Top 5 Reasons Why Your Dream Retirement May Be Sinking FAST

March 15, 2022

Even Pros and Science Teachers can fail the big Test

Just ask former Professor Nancy Schlossberg a well-known researcher of retirement and transition issues. Professor Schlosberg first retired from a long academic career in 1998 and moved like many of her generation to sunny Florida.

The transition from professor to retiree did not go as planned. Instead of feeling elated, she felt lost. Instead of taking it easy, she kept searching for something meaningful to do. After some soul searching she discovered that she missed her identity as a college professor. She had trouble adjusting to being “fully” retired. She choose to “un-retire” to write a book.

As anybody that’s tried it, writing a book can be as demanding as or even more so than your typical day job. Professor Schlossberg was an expert on retirement before she retired yet she still found the transition difficult. Since her "first" retirement she has written not one but eight books - the last one (she swears) was published in 2017. 

Here's another story. 

I recently took an Uber ride on a cold winter night in Boston and, as I usually do, started a conversation with the driver. It turns out that the driver (I’ll call him Mike) started driving for Uber three years ago.

He appeared to be in his late 60’s so I asked him what he did before driving for Uber to which he chuckled and said NOT THIS." 

"This was all my granddaughter’s idea.”

It turns out that Mike retired after a 30 year career as a high school science teacher. After sitting back and relaxing for the first few years, he grew bored and anxious.

“Playing golf and watching reruns of the Walton’s can only take you so far.” 

Mike tried to go back to his old job but they had moved on. He tried tutoring high school students but found the work unfulfilling. He didn’t miss the work, but rather the people. He missed being a part of things!

Then one day, his granddaughter said that he should be an Uber driver. “I had no idea what that was, but my granddaughter showed me how it works.” He thought about it. He liked getting out of the house. He could use a few bucks and best of all he could pick his schedule. If he didn’t like it, no big deal.

For Mike it’s been three years as an Uber driver and he loves it. Of course, not always the driving part but engaging with people oftentimes his granddaughter’s age.

“I learn so much from just hearing them talk and more often than not we end up having our own conversations. It has made my retirement so much more enjoyable. Rather than talking about the good old days like most of my former colleagues, I get to feel part of the real world.”

Benjamin Franklin


"I didn't fail the test. I just found 100 ways to do it wrong"

Retirement - easy if you're a robot, challenging if you're a real person

Most people think that retirement is a breeze. It’s the time in life when you no longer have any family and career commitments that suck up all your time and energy. It’s all beautiful sunsets and relaxing walks on the beach. No need to worry about anything anymore.

Sounds great, if only it were true.

In reality, many retirees find themselves at a loss. After so looking forward to their “golden” years they find themselves bored, disappointed and often anxious about the future.

How’s it possible to fail at retirement? 

With all the free time?

Without the stress of yet another soul-sucking “corporate” restructuring?

What's wrong here?

Surely, these Baby Boomers must a bunch of malcontents. They have it so much better than grandma and grandpa! They have raided the young with their generous social security and Medicare programs and they are still bummed out? 

All true and that makes it feel even worse. It sucks!

When you’re supposed to having the time of your life and you’re not you feel even worse. Like something is wrong with you. Like you’re the only one at the dance without a partner. You feel guilty. You feel like you’re wasting the rest of your life.

Awful isn’t it? "Poor bastards" you may think.

Let me tell you a little secret,

We ALL have these depressing thoughts!

Even pros like Nancy Schlossberg or my Uber driver, Mike. I have had these thoughts and I am not quite retired yet.

Tell me the truth,

Are you the only person on the planet that has not had these feelings?

Nobody told you about the rough side of retirement, did they?

You’ve been going through transitions your whole life. The one into retirement is supposed to be easy.

You have been dreaming about retiring for years. You anticipated smooth sailing ahead, but suddenly the seas have turned choppy and the headwinds have picked up. Nothing you can’t deal with but still stressful. Not exactly the ride you expected especially at this stage in life.

Nobody told you about these “challenges”.

