Plot Twist: Midlife Career Change, Part Deux

A year ago, a midlife career change was the last thing on my mind. I already had it, right?! Amid the pandemic, while at home with my newborn, I founded Wabi Post, my LLC, offering marketing, executive branding, and strategic communications for incredible clients and companies.

Months later, while reflecting on our worst family vacation travel day in a blog post, I was being pursued by a recruiter and conducted a few interviews during that trip.

Fast forward nearly three years and two promotions, I found myself working my first 70+ hour week (not my proudest moment).

If you asked my family, friends, book club, or even my hairdresser, they’d confirm I was constantly overworked—showing up to every appointment with my laptop. Once, I brought my laptop to a cherished monthly book club night. I even worked from my couch during a Packers game one weekend—a clear red flag for this Wisconsin native! Looking back, I realize I was stretching myself too thin, but those moments taught me how to prioritize and manage time effectively in my new role.

Eight months ago, everything changed.

If you had told me then that I’d leave my 18-year career in healthcare marketing to become a licensed independent health insurance agent, I probably would have laughed. My career felt steady, established, and deeply tied to a niche industry I knew inside and out. But sometimes life has a way of nudging us in directions we never expected—directions that surprisingly end up being exactly where we’re supposed to be.

This is the story of how a seeming setback became the catalyst for a new opportunity I’m incredibly grateful for today.

A Bitter Pill to Swallow

In February, my role in healthcare marketing came to an unexpected end. There was no safety net beyond my resilience and resolve to match with a job more aligned to my values. Like so many others who have experienced job loss, my emotions were wrought with a mix of resentment, relief, anxiousness, and excitement. Work had always been a huge part (clearly way too big a part, at times) of my identity, and now the question of “what’s next?” loomed larger than ever.

I dove into the job market, revamping my résumé, reconnecting with recruiters, and applying for hundreds of positions while attending countless interviews. None of the opportunities felt like the right fit.

Telling the Family

When I shared the news with my dad last winter, he offered his signature wisdom. As I excitedly described my top three career prospects, he quipped, “Well, if those don’t work out, you can always dig ditches or sell Medicare with me!” (A classic dad joke, of course.)

Months later, when I updated him on my latest career prospects, he got serious: "I think you would be great as an independent insurance agent. You are incredibly organized, have an extensive background in healthcare, are very driven, and great with people. Think about it.”

Maybe She’s Born with It

My dad, Mark Christiansen, founded Christiansen Insurance Services nearly 20 years ago, specializing in helping Wisconsin residents—especially those navigating Medicare—find personalized coverage. Growing up, I watched his dedication to clients, working weekends during Medicare’s annual open enrollment to ensure they had the right plans. He’s earned accolades like Front Runner, Champions Circle, and Top-Rated Agent status on national Medicare agent directories. (While researching online for this blog, I found his profile listing “2 career holes in one!” under Honors & Awards—classic Dad humility.)

The testimonials echo what I remember hearing. I recall stories about the relief and gratitude people expressed when he was able to synthesize the overwhelming complexity of all the various Medicare Parts, Plans, eligibility criteria, and options so they could understand the offerings and ultimately identify the ideal, customized plan to suit their healthcare needs and preferences.

Universal truth: we all must have health insurance. We need it.

At first, I hesitated. I have 18 years of experience in the highly regulated healthcare industry.

When I founded Wabi Post, maybe it was the pandemic, maybe it was postpartum—but what I really missed was cultivating relationships with my clients and the camaraderie of working in a high-performing team. (YEP—you guys know who you are! 😊)

However...

The more I thought about it, the more excited I became. Everything I loved about my career—truly listening to my customers to understand their priorities and pain points, simplifying complex content to make it easier to understand, guiding strategy, and building relationships—are also at the heart of being an insurance agent.

As summer raced by and the school year loomed, I paused my job search, graciously withdrew from a promising third-round interview (out of seven!), and went all-in on earning my pre-licensing education certification to become an agent.

“What, Like It’s Hard?”

Becoming a licensed insurance agent was no small feat. According to the National Association of Insurance Commissioners (NAIC), Wisconsin’s 2023 first-time pass rates for the Life 22-01 and Health 22-03 exams were a daunting 60.3% and 58.1%, respectively.

Channeling my inner Elle Woods, I embraced creative study methods: flashcards, changing study locations, watching Insurance Exam Queen videos on repeat while walking our dog, and taking practice exams. I even wove insurance jargon into daily life: “Kids, look at those pull-tabs! They’re a speculative risk—there’s a chance we lose, but we could also win!” (For non-Wisconsinites, pull-tabs and shake-of-the-day are fun tavern games involving small bets for a chance at a prize—come visit to try them!)

We Did It!

A few weeks later, I became a licensed independent insurance agent in Wisconsin (and soon, Florida!). I’ll focus on life and health insurance, with a primary emphasis on Medicare, and I’m thrilled to work alongside my dad at Christiansen Insurance Services. This isn’t just a new job. It feels like a calling. Understanding my clients’ needs, helping them identify a customized coverage plan, and ensuring they feel confident in their healthcare coverage is work that truly matters.

What This Means for My Network

For those who know me from my marketing and communications career, I’m not leaving that world entirely. I’ll still take on select brand strategy and marketing contract projects, as I find that work rewarding and fun. And, if you, your parents, or anyone in Wisconsin (or the 18 other states we’re licensed in) are approaching Medicare or navigating coverage decisions, I’d love to help. Now is the perfect time:

👉 Medicare Annual Open Enrollment runs October 15 through December 7.

During this period, Medicare beneficiaries can review and adjust their coverage for the upcoming year. It’s a critical window, and it can be overwhelming without guidance.

That’s where I/we at Christiansen Insurance Services can help. You can learn more at cismedicare.com, or simply reach out directly to me or my dad. We’d be honored to walk through the options with you.

Looking Back, Looking Ahead

When I look back on the last eight months, it’s tempting to focus on the hard parts: the feelings of resentment, rejection emails, the stress of uncertainty, the sheer exhaustion of trying to find my place again. But what I choose to see instead is the resilience I built, the lessons I learned, and getting to experience exactly what Reverend Mother says to Maria in my favorite movie: “When the Lord closes a door, somewhere He opens a window.”

Sometimes the path forward isn’t the one you expected. But it just might be the one you were meant to take.

I’m grateful for this new chapter, for my family’s support, for my dad’s mentorship, and for the opportunity to serve people in such an important way. And I’m grateful to all of you—my friends, colleagues, and professional community—for cheering me on as I step into this next season.

🙌 Here’s to new beginnings, fresh opportunities, and the reminder that even “setbacks” can lead to something truly good. Wishing you a happy, healthy, wonderful Q4.