Did These Flip-Flops Lead Us to Financial Freedom?

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Did These Flip-Flops Lead Us to Financial Freedom?People hear that my flip-flops are now over 12 years old and love to say, “No wonder you were able to retire!”  But are my old shoes the reason we were able to reach financial freedom?

You might decisively be thinking that’s silly, but let’s talk about this a little more before you jump to a conclusion.

I think we all know that my shoes aren’t going to be the reason we were able to retire early.

But, I can also tell you that these flip-flops could really be a symbol representing part of what made it possible.

Being able to save more money means you’re either making more money or you’re spending less of it.

In our case, one way we moved closer to financial freedom was by trying to earn more at work, starting different side hustles, and buying rental property.

The other leg of this was spending less.  Frugality isn’t the only way to reach financial independence, but it’s still an effective method to do so.

Here’s a little bit of just how frugal I tend to be…


The flip-flops origin story

Did These Flip-Flops Lead Us to Financial Freedom?
Well, well, well… who’s that handsome devil?

When my brother got married to my now sister-in-law in 2007, they decided to have a beach wedding.  Definitely appropriate – they’d been living in Florida since they first got together in 2003.

He invited me to be his best man in the ceremony and as such, they decided on a certain look.  For us fellas as groomsmen, the attire was far from formal:

  • Long sleeve, light-blue, linen shirt (rolled-up sleeves, of course!)
  • Natural-color linen pants
  • Aviators-style sunglasses
  • Watch with a braided, brown band
  • Flip-flops from Target

I like that they went the casual route and I was also excited that I could continue to wear some of this later if I wanted (unlike renting a tux).

Somehow, I was able to find the email from my brother to the gang from 2006 on what we needed to order (I’m awesome like that!).  The pants had cost $55 and the shirt ran $64.  With shipping, it was $127.50.  More than the cost of a tux, but again, at least I’d own everything.

He gave us the sunglasses and the watch so no cost there.

And then there was the cost of flip-flops… $12.99.  Ok, $17.99 because they didn’t have my size at the store by us and I had to pay $5 for shipping… bastards!

So overall, it ran me just over $150 with tax.

It might sound like a strange idea, but it really came together well.

It was a great wedding and I think everyone had a blast.  Of course, it didn’t hurt that most of us were from other states and turned this into a giant Florida vacation!

I don’t want to share a photo of everyone for privacy, but you’re looking at a horrible picture of me right here from the wedding day.

And if you look closely, you’ll see one of the magic flip-flops in the photo:

So there they are 12 years ago in all their glory.  Somehow they still look pretty good…

Even the brand name hasn’t worn off!

I’ll keep wearing ’em until they break or wear completely down.  I’ve seen much worse.  In fact, Carl at 1500 Days was rocking a pair of Crocs that probably should have been buried a long time ago.

I’m sure the wear-down process will accelerate as soon as we move to Panama next month.  Being retired and living in a place other than Ohio provides a little more opportunity to sport flops instead of regular shoes.


Financial freedom from the flops?

I hate to tell you that the flip-flops I’m still wearing 12 years later weren’t directly responsible for our financial freedom.  Wearing a pair of flip-flops until they die just isn’t going to do it.

Wouldn’t it be nice it was that easy?!!!

However, I’d say that our frugality, in general, tremendously helped us reach that important milestone.

Although I made good money at my job, as a household, we weren’t making anything crazy.  Instead, most of our focus was on other avenues.

And the only two paths to be able to save more money are to either make more of it or spend less of it.  For us, the latter was one of our biggest financial freedom keys.

The mentality of not keeping up with the Joneses became the way to make larger strides in saving more.

The hardest part of that?  Not caring what other people think.  That can prevent you from always wasting money on looking pretty or buying the biggest, best, and newest crap.  It can also stop the waste of using some material item for a short amount of time before dumping it for a replacement.

