Harnessing Wisdom and Experience: A Guide to Entrepreneurship for the Over-60s

I have a close friend who had a successful sales career. He was an employee all his life. His last gig ended, and he was trying to find another opportunity. He loves sales. He loves developing sales talent. He needs the money.

The problem was his age. My friend is sixty-six years old. When he applied for sales management positions, he came in second. There was always a “better candidate.” Despite his high energy, age remained the single biggest question.

It was time for my friend to move from employee to entrepreneur. To do so he needed to stop thinking about earning a living and start making a living by working for himself. The business which makes the most sense for him is sales consulting.

The sixty-something baby boomers have much to offer. It will not come in a full-time job but in part-time services. There is a potential army of micro-entrepreneurs. These men and women should start their own business with one employee. Themselves. A business which will gross $25k to $250k per year depending on how much of their self-esteem they are willing to risk.

To build these solo enterprises, they will need to be prepared for rejection. This is a big issue at sixty plus. When you get older, you expect people to respect you for all you've accomplished, not question your competence. But this is exactly what will happen when you start your own business.

You need to be prepared to sell yourself. Many over sixty haven’t had a resume in thirty years. They succeeded in business because of their network. Well, the network is no longer doing the hiring.

Be Resilient Like 25. Be Smart Like 75.

At sixty-five, I asked my dad if he would go back and do life all over again. He reflected a moment and said, “I would only do it again if I can go back knowing what I know now."

What you lack in energy, you have in wisdom. Creating a solo enterprise means doing what a twenty-five year old would do to get business, but now you have experience, and lots of it. When you were twenty-five you ran through walls, but now at sixty-five, you know which walls have opportunity on the other side.

Here are five strategic decisions you must make for success.

1. Operate in Your Monopoly

Where are you the best in the world? No, really. You are so good at something, for someone, that it is your monopoly. No one can compete with you there.

Answer these questions to help you determine your market, service, methodology, and network.

1. What industry did you last work in?

2. Within that industry, what business do you understand better than any other business?

3. Within that business, what size business (market segment) were you most successful in?

4. Within that size business, which position do you really connect with?

5. Within that position, what are their critical needs?

6. Within these critical needs, which of these can you solve?

7. Within your solution, how do you solve the problem?

8. Finally, how does your faith or belief system show itself in your solution?

As you can see, you need to dig deeper and deeper. Become more and more focused. Zero in on the “it.” This is your monopoly.

2. Address a Critical One-Time Need

A friend of mine created a great solo enterprise. Joe Wilson was a successful salesman because of his unique ability to call high in an organization. When he entered his sixties, he went from employee to entrepreneur by creating a business around this unique skill and methodology.

He approached vice presidents of sales at IT companies. He told them, "I can get you an appointment with any prospect." They hired him as a consultant, and he got them high-level appointments.

Every business has critical one-time needs. Based upon your monopoly, decide the businesses you focus on and the one-time need you can satisfy for that business.

3. Confidently Work Your Network

I was in a Bible study with the sales manager I spoke about earlier. I asked everyone to give their name and describe their occupation. He introduced himself and then described his occupation as: “I am a sales consultant which is another way of saying, I am an unemployed salesman.” While humorous it too easily left people thinking, “The old guy is unemployed.”

If instead, he said, “I am a sales consultant who works with small business owners of commercial security product distributorships with two to five million dollars in sales and have a broken sales force,” maybe someone in the group knew a business owner in this exact situation.

4. Be Affordable

A successful solo enterprise always provides an affordable solution. People need the problem solved but don’t expect to pay an independent consultant a fortune to do it. Everybody wants a good deal. You can shorten your sales cycle and make a good living by giving people a good deal in your monopoly.

5. Provide Quick Results

You are addressing one-time needs. Could you make sure you have a methodology that shows quick results? You must get in, assess the situation, and fix it quickly.

If you are a sales consultant, as my friend is, then you must figure out the sales problem quickly. You design your methodology and can only execute it in your monopoly area. You can get in and out quickly and with good results.

If you can take rejection like a twenty-five-year-old and go deep in deciding your five strategic decisions to build a solo enterprise, you will succeed. You have the wisdom to help many, but now you must have the humility to do so.