The Surprising Joy of Starting OveRemember your first job? Maybe you were pushing a mop or dunking fries in bubbling oil, wearing a brand-new scratchy uniform that didn’t quite fit right. It was completely new, and maybe even a little bit scary, but you were buzzing. Now? You are years into your career, you’ve built up a network and a solid reputation for yourself, but now you might feel like you’re missing that buzz you felt on day one. It might not be the minimum wage you’re longing for, but instead that beginner’s energy. 

It might have slowed down over time, but it hasn’t gone away. It’s still out there, waiting for you.  All you have to do is chase something new. Once you’ve decided to make that decision, the final challenge is staying motivated, sticking to your guns and staying the course. That’s where we come in. 

Your Brain’s Secret Agenda

Now stay with me, but let’s turn to the world of neuroscience just for a second: if you’re lost as to exactly why you’re feeling the need for a career pivot, it turns out there’s a physical reason for wanting a challenge, especially when you suck at it.  Let’s break down why this might be, thanks to neuroplasticity (don’t worry, there’s no quiz). Neuroplasticity is our brains’ ability to develop new neural pathways and skills at any age, and contrary to popular belief this continues well past childhood into our adult life. You might have felt that your brain has stopped growing, when it has been stuck on cruise control. 

Neuroscientist Andrew Huberman suggests that making mistakes in a new environment is a crucial way to kickstart your brain into forming new pathways, and thereby creating new skills. As a result, putting yourself in new environments, such as a new career or a fresh hobby, is a neurological necessity for longevity and resilience. This is a period of opportunity! Maximise your potential while your brain responds to the challenge. 

So, you’re afraid to look stupid. 

Of course, no one enjoys the feelings of helplessness that comes with being a beginner. Back then, it wasn’t fun being the new guy that doesn’t know anything, and it still isn’t today. After potentially decades in your current career path, you’ve got things figured out, and you might feel at the top of your game. Even if you are feeling that itch to try something new, to become a rookie again, crossing that barrier of embarrassment and discomfort is much easier said than done. 

Here’s the good news: that discomfort you’re feeling is an indicator of growth, of developing new skills and strengths. If you’ve ever lifted weights, you know that the moment your muscle feels uncomfortable is the moment the growth starts to happen. That’s not meant to minimise the pressure you might be feeling, but to assure you that it means you’re on the right path. The journey of starting over in a new direction can be a fulfilling, surprising and exciting one, but only if you embrace it. 

Leave your ego at the door. 

In an interview with Ageist, entrepreneur Chip Conley discusses how middle-aged men need to “learn how to become a beginner again and have a growth mindset” to succeed in their career transitions. It’s a tough thing to achieve, but the number one key to success for starting over once again is to let go of that “I should know this” voice. 

By now, you’re probably used to being the guy with the answers. This is often a great position to be in – until it starts to feel restrictive. When you’re starting out in your next career pivot, it can be off-putting to feel like you no longer have the answer to every question, or that you don’t always know what the next step is. It can be a major shock to the system when that sort of change happens, but that’s totally okay. 

The biggest mistake you can make is fighting against it and pretending to be totally across every issue you come across. That isn’t confidence, it’s delusion. True confidence in a beginner is a man that knows his weaknesses and his strengths, and understands when it’s time to say, “I’m ready to learn”. 

The Challenge of Bad

As you embark on this new journey, your years of expertise in your previous fields might fight against the new experiences that come with being a beginner. Here’s where the real challenge begins – allowing yourself to be bad! Try the thing that scares you, not just because it’ll look good on a CV, but because it gives you that same rush you’ve been missing. You might be terrible. You but you will be better for it. 

You’ve spent decades being an expert; now is the time for amateur hour!

There’s a reason the podcast Don’t Let the Old Man In resonates with thousands of men in their 50s. It speaks to the quiet war many fight against obsolescence, irrelevance, and a determination to navigate life’s crossroads with clarity and confidence. And likewise, if you’re reading this, you haven’t given up. You’re still curious. Maya Angelou once said, “If you’re always trying to be normal, you will never know how amazing you can be.” Midlife career change isn’t about being extraordinary. It’s about being aligned—with yourself.

Osh O’Sullivan is the Editor of the Don’t Let the Old Man In podcast. Listen on YouTube, Apple, Spotify or wherever you tune in. Find more thoughts on living gracefully (and disgracefully) in the second half of life at The Wisdom Vault, on LinkedIn, Substack and even (!) Instagram.r