The Leap, The Flop, The Future

My first bonus day as an insurance man, ended with me doing a belly flop into the bay off pier 23.?

This was 20 years ago, 2003.

12 men, all under the age of 40 met the city for a Friday full of debauchery and celebration.?

It was an electric time in my life. 22, living in a big city, promising career, growing network of friends; every week was an adventure.

While everyone else was cashing big checks that day, I was broke.

I had moved from the mid-west directly after college graduation and landed my first job as sales executive for Unum. “We are right between Nike and Heinz on the fortune 200 list”, I told my family and friends.

I was a rookie, a grunt, barely human. “They” believed in me.

I had spent my relocation budget on 2 new oversized suits from men’s warehouse, a down payment on a leased Audi A4, gas for the cross-country drive, 2 hotel rooms, first month’s rent/deposit, and a bed.?Priorities.

The first month on the job, I slept on the mattress with no sheets and maxed out my credit card surviving.

6 months in, I was granted a territory and the promise of success.? I was all in. I was alive, carefree. Still Broke.

?

After 4 hours of Ketel One & tonics, Corona buckets and little to eat, the energy was palpable.?There were certainly some Jager Bombs too.

There were 300 people on the deck, peak happy hour. ?It was a crisp San Francisco winter day, with the sun peaking through the haze.?

My mentor looked at me with a drink in hand and side smirk on his face.

“I bet you won’t jump into the bay!”

“How much”? I gulped.

?“$1,000”.

“You will pay me cash, today?”

Check.

“If I am arrested, will someone bail me out?”

Check.

“Hold My Phone.” ?It was a Trio Black berry. Slick for a kid.

They cleared a runway, I scaled the wooden fence, attempted to push off, slipped, and frantically fell 25 feet into the bay. Wee, Smack, Oooff.

Immediately when I landed, there were people clapping, cheering, laughing.?

I swam to a ladder 30 feet away, climbed it quickly and disappeared into a warehouse and onto Embarcadero Street.?

A colleague, hysterically laughing, met me on the street, handed me his coat and my phone and said…“That was Awesome”.

We went back into the happy hour, I grabbed a Corona, and was handed my cash.? The night was just beginning.

The next day, I bought a Takamine Guitar and a pair of Diesel jeans. Again, priorities.? Money well spent in my brain.? I still have the guitar.

The money wasn’t the reason I took the leap.? I have never really cared about money.

I wanted to be accepted. To prove something.

The culture in those days, was extreme.

In order to thrive, you had to out hustle, out work, out party and in the process differentiate yourself from 10 other young men that looked just like you.? You did all those things; the money would come.

It did for me, and quickly.

Soon after, my desire to fit into that culture changed drastically. I started to rebel from it, and who I was becoming. ??I didn’t want to wear the uniform anymore or belong to the “boys club”.

?I left. I came back, left again, and came back again. ?

90 percent of the men at that celebration are successful leaders in the industry.

?All unique, good men who I receive mentorship and guidance from on occasion and in various facets of my life.

The Truth is, I have grown up in the industry.? It opened its arms to me. It has caused me to reflect, to challenge myself, to grow and change - to dare to be different.

It’s where I belong, on my terms.

?I realize now more than ever, my importance, my potential impact, my voice and what an amazing opportunity I have been given to open this world to others and to influence the future in a positive way.

?My privilege.?

I’m taking the leap again – I don’t plan on flopping.