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5 Reasons Your Retirement is Going to Suck

Updated: Apr 26, 2019

by Gary Stamper

Let’s not fool ourselves: while having money will not be a negative once you are retired, there are a lot of people out there that have 401k’s, pension and retirement plans, and money in the bank who are still going to be miserable after they retire.


“It Takes courage to grow up and become who you really are.” ~ E.E. Cummings


This is not an article that’s going to chew you out for being poor or broke when you retire, although that really does suck. Let’s not fool ourselves: while having money will not be a negative once you are retired, there are a lot of people out there that have 401k’s, pension and retirement plans, and money in the bank who are still going to be miserable after they retire.


I’ve never been rich, but it seems that no matter how much money people might have, there’s never enough. So let’s take money out of the equation, because, let’s face it, you either have it or you don’t and this isn’t an article to try and fix that as you approach retirement or if you’re already retired.



the 5 Reasons


1. You don’t really know yourself. You’ve spent 20 to 30 years doing jobs for someone else. You traded hours for dollars, maybe by choice, maybe because that’s all you could do or find. Maybe your purpose was your marriage, your children, keeping them safe and providing for them, but it wasn’t your job. Your job may have been a means to an end, with your family the end, your purpose. Now your kids are grown and taking care of themselves and their own families… Seriously, how’s your marriage? Who are you? What do you believe in? What fills you with joy and wonder? If you can’t answer these questions, it’s past time to find those answers. 2. You’re looking back, not ahead. You loved your job. You loved the sense of fulfillment it brought you, the money was good. You were great at it! You loved the people you worked with. They were your friends… and one by one they left or retired, and they were replaced by younger people you didn’t understand and who didn’t understand you and didn’t care. It’s all changed, it’s different, and so are you. The business has changed… and so have you. Maybe it closed its doors, or maybe you got to retirement unscathed, or maybe you were let go or furloughed before you could collect your full pension. You may be angry, bitter. Is that who you want to be? Is this what defines you? How can you fill this huge void in your life that gnaws at you everyday? No one’s going to answer these questions for you.

3. You’re just F***ing bored. You went from 100 mph one day to 0 mph the next. It‘s called retirement. Yes, you had hobbies… two! The train setup in the basement and golf. Two weeks later you were bored to tears in the basement with what used to be a fun hobby, but now the kids are gone and it just feels lonely and unsatisfying… boring! The guys you were golfing with are now playing with new partners who are not retired and with whom they can do business with, and what used to be a fun second “hobby” has turned into something the wife just wants you to do out of the house because you’re driving her nuts, too! You know you need to make changes, but you just don’t know where to begin.

4. Could You Be Any More Lonely? You’re retired and single… maybe you’ve recently divorced, or worse, maybe you’ve recently lost a life partner, your mate, the person you were planning on spending the remainder of your life with, and now that’s gone., and so are they. A senior dating site? Get real. I need two years to grieve through this and then I’ll be two years older than I am now. I’m on anxiety medication and have started what is likely to be a very long relationship with psychotherapy. Not what I had in mind. I have to admit to myself I honestly don’t know myself very well at all. 5. You Will Have Health Issues. Let’s face it: At some point, we’re all going to have health issues, ranging from annoying to life-threatening, and even if you just slow down, one day you’re going to stop. I hate to break it to you, but our eventual deaths are inevitable. For now, you need to factor in your current health, as well as any foreseeable serious issues you are likely to encounter in the future. Many health issues cannot be predicted, but based on your current health, you may be able to make educated guesses about your health in the future. This will affect your lifestyle and where you want to live, in addition to your wallet. This is also part of knowing yourself.


Many of us get along pretty good in life as long as things are running fairly smoothly. We may even consider ourselves “happy” even though we may not have the “perfect life” that others seem to have. However, when things go wrong or get difficult, watch out. But when we focus on meaning and purpose that’s larger than ourselves, we no longer need to pursue happiness. It comes naturally, even in the face of temporary setbacks and discomforts.


As a Life Coach Retirement Strategist, it’s not my job to give advice or provide solutions, but, rather, lead you to your own realization of what you probably already know what you should be doing, however deeply buried it may lie within you, because who knows you better than you? As my client, I believe you already have the answers. My job is to help you uncover those answers, but you have to first ask for help.


You are where you are, but you can get to where you want to go.


____________________________________________________________________________________ Gary Stamper is a Certified Professional Coach and the founder and creator of Old Dogs New Tricks, a website that supports men in being compassionate badasses after they retire. He is also the author of Awakening The New Masculine: The Path of the Integral Warrior, a book about evolutionary consciolusness and men's spirituality.

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