In this thought-provoking episode, I explore one of life’s most powerful metaphors: what happens when we realise the ladder we’ve been climbing is leaning against the wrong wall? Many of us work tirelessly toward goals we set years ago, only to discover that our values and desires have shifted along the way. Drawing from Stephen Covey’s wisdom, I dig into why achievement can sometimes feel hollow despite “doing everything right.”
I share practical strategies for pausing to reassess your direction, beginning with the end in mind, and making intentional choices that align with your true values. We’ll also explore Bronnie Ware’s illuminating work with the dying and their most common regrets. If you’ve ever felt that disconnect between success and fulfillment, this episode offers the permission and guidance you need to reorient your ladder—because it’s never too late to climb the right wall.
Chapters
00:00:07 Welcome to The Balanced Leader Podcast
00:00:48 Have you ever wondered ‘How did I get here’?
00:01:53 My own personal experience with climbing the corporate ladder
00:04:01 What can we do?
00:04:42 Visualisation: looking back on your life
00:05:42 Case Study: Bronnie Ware
00:07:01 Is it time to stop and reflect on which ladder you are on?

Welcome to The Balanced Leader Podcast, where we tackle the ultimate challenge for leaders: achieving peak performance without sacrificing your wellbeing. If you’re ready to lead with clarity, energy, and impact—without burning out—then you’re in the right place.
I’m Rob Hills, your leadership and wellbeing coach, and in each episode, I’ll give you the insights, tools and strategies that will enable you to thrive. So without further ado, lets dive into todays episode.
Have you ever had one of those moments where you stop and look at your life and ask “Hang on… how did I get here?”
You’ve been working hard, doing all the right things—meeting deadlines, chasing goals, ticking the boxes. Yet you aren’t where you thought you would be or it doesn’t feel quite right. It’s like you’ve been climbing, climbing, climbing—only to realise the view from the top isn’t what you expected.
That’s the moment when the metaphor hits: What if the ladder I’ve been climbing is leaning against the wrong wall?
I first heard this metaphor in Stephen Coveys book the seven habits of highly effective people.
It’s such a simple metaphor . But it’s one that hits deep, especially when we’re busy, being productive, ticking things off, and still feeling like something’s missing.
We live in a world that rewards speed, efficiency, achievement. We’re taught to climb—faster, higher, more. And that’s not necessarily a bad thing. But what happens if we never stop to look up? To ask: is this what I really want for me life?
Early in my own career I focused on climbing the ladder as quickly as I could. I was in the military and all I was thinking about was my next promotion and trying to get there as quickly as possible. To be honest, I’m not sure why! I think it had a lot to do with my upbringing around reaching goals, ticking off the next thing, always trying to move forward and do more and be more. It wasn’t until I was in my 30s that I really asked myself. What am I striving for? What is my end game? And it quickly became very clear to me that it wasn’t about reaching some arbitrary rank or career milestone.
And that’s why I really like this metaphor. It’s really about alignment. You can be crushing your goals, managing your time brilliantly, even feeling proud of how much you’re getting done—but if you’re not heading in a direction that’s meaningful to you, the achievement rings hollow.
And here’s the catch: most of us don’t know we’ve leaned our ladder against the wrong wall until we’re already halfway—or all the way—up.
And I don’t think my situation is unique. I think most of us have had similar experiences. In our teens or twenties, we make decisions based on what we think we should do. Maybe it’s family expectations. Maybe it’s what success looked like to us back then. We choose a degree, a job, a path—and off we go.
But then life happens. We grow. Our values shift. What matters at 20 is often not what matters at 35 or 50. But we’re so far up the ladder by then, it feels risky to climb down. So we just… keep climbing. Hoping it’ll feel different when we get to the top.
And if we’re not careful, that moment of disillusionment can creep in. You get the promotion, the house, the external success—and you think, Why doesn’t this feel better? Why doesn’t this feel like enough?
It’s not because you haven’t worked hard. It’s because the ladder’s on the wrong wall.
So what do we do about that?
Well, the answer isn’t to panic or throw everything out. It’s to pause. To create space to check in with yourself. And most importantly, to begin with the end in mind—which is Covey’s Habit 2. What kind of life do you want to lead? What really matters to you now—not ten years ago, but today?
If your answer is “I’m not sure anymore,” that’s okay. In fact, that’s actually a really powerful place to be. It means you’re ready to get intentional again.
Here’s a simple practice: imagine you’re at the end of your life, looking back. What would make you feel proud? What would make you feel peaceful? Whose lives do you want to have impacted? What kind of experiences do you want to have had?
Then ask: does the life I’m building now—this ladder I’m climbing—lead me there?
Sometimes the ladder just needs a small shift—a new project, a fresh boundary, a realignment of priorities. Other times, it means stepping back and making bigger changes. But either way, the first step is always awareness.
No one else can answer those questions for you. And no productivity hack will save you if you’re speeding up the wrong path. But when you take a breath, look up, and choose your direction consciously—then every step forward starts to feel different. Lighter. More grounded.
Because it’s not about how fast you climb. It’s about making sure you’re climbing your wall.
And if you are looking for inspiration take Bronnie Ware, for example. She spent years working in banking and administration—jobs that looked stable and respectable from the outside, but left her feeling empty. Later in life she realised what she was doing didn’t give her the meaning she wanted in her life. Eventually, she made a courageous decision to step off that ladder entirely and began working in a completely different field – palliative care. It was there, sitting with people at the end of their lives, that she heard recurring themes of regret—about not living true to oneself, about working too hard, or not expressing feelings.
If you don’t know Bonnie you may have heard of her book – The Top Five Regrets of the Dying, a book that resonated with millions around the world. If you are currently climbing the corporate ladder but feeling like this may be the wrong ladder for you, get book may help give you some direction.
So again, maybe it’s time to stop and take a look around. Take a peek over the wall and see what’s waiting for you on the other side. And if it doesn’t align with who you are becoming, start looking for another ladder. And it’s never too late? People make big career changes in their 50’s, 60’s and even 70’s.
We only get one life and I don’t want you to end up like the people interviewed for Bonnie’s book wishing they had climbed a different ladder.
That’s it for this weeks episode! I hope you have found this useful and this helps you reflect on your own situation and where you are heading.
Have a great week and I look forward to speaking with you next time!