Why So Many People Are Unhappy In & Hating Retirement

exhausted senior woman sitting on the bed with a laptop

If you’re reading this, chances are, you’ve hung up your work boots to step into the golden age of retirement. 

 

It’s supposed to be a time of relaxation, freedom, and joy, right? 

 

Well, sort of. 

 

For a lot of people, the new territory brings a bit of unhappiness. 

 

Or even misery… where you find yourself thinking, “I hate retirement.”

 

Because of the stereotypical way retirement is depicted, many people anticipate retirement as a time of leisure and happiness – only to find themselves grappling with unexpected emotions and challenges. 

 

But here’s the good news: it’s not an uncommon feeling, and more importantly, it’s not a life sentence. 

 

In this blog post, we take a dive deep into why so many people feel unhappy in retirement, share some relatable stories, and (hopefully) inspire you with ways to turn this feeling around. 

 

Understanding the Problem: “I Hate Retirement”

Imagine this: You’ve spent decades waking up to the buzz of an alarm, being in the thick of things, and constantly juggling a flurry of tasks.

 

And then one day, it all stops. 

 

The alarm doesn’t buzz. There are no emails to check, meetings to attend, or urgent tasks demanding your attention. 

 

But, even with all the stress and responsibility out of the picture – you find yourself saying, “I hate retirement.”

 

Now, let’s get one thing clear right off the bat. 

 

It’s perfectly okay to feel this way. You’re not alone. And more importantly, there’s nothing wrong with you. 

 

Retirement is a seismic shift in your life, and it’s natural to find it disorienting and difficult at first.

 

It isn’t just one phase of life; it’s a journey with several emotional stages, each with its own challenges and rewards. 

 

And it’s very likely you’re in the disenchantment stage where the honeymoon period is over and feelings of restlessness and dissatisfaction start to creep in.

 

the 5 emotional stages of retirement are: pre-retirement phase, honeymoon phase, disenchantment phase, reorientation phase, and the stability phase

 

But why does this happen?

 

Why So Many People Are Unhappy in Retirement

Retirement, a phase of life that many look forward to, can sometimes turn out to be a source of unhappiness. The reasons for this are manifold and often interconnected. 

 

Let’s delve into some of the key factors contributing to unhappiness in retirement.

 

why so many people are unhappy in retirement: lack of purpose, insufficient socialization, mandatory or unplanned retirement, health problems, financial insecurity

 

#1 Lack of Purpose

The topic of “purpose” in retirement, sadly, goes highly unaddressed in traditional retirement planning — where financial planning remains the main focal point of retirement preparedness

 

Here’s the widely unspoken truth:

 

For many, work provides a sense of purpose and identity. When that’s taken away, it can lead to feelings of emptiness and loss of self-worth. It’s like being uprooted from familiar ground and transplanted into new, unknown territory. 

 

We get it, it’s a tough transition to make. And if this resonates with you, you’re definitely not alone, as 31% of retirees admittedly struggle with a lack of purpose. You’ve gone from having your days filled with tasks and responsibilities, to having an open schedule that needs filling. 

 

This can lead to feelings of uselessness, immense fatigue, and even to the so-called “retirement syndrome“.

 

And friends, family, and even the internet, all advise you to keep busy. “Take up golf,” they say, or “Why not volunteer?” But somehow, these activities feel hollow, like you’re just aimlessly trying to fill time.

 

The truth is, retirement isn’t about keeping busy for the sake of it. It’s about digging deep to discover what truly matters to you, now that you’re free from the constraints of a 9-to-5 job.

 

(P.S. Here’s a quick 10-question quiz to help you discover your retirement purpose).

 

#2 Insufficient Socialization

For decades, your workplace has likely been more than just a place to earn a living. It’s been a bustling hub of interaction, a hotbed of ideas, a place where you’ve forged friendships, shared laughs, and even weathered storms together. 

 

Workplaces are often the backbone of your social network, providing daily human contact and camaraderie. 

 

Just think about it, the average worker spends eight hours every day with their colleagues. This is essentially a third of your day. So it comes as no surprise that 76% of people make friends through work, trumped only by high school.

