Ambition Doesn't Retire

Ambition doesn't retire at 40, 50, or 60+.
There's no monopoly on ambition held by the young.

I remember early in my management and leadership career the excitement of being picked to be part of a future leaders group. Being "picked out" was a thrill and a sign that I was on what I thought was the right path.

But what happens when you stop being picked for those groups and you're not a future leader (probably because you're already one)? I remember a sense of, wait, what are you saying I'm too old? Are you saying I'm not part of the future?

But I still feel ambitious—what am I supposed to do with that?

There's an outdated belief that reinvention, entrepreneurship, and bold career moves are reserved for the young.

Wait, I'm Not Done Yet

There are stats that suggest 25% or more of new entrepreneurs are between 55 and 64 years old.

Take Vera Wang, for example. She was a competitive figure skater before reinventing herself as a globally renowned fashion designer in her 40s. That must have taken a fair amount of ambition.

What's to say that your great 2nd or 3rd act isn't just waiting for you to lift the curtain on that project you've been talking about for years, just waiting for the "perfect moment"?

The motivations for a second or even third act are as diverse as the individuals pursuing them. For some, it's about finding meaning or leaving a legacy. For others, it's the freedom to explore new passions or the mental sharpness that comes with learning. Or maybe you've been forced into it by the whims of corporate restructuring.

The important thing to keep in mind here is that you don't need permission to keep being ambitious.

The trick as we get older is to use what we already know to help us attain the skills and knowledge that we don't have. It's our secret weapon of experience that gives us an edge if we lean into it. 

Try This:
Think about a time when your experience gave you an advantage that younger colleagues didn’t have. How might you leverage that type of advantage in a new venture?

The Modern Elder

If you're looking for some guidance and motivation to get your next act on stage, check out Chip Conley.

Chip is an entrepreneur, bestselling author, and leading voice on purposeful living after 50. After founding Joie de Vivre Hospitality, he joined Airbnb at age 52 as Head of Global Hospitality, mentoring the next generation of leaders.

He is the author of Wisdom@Work: The Making of a Modern Elder and founder of the Modern Elder Academy, which helps people over 45 reinvent their lives and careers.

Conley inspires others to see age as an asset and embrace ambition at any stage of life.

Ambition Building

You may not have given your ambition muscle much use lately and be struggling to work out how to re-engage it. Here are some practical ways to begin:

• Start Small: Try micro-risks or tiny experiments (I know I keep saying this). A side project, a new role, or even volunteering can open doors.

• Challenge Norms: Voice alternative opinions and embrace new perspectives.

• Keep Learning: Take courses, seek mentors, and stay curious.

• Reframe Your Mindset: Separate your self-worth from success and failure. Consider keeping a failure journal to reflect on lessons learned.

Try This:
Choose one tiny experiment from the list below (or create your own) and commit to starting it this week:

• Sign up for one online course in a field you're curious about

• Reach out to someone doing work you admire and ask for a 15-minute chat

• Dedicate one hour this week to that project idea you’ve been sitting on

What Am I Doing?

I've talked in past articles about how this newsletter is not only to share ideas but to also remind me of what I need to be doing.

So this week I've signed up to Sectionschool.com to take some courses in AI. I'll let you know how it goes and share any insights I get.

What Are You Going To Do?

Let me know what you're doing to keep the flames of ambition stoked.

Why Is Ambition Important?

Stagnation is a real danger at any age, but it's particularly risky later in life. As we age, we're less likely to be exposed to new opportunities unless we actively seek them out.

Every risk you take builds resilience and creates a more interesting life.

One of the unexpected benefits of reinvention is the opportunity to connect with others. Whether it's through a new project, course, or volunteer role, you'll find yourself surrounded by like-minded individuals.

And as we know, community is a key factor in living a longer, happier life.

It's natural to feel apprehensive. At 50+, there's a societal expectation that you're supposed to "have it all figured out." But the truth is, most people are too busy worrying about their own lives to judge yours.

Final Thoughts

If you're contemplating a change, know that it's never too late to pursue your ambitions. Whether it's a new career, a passion project, or a lifestyle shift, the possibilities are endless.

The key is to take that first step, no matter how small. Your future self will thank you for the courage to try.

Try This:
What's your next act? Reply to this email or share your ambition plans in the comments. Sometimes saying it out loud is the first step to making it real—and you might just inspire someone else to take their leap too.

So, what's your next act?