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Entrepreneurship after 50: Is It Right for You?

Many midlife entrepreneurs choose to create their businesses backwards.

They back into entrepreneurship after 50 rather than actually choose it.

After trying to find a job without success after a year or two, I’ll hear a midlifer say, “I guess I’ll just have to start a business.”

And that statement right away lets me know this idea is new to them, and they probably don’t know much about it.

Which is the opposite of how we used to view the journey of becoming an entrepreneur.

In fact, most entrepreneurial education and training assumes that someone knows they want to have a business from an early age, and has a new and different idea they want to bring to the world.

You may remember the career interest inventories you took back in school. “Entrepreneurship potential” was measured in those inventories via a constellation of traits typically attributed to entrepreneurs like extroversion, enjoyment of working with people, and creativity. If you tested high for those characteristics or preferences your guidance counselor would tell you’d likely make a good entrepreneur.

Back then, too, there were many local family businesses, and if your family was one of those, you learned the ropes first hand and understood what was needed to succeed. From there, you’d focus on developing those competencies in college.

Still for others, entrepreneurship might have always seemed like the right move. You may have realized as a kid that you didn’t quite fit into those restricted career boxes, and saw having a business of your own as a way around that dilemma. Perhaps you even had an individualistic streak or original idea from an early age that formed your entire being and way of moving through life.

The common thread among all these traditional paths to entrepreneurship is that the ‘spark’, the desire, that choice to found a company was something realized and often nurtured from a younger age.

All these paths are based on the belief that entrepreneurs are born that way; that it’s not something you can learn to become.

But that’s not the situation you find yourself in now if you’re 50 or beyond, and considering starting a business.

Midlife entrepreneurs don’t necessarily have a specific idea they want to bring to the world, a brand new something that will set the world on fire.

Most have never considered starting a business at any other time in their life.

Now they see this type of endeavor as an option of last resort when they’re unable to land a job that pays them the salary they deserve or made at a previous job, or if they haven’t been able to secure employment at all.

So starting a business becomes your ‘Plan B’ — the only thing left for you to do, rather than THE thing you want to do.

And that’s because the RISK of entrepreneurship after 50 actually feels safer to you than continuing to engage day to day in the disappointing pursuit of employment ‘out there’.

To keep trusting the outside world, instead of trusting yourself.

The idea or motivation behind your surprising desire to start a business is often simple: to exert some control over your life.

To find some way to take care of yourself and your family, to have financial security once again.

To restore your life to what it was.

In the past, few people would think of entrepreneurship after 50 as a way to restore financial security. That’s because we usually think starting a business is a precarious undertaking.

But midlife entrepreneurs have already concluded that it’s less risky to start a business than to continue to depend on others for their security, or rely on the way things used to be.

So an individual choosing entrepreneurship after 50 is a different kind of person, and a different type of entrepreneur.

Did you know there are more individuals age 50 and over creating new companies today than any other age group?

You already know the World of Work is changing — that’s no surprise.

But by 2020, forty percent (40%) of all workers are expected to be freelancers (individuals self employed as individual contractors) (Forbes). You may find this an astonishing statistic, but some forecasts are even higher, predicting 50% self employment in just three years (Bloomberg). Only fifty percent of people working in 2020 will have typical ‘jobs.’

The urgency you may feel about starting a business of your own is shared by more and more people as they try to prepare for a workplace down to 50% of the employment options.

So what do you do?

How do you prepare yourself for this new kind of future, and the possibility of starting your own business?

You’ll find there are a tremendous number of local education and resources available to help you decide the legalities. There are courses to help you select what legal structure you want (sole proprietorship, LLC or corporation), to teach you the process of how to collect state sales taxes and pay them, or to determine your accounting method.

Many of these courses are completely free, offered by the small business center at your local community college or SCORE (Service Corp of Retired Executives) chapter offices.

But most of those free education opportunities put the cart before the horse. Before you start taking those classes, you should take time to figure out something essential.

Check in with yourself about who you are at midlife, and what you want for the rest of your life. Yes, we’re talking about ‘rest of your life planning.’

Do you have the ‘right stuff’ to become an entrepreneur?

What competencies do you have that will help you successfully found a company?

If you haven’t taken a ‘career’ or interest inventory in a few years, now would be good time to identify your skills and strengths – especially those that will allow you to become a good business owner.

Odds are you have considerable knowledge and experience, all of which can be remarkably beneficial to this path, but the key is to match those up with a type of endeavor that fits you as you consider entrepreneurship after 50.

If you don’t also take time to narrow down the type of work you’d like to do, or the industry your business will be part of, then you’ll have difficulty narrowing down the skills you need to develop to prosper. Don’t skip this important preliminary step.

If you’ve just started thinking about creating your own business as an answer to financial concerns, don’t let the layer of desperation motivating you keep you from doing a thorough analysis.

Too many folks prematurely jump in, hoping their endeavor will ‘evolve’ however it can, and that’s not a good foundation upon which to launch a successful venture. Practice due diligence here!


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