How to Stay Current As An Aging Business Owner


“I used to be with it, but then they changed what it was. Now what I’m with isn’t it, and what’s it seems weird and scary to me… and it’ll happen to you, too.”

Believe it or not, this is actually a quote from The Simpsons. In this particular flashback scene, Homer’s dad walks in on a teenage Homer rocking out to his favorite music. His dad thinks the music sounds terrible and Homer says his dad isn’t cool enough to understand. Little does Homer know, his dad understands much more than he realizes. He explains that one day Homer will get older and struggle to keep up with the trends which will inevitably make him “uncool” in the eyes of society — and as the flashback ends, it’s revealed that his dad was actually right.

As we grow up in a generation so heavily reliant on sending snaps, tweets, and Boomerangs via social media, there is the push-pull between embracing getting older and also wanting to remain cool enough by BuzzFeed standards. For entrepreneurs especially, getting older alongside your business presents the challenge of wanting to enjoy the comforts of a steady startup but also continue to go the extra mile and think outside of the box. What can aging entrepreneurs do to make sure they stay in the loop in an authentic way? Don’t just look to memes and hashtags as your only strategy for keeping up with the next generation — focus on a few of these initiatives too.


Read everything that you can — and write too.

One of the best way to stay on top of trends is also incredibly simple: read. Subscribe to newspapers, magazines, and newsletters to open your mind and discover what’s happening within your industry and on a local and global scale throughout the world. Pick up books by influencers you admire and listen to podcasts while you’re at it. You’ll also want to start writing. Publish blog posts on sites like LinkedIn or Medium to establish yourself as an expert within your field and share your expertise with a new, wider audience.


Retool your website and refresh your online presence.

Don’t let your brand’s site grow stagnant! Check in with some of your favorite websites and take note on what they do well that you would like to emulate for yourself. Remodel your own site to be easily accessible across all devices from mobile to desktop, make it clear to navigate from your homepage to your contact us tab, and consider aesthetics and means of keeping customers on your site longer, like including pop-up newsletter windows to subscribe to for more content they crave. While you’re hitting refresh on your site, do a little revamp your social media accounts too. Edit bios, add in new profile or cover photo images for the season, and make sure all of your contact information is up to date!


Learn from (and listen to) other generations.

As we age, it gets easier to write off other generations by dismissing them because of their youth. Don’t fall into the “they’re too young and don’t know what they’re talking about” trap. Make it a point to surround yourself with other generations and embrace the chance to learn from them. Hire interns while they’re at college, bring on millennials as part of your staff, and pay attention to what your younger customers are saying about your brand online.


Say yes to accepting feedback.

You might already be used to getting feedback from customers of your small business, but what about personal feedback? Encourage your team, partners, and even mentors to provide you with personal feedback. Be open and willing to accept their thoughts on changes or adjustments you can make as a leader to become a stronger business owner, no matter what age you are.




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2 Replies to “How to Stay Current As An Aging Business Owner”

  1. Doug Martin

    I unjustly “write off” members of the younger generation because of my mistaken belief that they are lazy, or think they know everything. However, I have to keep in mind that they are likely “writing me off”, too, because they believe I am too old and set in my ways. Members of the younger generation likely believes I am not tech-savvy.

    In both cases, our judgments are incorrect. Like you wrote, we have to keep an open mind about everything.

    Thanks for the great post!

  2. Miles Austin

    Love your post- ‘Listen’ and ‘Read’. Those two alone can improve everyone’s lives whether young or old. Thanks.

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