Starting a Business After Age 50

By Jeff Williams

Posted : October 2, 2016

Category : Interviews

Starting a Business After Age 50
Jeff Williams

Expert Interview Series: Jeff Williams on Starting a Business After Age 50

Too many people think that life ends when their corporate career does. However, for many baby boomers, life truly begins to get good at 50 when they strike out on their own and go into business for themselves.

While the corporate world does not always appreciate the assets of employees over the age of 50, baby boomers have a lot to offer that can make for very successful second careers in entrepreneurship. 

We talked to Jeff Williams, the Chief Coach of Bizstarters to find out about starting a business after age 50. Jeff is a renowned business coach who has worked extensively with people over the age of 50 who are going into business for themselves for the first time.

We are seeing more and more people having a second career after retirement. What are some reasons for this trend?

Boomers are accustomed to being in the middle of the action both in their jobs and in their outside lives. This strong motivation continues even when they leave a traditional corporate job. They just aren’t ready to "hang up their spurs" like their parents did.

Another reason is that some have a long-harbored desire to pursue work in a strong personal interest that likely had nothing to do with their job responsibilities.

The last reason is the majority of folks over 55 are lighter on retirement assets than financial experts would suggest they need. So, many must continue to do income-producing work – often throughout their sixties and maybe even into their seventies.

What are some of the advantages of starting a business after the
age of 50?

Age doesn’t matter when you run your own business (except to the extent of considering stamina). Your customers only care that you deliver what you promised.

You can also enjoy a lot more schedule flexibility in your work, since you can set a varying amount of work time to meet personal needs (as long as you take care of customer needs).

Another reason is to avoid ever getting a pink slip again. You create your work security through the community of customers you attract and satisfy. People like to buy repeatedly from suppliers they trust.

One of the best reasons to start a business after the age of 50 is because you can pick the people you work with. When dealing with clients or customers face-to-face (such as in consulting or a service business), you can use your intuition to determine if you want to work with that person or business. Obviously, if you run an eCommerce business, you can’t really pick your customers; but that’s all right, since most of those just want you to ship what they ordered and get on with life.

What are some particularly useful resources that you know of for entrepreneurs who want to start a business after the age of 50, but need to catch up on some of the most important technological trends necessary for business?

Two online magazine sites, INC and Entrepreneur, have extensive archives of how-to articles on tech issues, such as the one I have recently used on how to best use LinkedIn for prospecting.

Another great resource is local MeetUp groups populated by tech people; we have several in the Chicago suburbs where I live. Now, I don’t always understand what they are saying in their presentations, but they are nice enough to take time to explain.

An unexpected resource might be local high school tech classes, such as the one in my area that helps students write apps. These young people are often glad to make some cash advising you.

Finally, your local library. My library has a complete tech support department, lends out laptops and tablets, offers ten or more software classes each week and has a fully equipped video recording studio. And I live in a town with just 75,000 people.

In an interview for Forbes Magazine, you talked about how age may be a hindrance in the corporate world, but can be an asset as an entrepreneur. How is age a detriment in the corporate world? What qualities are higher management failing to see in employees over the age of 50?

There is a dichotomy regarding age among corporate employers. In certain specialties such as manufacturing management, IT, and project management, large corporations are being hurt by mass retirements among boomers and are often offering flexible work arrangements to keep their people and even attract new ones.

But with many other corporate employers, the typical hiring manager is 45 years old and sees workers over 55 as economic drags because: (a) they cost more in insurance; (b) they aren’t up on tech; (c) they don’t want to work 70 hours per week; and (d) they don’t like to take orders from younger bosses. These are strong beliefs which are often substantially wrong.

What these employers are missing are that 55+-year old workers:

  1. Show up for work every day, on time.
  2. Are very disciplined in pursuing goals.
  3. Are good with a variety of people.
  4. Know a lot of people and so can network effectively.
  5. Are glad to share their knowledge with younger colleagues.

You’ve also talked about clients over the age of 50 being one of the biggest demographics Bizstarters is working with these days. Why is entrepreneurship so popular with baby boomers?

A Merrill Lynch survey in 2010 revealed that 75% of the over-55 people contacted said that they wanted to keep working well into their sixties. This comes out to 57 million workers. Now, lets say that 25% of these don’t ever really keep working after 60 (due to health, etc.); that still totals 45 million workers. We are now at the lowest workforce participation rate in the U.S. since the late 1970’s, so where will 45 million boomers find corporate work?

In fact, it is estimated that through full downsizings and involuntary early retirement deals, more than 10 million over-55 boomers have left the corporate world in the past seven years. Very few of them have found their way back. So, if you are one of the 45 million who are strongly motivated to keep working, and you are out (or will soon be out) of the corporate world, how do you do this? You create your own work – which is the essence of self-employment.

For people going into business for themselves for the first time after the age of 50, how might they go about filling the knowledge gap with younger employees? What are some reasons this might be a good idea?

In my 27 years as a business owner, I have always believed that you greatly benefit from working with people who are smarter than you are on some specific topic.

Today, you can easily find such people through a number of ways.

  1. Online freelance sites, such as
  2. Local schools and colleges
  3. MeetUp groups
  4. LinkedIn connections

Working with a younger employee is sometimes a necessity (such as when you own a fast food franchise), and it can be a good idea to assure the tech strength of your business. (We use a younger team of web designers to work on client websites. They are always up to date on the latest techniques).

This is often a matter of ego here; you must be willing to admit what you are not so great at and acknowledge that they younger employee is better at doing it.

What are some of the most popular types of businesses that baby boomers are starting? What makes them such an attractive choice?

In no particular order, using some of our clients as examples:

  1. Consulting, such as plant health and safety.
  2. Consumer or Business services, such as QuickBooks advisement or gourmet meal preparation.
  3. Craft or fashion items sold online, such as custom wire jewelry.
  4. Coaching and teaching, such as pre-retirement planning.
  5. Retail food and services (this category is largely supplied through franchised business).

What are some unexpected ways that owning your own business can positively impact your life?

  1. Having a mission each day keeps your spirits strong, which benefits your health.
  2. You often find out that you can, in fact, succeed with a project from start to finish.
  3. You can give back to your community, both in terms of time and money.
  4. Your fellow small business owners are often more friendly and reliable than your corporate colleagues were (with whom you were competing for promotions).

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