To Retire or Not to Retire, That IS the Question….

Wendy Fisher
7 min readOct 31, 2019


The Retirement Decision is a BIG Decision!

Do I retire or do I continue working? The Retirement Decision is a BIG Life Decision!

Is this an emotional decision? Absolutely!

A few lucky folks can easily walk out that door, and never look back… they had employment issues, disliked their new younger supervisors, totally done with new technology changes, didn’t agree with the company’s new direction or philosophy, or they were simply burned out from a lifetime of work.

Maybe it was simply a job and they were eligible to retire, it’s not an emotional retirement decision, out the door they walked — Financially ready or not!

Others were “forced out” for a variety of reasons: layoffs, downsizing, management decisions. These folks have to somehow make peace with not having made the decision themselves because someone else forced them into retirement. This is a VERY emotional retirement beginning, as it’s not your decision. This happens a lot — only people assume “it’s only me being forced out”. They begin retirement on a bad note thinking, I’m old, they don’t want me anymore. Seriously?

Then there is me, and many of you out there — who simply have to decide whether to Retire or not. Sounds simple when you are younger— but when it’s YOU, and YOUR retirement, and YOUR life — the emotional retirement decision is difficult!

Many of us have a hard time with this decision — it is a very challenging time of life and time of life-changing decisions that can impact the rest of our lives.

My Retirement Story

I personally struggled with the retirement decision for over three years… in the end, I retired five years after I was eligible.

I told co-workers I’m not sure if I’ll retire in 2 weeks, 2 months, or 2 years, and I was honestly not sure. It’s not really financial — I am lucky enough to have a pension and health care (though the latter is never guaranteed for life anymore), and retirement savings. I worked in the retirement field and took this phase of life seriously.

Here are a few questions that I might ask someone who is struggling with this emotional retirement decision (and my own personal answers to these questions). If you are struggling with the big decision — ask yourself:

Do you like your job? Are you helping society? Does your employer need you? Are you filling some purpose in your employment or community?

Yes, I love my job as Retirement Manager, as I help people through the initial struggles of retirement decisions. Person by person, one by one, I walk them through the financial decisions of pensions, health care, Social Security, IRA’s, etc. I’ve helped thousands retire and that feels good.

I often asked, “How do you know you are ready to retire?” They always said, “You’ll know when you are ready.” WHAT? How will I know? Now it wasn’t one person who said this — many did! WHY did they all have the same answer? Will a tiny Retirement Fairy sit on my shoulder one day and whisper “It’s time!”

I also asked many, “What do you DO all day?” I couldn’t imagine just sitting there all day, doing little. Retirees always tell me they are busy, but cannot tell me what they do! What the heck? How do days fly by and you can’t tell me what you were busy with?

Finally, I also had guilt over those I might leave behind. If I retire, who have nobody to guide them, nobody who cares… and yes, I realize that Anyone, Anywhere, is replaceable. I was replaced, but I was also right — nobody cares. It is what it is.

What are the negative aspects of your work, your employer, your co-workers? Tell the truth, no sugar coating your job here… The grass is not always greener in retirement.

I work in a political environment, and that’s rarely a good thing. My department is, for the most part, for the employers benefit — and rarely do my co-workers think about the employees viewpoint. To me, this person is giving their time on this earth to support the employer. Yes, I realize they get paychecks and benefits in return… but every employee should deserve some respect, regardless of the occupation. These are folks who bring their mind, souls, sweat and tears to the work place…

Management changed. I think this happens to many new retirees… nothing is suddenly the same. People you worked with for decades are suddenly gone. People who supported you, gone. New management brings changes, both good and bad. In the end, you must choose to support these changes, or retire.

I have a list, two columns, the positive and negative aspects of my own retirement… hey, do I hear you snickering? I really do. I had to actually write them out, and have continued, for three years, to add to the list. It helps me focus on both the positive and negative of working and the concept of my own emotional retirement — try it. Your own thoughts might surprise you!

WHY do you want to retire?

I’ve worked 37 years with the same employer, crazy dedicated to my job. I never took a leave of absence, only once taken a two-week vacation. Finally, I’m not willing to change my job into what new managers want.

I’m also ready to take on new challenges in life… my websites! Fun Fun!

WHAT will you do all day?

I know that I need to be busy. I’m already busy as I work full time and do website projects after work and on the weekends, and I need to continue this into retirement.

I have plenty of interests. I’ve collected craft supplies for twenty years in the hopes of finding the time to create! Now, I can use my creative energies, finally!

I have websites that I absolutely love working on. They keep my brain challenged and I love the interaction with retirees and the retirement topic itself. My website work is a huge challenge — and I love that!

I may work part-time or volunteer for the church a few days a week, I honestly don’t think I’ll be bored… however, the initial depression that often follows right after retirement does worry me.

Are you financially ready for retirement?

Yes. WOW — I said it, I am….. Maybe.

How does anyone ever know they are financially OK for the rest of their life? I’m age 53 — If I live forty years, to age 93, maybe finances are tight — my pension is stuck at a 40-yr-old rate, my savings long gone… but do I care any more?

Even if I’m lucky enough to have a 30 year retirement through age 83, am I ok? Who knows?

When is enough enough? You’ll never know until life plays itself out — what is your life expectancy (how long did your family members live? though that isn’t necessarily the key), how long will you live (based on how you take care of your own health), what financial emergencies fall into your life, inflation, family… just so much more than we can hardly imagine.

Decisions, decisions… Emotional Retirement Decisions!

2019 Retirement Update:

I retired in 2010, two years after this was written. I retired in April — and just like many retirees told me, I knew it was the right time. Oddly enough, on the way to work in April, blossoming flowery trees made me think about RETIREMENT. I suddenly wanted OUT after 37 years with one employer. I walked into my supervisors office and announced I was retiring in two weeks. This in itself is odd — I always knew I’d give a month notice, always — and suddenly even that didn’t matter. I was done.

It really took me 3 years to get into the retirement groove… and I KNOW retirement. It takes time to slow down in life, to find a contented lifestyle, to find yourself again. Time flies by and yet you’ve done little… and this is disconcerting to say the least (and likely the very reason that retirees couldn’t verbalize how they kept busy).

What I neglected to list under What Will You DO All Day? — playing the caregiver to my parents. My mother is 93 years old, Dad is 91. For almost ten years now, I’ve visited them daily to help with small chores, lunch meals, doctor appointments, and a whole lot more. They were in their mid-80s when I retired, still driving and I didn’t even consider this caregiver role — MAJOR part of my life today!

The Lesson: Retired Life cannot be totally planned, just like any other phase of life. LIFE itself gets in the way. Life shifts here and there and you adapt.

In the end, after the big retirement decision, you will find yourself. You will seek out new lifestyles and find pleasure in the small things in life, as well as new adventures that motivate and inspire you!

I hope and pray you will benefit in some small way with my own retirement decisions!

P.S. My websites survived the first ten years of retirement and I invite you to visit me at

Originally published at



Wendy Fisher

Struggling with Retirement? Retirement Enthusiast & Coach here to help! Retirement is complex, full of decisions — but Retirement ROCKS!