Outside the Box: A growing number of retirees are heading to work — as entrepreneurs


More than 3 million baby boomers retired early as a result of the pandemic, according to a new analysis from Miguel Faria e Castro, a senior economist at the St. Louis Federal Reserve.

Some were laid off. Faced with the discouraging rejection that comes with the territory when someone in this age cohort tries to get back on the job, they opted to call themselves retired.

Others were enticed with early retirement packages. Worried that option might not come around again, they folded their tent.

“There is the question of whether the “retirements are permanent,” writes Faria e Castro. “Many of these new retirees may decide to return to the labor force.”

My reporting shows that observation is spot on. A growing number of early retirees who I have talked to appear to be planning a return appearance, but this time flexing their entrepreneurial muscles to do it on their own terms.

In my forthcoming book, I delve into entrepreneurship as one of the massive workplace trends for those over 50 moving forward. It has been gaining steam for a few years. 

For those of you who may have “retired” pushed by pandemic dynamics to do so and are ready to step back as your own boss, I reached out to Alisa Cohn, executive coach and author of the fine new book, “From Start-up to Grown-up,” for some guidance.

Cohn has a notable record advising founders of firms such as Etsy, Foursquare and Venmo. One of the things that sets her apart from the many coaches out there, in my opinion, is her practical focus on how your inner game can get the best of you when you’re the boss, and how to take control.

Nevermind your competitors. Start with you.

Kerry Hannon: What should you know about becoming a first-time entrepreneur at 50+?

Alisa Cohn: What you should know is you are a seasoned professional and an older, hopefully wiser person. You bring a lot more skills to the table than a younger entrepreneur. You’ve had the experience managing larger teams. You’ve had the experience building your management skills. You’ve amassed a network around you of people who want to help. And you have the wisdom of the long view and recognizing what you’re getting yourself into, and that it’s going to take some time.

The wisdom of things happening to us in life, the wisdom of age, brings you this perspective of knowing that life is ups and downs and your business will be ups and downs. You’re ready to take on the ups and downs that you are going to have to address as a new entrepreneur.

Can you talk a little bit about the sort of intergenerational teams that might be a secret to success for an entrepreneur over 50?

The older, more seasoned person brings that perspective and that wisdom and literally the skills and time in the water. The younger person has the finger on the pulse of what her generation wants and is looking at new ways to do things, plus a perspective formed by being a digital native, being more comfortable with vulnerability in the workplace, and less hierarchical.

If they will listen to each other and learn from each other, they will absolutely develop a better product. Meshing those two together, when they respect each other, is a very powerful combination.

Don’t forget what it was like to be 20 years younger and less experienced and therefore delegate and coach appropriately, which means they may actually need direction and guidance. They may make mistakes, get ready for that. Don’t be upset, create a learning environment.

What are your instructions for someone before a launch?

Do you have what it takes to be an entrepreneur? Are you ready, willing, and able to handle the extreme ups and downs that you’re going to go through? Are you ready, willing, and able to handle the psychology of what it’s going to take to try to invent something new and also the difficult work that it’s just going to take to bring something into fruition? Do you have the desire and ability to adapt to changing environments and grow rapidly? Have you tested your idea? Can you test your idea?

What’s one common mistake older entrepreneurs make?

In general, entrepreneurs are often known as control freaks, and only they can do it. The more you can delegate and give away, the more quickly, the more successful you will be, even if everything is not always done perfectly perfect.

Why is self-reflection key before launching a business?

Your company becomes a mirror of yourself, with all the good and all the bad. Self-examination helps you identify what leadership qualities you have, what qualities you need, and how you are going to make the most of your strengths, bridge the gaps in your skills, and strengthen some of your weaknesses.

 As I write in my book: Everyone has a natural leadership style. Here are six questions I give to my clients to help them focus on key aspects of their leadership style.

1. How do you express yourself to people? Do you ask them questions, listen to the responses, and supportively explore solutions together? Or do you tell them what to do and hold them accountable for the result?

2. How do you deal with conflict? Do you lean into conflict to try to eliminate it, or do you avoid it and hope that people work it out for themselves?

3. What’s your natural swing on giving feedback and having difficult conversations? Do you tend to wait to address issues or weigh in bluntly whenever you see a problem?

4. How much do you want to control the process? Do you watch over every step in the process or wait for the end result? Do you tend to assume you should handle most things or do you instinctively ask yourself who else could do a certain task? How much personal participation do you prefer and how much can you give up? Do you make decisions by yourself and let people know or do you gather opinions and get consensus from the team?

5. How do you respond to stress? Do you check out or shut down? Do you snap back? Do you work harder?

6. How do you make decisions?

Why is an ability to adapt an essential ingredient to success?

You will have to adapt very quickly and very regularly and often more than you realize. Here’s an example: If you’re the kind of leader who just brainstorms all the time, that actually is really fine for eight people, or for 20 people. When you’re in a hundred people, and you’re just brainstorming all the time and just sharing your thoughts, and people see you as the founder and the leader, they take everything you say seriously. Your suggestions are orders. Your inklings are orders. Your brainstorms are orders. They go off and run with it. Be aware of that.

Managing you can be a psychological challenge, what are some ways to tackle that?

Managing your psychology means overcoming self-doubt, dealing with your internal critics. Entrepreneurs are more likely to encounter depression and anxiety. If it comes up for you, then find people around you to help you stay the course.

Create a highlight reel. It gives you perspective on your capabilities and who you really are. My clients get a lot out of this when they are encountering self-doubt or concern or impostor syndrome. I say, listen, let’s step back. You’re a very capable person. Can you share with me three or four successes you’ve had?

Write those down. Read those every day, or read those when you’re encountering a lot of self-doubt or impostor syndrome. Read those when you’re about to go into a difficult situation.

Find an alter ego. An alter ego is — it’s not me doing this. You have a role known as the founder. How would the founder act in a circumstance like this? How would the CEO act? And if you can put it on that, you can give it a name. Finding almost a third party helps you be more unleashed.

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