May 30, 2023

More of Your Retirement Stories --- Part Four


In what has become a series of posts that I am glad I pursued, here are the answers to some of the retirement questions from long-time reader, David D.

Who was the greatest inspiration/mentor in your life?

I have to say none come to mind.  My father was relatively uninterested in raising me and critical of most things I did. I think he felt that it was to “toughen me up”.  Probably a good thing in his mind as I think for him life was a tough go. It didn’t work of course, and it mostly taught me to keep my head down and don’t make waves. 

At school I found that the “keep your head down and don’t make waves” kept the teachers off my back too whether I did my work or not-- it’s easy to ignore the quiet kid in the back. With my mother everything I accomplished, or didn’t, was fine with her which I think she did to sort of compensate for my father’s approach, but it wasn’t exactly motivating. I felt that in my father’s eyes everything I did was wrong and in my mother’s eyes everything I did was right. 

The greatest inspiration or mentor in my life? I can't think of anyone. I dropped out of school at 16 and about 10 years later after lots of night school classes while completing an apprenticeship and holding down a full-time job in the trades I went to university and paid my own way. No one inspired me or mentored me to do that, I just figured it was something I wanted to do so I did it.

What were you taught about money and finances in your youth? How has that advice changed as you got older?

I wasn’t really taught about money, but I had two opposing role models. Both my mother and father were raised in the depression, but each seemed to take different lessons. My father watched every penny his entire life, he was cheap with himself and others. “Money is hard to make and easy to lose” was his motto. 

That sounds good I suppose but it was really hard to get anything out of him unless he wanted it. He had my mother on a very strict budget for groceries and really everything, it was tough.  

On the other hand, my mother, who had her own job since I was in grade 2, was a free spender so maybe she needed to be on a tight budget, it did mean there was little to go around. I do recall that when department store credit cards first came out my mother had me hide her credit card bill when I got home from school so my father wouldn’t see them.  

One day I forgot or was late home, I don’t remember which, but I do remember the big blow-up in our house and my mother coming to me and asking me why I didn’t hide the bill like she’d asked.  

In any case I developed a sense that it’s a good idea to avoid going into debt and save what you can. When I was older, in my 30s, I bought a daily business newspaper and read it everyday cover to cover. At first, I had no idea what they were writing about but after a year or so I started to get it. 

I also read a book, The Wealthy Barber, by David Chilton which is a classic about saving and investing and that got me going. I still think it’s the first book everyone should read about finances.

What did you think about old age as a youth, and how do you feel about it now?

I remember about a year after I quit school, I guess I was 17, I was with my mother and grandmother. I don’t quite remember the conversation, but it was about working or maybe my grandmother was thinking about retiring and I said something along the lines of “Well I guess working is my life from now until I retire when I can do what I want again”. 

They laughed and laughed that this 17-year-old was already looking forward to the day he could retire. I didn’t know what they found so amusing, as far as I could see it was a true statement. I’d have to be doing whatever my employer told me to do for the next 45-50 years before I would have a pension that would allow me to do whatever I wanted. 

Looking back, I can see they knew I still had my whole life ahead of me so why was I even thinking of retirement, but it seemed to me that that was how it was, I was just stating the obvious. 

Interestingly when I did announce my retirement at my last workplace I was talking to one of my coworkers about my upcoming retirement and he said “I think the only reason you ever worked was so you could retire.”  Thinking back to that day when I was 17 maybe he was right. But I did have a long and rewarding career too so that helped.    

What wisdom has come to you in your advancing years?

People are the most important thing. It’s not work, it’s not money, it’s not power, people are the most important thing. As I have aged, I find that more and more true.  

The government isn’t there to amass and project power or to make a good environment for business, it’s to see that the people are able to live happy and productive lives. Is there anything else that really matters?

What do you miss about your career?

Not a single thing. Zero. Nada. In my opinion my career was a job not a life. My career was something I always saw as a deal with my employer where I traded my intelligence, time, and skills for money. I did well at it too, ending up in a senior management position, but I never considered work to be my “real life”.

Companies don’t care about you. As long as you are making them money it’s good and when you are not, whether due to you or external conditions, they will get rid of you as quickly as they hired you. 

Your family and friends are the ones that care about you, your career does not. One thing I know for sure is that a year after you leave a workplace only a very few will remember that you ever worked there.


Did you have a career that was very satisfying and fulfilling? If you could do it all over again would you pick a different career path?

I think I did have a satisfying and fulfilling career. I liked what I did and was successful at it.  The 10 year diversion between dropping out of high school and going to university isn’t something that I’d advise anyone to do if they can at all avoid it. 

In the end it worked out for me, but I was always career hitting goals when I was about 10 years older than my peers. Such is life but for most of my career my managers were either my age or younger.  It wasn’t a problem for me, but it was something I noticed.


