Purpose Over Wealth: A Conversation with Thomas Woodland

By Kristen Oliveri

Purpose Over Wealth: A Conversation with Thomas Woodland

Kristen Oliveri sits down with Thomas Woodland for an inspiring conversation about the personal journey that led him to create Woodland Growth—and how he’s dedicated his life to helping families transform their legacies. The discussion is rich with insights, so we’ve pulled out key highlights at the top for a quick read, followed by the full interview below. Don’t miss this powerful and thought-provoking story—keep reading!

Quick Highlights: 

“You can’t build happiness from the outside in.” Thomas Woodland shares how his journey inspired Woodland Growth’s mission to help families align with purpose.

Wealth alone doesn’t protect from suffering — it can amplify misalignment and disconnection. Woodland Growth’s flagship Key Family of Influence program guides UHNW families to build unity and purpose-driven legacies. Programs like Beyond Liquidity and Beyond the Game support founders, athletes, and celebrities through life’s biggest transitions. True fulfilment comes from “remembering who we are beyond labels, fear, and pressure.”

Looking ahead, Woodland Growth will expand with transformative retreats and Thomas’ new podcast, Woody World, bringing joy and fresh perspective to legacy planning.

Childhood and upbringing always play a pivotal role in shaping who we become. Can you share how your early life influenced the path you're on today?

I’m an only child from a well-off family, although my grandparents were working class people from Yorkshire. The men on my mum’s side of the family were cold steel rollers. My dad did very well in business and was focused on stability, security and good financial planning. So, I am the second generation of wealth. For him, success was providing for his family, living in nice homes, going on beautiful family holidays, and enjoying his boat and Porsche 911. And he wanted the same for me, a good stable job in a high-paying, well-respected industry. All very normal! 

But I’ve always been wired a bit differently. I’m extremely bright, but I’m also dyslexic and have recently been diagnosed with ADHD. Although traditional academic routes didn’t inspire me, that’s the path I followed. I loved being around people, being outdoors, being playful, being free. When I was 10 years old my parents moved to the opposite side of England and I never really settled there, so at age 13, I asked to go to boarding school. On reflection, I wanted to escape the sense of disconnection I felt. My mum was very particular about how the house was kept and there wasn’t much room for me to be a child or have friends around to hang out. That was the first time I made a dramatic change in my external world in search of something deeper — connection, freedom, a sense of aliveness. This search for deeper satisfaction in external circumstances and achievement drove the next 20 years of my life.

After high-school, I did a gap year with extremely wealthy friends, many of whom had attended Eton and Harrow. And while significant wealth was certainly there, so was a lot of pain. A lot of escapism. Drugs, eating disorders, mental health struggles. Even then, it was clear to me that wealth doesn’t prevent suffering. In fact, it often provides the means to hide or accelerate it. What I’ve come to see is that addiction, conflict, isolation are simply the symptoms and signals of a deeper misalignment; a lack of connection, purpose, joy. 

I also saw the other end of the spectrum. At University I lived with a great friend who was very close with the Royal Family, had an influential family history, and a whole team of staff at his homes in Norfolk and Westminster. While there was a formal dress code to attend family dinner at his home, he’s one of the most grounded, intelligent and kind human beings I’ve met. So, I was always curious about the differences in people and whether there was a simple way to understand how we work.

After graduating with a degree in Economics & Politics, and without a clear passion or identity, I fell into corporate finance at Ernst & Young where I qualified as a CA. Although I hated my job, I thought that if I earned more money, I would be happy. As I was also desperate to prove my worth, I set my sights on earning millions in private equity. However, I had problems of my own with partying, addictive behavior, and constantly spending more than I earned. Of course, I now understand these were symptoms of my own misalignment, but at the time I truly believed it was because I wasn’t earning enough money and that my “trust fund” friends were leading me astray. My solution to this was to make a whole new group of responsible, career focused friends by doing an MBA at London Business School, which would also enable me to secure a high-paying job in private equity.