Nobody. Even your best friend that retired a while back kept his pie-hole shut. It’s as if in order to be indoctrinated into the “retirement club” you need to go through the stress and annoyance of hazing all by yourself.

Why couldn’t somebody have warned you before? You would have prepared better and sailed right thorough the storm into retirement bliss.

I get it. I often wish that things were different. Easier for sure, but it never seems to work this way. You’re always that lone wolf lost in the woods having to find your way out without any help.

You may still be that lone wolf lost in the woods but I am going to tell you about a couple pitfalls to look out for.

Unfortunately I can’t hold you by the hand and promise that everything will be all right, but at least you’ll be forewarned.

Here we go.

Look out for the 5 WARNING SIGNS THAT COULD sink your Dream Retirement


Playing footloose with your finances

  • Overspending especially in the early years of retirement
  • Not  getting a decent return on your money
  • Ignoring the compound loss of purchasing power caused by inflation

The surest way to mess up your journey is to run out of fuel. Money is necessary as the fuel that propels your life in retirement. Without it you will live in survival mode and who wants that?

You might live 2 or 3 decades in retirement. You need your money to last and, therefore, you need to manage your financial resources.

There are two key ingredients to your financial health.

One is balancing your expenses and sources of  income.  You can't just spend willy-nilly and expect not to drain your savings.

The other is to keep your financial assets working for you by investing in strategies designed to beat inflation.    

Try this,

  • Have a realistic budget (that you stick to) and allocate some leftover money to unforeseen contingencies
  • Don't become overly risk averse with with your financial assets - you still need to get a return and that means taking some investment risk
  • Distinguish between "needs" and "wants" - evaluate how much your "wants" are costing you. Your "needs" are your priority


Watching the same re-runs over and over

  • Sticking to an outdated identity
  • Complaining about how the world has changed (in a bad way)
  • Sticking only to what you’ve done in the past

We all enjoy watching re-runs occasionally but after a while most of us crave something new.

People that spend all their time thinking about the past not only get stuck in their own heads but little by little start annoying even their closest friends and family.

Do you have friends that keep talking about their "glory" days? Like your friend that "casually" keeps mentioning what a big shot they were at work? Annoying, right?

Our roles in life change over time.  Our circumstances change. The world changes.

Rather than living in the past, the goal should be to move forward and grow into the best version of ourselves for the stage in life we're in. 

Something to Think About,

  • Be grateful for your past, live in the present, and look forward to the future
  •  Adopt an identity consistent with your current stage in life
  • Re-imagine your life by consciously designing your Future Self

Bill belichick

-nfl coach

"To live in the past is to die in the present"


Seeing the bogeyman everywhere

  • Focusing on things you have no control over (the weather, the stock market, crooked politicians, millennials (not your children, of course) 
  • Only doing “safe” things that you have done ad nauseum in the past
  • Ignoring the drain that negative emotions exert over you

Retirement brings out many fears in people. We can let fear of the unknown drive our behavior but at the cost of our world becoming smaller and smaller.

If we let fear win, our whole lives will be spent playing defense. We'll avoid doing anything we haven't done before.

We'll chop off the upside of life to prevent "bad" things happening to us. The truth is, many of those "bad" things may or may not happen. Are you that afraid of the unknown to limit good things from happening to you? 

Try this,

  • Put some space between your thoughts, emotions and actions. Don't allow your unchecked negative emotions dominate your behavior
  • Inch out of your comfort zone. Taking action is the best recipe for dealing with your fears even if all you take are tiny steps
  • Change your environment (if it reminds you of your concerns and worries) to reinforce the type of person you want to become. Yes, you can become the Fearless Leader of your Life!

patty digh


"The death rate for people who play it safe and for people who live boldly is the same: 100%"


Loving "Manana" a lot more than today

  • Avoiding having any structure to your day
  • Being “busy” versus being "productive"
  • Always thinking that "manana" is the best time

Are you always busy? Are you always putting stuff off? Never seem able to find the time to go for your dreams?

If you are, it could it be that you don't value your time enough. It could be that your priorities are off. You say one thing but act as if you will live forever.

