When I left my corporate career, it was my choice.
I was ready to leave that chapter. But I wasn’t ready to stop working.
I didn’t feel finished. And I certainly didn’t believe that everything I had learned during decades of working with people and organizations had suddenly lost its value.
But I did have a problem.
I wasn’t sure what came next.
For most of our working lives, someone else gives us a structure. We have a job, an organization, responsibilities, meetings, goals, deadlines and people who expect something from us.
We may complain about some of those things, but they also give shape to our lives.
Then one day, that structure disappears.
I knew what I had done for the previous 30 or 40 years.
I wasn’t nearly as certain about what I wanted to do for the next 10 or 20.
That uncertainty began what has become my own encore journey.
Over the years, I’ve coached and consulted. I’ve created a podcast and interviewed some fascinating people. I’ve written, taught, experimented with business ideas and learned technologies that weren’t even imaginable when I started my career.
More recently, I’ve become fascinated with AI and what it might allow experienced people to do that would have been difficult, expensive or simply impossible to do on their own just a few years ago.
And plenty of the things I’ve tried haven’t worked.
That may be one of the most useful things I’ve learned.
Reinvention isn’t a straight line.
I Think We Ask the Wrong Questions
When someone leaves a long career, one of the natural questions is:
“What job can I get?”
There’s nothing wrong with getting another job. For some people, that’s exactly the right answer.
But I’m increasingly convinced there’s a better question to ask first:
“What do I want my life to look like now?”
That changes the conversation.
Maybe you want to consult a couple of days a week.
Maybe you’ve always wondered what it would be like to own a business.
Maybe buying an existing company or franchise sounds more interesting than starting something from scratch.
You might coach, teach, advise or mentor.
You might do several of those things at the same time.
And maybe you want something else too.
Time with your spouse, children or grandchildren. Travel. Exercise. Volunteering. Learning something completely new.
Or simply the ability to enjoy a Tuesday afternoon without asking someone’s permission.
That’s a very different way to think about a career.
I’ve come to think of it less as finding your next job and more as designing your next chapter.
Experience Is an Asset, But We Have to Learn How to Use It
One thing I believe very strongly is that experience has value.
At this stage of life, we know things we simply could not have known when we were 30.
We’ve hired people and occasionally hired the wrong people.
We’ve made decisions without having all the information.
We’ve lived through reorganizations, recessions, changing leadership teams and wave after wave of new technology.
We’ve learned which problems really matter and which ones only look urgent.
And somewhere along the way, we’ve learned quite a bit about ourselves.
The challenge is that the marketplace doesn’t always know what to do with all that experience.
Sometimes we don’t know what to do with it either.
We may have spent decades describing ourselves with a title.
Plant manager.
HR executive.
Engineer.
Banker.
Sales leader.
CEO.
Take the title away and you’re left with a much more interesting question:
What can I actually help someone do?
That question can open an entirely different set of possibilities.
That’s Why We’re Building Best Careers After 50
Over the last several months, I’ve been working with others to create something we’re calling Best Careers After 50.
The idea started with a pretty simple question:
What are the best ways for experienced people to continue working, contributing and earning money after 50, while having more control over how they do it?
We don’t think there’s one answer.
For some people, it may be consulting.
For others, entrepreneurship.
It could mean buying a business, working part-time, building a portfolio career, advising younger companies or combining paid work with other things that give life meaning.
We want to explore all of those possibilities.
And on October 20, we’re holding a Best Careers After 50 webinar to begin that conversation.
We’ll talk about some of the paths available, but I’m even more interested in helping people think through how they decide which path actually fits.
How much do you want to work?
How much money do you need, or want, to make?
What are you unusually good at?
What do you never want to do again?
What would you like to learn?
Who do you want to spend your time with?
And maybe the biggest question of all:
What would you like the rest of your life to look like?
Most of us were never taught to ask questions like those about our careers.
Maybe it’s time we did.
You Don’t Have to Have the Answer Yet
If there’s one thing my own journey has taught me, it’s that you don’t have to know exactly where you’re going before you start.
You can explore.
You can experiment.
You can talk with people who have taken paths you’re considering.
You can try a consulting project without deciding you’re now a consultant.
You can investigate buying a business without buying one.
You can learn how to use AI.
You can start writing, teaching, coaching or advising before deciding whether you want to build a business around any of it.
We sometimes imagine our next chapter arriving in a great moment of clarity.
My experience has been quite different.
Often, you learn your way into it.
That’s what I’d like Best Careers After 50 to help people do.
If you’re 50, 60, 70 or beyond and find yourself thinking, “I’m not done yet, but I’m not sure what’s next,” I’d love to have you join us on October 20.
Come explore the possibilities with us.
Register for the Best Careers After 50 webinar here.
And if you know a friend or former colleague who’s trying to figure out their own next chapter, please pass this along.
There’s a lot of life after a traditional career.
The opportunity is deciding what you want to do with it.
