When my little brother got married, and (unlike me) threw a big fat wedding, I was thrilled to reconnect with many friends from our youth.

Hell, I hadn’t seen most of these folks in well over a decade. It was going to be a bangin’ party. 💃 

At the rehearsal dinner, I spotted Jason –my brother’s best hockey buddy– from across the room. He saw me, wrapped his arm around his beautiful wife, and gently ushered her toward me.

“Honey,” he said proudly, “I’d like to introduce you to my first boss, Kristin.”

I melted.

🍻 THE DRUNK BUSINESS ADVICE 

👉 If you’re someone’s first boss, you’re teaching them way more than the job — you’re teaching them how to work. Don’t screw it up.

👉 The way you show up for your team will outlast your job title by decades.

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

But first…

For the next few weeks, I’ll be sharing snippets from my new weekly newsletter that helps you write faster, hit harder, and connect the dots between what you know — and what the world needs to hear. Go subscribe, dammit!

Great writing sounds musical.

If you’ve ever read something you’d describe as “flat”, chances are, it lacked rhythm.

Writing with rhythm is critical because readers don’t just process words — they hear them in their heads, like someone is reading to them. If your sentences all have the same structure, your writing becomes monotonous and unnatural. 

So even if you’re saying interesting shit, your reader will tune out.

The easiest way to add rhythm to your writing is to mix short and long sentences.

• Short sentences punch points through walls.

• Longer ones add depth and nuance.

• And when you use them together, they create a natural rhythm that mimics how humans actually talk — and think. Our brains glob onto that stuff.

I’d like to claim that writing with rhythm is far more complex than simply varying your sentence length, but truthfully, that one tweak will get you 90% there.

And in last week’s issue of Drunk Writing Advice, I shared two other tricks that will take your rhythmic writing over the top. 👇

P.S. — Reading and writing go hand-in-hand. If you’re a book (and business) lover like me, you’ll relish the Shelf Made Stories podcast!

I’m your… what?

I was expecting Jason to introduce me to his wife as “my friend, Kristin”, or “Jake’s sister, Kristin”, or even just “some chick named Kristin whose pool I used to pee in”.

But what he said was true. 

I was Jason’s first boss. Or one of them, at least. 

At the tender age of 16, I was in charge of his (then scrawny) 14-year-old ass when he began working at the ice rink my parents owned. By that point, I was a shift manager, having legally worked at the rink for two years — and under the table for three years before that. 🤐

My parents gave all the (non-screwup) rink rats a shot at their first part-time job every summer. Of course Jason was one of them. But when I saw him, I didn’t remember that.

I remembered him as my brother’s loyal buddy, and the kid who spent hours launching himself off our backyard trampoline.

(Yes. We had a pool AND a trampoline. And our business was an ice rink. We were a walking lawsuit, but damn it was fun.)

Instead of remembering me as his pal’s big sister, Jason remembered me as his first boss.

Because a first boss leaves a lasting impression — good, bad, or traumatizing. And at 16, I was clueless about that responsibility. (I was intently focused on scooping flailing toddlers off the ice without taking a toe-pick to the shin.)

F*ck, I think most 40-year-olds don’t realize the impact they have on someone’s lifetime relationship with work when they hire a youngster. It’s a huge deal.

So if you’re in that position right now — consider this your wakeup call.

When you’re someone’s first boss, your responsibility extends far beyond showing them how to do their job—

You’re showing them how to do work, period. 

You’re setting the tone for what “going to work” means for the rest of their lives. And since most people spend 40% of their waking hours “going to work” that's a crucial goddamn responsibility.

A baby leading babies

Leslie, now an in-demand retail operations advisor, kicked off her career like most kids—

Working at the mall. 

At 15, she applied for special work papers in New Jersey, and by the time she was 19, she was managing a Quicksilver store — and a team of high schoolers.

“I was a baby leading babies,” she told me.

For all these kids, it was their first job, first paycheck, and first time getting yelled at by an entitled customer.

And Leslie’s store would have gone to shit if she was just teaching them how to properly fold a hoodie. 

Her real responsibility was to teach these kids how to talk to strangers, listen, be persuasive, and achieve their goals in an adult world. Even if she didn’t realize it then.

But looking back, it’s pretty damn clear what she did right—

She led by example. Frankly, she didn’t know any other way to do it.

Instead of telling them what to do, she brought them with her as she walked up to a real customer, started a real conversation, and turned it into a real sale. 