This is when I began to sense the flawed premises that I was operating from because without the structure of my job, my symptoms got a lot worse. In denial, I assured myself that when I had the job in PE paying hundreds and hundreds of thousands a year, then I would straighten myself out. However, my worst fears came true when I started my “dream job” on the investment team of a global PE firm managing over $30 billion, and my symptoms of addiction and isolation escalated again. In a final desperate attempt to fix this, I sold my home in trendy Dalston in East London and rented a beautiful apartment in Marylebone, one of the world’s most desirable postcodes and a five minute walk from my new office in Mayfair. I thought, “this is it… I now have everything that equals fulfilment.” But none of it worked. My mental health got worse. I was miserable, and I couldn’t understand why.

Then on Friday March 3, 2017, sitting in my lovely apartment dreading the thought of going into work, I had a moment of truth. I realized that life just doesn’t work the way we’ve been told it works. You can’t build happiness from the outside in. Security, connection, aliveness all come from living in alignment with oneself. From knowing our intrinsic self-worth and acting on our interests and passions. That simple, yet profound, realization changed my life. And while I remained working in PE for a couple more years, my passion for understanding what life is all about and sharing this with others was born. 

For me, corporate finance and private equity felt like a prison. And that feeling is common for many of the next generation I now work with. They’re bright, creative, sensitive, but often burdened with shame or boxed into paths that don’t match their passions or interests. This is especially true for those with neurodivergence or different ways of thinking. So many have grown up feeling like they are a problem they need to solve.

What I’ve seen in myself, in my friends, and in the clients I serve, is that underneath the presenting symptoms, whatever form they take, is self-doubt, a disempowering identity, and a false narrative about life. Purpose and passion are totally missing. And great wealth often exacerbates these symptoms because there are just so many opportunities for escape and distraction in the external world. This is my own story. It’s the reason I do this transformative work, guiding UHNW individuals and families to discover their own origin story and creating a purpose-driven legacy that goes way beyond wealth.

What was your purpose in launching Woodland Growth and how does it tie back to your personal journey?

As I was saying before, Woodland Growth was born out of a moment of clarity about the fundamental nature of life and how most of humanity have it 180 degrees the wrong way around. I'd spent decades surrounded by friends and colleagues with immense privilege and influence, yet so many were operating from a critically low state of mind and creating a living nightmare for themselves. At work, I saw billion-dollar decisions being made from deep fear and insecurity and it led to all kinds of unnecessary conflict, dysfunction, inefficiency, poor health, even lawsuits. Not to mention, a lot of suffering.

It just felt so avoidable. And for the most part, people were oblivious to their role in it. 

They couldn’t see the true source of all these unwanted situations and results, and so huge amounts of time and money were wasted treating symptoms. Unfortunately, because the actual issue was invisible to them, it was like that game “Whack A Mole.” They might solve one symptom but then other pops up immediately. And that’s what many people’s lives and businesses are like, constant reactivity to symptoms and surface level problems. That was the story of my life, constantly searching for solutions “out there” when the only place real solutions exist is “in here”.

There was this one partner at work who was so well meaning but so burned out. He had never even been to the tropics, but somehow ended up with a tropical disease. And it was obvious it was because he was the most stressed person in the entire firm. He had to take almost a year off work to get treatment and recover. And yet there were other partners in the firm who glided around and always took the time and care to check-in with all members on the team.

Seeing this range, I became curious if pretty much everything in life and business can be explained by a hidden “harmony variable” that is independent from external circumstances. What if everything in the external world – our health, our relationships, our results, our creativity, our fulfilment – is downstream from how aligned and alive we are?

Personally, I had also experienced a total transformation. In a few months I went from depressed and isolated, to loving my life. After my initial realization I went t-total and found an amazing spin studio. I felt so alive and met many life-long friends there. Until then, I had no idea that these health focused communities even existed. And I still loved dance music and festivals, only I enjoyed these activities even more when sober. I was a far more vibrant version of myself, still the life of the party, but I’d found something deeper. I realized my life was already beautiful. I just hadn’t been present to it.

My big question was: how can someone go from depressed and addicted to joyful and loving life so quickly? What’s really going on under the surface? This inquiry led me to train as a master-level transformative coach and to immerse myself in teachings about the nature of consciousness and reality.

The core of what I have come to see is simple — we’re all infinitely creative beings living in a thought-created world. We think we’re experiencing life, but really, we’re experiencing our thinking about life. And there is an unlimited source of intelligence and wisdom that is flowing through us constantly. And when we understand and know this for ourselves (which is very different to a belief or a framework), we see through the illusion and everything in life is free to change. Our actions, behavior, relationships and results are always in perfect integrity with our thought-created identity and reality. In other words, every human being is already creating a legacy and, to ensure it’s a thriving one, this understanding is critical.

I am inspired to bring this understanding to those with the most leverage: UHNW families, world leaders, individuals with influence and followers, because they’re the ones shaping the world. The ripple effect is massive.

So, the purpose is huge: to inspire the evolution of humanity to its highest potential. And that potential is joyful, loving and abundant.

You offer a host of transformative programs for UHNW individuals and families. Can you walk me through your offerings?

Yes, absolutely. Every one of our programs is rooted in essential principles of life that when understood experientially, make everything far simpler. There are a few quotes attributed to Einstein that really bring this to life “Everything should be made as simple as possible, but not simpler” and “If you look at nature really carefully you can catch a glimpse of something deeply hidden.”

The hidden truth is that we are already creating our own reality from the inside out via thought. The great physicist David Bohm described this succinctly when he said “Thought creates our world, and then says “I didn’t do it.”” 

The great news is, we can think anything. Which means, within the laws of physics, we can create anything. Our lives, our families, our legacies. The only limitation is thought. And each individual creates their own meaning about life and everything in it: past, present, and future. 

So rather than treating symptoms we go to the source: the level of consciousness and understanding from which people are living. We have five programs that deliver this transformation.

Our flagship program is called Key Family of Influence, and it’s designed specifically for the leaders of UHNW families. We take the family through a five-step process that aligns them around a shared sense of purpose… one that’s completely authentic to their unique story, values, and history. This process isn’t just about harmony or cohesion (though that’s a natural result). It’s about unlocking a living, breathing legacy that’s meaningful to every member of the family.

The statistics are sobering: 68% of UHNWIs are self-made and only 10% of UHNW families maintain their wealth beyond the third generation. But this isn’t due to a lack of top-quality financial advice or legal planning. It’s a human issue. The families who thrive across generations are those who understand who they are, where they’ve come from, and what they stand for. That’s what we help them build: a family culture rooted in unity, awareness, and purpose.

NextGen Changemaker is a program for the rising generation within these families. Often, NextGens are quietly struggling, feeling the weight of expectation, unsure of their place, or desperate to prove themselves. Sometimes they withdraw; sometimes they rebel. Either way, they’re often disconnected from their own inner compass. This program is about helping them discover who they truly are, beyond the family name or financial status. It helps them step into a life of meaning, impact, and joy on their terms.

Another key offering is Beyond Liquidity. This was born from my time in private equity, watching founders go through massive exits only to fall apart emotionally. I’ve seen divorces happen mid-transaction, health deteriorates under pressure, and people spiral into depression after closing a deal they thought would bring freedom. This program offers both pre- and post-transaction support so that entrepreneurs can navigate the liquidity event from a place of deep clarity, alignment, and worth beyond wealth. We help them fall in love with their life before the sale and discover a sense of purpose and identity that’s not dependent on the business they’re exiting.

We also offer Beyond the Game, a version of this for elite athletes, and Beyond the Fame, for those in the public eye. In both cases, we help individuals disentangle from the character they've been playing, whether that be the athlete, the celebrity, or the founder, and reconnect with who they really are underneath it all. Because our purpose and passion aren’t something we have to invent. It’s what remains when the noise falls away.

