Side Venture—Journey from Corporate Captives to Midlife Mavericks

Today, I want to discuss something I've been increasingly passionate about helping Corporate Captives break free and become Midlife Mavericks.

A number of you might already know that I’ve started working with what I call corporate captives—executives or owners of second and third-generation family businesses who have reached a point in their lives where they’re earning good money, they’ve built a career, and yet, something is missing. They’re asking themselves that age-old question: Is this all there is?

Society lays out a clear path for us. We go to school, maybe university, build a career or a business, get married, have 2.3 kids, buy the house with the white picket fence, park two cars in the garage, and life is supposed to be wonderful. But by the time we hit our late 30s and into our 40s, people have traditionally faced the so-called midlife crisis. It’s a term that’s been around for ages, and it typically hits around 40.

Why does it happen? Because at 40, you’re nearing the point of becoming, if you’re not already, an empty nester. The kids are no longer driving your decisions. You’ve likely spent a decade or more building your career, maybe neglecting relationships with the people who matter most. You might confuse working hard and long hours with caring for them, but deep down, all they want is you—your time, your presence.

Or, maybe, you’ve reached a stage of self-realization. You look at your work, and it doesn’t light you up anymore. Maybe you’re bored. Maybe you feel like it’s pointless. Or maybe, it’s even starting to feel a bit grubby. There’s a void there—a feeling that something’s missing in your work life. And this void can spill into your personal life as well. Even if work is okay and you enjoy it enough, your personal life might be where the itch lies—the itch you can’t quite scratch.

So, what do you do? You need to decide where this void is, and then figure out how to fill it.

Now, let’s talk about Midlife Mavericks. A Maverick is someone who stands up or goes against the generally accepted norms of society. I’m so taken with the idea of being a Midlife Maverick that I’m starting a community around it soon.

A Midlife Maverick is someone who reaches that stage in their career, and maybe even their personal life, where they start asking, Is this all there is? They’re searching for answers to what more life has to offer.

Here’s the philosophy I subscribe to: If you’re a corporate captive, and work isn’t lighting you up anymore, and you’re growing increasingly anxious about getting that dreaded tap on the shoulder—being told you’re surplus to requirements—there’s a better way to respond.

Instead of throwing the baby out with the bathwater and making a drastic move—like many corporate captives I’ve spoken to who’ve just had enough, taken the redundancy, and left—only to find themselves six weeks later still feeling unhappy and unfulfilled, you should consider a different approach. Don’t buy yourself another job (because let’s be honest, that’s what a franchise often is). Instead, look into starting a side venture—not a side hustle.

A side hustle is just more of the same: more money, more work. But a side venture is different. It’s a business—a real business—that you start running alongside your day job. It does a couple of things. Yes, it should generate income, but it should also scratch that itch, develop a skill, or solve a problem you see.

Because you’re employed and have a steady income, you don’t have to quit your job. You can build your side venture gradually. If after three months it’s not what you expected, you can let it go and try something else. But the goal is to create a side venture that not only brings in money but also brings you joy and fulfillment. Eventually, if it grows enough and you feel ready, you can take that redundancy, exit your day job, and focus on what truly lights you up.

Too many people get stuck as corporate captives and then make drastic decisions. I see this with second and third-generation business owners as well. They feel trapped on the hamster wheel and dreadfully unhappy, so they sell the business without identifying where the void in their life truly lies.

Is it something in the business that could be fixed by delegating more? Or is it something in their personal life—a skill they want to develop, a hobby they want to return to, or maybe even going back to school?

The key point here is that a Midlife Maverick doesn’t just accept the life that society promised and keeps doing the same thing forever. A Midlife Maverick smartly responds to feeling unfulfilled by setting up a side venture that not only generates income but also brings a sense of purpose and fulfillment.

So, where are you right now? Are you a corporate captive, feeling trapped in the hamster wheel? Are you a second or third-generation business owner feeling the same way? Or have you already started your journey toward becoming a Midlife Maverick, breaking free, and living life on your terms again?