Why Ask Why?


As parents of a three year-old, we can tell you that being a parent is the best thing that has ever happened to us.  However, anyone who tells you that being a parent is all butterflies and rainbows is quite frankly full of it.  There are several phases of your child’s life that simply suck.  Any parent can’t wait to get through them.

As a new parent, it is an awesome feeling to bring home your newborn.  Until an hour after you put them to bed when they start crying.  And then the next hour.  And two hours after that.  And another hour later.  Night after night after sleepless night.  AAAAGH!  Please just let me sleep!

Then there is potty training.  I never spent much time around kids.  I did have a dog growing up and we now have cats.  Surely a kid is smarter than that.  If you can train a cat to go in a litter box in a day or two and a dog to go outside in a week or two, it can’t be that hard to potty train a kid.  I honestly had myself convinced of that.  Over two and a half years, hundreds of dollars of diapers, and countless sights and smells I could never have imagined tolerating before becoming a parent, I realized I was very, very wrong.

Our newest annoyance is the why phase.  It’s time to eat.  Why?  The sky is blue. Why?  Put on your shoes.  Why?  Go to the potty before we get in the car.  Why?  BECAUSE I SAID SO!

What to Do?

There are no real positives that come out of getting no sleep. Parents are groggy, grumpy and short-tempered, and the kid feels the stress.  It becomes a vicious cycle.  The sooner everyone can get on a normal sleep schedule, the better.

Diapers are a massive expense, are horrible for the environment, stink up your home and are simply gross.  The sooner you can be done with them, the better.

But the “Why?” phase.  This is something a little different.


BECAUSE I SAID SO!  This is a phrase that goes through my head at least 50 times every day in response to that one word question.  But rarely do I let it come out of my mouth.  On one hand, hearing that single word over and over and over drives me insane.  On the other, it is the word that most excites me about being a parent.

The coolest thing about having a kid is observing their love of learning and experiencing new things.  Everything is new and exciting.  Every day is an adventure.  Wanting to know why is just an extension of that.  The thing that I want most for my child, even as much as good health, is to never lose that love of learning, growing and seeking new experiences, adventures and information.

The Power of ‘Why’

As we write about our journey to financial independence and early retirement at a young age, there are many factors that have played a big role.  However, if I had to give one reason why we are where we are, it is because we continue to ask the most simple question.  Why?

‘Why’ Got Us Where We Are

Like most college students who have to put themselves through college, Mrs. EE received the offer of loans to pay for her tuition, books and even living expenses.  Luckily she asked why.  Why would someone want to give her all of this money in unsecured loans?  Because they’re making a ton of money off of the interest and you can never walk away from the loan.  In return, you get to learn to live above your means while just starting out.  No Thanks!

Like most people starting out, we watched most of our friends buy the nicest and most expensive cars they could “afford” as soon they got out of school, and almost all bought with financing.  Luckily we stepped back and asked why.  Would a fancy car make our lives better or just drain our resources?  We decided to just drive our old beaters!

Most people allow their lifestyles to inflate as fast as their incomes.  Fortunately, we asked why.  We were already pretty happy with our lives.  Now we had two professional salaries.  Why not just bank one and save it for a rainy day?  Why start spending money on designer clothes and fancy cars we could care less about just because we could now “afford it”.  It’s a strategy that has worked tremendously well to build assets and put us in the position we find ourselves in today.

Not Asking Why Also Got Us Where We Are

Our biggest financial mistakes have all come from failing to ask why.  We are a society that places great value on fitting in.  There is little value placed on independent thinking.  Unfortunately, we are not immune to these thoughts and pressures from time to time.

“Investing is very complicated and you should hire a professional to manage your money.”  Unfortunately we never asked why.  If we did, we would have learned that investing is a skill that can be learned just like any other.  It is a skill that can make you as much or more than any other you will learn. If we simply asked why, we would have learned that most “professional advisors” available to low net worth individuals are merely trained salesmen.

“You should choose an advisor by getting a referral from someone you trust.”  We never bothered to ask why.  Most people, even those that know how to make a large amount of money, don’t know how to manage and invest it.  Not asking why has cost us hundreds of thousands of dollars in the long term.

“A house is a great investment.”  Unfortunately, we never asked why.  We just followed conventional wisdom and since have seen our time drained caring for a house far too big for our needs while we also wasted money paying for upkeep, utilities, taxes, etc.

What Makes Us Ask Why Now?


As we approach financial independence and early retirement, we continue ask why.  Here is some conventional wisdom we are currently questioning.

It is very risky to quit my job because medical insurance is very expensive.  Why?  Will buying our own health insurance in our early retirement be any different from what millions of entrepreneurs are and have been doing?  Do people who say this bother to investigate what the ACA is and how it works?  A recent post from GoCurryCracker looks at this issue in-depth.  While planning for health insurance is complicated and very  important, if planned for properly the new laws can be very favorable to early retirees.

