When considering 1:1 coaching, the biggest hesitation usually isn’t whether you want to change – it’s the fear of what that change will cost you. How do you handle financial responsibilities, let go of status, and step away from the security of a corporate ladder?
Real coaching isn’t about telling you to “take a leap of faith” into an abyss. It’s about de-risking your transition emotionally, financially, and psychologically so you can make sustainable moves.
In this client breakdown for Coaching Fundamentals, we look at how shifting core mindsets, from “more inputs equals more outputs” to playing the long game, allowed Bryan to step into entrepreneurship and feel like himself again.
1. What prompted you to start coaching with Natalie?
I spent six years in management consulting — a high-stress career of constant travel, late nights, and weekend work. I entered the industry straight out of university, drawn by the security of a high-paying job with a strong career trajectory. I had always wanted to start my own business and take the path of entrepreneurship, but for financial security, I chose to build a corporate career first to stabilize myself.
After six years, and after many changes at a company I had grown to love, it was time to explore the next opportunity. But many fears kept me from taking the step — financial fear being the biggest. I didn’t believe I could make it outside of the career and expertise I had spent years developing. There were so many unknowns, and by then, so many responsibilities: an upcoming house mortgage, supporting my parents, and keeping up with the lifestyle I had built. I was fearful of what the next step might mean for all of these.
In my heart, I knew that entrepreneurship would require sacrifices in the short to medium term in exchange for longer-term rewards. I feared the J-curve — the period where you have to invest time, effort, and money into building a successful venture before it pays off. I worried that this would cause real discomfort, not just for me, but for the people around me. And yet I also knew this was a journey anyone who wanted to build a successful business had to take. I had to bridge the emotional gap between what I wanted and what I was actually feeling and thinking at the time.
I was feeling lost when I started seeing Natalie’s posts on Instagram, and I followed her Telegram channel. After months of struggling on my own with what to do, I finally decided to reach out to her.
2. What are the two to three most significant things that have shifted since working with Natalie?
First: letting go of the belief that everything rested on my shoulders. I used to feel that without my intervention, many of my personal responsibilities would fall apart — especially supporting my family financially and providing them with a certain quality of life. But part of me was too proud to even have the conversation with them: to ask whether a few years of reduced support would be realistic and acceptable while I embarked on this path.
Second: unlearning “more inputs equals more outputs.” I used to live by the phrase “if you’re not growing, you’re dying” — something we said often in consulting, and something hustle culture makes us believe. But not all inputs are the same, and not all growth is good. You can easily grow in the ways of the world — successful in other people’s eyes, especially financially — while lacking in the areas where you actually want balance. My corporate life was a constant ping-pong between extremes: after every period of high stress, I would proclaim that I had to find an exit, that this was it. Then the promotion would come, the bonuses would be handed out, and I’d tell myself I could do this for a couple more months. The cycle repeated ad nauseam.
Third: releasing the belief that “if I don’t control it, things will go wrong.” I carried a level of responsibility and self-blame for anything that went wrong, and a need to micromanage and control situations that were sometimes two or three steps removed from what I could truly influence. My typical response was to work more and try to anticipate everything — which in the end meant being fearful of taking action and moving forward. What I’ve learned instead is to focus on what is genuinely within my control and influence today, while still taking care of the long game.
Underneath all of these was one core mindset shift: the ability to look beyond the short term. Life is played in the long game — the concept of infinite games. There is no key promotion to hit and no performance appraisal in real life. It’s an ongoing marathon that requires the player to keep playing, keep improving, and bring others into the game to play as well.
These shifts are what allowed me to first embark on this entrepreneurship journey and start my own company — but more importantly, to stay in it without struggling and burning out. I used to have no real personal boundaries; I only knew how to attack projects at 110%.
But a marathon requires the runner to move at a comfortable, sustained pace in good form — not to gas out early by sprinting the first stretch and never finishing the race. This is a seven-to-ten-year game, not a six-month-to-one-year one. That is a very different perspective to hold.
3. What would you say to someone standing at a similar crossroads?
First: it is never easy. It is meant to feel difficult, as with any change that is meaningful. The path they took to reach their current success — the one they’re so afraid to let go of — is one they’ll have to walk again, in some shape or form, to get somewhere new. It’s like going on a hike and only ever climbing one mountain. At first, the satisfaction of this one view is enough, but you get curious about other peaks and views. However, you hold yourself back from exploring because of how much you struggled to get here in the first place. You also doubt if another peak would be worth it. But the key here is not to chase the satisfaction of the view, but the adventure of the climbing process itself.
Second: although it is hard, they don’t have to do it alone — and they shouldn’t try to. It can take an entire village to support someone on a journey like this. And if friends and family aren’t enough, there are support systems out there — people like Natalie — who can give you the nudge you need to make the leap. For most of our careers, most of the planning is done for us: our bosses tell us which milestones to reach for promotion, which KPIs to hit. In this journey of life, the same hardly applies and we often feel lost.
Third: there are many ways to transition from one stage to another. I used to feel like it’d be an amputation — cutting off a limb, writhing in pain, becoming disabled. But there are many ways to make the transition gradual and manageable, and de-risked — emotionally, financially, psychologically. Those fears are what’s actually holding us back. But for me, the fear of reaching the end of my life in despair over my dead dreams was worse than the discomfort I’d feel in the process.
So I wouldn’t just tell them to “trust the process” and “take a leap of faith” — that’s very difficult to do. The imagery of jumping into an abyss is terrifying for anyone. It can be a gradual approach, like entering a cold swimming pool – first getting wet with a quick shower poolside, then submerging your body gradually. You don’t feel that cold shock as much and skip the intense shiver.
In practice, this means investing more time and effort into planning and acting instead of fantasizing in one’s head. Call out the real fears and obstacles holding us back, and tackling them one by one. Comforts, pride, status, lifestyle. Borrowing a concept from chemistry, it’s about lowering your ‘activation energy’.
4. Where are you now compared to where you first started?
“I feel like myself again.”
To explain this a little more: one core value I had forgotten was my desire for freedom — to not be encumbered, and to create and do work that I love. Solving for money and all the other worldly things remains the challenge, but the structure of how I’m living my life now is far more aligned.
I no longer chase financial goals for personal or material gain as much as I chase them to be able to play the game longer and bigger. The same things that drew me to video games in the past are now what drive my everyday energy, my direction, and the things I’m building.
Want to see the real impact of coaching with Natalie and Neverdrift’s programs? Explore more client experiences on our Reviews page.
