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10 Great Reasons to Become a Boomer Entrepreneur

This positive aging coach says: Maybe it's time to bet on yourself

By Mike Kennedy

(This article previously appeared on

The recession of 2008 and its negative impact on retirement portfolios and career prospects created a significant increase in next-chapter entrepreneurial ventures. After a lifetime of working for someone else, many boomers relish the opportunity to be their own bosses for a change. The good news is that the timing couldn’t be better.

I speak from first-hand experience. I spent 30+ years as a consumer products sales executive before going out on my own to launch Your Future Reimagined, a coaching business to help people 50+ launch and scale entrepreneurial ventures. Knowing what I know now, my only regret is that I didn’t take the leap 10 years ago.

10 Reasons to Become a Boomerpreneur

Here are 10 reasons why now is a great time to become a “Boomerpreneur:”

1. Age doesn’t matter when you’re the boss. Ageism can be a major factor for someone 50+ seeking employment. But a new venture can be a perfect alternative for those tired of the corporate grind and are not ready to retire.

2. You could have 20 or more productive years ahead of you. Warren Buffett is 88 and still goes to the office daily. Assuming you have good health, there is no reason why working into your late 70s can’t be an option.

3. You can take advantage of your ability to generate income past 65. David Blanchett, head of retirement research at Morningstar, found that just three years of additional income improves a person’s odds of having a financially secure retirement by 55 percent.

4. You pick the people you choose to work with and those you don’t. Sometimes you can’t be too picky in the start-up period, but with success comes the ability to be much more selective about hiring.

5. With the advent of Internet-based businesses you can work from almost anywhere. As a retirement transition coach and consultant, not only do I have the ability to work from home, I also have the option to work remotely when on vacation. This flexibility can be a very important factor when considering ventures in retirement.

6. You have the opportunity to build your business around something you enjoy and are passionate about. There are a fortunate few who land on a career or venture that they are truly passionate about right out of school. But for the vast majority of us, true passion has proved to be elusive. After 25+ years of making a living, this is your opportunity to create a legacy.


7. You have 25+ years of experience and expertise to draw from and the network, social skills and maturity to go with it. You really can take all your accumulated experiences in life and successfully apply them to a new and exciting venture. Today, people over 55 are almost twice as likely to create successful startups as those 20 to 34.

8. You’ll be able to stay mentally- and socially engaged. Staying engaged in your retirement years can play a significant role in overall happiness levels.

9. The cost of entry has never been lower. It has never been less expensive, and therefore less risky, to start an entrepreneurial venture. Many new businesses today are launched for well under $10,000 and can run for less than $500 per month.

10. Boomers aren’t afraid to take chances. Compared to other generations, the boomer set is far less fearful of taking risks. A sizable 43 percent of boomers identified themselves as being high-risk takers, in a 2013 survey by and Millennial Branding.

Maybe it’s time to bet on yourself!

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Mike Kennedy is a positive aging coach and president of Your Future Reimagined Coaching in Cambridge, Ontario, specializing in  helping 50+ clients launch and scale entrepreneurial ventures. At 56, he transitioned from his career as a sales executive in the consumer products industry. Read More
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