 

how do americans make friends

 

And then comes retirement, and suddenly, this part of your social network almost evaporates overnight. No more water cooler chit-chat, no more team lunches, no more friendly faces to greet each morning. 

 

This abrupt change can leave a void, leading to feelings of isolation and loneliness.

 

#3 Mandatory or Unplanned Retirement

Life has a knack for throwing surprises our way, and sometimes, these surprises come in the form of unexpected retirement. As many as 56% of Americans over 50 have faced this challenge in 2018.

over half of american workers over 50 are forced out of jobs

 

One day you’re part of the workforce, and the next, you’re being ushered into a new phase of life that you didn’t see coming. It can feel like an abrupt shift, causing a swirl of emotions simply because it happened unplanned.

 

After all, work is more than just a paycheck. From the sheer amount of time spent working, it can easily become a part of who you are — especially when you consider one-third of your life is spent at work.

 

Those 90,000 hours over a lifetime can easily shape your daily routine, influence your social interactions, and contribute to your sense of purpose. If this significant aspect of your life is suddenly removed, it’s only natural to feel a bit lost and totally unprepared.

 

#4 Health Problems

Retirement, the much-anticipated phase of life, can sometimes be overshadowed by health issues. Health concerns can sneak in, casting a shadow over this otherwise vibrant period.

 

Health issues come in many forms. There’s the stiffness that creeps into joints, making morning stretches a little more challenging. The breathlessness that might accompany a walk in the park. The constant monitoring of blood sugar levels or blood pressure. 

 

These health concertns, once distant thoughts, now become everyday realities.

 

By 2030, researchers estimate that more than 60% of Baby Boomers will be managing more than one chronic condition. Yep, you heard it right — you’re not alone in this boat.

 

Without improving your health concerns, it can undoubtedly dampen the spirit of retirement. It can feel like being handed a tough assignment just when you thought you were done with work. 

 

#5 Financial Insecurity

The transition to a fixed or reduced income can feel like a tightrope walk, with fears of the unknown lurking below.

 

According to recent research, financial insecurity is a pressing concern for many retirees. A staggering 80% of households with older adults are financially struggling today or are at risk of falling into economic hardship. 

 

The fear of not having enough money to cover living expenses, unexpected health care costs, or recreational activities can cast a long shadow over retirement, leading to constant worry and stress.

 

But this is your story, and you’re still the author. You have the power to rewrite this chapter. You can turn your retirement from a time of loss and confusion into a period of exploration, growth, and joy. 

 

It’s not going to happen overnight, and it will require some effort on your part, but trust us, it’s entirely doable. Here’s how…

 

From Unhappy to Happy Retirement in 6 Steps

a happy retirement in 6 steps: recognize your feelings, discover what truly matters, find clarity, set clear goals and commit, tailor your routine, embrace change & cultivate growth

#1 Recognize Your Feelings

Retirement can be a rollercoaster of emotions, and that’s completely normal. There are so many changes happening, and it’s okay if you’re not feeling great every day. Maybe one day you’re thrilled to be done with work, and the next, you’re aimlessly anxious about your future. 

 

But the important thing is to recognize these feelings and allow yourself to feel them. 

 

Acknowledging the different emotions you’re experiencing can help you understand what you want and need from your retirement. Plus, a 2018 study found that simply labeling your feelings decreases the duration and intensity of uncomfortable emotions.

 

So take a deep breath, put words to your emotions, and remind yourself that it’s okay not to have it all figured out right away. 

 

#2 Discover What Truly Matters

Sometimes, figuring out what brings you joy means we first need to understand what’s stealing your sunshine. It could be a rocky relationship, a lack of purpose, or even those nagging self-doubts. 

 

Whatever it is, identifying these happiness thieves is your first step towards a retirement brimming with joy.

 

First up, jot down all the things that put a spring in your step. Maybe it’s spending time with your grandkids, savoring your morning routine with a hot cup of tea, or getting lost in a world of paint and canvas. There’s no right or wrong here; these are your happy moments.

 

Next, list out the things that rain on your parade. It could be a lack of motivation, neglecting self-care, self-doubts whispering you can’t do this, or socially isolating yourself. 

