Life after “Golden Handcuffs”

golden handcuffs

Leaving Wall Street cost me $900,000.

Yup, the “Golden Handcuffs” are real. Bonuses are deferred.

So by definition you leave money on the table.

At 35, I said f** it.

I want to own my time, surf every day & watch my kids grow up.

8 years later, I’m still standing.

I’ve learned a lot about myself, my relationship to money and what it means to lead a fulfilling life. So whether you’re stuck in your cubicle, dreaming of a start-up or wondering “Is this it?” – here are 8 lessons that can act as a roadmap for the path less traveled.

1. Do you want to own the successful version of career?

A big motivation to leave Wall Street was looking at peers who were 15 years older than me.

They had a great life – second homes, cars, fancy vacations – but it wasn’t for me.

Not only did many looked haggard, drank a lot and had dicey relationships with their spouses and kids. They were still prisoners to email, meetings and the need to be “always on.”

Funny enough, it’s possible to trade one hamster wheel for another.

In the game of online business, you can quickly replicate the need to always be creating, maximizing and optimizing.

As I dipped into the world of online courses (and got a taste of success) I was reminded of the question:

“Do I want to own the successful version of this business?”

It turns out the answer was no.

2. The “Magic Window” is real

I’ve never had a 9-to-5 job as a dad.

In fact, the first time my daughter saw me in a suit, she asked:

“Why are you dressed like Barak Obama.”

That same daughter is now 9. And she went from calling me dad – to calling me “bruh.”

She still loves me, but anytime I propose an activity with her she’ll immediately ask “Can my friend come?”

I’m so grateful that I got to be there for the bath times, bedtime stories, camping trips and snuggles.

And excited for the next Magic Window to reveal itself.

3. I’ll take Tiny Moments over Bucket Lists

Bucket lists are BS.

Yes, I’ve sat court-side for the Knicks, skied a private mountain (The Yellowstone Club) and attended the Super Bowl. All for free.

But having spent so much time at home with my family and on my own terms – I’ve learned that it’s the Tiny Moments that matter.

My daughter describing her dream to me in vivid detail.

An unscheduled call with an old friends.

A perfectly cooked piece of bacon.

Waxing my surfboard.

(And of course, the non-glucose-spiking Skinny Margarita.)

It’s become clear to me that a happy and fulfilled life is stringing together – and being present – for as many of these Tiny Moments as possible.

4. Showing up is 98% of the game

I suck at going viral.

I’ve barely gotten any press.

My IG game is weak AF.

But one thing I’m good at is showing up. It’s my slow grind strategy, where you see most of your peers (I don’t view them as competitors) drop out.

Some of my streaks:

  • Snapchat stories: 180 consecutive days
  • Podcast: 52 weekly episodes
  • Video Shorts: 180 days
  • Blogging: 200 consecutive weeks
  • Newsletter: 391 weeks

If you put yourself out there on a regular basis, while adding value (and understanding your customers’ needs) – good stuff will happen.

Just by staying in the game.

5. I never want to specialize

Do you like your coffee to taste the same every morning?

Or is variety the spice of life?

The best part about entrepreneurship (especially, the creative kind) is that every day is different.

In hindsight, it’s why I couldn’t stay on Wall Street. It’s probably why I’ll never have a 9-to-5 again.

In business, this can be problematic.

Many gurus will insist that you “niche down.” After all, you don’t want your customers to be subject to the whims of your interests and desires.

I’ll never be able to do that.

For me creative expression will always be authentic and from the heart.

This will make for a windy road. But it’s the only road that I’m willing to take.

6. You’ll always worry about money

Money is a strange thing.

I walked away from a very high W-2 income with a lot of savings. (I also benefited from a massive run-up in stocks since 2015.)

Nothing can prepare you for the absence of a bi-monthly paycheck.

And the ensuing volatility of your net worth.

What’s crazy is that when things were going well, I worried about money. And wanted more.

When things were bumpy, I worried about money too.

Which leads to a crazy conclusion:

Worrying about money is INDEPENDENT of the money in your bank account (once your basic needs are covered.)

And having coached folks with $50 mm+ in net worth, I can confirm this is true.

7. AND it’s also easy to make money

The Lindy effect says that the longer an idea or technology has been around, the longer it continues to be useful.

And while I’m no crypto freak, Bitcoin is Lindy. Its durability continues to validate its existence.

The same applies to entrepreneurship.

If you show up, add value, act like a decent human and have half a brain – opportunities will find you.

This has happened to me via coaching, sponsors, speaking and online courses. Pretty much every source of monetization.

And even though we’re experiencing a bumpy part in our biz, opportunities continue to show up.

The harder part is finding money-making opportunities that align with your values.

If you’re crystal clear about who you work with, under what conditions and on the type of projects you will agree to work on – the opportunity set may contract.

8. Knowing your “Enough” makes it all fall into place

On my 8 year anniversary I often look at my peers who stayed.

I joked, “Man, even the mediocre ones have tripled their net worth over that period.”

I look in my town and see people building brand new houses.

Others are surfing Kelly Slater’s private wave (priced at $7,500 for a couple hours).

And some are taking their families to the Amangiri.

I say to myself, “Man it would be nice to do those things without worrying about money.”

But we have enough.

Our home is enough.

Our beat up Acura, enough.

Kids’ college, enough.

Retirement, enough.

(Especially since I plan on doing this well beyond 60).

Seneca said, “It is not the man who has too little, but the man who craves more, that is poor.”

Landing on enough has opened up a beautiful life.

One rich with possibility.

PS If you enjoyed reading this, you’ll enjoy 43 Life Lessons at 43 Years Old.

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