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How to Avoid Hating Your Retirement

My parents hate their retirement.

This revelation floored me. How could that happen? How could you spend your entire life working and saving, come upon the freedom of retirement and just hate the ending?

how to love your retirement

My parents hate their retirement.**

This revelation floored me. How could that happen? How could you spend your entire life working and saving, come upon the freedom of retirement and just hate the ending?

Turns out, they’re not alone. Many Americans struggle to find a retirement that’s fulfilling and truly enjoyable.

Even the few who have saved enough, invested wisely, or have a pension, still find themselves with depression, anxiety, and regret about how retirement turned out.

But just because the reality is seldom as glamorous as the vision that we have in our heads, it doesn’t mean that we have to settle.

My Parents’ Retirement Dream

My stepfather always had the dream of sailing The Great Loop. The Great Loop is a voyage for boaters that takes them up the eastern seaboard of the United States, through the Great Lakes, and along inland rivers before spilling out into the Gulf of Mexico and rounding Florida to complete the loop.

Although he had owned boats all of his life, my stepfather never had one big enough to live on for months at a time. So, in 2003, my parents sold their house and bought a 40-foot boat to set sail on their retirement dream.

For my stepdad, tackling The Great Loop was always an item on his bucket list. But, he forgot one important part about his retirement dream: my mom likes to garden.

I know that it seems like a minor detail. You can garden anywhere and put potted plants on a boat. But, that wasn’t good enough for my mom. She wanted real dirt and a real a yard to dig in.

So, after years of bouncing around marinas in Florida, the realization that they would never set sail became too much to bear. My stepfather sold the boat, and they bought a log cabin in Georgia with plenty of dirt for digging and gardening.

My parents thought that they knew what they wanted to do in retirement. The reality was far less appealing than the dream.

What Does Retirement Actually Mean?

Thanks to financial independence, careful planning, and a generous pension, my own (and early) retirement is fast approaching. So, how am I trying to ensure that I don’t follow in my parents’ footsteps when it comes to life after work? Well, here are a few steps I’m taking to help define and achieve a successful retirement.

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Have a Plan

After telling a few of my coworkers that I plan to sit on a beach and write a book during my early retirement, most of them looked at me as if I were nuts. I’ve come to realize that retirement and our views of it are vastly different from one person to the next.

If you want to avoid the pitfalls of my parents and avoid hating your retirement, you need to understand what it is that you want out of retirement. And, unlike in my parents’ case, you have to communicate what you think your retirement looks like to your spouse and loved ones. Does your vision of retirement bliss equal your significant other’s dream?

Maybe retirement is the time to start checking long overdue items off of your bucket list. Or, maybe you should create a separate retirement bucket list. Whatever it is you are planning, the key is to actually have a plan and to share it with the person you’ll retire with in the end.

My parents didn’t really have a plan. Or, maybe they each had separate plans that they couldn’t agree on. I often think that my stepfather is miserable in his log cabin in the Georgia mountains hundreds of miles away from the ocean.

Maybe retirement isn’t necessarily a function of sound fiscal planning and goals. Retirement in actuality is very personality driven. While it may be a gross generalization, those who have dreams and a bucket list while working appear to have a very spirited retirement as well.

Perhaps your upcoming retirement is the perfect opportunity to break out of a rut. An opportunity to learn something new and work hard at it. Make a plan for your first year during retirement. Fill up the calendar and don’t look back. If you take the first year off from your retirement dream because you didn’t make a plan, you’ll lose momentum that you might never get back.

Take a Retirement Test Drive

Another way to ensure you have a retirement that you will love well into your Golden Years is to take mini-retirements before you leave the workforce. Now, more than ever, employees hop from one employer to another. Staying with the same company or two for an entire career is almost unheard of today.

According to the Harvard Business Review, more than 20% of millennials left their job within a year to pursue other work. Millennial job hopping is three times higher than older generations. Why not put those transitions and the breaks in between to good use?

As you transition from one job to the next, consider taking a small break. Have you ever dreamed of striking it out on your own as an entrepreneur, freelance contractor or writer after you retire? Why not take a few weeks between jobs to give it a shot.