 

Now here’s the magic part. Look at your two lists and ask yourself, “How can I do more of what brings me joy and less of what makes me unhappy?” 

 

Maybe you can swap an hour of watching the news with a walk to the park. Or how about calling an old friend when you’re feeling lonely instead of scrolling social media?

 

This might seem overwhelming at first – change often is. But every great journey begins with a single micro-step. And you have already taken that step by identifying what brings you joy and what doesn’t.

 

#3 Find Clarity

Retirement marks a new chapter in your life, but it can be disorienting. Suddenly, you may feel lost without the job or family responsibilities that once defined you. 

 

That’s where finding clarity on your retirement purpose comes into the picture. You need to dive deep down and rekindle the dreams that were buried under the to-do lists and deadlines.

 

The process of finding clarity won’t happen overnight. It requires honest attention, introspection, and a dash of courage. But it’s definitely worth it.

 

That’s why we’ve put together a special resource for you — our “Finding Clarity Workbook.” It’s designed to help you with some solid first steps in navigating this journey to clarity, with exercises that prompt reflection, inspire dreams, and encourage action.

 

finding clarity workbook cover

 

#4 Set Clear Goals & Commit

Setting goals isn’t just for the workplace. It’s a powerful tool that gives your life direction and purpose, no matter what stage you’re at. In fact, only 6% of older adults have no goals whatsoever.

 

Once you have clarity, it’ll be easier to think about what you want from your retirement. 

 

Maybe it’s finally having the time to write that novel that’s been brewing in your mind all these years. Or perhaps it’s getting fit enough to run a marathon. Heck, it could even be perfecting your grandmother’s secret apple pie recipe. 

 

Either way, the clarity has to come before setting your goals – otherwise, you’ll lose steam, time, and energy on things that aren’t a good fit to begin with.

 

The point is that your goals should be something that sparks joy and excitement in your heart – and not the stereotypical “retirement activities” that others suggest. In other words, don’t do something because it’s popular for your age group. 

 

Dig deep to find clarity first – so you can chase something that makes you jump out of bed every morning, eager to start the day.

 

Once you’ve identified your goals, commit to them. But this isn’t the corporate rat race anymore. You’re not chasing deadlines or competing against colleagues. 

 

This is your time and your growth journey, so commit to your goals with love, passion, and patience. And most importantly – consistency and structure – which brings us to our next tip.

 

#5 Tailor Your Routine

No more alarm clocks blaring at the crack of dawn. No more rushing to beat traffic. It’s like having an endless summer vacation, isn’t it? Well, yes… and no. 

 

While you certainly have more freedom now, having absolutely no structure can lead to unproductive and unfulfilling days that blur into one another. 

 

But here’s the good news: you get to be the architect of your ideal day.

 

Think about it. You’ve spent most of your life adhering to schedules dictated by someone else – your school, your job, your kids. But now, it’s up to you to create your new retirement routine and build productivity-boosting habits.

 

The key is to create a routine that caters to your newfound clarity and specific goals (aka Steps #3 & #4). It’s a reliable way to make sure your interests, energy levels, and ideal lifestyle are top priority – they need to be bolstered by the right retirement structure.


What’s more, research tells us that routines are an essential element in creating a meaningful life. Studies show that people who enjoy routines tend to have more fulfilling lives, and following a routine can make even the most mundane days feel meaningful. 

 

why you need a retirement routine: for more meaning and purpose, for better sleep quality, for improved mental health and less stress, and more self-discipline

 

And remember, it isn’t about filling up every hour of your day with activities. It’s about fitting into your daily structure all the various pieces – because you can have it all: 

 

  • Sense or purpose, relevance, meaning
  • Time for your responsibilities, duties, chores
  • Freedom, spontaneity, leisure, relaxation
  • Social activities, fun, play time, events

 

And the right retirement routine (coupled with clarity first) can make this happen.

 

#6 Embrace Change & Cultivate Growth

Hating or resisting retirement won’t make it go away.

