Ready for Your Second Act? 6 Tips for a Successful Career Change

You’ve had a good run doing whatever you’ve been doing for the past few years (or decades). Maybe you’ve accumulated a nice little nest egg or completed a successful exit, and making tons of money is no longer a pressing priority for you.

Congratulations on making it this far. Now, what’s next?

Rather than ride off into the sunset, many older (or, let’s say, “experienced”) leaders want another challenge before they hang it up. Call it a second act.

Problem is, the idea of doing something totally different, or even kind of different, is daunting even for accomplished entrepreneurs. If you’re not sure where to start, here’s how you can make it seem like less of a leap.

1. Turn What You’ve Learned Into Something You Love Doing

Building something from nothing is like being a celebrity — you can’t know what it’s like until you’ve done it.

That’s scary for most people, which is why most people aren’t cut out for life as founders. On the other hand, if you’ve walked the walk and come out in one piece, you know things most people never will.

And that puts you in a position to turn what you’ve learned into something you truly love — and something that adds value to the world. That’s what SWS Venture Capital founder Steve Streit did after leaving Green Dot, the pioneering fintech company he built and ran for nearly 20 years. 

With SWS, Streit is finally able to give back to the next generation of founders. To give them support and to help them avoid some of his mistakes. 

If that sounds like a dream job, well, it is for Steve Streit. And it can be for you too.

2. Look for an “Emeritus” Role That Actually Requires Some Work

Not so inclined to run your own venture capital firm? Put on your “advisor” or “director” hat and be a mentor without going (all the way) back into the trenches.

There are plenty of advisor and board director roles out there for accomplished founders, regardless of specialty or industry. You won’t earn as much as you would in a more active role, but we’re assuming money isn’t the primary motivator here.

3. Reconnect With Old Colleagues

Oh, so you are ready to get back into the trenches? Get on LinkedIn and reconnect with colleagues you haven’t worked with in years. Or counterparties you worked with on a deal. Or people you only know of by reputation.

The sky’s the limit. The goal is clear: launching a new venture with help from fellow high achievers you respect — and more importantly, can work with.

4. Do Some Good in the World

You may or may not have the money to do some serious philanthropy. But you can do some good in the world even if you still need the paycheck.

Nonprofits, NGOs, government agencies, for-profit benefit corporations — wherever you want to work, they’re hiring. The pay might not be quite as good, but it’ll sustain you, and you can go to sleep at night feeling good about what you did during the day.

5. Retrain and Retool (It’s Never Too Late)

You don’t hear much about 40- and 50-somethings going to law school or getting their MBAs these days. Not because it’s not happening, but because it’s now so common as to be unremarkable.

So no worries about sticking out like a sore thumb, even if you’re (much) older than the median. It’s never too late to acquire new skills and credentials. And if they boost your earning power in the back half of your career, all the better.

6. Find a Mentor and Plan Your Next Steps

We all need support. We all need direction.

We all need a mentor. Unfortunately, not all of us have anyone to look up to (professionally, at least).

But according to digital entrepreneur Neil Patel, finding a mentor isn’t hard if you know where to look. You just need to find someone with relevant experience, willingness to take on the role, and the temperament to convey honest feedback (even if it’s not what you want to hear).

Though they can’t make it happen for you, your mentor can at least help you plan your next move.

Read: 5 Leadership Advice For Remote Leaders

It’s Never Too Late for a Second Act

If you have your health and your wits, it’s never too late for a second act. Even if most of your contemporaries are happy to putter around the garden or tool about the golf course.

And if you can follow any (or all) of these tips to make a successful career change later in life, you’ll have just one regret: that you didn’t make the leap sooner.

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