Community
September 2026
The Reinvention
About this article:
The Side Project is a reflective, personal essay about the people, places, and passions that keep marketers creatively alive outside of work — and what those pursuits give back in return.
There was no way I could have known it at the time, but marketing gets the credit for inspiring my mountain life and eventual gig as a part-time ski instructor.
It was the summer of 1995. A business trip to a regional marketing conference took me to the Colorado Rocky Mountains – specifically Keystone Ski Resort – for the first time. While my hometown of Chicago roasted in 100+ degree heat, I spent a long post-conference weekend at 10,000 feet of elevation in cool 60-degree temps, sampling mountain adventures from horseback rides to white water rafting to gondola trips up the towering fourteen-thousand-foot peaks.
Fast forward a decade and yet another business trip – this time to teach an email marketing seminar in Denver - landed me back in Colorado the week before my daughter’s school Spring break. Floridians at the time, we decided Spring break vacations should be taken in the mountains vs. the beach, so I booked a week in Vail. I skied (badly), she took snowboarding lessons, and we continued the tradition for at least another decade, always looking forward to that week of sliding on snow, slowly progressing and becoming more advanced riders, until we were fast enough downhill to feel like we were flying.
Life, as it tends to do, delivered both inevitable and unpredictable milestones. Divorce and an empty nest for me, college for my daughter. Through it all, my career as an email marketing consultant and digital strategist remained the constant that flourished over time. I was grateful.
Until that inflection point that left none of us untouched: the Covid pandemic.
Restless and ready to move west from Florida, Covid worked in my favor as I found a readily available summer rental near Breckenridge, Colorado in 2020. After four months in Summit County (home to five major ski resorts) my mind was made up: I made a permanent move there the following year. Much to my surprise, I found a place to live just 10 minutes from Keystone Resort where it all began.
Mountain life isn’t for the faint of heart – literally or figuratively. Full-time living at 10,000 feet of altitude cardio-stresses even the fittest athlete, and the seemingly non-stop menu of outdoor mountain adventures delivers a super-sized case of FOMO to the point of wondering how you’ll possibly have time for work, let alone laundry.
The key to the challenge revealed itself quickly during my first year in the mountains: get a part-time job working for a ski resort to earn a free ski pass and be paid to play! I snickered at the idea. Me? A ski instructor? They’ll never hire me! Mind you, I’m no advanced skier. I hate moguls (bump runs), trees (scary!) and mostly ski intermediate blue pistes, with an occasional groomed black thrown in. Little did I know ski instructing is far less about skiing and more about teaching. Now that I knew how to do.
I applied to teach kids at Keystone Resort and was hired as a fledgling instructor at age 56. The training was solid, and fun. The instructor clinics made me a better skier. And I even earned my first PSIA (Professional Snowsports Instructors of America) Certification that year.
But it was the kids that made it all worthwhile. To take a group of five-to-twelve-year-olds – most of whom were on skis for the first time – bundled, cold, often crying (and sometimes puking) from “never-evers” to mastering their first downhill run on the bunny slope, laughing and confident, maybe even able to then ski with the rest of their family – lit me up in a way my full time career never could.
Out “on the hill” in the sunny, snowy alpine has a way of keeping you present, fully in your body, out of your head (in a good way), and energized. And when you’re done, you’re done. No stream of email you can never catch up on, no extra work you can do at home. Just a cold après beer or hot chocolate and a warm Epsom salt bath at the end of the day, or a snuggle by a roaring fire.
Aside from the obvious perks - a free season’s ski pass, skills clinics, extra income, and physical exercise - my two seasons as a part-time children’s ski instructor at Keystone also delivered unexpected benefits that seeped into my full-time career and life: better time management; greater empathy, patience, and nurturing; intentional self-care; lower stress and anxiety, and more balance.
After two seasons of teaching, I reached yet another unpredictable inflection point - I wasn’t loving it like I did at the start. This illuminated perhaps the greatest take-away of my accidental side hustle: don’t turn something you love into a job.
So I didn’t. Now I buy a season pass because I ski for fun, for me, for freedom. I ski because in a profession which requires a heavy cognitive load and sharp intellect, I get to turn my brain off and tune into my body. Plus, I don’t think I’d survive a snowy winter if I couldn’t go play outside in it; I need to have fun!
And sure, there’s the inevitable tension all of us working mountain mavens encounter when it’s snowing buckets in Colorado: work or ski? But somehow, we manage to do both. And yes, I’m lucky enough to be self-employed and make my own schedule. Because let me tell you, an epic powder day in the Rocky Mountains is not to be missed!
