When Success Stops Feeling Like Success
On walking away from Silicon Valley, the NFL, and a big life - to create something smaller, simpler, and more beautiful.
Hello lovely readers,
Today I wanted to share a little more of the story behind The Whiskey Porch - how I arrived here, and why this work matters so much to me.
And it begins with a simple question:
When no one else is looking, how do you define success?
How will a life well-lived look to you when you’re reflecting on your life’s journey?
These are questions I glossed over for a really long time.
Because from the outside, my life looked full - busy, exciting, and by most standards, extremely successful. But somewhere along the way, I found myself on the wrong side of that equation.
It was a wake-up call I didn’t see coming - but one I’m deeply grateful for, because it came early enough that I still had time to choose differently.
What followed were some of the hardest decisions I’ve made. Bold shifts. Letting go of a lifestyle that looked right on paper, but didn’t feel like me. Learning to trust something deeper than logic.
I don’t share this story often.
But it’s at the root of who I am now - and why I do the work I do here at The Whiskey Porch.
I spent decades working in fast-moving, high-performance environments.
Leadership roles first in Silicon Valley, where the pace never really let up. Start-ups, the dot-com boom. And then the bust. Everything was measured, driven, and constantly in motion.
In the middle of that, my personal life took a sharp turn.
I made the decision to leave my first marriage with very young kids and start over - something that required more risk, resilience, and courage than I can easily put into words.
Over time, I rebuilt - a new life in Arizona. A career with the NFL in strategic planning. A beautiful, spacious home in Phoenix that checked all the boxes. From the outside, it looked like I had found my footing again - strong, stable, successful.
But underneath it, something still didn’t sit right.
The life I had built worked. The kids and I were thriving. It looked the part. But it didn’t feel like home anymore.
Being a woman in a leadership role in the high-stakes, big-ego world of the National Football League was, by most measures, an accomplishment. It wasn’t a path I had set out to pursue - and to be honest, I wasn’t even a professional sports fan.
As a finance executive, my work spanned everything from player salary cap strategy to ticket pricing, and even navigating a league-wide player lockout. The stakes were real - lots of zeros and commas. And the pressure was intense and constant. Did I mention the politics?
At home, life as a single mom with my young twins was full and happy - they were my world. I had no regrets.
But over time, it became clear that my professional work itself wasn’t meaningful to me - not in the way life should be. The politics, the posturing, the scale of it all - it was real. And so was the stress, the pressure, the intensity I felt in my bones.
I found myself craving something entirely different. Fresh, cool air. Time with my hands in the dirt. Big trees for shade. A life that felt rooted - connected to place and to people. A place where I wasn’t defined by my career, or moving through the world mostly anonymous.
My now-husband and I began spending more time exploring the mountains and small towns of northern Arizona.
With some hesitation we started talking about what it might look like to step away from the pace and scale of city life and corporate careers.
That’s where something shifted. It was the first glimpse of what home could feel like.
At first, these occasional day trips north into the mountains of Arizona, were an escape - just to breathe the cooler air and spend a day among the ponderosa pines.
Prescott drew us in: historic streets, tales of Wyatt Earp and the wild west, old cottages, and a slower rhythm that felt worlds away from the pace of the city. What started as a simple getaway slowly became something more.
Then one weekend, almost on a whim, we walked through a small, overgrown and decidedly neglected 1924 Craftsman bungalow tucked beneath the old alligator junipers.
It was in pretty bad shape, but something about it felt right - many things, in fact.
The next day we made an offer - less out of careful planning and more out of a heartfelt instinct we couldn’t quite explain.
Looking back now, 16 years later, that little bungalow was the first real step toward the life we were searching for.
(If you’re curious, I shared the full story here - We Accidentally Bought a Bungalow.)
At first, the idea felt almost whimsical - that we could truly shift our lives. Downsize. Simplify. Step away from the pace and scale of the big city and corporate careers without disconnecting from the world.
What I know now is that it’s not a dream at all.
It’s a decision. A series of very real choices made over time, with intention. And when those choices align with what matters most, the result is a life that works elegantly. And comfortably.
Living this way has reshaped how I see home, design, and the rhythm of everyday life.
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A house isn’t truly a home without a garden. Home and garden are not separate spaces - they’re part of the same living space, shaping how we move through each day.
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Beauty isn’t found in trends or rare, exciting moments. It lives in the everyday. Beauty is a necessary part of a meaningful life, and worth creating and seeking out.
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Smaller does not mean less. Thoughtfully designed small-not-tiny spaces are often more functional and enjoyable than the square-footage-impressive houses we used to think we needed.
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And slower living isn’t about withdrawing or a boring lifestyle. It’s about engaging with it more fully. Doing more of what you’re most passionate about. Not doingless. A more intentional pace brings depth and meaning to the ordinary days that ultimately make up most of life.
I’ve been shaping spaces for as long as I can remember.
My younger brother used to joke that I was born with graph paper and a drafting table in my mind.
It’s a little ironic that I spent much of my career designing systems and strategic financial plans, because in every spare moment I was working with spaces instead - inside and out. Remodeling homes, planning gardens, sketching ideas, imagining how a place could feel better to live in.
By the time I officially started The Whiskey Porch in 2019, I had been a designer, artist, and creator for most of my life. But that was the moment I chose to turn those instincts into a business - to help others create spaces that reflect how they truly want to live.
Writing came naturally alongside the design work.
What began on my website blog eventually led me here to Substack, where the conversation could grow into something more like a community. Because over time I’ve realized that what I do isn’t just about designing spaces - it’s about a way of seeing the world.
Home, garden, beauty, and everyday living are all deeply connected.
Helping others create spaces that feel personal, functional, and full of life is one of the great privileges of my work. It’s a gift to spend my days bringing a little more beauty into the world - and into the lives of the people I work with.
I just turned 60 a few weeks ago. I’ve learned so much, and come so far.
Life’s never been better. And the future never more exciting.
When I look back now, the definition of success that once seemed so clear has changed completely.
For me, a life well-lived isn’t measured by titles, seniority, salary, pace, or scale anymore. It’s measured in simpler ways - in the feeling of being rooted in a place that truly feels like home, in meaningful work, and in beauty woven into the everyday.
So, my question for you now is this: When no one else is looking, how do you define success? What will a life well-lived look like when you’re reflecting back on it?
I suspect the answers are very different for each of us.
But asking the question may be the most important step of all.
Thank you, for being here and being part of this journey.
With contentment & possibility,
P.S. I’d love to hear your answer to the questions in this letter☝🏼. You’re welcome to share in the comments if you feel like chatting.