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Welcome to this edition of Meaningful eMail with the most recent takeaway and updates linked here at the top, and then a full article for your consideration.
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Top Takeaways: Drive
Such a useful, easy-to-read book for effective communications. It's almost a manual in the way it's designed and written. Video version of my review is on LinkedIn or...
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If the first half of our career is about chasing ambition, is the second half about changing our relationship to it?
What were your big goals right out of college?
When I was a newly minted graphic designer, my dream was to have a byline on CD liner notes: “Creative Direction by Jackie Besser.” Even just typing my maiden name stirs up those early ambitions.
Later, working at Xerox, I admired my boss’s boss — a tiny but fierce woman with commanding presence — and set my sights on an MBA as my next ladder rung. I had a vision. A plan. A hunger.
Shew. I remember that version of me. Hungry, hopeful, gunning for the next big thing. (Well, bless my 30-yr-old heart.)
These days? I coach emerging leaders who are right there — and I love helping them grow into that next rung. They’re fired up about executive presence. Hungry to level up. Obsessed with presenting like a pro, handling high-stakes conversations, landing the next title. They can’t wait to be regional director, market vice president, chief fill-in-the-blank officer. But I also work with folks who’ve climbed the ladder, looked around, and thought: “Wait… this is it?”
I see this shift show up again and again in my mid-career coaching clients. People who once ran on ambition now find the fuel tank empty — or worse, the fumes are making them gag. The ladder’s still there, but they’re not sure they want to keep climbing.
The Shift Is Real
So what happened between our 20s and 40s?
Sure, a little disillusionment plays a role. (The corporate Kool-Aid doesn’t taste the same after you’ve mixed it yourself.) But there’s something deeper happening here — and it’s backed by both science and lived experience.
Take Maslow’s Hierarchy of Needs. In our early careers, we’re focused on stability, status, and belonging. But once those needs are mostly met, a new question creeps in: Is this all there is?
That’s when the drive toward meaning, contribution, and self-actualization starts to take over.
Or look at the fluid vs. crystallized intelligence shift — something I wrote about last month. As we age, we lose interest in fast-paced problem-solving and gain satisfaction from mentoring, synthesizing, and making sense of what we’ve learned.
This ambition recalibration shows up in some of the best books on midlife work and identity:
In Working Identity, Herminia Ibarra reminds us reinvention often comes not from big plans, but from small, purposeful experiments.
In The 100-Year Life, Gratton and Scott show how longer lifespans mean we need built-in career transitions to stay engaged and aligned.
In Wisdom @ Work, Chip Conley reframes midlife as the moment we become Modern Elders — offering EQ, insight, and context.
And of course, as Daniel Pink explains in Drive, our motivation evolves from external carrots to internal fuel: autonomy, mastery, and purpose.
The Shift Is Meaningful
What’s been striking is how many clients are feeling disconnected from mastery alone. They’ve done the work. Reached the milestone. And now?
They’re just... bored.
One client realized she’d been “mailing it in” for months. Not because she didn’t care, but because the spark wasn’t there. Through our coaching, she’s starting to rediscover it by shifting her goals toward impact, not output.
Earlier this year, another client - a sales VP - thought she just needed a new industry. But after we explored her strengths, values and purpose, she gave herself permission to chase a long-held dream: working with historic landmarks as a guide. She didn’t just climb a new ladder, she burned the old one and used the wood to fuel her next adventure.
So if the ambition that got you here isn’t cutting it anymore? Maybe it’s time to switch fuels.
Thoroughly unprepared we take the step into the afternoon of life... but we cannot live the afternoon of life according to the program of life’s morning.
- Carl Jung
We don’t talk enough about what happens when our ambition changes shape. But I think we should. Because it’s not a failure. It’s an invitation.
One to go deeper. To work differently. To define success for this chapter, not the previous one.
And that’s the kind of conversation coaching is built for.
P.S. Feeling this in your bones? I’ve got a few spots open for 1:1 coaching this summer. Just reply and we’ll set up a time to chat about what’s next for you.
P.P.S. If you like this newsletter and would like to support it, send it on to your circle of mid-lifers. Your recommendation means so much to me!
