Imagine choosing one meal to eat every single day for the rest of your life. Even if it was your absolute favourite dish or cuisine, how long would it take to become sick of it?

It’s a common children’s playground hypothetical, but its principal relates to many midlife men that are feeling stuck after decades in their careers. What used to fuel you and excite you in your work just might not be appealing to you any more, and the thought of charting your own path with a career shake-up keeps entering the back of your mind. 

However, while the itch to shift gears and change careers can be a powerful one, it’s crucial to remember to enter into this new stage slowly and intelligently. It might sound counter-intuitive, but the best strategy you have when starting out in your new career endeavour is only going half-throttle. 

The thought of pursuing a ‘side gig’ has grown rapidly over the last four years, with Harvard Business Review reporting nearly double the number of entrepreneurial endeavours among Americans since 2020 alone. It’s officially mainstream, and mid-life professionals are choosing to satisfy their curiosity with a project on the side while they continue their day job. 

For some, this might come across as a half measure, especially when a career change is currently their biggest passion. It’s easy to think this way, but beginning this pivotal moment with small steps instead of grand decisions sets you up for success down the road.

You might have the perfect plan in mind for your next steps, but before you quit your day job and buy a food truck, try running it on the weekends first. These sort of decisions are good to think of as “micro-experiments”. 

Many career development experts endorse this concept of short creative bursts that come in the form of small changes, allowing you to trial out a potential new path for your career. Even just spending 7 days testing out a new direction can answer questions in a safe and measurable way. This tactic allows you to answer the unknowns and satisfy your creative urge in a safe and intelligent way. 

But how do I know if my idea’s good enough for a side gig? How am I sure I’m not just burnt out in my current role?

These are valid questions, and ones that run through the head of anyone who considers making such a big decision as a career pivot. The important thing is to have a real conversation with yourself, and determine if the following applies to you:

• Do you enjoy the work? Would you still enjoy it as a job?
• Does your idea solve a real problem or meet a real need?
• Can it generate income or traction on a small scale?
• What’s the time commitment? And can you sustainably carve it out?
• What’s your “no regrets” fallback plan?

One useful goal to set yourself is to set up a simple success metric for your fledgling side project. Setting yourself a simple goal such as “Can I earn $500 from this in 40 days?” or “Can I reach an audience of 1000 people in the first month?” can be a useful outcome of your micro-experiments to work towards and determine if your idea is really viable. 

For some men, the unknown aspects of such a big undertaking can lead to them giving into their fears and never starting out their side project dream. It’s not an easy process to get a new ambition off the ground, but your own doubts should never be the limiting factor. 

Remember, if you start to feel like: 

“I don’t have time” – even just five hours per week starts to add up. 

“I’m too old” – your experience is a competitive advantage. 

“The market’s too crowded” – most people don’t market well. Survey the competition and stand out with professionalism. 

“It’s risky” – not if you keep your day job!

You don’t have to give up your security and peace of mind just to feel satisfied with your work. Just a few hours per week alongside your day job gives you the freedom of trying something new without the pressure of instant overwhelming success. Just think back to that food truck – if you’re thinking about making a major play, take it for a spin on the weekends first!

Feeling a change in your identity is real and a critical part of growing as a person. We all feel it – in our friends, our families, and even our careers. But like with anything, if you want to do it properly, you’ve got to do it smart. Small changes, minor projects and baby steps towards your goal gives you a foot in the right direction all while maintaining your security. 

You’ve got the skillset, the know-how, and now the tools to make something real. So, what will your side quest be?

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.