Like college professors who receive a sabbatical, consider taking a month or two in the pursuit of your ideal retirement situation. Don’t wait until you fully retire to test out a retirement. What if you don’t like it? Mini-retirements, sabbaticals, or extended vacations are a great way to see how your dream retirement might play out in the real world.

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Track Your Projected Retirement Income

There are several useful online calculators like the AARP Retirement Calculator that can give you a snapshot of your retirement financial situation. You answer questions about your salary, savings, pensions, Social Security income, and several other financial factors, and the calculator will help you figure out what is needed to achieve the retirement you desire.

Younger investors can also plan for their retirement using tools from websites like Personal Capital. Personal Capital’s Retirement Planner lets you know where your finances currently stand based on your retirement nest egg. You can then make plans on how to build and grow your retirement plan in one centralized location. The planner even takes into consideration events like raising a family, buying a home, inheritances, and more.

These calculators also consider how long you plan on working and what you imagine your retirement lifestyle to be. Retirement calculators help you determine the amount of money you’ll need when you plan to retire and the sources of your retirement income.

As I’ve said before, your finances comprise just a portion of the equation. What about when you retire? What about planning for your retirement goals and what you’ll do in retirement? There are a few interesting life planning calculators online to help you with the transition into retirement.

AARP offers an online life planning calculator at The AARP calculator includes a series of introspective exercises. The site also provides ideas on how to clarify your goals, find the values and priorities that are important to you, and define a retirement that will work for you.

Start Early

My parents’ story breaks my heart. And, theirs isn’t all that unique. Far too many Americans are finding out that the retirement they always dreamed of is vastly different in reality. Everyone deserves a retirement filled with happiness and relaxation to do what you enjoy. After all, you earned it.

We spend so much time planning financially for the day we can quit working that we often forget to seriously think about what we are going to do in retirement once we get there. With a little careful forethought, open communication, and a few specific goals in mind, you can have a retirement that you’re proud of living until the end.

**Hank Coleman requests that you don’t tell his parents he wrote this.

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Hank Coleman is the founder and publisher of Money Q&A, a personal finance blog that focuses primarily on investing and retirement planning. Hank has a Masters in Finance from the University of Maryland and holds a Certificate of Personal Financial Planning from Kansas State University.

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About Hank Coleman

Hank Coleman is the founder of several popular personal finance sites such as Own The Dollar, Military Money Might, Money Q&A, and more. He is an entrepreneur and freelance writer specifically focusing on personal finance topics such as savings, investing, retirement planning and insurance. Hank's writing has been featured across a number of sites, including AOL Daily Finance, The Motley FoolFive Cent NickelSeeking Alpha,, Fox Business, Discover Bank,, and many others. Hank is a finance writer, financial planner and self-proclaimed investing junkie. He has a Masters Degree in Finance and a Graduate Certificate in Financial Planning. Be sure to follow him on Twitter @MoneyQandA and on his blog, Money Q&A.

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Haven Life is a customer-centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our editorial policy

Haven Life is a customer centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our content is created for educational purposes only. Haven Life does not endorse the companies, products, services or strategies discussed here, but we hope they can make your life a little less hard if they are a fit for your situation.

Haven Life is not authorized to give tax, legal or investment advice. This material is not intended to provide, and should not be relied on for tax, legal, or investment advice. Individuals are encouraged to seed advice from their own tax or legal counsel.

Our disclosures

Haven Term is a Term Life Insurance Policy (DTC and ICC17DTC in certain states, including NC) issued by Massachusetts Mutual Life Insurance Company (MassMutual), Springfield, MA 01111-0001 and offered exclusively through Haven Life Insurance Agency, LLC. In NY, Haven Term is DTC-NY 1017. In CA, Haven Term is DTC-CA 042017. Haven Term Simplified is a Simplified Issue Term Life Insurance Policy (ICC19PCM-SI 0819 in certain states, including NC) issued by the C.M. Life Insurance Company, Enfield, CT 06082. Policy and rider form numbers and features may vary by state and may not be available in all states. Our Agency license number in California is OK71922 and in Arkansas 100139527.

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