I want to work until I make 100 million

This isn’t a clickbait headline. It’s a true story and that I can relate to (I used to want to sell a company for $50 mm). This proclamation came while speaking to a friend, who I’ll describe briefly below (and slightly modify details to preserve his identity).The friend is in his early 30s, works in finance in NYC, and single. He’s a super-connector, very spiritual, kind and witty, and just one of those fun people you always want to be around. He lives well, indulges in fine dining, and likes to travel a lot. Very humble dude who came from a modest upbringing — Let’s call him Justin, to make the story easier.

He does well at work and he really enjoys what he does. One of the frequent topics of conversation is about his desire to meet the lady of his dreams.

The Number

Why bring up Justin? We were talking about success and how to measure it.

He said to me:

“My goal is to make $100 mm — and then I’ll stop.”

I asked him to unpack that statement. First, we both acknowledged that this would be a very difficult thing to achieve. And while his role is very entrepreneurial, you don’t achieve that kind of wealth unless you truly start your own thing.

I asked him a few follow up questions?

Khe: Why $100 mm? Why not 47 mm? Or 2 mm?

Justin: I’m not sure, it’s a nice round number.

Khe: What would you do differently, once you hit that $100 mm?

Justin: I’d probably work a little less

Khe: You know you could probably work less right now, and given your current trajectory never have to worry about money for you and your future kids?

Justin: True.

Khe: What do you want to do with the $100 mm? Would you give it to your kids? You know that might fuck them up more than it would help them?

Justin: No way — it definitely would mess them up and I didn’t grow up that way. Maybe carve them out $1 mm (in today’s dollars) in a trust.

Khe: Then what would you do with the remaining $98 mm?

Justin: I’d want it to go towards something good. Having an impact.

Khe: You know that you can have a meaningful impact with much less than $100 mm?

Justin: True

Khe: You realize that getting to $100 mm could take the remainder of your adult life and would be really fucking hard?

Justin: Yeah — I’d have to sacrifice a lot in the process.

Khe: But you just said all you would do differently was “work a little less,” which you then admitted is currently possible!!!!!!

Justin: Good point

You won’t regret it!

Let’s do some Uncomfortable Introspection

It’s getting too complicated to write the Q&A, so I’ll go back to writing in the first person. I asked Justin to do some Uncomfortable Introspection— specifically to unpack the motivations of Fear and Ego in the desire to earn $100 mm.


Like many of us, particularly those of us who came from modest backgrounds, Justin has a fear of being broke. This is something that I can highly relate to and wrote about as I parsed my own fears.

The reality is, for the Privileged group of Medium readers (and Rad Readers) it’s highly unlikely that you’ll go broke — yet it remains a big Fear that holds us back from Living our Truths (pursuing our passions, becoming entrepreneurs).

(It also dawned on me after our conversation that subconsciously, Justin is probably thinking that being on a trajectory towards 100 mm will increase his probability of finding the right spouse. This is a very natural fear of abandonment— yet a faulty and potentially dangerous proposition. But we didn’t discuss this.)


This one was a no-brainer. Justin is around a (small, but non-zero) group of entrepreneurs and hedge fund managers, who are actually within striking distance of achieving the $100 mm goal (and some have achieved it). And, I don’t blame him, he wants to know that he can be considered in that group. There’s a delicious cocktail of Challenge meets Social Acceptance.

The Stories we Tell Ourselves

I felt strongly compelled to write this post for two reasons. First, I had many of 100 mm thoughts (as detailed here) so it is very relatable. Second, in many of my discussions (mostly with Financiers and Entrepreneurs) there is this arbitrary number that we all anchor towards. A blind proxy of “success.” We don’t really unpack how we even got to this goal. It’s a mix of laziness, blind tribalism, and ego. And like Justin, you realize that the goal would require a lot of suffering and the life we want is much closer to striking distance than we think.

So here are the stories:

Story: Getting to 100 mm will make me happy.

Hmmm: Yes, but at what cost. And what happens when you get there.

Story: Happiness is a series of Step Functions (promotions, bonuses, big ticket purchases).

Hmmmm: Happiness is the collection of small wins — being healthy, having a community, purpose in your work, self-awareness, the ability to love and be loved. (The only step function being having kids).

Story: I’m going to run out of money.

Hmmmm: You’re not. And are you honoring that fear by striving for such an extreme?

I want to highlight these stories because they are very real. But they’re just stories. And in this “complicated” journey we call life, we sometime fail to distinguish the story from the reality.

Thank you for reading!


PS — And if this story prompts you to lash out at Justin, just target your anger towards me instead… I felt all of those feelings myself.

PPS — If you find Justin’s aspirations disgusting, see the PS above (and direct away towards me). It is the byproduct of a very, very goal oriented capitalist mindset often (but not always) found in the Finance and Tech communities. I’m hoping to shine a light on some of the flawed thinking by sharing these stories, many of which I’ve lived through myself.

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