It all started with a bad head shot

Anne, why the career switch? Was this something that you had been thinking about for a while?

The decision was quick. The why is a much longer answer.

There was nothing technically wrong with the photo. It was a standard head shot. The lighting may have been a little harsh. Otherwise, my eyes were open, my gums weren’t showing, my highlights were freshly done. I wore a navy blazer over a white blouse. And a lot of makeup to achieve that perfect no-makeup look. Still, the photo looked nothing like me.

My job had been eliminated 18 months prior. I knew from the first week, when I was introduced as the new “matriarch of marketing” that it was a bad fit. This was confirmed when I received my first performance review. There was no feedback about my actual work; it was all about my “abrasive and combative” personality. For reasons that only made sense at the time, I stayed. Three years later, I was still there and my motivation and confidence were at an all-time low. I had never been so happy to lose a job.

I was fortunate that I had a long runway to figure out my next step, along with a patient and encouraging husband. I knew no matter what I was going to do, that taking care of my health (both mental and physical) was important. So I went all in – found a new therapist, worked with a health coach and nutritionist, and started going to the gym daily. I was food prepping and working out like it was my job, which it sort of was.

Roughly a year after my corporate exit, I had lost about 50 pounds, started networking, and was taking steps to launch a marketing consulting business.

This wasn’t my first year-long sabbatical. I took one in 2014 after walking away from what had been a dream job. I was burnt out, self-medicating with Grey Goose, and needing time to finally process some significant losses. I spent that year working out, doing yoga on the beach, and teaching myself to play the piano.

My next sabbatical came four years later. Another bad culture fit. Actually just a bad culture.

So here I was in 2025, having spent another year recovering from my previous job before looking for the next. I was starting to think that may have been a little odd.  Don’t most people just take a week or two to recharge?

I had worked in advertising and marketing for 30 years. When I entered the field, having no idea what I wanted to do, I loved it. I was on the creative side, developing concepts and writing ads with an art director partner. It was perfect for someone like me – I was a smartass with a lot of shallow trivial knowledge who thrived under impossible deadlines. And it was the perfect time. The dot-com boom of the 90s brought in lots of money and an appetite for crazy ideas. Then the inevitable dot-com bust arrived. Along with my recognition of the realities of agency life. Only 3% of creative leads were women and, at 31, I was rapidly aging out of the industry.

It was time to go to the dark side – corporate. Not only did I go corporate, I went financial services corporate, which was about as conservative as an industry gets. I was newly married and, for many years, the primary breadwinner. As opportunities became available, I grabbed them, seeing dollar signs and ladder rungs and giving little thought as to what I wanted to do. My dysfunctional childhood was the perfect preparation for this world – I could quickly read rooms, appease the most difficult colleagues, and find a way to tolerate nearly anything. I leveraged this into a series of global leadership roles.   

After my last layoff, the market had changed and so had I. At the beginning of COVID, my husband and I accelerated our 10-year plan and moved from Chicago to a rural log home on the shore of the Bay of Green Bay. Finding an executive-level position where I could work remotely or commute from Door County was going to be next to impossible. I decided to go the fractional CMO route…along with every other laid off 50+ female marketing executive. I had hustle, so I knew I’d be able to eventually figure out a niche. I thought through my strategy, put together a plan, and had everything laid out.  Updating my headshot was the final, missing piece before starting a big self-promotion push.

Then it struck me. There was no joy in that photo. There was no spark. I was doing all the things, but my heart wasn’t in it. And, at that moment, I realized I was done. I no longer wanted to work in marketing.

During my sabbatical, I became certified as a personal trainer and started coaching CrossFit. The gym had been my refuge for the past 15 years – it was where I went when I was stressed and it was where I found community. That wasn’t always the case. I was a chubby kid with coke-bottle glasses. Growing up in the 70s and 80s, exercise was something you did to manage your weight. My husband, always a hard-core athlete, introduced me to weightlifting and CrossFit in 2010. Finally, here was an approach to fitness that was about getting stronger rather than smaller.

When I started taking the training courses, it was entirely for my own reference and to keep my mind active. Coaching CrossFit was for fun and to get more comfortable speaking, teaching, and being loud in front of a group. But when I started coaching, I realized just how rewarding it was to help someone achieve one of their goals, such as a first pullup or a weightlifting personal best. Even more rewarding was the woman, who after her first class, where she looked miserable and was too nauseous to finish the workout, told me it was the first time she ever felt welcomed and comfortable in a gym.

That comment meant more to me than any of the corporate kudos I received. Those always felt obligatory and performative for efforts that helped rich finance bros become even richer finance bros. All my logical thinking, careful analysis, and methodical planning went out the window when I realized what that photo was telling me. It was time to do something that brought me joy.