Reader Case Study: The Best Laid Plans…

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Today I bring you a case study of a reader that planned diligently for early retirement. Life played out much differently from those plans. Still the process of saving and planning combined with the ability and willingness to adapt put him in position to live a rewarding early retirement.

Changing early retirement plans

Ken Lindsay retired 14 years ago at age 50. Today he generously shares lessons he’s learned in over a decade of early retirement and his plans as he enters traditional retirement years.

Take it away Ken…

Want Better Answers? Ask Better Questions

Do you have enough saved? When can you retire? What withdrawal rate will you use? 

These questions are where most of us start. They are not enough. 

You want to retire early. You know your number. Great! But why?

Focusing on the financial ‘trees’ risks losing sight of the new retirement “forest.” And by the way, your number is wrong.

Man Plans, God Laughs

My target was to retire at 40 but my kids expected to eat every day plus my wife and I wanted them to go to college. I didn’t retire at 40.

I retired at 50 and, wouldn’t you know it, that wasn’t the plan at the time. Don’t expect your journey to go as planned. It won’t. Once you accept that, you might just end up better prepared for what is to come.

For me the ‘retirement’ decision was nudged along by my employer of almost 30 years who decided the music was stopping and my chair was being pulled away.

While the company offered a way to seek another position inside it, a gut feeling told me the years-long trend I’d witnessed was unlikely to abate. I evaluated my savings and decided ‘the heck with it – I’m gone.’

That wasn’t the easiest thing to do given my nature, which was conservative enough to keep me in corporate America instead of fully acting on entrepreneurial urges, and which caused me to stay put at an old-school tech behemoth during the dot com craze.

My boss asked me if I was looking at internal opportunities. “I’m not sure I want to work for this company any longer” I replied without forethought or hesitation. Sometimes you know what you’re feeling even if you haven’t consciously contemplated it.

Mastering the Fundamentals

As an homage to the type of advice one often sees about retiring early, here is some lived-and learned financial advice. Spend less than you make. Start saving early. Learn how to invest well, at a minimal cost. Check out Schwab and Vanguard, and maybe Fidelity

Understand why equities will offer leading returns. Diversify and insure in a manner reflective of your risk tolerance. 

Related: Investment Risks — What You Don’t Know CAN Hurt You

Things will go wrong, but if you make the right big-picture decisions you’ll more than make up for them. Set limits.

Tax-advantaged accounts are great, but there is a role for cash in non-retirement accounts.

Related: The Benefits and Drawbacks of Taxable Accounts

Mostly avoid fads and “sold” annuities. 

Related: Annuities — The Good, The Bad, and The Ugly

Know how to budget and what you spend in a typical year.

Get good counsel. I sought wisdom from Bob Brinker, Dave Ramsey, and Jack Bogle.  I was lucky enough to speak with two of them.

A dear reader may be tempted to pass judgment based on an anecdote, or with 20/20 rear view vision. Fine, I’m 14 years retired and not yet 65, so it all worked out as far as I’m concerned. I’ve the luxury of not being overly invested in what others think.

Getting Comfortable With Uncertainty

You don’t know what the future holds so at some point, no matter how confident you feel in your financial position, it’s all a bit of a crapshoot.

You don’t know what the market will do just when you’re counting on the money. The US dollar could collapse. A nuclear bomb might drop from the sky. You could have a heart attack or get hit by a bus (or rideshare driver high on marijuana, to update the reference), or a germ might shut down the world and kill 7 million people…again.

So how would you react? Put off retirement even longer? Save even more? Worry about money all the time? Kick yourself when an investment doesn’t pan out exactly as you envisioned? 

I’ve learned there is a better way.

Early Retirement Reality

When you arrive at ‘that day’, expect it to take six months or more to decompress from the work-a-day world. There’s no need to get up early but you could. Some should. There is less reason to drive to a place (like an office), check the mail, or fret over a deadline.

If, however, you see no reason to get out of bed, there is a problem. [When that sentence becomes more true than funny, take note and action – even if just by reaching out to a friend.]

Related: Does FIRE Make Life Harder?

For me, it was also time to get to that long list of things I’d put off for when I had the time. Had I known more, I’d have done it with more of a sense of purpose, but I got to work (uh, I mean retirement).