And she didn’t hide in the office — she jumped in the trenches. Leslie cleaned fitting rooms, merchandised displays, and hauled freight right alongside her team. This wasn’t some clever intentional plan, (remember, she was just a kid herself), it was just what felt right to her. 

And she truly gave a shit. 

Leslie learned her team’s class schedules. She knew who had a crush on who. And she made the store a place where they could practice being grown-ups without getting their heads bitten off for every mistake.

Sweet validation arrived when these kids told her that the lessons she taught them didn’t just come in handy on the sales floor — they helped them have important conversations with their parents, teachers, and friends. ♥️

The cockroach

Joe, a medical device sales manager, has been with his current company for 13 years.

He joined right after college. And just… stayed. (Don’t worry I’ve already revoked his Millennial card. He's a disgrace to us all.) 

Joe credits his highly unusual tenure to his first boss — a woman in her fifties whose dynamic he describes as “almost like a mother-son relationship”. 

She set clear boundaries, defended him when others tried to take advantage of his youth and inexperience, and most importantly, focused her efforts on doing the “right thing” — even when it was the “hard thing”.

And without her influence over the seed-stage of his career, Joe would’ve noped out years ago.

When he transferred from Florida to New York three years into the job, he was thrust into “the wild f*cking west” — toxic culture, questionable management, and no guardrails. 

Joe told me, “I probably should have left, but I didn’t. I just stuck to the principles [my first boss] taught me. Like a cockroach, I’m still here — and the people who were behaving badly? They’re gone.”

Joe upheld the values instilled in him by his first boss, and made the decision to stick around to solve the problems he was seeing, rather than:

1. Getting the hell out (which is what I would have done)

2. Lowering his standards, and getting sucked into the mess

Now the highest-tenured member of his team, Joe’s been a first boss for dozens of fresh college grads over the years, and he takes that responsibility seriously.

“You’re the bridge between parental life and adult work life,” he astutely pointed out.

Joe knows he wouldn’t be where it is now without a badass first boss, so now as a badass first boss himself, he’s carrying a torch that was lit long before him.

Ballgown, anyone?

My bridge between “parental life” and “adult work life” was pretty damn fuzzy. My parents were my actual first bosses.

There are a lot of amazing things about growing up in a family business, but it also means that one tends to be older than most before ever reporting to someone other than mom & dad.

But I still think they were spectacular first bosses. And I’m not the only one.

After I left home to start my own life, but before my parents sold their business and retired, I was visiting the rink one day, and witnessed a confusing scene.

I walked into my mother’s office, and it was filled with… ballgowns. No shit. I was blinded by sequins.

What the hell was a rack of ballgowns doing at an ice rink? 🤔 

I should have guessed they were solving a unique workforce problem that, if you’ve never employed high-schoolers, I bet you’d never think of.

Some of the young ladies who worked for my parents helped support their families. And those courageous girls certainly couldn’t afford expensive prom dresses.

Therefore, they couldn't attend their proms. 😔 

Well, that broke my poor mother’s heart. She couldn’t bear the thought of a silly dress coming between these young women, and their night to remember.

So she put out a request to recent high school grads to loan their old prom dresses to a collection that could be borrowed from by girls who couldn’t afford to buy.

Dresses began pouring in, and with most of them being donated instead of loaned, the collection grew. It needed its own damn office, because mom was swimming in skirts while trying to process payroll.

This little initiative grew into a lasting staple of teenage employment at the ice rink. 

Even the girls who could afford new dresses opted to borrow from the collection, making the mature decision to put their hard-earned paychecks toward college or gas money instead of lace and chiffon.

So yeah.  My parents were pretty amazing first bosses. ♥️

—

If you’re a first boss, it’s easy to think your influence is as fleeting as a summer job. But the way you show up for your team will get baked into their work DNA.

You don’t have to be perfect. (God knows I wasn’t.) But you do have to understand the weight of the gig. If you model kindness, curiosity, and respect, they’ll take that everywhere. 

And if you act like an asshole, not only will they believe your behavior represents the future of their work life, but they may become assholes themselves.

And work doesn’t need more assholes.

Cheers! 🍻 

-Kristin

P.S. — If you enjoyed today’s issue, and want a behind-the-scenes look at how I craft Drunk Business Advice every week, don’t forget to subscribe to Drunk WRITING Advice!