The Changing Realities Of An Ideal Retirement

Visualizing your ideal retirement at different stages of your life will drive you to achieve it sooner and may impact how you save for it.
I can describe my ideal retirement in three words.

Long and healthy.

If my retirement is long and healthy, I’ll have very little to complain about.

Beyond that, everything else is icing on top of the cupcake.

But like my four-year-old sugar-crazed daughter, I spend a lot of time thinking about the icing.

A Healthy Exercise

Have you thought about what you’ll do in retirement? Even if you’re young, it’s a healthy exercise to consider well before your exit date.

Visualizing your ideal retirement will drive you to achieve it sooner and may impact how you save for it.

Reverse engineer it. Start with the outcome and work backward to devise a plan.

The youthful tend to be the most optimistic. I certainly had a clear vision of what my retirement would look like when I was in my 20’s. I dreamt of it at the tail end of my backpacking adventure.

The idea was to go from being broke and living with my parents, to creating the perfect life with a loving wife and family and a lucrative career. We’d live in our dream house. Then after twenty-some years of masterful parenting, Mrs. Perfect and I would travel the globe for the remainder of our days.

This was in the head of 27-year-old without a responsibility in the world.

What I didn’t realize was building a career, finding a life partner, and creating a “perfect” life is not achieved with a pen and checklist.

It doesn’t happen in a straight line. And it’s never perfect.

Nonetheless, I did meet Mrs. Perfect, we have a loving family, my career and side business are lucrative, and we’re on track to reach our retirement goal.

But through it all, my vision of an ideal retirement has changed.

My Ideal Retirement – Then vs. Now

Besides a long and healthy retirement, I think about the specifics a lot.

Marrying, becoming a parent, and watching my parents, coworkers, and neighbors have changed my perception of retirement.

Here’s how I saw my ideal retirement about 15 years ago:

  • Retire early (by age 55)
  • No work in retirement
  • Extensive travel (6+ months per year)
  • Focus on healthy living and leisure

Today, it’s more like this:

  • Retire early (by age 55, perhaps earlier)
  • No work in retirement
  • Travel (varying year-to-year depending on our kids)
  • Focus on healthy living and leisure
  • Spend time with kids, wherever they are
  • Be supportive of aging parents
  • Involvement with the local community
  • Active social life
  • Be damn sure I have health insurance
  • Pursue passion projects (that might earn money)
  • Contribute to the greater good

Most retirees I know never drastically changed their lifestyle after retirement.

I recently asked a coworker who is retiring this summer if he had any special plans.

He said no… just going to keep living the same way but without the commute or work.

Same for a neighbor of mine. The first thing she did was remodel her kitchen. She’s not going anywhere.

My Dad and his golfing buddies talk about winning the lottery. All of them agree they’d probably just keep golfing the same $20 courses twice a week with each other if they won.

Perhaps because as people age and refine their priorities, they build an ideal life they don’t want to retire from. They just want to retire from the constraints of a full-time career and enjoy the extra time.


But a former coworker of mine retired about a decade ago and returned to work within a year.

She didn’t need the money. She was bored.

The decades of specialized knowledge she acquired during her career was useless on the outside. She knew she was still valuable to the organization. So she was compelled to return to work part-time.

RAND and various news outlets are now calling this phenomenon unretirement and it’s happening a lot.

Money and longevity both play a role in the unretirement trend. But a bigger factor is the desire to do meaningful work.

Some people really do enjoy what they do. Once they leave, they miss the work and struggle to find another purpose.

Despite the trend, I’m pretty confident this won’t happen to me.

Like many others with an interest in early retirement, I was drawn to the idea of escaping my career because of lack of interest.

Many of us realize, mid-career, that our current work is the path of least resistance to early retirement, even if it’s not the best career fit.

This realization can arise in the form of a midlife career crisis. As in, oh shit I chose this career and now I’m stuck. How can I escape?

We do the math and realize there’s an accelerated path to retirement that doesn’t require a career 180.

Then there are the people who love their chosen careers and don’t understand early retirement. One person I met through this blog asked me why do you want to retire? 

He was a Dad, in his 50’s, and loved what he did for a living. Has no desire to retire at all.

My quick answer to him was travel. But the full answer is more complicated.

Retirement Redefined

My goal to retire at age 55 is 12 years away. When I reach that age, I’m optimistic our family will have enough investment income and savings to leave full-time work and still pay for college without borrowing.

I’m unlikely to “retire” and start a new business or come back as a consultant as long as we prepare for that date.

That said, I enjoy earning money and might want to keep earning. I anticipate that being a more active investor in retirement will satiate that need.

But I could be wrong.

Writing is fun. Helping others make smarter decisions with their money is rewarding. So maybe I’ll keep writing or find another way to earn doing something I enjoy.

I also acknowledge that today’s rosy economy may not continue. Our family could experience some kind of hardship. Shit can happen and I may need to work beyond 55. I hope not.

Retirement plans can change leading up to the big date and in the years to follow. And since retirements can last thirty or forty years or more, priorities will certainly change throughout that time.

What I thought was my ideal retirement at age 27 is different than my ideal retirement today, which is different than what it will be at age 55, 65, 85, or hopefully, 105.

Which brings me to the topic that intrigues me the most. How do I save for a retirement that could potentially last 40 years?

How to Reverse Engineer your Retirement Savings

As I mentioned at the top, to reverse engineer your retirement savings, start with the outcome and work backward to devise a plan. There’s a common method to this and a more flexible method that takes longer but gives you more options.

The 4% Rule

The most common method for determining how much you need to retire is to project your annual expenses. Then use the 4% Rule to determine your retirement number. Roughly.

