My dear friend and colleague, Samantha Leal, once bluntly asked me:

👉 What drives you?

She didn’t elaborate. She didn’t explain why she was asking. She just uttered those three bold words, and then stopped talking. 😳

I thought “damn, that’s an interesting and difficult question”, but before I could prudently ponder about how to respond, I blurted out an answer that seemed to come from nowhere.

It surprised the hell out of me.

A Career — in 3 Acts

If you ever want a crash course in self-reflection, start writing a newsletter. 🤦

When I launched Drunk Business Advice, I didn’t think I had very many personal stories that deserved to be published.  I assumed the bulk of these newsletters would feature profiles on other interesting business leaders.

But once I began writing about my career, the floodgates opened, and shit that I’ve been suppressing for years poured onto the page.

Some of it has been awesome.

Some of it has been mortifying.

👉 All of it has helped me gain perspective.

When we think about our careers, we tend to look back at it as a series of events—

But we rarely take time to examine the meaning behind those events, string them together, and squeeze helpful perspectives out of them.

Or at least, I had certainly never done that before. 🤷

But having now published 40 issues of Drunk Business Advice, I feel like I’ve compiled a drama-filled, Tony-Award-worthy Broadway play about my career — with three distinct “Acts”.

The distinctions between the acts boil down to the intentions that were driving my career forward during the early, middle, and current periods.

Those drivers turned out to be three wildly different (and often contradictory) motivating factors. 👇

🎭 Act 1: Survival

🎭 Act 2: Vanity

🎭 Act 3: Joy

📣 Now… places, everyone!

Act 1:  Driven by survival 🔪

💰 I had no money. 

🎓 I had no degree.

🏠 And at one point, I didn’t even have a place to live. 

My career in early adulthood was driven purely by survival. 

Sometimes I got lucky, and nabbed a great job. Other times, I was doing whatever work I could scrape together to get by.

This even included a one-night gig dancing on a podium in a nightclub so I could eat that week. 🪩

I kept my clothes on, but it was the first time I was ever offered the option of payment in cash — or cocaine.

A few of my survival jobs came with built-in exploitation, like unpaid overtime, or tips mysteriously vanishing into management’s pockets.

And, like most young women, I certainly tolerated my fair share of sexual harassment. While working coat check at a swanky Upper East Side restaurant, a regular offered me $5,000 per week to live with him.

I was so broke, that I almost entertained the idea. 🤦

But I survived this period of my life with only a few emotional bruises, so if your instinct right now is to feel sorry for me — don’t.

Because when your back is against the wall, like mine was, you get smarter. 

You get tougher. 

And you’re forced into situations that make you grow. 🌱

Act 2: Driven by vanity 💎

One of my favorite books from the last couple of years is The Good Enough Job by Simone Stolzoff.

Throughout the book, Simone exposes the pitfalls of “hustle culture”, and the risk we all take when we attach our identities and our self-worth to our jobs. 

But my favorite part of the book is a personal story from Simone.

At one point, he was considering enrolling in grad school, and sought advice from a mentor, who posed a question so poignant, that I think about it every damn day:

👉 “If you could go [to grad school], but you couldn’t tell anyone that you went, would you still do it?”

“For the first time, it made me consider my intrinsic motivation,” Simone explained in the book. “Was I actually interested in learning, or just in being someone with a graduate degree?”.

In other words — would this decision feed his soul, or his vanity?

I will admit right now that the lionshare of my career was designed to feed my vanity. 😬

After my life stabilized, and I exited “survival mode”, I made career decisions based primarily on esteem.

I wanted to be respected and admired.

I wanted to leave a mark on the world.

In my business, I took on famous projects, and chased clients with clout — even though it often meant I was being over-worked and underpaid.

I accepted jobs based on how spectacular they would look on my resume.

Every time I accomplished something, the first thing I would do is announce it to my family so I could brag about how important my work was, and they could tell me they were proud. 

But if someone had given me an ultimatum, and said “if you accept this job / project / client / assignment, you’re never allowed to tell anyone about it”...

I probably wouldn’t have accepted even half of them. 🤦

But — looking back, I did a lot of really cool shit.

If my vanity wasn’t driving me during that period of my life, I’m certain I would have missed out on imperative growth experiences.

I sure as hell wouldn’t have sold my house to pay tuition at Harvard if I wasn’t allowed to boast about joining the Ivy League—

Yet the value of the relationships I developed there far outweighed the credibility that the education earned me. Knowing what I know now, I would have absolutely gone to Harvard — even if I could never tell anyone.

Although vanity was front-and-center in my decisions during this period of my life, it definitely led me to some worthwhile experiences.

Act 3: Driven by joy ☺️

These days, I make career decisions based on pure, selfish, happiness.

Every time I’m considering an opportunity, I prioritize considerations such as:

👉 How’s the flexibility?

Can I regularly take the afternoon off to hit up a matinee, or go for a long walk on a beautiful day? Can I work from Europe for a month? I spent my 20s and 30s working overtime, and forgoing the kind of experiences that underpin an enjoyable and balanced life. No more.

👉 Who will I be spending my time with?

Do the people I’m working with have a good sense of humor? Do I learn from them? Would I be excited to have a beer with them outside of work? Life is too short to surround yourself with bozos and bores.

👉 Is the work fun?

Will I wake up in the morning dreading my to-do list, or excited to dive in? Of course there are always a few undesirable tasks involved — it is “work” after all. But that stuff should be greatly offset by the fun of it.

Money is important of course, because it allows me to live comfortably, and not worry about my future — which absolutely contributes to my happiness. 

But I’m no longer chasing the riches I once was.

And prestige is now something I sort of… avoid? I just don’t want the pressure of it anymore. 🤷

I simply want to be happy.

The reviews are in…

And the only reviewer who matters is… me.

You know how sometimes you think back to decisions you made in your younger years — and cringe? 😖

You criticize yourself.

You think “How could I have been so stupid?”.

You want to bury the memory.

I’ve made many surprising discoveries while writing about my career, but the most important lesson I can share with you is to force yourself to surface those regrettable moments.

When you do this, you’ll uncover:

• The intention behind your decision

• How you grew from it

• And how you can apply that wisdom in the future

Not only do I forgive myself for making some hellish mistakes — I thank myself for them.

Because each and every one of those embarrassing f*ck-ups led me to precisely where I am right now. ♥️

And I’m far from my curtain call, so there’s plenty of story left to discover. 🎭️ 

Cheers! 🍻

-Kristin :-)

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