Why You Should Ask Why

Gretchen Rubin wrote a book on forming habits called Better Than Before.

There are a few other good books on habits (I recommend Charles Duhigg’s The Power of Habit), but Rubin’s big innovation was identifying different personality types. Some habit-building techniques work for some people, but there are very few universal approaches that work for everyone. Rubin divides her readers into four groups and then provides tips specific to each group.

Under Rubin’s framework, I am a Questioner.

“Questioners question all expectations, and they respond to an expectation only if they conclude that it makes sense. They’re motivated by reason, logic, and fairness. They wake up and think, ‘What needs to get done today, and why?’ They decide for themselves whether a course of action is a good idea, and they resist doing anything that seems to lack sound purpose.”

Beyond habit-building, this is a pretty good view into my permanent mindset. I ask “Why?” about pretty much everything, and if the answer is any variation of “Because that’s how we’ve always done it” then I’m out.

This may not describe your personality. I would imagine that I am not very normal.

But whether it sounds like you or not, I think we all could work to incorporate the power of the Questioner into our decision-making.

But Everyone Has Credit Card Debt!

There are a lot of situations where questioning the way things are usually done can lead you to a better life. I want to quickly touch on a few.

First: consumerism and credit cards.

Credit cards are ubiquitous. It often feels like buying with debt is just the way things are. We do it because our parents did it.

But our parents kind of invented it.

The first real credit card wasn’t introduced until 1950. They weren’t widely used enough to be profitable until the 1980s.

For the most part, our grandparents couldn’t buy things until they saved up the money to buy them. Our heavy reliance on debt is a new thing. The baby boomers made it seem normal, but that doesn’t make it a good idea.

When Do You Want to Retire?

When you think of “retirement age,” what do you think of? 65? 68?

In a 2015 poll, only 16% of people had an ideal retirement age that was younger than 60.

42% of respondents said their ideal retirement age was between 60 and 65, while 24% aimed for 65 to 70. 2/3 of people wanted to retire in that one decade of life.


Why is there not a wider divergence of retirement goals? Is there something special about your 60s? Or is it that this is just how everyone thinks life works?

Maybe in an era when people relied on pensions for retirement this mindset made sense structurally. But today we fund our own retirement.

We retire as early or as late as we plan and save for.

Obviously there are structural constraints. I can’t retire next year. But depending on how I balance my priorities I could retire anywhere from age 40 to age 90. There’s no longer much structural reason to assume that retirement in your 60s is the “right” answer.

Why Do We Think That Will Make Us Happy?

One example outside the world of money: happiness.

This is an area where the common knowledge misses the mark to an absurd degree.

We see our friends post pictures on social media and know that we’d be happier if we could just have that look, that car, that house. If only we just got the new iPhone or a bigger apartment we’d be happier.

This is the instinct that we’ve been raised with. When we were kids, commercials showed us how much fun we’d have if we just bought the newest toys. In school that turned to outfits and electronics. Once you hit a certain age it became cars and houses.

And everyone else does it. You work harder to make more money to get more stuff because that’s what you’re supposed to do.

But if you stop and think about it, it doesn’t make any sense.

We know more, newer, better stuff doesn’t make us happier. 

We know from our own experience. How long did that new toy make you happier? How long until you wished you could get another new car? 

We also know because there has been a ton of research on this. Each new thing just raises our baseline and we need to spend more and have more to get our next happiness boost. The hedonic treadmill means that we have to keep running faster just to stay in the same place.

Stop and ask “Why?” Then step off the treadmill and work towards real, sustainable happiness.

Becoming a Questioner

So how can you be more of a questioner?

First, I would advise that you can’t be someone that you’re not. If you are not naturally a questioner, then it is probably too difficult and far too time consuming to try to train yourself to do that all of the time.

From Rubin’s book:

“Because Questioners like to make well-considered decisions and come to their own conclusions, they’re very intellectually engaged, and they’re often willing to do exhaustive research. If they decide there’s sufficient basis for an expectation, they’ll follow it; if not, they won’t.”

I do exhaustive research on everything. I am the type of person that kind of enjoys writing a 4500-word analysis of a tax policy proposal that will be out of date in a month.

You may not. And it would be exhausting trying to be that exhaustive all the time.

Instead, identify the decisions that are most important. Start there.

Ask questions about decisions that involve your health. Stop and think a bit more about what really makes you happy. If that’s working out, ask “Why?” about other decisions that you tend to make on autopilot.

But start slow and don’t try to change your personality.

How to Avoid Analysis Paralysis

I also should add another warning: don’t allow yourself to be taken over by analysis paralysis.

Sometimes when you decide you need more information to make a decision, you hit a point where no amount of information feels like enough.

You end up not making a decision. And not making a decision is making a decision.

