Seven Tips for the Reluctant Senior Entrepreneur

Two “senior” entrepreneurs (women in their 50s) explain how to overcome the reluctance to start your own business when you’re older. These days, entrepreneurship is simply self-reliance, they explain.

NewsHour economics correspondent Paul Solman reports on late bloomers who decided to take the plunge into self-employment. Read the full transcript.

A note from Paul Solman: Judi Henderson-Townsend is the 55-year-old mannequin entrepreneur who, with her social media consultant Cynthia Mackey, fascinated NewsHour viewers a few weeks ago by extolling the virtues of “senior entrepreneurship.” Graciously responding to my request, she and Mackey then offered readers of this page Ten Tips for Senior Entrepreneurs. A further excerpt from my original interview with Townsend soon followed and high tech entrepreneur Vivek Wadhwa joined the discussion by explaining “Why Older Entrepreneurs Are Crucial, Even in Silicon Valley”.

In Thursday’s Making Sense post, Judi Henderson-Townsend and Cynthia Mackey address a familiar figure in America’s latest “jobless recovery”: the reluctant senior entrepreneur. They were plenty reluctant themselves, they write.

Judi Henderson-Townsend and Cynthia Mackey: Senior entrepreneurship is a trending topic. Yet for every senior who sees entrepreneurship as an exciting opportunity, there is another senior who sees entrepreneurship as an intimidating option of last resort.

Age discrimination, job layoffs, dwindling 401(k) accounts and the potential erosion of Social Security benefits are a few of the reasons why seniors are turning to entrepreneurship in large numbers. In our previous blog post we listed 10 tips for senior entrepreneurs looking to start a business. But owning a business can be an anxiety-ridden experience, and the anxiety is magnified if you are an entrepreneur because you “have to” vs. “want to.”

As two senior entrepreneurs who were once reluctant to take the plunge, we want to share some advice that made a difference to us. But first a little background on our entrepreneurial journeys.

Cynthia’s story: I enjoyed my corporate experiences but always felt constrained by the bureaucracy. As a consequence, I was always pushing the envelope, often a little too far. My first entrepreneurship experience was working for a small military sub-contractor. I had no desire to start my own company, but wanted to be part of a team. I loved this new opportunity and being part of the decision-making process! Despite the growing number of contracts the company brought in, we were blind to financial decisions of the chief executive that ultimately caused its demise. Similar situations occurred at other small companies I later worked for. I realized that working for others wasn’t working out for me. So I figured there was one other thing I hadn’t tried — going out on my own.

Judi’s story: An early experience in entrepreneurship when I was in my mid-30s was a disaster for me. I was so emotionally crippled by the experience that I swore I would never do that again. I became an accidental entrepreneur while purchasing a mannequin from someone on The buyer ran the only mannequin rental service in town and was closing shop. I impulsively bought his entire inventory thinking this would be a fun hobby to do while still working full-time. Granted I had never touched a mannequin before or worked in retail. What began as a sideline business has become my full-time venture for the last 11 years. At 55, I am not thinking about retirement, but how I can further expand my business.

1. Entrepreneurship — Another Name for Self-Reliance
In the days of an agriculturally based economy, if crops didn’t grow, one had to find another way to feed the family. Perhaps services were bartered or a product was created and sold. You had to use your talents and resources to solve a need — which is what an entrepreneur does. However, today’s meaning of the word can conjure up images of having to meet payroll, lease a building and deal with human resource issues — which may seem daunting. It can be less intimidating if you see yourself as fulfilling a need and if you perhaps call yourself a freelancer, consultant, solo-preneur or independent contractor.

2. Lean Into it
If possible, don’t leap into entrepreneurship, but start gradually. When Judi first started her mannequin business, she still had a full-time job. She eventually negotiated to work there part-time so that she could still have benefits and a steady source of income while investing in and building up her business. When 9/11 put an end to her day job, she already had the foundation laid for her entrepreneurial venture, making the transition much easier. Cynthia put a little money aside for several years, and eventually reduced her personal expenses over time. She also took on extra contractual work to fuel the business and shore up financial resources. There is no specific or right way to do it, but “leaning in” gives you a great way to build as you are able.

3. Create an Ad-hoc Advisory Team
Before you launch your venture, conduct informational interviews with senior entrepreneurs to get advice and bolster your confidence. If you don’t know anyone in your field, Job Shadow is a website that allows you to conduct online interviews with entrepreneurs from a variety of industries. Walking the path of an entrepreneur can be isolating at times. As much as they love you, family and friends don’t fully know what it’s like unless they have done it before. So identify a trusted colleague or two, perhaps even an advisory board that supports your vision but is objective enough to be candid with you.

4. It Takes More Than Passion
While passion is important, identifying a business that is suited to your personality and skill sets is equally as important. For example, if you have a passion for cooking, that doesn’t mean restaurant ownership is for you. Perhaps there are other related ventures that may be a better fit for your skills, personality and finances such as catering or becoming a personal chef, restaurant critic, or instructor. Taking seminars for entrepreneurs can assist you in determining what your strengths are. Organizations such as the Service Corps of Retired Executives (SCORE), Small Business Development Centers and nonprofit organizations focused on developing small businesses can provide consultants, courses and resources at little to no cost. Search the Internet for online courses and free white papers to help you become better informed in your field and the latest technologies that affect it.

5. Monetize Your Expertise
If you’ve developed expertise over the years in a certain discipline, entrepreneurship can be a chance to capitalize on your experience. Judi’s 58-year-old bookkeeper worked for a number of years in the finance departments of large corporations. She now works as an independent contractor for several small businesses. The flexible schedule and variety of skills she gets to use fulfill her in a way that working as an employee did not.

6. Turn Your Hobby or Interest Into Your Livelihood
Have you ever imagined your hobby providing your entire income? Entrepreneurship can be a chance to explore interests that you could only dabble in when you worked full-time. A friend of Cynthia’s worked for many years in retail before starting a bed and breakfast. Stories of seniors who have turned a personal interest into a business, like the therapist who became a perfume maker, can be found on the Senior Entrepreneurship Works website.

7. Avoid Analysis Paralysis
Sometimes we can’t get started because we are still trying to figure everything out. I mean, everything! Perhaps it’s the perfect manufacturing process for your product or the logo that’s exactly right for your brand. Often the best way to learn is by doing something, and if a mistake is made, then readjust. A business plan is an organic process not cast in stone.

In Cynthia’s case she has pivoted her business based on the needs of clients. She initially provided web design services for a wide variety of clients. But since her clients were uncomfortable using social media, she started offering education and training for baby boomers so they could use social media to grow their business.

Judi initially started out just renting mannequins. But as a result of requests from clients, she expanded her business to include mannequin sales, mannequin recycling, mannequin repairing and even renting her mannequin warehouse out for events.

In other words, sometimes you have to take the first steps and feedback from clients will direct you to the next step.

Judi Henderson-Townsend is the owner of Mannequin Madness, an award-winning small business that rents, sells and recycles mannequins.

Cynthia Mackey is a tech-savvy online marketer and founder of, a website offering courses on how small business owners can use social media to grow their business.

This entry is cross-posted on the Making Sen$e page, where correspondent Paul Solman answers your economic and business questions