There were two situations in the past two weeks that illustrate the need to plan for The Other Side of Retirement. This is what I refer to when I give presentations or write about the non-financial aspects of retirement. It is the areas of our lives that are often not discussed or planned for as we approach or transition into retirement. These areas oftentimes sneak up on us and we aren’t even aware of what is happening.

Situation One: My wife and I received a letter recently from one of our neighbors. He was letting people know about his new career as a real estate agent. Since the letter has been disposed of and I don’t have the exact wording of the letter, I will paraphrase his message along with my observation of his situation. The description may resonate with you or someone you know.

Our neighbor had a long career with a Fortune 500 company. His kids were finished with college and now living on their own. His wife was a stay-at-home mom. Retirement had come early for him, I would guess he is in his late 50s or early 60s. I am not sure if the retirement was voluntary or not or if he had thought about what he would do with his time prior to retiring.

His letter explained that after less than a month of being “retired” he found himself bored and wanted (needed) to find something to do. Wanting to use his experience in sales and working with people, he had decided on selling real estate. I am not sure what other ideas he had to keep busy or what his process was for deciding what to do. He did mention that he gathered a “ton of information” before deciding on selling real estate.

The key points from this situation are:

1) Don’t wait until you retire to decide what to do. Plan what you are going to do to occupy your time and what your new identity will be. This can take some time (months or years) to consider options, get any education or experience needed and decide on a new direction. Who will you be and what will you do when you retire?

2) Have a plan in case your company chooses your retirement date, or you are fed up with your career or the work you are doing. You probably won’t find the same type of position (title, salary, etc.) that you currently have. What would you decide to do if you were laid off tomorrow? How would your transition play out over the coming weeks and months?

3) Decide if you need to work for money or want to work to stay busy, relevant and/or connected to others. Will you work in retirement? Would you work for money or for other benefits?

When considering the questions above, keep in mind three things that could change your answers to these questions. First, since the transition into retirement takes some time, it is OK to (and you should) take some time to separate from your former career before deciding what to do next.

Second, your time in retirement could last 20-30 years. That’s a long time! Find something you enjoy doing since it may be something you will be doing for a while. If your next career could last 20 or more years, make sure it is something you will pursue enthusiastically. It may not be one thing- it may be a number of varied activities such as a combination of working, volunteering, hobbies and leisure activities.

Third, keep in mind that the energy you have in the early part of your retirement likely will not be the same as it will be later on during retirement. Find something you can do that won’t require the same amount of energy or that you can cut back your time doing.

Situation Two: My wife is searching for a new job. As part of her networking she reconnected with one of her former bosses and decided to get together for coffee. When they met, her former boss asked what I had been up to. When my wife explained that I was a retirement coach helping people make the transition into retirement, he responded how important this is for people. He told her about a former colleague of his who had retired about a year ago. He was struggling with the transition and had developed a habit of drinking heavily.

Although this may be surprising to some of you, it wasn’t to me. I have heard many similar stories of people spiraling downward due to developing addictive habits or thoughts of hopelessness. When we transition into retirement, we need to have something to fill our time, something to give us purpose and a motivating reason to get out of bed each day.

When we don’t have a purpose, one thing that can happen is people fall back on destructive habits that consume their thoughts and time- it could be alcohol, but it could also be drugs, depression or suicide. These are called the “dark side of retirement.”

The key points for others at this same point in their lives are these:

1) It is important to find activities to occupy your time in retirement. If you don’t, bad habits can overtake your thoughts and actions.

2) The dark side of retirement is real. Keep an eye on your retired friends, neighbors, former colleagues for signs of unhealthy habits. The key is to make people aware of these habits before they occur. Once it takes over someone’s life, it is often hard to intervene.

It is hard to hear stories like this because they happened in a relatively small circle of people I know. There are hundreds of thousands of other people going through these and other similar situations as they think about and transition into retirement. Take the time to formulate a plan for how you will make a successful transition into retirement. Point these people in the direction of a retirement coach or other professional who can guide them toward a positive retirement.

If you need help with your transition, please contact me to set up a free initial phone call. To learn more about The Other Side of Retirement, visit