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6 Retirement Questions to Ask Yourself

| May 13, 2019
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Do you really want to retire?

Not long ago, I had lunch with Charlie, a 63-year-old business owner from East Caldwell, New Jersey. Because he knew that I was in the financial services industry, he peppered me with questions about retirement and his pending plans to sell his business. He didn’t seem like he was completely committed to the idea of retiring, but there was a sense of inevitability to his departure from the workforce.

“I have run my business for the past thirty years,” he told me. “In that time, I have watched it grow to the point that we have annual sales of over 10 million dollars. I get up every morning at 5 AM and get into the office by 7 AM. Most of my time now is spent with my customers and I have great employees who actually handle the day-to-day operation. In fact, two of them have made me an offer to buy me out.”

When I asked Charlie what he would miss most about his work, he talked for five minutes about the various parts of the business that meant the most to him. However, when I asked him about why he actually wanted to retire his answer was very short: “Because it’s time, I guess” he said.

Today many Americans are also thinking about their retirement plans and looking to the end of the working chapter of their lives. My experience in counseling them tells me that far too many don’t actually want to retire but have accepted it with the same inevitability that Charlie had. I am not saying that people shouldn’t retire, or that being in retirement is such a bad thing. However, I feel that you should be very clear on WHY you are giving up your work career and have an understanding of what you are actually retiring TO.

Here are six questions that I pose to people who are trying to formalize their retirement move:

1. Why are you retiring?

This may sound like it has an obvious answer, but in far too many cases the reason that people retire is based on a misconception about what retirement actually is. If you are retiring because you have reached your company’s retirement age, or your pension plan makes it worthwhile, this is understandable. However, if you are retiring simply because you think you should, then perhaps more thought might be directed towards your answers to the next five questions.

2. What is it that you will miss most about your job?

Most people gain some satisfaction or take positives away from the workplace. As you think about what you are giving up when you leave, what are some of those motivators that you will also be giving up? Work plays several roles in your life. For most people, work is a source of financial comfort. Work may also provide status, fulfill the need to be needed, give enjoyment from creating ideas, and even provide structure to your daily life due to its responsibilities and deadlines. And, don’t forget about the social connections that work provides. Some or all of these may apply to you, and it is important for you to identify what you feel you will lose in your life because you are not working. By the way, if none of these motivate you about your job, you should probably look for something else anyway!

3. How will you replace the things that you liked most about your work?

One of the keys to retirement success is replacing what you will miss most about work in your retirement. Answering the previous question should help you identify the things about your job that really motivate you. The next step is to consider how you will replace those things in this next phase of your life. If you like work because it provides you with a sense of status, you might consider working on a board of directors or even starting a business. If your work provides you with a sense of utility, then volunteering might be in your future.

4. What are you looking forward to the most about your retirement?

Since it is so important to understand what you are retiring to, you should think in terms of what you want this next part of your life to look like. It’s normal for most people answering this question to focus on the places they will go or the things that they expect to do. That’s why I call retirement the “30-year long weekend” because that is how many people think about it. I like the concept of a “bucket list” simply because it forces you to write down your life goals so that you can create the plans to make it happen.

5. What are the opportunities that you see in your retirement?

Think beyond the leisure activities that you are looking forward to. Instead, consider the kind of life that you want to lead, the values that will drive you, and the opportunities and accomplishments that you want to undertake. Your retirement life is a tremendous opportunity to do new things, go to new places, self-actualize, and live the life of your dreams. Figure out what your big goals are for retirement, then set out to create a plan to make those things happen.

  • Do you want to travel?
  • Spend time with family?
  • Volunteer with an organization that's important to you?
  • Remodel your home - or downsize?

6. What areas of your retirement need a plan?

Most retirement plans are financial plans and in a lot of cases they simply focus on building a nest egg that is big enough so that you won’t run out of money. If you really want to clarify your vision of the future, your goal setting and planning has to go beyond planning your money—in fact, I am going to suggest that you can’t realistically plan financially unless you have a vision for what you want to accomplish in each major area of your life.

I don’t want to tell people how to retire, but I do want to point out the opportunities that this new life may provide. In Charlie’s case, he still wanted to find ways to stay involved in his business but to allocate more time to travel and volunteer. He is still going to sell the business, but he has negotiated with the new owners to stay on and work on a part-time basis handling customer relations. I simply asked him these questions and helped him frame his vision of the future. Now he has some clarity around his opportunities and the framework for a plan.



Joseph Falbo, CFP®, CRC®, AIR® is the founder and President of Falbo Wealth Management in Murray Hill, New Jersey. With over two decades of experience, his main goal is to help preserve and grow his clients’ wealth so that they can live their entire retirement with dignity and independence. FWM works with individuals, business owners, senior executives, retirees and their families who work toward financial success. Learn more about them at falbowealth.com.

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

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