Some tips for avoiding this fate:

  1. Find sources that you trust. There’s a whole lot of information out there. If you are treating every source equally, you will never be able to come to any conclusions. The Flat Earth Society does not have the same level of credibility as NASA. A random article on Facebook does not have the same value as the CDC.
  2. Think about how important the decision is. Structure your research accordingly. Where you are going to eat dinner tonight does not require as much research as the next step in your career. Recognize when you might be overthinking. Get enough information to make an informed decision and then make a call and move on.
  3. Think about the worst case scenario. How bad would it really be if you made a wrong decision? Could you recover? Would it ruin your life? Usually our decisions are not as important as we think they are. Recognizing this can give us the strength to make a decision and get on with our lives.

So what about you? Are you a questioner? Where do you think the common wisdom is wrong? Let us know in the comments!

12 thoughts on “Why You Should Ask Why”

  1. So many wonderful pieces to this post. I’m also a questioner and can suffer from the analysis paralysis you touch on. I did it the other day and ended up not making a purchase because I could not get confident of the best vendor in time. I also agree that decisions should be made based on long term happiness. From my experience, people make shorter sighed decisions more often than not. I even received push back when I stated that my own personal finance blog was really about happiness as I was told “money is not all there is to happiness.” I agreed with the quote but having money can sure go a long way. It can help you be healthy, have more time to spend with who you want and do what you love. Obviously money does not equal happiness but it can sure help.
    Jason@WinningPersonalFinance recently posted…Super Coin Flip Risk AssessmentMy Profile

    1. I’m with you. And definitely with you on the happiness-based personal finance blog. I think every personal finance blog should, at heart, be a blog about happiness. When we stop and think about it, the whole point of trying to have more money is because we think it will help us live a better life and make us happier. Why not be direct about that? There’s no benefit to being the richest sad person.
      Matt recently posted…Conquering ProcrastinationMy Profile

  2. Interesting point about credit cards, Matt. Considering I’ve had one since I was 18 and got it easily as a college student 30 years ago, it’s probably something most people take for granted as always having been around rather than a relatively recent development. Same with the 30 year mortgage and the 60-month car loan, yet now they seem to be standards.

    I’m afraid that I’m an obliger…it makes it difficult for me to change bad habits unless I have a good support system in place. I’ve been better about putting one in place for money than most things.

    I’m a big one for credible sources…I get really frustrated when I have valid sources and someone completely disregards my comment because of one anecdotal experience, something they saw on Facebook or heard on the radio, or their “common sense.” Seriously? I know you can lie with data and statistics, but at least have some contrarian hard data. (For instance, if the Arizona Republic, a notably Republican-leaning paper, has multiple stories and editorials saying Joe Arpaio’s tactics were over the line and ineffective at reducing crime, then they probably were. Nevertheless, my husband’s half day in Mesa, where nothing happened other than we went through a roadblock, has convinced him that Arpaio was an effective lawman who has been maligned. Can you tell this is a continuing debate in our house?)
    Emily @ JohnJaneDoe recently posted…State of the Blog: September 2017My Profile

    1. Honestly, part of the reason that I started blogging was because I thought there was too much anecdote-based personal finance/financial independence writing out there and not enough data-driven writing. My early writing was entirely data-driven. And nobody read it. I’ve tried to make my writing more relatable while keeping to that hard data base.
      Matt recently posted…Conquering ProcrastinationMy Profile

  3. I am definitely a questioner, and have hit points off analysis paralysis in my life. My interests are that of a Renaissance (wo)man, which is to say I’m interested in too many things. Ha. So sometimes my paralysis isn’t so much related to one specific problem or issue, but rather related to which path to pursue with all of my dedication. I know that if I dedicate myself to something, I’m going all in and reading all the 4,500 word reports. But by pursuing one path of questioning, I know I will be diverting my attention away from another path that I care equally about. And I freeze. The opportunity cost of my energy allocation freaks me out.
    But when I finally get on a path and make a decision, I’m in deeply and passionately and often am going against conventional wisdom…or probably more accurately, conventional practice. Being a questioner has made my life path interesting, but not necessarily easy. I’m against conformity, but I imagine it has some perks at points.

    Just not when you’re racking up CC debt. 🙂
    Femme Frugality recently posted…Unique Economic Obstacles for LGBTQ+ IPV SurvivorsMy Profile

    1. I am with you completely on the wide range of interests. My original plan for this blog was “Matt Explains Things” where I would take complicated topics that interested me and break them down to be easily digestible. My wife is a communications director and vetoed that as way too broad to actually build an audience 🙂
      Matt recently posted…How to Control (and Minimize) Negative EmotionsMy Profile

  4. It’s great to ask questions. One of the reasons I started blogging was to keep myself accountable and constantly question myself.

    It’s easy to go overboard and get too indecisive, that’s why it’s also important to sometimes jump on an answer and go for it!

    Love the post, thanks
    Xyz from Our Financial Path recently posted…Can you do Better?My Profile

  5. I live the credit card debt example. It’s just so true, everyone else has credit card debt so why shouldn’t I? I can almost hear my mother now, “If everyone was jumping off the Empire State Building would you jump too?”

    I’m going to check out that book (I’ve already read The Power of Habit) and I won’t be surprised if I am also a Questioner.

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