Today I’m continuing my thoughts on the retirement book, Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy
So far, here are the posts in this series:
- Win the Retirement Game, Introduction
- Win the Retirement Game, Fighting Boredom
- Win the Retirement Game: Take Control of Change and Move Beyond the Status Quo
- Win the Retirement Game: Connect Socially
- Win the Retirement Game: Be Creative
If you missed any of those you may want to go back and read them as they all build upon each other.
And we’ll be giving away a copy of the book at the end of this post. Be sure to check that out if you’re interested.
Exceeding Expectations
Today we’re talking about defeating expectations. This quote to start the chapter seems to sum things up fairly well:
Frustration always results from a discrepancy between your expectations and reality. David Burns
Haha. True. That’s why having low expectations is a super power. lol.
Because when you expect too much, you get results like these:
In a 2021 survey, over 75% of retirees with an average time in retirement of 8 years said their retirement life falls short of their expectations.
I don’t know what these people expected or what their retirements have been like, but my retirement has been AWESOME and well above expectations.
My guess is they either had totally unrealistic expectations or some misfortune came upon them in retirement (many problems are self-made — by failing to plan for the time side of life.) A quick Google search found that 46% of current retirees report struggling to pay for their monthly expenses, so there’s that too.
So what’s the answer? Lower your expectations! Hahahaha.
No, seriously:
It sounds like you’re saying I should lower my standards. I don’t like that. I want to keep the bar high. My philosophy is if I fall short, I’m still likely to be way ahead.
In your business career, that may have been helpful to you. But there’s a price to pay if you’re setting expectations too high. It’s stressful. Now that you’ve taken early retirement, it’s wise to set the bar lower for yourself, at least in some areas of your life.
When we think about the overall direction of our lives, our expectations may be unrealistic, and they can leave us unprepared for the challenges that inevitably arise. Bruce Feiler, author of Life is in the Transitions: Mastering Change at any Age, interviewed 225 people from all walks of life about their life stories. His analysis of their experiences revealed that people tend to expect life to unfold in a predictable, linear fashion with common milestones at different ages. Yet Feiler found the life stories he heard were consistently non-linear. The average person in his Life Story Project encountered a disruptive event every 12 to 18 months. He also discovered that people face a significant transition point, which he dubbed a “Lifequake”, between three to five times in their lives. Feiler’s data also indicates it takes some time to work through a transition. It’s not usually a quick pivot — quite the opposite.
My thoughts:
- I prefer a balanced strategy when it comes to retirement. Let’s not expect too much but let’s also not expect it to be a disaster. I think for someone who plans well in advance, expecting a “good” retirement is acceptable. Not great, not unbelievable, but good. And you can probably beat that too IMO.
- I suggest people plan in advance for the life they want in retirement. This includes what they will do, how their time will be allocated, and so on. They then can test these things out while employed — tossing the items they find they don’t like and keeping the things they do. Then, based on these, they can go into retirement with fairly realistic expectations of what it will be like (which I think should be “good” on average).
- And when life throws them a curve ball, they need to be open to change and be creative in what can be challenging situations (we’ve talked about both of these previously in this series.)
- I think the problem comes when people expect retirement to be a 30-year vacation…with the same feelings they had taking that one week vacation in their working years. That’s a completely unrealistic expectation…no one can be on vacation that long (at least at that level.) So if they expect that, they are almost guaranteed to fail.
- People also fail when they don’t plan for retirement…and at that point even low expectations can be missed. It’s amazing to me that people spend about as much time planning their life/time in retirement as they do deciding what’s for dinner tonight. It’s crazy!
Society Has Expectations
The book goes on:
Societal expectations of retirement sway us. People have views on what retired people should do and what they should not do. There’s a set of norms and milestones we’ve internalized about retirement. Although those norms are becoming outdated, they persist. When someone has a different vision and timetable for their retirement, they can get a lot of push back from other people. Many preconceived notions about retirement are negative and ageist. Research indicates such stereotypes about retirement can carry weight. They can affect how we think about retirement; they can also influence health outcomes and longevity.
