Last week, I shared a story about the time my opponents tried to get me deported.

Why? Because I started a new job that carried f*ck-ton of clout.

👉️ Astoundingly, I was only 22 years old when this happened.

Many of you reached out to ask how the heck I managed to get that job in the first place.

Fair question. 🤷 

Not to brag, but landing jobs I’m not qualified for is sort of a special talent of mine. 😘

Today, I’m going to roll back time even further, and take you to the place where it all began — the middle of New York City.

👉️ What was your first job? Join the conversation on LinkedIn.

Frosty foundations in Florida

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 crazy as building an ice rink in Florida may have been, it worked out for me:

👉 It enabled me to become a serious competitive figure skater – something that probably wouldn’t have been an option had we not owned the rink.

👉 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 was trusted with actual management responsibilities as young as 14 years old.

👉 I earned full accreditation as a certified and insured ice skating coach, and since I had begun coaching as an apprentice in my early teens, I compiled a list of happy clients willing to vouch for my skills by my 18th birthday.

So when I moved to NYC to (try to) go to college, I had a plan— 

I would earn money teaching ice skating. ⛸️ 

It was a good plan.

The money is excellent, the schedule is flexible, and it’s way more fun than waiting tables (which was plan B).

There was just one thing I had to do — convince an ice rink to hire me.

The first of many jobs I wasn’t qualified for

So there I was, in New York City, enrolled in school, bleeding cash, and needing to find a job.

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 long-standing rinks like Rockefeller Center or Central Park.

And it looked like a spectacular place to work. 😍

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 manager came out to speak with me. Much to my disappointment, he told me that they were fully staffed with coaches. 😔 

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

I responded that I had experience in rink management. 

Of course, this was technically true.

But managing a suburban ice rink under the supervision of my parents was dramatically different from managing an entertainment mecca in the middle of the busiest 10 square blocks in the world.

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

But as fate would have it, they had just lost one of their four venue managers at the last minute, and were desperate to hire someone to fill the role.

Like…really desperate.

I was honest with this guy. I told him that I had only recently moved to NYC, and I was a student, so I couldn’t work traditional 9-5 hours.

That was totally acceptable to him — he needed someone to cover nights and weekends anyway. And my experience “managing” an ice rink in Florida was sufficient (in his eyes).

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

Um. What. 🤯

I accepted, of course.

The first of many gaffes

On my way out, I only had one question — what should I wear? (Looking around, I could see employees sporting matching winter jackets and vests.)

His response was “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.

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

Uhh… black pants? 🤨

He pointed to himself, sporting: 

• Slacks

• Shiny shoes

• And a dress shirt 

He looked like he belonged in an office, not an ice rink. Apparently this was the dress standard for 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.

Not a great start. 😬

Also, I had no money, and therefore no way to buy additional appropriate outfits for work.

To top it off, I was in-between apartments during this period.

The first place I lived in NYC came with a roommate from hell, and I had found a new apartment, but I was facing a month of homelessness before my new sublet started.

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 and could buy a few suitable items. 🤫

The benefits of being green

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

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

⛸️ I oversaw an operations team, customer service 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 violent incidents.

I didn’t always make the right call, 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 did the right thing from a moral standpoint. As it turns out, that’s often the best way to go.

And I was unquenchably eager to learn. I came early, stayed late, asked tons of questions, and never repeated a mistake.

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 learned a ton about high-level operations management in a remarkably short period of time.

Don’t ask, don’t tell.

Toward the end of the season, one of my bosses invited me out for drinks with some of the senior managers. 🍷

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

I just had one innocent question…

• ME: “Do they card?”

• HIM: “Wait… you’re under 21?”

• ME: “I’m 18.”

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 in my 20’s based on my “experience”, and the fact that I, ya know, had that job.

But they never would've given me that job if they had known how old I was. 

Thank god they didn’t ask. 🙏 

Don’t squander opportunities with a shitty work ethic

After the season concluded, my next job came from a connection I made during my time at Bryant Park.

Before I knew it, I had compiled two management-level positions from reputable NYC companies on my resume. Score. 👊 

And while it definitely wasn’t a linear path (at one point I did, indeed, have to wait tables) the Bryant Park gig provided the credibility I needed to land yet another job I wasn’t qualified for:

⛸️🏒🥌 Launching the largest ice sports center in the Southern Hemisphere.

As lucky as I was to have been handed the job at Bryant Park in the first place, I worked my ass off to keep it.

Luck eventually runs out. Tenacity doesn’t.

Cheers! 🍻

-Kristin :-)

P.S. — Don’t leave me hanging. Hop over to LinkedIn and tell me about your first job.

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