Zest! / AFTER WORK

Reflect, regret, reset

It’s natural in retirement to mull over things we’ve done—and left undone—in our lives. What’s important is to learn for the future.

By Dr Jon Glass - 3 min read

A little about Jon

Dr Jon Glass runs retirement coaching business 64PLUS (The opinions expressed are those of Dr Jon Glass and 64Plus. Russell Investments does not endorse, and is not accountable for, any views expressed by Dr Jon Glass or 64Plus.) He coaches individuals to a clearer understanding of the issues they will face post work. He has studied counselling and coaching at The Australian College of Applied Psychology and The Institute of Executive Coaching and Leadership.

I bet you’ve heard these sentence-starters: 

  • “If only I had…”  
  • “If I knew then what I know now…” 
  • “I should never have said…” 

We’ve all heard them, and most likely used them ourselves more than once. These are examples of how we begin to express regret. What do I mean by regret? I like the dictionary definition:  

“Sorrow or pain due to reflection on something one has done or left undone.” 

Regret encapsulates: 

  • Negative emotion, 
  • Action carried out, or action not carried out, and 
  • Thoughts after the fact. 

As we move into retirement it seems only natural that there is more time for reflection, and regret.  

Why should we reflect in this way? After all what is done is done, isn’t that true? Well, to be frank, no. Regret can teach us valuable lessons.  

Regret after work 

Best-selling author Daniel Pink has written extensively on the deep structure of regret. He presents a four-part framework for understanding regret, which we will use to gain more precision with our regret sentence-starters (see table below).  

Connecting Pink’s framework to the concept of needs and wants (a tool I find useful when working with my retirement coaching clients), each statement reveals deeper unmet needs. 

1. “I wish I’d done that work…”  Apply this sentence-starter to the person who took piano lessons at an early age but then gave up. In this I hear an unmet need, along the lines of: “I’d love to be able to play now, what a shame”. 
2. “I wish I’d taken the risk to…”   This regret has a different flavour. Think of people who never took those big risks in their careers and then ended up dissatisfied with their progress at work. I’m sure you’ve met them and heard them as they recite their grievances. The unmet need here is one of personal growth through self-challenge: there’s more to give or do. 
3. “If only I’d done the right thing…” 
This is probably the least common regret, but it can and does happen. Most of us never carry out a heroic act. I certainly haven’t. But I have witnessed bullying and I can look back on such an episode and ask why I didn’t do more to stop it. Surely this offends my personal need to act morally. 
4. “Why didn’t I reach out…” 
Let’s face it, we can only have a finite number of friends while family is just, well, family. A common regret occurs when you lose touch with someone whose friendship you valued, yet you can’t easily re-animate that relationship. Can we call this a need for personal connection or love? 

Action vs inaction 

Psychologists tell us that we regret our inactions much more than our actions. Why so? At least with action we tried, even if we failed. With inaction the hum of “I wish I’d….” rings in our ears. There is a message here for those in, or about to enter, retirement. 

It make be too late to study for that final school exam or to change jobs in mid-life. But you can interrogate yourself to discover the reasons why you didn’t succeed as well as you had hoped. Maybe others failed to give you critical information at the time. The lesson for your future could be to enlarge the scope of information you take in before you make a decision. 

And what about reaching out to an old friend whom you haven’t seen for years? It may not be too late. 

In retirement, I contend that it’s important to understand your preferred personal mix between stability and growth. Some needs will relate to self-preservation and stability—such as adequate income and a good family life. Others relate to new experiences and growth—think travel and new hobbies. What works is up to you. 

Regret is part of life and can emerge more strongly in our later years. Take advantage during the 10,000 days of your retirement to reflect and discover what any particular regret is saying about you. If you listen, you will hear the answer.  

Finally, don’t be too hard on yourself: regret is part of life. 


The views and opinions expressed in this article are those of the author and do not purport to reflect the views and opinions of Russell Investments.

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