I try to keep this site PG rated, so I can’t tell you what I really think of “societal expectations.” Hahaha.
In fact, I like going against the flow.
I remember in those early days of retirement (before Covid when it seemed no one worked from home). I would be out and about and people would ask me why I wasn’t at work (in one way or another). Then I’d say, “I’m retired” and step back to watch the show. I could see their struggle with what I said versus what they saw (I look young for my age too — so that made it worse) and I could feel their heads about to explode. Hahahaha. That’s what society gets for its expectations!
If you worry about what “society” thinks, then early retirement is probably not for you. And retirement later in life isn’t looking great either. lol
That said, I think the toughest expectations are often our own…or the expectations of those closest to us. Everyone else is noise. I know I have always held myself to a pretty high standard — one that’s usually way below what society expects of me (like I care anyway).
And speaking of those closest to us…
Family members and coworkers have views about your retirement plans. How optimistic or pessimistic they are about their own retirement can color their opinions about your retirement plans. The opinions of others can shape your thinking and have a significant effect when people do not pre-plan how they’ll invest their time in retirement. It’s good to get input from others, but without developing a clear vision of your retirement, others can have undue influence. They may not be in your best interest, even when others are well intentioned.
Coworkers? Again, who cares what they think or what their expectations are?
Odds are 90%+ of them are terrible at handling money, have no idea how to retire themselves, etc., so what do they know about the situation, your plans, etc.? They are probably pessimistic about their own retirements — don’t let them throw that doom and gloom monkey on your back!
Family members? The only ones that matter IMO are your immediate family. They are the ones most impacted by a retirement. The extended family may have opinions, but I’d give them the same level of attention I’d give “society’s” expectations. Which is very little.
My immediate family members were happy that I retired when I did. A few that were more removed were surprised, but everyone was supportive. Good thing they were or I’d have to throw them off the train. Haha.
The book continues:
Expectations, as an opponent, don’t go it alone. It enlists our neighbors, friends, and coworkers to tempt us to play keep up with the Joneses. As human beings, we’re very conscious of our social standing. It’s a fundamental motivation. It boosts our self-esteem. Research has shown many people care more about status than they do about money. We’re continually engaged in social comparison of how we’re doing relative to others.
Retiring involuntarily can shake up your sense of status. When something threatens our social status, it creates anxiety. It stirs up negative emotions. One study demonstrated that people who compared themselves frequently to others experience more guilt, regret, and blame than participants who engaged in less social comparison. Such comparisons can even harm our physical health as they have a significant influence on how we perceive our well-being.
Trying to keep up with the Joneses is a fool’s errand. People often find out that the Joneses are overextended financially to keep up appearances. However, that doesn’t stop us from thinking we should be living the same lives they are.
This is another way expectations deceive us — by creating a false sense of obligation. Psychologist Albert Ellis, who created Rational Emotive Therapy, colorfully encouraged people to stop “shouldering” on themselves. In his view, telling yourself that you should be doing something — or not doing something — leads to irrational expectations. For example, having expectations about where we should be at various milestones in life can lead to behaviors driven by fear or anxiety more than by rational choice.
Lots of thoughts on this nonsense:
- If you are anywhere close to the financial independence community you probably left the Joneses and what they think far in the rearview mirror. Who cares what they think? They are broke, miserable, and the farthest thing from an example you’d ever want to follow.
- To me, retiring early is about the biggest social flex you can pull. I know several people who are older than I am, much wealthier than I am, and are still working. Now maybe they are working because they want to. But I know some aren’t for sure — they need the money because they spend too much. So when they tell me about how huge their business/portfolio/real estate is, all I can think of it, “Yeah, but you’re not free. You’re still in the rat race.” Why would I think they have more/better social standing than I do? Haha. I’m thinking they are suckers. lol
- “Research has shown many people care more about status than they do about money.” See? I told you they were suckers. I’m more in favor of stealth wealth.