 

Change is inevitable in life, and retirement is one of those (very) significant shifts. It may seem daunting, but it’s also an opportunity to redefine who you are and what you want from life. 

 

So try to embrace this change with open arms. You’re not just retiring from work; you’re stepping into a world of exciting possibilities.

 

Your growth should never be limited to your career or younger years. Remember that spark of curiosity and learning you had as a child? 

 

Well, it’s time to reignite that flame… and then some. Retirement is your golden ticket to explore new interests, learn new skills, and challenge yourself in ways you never thought possible.

 

And don’t think of it as just a time to relax; it’s a continuation of your life journey where growth and learning never stop. Life isn’t compartmentalized into neat phases of education, work & family, and relaxation. 

 

In the modern world, these aspects are intertwined and overlapping. And your retirement should reflect that. 

 

it's a myth that life happens in three clear linear stages, it happens in cyclical stages
Life doesn’t happen in a linear fashion with three clean phases

 

It’s easy to fall into the trap of thinking that how you age is genetically determined, but that’s just not true. 

 

In fact, studies show that lifestyle factors such as physical activity and cognitive engagement can account for as much as 70% of age-related memory and cognitive changes. 

 

So, take the reins and cultivate your growth and development. With a positive outlook and engaged lifestyle, the sky’s the limit for what you can achieve in retirement.

 

Change Your Retirement Narrative from Hate to Love

Retirement isn’t a full stop, it’s a semicolon. It signifies a pause, a breath taken before launching into an exciting new chapter in the story of your life’s journey. 

 

Feeling unsettled or apprehensive about this change is completely normal (in any change, for that matter). But it’s essential to see retirement not as a period of stagnation, but as an exciting phase of self-discovery and huge personal growth. 

 

Here’s how you can do just that:

  • #1 Recognize your feelings — it’s natural to feel a mix of emotions, so take a moment, acknowledge them, and know that it’s okay not to have all the answers right away
  • #2 Discover what matters — uncover what lights you up from the inside out and make room for more of what brings you joy
  • #3 Find clarity — take some time to reflect on where you are and where you want to go and dig deeper into your retirement purpose
  • #4 Set goals & commit — after finding clarity, set relevant goals that fill you up with excitement and commit to achieving them
  • #5 Tailor your routine — create a routine that suits your newfound clarity, which should be filled with activities you love as well as pieces from all 5 Rings of Retirement
  • #6 Embrace change & cultivate growth — don’t shy away from the changes retirement brings; instead, welcome them with open arms and an open mind for growth

 

May you reframe the narrative around retirement. Change it from a phase of life that you dread and hate, to one that is eagerly anticipated. Embrace the ups and downs and thrive in the face of challenges.

What's Your Retirement Purpose?

These 10 questions can make all the difference
portrait of Cyn Meyer, founder of Second Wind Movement and a certified retirement life coach
Cyn Meyer 

Retirement Life Coach

As a certified retirement life coach since 2018, Cyn has helped thousands of older adults turn their retirement years into remarkable years full of growth, purpose, and passion. Through her signature program Rewire My Retirement, she helps people achieve their best life across the 5 Rings of Retirement, which covers topics Growth, Community, Health, Giving Back, and Finance.


Cyn combines specific life coaching tools, neuroscience, and her extensive background in marketing (spanning 17 years) to make a powerful impact with Second Wind Movement – an organization dedicated to providing educational resources and coaching for seniors.

With meticulous research, insight, and passion, Cyn’s mission is to usher in a new wave of positive experiences for generations of retirees.

portrait of Cyn Meyer, founder of Second Wind Movement and a certified retirement life coach

Cyn Meyer 

Retirement Life Coach

As a certified retirement life coach since 2018, Cyn has helped thousands of older adults turn their retirement years into remarkable years full of growth, purpose, and passion (beyond the stereotypical financial planning side of retirement). 

She combines specific life coaching tools, neuroscience, and her extensive background in marketing (spanning 17 years) to make a powerful impact with Second Wind Movement – an organization dedicated to providing educational resources and coaching for seniors.

With meticulous research, insight, and passion, Cyn’s mission is to usher in a new wave of positive experiences for generations of retirees.