If you haven’t read The Millionaire Next Door, you need to put that on your to-do list.  It’s a rare opportunity to see that millionaires tend to be the ones you think wouldn’t be and vice versa.  I read this book a little late in the game, but it’s such an eye-opener on how easy it truly is to get on the right track.  It’s a fantastic read!


Am I really that cheap?

I’m absolutely cheap on some things – there’s no denying that.  Clothes are one example.  I’m on vacation in South Carolina while I’m writing this and asked my wife, Lisa, to take a picture of me in my flip-flops to crop for this post’s featured image.

What I didn’t even realize until after she took the photo was that everything I was wearing is a perfect example of my care-less attitude on clothing…

Did These Flip-Flops Lead Us to Financial Freedom?
Damn, I haven’t aged a bit and just as good looking as ever! 😉

We already know about the flip-flops, but what about those sunglasses?  I spent somewhere between $5-10 on those probably a good 5 years ago at least.  The nose bridge is about to fall off and I already bought a replacement pair… but since it hasn’t broken off completely yet, I figured I’d keep wearing ’em until then.

I got rid of a lot of older shirts during our downsize in preparation for our move to Panama.  It makes me laugh then that shirts like this old 2008 fraternity reunion t-shirt are one of my “newer” shirts!

Those shorts have paint blotches on them from when I stained our deck a couple of years ago.  I don’t know where I got the shorts from, but they’ve got to be at least 10 years old!

And you know what – I’m just fine with it.  Clothes don’t make the man, in my opinion.  If I’m comfortable, that’s what matters – practicality over how good something looks.

Yes, I’m in the minority on this opinion, but when you’re not spending money on clothes, that’s more money that can be saved.  And more money saved equals one step closer to financial freedom.

The frugality extends to me cutting my own hair, how we shop at Aldi for most of our groceries, and how we kept our cars for long periods of time.

I could go on and on, but the point is that if you can let go of the things that don’t matter, your life suddenly becomes simpler.  And when you’re life becomes simpler, you can save a lot more money.

And obviously, the more money you can save, the faster you can reach financial independence.  When we hit a million-dollar net worth in 2017, the money itself wasn’t the exciting part.  The thrilling part was knowing we were almost to the point of our freedom number.


Is frugality the answer to financial freedom?

If you’re bringing in a ton of dough like some folks are, frugality may not need to be as high on your list.  If you’re able to save a large portion of what you’re making, you might not need to even worry about this too much.

However, for many folks earning regular incomes, frugality can be a real key to financial independence.  By spending less and saving the difference, you can put yourself in a fantastic position financially to get where you need to be much faster.

Additionally, because you’re learning to live on less, that becomes the number you need to support yourself.  Forget all the garbage you read in the media about needing a portfolio to support X% of your yearly income to retire.  Retirement needs to be based on your expenses, not your income.

If you have a household income of $100,000 and you’re happily living on $40,000 and saving the rest, why the hell would you need to have $80k/year to live on?  You need to focus on what your planned retirement expenses will be, not what your current income is today.

Frugality got us up to a 60% personal savings rate and that allowed us to retire at an early age.  But here’s what’s important – it’s a way of life for us, not a means to retire.

And by that, I mean that you can’t reach financial freedom and then go back to spending like a hog again.  It’s like diets – they don’t work unless you can make it a lifestyle change… as in for life!

Frugality isn’t something that pains us.  Honestly, we actually enjoy it.  I feel like we live like royalty and still do everything we want, but we love finding the deals for those things.  I’ve talked about how we love cruises, but we’re picky about what we book and how we do it.

Wearing old shoes doesn’t make a person a millionaire.  But I think it set the tone in our own path to financial freedom.

Find your happy medium.  Determine the point of living with less that you’re still comfortable with and able to enjoy life.  If that won’t get you to where you need to be to retire early fast enough, then it’s time to figure out some ways to increase your income.


Are you a frugal person?  Would you rather focus on frugality, making more income, or a combination of both?


Thanks for reading!!

— Jim

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18 thoughts on “Did These Flip-Flops Lead Us to Financial Freedom?”