I can say that the last 5 years of my career were not good at all. The company was continually downsizing and centralizing. In fact, I had to switch to another corporate division at age 56 to either stay on or be packaged out of a job. 

My last role there was to outsource all the work and winnow down the local department to zero all while taking arrows in the back from local management. The money was good and at 56 I felt not quite ready to retire, had I been 59 I would have accepted the buyout but 56 was too early for me. 

When the final push came to implement the last program to fully close the department, I had had it and retired.  Let somebody else do it. It was the best decision I ever made.

I thoroughly enjoyed David's recounting of his path through life to this point. He managed to navigate several obstacles in his path while staying true to what was right for him. 

For those of you who are regular readers, you might recognize David as the fellow who reminds us all to enjoy the financial fruits of our work. After several decades of saving, his point is we deserve to enjoy at least some of that money when we have the time to do so. It is a difficult mental switch to make, but I have adopted some of his approaches.

The last in this series will be posted in a few weeks, with my answers to these questions. I am anxious to know what I am going to say!



  1. David, I was in banking in the 80's when a number of banks here in the U.S. were acquiring other banks, being acquired by other banks or going belly up. It was a terribly tumultuous time in the industry. Although I started my banking career in accounting, I was working in Human Resources at the time - the result of a previous merger. The bank I was with, a large federal savings bank, was one of the banks that went under. It was extremely difficult to watch colleague after colleague jump ship or lose their job, and it was painful to prepare their separation packages. Many of us in HR chose to ride it out to the end, some of us out of a sense of duty to see that our colleagues were treated fairly throughout the process. My administrative assistant prepared her own separation package, and I prepared mine after she had left. I know my manager at the divisional level did the same. My point is that I understand completely your determination that enough was enough. I don't think anyone who hasn't lived through that employment situation can truly understand how stressful, painful and demoralizing it can be. I give you credit for walking away, knowing you had reached your limit.

    I have always appreciated your outlook on retirement spending. Until the moment we retire, we live our entire lives under the direction of others. Now, we get to enjoy the fruits of our labor - and our savings - and can do what we want when we want. This is the moment we looked forward to, and Alan and I often fall back on what we consider a critical question: If not now, when? I think your viewpoint and mine are frequently aligned, and I enjoyed reading your story.

    Bob, I am anxious to hear what you're going to say, too!


  2. I have friends who took your life path. Many joined the military for their “break” - including my husband. It was not easy, but I think they are having the most satisfying retirement of all. They earned, they saved, they retired to enjoy!

    The Wealthy Barber. I remember that book. The book that changed my direction was Master Your Money by Ron Blue. Making the Most of Your Money by Quinn taught me a great deal. Bob- maybe asking your readers what their start book would be interesting.

  3. People for whom I have the most admiration? Those who figured it out without parenting and guidance. I find it absolutely remarkable that kids find their way 100% on their own.

  4. What an interesting background and life story. My dad was obsessed with money, too, and my mom lived on the budget he set. I took a life review class in my 40's to process my career and what my next steps would be. As part of that class, I interviewed my dad about his work life. He was always moving to a job that made more money because they kept having kids (Catholic in the 50's and 60'). My mom went back to school to be a nurse when my youngest sibling was a young teen. He finally bought his own business and they did well from that point on. But our upbringing makes for some interesting money obsessions (spending and saving) among my siblings and me.

    I'm also amazed whenever I hear someone say their parent was disengaged. If anything, my parents were over engaged. Makes me wish I could go back and look around me with what I know now and see what my friends' parents were doing/saying to them.

  5. David, thanks for taking the time to share your interesting life story. It resonated with me because it has some similarities to my life. Like you, I was mostly on my own as a teenager, having to figure things out with no parental help. I also never made work my highest priority. My highest priorities have always been mental and physical health, and relationships with friends and family. I took an early retirement offer at age 53, and never looked back.

    Your comments on a number of blog posts about unlearning the savings habit and learning to spend our money has been a valuable contribution to this blog. I remember you saying something like, "The future you've been saving for is now. You're the youngest you'll ever be so spend the money on experiences while you're physically able to enjoy them." I'm also in the "spending" phase of retirement which dovetails perfectly with my philosophy of living my best life and enjoying life to the fullest.

    For example, this year my wife and I were trying to decide between two equally wonderful choices for a 50th wedding anniversary trip. We went back and forth between plan A and plan B. Well, we decided to do A and B. For one of those trips, we will pay all expenses for our children, their spouses, and all of the grandkids. If not now, when? I hope that inspires others just like your comments have inspired me. I hope you will continue sharing comments in the future.

    1. Both A and B - good for you! Congratulations to you and your wife as you celebrate your 50th anniversary. You'll be creating lifelong memories with and for every member of your family. Enjoy every minute - of both trips.

    2. Again, I would like to thank David for his honest and open responses to the retirement questions. His ecperiences are ones shared by a lot of folks but not discussed enough to let us know that childhoods and families come in all sorts flavors and challenges.