Hi Reader,

If you're worried about trying to escape your 9-5 because you're late in your career, I'll make it really simple:

Don't be.

I left my 9-5 after more than two decades in my career. I was in my mid-40s, on my career ladder, with more rungs to climb. It took me four years to build and execute my exit plan, but I succeeded and left my 9-5 behind.

I'm living proof that it's possible.

But everywhere I go (in person and online), I hear people say it's too late for them to pivot. They tell themselves some version of the same story: that they’ve invested too much time to change direction now, taking a risk at this stage would be irresponsible, younger people will always have the edge, or that they’d need to go back to school and start from scratch.

None of that is true. However, I understand where these beliefs originate from, because I subscribed to them myself for several years. In fact, these were the same scripts that replayed through my mind until I finally decided that enough was enough.

So, if you're facing a similar struggle, allow me to dispel four myths about late-career exits.

Myth #1: "I'm wasting all of the education and experience I've built up over time."
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​Reality: You’re not starting over. You’re repositioning.

Skills such as communication, good judgment, leadership, problem-solving, and industry knowledge, just to name a few, transfer far more easily than people realize. Mid- and late-career professionals aren't beginners. They move faster because they have experience.

Frankly, you might be wasting that hard-earned experience if you don't use it to your full advantage!
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​Myth #2: "I can’t afford to take the risk now."
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​Reality: What's actually increased is your awareness of the risks. People in their 40s tend to make smarter, more informed moves.

You understand the bigger picture of cash flow, downside risk, and contingency planning. That puts you in a better position than people in their 20s. Even though the stakes may be higher, you know enough not to be cavalier about a big career change.

And that will serve you well.
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​Myth #3: "I’m competing with younger, hungrier people."

Reality: The rules are different outside of the corporate world. Most people assume that youth equals advantage. This is true to a degree in the corporate world, where ageism is prevalent.

But outside of that, most opportunities aren’t won by raw hustle. They’re won by reliability, clarity, and trust. Clients, partners, and employers prefer someone who is experienced and can manage themselves.

Myth #4: "I need to go back to school or retrain completely."

Reality: Absolutely not!

When I pivoted from bank manager to financial writer/editor and coach, I was reusing 70–80% of my existing skills, and adding a few (critical) new ones.

Please, please realize that going back to school is likely the most expensive, longest way to learn the skills you need. You need results, not more letters behind your name.

When I started my side hustle, I learned almost all the skills I needed by watching YouTube videos. In fact, if you're strategic, I think anyone can gain more marketable skills in a few months on YouTube than they'll get from most four-year degrees.

The bottom line?

Being late in your career doesn't handicap your exit plans. With your experience, risk awareness, reliability, and resourcefulness, you can proceed with the assured confidence that younger employees can't grasp.

Best,

Colin

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P.S. If you're reading this, and you're thinking, “Okay… but what should I actually do?”

Start with my free Side Hustle Quiz.

In two minutes, you’ll learn which type of side hustle or business (e.g., freelancer, consultant, ecommerce, local business owner, etc.) fits you best, and what to focus on first.

No fluff. Just clarity.

👉 Take the quiz here​

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