When to Retire—the Big Decision

So, you’re not yet retired, but you’re trying to decide if and when. How are you going to make that decision? What if I told you there were four simple, yet profound, questions to ask yourself, and when the answer to all four of them is “Yes,” it’s time to retire?

How powerful are these questions? In a retirement life-planning workshop a couple of years ago, we were covering these questions and how they could be used to make the retirement timing decision. We got through the module and were about to move on to a new topic, when we heard a woman scream from the back of the room, saw her stand up, and listenen as she hollered, “I’m outta here!”

She had been struggling with when to retire, and her financial advisor had been trying to convince her she was ready. But neither she nor the advisor had a framework for thinking about it. Now she had one, and her path was clear. For her, the answer to each of the four questions was “Yes.”

I’m not expecting anyone who reads this post to have the same spontaneous reaction, but you never know. Here are the questions.

Questions 1: Do I have enough?

This is the financial question—important, but many make the mistake of having it be the only one they consider. Although it is not absolutely necessary, finding a trusted resource, like a financial advisor, can help you develop your answer.

We remind people that financial security is not about the size of your nest egg, but rather it’s about making sure that you have matched your lifestyle to your available resources. Spend time developing your budget, then integrate it into your financial plan.

Questions 2: Will I have enough to do?

Another way to pose this question is, “Do I have a written, holistic retirement life plan?” Refer back to my earlier post that identified the “3-P’s” of preparing for retirement, Plan, Practice, Partner. Consider this additional “P”—Portfolio.

Just as your financial advisor will strongly suggest that you diversify your financial assets into a portfolio of investments, so should you have a portfolio of meaningful things you are looking forward to doing in retirement. Do you have such a portfolio? Is it written down to increase the odds that you’ll follow your plan?

Questions 3: Have I had enough?

Some people choose not to retire, because they remain passionate about their work. That may be true for you. Do you jump out of bed in the morning excited about your work day? Or despite having had a long, fulfilling career, have you lost your edge? Is going to work and making it through the day just not as motivating as it once was?

Questions 4: Does my spouse, partner, or someone else close to me want me around 24×7?

Having worked with hundreds of couples, we’ve learned that many retirements fail because there is no understanding of or alignment with each other’s dreams and plans. This is why we urge every pre-retiree to a) identify those closest to you who will be affected by your retirement, and b) have the “crucial conversations” with them.

The crucial conversations, available on our web site, will help you gain alignment to your retirement plans. In fact, for couples, we urge that each partner have an individual plan, and the couple also has a joint plan. And, given that many retirees are not in a couples situation, we emphasize that you engage with anyone who will be impacted by your decision to retire to ensure there are no issues you’ve not considered.

Typically, once the crucial conversations have taken place and there is alignment to the plans, the answer to question 4 should be, “Yes.” Have you had these conversations?

We don’t urge people to retire, but if your answer to each of the four questions is “Yes,” what’s holding you back?


  1. I’vebeen planning retirement since I got my first job at the age of 12. I retired at 38; in 2004. At 49, I bought my own business; it’s seasonal, and I’m the boss. It’s great. I’ll do this for 2 or three years then sell. The only negative is that my yard work suffers, and my dogs miss me when I’m away.

  2. retirement communities Scarborough

    December 16, 2015 at 2:35 pm

    Your post is really amazing . I enjoyed reading through your post. Please keep sharing this kind of work with. Just be sure you are emotionally ready to quit working if that time will come.

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