Starting A New Business After Retiring? Four Do’s and Four Don’ts

Last month I wrote a blog entitled: “Starting a Business While Working at Another.” I received a terrific response with a large number of reads and “shares,” which prompted me to write this one, offering top tips I would share with anyone trying to start a new business, particularly after retiring. 

So if you are thinking about un-retiring and might be in the start-up mode, here are some critical do’s and don’ts to think about before launching yourself (again).

Four things To Do when you are thinking about going into business again

  1. DO be honest with yourself about your energy level.
    Starting a new company by yourself or even with a partner requires a great deal of energy. You’ve already worked hard your whole life so that you could retire. Do you really want to dive into a full-time job again? If so, great. If no, stay retired! But you need to be honest with yourself about how much you can really handle. Launching a start-up and then only giving 50 percent instead of 100 is not going to lead to success.
  2. DO ask yourself if you can handle a constant stream of problems and stress everyday.
    Start-ups are never easy. Once you are in one, it can be all-consuming and stressful. Issues come up all the time and often there is no “off button.” How does 24/7 sound? Or at least 18/6? This goes along with being honest with yourself about your energy level―if you can’t be there when you’re needed, you should rethink your priorities.
  3. DO determine how much you want to use your intellect.
    One reason people retire and then decide to start their own company is that they are bored out of their minds. If that’s you and you want to keep your mind sharp and expanding, then a start-up might be in your best interest. It can be challenging, but it can also be fun and exciting at the same time.
  4. DO assess how much you want to engage in favorite hobbies and other outside interests.
    Let’s say you love to play golf or tennis, or have leisurely lunches or dinners with friends, reminiscing about yesteryear. Maybe you want to spend a month or two on an international trip. Of course, when you begin a start-up, you can still grab a fun lunch or dinner with someone―but the rest of your time will likely be consumed by the new venture. Are you (and family members) ready for that Perhaps you should speak with your family about the idea of launching a start-up company so they can prepare and give their input as well.
    Four things To Do

Four things Not To Do (which I wish I’d never done)

  1. DO NOT think you won’t be digging into your retirement savings to start the business.
    Start-ups not only take energy, they require money. You need to be “all in” and your spouse Andrew Simon's top tips for starting a new business after retiringhas to know that some of that hard-earned money will be invested in this new and unpredictable venture. Other people besides you might be depending on that money and, at this point, you can’t let them down. So do your best to estimate the investments needed and determine if they’re worth pursuing.
  2. Do not just start a business because you don’t know what else to do.
    If you’re someone who just needs to be busy, maybe you should join an organization that you care about and volunteer your time. That way you can still contribute to society while staying busy. Doing volunteer work will keep you busy yet won’t leave you stressed out investing in and running a start-up, and will still give you something to do with your time that benefits your community.
  3. DO NOT go into a start-up without a driven and practical goal.
    Do you still have that desire to succeed? Do you want to show people that you are still good―maybe even better than ever? Then it might be the time to build a significant start-up. But the first thing you need is a driven and practical goal so that you know exactly what direction you want to go in. You don’t want to end up failing because you didn’t have a realistic plan. Having an original idea is fantastic, but you need to know how to accomplish your plans and make your idea come to fruition.
  4. DO NOT assume you have all of the necessary skills to make a go of it.
    The times are changing fast. What you did yesterday might not cut it today. Certainly there are transferable skills, but you might need to take some online courses to stay current. Are you willing to learn a whole new set of skills? If you have the energy and intellectual curiosity to learn today’s technology (which your grandchildren are already experts at), then you might want to dive into your own business. If the thought of taking on new technology makes you sweat profusely, remain retired.


Some people have been looking forward to retirement for 25 years. If that’s you, beginning a start-up is the last thing you want to do and it could turn into your greatest nightmare. Other people have never wanted to retire. Which are you?? 

If you realize that you don’t want to play golf or travel all your life, perhaps re-launching your business career is the way to go. However, I urge you to seriously consider my four do’s and dont’s before moving forward. It is a new world out there and you need to be prepared to grab it by the horns and succeed.

Need some more reading on post-retirement entrepreneurship? Try these blogs:

To talk about your start-up goals, please gives us a call. Or, read all about our 6-Step Process to help entrepreneurs take those great ideas and turn them into businesses. We would love to share our tips with you and help you grow.

Andrew Simon, Entrepreneurs, Change Management

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