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Planning Your Dream Retirement and Living Happily Ever After

Who doesn’t imagine the day they can retire and start living the good life? Finally stepping off the ever faster spinning gerbil cage rat race we call work? By planning your dream retirement, you get to decide what life will look like in the future.

When you think about it, with a life expectancy of another 20-30 years (or more), don’t you deserve to make the most of it? One way of doing this is to think of the 5 W's:

  • Why do you want to retire?
  • Who is important to you?
  • What will you do?
  • Where do you want to live?
  • When is the best time?

It can, also, be a bit like finding the elusive pot of gold under the rainbow, the one the leprechauns made off with years ago. 

Planning Your Dream Retirement?

Ideally, each of us financially prepare for the day when we can afford to leave work behind. Most of us have expectations of how it will unfold. These might include perfecting that golf game or doing a bit of travelling.

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The problem is there is usually something that goes sideways! According to US News, almost half (48%) of retirees left the workforce earlier than planned. This may be due to job loss, health issues, and other factors. The recent pandemic has created massive unemployment which will further exacerbate this growing trend.

Debbie's Story

While certainly not an example of planning your dream retirement, Debbie’s story reflects how many of us will need to adapt to changing conditions. Her plan was to work at least another 5-7 years and not retire at 55 years of age.

As an office manager, she used to love what she did. That was until they hired her new boss; egotistical, lazy, and incompetent. Soon, she was undervalued (treated like dirt would be more accurate) while doing her job and his. Of course, he took all the credit while she was blamed for anything that went wrong!

After three years of this insanity, the stress and pressures began to take a toll on her health. She was miserable to the point it was affecting her sleep. Her blood pressure spiked at alarming levels as she dragged herself into work each day.

The final straw was when he decided to discipline her (and further put her in her place) over a trivial matter. Read more of her experience at Bad Boss.

This became the perfect storm!

In hindsight, resigning was the best thing she ever did. Initially, she was going to take the summer off and look for work in the fall. In the meantime, we decided to create “Retires Great”.

In spite of what everyone says, starting a website is not quite as easy as it looks! 

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There’s lots to learn beyond the basic WordPress stuff. Especially as we strive to produce quality information that is of real value. Unbelievably, for us, this past year has flown by.

If anything, my only regret is not starting earlier. Even though her timetable was dramatically accelerated, we are content and grateful for all that we have. The best news is Debbie’s overall health and happiness have dramatically improved.

In short, Debbie’s “why” was not leaving a toxic work environment (well, maybe partly 😊) or she would have gotten another job. For her, it became a desire to do something meaningful and make the most of her life. Although we aren’t wealthy by any means, we are comfortable and live within our means.

Why Are You Retiring?

While this may seem like a foolish question, it might also be the most important one. The nature of the word “retire” implies to withdraw and retreat. Thus, we retire from work.

Instead, think about what are you retiring to? The "golden years", as they are known, will be the next phase of the rest of your life. Based on decisions you make; it can be as fulfilling and enjoyable as you desire.

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Having stated that, the decision to pull the pin is not quite so simple. With so many moving parts, seldom does everything line up perfectly.

More often than not, it’s a combination of factors. As in Debbie’s situation, these may combine in a manner where leaving work behind becomes, not only, appealing but desirable as well. These might include:

  • Tired of working and wanting a less stressful existence.
  • Desire to pursue new opportunities.
  • Meeting the age of eligibility for social security.
  • Health concerns for yourself or a loved one.
  • Loss of employment - voluntarily or forced.
  • Achieving sufficient savings and wealth.

Any one of these factors, or when several align, can influence the decision to retire. Whether you are ready or not is another matter.

Who is Important to You?

As corny as it might sound, Debbie is the love of my life and vice versa. We are, also, best friends. Almost every evening, we discuss our day and what is happening around us. Fortunately, we hardly ever run out of things to talk about. The reason I share this is you need to have a partner who, truly, is the most important person you have in life.

