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Retirement – Heaven Or Hell?

Retirement – Heaven Or Hell?

By Mike Drak

Retirement is great during the honeymoon stage. There is nowhere to be, no deadlines, no stress and no pressure to perform. But after a while what at first seemed like freedom, reveals itself as a new form of hell.

There is a Twilight Zone episode called “A Nice Place to Visit” that brings this point home. In it, the main character is Rocky Valentine, a small time thief who is shot during a robbery and passes out. He wakes up and at some point he realizes that he’s in fact dead, but by some mistake instead of being in Hell where he belongs, he’s in Heaven, and has been assigned a guardian angel by the name of Mr. Pip.

Life for Rocky is great for a while as all his wishes come true – there are beautiful women, an expensive penthouse, fancy clothes and all the money he desires. In fact, every time he goes to the casino, no matter what game he plays, he wins: he can’t lose. But eventually Rocky gets bored of the predictability of his life, the excitement is gone and with that all of the fun.

Finally Rocky can’t take it any longer and pleads with Mr. Pip to send him to the other place where he belongs and that he doesn’t deserve to be in heaven. At this point Mr. Pip says “Whatever gave you the idea that you were in heaven? This is the other place!”

The lesson here is that Rocky goes crazy because there are no challenges in his life, no effort required on his part and there’s nothing to hope for because it all exists as soon as he wants it.

Sounds a little bit like those retirement commercials the advertisers keep showing us doesn’t it?

We’ve been conditioned by the advertisers to think of retirement as the payoff for all our hard work, a life of endless leisure where everyone lives happily ever after.

But the reality is that just like in the Twilight Zone episode any retirement based solely on sitting on a beach somewhere drinking Margaritas all day usually ends in boredom and boredom can be a living hell. There is only so much reading, watching TV, shopping, traveling and visiting friends that a person can handle before they start feeling a little antsy. Even in retirement, in order to be happy we need to be constantly challenged, and not just by trying to hit the longest drive.

And it’s not just boredom that we need to be concerned with as Retirement Hell comes in many forms;

  • Working so many hours to earn money and take care of your family, but now that you are retired and have time to spend with them they don’t care to be near you.
  • Getting divorced late in life.
  • Living with someone that you don’t like and who doesn’t like you for the rest of your life.
  • Your TV is your best and only friend.
  • Living with regret.
  • Being forced to do unrewarding work because you didn’t save enough for retirement.
  • Supporting yourself on a fixed income and feeling your retirement world shrink a little bit more each year.
  • Having reoccurring nightmares about your old job and how they threw you out.
  • Having reoccurring nightmares about outliving your money, becoming a greeter at Walmart and moving into your kids’ basement.
  • Going through a debilitating illness and there is a cure for it but you can’t afford the medication.
  • Having plenty of money but you’re not physically able to get out of bed in the morning and do the things that you love.
  • Spending the next 30 years of your life without a reason to get out of bed in the morning, just killing time watching TV and waiting for the Grim Reaper to come.
  • Losing your independence as you’re forced to move into a nursing home.

Retirement hell is a place reserved for nonbelievers, retirees who didn’t feel the need to prepare properly for retirement when they had the chance. Because of that, they suffer by spending the rest of their lives paying for their sins.

Beware of the Black Swan

And it’s not just bad choices that could cause you to fall into retirement hell. You could get hit out of the blue by a Black Swan event (something unexpected) that has a major negative effect on your retirement. You can’t defend against Black Swan events, they just happen. But you could end up in retirement hell through no fault of your own.

Examples of Black Swan events;

  • You’re suddenly “packaged off” from your job late in your career.
  • Your spouse/partner dies unexpectedly soon after retiring.
  • You learn there is a problem with your company pension and they plan on cutting your benefits by 50%.
  • Doing all the right things health wise and still getting struck with terminal cancer.

The possibility of Black Swan events is why we urge people not to defer happiness like we used to do during our working years. It’s OK to plan for the future but you also need to enjoy every day and live in the joy of the present because you never know what could happen.


Many people go through hell when they retire, and they feel frustrated because they were told that retirement would be the best time of their lives and they can’t understand why it doesn’t feel like it.

But the good news is that it’s possible to escape from retirement hell and get to retirement heaven by following the nine retirement principles. Just remember the sooner you start the sooner you will get there!

This post was originally published on Victory Lap Retirement and reprinted with permission.

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Mike Drak

Author, Retirement Coach and Public Speaker at Victory Lap Retirement
Mike Drak is a thirty-eight year veteran of the financial services and lives with his wife Melina in Toronto, Canada. Mike is the Author of the best-selling book Victory Lap Retirement and also an award winning blogger, retirement coach and public speaker. Mike has also appeared on BNN, CBC Radio and iHeart radio.