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 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 a goal — retirement age, dollar amount, or life milestone —  then calculate what you’ll need to save and invest to achieve it.

At 27, I already had a clear vision of what my retirement would look like. I wanted to travel again like I did in my 20s. 

Age 55 was my goal because it was one year before my Dad retired. I wanted to “beat” him at a game he played pretty well. 

Having a target retirement age has served me well for planning purposes. It has motivated me to save and invest far more than your average aspiring retiree. 

Now that I’m within a decade of my original goal, I can refine my plan by knowing current assets, expected income, and long-term spending habits. 

As I approach retirement, I expect my expenses and lifestyle to be similar to my expenses and lifestyle today, with a few annual splurges on travel and some hefty college bills. I’ve built a lifestyle and business from which I don’t want to retire.

So, my retirement will look much different than what I pictured in my 20s. And that’s no surprise, in hindsight. 

My Ideal Retirement — Then vs. Now

Marrying, raising kids, and watching my parents, former coworkers, and neighbors retire have changed my perception of retirement.

Here’s how I saw my ideal retirement about 20 years ago:

  • Retire early (by age 55)
  • No work in retirement
  • Extensive travel (6+ months per year)
  • Prioritize healthy living, leisure, and social activities

Today, it’s more like this:

  • Spend time with kids, wherever they are
  • Support aging parents
  • Semi-retired at age 55 instead of fully retired
  • Extensive travel, hopefully 2-3 months of the year
  • Prioritize healthy living, leisure, and social activities
  • Engaged in the local community

When I disliked my career, I wanted to retire from it. 

But now that I enjoy self-employment and its flexibility, I expect to work longer even though we’ve hit a comfortable level of wealth.

I don’t consider myself retired today.

My youngest won’t go to college until I turn 58, so having an active income source is more logical than completely quitting sooner.

But it doesn’t need to be a salary. 

Most retirees I know maintain their previous lifestyle after retirement.

I once asked a retiring coworker if he had any special plans.

He said no, he would keep living the same way but without the commute or work.

It was the 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. They all agree they’d keep golfing the same $20 courses twice a week with each other if they won.

As people age and align their priorities, they build an ideal life they don’t want to change. Letting go of the time constraints of a full-time career makes it even better. 

But it can be a challenging transition.


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 specialized knowledge she acquired during her career was useless on the outside. She knew she was still valuable to the organization. So, she returned to work part-time.

RAND and various news outlets call this phenomenon unretirement, and it’s happening a lot.

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

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

Despite the trend, I’m confident this won’t happen to me when I fully retire. 

Like many others interested in early retirement, I was drawn to the idea of escaping my career because I chose the wrong one. 

Many of us realize, mid-career, that our current work is the path of least resistance to early retirement, even if it’s a suboptimal 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 50s 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 original goal to retire at age 55 is only seven years away now. But I think less about that milestone since reaching financial independence. 

When I reach 55, I’m optimistic our family will have enough savings and income streams (active and passive) to maintain our lifestyle, pay for college without borrowing, and have enough for retirement.

But I expect to keep working past 55 because I enjoy running an online business. It gives me purpose and the flexibility to work full-time or part-time and keep earning whether or not I turn on the computer each day.

Also, my youngest daughter will be home and in school for another 10 years. 

Once she’s in college, we’ll have more flexibility for retirement travel, and I’ll be less interested in working (as long as we’ve saved enough for college).

That takes me to 58 for starting college and 62 for graduation. My business can keep me occupied if my motivation lasts that long. 

Helping others make smarter decisions with their money is meaningful work. This has become increasingly apparent since starting this blog a decade ago. My day job never gave me that kind of satisfaction. 

Entrepreneurship is far more tolerable than an office job. It’s harder work but more rewarding. Earning money for longer reduces our risks from surprise hardships

Yet, I still could have 30 solid years of full retirement. How do we plan for a retirement that could potentially last 30-40 years?

Technology can help.

How to Reverse Engineer Your Retirement Savings

I recommend using a comprehensive retirement calculator like NewRetirement (review) or ProjectionLab to reverse engineer how much money you’ll need for retirement (traditional or not). 

Start with the goal (ideal full retirement age) and determine how much money you’ll need to support your desired retirement lifestyle.

The calculators step you through this process, starting with your current assets and income, and then they help project your expected income (Social Security, part-time, etc.) and investment returns in the future.

Calculators use financial models and visualizations to show what your income, spending, and drawdowns will look like in the future. They are must-have tools for detail-oriented DIY planners, giving us more confidence in numbers, especially for non-traditional retirement scenarios. 

A much less precise method to determine how much you need to retire is the 4% Rule of Thumb

First, track your annual expenses, then use the 4% Rule of Thumb to determine your retirement number. Roughly, it’s the amount of invested assets you should have on hand before retiring. 

The 4% Rule of Thumb says that given a set of conservative assumptions (e.g., portfolio returns, inflation), if you spend about 4% of your invested assets every year, your savings will last about 30 years.

You’ll need to save and invest 25X your annual spending to make the math work. 

For example, if you expect to spend $70,000 per year in today’s dollars per year in retirement, you’ll need to save $1.75 million before retiring. From that $1.75 million, you’d withdraw 4% ($70,000) every year, increasing the withdrawal amount by the inflation rate. 

Variations of this rule have been exhaustively modeled and back-tested in hundreds of ways, accounting for inflation and different investment portfolios. The rule of thumb holds true when applied to historical data over various periods of time, only failing when year one falls on a bad year (e.g., 1929 or 2008).

So you can use it as a rule of thumb for estimating a rough retirement savings goal if you don’t like calculators. But double-check your numbers as you near retirement and overestimate your spending needs to account for inevitable uncertainty. 

Do you have enough? 


Retirement doesn’t have a consistent definition anymore. Some people still retire from a lifelong career on a specific day and never work another day in their lives. 

But for people like me, that’s looking much less likely. And it’s a common refrain in the FIRE community — retirement isn’t the ultimate pursuit.

Financial freedom is the goal, allowing us to stop working if we wish or continue to pursue meaningful work.

How I perceive my eventual ideal retirement has changed in the past 20 years and is still reshaping daily.

It’s even changed significantly since I first published this post five years ago (rewritten this week). I was adamant about fully retiring at 55, I didn’t anticipate I’d be self-employed by now, and I wasn’t sure that’s what I wanted. 

But that’s what happened, and I’m enjoying it.

What does your ideal retirement look like today?

Photo by Jennie Brown on Unsplash



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Sure Dividend — A reliable stock newsletter for DIY retirement investors. (review)

Fundrise — Simple real estate and venture capital investing for as little as $10. (review)

NewRetirement — Spreadsheets are insufficient. Get serious about planning for retirement. (review)

M1 Finance — A top online broker for long-term investors and dividend reinvestment. (review)

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