5 Leadership Traits Every Boomer Entrepreneur Should Possess


Earlier this year, FreshBooks released its second annual Self-Employment Report, which stated, “Dramatic workforce shifts in American history could happen in as little as two years—with potentially 27 million Americans leaving traditional work in favor of self-employment by 2020.” Also, according to the report, 61% of self-employed baby boomers plan to work through retirement by choice, a much higher percentage than Gen-Xers (47%) and millennials (45%).

While the prospect of baby boomers embracing self-employment and entrepreneurship is exciting to witness, the shift does not come without its set of obstacles. Boomer entrepreneurs will still need to adapt bits and pieces of their personality to the changing world to stay relevant and successful. Luckily, most “boomerpreneurs” possess great leadership traits—and these traits can be emulated by other generations, as well. Here’s a look at boomers’ top strengths:

1. An understanding of how to be strategic and creative

Baby boomers have years of experience on their side, working in roles that have allowed them to be imaginative and thoughtful, while also allowing them to make plans to reach their goals. For entrepreneurs who are in their fifties (or older) to take on leadership roles, they must have an understanding of how to be equally creative and strategic. One trait should not overshadow the other, or worse, not be present at all. Rather, there should be a balance where practical decisions support whimsical, out-of-the-box ideas.

2. Enthusiasm

When you’re enthusiastic about the work you’re doing, everyone can see it. It reflects off you and bounces onto those surrounding you, from employees to business partners. Boomer entrepreneurs generally start businesses, not with the end game of making money, but to pursue an interest or hobby they are genuinely passionate about. That kind of joy is necessary for leadership because it shows the world that you’re interested and invested in your ideas. Positivity is infectious. If you love what you’ve created and treat others with respect, the word will get out about your business, and customers will be attracted to your positive energy and drawn in.

3. A thick skin

Nobody gets through decades of hard work without having some of their thoughts or ideas rejected or declined, and boomers are more aware of this than any other generation. Rejection hurts, but the sting only lasts the longer you let it stick to your ego. To succeed in today’s market, you need to be tough; you need a thick skin. This will prevent you from dwelling too long on problems in your business—like negative social media commentary, for example—so you can work to remedy situations instead.

This characteristic is also one that can be passed down to employees—sort of. If you can’t give someone a thick skin, you can provide them with constructive criticism. This allows your team to have a better understanding of their weaker spots and gives you the chance to provide advice for how to make those areas stronger.

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4. Risk-taker

No entrepreneur should be content with playing it safe, no matter what their age. From Gen Z to baby boomers, leaping forward and going all in to chase your dreams should be your Plan A and Plan B.

5. Focus

As each day progresses and boomers get a little bit further away from their youth, this doesn’t mean they can’t be, or can’t act, young at heart. To succeed as a boomer, the key is being alert and on task when it comes to every aspect of your startup. Channel the younger version of yourself who was laser-focused on everything you were assigned and was always hungry for more. You don’t have to dominate everything you do, but you should be able to step up to bat and take careful, practiced swings.

RELATED: Forget Retirement—Many Baby Boomers Are Starting Small Businesses Instead

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