Embracing the Gig Economy: How Dan Simms Found Success in Dog Sitting

When Dan Simms left his job selling insulation at the age of 56, he faced a common dilemma: how to make ends meet while searching for a new job. Little did he know that a simple suggestion from a friend would lead him down an unexpected path to financial stability and fulfillment. This is the story of how dog sitting transformed Simms’ life and opened up new opportunities for him and his wife.

A Surprising Side Hustle

On the recommendation of a friend, Simms decided to explore dog sitting as a side hustle. He signed up with DogVacay, now known as Rover, an online platform that connects pet owners with sitters. This decision marked the beginning of a new chapter in his life. Leveraging his sales background, Simms took proactive steps to attract clients. He distributed business cards at local veterinarian offices, dog groomers, and kennels, effectively marketing his services in the community.

From Side Hustle to Main Income

Fast forward more than eight years, and Simms, now 64, has turned dog sitting into a lucrative venture. Alongside his wife, who retired from her sales support job in 2022 to join him in this endeavor, they now earn between $75,000 and $80,000 annually. This income has provided them with a comfortable lifestyle, allowing them to travel eight to twelve weeks a year without financial strain.

Simms expresses gratitude for this unexpected turn of events, stating, “I feel very blessed, particularly after the last 10 years of my career, switching jobs frequently.” The couple’s financial success has also allowed them to delay collecting Social Security benefits and avoid dipping into their retirement accounts prematurely.

The Growing Concern Among Retirees

Simms’ story is not unique. Many retirees today are increasingly worried about their financial futures, particularly in light of rising inflation and unexpected expenses. According to a 2025 survey by investment management firm Schroders, 92% of retirees expressed concern about inflation diminishing the value of their savings. Nearly half reported that their retirement expenses were higher than anticipated, and over 60% were uncertain about how long their savings would last.

Exploring Financial Opportunities

For retirees feeling financially pinched, there’s no need to panic. The gig economy offers a plethora of opportunities to generate extra cash. From pet sitting to taking paid surveys, retirees can find flexible ways to supplement their income without sacrificing their desired lifestyle. Kathy Kristof, founder of SideHusl.com, emphasizes that there has never been a better time for retirees to earn significant side income, suggesting that it’s possible to make $500 to $1,000 a month while still enjoying retirement.

Practical Ways to Boost Your Income

If you’re a retiree looking to enhance your financial situation, consider these ten practical strategies:

1. Tighten Your Belt

Start by reviewing your bank and credit card statements to identify areas where you can cut back on expenses. Financial adviser Alissa Krasner Maizes suggests taking advantage of free resources, such as public libraries, which offer access to books, audiobooks, music, and educational events. Reducing the frequency of paid services like housecleaning or haircuts can also lead to substantial savings.

2. Find Unclaimed Assets

Many retirees may have unclaimed assets that could provide a financial boost. Bobbi Rebell, a certified financial planner, notes that security deposits, uncashed paychecks, or forgotten investment accounts might be waiting to be claimed. These assets can sometimes amount to thousands of dollars, offering a significant financial cushion.

3. Explore Gig Economy Opportunities

Platforms like Rover, TaskRabbit, and Upwork allow retirees to leverage their skills and interests for extra income. Whether it’s dog sitting, freelance writing, or handyman services, the gig economy provides flexible options that can fit around your lifestyle.

4. Rent Out a Room

If you have extra space in your home, consider renting it out on platforms like Airbnb. This can generate a steady stream of income while allowing you to meet new people.

5. Offer Tutoring or Teaching Services

If you have expertise in a particular subject or skill, consider offering tutoring or teaching services. This can be done in person or online, providing flexibility and the opportunity to share your knowledge.

6. Participate in Market Research

Many companies pay for consumer opinions through surveys and focus groups. Participating in market research can be an easy way to earn extra cash in your spare time.

7. Sell Handmade Goods or Crafts

If you have a talent for crafting or creating, consider selling your goods on platforms like Etsy. This can turn a hobby into a profitable venture.

8. Become a Virtual Assistant

With the rise of remote work, many businesses are looking for virtual assistants to help with administrative tasks. This role can often be done from home and offers flexible hours.

9. Drive for Rideshare Services

If you enjoy driving, consider becoming a driver for rideshare services like Uber or Lyft. This allows you to set your own hours and earn money on your schedule.

10. Invest in Your Skills

Consider taking courses to learn new skills that can enhance your employability or allow you to start a new venture. Investing in yourself can pay off in the long run.

Conclusion

Dan Simms’ journey from insulation sales to dog sitting exemplifies the potential of the gig economy for retirees. By embracing new opportunities and leveraging their skills, retirees can find financial stability and fulfillment in their golden years. Whether through dog sitting or other side hustles, there are countless ways to generate extra income and enjoy a comfortable retirement. With the right mindset and approach, retirees can navigate their financial futures with confidence and creativity.