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I met Alison on Instagram, and we instantly bonded over climbing the corporate ladder and leaving it behind.

What I love about Alison's story is that she didn't wait for a dramatic exit to start building something of her own. While holding down a high-performing sales career and closing $10M in deals, she and her husband built a podcasting business on the side.

And when Alison's own layoff came, instead of rushing to replace the paycheck, she chose a creative sabbatical instead.

Alison’s story is a living example of building a business before you need it and pivoting in real-time.

Jump to:

Alison, thank you for chatting with me! Can you tell me about your early career journey? How did you get into Sales?

I never in a million years could have imagined going into sales—it happened by accident after applying to a Customer Success role at a company and realizing the job wasn’t for me. A month later, I got a call from that same company offering me a role in sales instead!

Prior to that, I worked at luxury hotels, small marketing agencies, did freelance work for 7-figure course creators and bestselling authors.

I was very much a generalist and jill-of-all-trades, but one thing I DID have that always served me well in sales was genuine enthusiasm, persuasion, and the ability to build trust with people quickly.

You closed $10M in Sales working in tech. From the outside, it looked like you'd "made it." What was actually going on underneath that?

Sales is a nonstop hamster wheel. Don’t get me wrong, I LOVED the dopamine hits of closing a deal and receiving my quarterly commission checks, but the more the years went on and my quotas moved further and further from the original goal post, the more I began drowning in the stress of it all.

I had a beautiful home and never worried about money, but I started to feel complacent. I wondered if I possibly had an even bigger purpose for my life, but I was afraid to leave.

When did you realize you wanted to start Podcasting for Creatives with your husband? How did you do that and a full-time job?

I love having a business in the podcasting space. My role requires only about 3-5 hours per week, so it was doable when I worked full-time, but there were definitely some late nights.

The business started as a side hustle—our first year, we made a little over $2,000! Now, it’s been my husband’s full-time job for 5 years.

Alison & her husband, Steve, running their podcast business together! 

There was a moment when you realized something had to change in the way you and your husband were working on the business. What happened?

If I can give any piece of advice to a newer entrepreneur, it would be: don’t scale too fast! Three years ago, we had blown up our business to 22 clients—that’s 22 podcasts my husband was editing (with a little bit of help from a contractor).

The constant 10+ hour days and weekend work caused an unexpected ER visit and 3-day hospital stay where Steve’s heart rate soared to over 180bpm just laying in a hospital bed. That really put things into perspective.

We let go of nearly half our clients, and ever since, have been much more intentional and slow to scale.

You recently got laid off from your high-paying tech job. Many people would've immediately started applying for a new job but instead, you chose a “creative sabbatical”. What led to that decision? 

My 80-90-year-old self is truly my north star. I never want to look back one day and have regrets about how I lived my life.

I’ve had big dreams for years of creating content, writing, and inspiring people with my story, but I always let perfectionism and fear of failure get in the way, so I’d stay paralyzed and procrastinate.

I’m no longer letting that be my narrative. My intuition is guiding me every day, and I’m now nearly 7 months into this career break with no intention of stopping it anytime soon!

You've been helping others run their own podcasts for 7+ years, and now you're stepping into your own creative identity with your podcast, Real Time Creator. How has that shift felt for you?

Hosting my own podcast has been absolutely amazing. Every week, I share a 15-20 minute episode about my career break. You get to see this very raw, vulnerable unfolding of it. The budget cuts I made, the job opportunities I turned down, the self-doubts, the habits and identity shifts I’m re-wiring.

I feel seen. I feel like my words are inspiring people, which was exactly the goal. It has increased my confidence tenfold, and now I’m ready to start tackling video next!

Alison welcoming in her new era of following her content creation dreams.

On your “creative sabbatical”, what are you paying attention to as you figure out what comes next?

I’m noticing where I’m getting curious. I’m allowing myself white space to reflect and tap into my intuition.

I’m also treating myself. I will be going to a writing retreat this summer in upstate New York with an author I admire. I also feel like I am being led in this direction and just have to trust it, even if it doesn’t make total sense right now.

Where can people connect with you and learn more about your work?

I love hanging out on Instagram. You can find me at @alisonkinsey.

And Real Time Creator is my podcast where I’m publicly documenting my career break from tech and my late 30’s reinvention. You can tune in on Apple Podcasts and Spotify. If you’re in a similar space in your career or can relate to my story, send me a note!

Alison’s advice for the high achiever who feels stuck in a career that looks great on paper, but deep down they know they need something different? 

I know EXACTLY how this feels and if you’re in tech, I know how brutal and all-consuming it can be. I would take some honest time to reflect and look at your values.

  • Does your career fully align with your values?

  • Are you living and thriving in your purpose and what you were meant to do on this planet?

The hardest part will be the courage to change it if you realize there’s misalignment, but I have been so surprised now that I am on the other side.

I’m the happiest I’ve been in a long time. I’m realizing I can live off of a LOT less income, and that the world is my oyster.

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