As the autumn crispness sneaks into New York, and the seasonal ice rinks begin welcoming stampedes of skaters, I’m reminded that the first job I wasn’t qualified for is celebrating its 20th birthday. 🎂

👉 When you lack experience, use your conscience to make decisions. They’re often the right ones.

👉 And if luck hands you an opportunity, treat it like it’s the only thing between you and homelessness.

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

I spent my teen years working at an ice rink — in Florida. ☀

I know what you’re thinking. Who the hell builds an ICE RINK in Florida?

Answer:

As batshit crazy as building an ice rink in Florida may seem, it really worked out for me:

👉 It enabled me to become a competitive figure skater – a wildly expensive sport that my family would have never been able to afford had they not ventured into the ice rink industry.

👉 While other teens were cutting their career teeth as “sandwich artists”, or selling overpriced t-shirts at PacSun (no shame, those are solid first jobs), I got to work for the family business. This meant I was trusted with actual management responsibilities as young as 14 years old.

👉 I earned full accreditation as a certified and insured ice skating coach by my 18th birthday.

As much as I loved the family business, I was itching to venture out on my own — and I had my heart set on New York City. Which is, ya know, an impossibly expensive place to live, especially for a kid.

I didn’t have any money, but I did have a plan — I would earn my living teaching ice skating. ⛸

It was a good plan.

There was just one hurdle I had to clear — convincing an ice rink to hire me.

I had learned that a new seasonal ice rink was opening up in Bryant Park, steps from the world-famous Times Square. 

Since this was a new venue, I figured it was where I stood the greatest chance of nabbing a coaching position, as opposed to historical icons like Rockefeller Center or Central Park.

And it looked like a spectacular place to work. 😍

For the youngins in the crowd, here’s a fun fact:

Back in those days, people didn’t apply for jobs on the internet. For an entry-level role, the standard practice was to just walk in and ask for a job.

Which is exactly what I did.

The GM came out to speak with me, and much to my disappointment, he informed me that Bryant Park was fully staffed with coaches for the season. 😔

…But he immediately followed that with — “Do you do anything else?”

I (pretty damn recklessly) responded, “Yeah, I used to manage an ice rink in Florida.”

Of course, this was technically true — but managing a suburban ice rink under the supervision of my parents was dramatically less complex than managing an entertainment mecca in the middle of the busiest 10 square blocks on the planet.

👉 Let’s be clear — I was not at all qualified to manage this place.

But as fate would have it, Bryant Park had had already proven to be too much to handle for one of their new venue managers, and the GM was desperate to hire someone to replace him.

Like… really desperate. He spoke to me for about 10 minutes, then offered me a venue management position on the spot.

Um. What. 🤯

I accepted, of course.

On my way out of the “interview”, I only had one question — what should I wear to work on my first day? (Looking around, I could see employees sporting matching winter jackets and vests.)

The GM responded with: “black pants.”

Perfect. I assumed I’d be given something to wear on top when I rocked up for my first day of work.

That day arrived, so I dressed in a pair of black coaching pants, and threw on a Red Wings hockey sweatshirt to take the subway to work.

I strolled in, nervous as shit, but trying to convey cool confidence with a big dumb grin on my face.

My new boss’s jaw hit the floor when he saw me. “What the hell are you wearing?”, he blurted.

Uhh… black pants? 🤨

He took a dramatic step back, and pointed to himself, sporting: 

He looked like he belonged in an office, not an ice rink. Apparently this was the dress standard for venue managers — the uniforms I had seen were for staff.

“You can’t work here like that. You have to go home and change.”

So I took the subway all the way back to where I was living in Brooklyn, changed into the only suitable outfit I had, and hustled back to actually begin my first day.

Y’all — I still cringe when I think about it. 🤦

Also, I had no money, and therefore no way to buy additional appropriate “business attire” for work. To top it off, I was in-between apartments during this period (read: homeless).

Luckily, a rich friend was visiting her family for a month, and generously offered to let me crash at her place while she was away. Even more luckily — she was my size. And she had a closet full of gorgeous designer clothes…

Which I borrowed (without permission), until I got my first paycheck. 🤫

As rocky as my first day was, it didn’t even scratch the surface of what was in store for me at Bryant Park.

And looking back, I’m absolutely astounded by what I was trusted with:

⛸️ I oversaw an operations team, events team, ice maintenance team, security, medics, and coaches, all serving 2,000+ skaters every day.

🎥 We were hosting broadcast events for Good Morning America, appearances by Olympians and Stanley Cup winners, and a revolving door of CEOs, celebrities, and sporting royalty.

🚨 And I was dealing with the chaos of running a busy NYC entertainment venue, with issues like theft, injuries, and even violence.

Fights were breaking out in the line to get in (which always wrapped around the block)…

Employees were stealing admission wristbands and selling them on the street…

And in true New York-fashion, a psychotic (or drug-induced) maniac once tore past security, ran inside the venue, and terrorized a sweet midwestern family until we could get NYPD to physically remove him.

Look — I didn’t always make the right decisions as I navigated this labyrinth of new and outrageous challenges, but being hopelessly naive surprisingly worked in my favor.

Here’s why:

👉 Rather than viewing problems through the lens of a “desired outcome” (as we tend to do once we gain experience and maturity), I approached every decision with my conscience.

Because frankly, that’s all I had. 🤷

Every day, I showed up to work and simply tried to do the right thing from a moral standpoint — instead of covering my own ass.

As it turns out, that’s often the best way to go.

And after a few stern talking-downs, usually resembling “this ain’t Florida, kid — keep your head in the game,” I started to get the hang of it. So while I definitely caused some f*ck-ups, I managed to not get myself fired, mainly because it was clear that my heart was always in the right place.

And I soaked it all up like a fat sponge.

Toward the end of the season, my boss invited me out to a bar for drinks with some of the senior managers of the venue’s holding company. 🍻

Amazing! I was officially being accepted as a valued member of the team.

I just had one innocent question…

I wish I had a photo of his face at that moment.

I never lied about my age — they just never asked. Everyone assumed I was at least in my mid-20s. And I’m pretty damn certain they never would've given me that job if they had known I was just an 18-year-old kid.

Thank god they didn’t ask. 🙏

Cheers! 🍻

-Kristin

P.S. — Check out my appearance on the the most unhinged business podcast on the internet! Many thanks to Jared Correia for inviting me to join him. 🍻