(Let me preface this by saying that I have worked with many Gen Z-ers in recent years, and they were all resourceful, creative, and hard-working.)

But this particular 22-year-old claimed her biggest career roadblocks were “decision-making” and “execution”.

So… her biggest roadblocks were… herself?

During a time when recent college grads face one of the bleakest job markets in history, the idea that someone’s career was stalled because they couldn’t make a damn decision seemed profoundly absurd to me.

👉 Skipping steps probably isn’t the best idea. You might get there quicker, but will you have the skills to be successful once you’ve arrived?

And now — the story behind why this advice matters. 👇

So my advice to this girl was, basically: “Get the f*ck out of your own way”. Just start working. She was trying to design her career before she even had her first job.

I assured her that the career she thinks she’s going to have will change 50 times before she reaches my age, so she just needed to put her head down and begin experiencing the world of work.

She never responded. I think I may have hurt her feelings.

But this interaction got me thinking… Why does this girl feel paralyzed by making the “right” career decision? Why, at 22, was she trying to reverse-engineer her entire life?

Here’s my theory—

It’s because of assholes like me.

I’m part of an eco-chamber of career & self-help “thought leaders” (I hate that term) who peddle the importance of finding balance, meaning, and happiness in our work lives. But we’ve only earned the right to give that advice after years of grinding away — ignoring the importance of balance, meaning, and happiness in our work lives. 🤦

Does this make our advice… bad? No.

But it’s definitely not suited to a 22-year-old who just needs to get out in the world and experience shit. The approach that made me successful then is very different from the approach that’s keeping me successful now.

Back then, I needed to work my tushy off, and take every opportunity that came my way. Sleep was optional. Happiness was not even in my top 10 list of priorities. “Mental” and “health” were two words that never appeared in the same sentence.

Now, I’m established. Two incomes, no kids, and a large enough nest egg to retire in the next decade. So I’m privileged enough to prioritize things like –you guessed it– balance, meaning, and happiness.

Y’all — if you ever want a crash course in self-reflection, start writing a newsletter.

In review of the 103 issues of Drunk Business Advice that have now been published, I’ve identified three distinct periods in my life. Like a Broadway play, my career has three “Acts”, clearly divided by a very important question:

What was driving me?

Those drivers turned out to be three wildly different, and often contradictory, motivating factors:

🎭 Act 1: Driven by Survival

🎭 Act 2: Driven by Vanity

🎭 Act 3: Driven by Joy

And the advice that worked in one “Act” of my career wouldn’t have killed me in another “Act” of my career. Let’s peek behind the curtain.

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, and a fierce determination to not have to rely on anyone — ever. So to maintain my independence, 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 an 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 to grow.

The resilience and street-smarts I learned in my career’s “Act 1” tee’d up an “Act 2” I never could have predicted.

One of my favorite books from the last few 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?”

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

That question was a sucker-punch to the face.

But I will freely admit to you all that the lion’s share 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.

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

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

And every time I accomplished something, the first thing I would do was 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. 🤦

However, on reflection, 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 important growth experiences.

I sure as hell wouldn’t have paid a fortune to attend Executive School at Harvard if I wasn’t allowed to tell people about it. That decision was 100% driven by vanity. Yet, the value of that experience far outweighed the “credibility” I was seeking.

With the perspective I’ve gained now, I would have absolutely gone to Harvard — even if no one could ever know.

So while vanity was front-and-center in my decisions during “Act 2” of my life, it drove me to some incredibly worthwhile experiences.

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

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

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 so much of my 20s and 30s working overtime, and forgoing the kind of experiences that underpin an enjoyable and balanced life. I’m not that person anymore.

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? I don’t have enough time left in my life to surround myself with bozos and bores.

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, but I’m no longer chasing “rich” — I’m perfectly happy with “comfortable”. And projects with prestige are now something I sort of… avoid. I simply don’t want the pressure of it anymore. 

Doing whatever the hell I feel like doing, and prioritizing happiness, is my “Act 3”.

Folks who give career advice (like me) are speaking from a privileged perspective. And that privileged perspective was earned over years of f*cking up.

Isn’t the purpose of giving advice to help others learn from our mistakes? To help them “skip steps”, and achieve more in less time?

I’m going to challenge that paradigm. 

Because let’s face it — as the advice-givers, we have no way of knowing how we would have turned out if we had taken our own advice back when we were at the beginning of our career.

In that context, I think we’re all pretty full of it.

Cheers! 🍻

-Kristin

P.S. — I don’t just write Drunk Business Advice — I bring it to life on stage. And I’d love to speak at your next event. Hit reply or click here to learn more.