Beatles in Hamburg

I went through multiple cycles of P90X in an effort to get into better shape. Genealogy research and international travel ramped up. Our flexibility led to some great trips including living like a local for 6 weeks in Hamburg Germany where our daughter happened to be studying. [Beatles fans might recognize the importance of the city’s Reeperbahn, where they refined their sound just prior to hitting the big time.]

We took a similar trip to Spain, cobbled together a bit of an MLB ballpark tour, and made the trip to see grandchildren just as often as possible.

It’s worth noting that we knew where we’d be living, and didn’t have the complications that so often accompany snowbird status, or split (or broken) families.

Assessing the Real-time Retirement Landscape

Because of my interest in teaching and research, I sat down with an acquaintance who was teaching at the University of Notre Dame. You can have a good future in academia, she said, but it might require a doctorate degree which would take an investment of a few years – and beware what getting on a tenure track entails. 

I did eventually teach finance and marketing at the college level, but as an adjunct.

I trained as a personal financial counselor, offering the service at no charge to motivated people in need, as a ministry.

While I didn’t need to work, I wasn’t against it. Applying my skills to a good challenge while working among highly capable people suits me.

I thought about continuing the consulting I’d done to help companies focus on the customer, for which I’d commanded a hefty hourly rate. Over time, I concluded I was lacking the passion it would require. Income isn’t passion.

Given my consulting skills and desire to reconnect in my community (I’d been on the road too much), I volunteered as a SCORE counselor – the RE literally standing for “retired executives”. That national program of the Small Business Administration has the mission to guide smaller and startup businesses.

I looked up contacts from the days when I was involved in local politics, one of whom went the extra mile to discover a relatively minor position would be opening up the next election because the incumbent would be stepping down.

The above might seem like a random list, but they started to inform me of the numerous factors to be considered. If you know what you want to do you are truly blessed. Otherwise, I’ve discovered, there can be method to the madness of figuring it out.

Related: Becoming a Beginner in Retirement

The Unexpected

Do you remember that box of chocolate from the movie? It applies to retirement. Here’s some of what I got.

My widower dad’s health deteriorated. I felt the need to visit more, time spent which I later truly appreciated. When he passed, there was my parents’ estate to put in order which, given my dad’s proclivities, required years of assessing and disposing of personal items.

Nobody likes to hear the phrase ‘global financial crisis’, but we hit a stretch where good investment opportunities – even those that might simply preserve capital – were elusive. Real estate crashed. Equities languished. Low returns on cash complicated financial decisions, to say the least.

To make lemonade we purchased a multi-unit foreclosure, renovated it, and became a landlord with healthy positive cash flow. While not in the plan, it was the right move.

The door opened to an elected position of more responsibility. That allowed me to create an award-winning park in the middle of a densely populated residential area which has been busy since the day it opened.

During the park design phase and long before the current craze, my wife and I were introduced to pickleball. We’ve enjoyed that very social sport ever since. None of that was in the plan.

The ability to see opportunity in changing conditions is a skill to augment all your financial planning. It allows you to handle whatever comes your way, can cost nothing but can pay off big time. I’ve yet to find the model – financial or otherwise – that simulates the impact.

The Failures and Setbacks

Chances are you will fail at something, or at least miss out on opportunities. I did.

I fully planned to learn how to play the fiddle. That hasn’t happened, despite some effort. Nor did learning another language.

A health issue which, ironically resulted from attempting to exercise more, led to surgeries and had me off my feet for a year.

Related: How to Live Long and Live Well in Retirement

Potential opportunities caught my eye but turned out to be a mirage. The fact that many of them were with non-profits who can still use the help opened my eyes to a perplexing reality, an exploration of which would require more words than available here.

And I never did find that next 20-year career – at least not yet.

Learning About Yourself

Sooner or later, you might learn things about yourself. Mine may appear simple, but they make for more enjoyable days.

