There’s a moment on the golf course that Natalie Freeman knows well: the one where you stand at the tee box, club in hand, the whole fairway stretched out before you, and there is absolutely nothing between you and that ball except everything you’ve learned and everything you are. No shortcuts. No comparisons. Just you and the course.
For Freeman, that moment isn’t just a golf metaphor. It’s a philosophy she’s carried across every dimension of her life: as a single mother, a financial investment advisor, a podcast host, and a woman who, four years ago, made a decision to pursue something she’d never done before.
“When you step up to the tee box,” she says, “it’s your stance, your swing. You take a deep breath, you put into it all that you’ve learned, and you just go for it.”
That clarity didn’t come easily. It was forged through transition, through reinvention, and perhaps most unexpectedly, through eighteen holes.
The Game That Found Her
Freeman, who is based in Tampa Bay, Florida, came to golf the way many women do: not through a childhood at the country club, but through a turning point in life. About four years ago, she was navigating a major professional pivot, transitioning from running her own tax and accounting business into the world of investment advising, a move that carried with it all the anxiety, excitement, and uncertainty that comes with starting over.
“Where I thought I knew everything about everything I knew about, when you start over, even if it’s another self-employed venture, you’re literally starting from square one,” she reflects.
Golf arrived right in the middle of that recalibration. And it did what the game has a quiet way of doing: it got her outside, it connected her to people, and it offered something she hadn’t fully known she was searching for. Freedom.
“When you’re up on the golf course, you can literally disconnect from the world,” she says. “Just with the landscape, the beauty of the course, a beautiful day. Sometimes you see wildlife out there.” That kind of stillness, rare and restorative, became the foundation of a more intentional life. One she describes not as something she stumbled into, but as “divine design.”
But the golf course wasn’t the only place Freeman was doing the work of reinvention. Around the same time, a global pandemic brought the rest of the world to a halt and, in doing so, handed her a microphone.
Born from a Pandemic, Built on Purpose
When COVID-19 shut down the world in 2020 and her son was away at school, Freeman found herself alone, and like so many, contemplating the bigger questions. One of them was personal, candid, and ultimately catalytic: Why am I still single?
“I looked at my life, I’m a bit cute, intelligent, and I said, ‘No, really, why am I single?'” She laughs, recounting the moment with her signature self-awareness. “And then I thought, if I’m sitting here contemplating this, probably other singles are too.”
She started reaching out, directly and genuinely, sliding into people’s DMs and asking the real question. The responses astounded her. Men and women, candid and vulnerable, sharing their honest reflections on love, independence, and purpose. The result was the Successful But Single podcast, a platform built not on the premise that singleness is a problem to be solved, but that it is a season to be fully inhabited.
“Single doesn’t have to have a negative connotation,” she says. “It can be a play on words. Successful but single means I’m successful, but I’m not going to stop living my life. If a partner comes, fine. If not, fine. Boss first, bae later. Or not. You decide.”
The podcast has become, like the golf course, an unexpected connector, building friendships, expanding her network, and introducing her to people across the country she would never have otherwise met. And at the center of both is the same conviction Freeman keeps returning to: a full life is built on showing up fully, as yourself, wherever you are. Nowhere has she lived that lesson more completely than in motherhood.
Motherhood, Hole by Hole
Ask Natalie Freeman about the parallels between golf and motherhood, and she lights up with the energy of someone who has thought about this deeply, because she has.
She has been a single mother for most of her son’s life. He’s 22 now, and she has raised him nearly on her own since he was eight years old. The journey from boy to teenager to young adult required, as she puts it, “different levels of mothering,” with each phase its own terrain, its own set of hazards, its own demands on her patience and wisdom.
“Motherhood doesn’t come with a rule book,” she says. “And even if you get guidance from another mom or your mom or society, your child is completely different than most. You are a completely different person from most.”
She pauses, then draws the parallel with characteristic precision.
“That’s no different than life on a golf course. You may know the basics of golf, but every course is different: different elevations, different handicaps, different bunkers and hazards. And you have to navigate that, literally, hole by hole.”
Hole by hole. Day by day. Situation by situation. It’s not a formula; it’s a practice. And like any great round of golf, the goal isn’t perfection; it’s showing up with focus and playing to the best of your ability, every single time.
“You still got to show up,” she says with a laugh. “You show up to play. You know what you know, and you put it to the best of your abilities, and then you hope for a good outcome.”
Showing up, she’ll tell you, also means resisting the urge to measure your round against everyone else’s.
Your Race, Your Pace
Among the many life lessons Freeman has drawn from her time on the course, perhaps the most liberating is the one that took her longest to internalize: it’s not a competition against anyone else.
“We have a misconception,” she says. “Yes, you can play in tournament play, in a foursome or doubles. But ultimately, it’s you against the course.”
She borrows a phrase from her other sport (she’s also an avid runner) to make the point: your race, your pace. In a world saturated with social media comparisons and cultural pressure to measure yourself against everyone else’s timeline, that idea lands with particular weight.
“We want to look around at the Joneses,” she says. “‘Oh man, I went to college late, or my business isn’t as successful, or I’m a horrible parent.’ We compare so easily.” But the moment she stopped measuring herself against others on the golf course, something shifted. Her anxiety eased. Her enjoyment deepened. Her game improved.
