The Courage to Leave Money on the Table (And Why I'd Do It Again)

I was on the phone with my coach. He'd been listening to me talk about this burning desire I felt for months.

"I'm going to hold," he said. "You're going to call the CEO of Health Central right now or else we're done."

I was terrified. My wife and I had just had our first son a month earlier. I was the sole provider. And I was six months into a one-year retention bonus package (literal guaranteed money just for showing up every day).

So I clicked over, put my coach on hold, and dialed Chris Schroeder.

"Hey Chris, I found out what I'm here on earth to do and I got to go do it. I'm going to become a coach. So I'm stepping down from my role here."

Everyone thought I was crazy. Logically, I should've just made the money and chosen financial safety over this big leap. Just six more months.

But I realized something: I'd been making that same choice of status and money over purpose my entire life.

The Pattern I Couldn't Ignore

Life is a series of extenuating circumstances. There's always something: "I can't right now because we're launching next month." "I can't right now because we're raising a round." "I can't right now because the team is understaffed."

It never feels like the right time.

What happens after "just six more months"? You make that same choice again. And again. Six more months of choosing status and financial safety over purpose.

I'd enrolled in the first weekend of the Coaches Training Institute program. I walked in and immediately knew: these are my people. This is what I'm here to do.

So there I was, six months into working for the company that acquired us, making decent money, with a retention bonus waiting if I just stuck it out.

Every single day I'd think: I know what I'm here to do, but I'm so scared. Will this coaching thing actually work? Will I be able to provide for my family?

What Happened After I Took the Leap

I quit in July or August of 2009. Started putting out the word that I was going through coaches training.

For the first year, I didn't want anything to do with business or making money. I just wanted to be of service to people and feel that sense of fulfillment.

I had this little office downstairs in my apartment (basically the laundry room that I turned into an office). My wife's friends would come over and I'd make them cry. It was such an exciting, heartwarming time. But also really scary. I was charging very little, making very little money, eating into our savings.

God bless my wife. She just believed in me. She believed that if I'm following my authentic purpose, things will work out. And if we have a more modest life but I'm happy and present, that's fine.

From Laundry Room Office to Living the Dream

About a year in, I started coaching entrepreneurs. One was Nir Eyal, who was running Ad Nectar at the time. He told two friends, and they told two friends. Word started spreading through the Stanford network.

I didn't set out to make it a business focused on entrepreneurs. But I realized my background having been through it was really relevant. And working with founders who were building something meaningful felt totally aligned.

So I kept following that, being in flow and my zone of genius. And I just kept getting better at the work because I genuinely loved it. Not because I was fiercely competitive or trying to be the best coach. I just love learning about how to help human beings thrive.

When you love something that much, you naturally keep getting better at it. That leads to mastery, and mastery leads to abundance.

Why I Couldn't Wait (And Why You Might Not Be Able to Either)

Looking back, two things pushed me to finally make that call.

1. My soul was dying. It was such a burning desire at that point. I don't know if I could deal with one more day of doing work that wasn't aligned and on purpose when I now knew what was.

If you're sitting on a similar decision right now, check: Is your soul dying or just uncomfortable? There's a difference between "this is hard and scary" versus "I can't do one more day of this work that isn't aligned with who I am."

2. I needed to be the example I wanted to set. I imagined my future self talking to clients in this predicament and realized: I need to be the change I want to see in the world.

I need to live the way I'm going to coach. I need to be courageous and take the leap so that I can tell this story. And I thought about my son, who do I want to be as a role model for him? What model do I want to set for him of pursuing purpose over status and money?

Think about who you want to be as a role model (for your kids, your team, yourself). What example do you want to set?

How Life Supports the Leap

It's been about 16 years since I made that call. I truly thought I was making the choice of purpose and passion over money. And I was. But it's also this total cliche: do what you love and the money will follow.

Now when I work with founders who are in that exact same predicament I was in (terrified to make the leap, logically thinking they should choose money over purpose), I can tell them: I took the leap too. I walked away from guaranteed money.

Remember that terrifying phone call I made to Chris Schroeder? The one where I clicked over from my coach, heart pounding, to tell the CEO I was leaving money on the table to pursue coaching?

Chris was super gracious. He appreciated what I was doing.

And then he ended up hiring me as his coach. He was one of my first clients.

I was absolutely terrified making that call. My coach literally had to threaten to fire me to get me to do it. But courage isn't the absence of fear. You just have to be willing to feel it and take action anyway.

When you have the courage to follow what you're truly here to do, life has a way of supporting you in unexpected ways.

But none of that happens if you're not willing to make the first terrifying call.

With love,

- Dave Kashen

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