this:

When one door closes, more doors open. But they don’t open up by themselves. You have to open it up yourself.

And sometimes, you have to pry them open. Just never, ever give up!

Oh, and if you’d like to follow my exact Fortune 500 path, I’ll be teaching a live online course on breaking into a 6-figure government contracting career on Saturday 8/21/2021. Sign up here or click below. I can’t wait to share all my lessons learned with you. 🙌

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