Wonderful Ways to Get into Business When You Are Over 50

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Just before I received a request from Home Business Magazine asking me to write an article about hiring older employees, I found myself reading the Sunday New York Times. The Times had published an interesting article by Rob Walker entitled “When Early Retirement Turns Into a Total Bore.”

Reading this article reminded me that I had written many blogs about starting a business after you retire. So, with the New York Times article and the Home Business Magazine request in mind, I thought this was an excellent opportunity to share my perspectives on being over 50. How can you continue to be a valuable contributor to society? Can you find the right pathway as an employee, a freelancer in this gig economy or, and this is very important, even as a startup entrepreneur?

The value of “over 50”

Rob Walker’s article talked about re-entering the marketplace after you have retired. From our own experience, from working with clients and interviewing others, there are several things you should consider as you look at your options:

1. Experience counts:

Just remember, you have a lot of experiences. For over thirty years, I suspect, you have developed some excellent technical skills and, very importantly, deep-rooted interpersonal skills. Don’t discount your experiences. And while you might not have skills associated with fast-moving new technologies, you do know how to deal with people. These make you very valuable. You just need to know how to “sell them.” So, if you are a prospective new hire, keep in mind what you know and share the stories that make them come alive. Of course, of equal importance, make sure you know what you don’t know.

2. Think motivation:

If you are “too bored to stay retired” I suspect you are motivated. You like the idea of working. Work is probably intellectually challenging to you. Potential employers see this as a big plus. And if you are going to start a business, consider this a real benefit. There are many different ways to find your over-50 path that can leverage your skills and your desires. Choose carefully.

3. Workplace culture:

Your experiences and your traditional workplace culture might not exactly fit into the current environment, so you need to be sensitive to the changes that are taking place in the world of work. Managing “hands” as they say is different than managing “minds” —those knowledge workers. Moreover, the Millennials are different. You might be interested in smoke breaks, while current employees might be interested in ping pong. Yes, there are differences in today’s culture (versus a boomer culture). You are going to have to adapt to the new culture. Remember that by 2020 half the workforce will be those 30-somethings. There are more of them (Millennials) than you.

The next big question: What type of work should I do?

Let’s take for granted the statement “too bored to retire.”

You are going to have to answer the question: what am I going to do? You can work for someone, for yourself or a charitable organization. That decision is all about what excites you and what resources you have to invest with or live off of.

If you are ambivalent, try something first as a freelancer because if it doesn’t work, no harm, no foul! But what if you are committed to work?

What if you want to build something of value? Your own passion turned into a company?

Something to perhaps pass along? Maybe that passion you want to turn into a business—from that band you always wanted or the executive search firm you have been dying to create.

If you think that is the case, here are some of the things you should think about before that final leap:

1. You can’t be half in.

Particularly when starting a new business. Think about your energy level. I don’t think you can be casual with a new venture. Be prepared to work hard. Don’t underestimate what it takes to start something. Are you “all-in”? Ask yourself if you are willing to make that commitment.

2. Can I afford to fund this venture?

Depending on what you are going to do, it is either going to cost a little or a lot. And the “little” will creep up and the “lot” will also increase. Our tendency in laying out plans and budgets is that we tend to believe that great ideas work on their first pass. Very few do, and you need to give yourself some reserve. With that in mind, let’s revisit the affordability issue again. How much can you comfortability risk and how will that affect your future, if all fails. You need to ask yourself that question because, for you, so far your life has not been bad. What isn’t so good is a failed venture and then back into retirement. The second part of affordability also deals with third-party funding. How do I fund my endeavor? Is it family and friends? Bank borrowing, etc.? This puts pressure on individuals. Do you want to be responsible for other people’s money?

3. How are your analytical skills?

Today every business or venture generates a ton of data. But how do you take all that data and turn it into something that generates meaningful direction? How do you interpret that data and turn it into good decision making? If you have this skill or can acquire it, great. If not, then I fear that you could get lost. You need to understand the consequences of limited analytic skills.

4. Are you learning to be nimble?

Today, even more than ever, you must be a lifelong learner. It is difficult to keep up with ever-evolving technology. For many, this creates fear. If you have been retired for even a short period of time, you would be amazed at how quickly the world is moving. You are going to have to learn what you have missed, discover the new tools available, and work hard to stay current in the future.

5. Think about your desire to manage people.

I used to say that managing people was my toughest job and greatest challenge. Do you want to do that in the future? Or do you want to start a business that might not be people dependent. It is getting tougher everyday as the demand for good people in an overheated economy increases.

6. Are you prepared for a changing workforce?

Millennials behave very differently than boomers. Whether one group is better or worse is open for debate. However, they are different and each needs to be nurtured in different ways. It is one thing to work for someone and not be sensitive, but hiring and managing these people is something very different.

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Andrew Simon, MBA
Andrew Simon, a partner in Simon Associate Management Consultants (www.simonassociates.net), has had a 50-year career as a senior executive. He founded and ran Questar Assessment Inc., the fifth largest K-12 summative assessment company in the U.S. As a serial entrepreneur, Simon also developed and ran businesses in real estate development and did start-ups inside larger corporations, such as Citibank, Bankers Trust, Norcliff-Thayer and Lederle Labs. Earlier in his career he was part of a team that launched L’Oréal into the consumer-products arena. Simon also is a trained and certified Innovation Games® facilitator and has conducted more than 50 client engagements using Innovation Games methods.

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