Strategic Isn’t Creepy: Owning Your Next Move After 40

It feels like every article I write is just me giving myself a pep talk in public. Maybe you know the vibe: “Dear Future Me, please get your act together.” This week’s not-so-subtle reminder?

Being strategic with your career isn’t creepy. Seriously. It’s just smart.

The “Creepy” Myth

Let’s get one thing out of the way: Being deliberate about your trajectory isn’t slimy, or Machiavellian. It’s just… necessary.

If you’re not steering the ship, who is? Drifting is rarely a good life strategy.

The biggest advances I made in my corporate career happened when I decided to get purposeful about what I wanted, who I learned from, and what I went after. I know, not groundbreaking, but tell me: When’s the last time you consciously mapped out your next step?

Try this:

The Trap of Complacency (a.k.a. Aging Out of Ambition)

Here’s a weird side effect of growing up: The older we get, the easier it is to coast. We stop poking at the edges of our network, quit dusting off our plans, and sometimes trade ambition for autopilot. Why? Maybe because conventional wisdom whispers, “You should have it figured out by now.”

But what if “figured out” is just bullshit we tell ourselves to stay comfortable?

Networking: Not Just for Shameless Climbers

Back in the day, I’d pick someone from another part of the business, ideally higher up the food chain, and ask them out for coffee once a month. No secret handshakes, no corporate espionage just two humans swapping perspectives over coffee.

Yes, it was a little bit strategic. Yes, I probably wanted to be remembered if the right opportunity came along. But you know what? That’s how you meet would-be mentors. That’s how you get noticed. And sometimes? That's how real friendships start.

Why We Stop Reaching Out (and Why That’s a Mistake)

Here’s the plot twist: The higher you climb, the more your circle shrinks. Same goes for your personal life. The busier and older we get, the less likely we are to make time for new connections. or even maintain the ones we have.

So when you hit a crossroads, whether launching your own thing, leveling up, or figuring out “what’s next” it can feel awkward to reach out. You second-guess yourself. “Will I look desperate? Out of touch? Creepy?”

Spoiler: It’s only weird if you make it weird.

How to Be Strategic Without Feeling Like a Creep

Ready for some practical, non-creepy strategies for using your built-up career capital to get advice, help, or new opportunities? Here you go:

1. The Targeted Compliment

Reach out to someone whose work you genuinely admire, reference something specific they’ve done, and ask a direct question. People spot fake flattery a mile off, but thoughtful appreciation? That sticks.

2. The ‘Help Me Help You’ Approach

Offer to share your perspective on something you’re experienced in, and mention an area you’re trying to learn about. (E.g., “I’ve spent years in operations but am clueless about digital marketing. Mind a trade?”)

3. The ‘I Saw This and Thought of You’ DM

Share a relevant article, podcast, or event invite with a past colleague (no agenda attached). It reopens the door.

4. The Monthly Brain Trust

Start a small monthly call or meetup with others at a transition point. No gurus, just peers swapping stories and advice.

5. The Blunt Ask

Sometimes the only way is the direct way: “Hey, I’m working on X and could use your two cents. Can we chat for 15 minutes?” Respect people’s time and be ready to give back.

Try this:

“You don’t need to be a genius, you just need to be a little bit braver than most people are willing to be.” — Adam Grant

Final Pep Talk: Being Strategic is a Favour to Your Future Self

If you’re plotting your next act consulting, starting something new, or just not ready to slip quietly into irrelevance give yourself permission to be deliberate. It’s not about using people; it’s about not shrinking from your own ambitions or your own potential.

It’s not too late, and it’s not creepy.

Try this: