Retirement often marks the end of a career and the start of a leisurely life. But what if you could do more? What if you could embrace a new venture, work for yourself, and transform retirement into an exciting second chapter? Many retirees are doing just that, tapping into their entrepreneurial spirit and exploring “unretirement” through self-employment. According to Guidant Financial’s 2024 State of Small Business survey, about 37% of self-employed Americans are boomers (ages 60 to 78), a significant rise in older entrepreneurs.

But is starting a business in retirement the right move for you? Before you dive into the world of entrepreneurship, consider whether this path aligns with your lifestyle, goals, and interests. Here’s how to determine if self-employment is the best fit for your retirement years.

The Joy of Working for Yourself

Working for yourself can be incredibly fulfilling, offering a sense of purpose, flexibility, and control over your schedule. As Cathy Buday, self-employed managing editor at EIX.org, explains, “When you have work that you love, it energizes you.” That sense of fulfillment is a powerful motivator, particularly in retirement when many seek to stay active and engaged.

Retirement can also offer a respite from age discrimination in the workplace. Teresa Ghilarducci, professor of economics at The New School for Social Research, notes, “If you’re working for yourself, you’ve eliminated a barrier to unretirement—the barrier of age discrimination.”

Moreover, Christine Benz, author of How to Retire, suggests that retirement can be the perfect time to explore entrepreneurial endeavors: “Retirement is an interesting life stage to explore doing something entrepreneurial.” But before you take the leap, it’s important to ask yourself: What do you really want to achieve during this phase of life?

Action Steps for Starting a Business in Retirement

If you’re leaning toward starting your own business, here are a few actionable steps to guide you through the process:

1.Assess Your Interests and Skills: Reflect on what excites you. Is there a passion project you never had time for during your working years? Joe Casey, managing partner at RetirementWisdom.com, advises figuring out what “itch you need to scratch” a year or two before retiring.

2.Plan Ahead: Begin planning your business early, ideally five to 10 years before you retire. Emily Guy Birken, author of The 5 Years Before You Retire, stresses the importance of early retirement planning to ensure you’re ready for the financial and personal aspects of self-employment.

3.Financial Preparation: Before launching your business, assess the costs and Starting a business often requires upfront investment in tools, marketing, or hiring support. Websites like QuickBooks or FreshBooks can help you track expenses, manage invoices, and monitor your budget as you start your venture.

4.Start Small: Instead of diving in headfirst, consider testing your idea on a smaller This can help you gain experience and avoid overwhelming yourself. Platforms like Upwork or Fiverr offer opportunities to freelance and build your client base without a major commitment.

5.Get Mentorship and Advice: Before committing to a full-time business, talk to others who’ve walked the path. As Leslie Braksick and Mark Linsz recommend in Revealing Your Next Season, engaging in a period of “discernment” will help you make informed decisions. Talking with a mentor or consulting with someone who runs a similar business can provide invaluable insights.

Evaluate Your Readiness

Running a business can be both exciting and challenging. Here are three key questions to help you determine if self-employment is right for you:

1. Do I Have the Time?

Running a business often requires more time than you might expect. Entrepreneurs can find themselves working long hours, especially when just starting out. Cathy Buday suggests considering other life commitments like volunteer work, family obligations, or hobbies that might compete for your time.

2. Do I Have the Right Personality?

Self-employment requires discipline, independence, and resilience. As Jeri Sedlar of the “Don’t Retire, Rewire” advisory firm points out, it’s not always easy: “You better ask yourself: ‘Are you willing to do whatever it takes and really do it?’” Consider whether you have the personality to work independently, set your own goals, and handle the ups and downs of entrepreneurship.

3. Can I Afford the Risks?

Starting a business can be financially risky. Fritz Gilbert, founder of the Retirement Manifesto blog, recommends starting with a part-time commitment or getting involved with someone else’s business before going all in. Ensure you have a solid financial cushion to cover your expenses as you grow your business.

Be Ready for the Work

Starting a business may sound appealing, but be prepared for the hard work it entails. As Leslie Braksick suggests, talk to someone who has successfully started the type of business you are considering. This will give you a realistic sense of what the day-to-day work will look like. For example, if you want to open a bed-and-breakfast, be ready for more than just hospitality. Braksick shares the story of a woman who wanted to run a B&B and realized that much of the job involved laundry, repairs, and problem-solving, not just socializing with guests.

Final Thoughts: Embrace Your Second Act

If you’re considering working for yourself in retirement, it can be a fulfilling way to stay engaged, productive, and financially secure. Many retirees are discovering that the joy of entrepreneurship can bring new excitement, as long as you are prepared for the challenges ahead.

Are you thinking about starting your own business in retirement? What steps will you take to make it happen? Join the conversation and share your thoughts in our Age Brilliantly forum. Let’s explore this exciting new chapter together!