The Road To Retirement: A Mid-Life Crisis? - InvestingChannel

The Road To Retirement: A Mid-Life Crisis?

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The Road To Retirement: A Mid-Life Crisis?

As we continue to grow this newsletter of ours, we’re delighted to see more thoughts and feedback coming in from you. Please use the link at the bottom of this email to interact with us. 

Obviously, retirement is a hot button issue. The way we approached it in last Thursday’s Juice hit a nerve with more than a few readers. 

In Has Retirement Had Its Day?, we learned a few things about retirement from a happiness expert: 

In mid-life, many people start to feel a sense of unhappiness. As the traditional notion of retirement draws near, maybe they find themselves in a rut or feeling burnt out.

We’ve written about midlife crises before, particularly how freaking expensive they can be. That last link right there, by the way, was one of our most popular posts of 2023. While we know that people do certain things — like buy insanely expensive cars — during midlife crises, we have yet to explore why. 

But we might have tied things together without even knowing after Thursday’s Has Retirement Had Its Day? post. So, you might want to refer back to it. 

How did we tie things together? 

  • As Thursday’s post explains, some people feel stagnant in their work during mid-life. 
  • The response we received from readers echoed this thought, but also strongly implied that the road to retirement can be rough — even soulless — adding to the malaise. 
  • Taken together, this adds to the urgency of reconsidering retirement. What it looks like across generations, but especially for those not quite there yet. And if it requires significant practical and psychological tweaks, if not massive overhauls. 

With this in mind, let’s consider some of the feedback we received (lightly edited for clarity), formulate questions from it and work together to answer them via future installments of The Juice and more of your feedback. 

From a reader who didn’t leave their name: 

Enjoyed the words on RETIREMENT.

I am approximately 5 -7 yrs out of retiring and being financially ok.

Will I have my (WELL TRAINED) Lab/Retriever cross fetch me the paper and my slippers for my rocking chair so I can comfortably smoke my pipe and wait for the next visit of grandkids ?


I am going through huge transitions in my business life as well as family and am adjusting accordingly.

Am I presently HAPPY?

Not much, but the pursuit of it lies ahead as always and as an individual I seek pleasures as well as goals in my life without pondering the issues with so many others out there.

Keeping in mind the ones I hold close to heart being (friends and family) I shall be there for emotionally and financially.

Success consists of going from failure to failure without the loss of enthusiasm 🙂

Real talk. But it begs the questions: Does the process of retirement always have to include the notion that happiness — or some vision of a better life — is off on the horizon? Why can’t we have both now? 

Because if you’re grinding through the last few years of your full-time working life, will you have anything left in the tank — physically and mentally — to truly enjoy retirement? 

From another reader who didn’t leave a name (only an email, which we don’t share):

Quit my job at 57. Did not retire, just quit. I was sick and tired of the commute 60 miles each way) and trying to motivate people that did not like their job. I had enough money in my 401k to be able to start drawing from it. I did go back to work but in an entirely different avenue. 

I knew I was going to take social security at 62 so I needed to transition to something completely different from what I was doing. To my amazement there are many jobs that are fulfilling without the 9-to-5 grind. I drove a school bus for 6 years and also was a substitute teacher. I then worked as a bartender and worked at a liquor store for 5 more years. Presently working a# a courier for a local hospital. 

None of these jobs paid much but were fulfilling in their own ways. They keep you busy and give you a purpose to move on every day. I found out that chasing a dollar isn’t all it is cracked up to be. Sometimes all it takes to be happy is to have a purpose in life, whatever it might be.

I am happier now than ever at age 73. No pressure to advance in my career, just show up, do the best you can and enjoy your surroundings. Life is too short to be miserable doing something you don’t want to do.

There’s lots here. Primarily, is the idea of saving $1 million or more by, say, age 65 and quitting work altogether dead? Maybe it makes more sense to save what you can, quit the high-earning job you don’t quite care for in your 50s (assuming this is the case, which it is for many) and then make less doing things you actually enjoy. Between this income, your previously accumulated savings and Social Security, you might be able to carve out a nice life for yourself while remaining engaged. 

The Bottom Line: Definitely lots to chew on. For us here at The Juice, it’s super helpful to hear from you. We hope you like hearing from your fellow subscribers as much as we do. 

In tomorrow’s Juice, we have two more insightful pieces of subscriber feedback that raise super important, if not pivotal and profound questions, around retirement. So be here for those. Because we’ll group the questions from today and tomorrow’s installments and start answering them — together — in the weeks and months to come. 

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