The 4% Rule says that if you spend about 4% of your savings every year, your savings will last for about 30 years.

For example, if you expect to spend $60,000 per year in retirement, you’ll need to save $1.5 million before retiring.

Variations of this rule have been exhaustively modeled and back-tested hundreds of ways accounting for inflation and different investment portfolios. It basically holds true when applied to historical data over various periods of time.

So you can rely on it as a rule of thumb for estimating your retirement savings goal.

A More Flexible Method

However, I am not basing my retirement planning the 4% rule. Instead, I’m pursuing a strategy whereby I create enough investment income in taxable accounts to cover essential living expenses perpetually.

I track the taxable investment income I receive in my quarterly income updates. At last check, my annual income earned from taxable investments (stocks, real estate etc.) is about $9,000. This income helped our family when I lost my job, and I intend for it to be an income baseline during my retirement.

As I make fresh investments, brick by brick, that number will grow. Since I’m still working, I currently reinvest any payouts I receive back into more income producing assets creating a compounding effect. And since many of the investments are in dividend growth stocks, the payouts grow naturally every time a company announces a dividend increase.

Covering most of our monthly living expenses with sustainable income streams will free the money in our tax-advantaged retirement accounts to grow for longer.

Eventually, the money in retirement accounts (the icing) can be used for travel, comfortable living, healthcare or assistance needs, and occasional luxuries.

Pursuing this more flexible strategy, combined with using the 4% Rule estimate our wealth and ability to retire, is a more realistic approach to saving for the type of retirement I want to have.

Because having the sustainable taxable income streams frees more money for unexpected needs, to help others, or even to pass on to our kids.

The downsides are two-fold. Building reliable income streams take more research and effort than simply putting all your money into index funds. And it takes longer to retire.

But this strategy allows for a more dynamic retirement. One that is less constrained by a fixed income, giving the retiree more flexibility to live their ideal retirement.

Photo by Jennie Brown on Unsplash

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12 Responses to The Changing Realities Of An Ideal Retirement

  1. Marc June 7, 2018 at 7:02 am #

    My ideal retirement is pretty similar to yours. I also hope to be able to stop working around 55 and I’d like to be able to travel a lot. I get bored extremely easily, so I doubt I would completely retire even if I could. But I’d like to have the flexibility to work on my own terms and take extended time to travel when I want to.

    • Retire Before Dad June 8, 2018 at 9:28 am #

      I don’t get bored easily. Probably because I have three kids. Any free moment I have there’s a hundred things I can do or enjoy by myself.

  2. Fritz @ TheRetirementManifesto June 7, 2018 at 7:55 am #

    Today is my last day of work. I’m 55.

    My dreams of what early retirement mean to me have changed numerous times over the years, and will likely continue to change post-Retirement. That’s how it should be, me thinks.

    What’s important is the mental process of thinking on it. I’ll let you know how it turns out. Retirement starts tomorrow. Wow.

    • Retire Before Dad June 7, 2018 at 7:59 am #

      Well, great timing on this one. I’ve obviously been following your story for the past few years. Incredible the day has come. Doesn’t surprise me to hear your ideal retirement has morphed and will continue to. Congratulations! A new story begins tomorrow!

  3. gayle June 7, 2018 at 7:56 am #

    WEll Im 56 and not close, so apparently Ive done something wrong !

    • Retire Before Dad June 8, 2018 at 9:29 am #

      Your situation is very common. Not being able to retire is normal! Don’t give up, you can still create your own ideal retirement.

  4. Oldster June 7, 2018 at 12:20 pm #

    I’m 59 and could retire, but choose not to. Mostly because of the uncertainty about health insurance. My wife is a 3 time cancer survivor (and 10 years younger than me) and we just can’t risk being uninsured.

    On the issue of unretirement, my father retired when he was 60 and went back to work at 60 1/2 and worked every day after that until he was 79. He just did not have enough to do. The planning for how you want to spend your retirement time is as important (maybe more) as saving the requisite amount.

    • Retire Before Dad June 8, 2018 at 9:31 am #

      Healthcare has become a major concern for everyone. Having just gone through the whole COBRA process, I’m less encouraged. To be insured and retire early, we just have to budget for it. That’s expensive, but it’s reality these days. Congrats to your wife for her victories. I can see how this would change your actions.

  5. Nancy F June 7, 2018 at 4:02 pm #

    Since finding you, I’ve found the missing link in my retirement planning – dividend growth stocks. I spent considerable time with your blog and checklists, asked successfully retired friends and family what they were invested in, and got busy. Stocks I’ve purchased have also been designated as DRIP status. I am very grateful to you for your work and advice. It will make a difference.

    • Retire Before Dad June 8, 2018 at 9:34 am #

      Thanks for this comment. It really means a lot coming from a reader. I spend a lot of time writing this stuff and sometimes it feels like no one is paying attention!

      DGI is a reliable strategy for income. Really about determining how safe a dividend is and trying to get the highest quality yield for your money. Glad to hear you’re successfully building income streams for retirement.

      • Rick June 18, 2018 at 2:21 pm #


        replying just to make sure you know that I am paying attention! And im pretty sure there´s a lot of people investing and planning retirement in a better way because of your posts.
        From Brazil, I´ve been following you for about 2 years, and making the necessary adaptations for my reality (basically taxes and pension accounts differences. Kids, travel passion and retirement goal age are equal), I can say you´ve helped me a lot with your thoughts and data.


  6. Mr. H&N June 7, 2018 at 5:38 pm #

    I think a lot about what to do in retirement. In fact, I consider whether I should wait and retire completely or just take a pay cut to work in something that I enjoy more. Unfortunately, I still have a looong time to think about it before the day comes but I know I need to have it figured out by then.

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