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The Dark Side of Retirement For Workaholics

This is the article I needed and couldn’t find in 2012 when I “retired.” You know that wonderful thing everyone looks forward to and works towards for decades? No one talks about the dark side of retirement, particularly for workaholics. The confusion. Guilt. Self-esteem upheaval. It’s not all Winnebagos, puttering in the garden and garage saling … or whatever it is retirees do nowadays.

I got lucky. I’d only been in the workforce for twelve years when my husband and I decided to dramatically overhaul our lifestyle and expenses so I could “retire” at the age of thirty-two. You would think it would’ve been wonderful. Well, it was…and it wasn’t. I discovered a dark side to retirement and no one seemed to understand. There were no articles to guide me through it.

Like it or not, your career forms a huge part of your self-esteem (and identity). This is true of everyone, but especially true for workaholics. Money is only a perk of our job. The biggest “take home” is the positive identity and self-esteem we get from being good at what we do. There’s an element of what I call “Living Symbolically” in a workaholic’s employment that goes way beyond the paycheck. I used to live for my co-worker’s saccharin compliment, “You’re the best!”. It felt good. Cheap, but good.

After retirement, it may not feel right to not have to work so hard. It can feel downright wrong to have so much free time. How do you cope with that false guilt? What will you do to fill all that free time? How will you still feel good about yourself as a person when your chief source of that self-esteem, your job, is terminated with a party, a gold watch and a few tears?

Workin’ 9 to 5
What a way to make livin’
Barely gettin’ by
It’s all takin’ and no givin’
Yeah, workin’ 9-to-5 may not be happy, but like false guilt, it’s familiar and thus comfortable. We workaholics know how to cope with it. Heck! We thrive! What we don’t know how to cope with is when that make-believe ship Dolly Parton sang about actually comes in and we can retire.
As I see it, there are three kinds of careers.
First is the one that’s chosen carefully and followed out of passion. A career that truly fits your God-given skills. People in passionate careers are blessed!
Second is the career one falls into from a need to make money. It’s not in your DNA. You may not even particularly like it. But you’re good at it and it pays the bills. Meanwhile, you maintain a separate life and a separate identity outside of the 9-to-5 grind.
Third is the “impressive” career one is pushed into by a narcissistic parent living vicariously through you or a parent who wants to look impressive to their friends and family via your impressive career. You’re just a Little Lego Project. Your desires don’t matter. The self-esteem your good job or elite career gives you, and thus them, is what matters. It’s easy to become a workaholic when your career is your chief (or even only) source of self-esteem and approval from others, especially our parents. It’s downright addictive.
Like so many children of narcissists, I joined the workforce because that’s just what good, responsible people do. There was no real master plan, none of Thoreau’s “living deliberately.” Apart from getting the opportunity to choose a Technical College program I truly enjoyed, Graphic Design, the rest felt scripted and automatic. Go to school. Get a job. Work. The End. That’s what Good People do. I felt plugged into the workforce like I felt plugged into school. That’s just what you do.
Money aside, the workplace was my Life. It was my Self-Esteem. It was my Identity. Most importantly, it made my family so damn proud and their approval formed my self-esteem. This was brought home to me during my first week at my first post-college job. As luck would have it, I accepted a Magazine Graphic Designer job with a very weird boss at an even weirder company. Every day I came home with splitting headaches. Vividly I remember Mom standing over me, desperation in her eyes, yelling at me.
My career at school and my career at work made my family so, so proud. Where once my crayon drawings were magneted to the family refrigerator, it felt like my spreadsheets now hung in their place. (More about that here.) Like school, employment seemed like just a lot of boring worksheets and grubby form-filling. But this time, they paid me to push papers and do spreadsheets. That almost made me chuckle.
The need to make everyone proud and thus feel good about myself was so strong I never allowed myself to realize, let alone verbalize, how unhappy I was at the job I eventually quit. My family was shocked when I quit. “I thought you like it there,” Grandma exclaimed. Let’s just say, the CFO was so abusive, H. R. would not allow him to hold a meeting without a representative from Human Resources sitting right next to him, monitoring his every word. I ran on fear, anger, adrenalin, sugar and my addiction to praise and making my family proud of me. So when I quit after eight years, there was the tremendous sucking sound of a vacuum. My self-esteem circled the drain and disappeared with the career I’d just flushed.
Retirement is supposed to be rosy and wonderful, so why did it seem kinda-sorta hellacious? No one complains about retirement! So why did I feel so bad? It felt wrong to be free. Wrong to have free time. Wrong not to be rushed off my feet from morning til night.
But why!?! I didn’t know…yet. I never realized that not only was I a perfectionist, I was also a workaholic.
The Dark Side of Retirement For Workaholics

Lenora Thompson

Lenora Thompson is a syndicated Huffington Post freelance writer and food blogger. Her readers call her the "Edward Snowden" and "Wikileaks" of narcissism because of her no-holds-barred-take-no-prisoners approach to writing about narcissism. “Narcissism Meets Normalcy” is the real-life, ongoing story of her healing journey from being held “hostage” by a multi-generational, cult-like narcissistic family. It's gritty and real, bloody and bruised, humorous and sarcastic. Lenora Thompson considers herself a “whistleblower,” shining a spotlight on narcissistic abuse so others can also claim their freedom and experience healing. To learn more about Lenora, her husband Michael's heroic battle with Pulmonary Alveolar Proteinosis and to read her writings about food, please visit Thank you!

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APA Reference
Thompson, L. (2019). The Dark Side of Retirement For Workaholics. Psych Central. Retrieved on December 7, 2019, from


Last updated: 28 Jan 2019
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