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Your Career Path Doesn’t Have to Be Linear (Mine Sure Wasn’t)

The next chapter doesn’t owe you a straight line. It just owes you a pattern worth following.

When I was 22, I genuinely thought I was going to be a high school gym teacher.

Then I took a job as a youth director at the local YMCA. Part of the gig was planning an annual leadership conference for high school students. It was the smallest line item in my job description and somehow became the part I lived for. The agenda-building. The speaker hunt. The moment the doors opened and 100 teenagers walked in.

I had no idea I was watching my actual career take shape. I just thought I liked the conference part.

That “I like the conference part” turned into a full-time job with an association. Then a corporate meeting planner role.

Then, after a decade of loving most of it and quietly hating about 30% of it (looking at you, post-event invoicing), I went hunting for a job that was only the parts I loved. I found one: meeting broker. I negotiated hotel contracts for meeting planners and let them keep all the post-event chaos.

The only catch? I had to find my own clients. As a raging introvert, cold-calling and networking events were both off the table. So I built a personal brand instead. LinkedIn. Twitter (RIP). A blog. A YouTube channel. A consistent six-figure business that ran on visibility instead of vibes.

And that is the thing that turned into this — what I do now, which is help senior-level women like you build their own next chapter.

So. Phys. Ed. to personal branding coach. Not a straight line. Not even a curvy line. More like a drunk GPS rerouting itself for 25 years.

The next chapter doesn’t owe you a straight line

Here is the thing about reinvention: it is almost never the elegant pivot you see on LinkedIn. It is a series of “huh, I like that part” moments that only make sense in the rearview mirror.

If you’re staring down your next chapter right now and trying to map it like a project plan, I want to save you a few years. Here are three things to hold loosely as you go.

Principle 1

Don’t discount a single experience you’ve already had

Every job, every side project, every volunteer thing, every “this didn’t work out” moment is currency you can spend later. The Phys. Ed. degree didn’t go to waste. It taught me how to break complex skills into teachable steps, which is literally what I do every day with brand strategy.

You have 20-plus years of experience. None of it is wasted. The trick is recognizing what’s actually transferable versus what was just a paycheck.

Principle 2

Be ruthless about narrowing what you actually want

Loving most of your job is not the same as loving your job. The 30% I hated about corporate meeting planning was eating my soul. The version of me who tolerated it would never have built the version of me that exists now.

In your next chapter, you have permission to be picky. You’ve earned it. Make a list of every part of every job you’ve done. Cross out the parts that drained you, even if you were good at them. What’s left is your signal.

Principle 3

Look for the pattern, not the path

Career advice tells you to find the next job. That’s the wrong unit of measurement. You’re looking for the next pattern.

My pattern was always there. I just couldn’t see it. I was the kid who organized the school dances, the youth director who lived for the conference, the meeting planner, the broker, and now the coach. The job titles changed five times. The thing underneath never moved.

What’s your pattern? It’s hiding in the work you’d do for free. In the parts of your job nobody asked you to do but you did anyway. In what your peers always ask you for help with. Find that, and you’ll stop looking for a new career and start designing one.

The path forward isn’t a job posting. It’s a through-line you’ve been building your whole life without noticing.

What’s the part of your work you’d do for free? That’s the principle worth following.

Want to find the pattern in your own work? Take the Payable Expertise Assessment — it’s a quick diagnostic that tells you what people would actually pay you for in your next chapter business. No fluff, no funnel, just clarity.

Cheers,
Leanne

P.S. Speaking of next chapters — mine is about to include a brand new podcast launching late June. If you have a senior-level professional woman in your life who’s quietly plotting her reinvention, this one’s going to be for her. More soon. 🎙️

P.P.S. My real-life newsletter goes deeper – more insights, more goodies, and more of the good stuff you won’t find anywhere else. If you want in, you can subscribe right here. I’d love to have you.