In every program, the real transformation comes from a deeper understanding of how life already works, not the illusion of control or constant optimization, but the universal mechanics of human experience. When people understand that they’re the ones creating their reality and that their true nature is joy, wisdom, creativity, and connection everything changes.

Symptoms of misalignment naturally fall away. Indicators of health and vitality naturally appear. Life becomes something that flows again. This provides evidence that grounds them in their own experiential understanding. The world reflects their confidence, passion and purpose back to them.

I’m a total geek for all of this and take inspiration from a number of different sources that all point to the same essential truth. Each of our program guide our clients through The Hero’s Journey: the process of remembering that they are The One. That they always have been. That they’re more powerful and free than they ever imagined. And when they wake up to this, they choose consciously and act deliberately. 

Billionaires are an interesting group to study, but as you and I know, money and success don’t necessarily equal happiness or a fulfilled life. In your experience, how can people of great wealth find true fulfilment?

Regardless of wealth, fulfilment works the same way for every human being. Joy, love, and creativity are natural qualities. The only thing that ever gets in the way is thought.

That might sound simple, but if you really see it for yourself, it’s liberating. Because it means that fulfilment isn’t something we chase, earn, or construct. It’s something we remember. It’s something we wake up to. Even the language “to fall in love” points to us dropping into this state when we let go. 

What I’ve observed is the more “successful” someone is by external standards, the more thinking they often have in the way. Pressure. Control. Identity. Concern about appearances. Worry about what others think. Fear that their children aren’t measuring up, or resentment that they don’t appreciate what they’ve been given. Guilt. Shame. Endless doing. All of it is thought. All of it feels real. But none of it is who we really are.

Because who we really are is something far deeper. We are not separate. We are each a microscopic aspect of the intelligence of life that drives evolution, breathes us, pumps our hearts, heals our wounds, and keeps the solar system perfectly in orbit. And we don’t have to do anything to earn this, it’s already there. It’s who we are.

The only reason anyone, billionaire or otherwise, feels unfulfilled is because they’ve temporarily lost sight of this truth. They’re caught up in their thinking. Caught up in a world of concepts, identity, and shoulds. But underneath all of that, there’s always a deeper current. That’s what our work is about.

Every program we offer brings people back to themselves. Not the illusory version shaped by the world and our conditioning, the true self. The one that was there before the labels, before the pressure, before the performance. And when people reconnect with that and allow themselves to align with their true passion and purpose, life starts to flow again.

When you are living a meaningful life, a life that excites you, energizes you, and feels like your own, you don’t tend to get lost in drama or judgment. You’re too busy living. Creating. Contributing. Connecting. You stop scanning the horizon for threats, and start feeling genuinely grateful to be alive. That’s what we see, again and again, in our work.

Fulfilment isn’t about what you have. It’s about how deeply you understand who you are.

And once you see that clearly, once you understand the living mechanics of the human experience, you don’t need more strategies or tools. You start living in harmony with life itself. And life responds.

So yes, wealth can be a powerful amplifier in any direction. That’s why it’s so vital to cultivate the essential foundation. If an individual or family is disconnected from themselves, fame and fortune magnifies the noise. The only true freedom is internal. That’s what we help clients find for themselves.

In your view, why do so many families — even those with significant resources — struggle or fail over time?

Because they’re building their lives, businesses, and legacies on a misunderstanding of who they really are.

Many families are unconsciously living inside of an identity shaped by fear, pressure, and thought patterns they’re not even aware of. And if you’re creating from that place, no amount of money or resources can save you. It’s not a structural issue. It’s not a lack of strategy. It’s a fundamental misunderstanding of life.

Your family life, your business, your legacy – they are all expressions of you. They reflect your state of consciousness. And if you don’t like what you’re seeing externally, the answer isn’t to work harder to fix the surface issue. The answer is to turn inward, to see how it got created in the first place.

