👋 About Drifting Dad

Life’s too short to stay stuck in a story that no longer fits.

Hi, I’m Jason — a midlife explorer, travel advisor, financial strategist, and reinvention advocate helping others design a life that works better now…not someday.

After a long and successful corporate career in finance and treasury leadership, I reached a turning point — one that many of us do after 50. My sons were heading off to college. My house no longer felt like the right fit. And the conventional path I’d followed for decades didn’t reflect what I actually wanted next.

So I did what many might call “radical,” but what I simply call aligned:
I sold my house, downsized my life, and began building something new — grounded in freedom, purpose, and smart strategy.

That journey led me to create Drifting Dad — a brand for curious, growth-minded people navigating their second act with clarity and courage.

Are you ready to join the nearly 40,000 followers and subscribers already engaging with me and my content? Let’s do this!

What I Believe

Midlife isn’t a crisis — it’s a creative opportunity.
You can travel meaningfully without quitting your job or blowing up your life.
Financial clarity and lifestyle freedom aren’t mutually exclusive — they support each other.
Small changes, done intentionally, can completely transform your next chapter.

What I Do

I help midlife professionals and explorers:

Rethink their career, business, or retirement path
Design a more intentional lifestyle rooted in values and freedom
Travel with purpose — not just for escape, but for expansion
Use miles, points, and smart planning to travel better for less
Gain financial clarity and strategic direction through advisory support

Whether through content, guides, travel planning, or consulting, my goal is simple:
Help you build a life you don’t want to escape from.

A Bit About My Background

I spent over two decades in corporate finance, most recently as Assistant Treasurer at a $4B healthcare company. I’m an MBA, a CFA, and someone who finds real joy in simplifying complexity — whether it’s in spreadsheets, business models, or big life decisions.

Along the way, I also built and marketed several digital brands, served clients as a travel advisor, and developed a passion for helping others navigate change with clarity and confidence.

A Bit About Me

I’m a divorced dad of three grown sons (hello, empty nest) — one of the greatest privileges of my life.
I’ve visited 5 continents and 30 countries (and counting) over the last 3 decades.
I share a home base with my aging parents to support them while building a location-flexible life.
I love points and miles, intentional travel, deep conversations, and the idea that life can get better with age.
And I’m a firm believer that life is short and there is much to experience.

Want To Explore?

Learn how I can help you, sign up for my newsletter, follow and engage with me on social media, comment on my posts, and contact me with suggestions or feedback.

Work With Me (consulting/coaching/travel services)
Join A Group Experience (coming soon)
Contact Us: Get In Touch Here
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Final Thought

You don’t have to blow up your life to change it.

You just need the right mindset, a little strategy — and the belief that your next chapter deserves to be your best one yet.

If you’re ready to see what your future life may hold, you don’t have to figure it out alone. Let’s make it happen together! Start your journey here.

I hope you enjoy the content I worked hard to create. If you have any suggestions for improving this site, I’d love to hear them!