The Five Whys

Sometimes the hardest part of repairing your relationship with money is understanding what the issue is in the first place. Is it something to do with your family history? Do you have a misalignment between your expenses and your values? Do you have different goals and ideas than your partner does, leading to friction and even fighting?

Even if you trace your problems to an issue like the above, it can be really hard to dig into what’s really going on, and how to fix it. When I get stuck trying to figure out why I’m resistant to something I know would be good for me, I sit down with a blank sheet of paper and use the “Five Whys” technique. I write down the problem, then below write down “Why?”. When I write the answer, I write down “Why?” below that. Do that five times, and you may be getting close to the root cause. Here’s an example that I’m having trouble with right now:

I keep “stealing” from my savings account to pay for silly things like coffee.


Because I like going to get coffee.


Because I work alone, and it’s nice to be around people sometimes.


Because I’m an introvert, so I find it easier to go to a public place where I don’t really have to interact with people.


Oh boy, it’s starting to get hard now. Why don’t I want to work harder on being out with people?

Well… it’s so hard to connect with my old friends when they work a regular J.O.B. Also, I feel like I’m not able to work when I’m alone.


I’m afraid I’m not getting enough done with starting my new business. I feel guilty that I don’t have more to tell my friends about how I’m doing. I don’t want to confront failure, so it’s easier to be alone among people.

Ahhhh, now I’m starting to get somewhere. And it’s not at all where I expected this to go! In the fourth why I gave two different answers, so I chose to go with the first one for now. It’s worth it to go back and do this again with the second answer, because I may uncover some more interesting tidbits. Bt right now, I wanted to explore my first answer. I’m basically spending money on coffee because I’m afraid of failure. This is something that is way more addressable then my original frustration. How do I confront this fear of failure, instead of drowning it in coffee? That’s a post for another time.

Final thoughts

I hope this simple technique helps you dig further into your personal issues with money. Remember, personal finance is mostly about the personal, less about the finance. When you are emotionally equipped to deal with your finances, they tend to start falling into line.

Note: you can find out more about the history of this technique on Wikipedia

Are you struggling with debt, spending, or your relationship with money? Schedule your free one-hour Money Empowerment Session to better understand your money stories, and get recommendations for taking the next step to healing your relationship with money!

I also run a group Money Empowerment Monthly meeting here in Portland! It is a safe, fun environment where you can talk about your greatest money fears and issues a facilitated peer group. You can sign up on Meetup.
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About the author

I work with individuals and couples to create a healthy relationship with money, in person or online. I can help you save money, pay down debt, and experience financial bliss! You can read more about working with me or sign up for a free session! Let's Talk »