The challenge is, most people keep “picking up their thinking” about life, family, and themselves from the exact same place they left it. They live in loops. They look out at “what is” and because they don’t realize it’s just a reflection of past thinking, they reinforce it. They perpetuate it. New day, same patterns. Different faces, different places, same root. So, this is the tricky thing, because we have all built up a lot of solid evidence that “this is the way it is” and “that’s the way they are,” but most humans don’t realize they put it there in the first place and they’ve been in a loop ever since.

Ultra-wealthy families are just as prone to this as anyone else. In fact, the drama and fragmentation often get amplified by the wealth. The first generation overcomes hardship, builds character, and develops inner resilience through the journey of wealth creation. They have already been on a Hero’s Journey of sorts. But then, in an effort to protect their children from struggle, they give them everything they didn’t have and make life comfortable for them with quality education, opportunities, and money, without realizing that they’re removing the challenges and contrast that were essential to their own personal growth.

Over time, the family disconnects from its core: from shared values, from a compelling narrative, from purpose and passion. Maintaining the outer trappings of wealth, status, and privilege unintentionally become the priority. 

But the real issue is deeper. We live in a culture obsessed with financial security, material accumulation, and fear of the future. The media tells us what’s wrong. Institutions tell us what to worry about. We’re trained to focus outward, never inward. We are mesmerized and hypnotized by the “problems” in our world and exhaust ourselves complaining about them and trying to fix them. That’s the trap.

What families need isn’t more information. It’s transformation. A shift in consciousness. A deeper understanding of how free and creative they are.

That’s why we don’t offer surface-level solutions. We guide families to turn around. To look in the opposite direction from where our culture and fear-based mass media is constantly trying to get us to look. We help them operate from a state of clarity. And from that place, they’re able to align around a shared purpose and vision.

No one has to believe anything we say. In fact, we’re not asking them to. What we do is point them toward truths they can see for themselves. Because when someone catches a glimpse of how reality is created, from the inside out, everything changes. When a family embodies this clarity, the next generation also benefits. They don’t fall for the trap like most of us do. Like the Theory of Relativity and Germ Theory, I believe this is a new paradigm of human understanding that will change the world. It’s just a question of when.

As you look toward the future, what’s on the horizon — both in terms of Woodland Growth’s programming and your own personal evolution?

For Woodland Growth, the future is about scaling our impact. Our vision is to deliver all program in intimate group settings in beautiful locations around the world. Through bringing UHNW individuals and families together we aim to build a community of changemakers who are inspired by one another’s journeys, learn from the combined wisdom of the group, and collaborate to build a brighter future for humanity.

These gatherings will include world-class experts in wellness, purpose, healing, and family dynamics, and new technology. They’ll be containers for transformation and breakthrough ideas. When we bring together individuals and families who are ready to go beyond wealth, beyond fear, and beyond traditional planning, something extraordinary happens. People reconnect with purpose. They fall back in love with life. They see themselves and each other through new eyes.

That’s why we love the word beyond, because it points to what’s on the other side of achievement, pressure, and performance. This work isn’t about sacrifice and trade-offs. It’s the opposite. It’s the key to sustainingwealth, purpose, and harmony across generations. Because the real risk to any legacy is conflict and disconnection. Alignment is the greatest insurance policy a family can have.

On a personal level, I have some creative projects focused on sharing my message with the world in joyful and playful ways. I’m launching a podcast called Woody World. The name actually comes from something multiple clients have said to me: “It’s so great to be in Woody World” which is an alternate reality from the one most of us are tuned to. One where life is playful and lighthearted. Where problems aren’t problems. Where we stand for what we love, instead of against what we hate.

That’s the spirit and energy I bring into everything I do, from our family programs, to my writing and podcast, and my ultimate vision of hosting the leading US primetime talk show, something I’m totally sure and relaxed about. Whatever the form, my passion is to share my spirit and energy with the world. To demonstrate that life can be so vibrant and fun. That the contrast and challenges we experience are actually a gift clarifying what we truly want. And that when we follow what lights us up, we naturally become more generous, more loving, more impactful, and tap into life’s natural abundance.

Like Howard Thurman said: “Don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.”