- “We’re continually engaged in social comparison of how we’re doing relative to others.” This is true, and it can be good and bad. It’s good if you pick the right people to emulate and don’t go overboard. If Joe saves 20% of his salary and I want to be like Joe, that’s a good thing IMO. But it can get out of control too, so you need to limit the comparison. For example: “Why does Joe have $15 million and I ‘only’ have $7 million?”
- “Retiring involuntarily can shake up your sense of status.” I will give them this. Key word: involuntarily. If you are laid off or fired, it can be a shock to the system, there’s no doubt about that. But retiring voluntarily is a whole different deal — it’s VERY positive IMO.
- Yes, comparisons can be bad for you…if they make you feel terrible. This is why it’s best to limit them as much as possible. Concentrate on your life and don’t get distracted by what others are doing.
- “Telling yourself that you should be doing something — or not doing something — leads to irrational expectations.” When I tell myself I should be doing something (or should quit something) it usually results in action that’s beneficial to me.
Who are these people who place so much of their lives and self-worth on what others think? It just seems crazy to me.
The book goes on a bit about this topic, but the main point has been made, so I’ll skip that.
In fact, I’m just going to go to the takeaways from this chapter.
Takeaways
A couple of the takeaways from the book:
Expectations can carry more weight than they should if they’re unexamined. Reflect on your expectations for retirement. What are they based on? How are they shaped by cultural notions of retirement that may no longer be relevant? Examine and challenge your assumptions. Identify unreasonable expectations that you want to let go of.
Keeping up with the Joneses is a distraction. Is it time to let that go?
Yes, for heaven’s sake, please stop worrying about the Joneses and what they are doing.
And while you’re at it, stop worrying about what your coworkers, extended family, friends, and society in general thinks about you and your retirement plans. Simply plan for and create the life YOU want to live and let the others do their own thing. Move on with your life and don’t give their opinions a second thought.
Yes, you can seek feedback (like we offer in the Millionaire Money Mentors forums) and get thoughts on how to do this or that, but get that without the judgement that expectations heap on you.
That’s it for today! Stay tuned for our next post coming up soon.
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As I said above, I’m giving away a copy of Win the Retirement Game on every post I do about the book. Here’s how to you can enter:
- Leave a comment below telling me what you liked best about this post, what you think you can use, or something you learned from it. Basically just share anything meaningful related to the content above (note: “please enter me to win” and similar comments will not be considered out of pure weakness! At least put a bit of effort into it!) This should be fun!
- Be sure to leave your email address when you leave the comment so I will know how to reach you if you win (the email address will not be visible to anyone other than me).
- The winners will be selected by me at random a few days after this post goes live. I’ll announce who wins in my own comment.
- I’ll email the winner, get their address, and send them a book from Amazon.
As with most giveaways, there are rules. Here they are.
Good luck!!!!

Great article. I always remember that life is what happens to you while you are waiting for something else. I’ve also been blessed with the ability to recognize opportunity, even if she isn’t dressed as expected. Lowering your expectations will result in more opportunities.
Your most important asset is health, the second is time and the third is resources. Plan for those accordingly and you can’t help but enjoy life.
I’m also a great believer in making your own luck. As a result, I have been very lucky indeed.
In my life, two bad examples (my parents) were much more instructive than good ones. I learned a lot, developed a plan and an outlook, and expect to live a wonderful 31 more years.
I appreciated the Bruce Feiler information on disruptions in life. It makes it easier to deal with them knowing they are so common.
I am really enjoying your series on Retirement. Having retired a few years ago, I still struggle with the expectations part. Your comment on “feeling like you are on vacation” was my expectation and yet, three years into my retirement, I have not taken one……(I did go to the MMM last year and a brief long weekend in Chicago in December, but that is it). My goal this year is to finally book a real vacation and enjoy a break from the day-to-day activities that currently keep me busy. I have responsibility for my 91-year-old mother, my son, and two dogs…..so that is the excuse that I tell myself however, I know there are options for them when I am on a trip. I just need to do it!
Your posts encourage me to stay focused on how to have the best life for me in retirement, so thank you!