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The outbreak of COVID 19 has impacted everyone’s lives. The stay-at-home initiative certainly cast new light into our relationships. This may have strained them or provided the opportunity to grow closer together. How did it go for you?

In some respects, being under the same roof 24/7 is a mini-taste of what retired life will look like. Making those years look like you always thought they would requires you to have alignment and be on the same page. Discuss each other's expectations and what success looks like. For more information, check out “The Pathway to Marital Happiness and Fulfillment”.

Family and Friends

These recent times have raised issues of a lack of social interaction for many. Guess what? The same situation, to a lesser degree, occurs after leaving work. Work friends tend to dissipate and social circles slowly shrink over time.

With oodles of more free time this is, also, the opportunity to spend more time with family and friends. Become more active in the community or participate in activities / interests which will expand interactions with others.

As an example, a close friend of ours became involved with her local community league. She says she is busier than ever and gains a real satisfaction in volunteering her time in the many worthwhile events they organize.

What Will You Do?

What do you want to do?

The world is your oyster! (assuming you can afford it)

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Hopefully, it’s more than flopping into that favorite chair you have while watching the daily soaps and munching on Cheetos.

Good advice is to find some hobbies and interests prior to the day you retire. Maybe it's something you may have always wanted to do and now have the time to pursue it. Perhaps there’s a few projects around the house you want to undertake. For more thoughts, see “Ultimate Guide of Things to do when Retired and Bored”.

For myself, I am forever getting caught up with home improvements. A few years back, I replaced and expanded the entire deck. Being a handy sort of guy, I enjoy DIY stuff. This spring was Project Blueberry, creating an 18 x 3 foot bed for 7 blueberry bushes and some strawberries. Still working on it!

The point is we all need a reason to get out of bed. Something to look forward to that provides some sense of accomplishment. It could include volunteer work, a part-time job, or taking a course. Something that, both, stimulates you mentally and keeps you physically active.

Where Do You Want to Live?

When I was a little kid all starry-eyed about the wonders of the world, I once asked my father “If you could live anywhere, where would that be?”. Gazing down into my inquisitive eyes, he couldn’t help but smile as he said “Right here”. Needless to say. I didn’t fully grasp the meaning of his words at such a tender age.

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Shannon as a little buckaroo

A couple of years back, we met a wonderful couple on a cruise. They shared how they were fortunate to purchase their idyllic house on the shores of Lake Michigan. A bit of a fixer-upper, they had pretty much updated everything exactly the way they wanted.

Where do you want to live after you retire? Are you already in the home you always wanted or are you thinking of living somewhere else?

Perhaps a beach front home or a cabin off the beaten path? Lots of folks choose to downsize into a condo to reduce costs and maintenance.

Finally, after over 20 years of pondering my father’s wisdom, I took out a mortgage on an acreage. Best decision I ever made! Admittedly it’s been a labor of love with numerous renovations and outside projects (such as the pond).

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Shannon by the pond in our back yard

When is the Best Time to Retire?

In a perfect world, retire when you are ready. Most likely, this should coincide with age (ie. Social Security), achieving savings goals, and a desire to leave your career. Although no one can force us to retire, there are some circumstances where the choice may be out of our hands.

Planning your dream retirement requires flexibility and dealing with the things out of our control. This could entail retiring early and maintaining a more frugal lifestyle. It could, also, mean a part-time job to supplement income. In either case, the key is being grateful and making the most of what you have.

Another friend of ours drives a shuttle vehicle for a car dealership. The extra money helps offset his yearly vacations. More importantly, he enjoys the people he meets as well as getting out of the house.

Closing Thoughts

As you can see, planning your dream retirement goes far beyond just the financial aspects. It takes an integration of who, what, where, when and why to make the picture complete.

Presumably, you are going to be around for a while. You need to take responsibility for the preparation and transition to retired life. Having a plan and envisioning how you see it will help it become a reality.

As the great lady Eleanor Roosevelt said, “The future belongs to those who believe in the beauty of their dreams”. So, make this stage of life the most awesome and best one yet! Dream big!

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