We can’t split our time between different parts of the country while raising a young child.  Why?  Most people can’t because their lives are centered around their jobs and the need to make money.  We are carefully positioning ourselves to be location independent and financially independent.  While most people live their lives around work and fit in things like family and passions, we are building our lives to focus on family and passions with the ability to fit in work as we want to bolster our financial position.

You can’t quit working while raising a young child.  It is simply too expensive.  Why?  Don’t people who make far less money than us manage to raise children every single day?  Do we have to spend massive amounts on our child just because we can?  Could it possibly be more valuable to create more time to spend with our child than to spend our time making money to spend on toys, designer clothes, and other material things?

You should accumulate assets of at least 25X your expenses to be financially independent.  For an early retiree even this may not be enough.  Why?  I think this rule may be far too conservative for us.  The 4% rule assumes that you will never make another penny of income.  I have been strongly influenced by the writing of many other early retirees including Jacob Lund Fisker, Todd Tresidder, Darrow Kirkpatrick, Mr. Money Mustache and GoCurryCracker.  They all are continuing to make substantial income in their “retirements”.  The “Mad Fientist” talks in this recent podcast about still not pulling the trigger on his early retirement because he makes such good money and has created working conditions so favorable to him that he feels like quitting his job would be like throwing away a winning lottery ticket.  With our youth, skills, interests and desire to contribute to the world, it is far more likely that we will make too much money in retirement and find we have over-saved before we will ever run out of money.

Why Ask Why?

The simple act of asking ‘why’ more often than not has put us in a great position to achieve financial independence by the time we’re 40 years old,  after working for 15 years.  Failing to ask why in a couple of key situations has been very costly and is the reason we are not already financially independent.  Continuing to ask why is allowing us to shape the lives that we want instead of living the way society says we’re “supposed” to.  It’s that simple.  That’s why you should be asking why too!

Are you asking why enough or do you spend most of your time simply following the crowd?  What things make you ask ‘Why’?  Share your thoughts below.

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24 comments on Why Ask Why?

  1. We are also in the “why” stage with our kids… I try to encourage it, but it does get frustrating. Lately, I’ve been trying to turn it around to get him to think about the question more. Anyways… you make a great point that always questioning is key. We reached the same conclusion as you about that 25xs may be conservative for us, because we both have some passions we want to pursue that will make income throughout the years. I think to blindly follow anyone’s “rule” is not always the best idea - always ask WHY!

    1. I’ve been reading along as you’ve waited out the layoff scenario. Seeing your recent post about wanting to teach, I agree that it sounds like you’re much like us in that you have interests and passions that will make you money once you are FI. Therefore the assumptions behind the 4% rule with a traditional retirement really don’t apply to either of us.

  2. I love the correlation with kids asking “why” and then what we grow up to do as adults. I find myself always questioning everything, so if you drill all the way down and finally exhaust just about every “why” question, I think you get to a result that’s much more thought out.

    As a programmer, when I’m testing functions, “why” solidifies that a program is working correctly so translating this into life can be invaluable - especially when the “why”s are financial and mistakes can cost you.

    1. I work with many teenagers and college students. I find it interesting and honestly kind of sad to compare the curiosity of a young child with the lack of curiosity of many in that age group who simply want to fit in and are far more worried about getting good grades and collecting degrees than actually learning.

    1. I couldn’t agree more. In addition to earned income as I focused on, the 4% rule also doesn’t factor in other sources of income such as inheritances, SS, etc. We also don’t factor in our home as it is an expense rather than a source of income currently. However we can easily downsize and invest the difference or even in a worst case scenario use a reverse mortgage down the road. We could also decrease spending as needed. there are many options.

  3. Nice to see you back — twice in one month! 🙂 I can only imagine how tiring it must get to hear “Why?” 50 times a day, but I love how you guys are thinking about it. Nothing about early retirement is conventional, and as soon as you realize that something so unconventional is so possible, it starts to throw everything into stark contrast. For us, it’s made us ask why we have to stay in the city to have well-paid jobs, or why we have to buy things just because other people do. Asking why has helped us find freedom to make our own decisions without worrying about what anyone else thinks, even before we reach our financial freedom. And you know we’re supportive of splitting your time across regions — you need to get in some time in the big mountains, too!

    1. Your recent post on this same topic inspired me to finally finish this post up as it has been sitting in the que for a while mostly written. By the time I’ve gotten around to posting, she is actually mostly out of that phase and onto the singing Mary Has A Little Lamb 24/7 phase. I’m actually missing just hearing Why? 😉

  4. Great article. Yeah, you got me at the “2.5 years of sights and smells I never would have tolerated before.” Ha, Ha.

    Our now 4-year old was ready to potty train for 6 months before her 3rd birthday but never did. She waited until her 4th birthday and on that day said “Ok, I’ll potty train today.”

