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Tuesday, March 5, 2024

The Dark Side of Early Retirement: Why It’s Not for Everyone

Retiring early sounds idyllic. You finally have the freedom and time to pursue your passions and live life on your own terms. However, once you actually take the leap into early retirement, you may discover it’s harder than anticipated to stay retired.

Why Achieving Early Retirement Is So Challenging

First, let’s recap why early retirement is such a difficult goal in itself. To retire in your 40s or younger requires aggressive saving and investing over at least 10-15 years. Most early retirees have had high-paying careers that enabled large savings rates of 50% or more. They’ve accumulated investment portfolios substantial enough to generate adequate passive income.

Early retirees also often relocate to lower cost-of-living areas. Minimizing expenses is critical when living off passive income streams instead of employment income. Geographic arbitrage allows early retirees to make their money stretch further.

You May Struggle to Feel Retired Without a Pension or Safety Net

The average retirement age in the U.S. is 62. Retiring nearly 20 years sooner than your peers can feel strange or insecure. Those who retire at a traditional age frequently have pensions or Social Security to rely on. Early retirees lack these safeguards that foster confidence in being retired for good.

You Feel Responsible To Still Provide Despite Retiring Early

If you retire early while having dependent children or a non-working spouse, you may feel internal or external pressure to continue earning income. Walking away from stable employment income can seem risky and irresponsible if others are depending on you financially.

The Threat Of Running Out Of Money Looms Large

Even for early retirees without dependents, the possibility of outliving savings can cause anxiety. Some struggle to ever fully believe their portfolio can sustain them for decades without continuing to work.

It’s Hard To Break Habits And Identity Tied To Work

The average person spends 90,000 hours at work over their lifetime. Walking away from what occupied so much of your life is an enormous change.

Work Provides Structure, Purpose, and Social Interaction

Many are surprised by how adrift early retirement initially feels despite yearning for that freedom. Work provided structure, problem-solving, a sense of meaning, social connections, and intellectual stimulation. Replacing all that is challenging.

You Struggle To Shake Your Professional Identity

Particularly for those who found a lot of self-worth and identity in career success, feeling retired can seem like losing part of yourself. The adjustment to building a new identity is gradual.

Filling Your Free Time Takes Trial And Error

With unlimited free time for the first time since childhood, early retirees struggle to structure their days. You must experiment with different schedules, pursuits, and goals to find what provides satisfaction and happiness.

You May Initially Feel Bored or Lonely

It’s easy to romanticize everything you’ll do with free time pre-retirement. Post-retirement, you may deal with restlessness from too much down time or isolation from former workplace social circles. These feelings can tempt you back to work for activity and human interaction.

Reigniting Passions Can Be Difficult

Many early retirees have dreams of finally pursuing creative passions, volunteering, or traveling extensively. In reality, rallying the discipline and inspiration to regularly do these things after the initial retirement excitement wears off can take self-awareness and conscious effort.

You Never Run Out Of Opportunities To Make Money

While early retirement is possible, completely turning off that money-making brain can be nearly impossible for ambitious individuals. When opportunities present themselves, seizing them gives your days more purpose and impact.

Side Hustles Keep You Engaged

Early retirees often tap into entrepreneurial ventures, freelancing, or consulting to stay busy. These stimulate your mind while padding savings. Saying no to these opportunities contradicts the go-getter mentality that enabled saving enough to retire early in the first place.

Bear Markets Tempt You to Try Recouping Losses

Stock market volatility tests commitment to early retirement. After living through recessions that decimate your portfolio’s value, jumping back into income-generating activities to recover those on-paper losses can seem irresistible.

Just One More Year Syndrome Takes Hold

As with working longer to hit ever-moving retirement savings targets, early retirees fall victim to “just one more year” syndrome. There’s always one more bucket list item you need a bit more money for before you can retire for good. Chasing that elusive “enough” is tough to overcome.

Tips for Making Early Retirement Stick

While remaining retired after early retirement undoubtedly takes some soul searching and discipline, these strategies can help.

Build Your Identity Around Roles Other Than Your Career

Attach your sense of purpose to family, hobbies, passion projects, creativity, community, spirituality, or doing good in the world. When you broaden life’s meaning beyond career success, you won’t feel quite as rudderless without your job to define you.

Maintain Structure and Social Connections

Schedule regular activities, social interactions, and projects so your days have focus. Early retirement feels lonelier and more aimless if you have endless empty days to fill solely watching TV or puttering around the house. Stay engaged and accountable to others.

Live Below Your Means Regardless of Portfolio Value

Don’t tie spending to your portfolio’s fluctuations. Live on the returns your investments generate in conservative withdrawal rates, ignoring whether the total balance is temporarily up or down. The less you worry about recouping paper losses, the easier to stay committed to retirement.

Have a Retirement Hobby Budget

To avoid the retirement hobby trap of overspending while trying new pursuits, set a budget for investing in equipment, lessons, or related expenses. Know your hobby costs upfront so these experiments don’t inflate spending needs.

Move Away from Expensive Cities

Relocating away from major coastal job centers to affordable communities can dramatically reduce living costs. This both supports savings longevity and eliminates some temptations to work again simply because everyone around you does. Fly under the radar in laidback destinations.

Focus on Enjoying Retirement’s Freedom

When you catch retirement doldrums creeping in, consciously count your blessings. Reflect on the daily stresses when working that you don’t miss. Savor your liberty to learn, experience, and improve on your terms. Much of the world retires only when old, ill, or unable to work. Appreciate the gift to pursue your own purpose instead while health allows.

Frequently Asked Questions – FAQs

How can early retirees deal with the fear of outliving their savings?

Utilize conservative withdrawal rates and focus on living below your means to ensure a sustainable retirement.

Is it common for early retirees to struggle with the loss of professional identity?

Yes, many early retirees find it challenging to redefine their identity beyond their careers.

What is the significance of having a retirement hobby budget?

A retirement hobby budget prevents overspending while exploring new pursuits, ensuring financial sustainability.

How does moving away from expensive cities contribute to successful early retirement?

Relocating to more affordable communities reduces living costs and eliminates some temptations to work solely due to external pressures.

Can early retirees overcome the “just one more year” syndrome?

Overcoming the “just one more year” syndrome requires conscious effort to appreciate the freedom and independence already achieved.

What is the key to making early retirement a sustainable lifestyle?

Building identity beyond career success, maintaining structure, and appreciating the freedom of retirement are crucial for a sustainable early retirement.


Retiring decades sooner than the norm is an incredible feat requiring years of dedication and sacrifice. Ironically, that ambitious mindset and identification with professional success can make actually staying retired a whole new challenge. But with the right perspective shifts, consciously structuring your days, and choosing more affordable places to settle down, early retirement can absolutely become a sustainable new lifestyle. The independence and freedom are well worth continuing to nurture.


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