“The sooner I learned that it’s me against the course, the more relaxed I got, the more I started to enjoy the game. And that’s life.”
It’s also how she approaches running her financial firm, Freedom Financial Consulting, where she works with investors and business owners to build and scale their financial futures. The advice she gives her clients mirrors what the fairway has taught her: start where you are, focus on your own course, and trust the process. And while you’re doing that, she’s quick to add, don’t walk the course alone.
Get Yourself a Caddy
Stepping up to the tee box with confidence doesn’t mean walking the course without support. Freeman is emphatic about that distinction.
“Life is not made to be lived alone,” she says. “In every situation, whether it’s business, whether it’s motherhood, you can only be as successful as the skills you develop and the team you surround yourself with.”
She points to the most storied players in the game as her evidence: the world’s greatest golfers are never truly solo on the course.
“Look at all the great golfers. The pros? They always have a caddy beside them. And it’s not just about holding their bag and walking the course. They’re reading elevations, talking about distance and club selection and wind conditions. That’s the same as life.”
Her advice to any woman hesitating to try something new, whether golf, investing, a career pivot, or a new chapter of motherhood, is to find her equivalent of a caddy. A coach. A therapist. A mentor. A community of women who are playing the same game.
“When you get those people in your corner and develop a few skills under your belt to cope with the difficulty, it reduces your anxiety,” she explains. “People are more confident when they become educated about something. And if you practice those skills every day, it’s like exercising a muscle. You won’t develop a six-pack today. But over time, you build.”
That building, over time, is exactly how Freeman thinks about the other investment every woman stepping onto the course should be making alongside her game.
The Green Is Worth More Than You Think
Freeman doesn’t separate her financial work from her personal mission, and she doesn’t separate the golf course from either. As an investment advisor, she’s watched the game open doors that no business card or networking event ever could, and she wants every woman on the course paying attention to what those doors are worth.
“In the next ten years, there’s going to be a great wealth transfer,” she says. “Not just from baby boomers and business owners retiring, but a lot of those assets and resources are going to transition to women. Because women tend to live longer.”
Her advice isn’t complicated, but it is urgent: start now.
“You may not feel like you’re wealthy or have enough assets to invest, but start becoming knowledgeable. That’s financial literacy.” She pauses for emphasis. “Learn what tools are available to help you position yourself, whether you have a thousand dollars or a hundred thousand or multi-millions, because you have to acquire the skills to manage that money, not just today, but tomorrow.”
It’s a principle that lives comfortably alongside everything the course has taught her. The goal isn’t to be perfect. The goal is to understand the terrain, respect the game, and commit to getting better.
“Start with where you are and build from there. Over time, it will grow, if you steward it well and understand the tools you have to reach your goal.”
She’s seen that growth play out on and off the course. She remembers one moment with perfect clarity: April 15th, the single most stressful day in any accountant’s year. For years, that date had meant long hours, client pressure, deadline anxiety. Then, on one pivotal April 15th, she found herself standing on a golf course instead.
“I knew that was a pivotal moment in my life. I knew I had made a great decision to pivot to the next.”
Since then, the course has opened doors she couldn’t have planned for: speaking engagements, business connections, resources for the veterans she’s passionate about supporting, introductions to people who could help her son’s artistic career. When asked to put a number on the return, she doesn’t even try.
“Invaluable,” she says. “If you take the time to invest in people out there, really invest in them, you will have an amazing experience that can take you so many places. I cannot begin to quantify it.”
The Legacy Beyond the Fairway
As the conversation turns toward what she hopes her son takes away from watching his mother build this life, the discipline, the reinvention, the joy, Freeman answers in three parts. Clean. Deliberate. The way she plays.
“Number three: nothing is handed to you. You must work three times as hard, be three times as focused, three times as dedicated.
“Number two: there will always be a dichotomy of life. You can see the glass half empty or half full. Golf has helped me see it both ways, and share that with him.
“And number one: we only have one life. Live on purpose, in purpose, every day. You only get one shot. And if you don’t take it, you will miss out on great opportunities, great life lessons, and just living the best life ever.”
She pauses. The way she does before a swing.
“One life to live. Live it to the full.”
Natalie Freeman is a financial investment advisor and founder of Freedom Financial Consulting based in Tampa Bay, Florida. She is also the host of the Successful But Single podcast. You can find her on Instagram at @freedomfinancial.consulting and listen to her podcast on Apple Podcasts.
This feature is part of The Green’s Ladies Golf Club’s 2026 Mother’s Day Series, celebrating women who are redefining what it means to play the game, on and off the course.
Financial Disclaimer: The financial perspectives shared in this article are those of Natalie Freeman and are intended for general informational and inspirational purposes only. Nothing in this article constitutes personalized financial, investment, or legal advice, and should not be interpreted as such. Readers are encouraged to consult a licensed financial professional regarding their individual financial situation, goals, and needs before making any investment decisions. The Green’s Ladies Golf Club does not endorse or guarantee any financial products, services, or outcomes mentioned herein.