    I LOVE that someday my child will be a stubborn-minded, independent thinker, but boy is it hard now!

    I like to ask “Why” in the business and investing world I find myself in. Why do we have to keep growing? Why do we have to get bigger? Why is “successful” owning 100 properties when 5-10 will satisfy all of my goals?

    I hear you on the health insurance assumption. That assumption has chained more people to the working world for long periods of times. I’ve been a solo-entrepreneur since the beginning, and I’ve always paid for my own health insurance. The ACA has a lot of pluses and minuses that can be discussed, but there is no doubt it’s changed the game for entrepreneurs with preexisting conditions or FEAR of getting a pre-existing condition. I agree that the gocurrycracker summary was super-helpful.

    1. Kids are quite a challenge, but the most fun I can ever imagine.

      Great questions about the need to always get bigger and have more. Figuring out what is enough and learning to be satisfied is certainly a challenge we also face.

      Good insights on the ACA. Working in healthcare, I see the ACA much more as a further complication of our already overcomplicated tax code than anything that really changes how health care is delivered. The one positive for anyone is eliminating fear that a medical catastrophe could wipe you out financially by allowing you to buy health insurance without being tied to a job or discriminated against on the open market.

  5. Failing to ask why in a couple of key situations…

    We completely agree! The big decisions about life, including financing higher education and purchasing a home, are amongst those that necessitate the frequent use of “why” questions. Regretfully, we didn’t ask “why” until many years later. Better late than never, I guess!

    1. We definitely did not always ask why nor did we get everything right. I had a lot of help and guidance from my parents on the college front, but Mrs EE had to figure that out on her own and to her credit she did. We think it is sad how many young people are buried in debt b/c they are able to finance a bloated lifestyle they can’t afford at that young age and are then stuck paying the bill for years and even decades. They often simply do it w/o ever thinking to ask “Why?”.

  6. WHY???!!! What a great question that is! Thanks for the reminder to examine life with this simple question, a question that, if asked at the appropriate times, can lead to a very fulfilling life that we choose and not some marketer. I love that you are coming around on the 25x thing as you realize that time waits for no one and if you want to live that life you imagine then you need to make some sacrifices, including sacrificing your security blanket of 25x, especially when you know income earning opportunities continue to exist even when you follow your dreams! Keep ballin you crazy elephants and hit a brother up sometime…we await your visit to beautiful Montana!

    1. We have never been married to the 25x (4% WD) rule, but do think it’s a pretty good guideline for when you have “enough” to stop saving. We remain pretty married to our timeline b/c it is not very far off, it allows us to get the benefits of full time employment even while we each work essentially part time while burning through vacation time, we are somewhat limited on what we can do w/ the little one at this age and it should give us time to catch up on saving from past mistakes and get ourselves into that 20-25X ballpark. It also allows us to be very comfortable making a very small income which has many tax benefits once we are done working b/c we have to. When factoring in all things, we like our plan even though we would love to be FI now. Glad to hear you’re getting settled in Big Sky country.

  7. Love this post. It reminds me of a video my parents took of me as a little girl asking my grandma, “But why, Grandma? Why?” over and over again for a good 30 minutes. The whole time, she patiently answered me as I interrogated her after, every answer she gave, with that same question. As cute as that moment was to my parents, I’m sure my grandma felt the same way you say you did in this post and just wanted me to give it a rest already. I continued to carry that knack for questioning throughout my childhood and adolescence (by which time my parents found this curious habit less cute and more of a challenge of authority) and continue to ask “why” to this day. I hope I will always remember to ask why, especially while making bigger decisions and am so grateful that my grandmother allowed me, nay, encouraged me to keep asking her why - even if it annoyed her to no end. If it weren’t for people like her in my life, I wouldn’t be the FIRE-seeking, pain-in-the-butt I am today. 😉

    1. I think that spirit of curiosity has a large part in why we’re all on this unconventional path for our lives. Good for you.

      Now when should we expect to see this video over on your blog?

  8. Having kids of 3 and 5, I understand very well what you write. And the why is a challenging time. At some moments, I just go over the top with my answers, throw in a lot of complex details. That usually helps, they loose interest.

    but as you point out, asking why is a great skill. Do not take actions, quotes and advice from others for granted. understand where it comes from and what is similar or different between you and them.

    One of the rules I also question is the 4pct rule. The assumptions are too strict: no income anymore. I can not imagine that. Maybe not working full time, but half time, at moments that work out for me?

    The skin why in my life is now transformed in informing myself on what it takes to do something or to do the opposite. a skill never to loose.

  9. I love this post so much! I learn so much from my kids. They’re always trying to put things together and they were born thinking out of the box. It really makes you want to break out of the box seeing the way kids are able to problem solve (after the complete meltdown that often occurs just before the solution). Asking “why” can be annoying… but worth it.

    1. Agreed. Having a child is so much more fun and rewarding than I could have ever imagined. She challenges me every day!

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