How to Escape From Retirement Hell

Editor’s note: In his first book, “Victory Lap Retirement,” Mike Drak and his co-author Jonathan Chevreau wrote what Drak called “a retirement book about not retiring.” His new follow-up, “Retirement Heaven or Hell: Which Will You Choose,” (available on Amazon.com) offers advice on how to design a fulfilling retirement. In this excerpt, Drak describes what he calls “the three stages of retirement” and how to escape from the second one: Retirement Hell.

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Full-stop retirement may not be the fun, relaxing ride you thought it would be. This can be not only disappointing but downright anxiety-provoking, and it can give you that same sick feeling in your stomach that you get from riding a roller coaster.

In the beginning, the ride is pleasant, starting off on a slow, steady incline. The view looks quite nice and things are feeling pretty good — until you hit the sudden drop straight into Retirement Hell. From there, you experience many twists and turns that seem never ending. When you think the ride is about to end, suddenly you get hit by another curve. Thankfully, at some point things start to settle down and you start the long uphill climb out of Retirement Hell.

People who experience the scarier ride are the ones who, like me, were pushed out of their job or who enjoyed their work and identified too much with it and have a hard time letting go. When the choice of when to retire is taken away from us (that is, made for us), the ride through Retirement Hell will be scarier and longer. Take it from someone who knows.

Here are the three stages of retirement (represented in the chart below) and, most important, how to get out of the Retirement Hell stage:

In the Honeymoon Stage, when retirement begins, you can sleep in or golf as much as you like. People in this stage start knocking things off their to-do lists. It feels great to get things accomplished and be as free as a bird. This feeling of retire­ment bliss generally lasts up to a year before the new reality sinks in.

Once they have completed everything on their list, growth-oriented retirees often find that they need to find some­thing else to do, and this is when the trouble starts. Without a bigger plan or a purpose, they start to slide down to Retirement Hell, the lowest point in the Big Retirement Dip.

Although a life of leisure can be rejuvenating for a little while, even growth-oriented retirees can start to get antsy and begin looking for something more interesting or fall into a state of general malaise and emptiness without the source of satisfaction and accomplishment they used to get from their work.

Retirement Hell comes in many forms:

• After working long hours for so many years to take care of your family, now that you have the time, they don’t want to be near you.
• Getting divorced late in life.
• Living with someone 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 work that you hate doing because you need the money.
• Living on a fixed income and feeling that your world is shrinking each year.
• Having nightmares about your old job and how they threw you out, and not being able to move forward.
• Not being able to sleep at night because you’re worried that you might live too long and run out of retirement savings.
• Discovering that you have a debilitating illness and there is a cure for it, but you can’t afford to pay for it.
• Not being physically able to get out of bed in the morning and do the things you want to spend the money on.

Even if you enjoy a blissful honeymoon period of freedom imme­diately after you stop working, being unprepared for retirement often leads to Sudden Retirement Shock, a feeling of being in­credibly lost and vulnerable, which is Retirement Hell at its worst. Your heart isn't into hobbies and activities that used to bring you joy and you begin to wonder if that's all there is.

Suddenly, the life of leisure you dreamed about for so long and even enjoyed for a while becomes empty and meaningless. If you can't find a way to manage your retirement shock, de­pression will eventually set in, robbing you of your energy, vitality and self-esteem. You may have difficulties sleeping and eating, too.

It's hard to find help for Sudden Retirement Shock because most of the people in your life can't seem to understand what you are go­ing through. So, you give up trying to make them understand and instead look for ways to dull your pain: drinking too much, eating too much, shopping too much or becoming somewhat of a recluse are common es­capes. Living like this, though, for a prolonged period, will make the situation far worse and could be dangerous to your health.

This is something you want to nip in the bud before things get out of hand. It is best to talk to someone who understands and has already gone through what you are experienc­ing.

The pandemic scared us and opened our eyes to the reality of how empty and purposeless life can be when we don't (or can't) plan for it. We need to use that fear to motivate us to prepare properly for whatever route we choose to take.

To escape from Retirement Hell, all you need to do is be­come a Retirement Rebel and start doing the right things for you. Before you know it, you will be in that other, better place—the place you deserve to be.

Self-awareness is the way out of Retirement Hell.

So, how can you create momentum? By committing to start taking small steps that you can build upon each day.

Start to exercise and eat better, watch less TV and eliminate the things that keep nagging at you.

Make a list of the little things you need to do and start doing them. Completing and deleting them from your list will make you feel good.

Looking at what you managed to accomplish each day will boost your self-esteem and give you confidence that you're finally starting to make some progress at something.

This is how you get the ball rolling, but escaping from Retirement Hell requires more effort in the long run. You need to put some structure and routines back in your life, find suitable replacements for the work friends you lost, create a new identity for yourself and find new purpose.

Because in retirement you need to have a sense of purpose —  a good reason to get out of bed in the morning. Without that, you will almost certainly start to decline.

Be so­cial and make a lot of friends. Make it a priority to spend most of your time with people you care about and who care about you. When you find a new way to contribute or help others — to matter again —you will live longer and feel better.

Be an adventurer and live outside your comfort zone, exploring, learning, and doing interesting and exciting things.

By becoming a Retirement Rebel, you finally have a chance to unleash your passion and creativity — parts of yourself that you may have kept bottled up inside for years.

Retirement Heaven is where the smart retirees end up. Retirement Heaven is all about happiness and freedom. It's about living in the moment and not being stressed out over what tomorrow might bring.

It's where you connect with your inner child again, returning to that special place where anything is possible and there is always another adventure to go on.

Most important, it's about being intentional about what you do, how you spend your time and who you spend it with. No one is ever bored or lonely in Retirement Heaven, and that is a true blessing.

I'm not going to lie; it won't be easy. But take it from me, the payoff is well worth the effort.

Mike Drak 



Mike Drak is a 38-eight-year veteran of the financial services industry and lives in Toronto. He is a bestselling author (“Victory Lap Retirement”), award-winning blogger, public speaker and retirement lifestyle designer. His latest book, “Retirement Heaven or Hell,” shows people how to design and transition to their own version of a Victory Lap. Drak works with his wife, an investment adviser, helping her clients design their own fulfilling retirement lifestyles.   Read More