Want to Launch a Business Later in Life? Here's How to Get Started

It's so great being your own boss!

Lisa A. Beach

Published September 12, 2024

Ditch the outdated stereotype of older women mostly playing Mahjongg to fill their open-ended time. Today's seniors are rewriting the script when it comes to retirement. Some seek a new purpose and passion after retirement, some yearn to keep learning and some simply need additional income.

The Growing Trend of Older Entrepreneurs

Over the past two decades, the American workforce has undergone significant transformations, impacting those in midlife and beyond. Workers are delaying retirement, taking on side hustles and finding a new purpose as they transition into retirement.

Whether it’s part-time employment, freelance work or entrepreneurial ventures, the aging workforce is embracing flexibility, redefining retirement norms and exploring various options to stay financially engaged. The Federal Reserve Bank of Minneapolis reports that “just 45 percent of U.S. 65-year-olds are retired, compared with 58 percent in 2000.”

A Pew Research Study found that the number of working Americans 65 and older has nearly doubled in 35 years. The Pew data reveals that approximately one in five Americans in this age group were employed in 2023 and that persons 75 and older are the fastest-growing group in the workforce.

More than just “staying busy,” this shift is about capitalizing on a lifetime of experience and pursuing passions long held at bay. In his book From Strength to Strength, author Arthur Brooks discusses the concept of the “second mountain." He describes this as a phase when purpose and contribution take center stage after retirement — a midlife shift from what he calls the “first mountain” of self-achievement. Entrepreneurship perfectly aligns with this notion, allowing older adults to build upon their skills and experience and create something new and meaningful.

And older adults bring a wealth of experience to the table! After decades in the workforce, you might have honed your skills in areas like management, sales, finance, publishing or marketing. This translates into a significant advantage when navigating the complexities of running a business. Plus, don’t underestimate the power of passion. Retirement offers the opportunity to revisit dreams you might have put on hold and turn them into reality.

My Own Passion Project

Personally, I’m pursuing my own passion project that taps into my 35-plus years as a freelance writer. As I approach 60 this year, I feel the desire to share my hard-won wisdom from decades of experience. So, I launched Expert-ish Freelancer, a free newsletter to help people launch or elevate their own freelance business, and to share tips I learned from my years as a writer and public relations professional on marketing, healthy business habits and building a client base.

One of my subscribers, Trudy, has been a teacher for 22 years, but she’s slowly been building up her portfolio in hopes of transitioning exclusively into freelance writing. Jenn wrote that she’s been “lazily freelancing here and there since my kids were born, but the kids are now 15 and 21 so I figured it was time to make something more of myself.”

Along with steering others, my newsletter gives me a rich sense of purpose beyond the income-producing work I do as a freelance writer. I also get the privilege of helping fuel other people’s freelancing dreams. Plus, I’m picking up new skills along the way, as I learn how to create a digital newsletter and market it online. It’s a win-win!

Launching Your Freelance Business After Retirement

The world of freelancing provides both challenges and opportunities. To help you navigate this entrepreneurial path, I turned to Katie Fogarty, a 54-year-old communications and career coach at The Reboot Group. She also hosts the top-ranked midlife podcast called A Certain Age. Fogarty grew her coaching business from one-on-one freelance gigs to corporate coaching and regularly works with mid-lifers looking to reinvent themselves. She’s walked the talk of moving from side hustle to main hustle.

Fogarty notes that decades of work experience add up to decades of rich, deep professional relationships. She suggests tapping into your trusted network — they can become your first clients, help you with testimonials and make referrals on your behalf.

“When I launched my career coaching business in 2015, I did free LinkedIn profile makeovers for 10 people in my network,” Forgarty recalls. “In turn, they gave me testimonials for my marketing materials and became a source of referrals. Later on, when I launched my podcast in 2020, the first six or seven women I interviewed came from my personal network.”

Fogarty also points out some common challenges faced by older people when launching a freelance business.

“While freelancing offers flexibility in setting your schedule and rates and the freedom to pick and choose clients, being your own boss can come with surprising paperwork and a fresh set of demands on your time,” she cautions. “Suddenly, you need to be an expert not only in your field but in business development, bookkeeping, legal, web development, IT, etcetera. Getting a business up and running — and keeping all the balls in the air — can be overwhelming.”

Fortunately, you don’t need to do it alone! Check out the wealth of resources available to help you navigate the world of entrepreneurship. Organizations like AARP and SCORE offer free or low-cost mentorship programs, training workshops and networking opportunities specifically designed for older adults.

If you’re considering launching a freelance business, Fogarty advises getting your legal and tax paperwork finalized. Also, it’s time to develop, or enlarge, your online presence.

“In today’s work world, you need a website and an effective social media presence to be taken seriously,” Fograrty advises. “Figure out where your customers are spending time online and invest time in that channel. Do you need to become a TikToker? Not necessarily. But at a minimum, you should be strengthening your LinkedIn.”

The bottom line: It’s never too late to pursue your dreams, leverage your decades of experience and build something meaningful.

Have any of you reinvented yourself later in life? How so? Let us know in the comments below.