Retirement Redefined: Ditch the Golf Shoes and Embrace a Profitable Side Hustle

Retirement today is vastly different from what it was decades ago, and the changes are both exciting and meaningful. With advancements in healthcare extending lifespans and people staying active well into their later years, retirement has transformed from a period of leisure into an opportunity for reinvention and purposeful living.

During a recent trip to Florida, I had the chance to speak with two Uber drivers who were retired professionals. They shared that driving for rideshare platforms wasn’t just about making extra money—it also gave them a sense of routine, social engagement, and fulfillment. One remarked, “I can’t play golf seven days a week, but driving gives me something to do and people to talk to.”

This sentiment echoes what many retirees are discovering: Retirement should be a transition to something, not simply an exit from work. For decades, people structure their lives around careers, and suddenly leaving that behind can leave a void. That’s why having a plan for this next chapter—whether it involves travel, spending time with grandchildren, volunteering, or pursuing new hobbies—is essential for long-term happiness.

The Rise of the "Side Gig" in Retirement

One of the most interesting trends in modern retirement is the rise of part-time work or side gigs. Inflation, delayed savings, and longer life spans have made financial planning more complex. According to a recent survey by D.A. Davidson, 41% of retired Americans don’t feel financially secure enough to support their ideal retirement lifestyle. Yet only 8% currently have a side gig, despite two-thirds wishing they did.

This gap presents an opportunity. Side gigs offer dual benefits: additional income and renewed purpose. Exploring these options before retiring allows individuals to think creatively about how their interests, skills, and passions might translate into fulfilling post-retirement roles.

Here are some practical examples of side gigs retirees have embraced:

• Creative Writing: A former university professor and psychologist turned his love of storytelling into a successful mystery novel series. He now writes full-time, blending entertainment with therapeutic insights.
• Craft Entrepreneurship: Another retiree expanded her knitting hobby into an Etsy business, creating custom sweaters and scarves while generating modest supplemental income.
• Community Engagement: A communications professional transitioned her volunteer role at a retirement home into a paid part-time position, allowing her to stay connected to a cause she loved.

These aren't just jobs—they’re expressions of identity and passion that continue to evolve beyond traditional career paths.

Planning Ahead for a Purposeful Retirement

The idea of retirement as a purely leisure-focused phase is fading. Today’s retirees are looking for ways to remain engaged, contribute meaningfully, and even grow their financial security through flexible opportunities. Our survey found that among Americans over 50 who haven’t yet retired, 63% have considered taking on a side gig once they do. And of those already doing so, 93% report enjoying their work.

Modern medicine may be giving us more years, but how we choose to fill them makes all the difference. Retiring to something—a new venture, a community role, or a creative pursuit—can provide structure, joy, and even a sense of adventure.

If you're nearing retirement or thinking ahead, consider what activities bring you joy, what skills you’ve honed over your lifetime, and how those might serve others—or generate income. Whether it's writing, crafting, consulting, or mentoring, the possibilities are vast.

Ultimately, the goal is to design a retirement that feels rewarding, purpose-driven, and uniquely yours. By starting the conversation early and exploring potential side gigs while still working, you’ll be better prepared to make the most of this exciting life stage.