Four Obstacles to Being a Successful Encore Entrepreneur

Mike Armour

To succeed as an encore entrepreneur, we must be learning continually. Not only learning the ins and outs of running a business. But learning new skills and developing new levels of self-mastery.

The philosopher Carlos Castenada observed that there are four obstacles to skill development. They act as restraints that hold us back and weaken our drive to learn.

Taking on the Unfamiliar

The first is fear. Put simply, we already know how to do what we already do. What if we invest ourselves in learning new skills, only to embarrass oursevless? Only to discover that we are not very good at them? Only to find that they serve us poorly? Such questions breed timidity.

Or what if fear prevents us from stepping out into the unknown? From moving outside of our comfort zone? Then we're doomed to limited learning. We never learn inside our comfort zone. We only learn when we step into the unfamiliar.

Some people are more fear-constrained than others. Among successful entrepreneurs, however, is one common denominator: they don't give in to fear. And this is equally true whether the entrepreneur is 20 years old or 60 years old.

Feeling No Need

The second obstacle is power. To be specific, having enough control over our circumstances that we don't see a need to learn something new.

For example, if you're one of those rare encore entrepreneurs who begins a company with extensive financial resources at your disposal, you're less likely to be focused on learning to cut costs, build efficiencies, or manage cash flow. You have enough "financial power" that you don't sense a pressing need to tend to such concerns.

Or if you establish a one-of-a-kind business that is immediately successful because of its appeal, your success may lull you into complacency about continued innovation. After all, you have a corner on the market. Why knock yourself out trying to do new things?

Then one day someone figures out how to compete with you by offering customers more than you do. Because these new competitors are hungry and innovative, you soon find yourself at a disadvantage. Your market share starts to erode, and your entire focus becomes defending yours place in the market.

Both of these examples result from someone being in a powerful enough position that learning something new held no urgency for them.

Thinking We Already Know Enough

The third obstacle which Castenada identifies is clarity. When we think we truly understand something, we're not likely to expend a great deal of time or energy digging into it more deeply.

More than once I've seen older adults with a profound knowledge of their industry leave a successful career to hang out their shingle as a consultant. There is a great market, they believe, for what they know.

And commonly that's the case. But then they make a fatal mistake. Because their grasp of the industry has served them so well in the past, they count on it to serve them well in the future. They quit actively building their knowledge and skill base.

Needless to say, their precious knowledge soon becomes dated and irrelevant to the needs of those who would hire them as a consultant.

The same thing can happen when people have successful retail careers, then decide to strike out on their own and open a business. Thinking that they know retail, they become so swamped with putting the business together and making it run that they do not give enough time to staying abreast of new trends, new technologies, or new customer expectations.

On the other hand, had they begun the business with a strong sense that they had much to learn about retail, paying attention to this essential knowledge would have been a constant priority.

Giving Too Much Credence to Myths

The fourth obstacle — and one that's altogether familiar to many of my readers — is old age. Especially what we believe about it. There's a reason for the adage, "You can't teach an old dog new tricks."

Truth be told. there's more myth than truth to this adage. Our communities are filled with inspiring stories of men and women who late in life took on fresh challenges, mastered new skills, and achieved amazing results.

They reject the notion that they are too old to learn simply because mental function decreases somewhat with age. One of my dearest friends and colleagues in Russia finished her fourth doctoral degree at 69 years of age — in a field that she had never studied before. Apparently someone forgot to tell her that thing about old dogs.

Taking Inventory

Let me conclude, then, by inviting you to make a careful assessment of yourself.

Where is fear holding you back?
Where have you quit learning because you feel, "I've got that under control"?
Where has your previous mastery of a skill or subject reduced your commitment to keep that mastery fresh and up-to-date?
Where have you bought into myths about aging that are holding you back from more ambitious plans for your enterprise?

It's a valuable checklist. And not one that you're likely to see elsewhere on websites about starting a business or being a successful entrepreneur.

From my experience, however, success is largely a factor of two things: persistence and continuous learning. Anything that impedes learning therefore impedes success.

This article first appeared in Encore Entrepreneur inbox magazine on September 9, 2014.