Time can be your friend or enemy. You choose by your actions. We all get the same 24 hours a day. As author Sam Horn likes to say, "tomorrow is not a day of the week."

Make each hour count in the way that matters to you. For some people that is spending quality time with a friend or relative. For others it is about learning a new skill that will help them down the road.

You decide what is important to you and make the time for it. Simple!

Try this, 

  • Evaluate what you’re doing that’s keeping you so busy. Is it important, or just a bad habit? Bonus Question: How many hours a day do you spend in front of your TV or computer?
  •  Allocate time to the things that matter to you - your relationships, your vocation, your hobbies, your health, for instance. These are the things that five years from now you will be grateful you invested in  
  • Track how you spend your time for a couple of weeks. Then decide if your time allocation is consistent with  the life you want to lead. What are you over-investing in? What important area of your life is being neglected? 

steven covey

-motivational coach 

"Most of us spend too much time on what is urgent and not enough time on what is important"


Not accepting new members into the Friends & Family Club

  • Not replacing lost friendships with new ones
  • Relying only on your spouse and immediate family for support and interaction
  • Only interact with people your own age and social status

Who's on your team? Does your team keep you going when you're feeling blue? Are you, in turn, a key player on somebody else's team?

We all need to have a good team around us. People we can trust and especially people we love and appreciate for who they are. The type of people that support you in whichever way you need at the moment. It might be a pep talk. It might be tough love. It might be as a sounding board. 

People come and go throughout our lives. As palliative nurse Bronnie Ware states in her book, The Top Five Regrets of the Dying,  not staying in touch with close friends is a big regret for people. Sad but true. 

How many good friends have we had throughout our lives that we no longer stay in touch with?   I know I have several and unfortunately some are gone already.

It's inevitable that we will lose some friends over time. We will also lose family members that we love. Nothing is static but that is more reason to stay engaged with the world and keep our social circles fresh and vibrant.

Like a good gardener we must nourish and nurture our friends and family.

Something to Think About

  • Participate in fun activities that involve group interaction with people outside of your current social circle 
  • Adopt an attitude of being of value to others - you never know when you'll need help
  • Mentor a young person, work outside the home, help a neighbor, volunteer, engage in the world in any way you can


-ancient african proverb

"If you want to go fast, go alone. If you want to go the distance take a team"

Plug your Holes before they sink you Dreams

It's never easy right? Everybody told you that retirement would be a piece of cake but now you know. Even pro's like Nancy Schlossberg  and retired science teachers can fail at retirement.

Failure is not necessarily bad if you learn from the experience. Everybody looks at retirement as a one and done thing when in reality it is about the rest of your life.

You could spend 2 or 3 decades retired.

Don't you think that a lot will happen during this time? 

The expectation that we need to figure it all out before we retire and then stick religiously to the game plan leads to nothing but frustration. Not only does the world change but so do your circumstances. More importantly, you will change as you transition through this next phase in life. 

And as we all know, transitions are never easy.

Retirement is an end to your primary career days but not an end to your life as you know it. Some of your nagging life challenges will stay with you forever as will some of your key personality traits and values.

All retirement does is free you from the job you once had. It gives you to freedom of a new beginning but getting through the "messy middle" as MEA founder Chip Conley would say is not a gimme.

Why should we expect only smooth sailing in retirement?

Instead of expecting perfection a better approach might be to, as noted coach Zig Zigler once said,

 "Expect the best. Prepare for the worst. Capitalize on what comes."

The key prerequisite of a successful retirement is taking action. It involves plugging those pesky holes that we all encounter before they sink our dream retirement.

Take that first step! You'll be thankful you did five years from now.

Imagine what a retirement full of possibilities would look like! 

Join our Community to get started

About the author

Eric Weigel

My goal is sharing my experience as an investment manager, certified retirement coach, and fellow Baby Boomer to enable people to design the life they want and that matters to them in their next phase in life. We all want to live longer, but we also want to lead a life of meaning, joy, and fulfillment.