  • I’m pretty used to doing what I want, when I want, and nothing I don’t – and am now in a position to make that happen.
  • I don’t schedule meetings before 10 am.
  • Being old fashioned about boundaries, I prefer to limit texts to between 9 am and 9 pm. Despite texts being an in-the-moment communication vehicle, almost every one I get can wait.
  • Among all the things I could do, working for someone else isn’t likely to be one of them.
  • I’d work, but I wouldn’t get tied down unless I found something worthy of a full commitment. My time and the flexibility to get up and go are just too valuable.
  • Working remotely makes a lot of things possible (he said, typing while working and exploring Europe). Today’s technology is just great.
  • Ever heard of flow? It might be worthwhile to look it up, including how it is linked with happiness. You can work crazy hard and enjoy it – go figure.

What Will You Do After Retirement?

In my almost 15 years of being retired, I’ve made it a habit to ask friends “When do you plan to retire?” The #1 answer is “I don’t know”. How will you know? What will you do? “I don’t know.”

I’m convinced that for many people, that won’t change. Retirement will mostly happen to them. It doesn’t have to be that way.

For someone who wanted to retire at 40 I was, I’ve concluded, woefully unprepared for all it would entail – despite having some mastery over the financial elements. Not unlike picking a college major, or settling into a career, there are numerous options on the one hand and (perhaps plodding) inertia on the other – a combination which can lead to indecision.

When a good friend of mine finally retired with ample financial resources, he stayed put in a small midwestern town to focus like a laser on improving the jail ministry he’d nurtured for years.  He is content, happy, fulfilled and, yes, busy. See “flow” above.  

I truly believe that if you know what you want to do, even if only as a starting point, you are blessed. Perhaps, like him, you can also be a blessing to others.  

If you don’t know your ‘next’, give it ample thought, starting now. Prioritize it over anything financial.

Entering Traditional Retirement

Now approaching the traditional retirement age of 65, my wife and I have weathered the health insurance storms, and just about tripled our net worth without yet touching a pension or retirement account, or drawing any social security.

I find myself focused less on finances and more on things I’ve done and still want to try, accomplishments and goals, travel experiences past and future, and my 13 years as an accidental public servant. I continue to seek challenges.

Wrapping Up (for now)

We’re all incredibly blessed by the prosperous times in which we live, almost to the point of being spoiled. Abundance is all around including opportunities to work – for pleasure or to meet needs.

Hopefully you’ll do well enough to not worry about finances but if you hit a rough patch, you can get over it. Lifestyles can be altered. Don’t get so soft that you fall to pieces worrying.

Remember, rebounds are real and safety nets abound.

If you happen to end up with more than you need, there are many places that will take your cash ranging from charities (Kiva and Health Wagon are favorites of mine) to schools.

Notre Dame now has a program (following the innovative lead of Stanford and Harvard) where you can pay almost $60,000 to hang out on campus for a year while trying to figure out a new direction.  As an added bonus, when it’s over they’ll ask you to boost the university endowment. (Such programs admittedly have a very narrow target audience.)

It never hurts to learn, or seek wisdom. It always struck me that the founding fathers paired life and liberty with the pursuit of happiness. I’d add, meaning and happiness are related.

Many of us now have the opportunity to move past the old definition of retirement, which consisted of a chance to stop working then enjoy a few ‘golden’ years. Some of us have the luxury of anticipating decades of retirement. This is new ground, so:

  • Save and plan – beyond the financial.
  • Understand the numerous ‘new retirement’ variables.
  • Know your first ‘next’ is important, even if it is a starter (temporary) one.
  • Use a North Star (or set of them) to guide you.
  • Develop the agility to learn and respond.
  • Pursue happiness.

I wish you the best.

Wrapping Up

Thanks to Ken for answering my call to share his reader story as a guest post. Share any comments or questions about his story below.

Ken can be reached at or We have no financial relationship.