  1. Richard Engelhardt

    I clearly remember that silver Chevy you had….I also remember how you kept driving that thing long after you got a promotion (and probably a raise to go with the new title)….Frugle ain’t the term.

    As my dear old late friend Dan used to say,,,,”You’re so cheap you couldn’t pull a needle out of your ass with a tractor”. LOL!

    JK – – well moslty anyhow ;).

    FWIW – I’m wearing the same clothes I wore long before I retired 9 years ago.
    But – I had that massive 100 plus weight gain – then the 110 pound weight loss – “speed bump” to contend with so lots of my ten year old stuff is nearly new.

  2. Those flip flops look like a prop from the ‘life of Brian’ film By Monty Python. Great story though. It’s interesting to see what gets others interested in personal finance and financial independence.

  3. Ha ha the good news is that when it comes to clothing, laziness equals automatic frugality. The other day I was looking at photos from a decade ago and saw myself wearing clothing that I consider new. This tells me #1 that caring less about appearance saves big $ and time. And #2 I am old…now to rock my hypercolor shirt and zubaz to the gym

    1. So true! My brother likes to make fun of me that I only wear promo t-shirts that I get for free… pretty accurate! Hopefully, we’re not so bad that we make those People of Walmart pictures! 🙂

  4. We have the same tiny dining table that we got in 2008 in our first apartment for $17 at Goodwill. We lovingly call it our “early retirement table” and anyone who eats at our house still sits there. If it ain’t broke, don’t upgrade it!

  5. Great story, Jim, and like with many of your stories I totally relate! Earlier this year my 17-year-old flip-flops finally bit the dust — in Hawaii of all places! — and it was kind of an emotional moment for me. I’d had them since I was a flat broke UCLA graduate student all the way until this year, when I’m on the brink of FI. The good news is that instead of dropping more money on another pair of flip flops I just re-purposed an old pair of quick-drying ultra-light trail running shoes into my beach shoes, so at least it didn’t cost me anything (and that’s important because we had travel hacked the entire Hawaii vacation — getting 8 days in Hawaii for free — and $20 for good new pair flip-flops would have totally blown the budget!!!)

  6. My clothes are like that too. I wear them until they fall apart. Nobody really cares what I wear anyway. I don’t have to go to any business meeting.
    We’re better at being frugal than increasing our income. So that’s what we focus on. We make good enough income and were able to save a big % of it. Making more is great, but you need to control spending first.

    1. So true – a lot of folks make the kind of money I can’t even relate to, but if you’re spending it all, you’re blowing your financial future. And I’m with you on the idea that nobody cares what you’re wearing once you’re retired – I’ve worn flip-flops every single day since mid-June now with the exception of Cedar Point and a day-long zoo trip… it’s been wonderful!

  7. Jim! You kick ass, man! I am just discovering your blog today because my wife just saw a post from Dawn on Facebook. I love it. Keep up the good work. I gotta say you haven’t worn the flip flops enough though – I still have them too and mine are waaay rattier than yours!

    1. That’s hilarious that I’m not the only one still wearing those flops, Bob! The good news is that since I’m not working anymore I should be able to wear my down a lot faster – I’ll catch up to you in wear and tear by the end of summer!! 😉

  8. I trade up phones every 5 years or more and haven’t changed cars in 11 years … and that saves money … curiosity question on income …. if your income is from the home country stock investments and your a resident retired in a second country, do you get taxed twice on that income … from both countries?

    1. Great question, Michael! Panama has a territorial tax system so they only tax you on income earned within their country. So we’ll only be paying taxes to the U.S. on our stock investments, thank goodness!! 🙂

  9. Hi,

    Being frugal is the way to financial freedom. Relating the flip-flops, I have seen that the flip-flops are sold for few hundred of dollars. This is applicable for well known brands. Such flip-flops are immediately struck off from the purchase list. It does not have to be expensive to be durable (as claimed by the promoter). As long as it serves the purpose, a cheap flip-flop is also good as the expensive one.


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