Hi, I’m Olly Carter
You probably don’t need another person telling you to set bigger goals, optimise your morning routine, or simply be more grateful.
You may already be successful by most conventional measures. But if your life feels flat, disconnected, or increasingly difficult to recognise as your own, knowing what to do next can be surprisingly hard.
I understand that tension because I’ve lived it myself.
From conventional systems to a more deliberate life
I began by following a conventional route. I completed an MSc at Bayes Business School (formerly Cass) and spent my early career navigating institutional corporate and commercial real estate operations in London, including time at firms like UBS Investment Bank, Skanska, and Nelson Bakewell (NB Real Estate). From the outside, it looked like a highly successful path.
But I was also drawn towards something different: time in the mountains, travel, high-octane outdoor life, and the freedom to shape my days more deliberately.
Over two decades, my journey crossed through 91 distinct chapters spanning London, Cornwall, France, Australia, Bali, and the European Alps. I didn't just visit these places, I managed high-stakes operations within them. I ran luxury guest operations and concierge services in Biarritz with Keyweek, managed premium ski chalets in Morzine with TG Ski, directed market-leading wellness hubs in London like triyoga Camden, managed the luxury hospitality at The Retreat New Forest, and served as a high-volume corporate sobriety coach consultant for One Year No Beer (OYNB).
Some of those decisions were exciting and liberating. Others were deeply uncertain, messy, and difficult. Having navigated my own severe burnout, structural life disruptions, and profound transitions, I learned firsthand how to rebuild a human life that feels right, rather than one that simply looks right on paper.
Those experiences taught me that changing your trajectory is rarely one dramatic act of courage. It is a series of honest conversations and deliberate decisions. It is noticing when you are drifting, becoming willing to question the identity you have built, and taking practical steps towards your own raw aliveness.
It is also not about running away from responsibility or blowing everything up. A more alive life still includes work, family, commitments, and uncertainty. The difference is that you are actively participating in it rather than simply enduring it.
Why I work with men
I work with successful men—founders, partners, and high-level executives, who feel stuck, lonely, restless, or emotionally flat beneath the surface of a life that appears fine.
Many of the men I work with are exceptionally capable and dependable. They have built careers, relationships, families, businesses, or financial security. But they have lost touch with what gives them raw energy. They carry their doubts quietly, unsure whether they are allowed to want something different.
You do not need to destroy what you’ve built. You simply want to feel fully present, connected, and alive within it.
That is where existential performance coaching helps.
How I coach
Backed by three distinct coaching qualifications and a lifetime of experiential transitions, my approach combines deep transpersonal alignment with high-performance lifestyle architecture. We explore what is really happening beneath the surface, clarify what matters now, and make changes that fit your actual life, not an imaginary version of it.
We work directly on your direction, core identity, career legacy, relationships, boundaries, and capacity for play. The aim is not to create a perfect life or a perfected version of you.
It is to help you make choices you respect, rebuild absolute self-trust, and create a life that is worth showing up for.
I’m Olly Carter, and I’m the founder of Bold Living.
Ready to enter the scene?
If you are successful on paper but disconnected in practice, apply to join our selective retainer network. We will look honestly at where you feel stuck, what needs to change, and whether there is mutual alignment to co-design your container.