If you would like to share your story, reach out to me at chris@caniretireyet. Over the past few years these reader stories have been among the most popular posts I’ve published:

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[Chris Mamula used principles of traditional retirement planning, combined with creative lifestyle design, to retire from a career as a physical therapist at age 41. After poor experiences with the financial industry early in his professional life, he educated himself on investing and tax planning. After achieving financial independence, Chris began writing about wealth building, DIY investing, financial planning, early retirement, and lifestyle design at Can I Retire Yet? He is also the primary author of the book Choose FI: Your Blueprint to Financial Independence. Chris also does financial planning with individuals and couples at Abundo Wealth, a low-cost, advice-only financial planning firm with the mission of making quality financial advice available to populations for whom it was previously inaccessible. Chris has been featured on MarketWatch, Morningstar, U.S. News & World Report, and Business Insider. He has spoken at events including the Bogleheads and the American Institute of Certified Public Accountants annual conferences. Blog inquiries can be sent to Financial planning inquiries can be sent to]

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  1. Bravo Ken. Thanks for your excellent post. I just stepped out of the corporate grind at 50 and your article is timely for me. I am in the midst of reinventing myself, a topic rarely covered in these forums. Your fourteen years have obviously been well spent and your accompanying advice is appreciated.

    1. Thanks for taking the time to comment. I agree there is a lot to learn from those ahead of us.

  2. Fantastic post, Chris! Thanks to Ken as well, for sharing. His story is so informative and in my situation… perfect timing. Really appreciate it. These case study type posts are simply the best! Thank you.


  3. Such a fabulous post – really got a lot from it. I am in my mid 50s and will be retiring some time in the first half of 2024. I have the financial part worked out and am excitedly planning the “what will life look like” part. Definitely won’t be sitting in a rocking chair, watching soap operas. Here’s to Time Freedom and the luxury of living life on your own terms!

  4. Thanks for the interesting post.

    Sharing life experiences (in addition to exploring relevant research and data) is such an integral and valuable component of this blog.

    Within weeks of retiring (with a full pension from a government position) I was offered a paid opportunity to facilitate a 14-hour class several times a year. The money is a bonus since I gladly would volunteer my time for this.

    This year, I trained online to become a certified SHIP (State Health Insurance Program) volunteer counselor. This is an unbiased, neutral one-on-one counseling service (with no affiliation to any commercial insurance company) to help individuals navigate Medicare options.

    Although I will not be age-eligible for Medicare for several years, I wanted to acquire some level of expertise now so I could make educated decisions later.

    I became a volunteer counselor to help others understand choices to maximize healthcare access while minimizing out-of-pocket costs.
    (PSA…enter “SHIP” via the internet for more information in your state.)

    Physically, I exercise five hours each week. I follow an intermittent fasting schedule and I eat semi-healthily (choosing “better” options with occasional treats) most days.

    Socially, I attend worship services regularly, visit home-bound parishioners each month, eat meals with extended family frequently and enjoy my animal companions. My husband loves me for who I am as I also love him (although he is much better than I am about not letting issues fester!).

    There have been hardships and sadness (chronic illness, deaths of parents, a sibling and of an adult child) but my life is fulfilling and I am grateful every day for my many blessings.

  5. $60,000 to hang out at a prestigious university to find oneself. I think that says a lot about what’s wrong with higher education.

    1. Pat,

      While I agree that is not where I would spend my money, that is the point of reading different perspectives and experiences. We all get to decide what we value and then spend our time and treasure accordingly. Again, I thank Ken for sharing his experience and insights. I personally gained a lot from reading it.


  6. Nicely executed, Ken! (That goes for your retirement, as well as your post.) The financial aspects of retirement are often in the spotlight because they’re such a critical component of this stage of life. But consideration of the emotional aspects is just as important if life in retirement is to be lived to its fullest. My sense is that you’re self-confident, introspective, focused, determined and that you’re a hard worker who can laugh at himself, roll with life’s punches and take advantage of a wide variety of opportunities that come your way or that you facilitate. All good qualities to possess in today’s society with social media attempting to impact our decisions on how life is to be lived. Thanks for sharing your perspective and your experience. May all of life’s best continue to be yours!

  7. Sometimes phrases just jump out at you: “If you don’t know your ‘next’, give it ample thought, starting now. Prioritize it over anything financial.” These are strong words, and my takeaway is that if you generally have a solid financial plan, it will ‘take care of itself’. What needs even more attention is your ‘why’ in retirement. I’m 5 months into retirement and in the decompression stage, but these big questions are starting to surface for me as I reach Ken’s-mentioned 6-month mark. Thanks to Ken for his message to look past the financial.

    1. TennisLVr,

      Thanks for reading and taking the time to leave feedback. I agree that Ken gave us a lot to think about there.


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