Thriving on Paper but Drifting in Life

My story of taking a career break

Author

Billy Hudspith
June 02, 2025

How on earth did we end up here?

Before we begin this journey of growth, learning, and embracing life more intentionally, I want to share a bit of my story.

The best part?
It’s a story many of you will likely relate to—and I hope it offers fresh perspective, sparks reflection, and reminds you that you’re not alone.

Presidents Club 2016

Career Nutshell

I spent 12 years working as an Account Executive in Tech, across four reputable companies—the most well-known being DocuSign.

I was there for 8 of those years, across both the London and San Francisco offices, witnessing and contributing to its growth from 450 employees to over 8,000 public listed company.

Over that time, I:
✅ Hit quarterly targets in 9 out of 12 financial years
✅ Presented at events to 300+ people
✅ Onboarded and mentored new hires
✅ Helped shape a strong team culture (or at least I hope I did!)
✅ Built a great network, a strong CV—and earned well, too

To be honest, that felt uncomfortable to write. It sounds like I’m listing achievements for the sake of it.
But I share this because, on paper, it all looked great. And many of you reading this may relate—especially if you're a high-achiever surrounded by success.

So why did I still feel unfulfilled?
Why did I feel like I wasn’t truly growing?
Why, despite the external success, did it still feel like something was missing?

Time for a change.

El Chalten, Patagonia, Argentina

Why Did I Take A Career Break?

I simply wanted to travel.

I’d been fortunate enough to go on some incredible holidays over the years, but I never had that extended period of exploration. No gap year after school, and both university summers were spent in internships.

The great thing is—I don’t regret not travelling earlier. Getting a head start in my career gave me valuable experience, and to be honest, travelling at 32 was a completely different (and probably more meaningful) experience than it would’ve been at 21, when I was more focused on parties than perspective.

I also didn’t see it as a huge risk. I had a strong CV, a solid track record, and a great network. I knew that when I returned, I’d be in a good position to find the right role again.

Sometimes, the timing that feels "late" is actually right on time.

Stop brushing over the real reason Billy, what was it?

To put it bluntly, I was unhappy—and I didn’t know why.

On paper, everything looked great: a successful career, strong finances, a home, a car, multiple friendship groups, no major health issues. Life was good… so why didn’t it feel good?

Looking back, I realise it’s because everything was easy. I was living life in "safe mode"—sticking to what I knew, staying in my comfort zone, not really challenging myself. I wasn’t trying new things, meeting new people, or pushing to grow. I thought I had it all figured out.

But the truth is, I was the same person in my early 30s that I had been in my mid-20s—doing the same things, getting the same results. And that created a quiet frustration within me.

I felt like I was wasting years.
Deep down, I knew I had more to give—more potential, more purpose.
That’s where the guilt came from. Not because things were bad, but because I wasn’t evolving.

And that was the wake-up call.

Why My Story Might Be Relatable

I think so many of us feel a quiet confusion—wondering why life looks great on paper, yet something still feels missing underneath.

That was definitely me. And now, it’s what I help many of my clients navigate.

Here’s what I’ve learned—there usually isn’t one reason. It’s often a combination of subtle patterns we fall into without realising:

🔹 Reason 1: Wearing a mask to fit in
Feeling like you have to present a certain image to be accepted—whether in your career or personal life. Constantly adjusting how you show up to meet others’ expectations is exhausting, and over time, it disconnects you from who you really are.

🔹 Reason 2: Climbing someone else’s mountain
The last thing we want to be in life is selfish. But when you consistently neglect yourself, you fall out of alignment with your values—and start chasing external validation that never truly satisfies.

🔹 Reason 3: Trying to please everyone
The hard truth? You can’t. And you never will. We all have strengths, flaws, different beliefs and opinions—and trying to be universally liked or understood is a losing game.

Awareness of these patterns is the first step toward change.
You don’t need to overhaul your life—you just need to start getting honest about how you’re living it.

To Finish On A Positive

This is why I’m genuinely excited, motivated, and inspired to be launching this newsletter.

It might sound a bit dramatic—but the truth is, until we pause and reflect, until we start to feel more deeply about how we’re living, we risk experiencing life only at the surface level.

I’m not saying we need to transform everything overnight—or even that we should.

But I am saying that one intentional habit, one mindful thought at a time, can help us get so much more out of our days.

And to me, that sounds pretty cool.

Thank you for being part of this. I’m excited to grow with you.

See you next week

Billy Hudspith

Your Mindset & Habit Creator

Incase you want more!