Retired with a business

Not too long ago, my coworkers produced a report to help understand small business owners. It’s filled with solid insights that will challenge your ideas on who small business owners are and where their priorities lie.

I found, for myself it pointed out details I had overlooked, but, in hindsight, were staring me in the face. In my career as a designer, I worked with a wide range of clients over the years of varying company sizes. During those years, several of the owners turned out to be retirees. The report indicates that recent retirees fit into the Uncertain Hopefuls category. Here’s a quote from the site defining Uncertain Hopefuls:

They have an idea, a skill, or a craft but struggle with the next steps of creating a thriving business. The learning curve looks steep when you’re at the bottom. They need help but aren’t always sure where to find it or who to trust. The segment most likely to struggle with issues related to age and health. This can sap their energy and rob them of productivity without a moment’s notice.

This is where the “Aha” moment came for me. RETIREES! Of course! I have seen this exact scenario many times and will continue to see it. In fact, my dad is now in that category. He’s retired, but still kicking!

As the report states, retirees are spinning up businesses not just as a side gig, but also out of necessity in cases where a lack of available retirement funds puts them in a spot where they need supplementary income. This group also isn’t super interested at investing a ton of time trying to learn a new product. They’re retired. They are ready to enjoy life. This makes so much sense.

Now, we have some questions to answer:

  • What changes can we make to our product or services to give them the tools to help their side gig succeed without them having to struggle to learn our products?
  • What can we do to inspire trust in us and our products?
  • We can we do to further improve accessibility across the WordPress ecosystem?

By Michael Arestad

I design at Chromatic.


I feel lucky for having a typography mentor who was in their 70s and while reviewing one of the business cards I had designed said to me, “Mr. Maeda. You designed this in 5.5 point Univers. That was beautiful to me as a young person like you. Now I cannot read it. Go fix it.”

I was in my 20s at the time, and didn’t know what he was talking about. But I discovered that when you get into your 40s, in general, you can’t see small things as well as you used to:

So one way to address the older audience is to simply a design from explicitly larger typesizes — versus in reverse where we design for the smaller typesizes and expect the a11y settings to make the type bigger. It’s sort of like “mobile first” but instead, “big type first” … perhaps it can catch on?

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