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How to Enjoy the Heck out of Retirement by Not Retiring

retirement 1Like many of you, I am well past the age when I could start receiving Social Security retirement benefits. And though I play golf (not well), I am not ready to retire. Why? Because life is too exciting to be sitting on a lounge chair and reading the newspaper.


There is still a world of things you can do

For some of you, this stage of life might mean volunteering for a not-for-profit in your community or traveling to places you never thought you would see. Or even starting a new hobby. But for me, it means doing the same types of things I have done my entire adult life: keeping active and building businesses. I personally like the challenges. Yes, I still get high building revenues and generating profits. And if I can’t do it for myself, I enjoy helping someone else do it.

Now, I recognize that after a certain age, this might not be the most appropriate way to spend your day but for me it just works!

Here’s a check list to consider before going back into business:

If, like me, you still want the challenge of working, you might want to:

1. Go find something that excites you. Do you want to consult, run a bike shop, start a teaching business? If so, just do it! For your next venture, you probably need to learn something. But Google can provide almost everything you need to know. These days, it’s easy to gather information on just about anything…enough, at least, to get your blood flowing.

2. Be prepared to use your analytical skills. Today, data is everywhere and also, data is king. If you have been in an organization that has used data in a meaningful way, that’s great. But remember, it is not the data but what you do with it that is important. Specifically, it’s how you interpret the data that enables good decision-making. If you have not had that type of experience, you need to figure out how to acquire it because without the ability to understand all the important nuances of today’s data, you are at a serious disadvantage.

3. Assess your energy level. This is important. Be honest with yourself. Do you want another full-time career or just something to keep you occupied on a part time basis? Can you be “all in”? Can you see yourself in a new 40-hours-plus career? How committed can you really be?

4. Consider how you are going to fund either yourself or your venture. You probably have enough resources to retire but do you have enough to invest in a business? What if it doesn’t work? Can you kiss it off? Be careful what you commit to! I have seen people put money into businesses and then end up cash poor when the venture fails.

5. Answer this question: Am I a lifelong learner? In Thomas Freidman’s latest book, “Thank You for Being Late,” he talks about lifelong learning as a necessity. These days, it is increasingly difficult to keep up with ever-evolving technology and the explosive pace of change. How do you feel about climbing back on board today’s technical and societal merry-go-round? If you do decide to do it, I predict one of two things will happen: you will get excited about the rate of change and the challenge of learning more every day OR you will hate it because you will always need to be moving more quickly than is comfortable just to keep up.

6. Measure your desire to manage people. I have heard people say, “Business is great, if only I didn’t have to deal with people.” This doesn’t mean you shouldn’t go back into business but it does suggest that you need to choose that business wisely. Do you want to consult where you are providing a service on your own, or do you want to provide both products and services that require significant staff?

7. Think about how well (or poorly) you are prepared to deal with today’s changing workforce. Millennials behave very differently than Boomers. This does not mean that one workforce is better than another. They are just different! Millennials bring their own skills and desires to the table which can seem foreign to those of us born before 1980 (or even before 1950). That said, you need to recognize and understand their distinct way of working and have a plan for how you will motivate each generational group under your charge.

So, you have some serious thinking ahead of you. My one key piece of advice: look before you jump. But if you can satisfy yourself that you can indeed deal with the issues I listed above, I say “good for you” and full speed ahead.


Andrew Simon (Andy) is a Consulting Partner and head of SAMC-Inbound, our Agency specializing in Inbound Marketing. A certified HubSpot Partner, Andy works with companies that need to grow through digital and inbound marketing strategies.

Mr. Simon has taken a series of start-ups through successful stages of development, including most recently Questar Assessment Inc., where he served over time as Founder, CFO, CEO, and Chairman. At the time, it was sold to ETS in March of 2017, Questar was the 5th largest K-12 Summative Assessment Company in the US.  Questar, in 2011, was voted one of the top 50 companies in innovative education by Education Next.  

As a serial entrepreneur, Andy developed and ran businesses in real estate development and did start-ups inside larger corporations including Citibank, Bankers Trust, Norcliff- Thayer, and Lederle Labs. Earlier in this career he was part of a team that launched L’Oréal into the consumer products arena.


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