Our first stop for the day was about 20 minutes away. This was the second time Jim and I were paired up as part of a local program that picked up and delivered used furniture to families in need.

Jim is retired and knocking on the door of age 70, but he’s one of those new-age retirees who isn’t frail or incapable. Truthfully, in spite of his age and beer belly, I wouldn’t want to be on his bad side in a dark alley … if you know what I mean. I think some people are just born tough as a tank.

Despite his hard exterior, he’s easy to talk to and quick with a joke and a smile. As we drove along, I casually mentioned that I teach and write about retirement and, being curious to hear how people have adapted to post-career life, I asked him if he had any insights.

“No, not really,” he replied, adding “Everything is great … wish I had done it sooner.”  This is where my social worker background comes in handy. I merely responded, “Hmmm,” and waited.

One of the best things I learned as a social worker doing individual, family and group therapy is to be comfortable with silence during a conversation … and to use eye contact to encourage further discussions.

If you can picture me listening to his response and then saying, “hmmmm,” but not glancing away … it quickly creates a desire to fill the space … and that’s usually when the juicy details come out.

I said nothing further but looked at him intently; then he dropped a bomb; something I had never heard before in all my time helping people plan for retirement.

“You know,” he said, “there’s one thing about retirement I can’t really put my finger on. It’s the guilt I feel over getting a check when I didn’t earn it.”

I’m pretty sure my entire body snapped toward him as I blurted out that famous line from the TV show Different Strokes, “What choo talkin’ ‘bout, Willis?”

I just couldn’t comprehend what he said because, despite all my prior conversations and experience, I had no reference point for this mind-blowing remark. How in the heck can you drive yourself to the same job at the same place for 40 years, work hard, never take all your vacation or allotted sick days, and then feel guilty each time your monthly pension check arrives?

Think about what he said. He feels bad because he’s receiving money for doing nothing; something that goes against everything retirement is supposed to be. Something many might classify as one of retirement’s biggest sins. Unless of course, retirement isn’t just about money.

I began to realize that our short time together had created a safe place for Jim to have a real conversation about what he really felt in his heart and mind about retirement. Many people never actually find the freedom to express those thoughts and feelings, and I believe it’s one reason why some clients struggle to make a successful transition into retirement.

There are a host of feelings clients are likely to be experiencing as they transition from work life to home life.  Some are pretty common and acceptable, but those that are more difficult to assimilate, or even taboo, rarely make it into retirement planning or conversations. These unvoiced feelings may not be held by everyone, but they’re very real nonetheless. 

It’s one reason why I compare the concept of retirement to a massive iceberg in that much of what really goes on mentally and physically for people lies below the surface, out of mainstream discussion.

Another unexpected feeling among newly-retired clients may be the inability to utilize their company’s brand name, or their former work title, to get things done or to solve problems. Once upon a time, a phone call that started with, “This is Bob from Ford headquarters” or “It’s Carol at Bank of America” or simply being introduced as the senior VP, CEO or CFO might have gotten people to jump or quickly offer their help. But the significance that brands and titles carry in the workplace often evaporate in retirement. 

We live in a “what have you done lately?” society, where the past has diminishing value. Now, all of a sudden, you’re just Bob or Carol retired. Saying you formerly ran a department, business or were part of a special project team now wields about as much clout as winning the 8th grade science fair or being homecoming royalty in high school. 

Once again, it can be a mindset that chips away at a client’s self-esteem and perception of oneself. These folks may not have realized the extent to which the role their company or their title may have played in their work persona, but for certain they are now saddled with the need to figure it out and move on with a happy face. 

Still another rarely disclosed feeling is that of isolation. How many times have you asked a client how they we’re doing and gotten the reply, “I’m feeling lonely … like no one wants me around”? Too often, this kind of mental anguish is given little credence because everyone thinks retirement is the “promised land”, where you only have to care about your golf score or the time of your spa appointment. Yet, there they are, feeling down, unaccomplished and all by themselves. 

Mindsets like these seem incomprehensible to people still working, or to those who haven’t experienced them. But they occur frequently, and for a number of reasons. Work creates self-worth, physical and mental exercise, friendship and sense of belonging. 

So what can advisors do to help people overcome these feelings and mental challenges? 

Step One: Validate their thoughts and feelings. Whether your client is experiencing one of the cases presented here, or something completely different, letting them know that there are things about life in retirement that aren’t easy, or don’t meet preconceived notions, can be a major relief. That sounds elementary, but retirement is one of the least understood phases of life. There is so much hype about what it can be that people often forget to look behind the hype.

Step Two: Create space and freedom for people to tell you what’s going on in their life. Don’t overbook your time, or try to see as many people as possible in a day. Make time for people to stay a little longer and for conversations to wander outside the confines of the financial stuff. Be curious about what’s happening with them, and use questions like, “If you had to start retirement all over again, what would you do differently?”

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