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Using the 5 Whys to Investigate Your White Allyship

While this blog is usually a place for discussing difficult financial questions, today I’m going to talk about how one of my financial tools is also a useful strategy for being a better ally to Black friends, neighbors, and colleagues.

In fact, a lot of the mindset work that I do surrounding money is related to the difficult work we all need to do to uproot the white supremacist worldview that we all swim in as Americans. Just as we don’t realize how much our money mindset colors our every decision until we start grappling with our unconscious beliefs about money, we can’t see how much the history of white supremacy in America affects our decisions and reactions until we start grappling with our unconscious beliefs about race.

One specific way that well-meaning non-Black Americans—particularly white Americans—unconsciously support white supremacy is by centering our emotional reaction, rather than focusing on the actual harm done to the bodies and minds of Black folks.

This is where the term “white woman tears” comes from, and you can see examples of this kind of emotional centering all the time, if you start looking for it. But white woman tears (and the gender-neutral “I don’t have a racist bone in my body!” response) are just the extreme end of the spectrum of centering white emotions in discussions of racism. At the other end of the spectrum are the well-meaning white folks who ask their Black friends and colleagues to do the emotional labor of forgiving them, absolving them, or giving them permission.

While this is clearly not the same as crying about being misunderstood after being called racist for doing something racist, it’s part of the pattern of relying on Black folks to do the work so that we can feel comfortable.

This is an incredibly common reaction among well-meaning white folks who want to be allies. I have done it many times, both before and after I started my intentional anti-racism journey. Recognizing when I am falling back on the notion that my feelings should be central is part of my work as an anti-racist.

Case Study: Wonder Woman


Back in 2017, I was absolutely charmed and delighted by the Gal Gadot Wonder Woman film. And for good reason: it was made specifically for me. The film centered the experience and reaction of white women superhero fans, and I felt 10-feet tall after seeing it. I even went out for a run after seeing the film.


Like, on purpose.


With the speedy feet and everything.

Then I saw that the film was criticized for not being intersectional. Though I got a heavy dose of I-am-woman-hear-me-roar power from the film, the film only portrayed Black women as caretakers and neglected to include people of color in the portrayals of power and optimism.

Because I wanted to love this film whole-heartedly, I took to Facebook, linking the above critique, and asking the following question:

“Did the movie really miss the mark when it comes to intersectionality all that badly, or are people looking for perfection?”

I then tagged two of my Black friends who are both comic book fans. I now recognize that my implication was clear to my friends: Please tell me it’s okay to love this movie. Be my Black friend who says the critics are going too far. Let me feel good again.

One friend had not seen it. The other told me that I had asked a very loaded question. She added, “As with anything regarding intersectionality, phrases like ‘all that badly’ and ‘perfection’ are quite subjective. There will always be someone who says ‘we've come so far let's be grateful’ and someone who says ‘this is not good enough and why should I settle.’”

I am so grateful for my friend’s willingness to engage with me. She lovingly pointed out what I was doing and gave me room to recognize why it wasn’t okay.

Why This Matters


This is the point in the blog post when I’d like to stop and remind everyone that pop culture is important.


It may feel petty or unreasonable or trivial to talk about a superhero movie when discussing something as big and ugly and deadly and toxic as systemic racism. But systemic racism is just that: part of a system. And our pop culture is one of the outgrowths of the white supremacist system we swim in, and it is one of the ways we can recognize the values of a culture. (Just think how often we make police the good guys in our entertainment, from Brooklyn 99 to Die Hard, for instance.)

And for those who think that the lack of intersectionality in Wonder Woman is a tempest in a teapot and that my friend shouldn’t have called me out and hurt my enjoyment of a harmless bit of fantasy, I’d like to remind you of two things:

1. I asked her, specifically and pointedly, because I was centering my emotions.

2. If we can’t even imagine a fantasy world wherein a Utopia of Amazonian women is equal, how can we possibly imagine justice and equality in the real world?

Introducing the 5 Whys

So if the problem is centering white folks’ emotions, what is the solution? This is where the 5 Whys come in.

This tool, which I’ve written about as a method for diagnosing personal finance problems, was originally developed by Sakichi Toyoda of the Toyota Motor Corporation to figure out the root causes of engineering problems. In the automotive world, a 5 Whys exercise might look like this example from Wikipedia:

· Problem: The vehicle won’t start.

· Why? The battery is dead. (First why)

· Why? The alternator isn’t functioning. (Second why)

· Why? The alternator belt has broken. (Third why)

· Why? The alternator belt was well beyond its useful service life and not replaced. (Fourth why)

· Why: The vehicle was not maintained according to the recommended service schedule. (Fifth why, and the root cause)

This ability to drill down to the root cause of the engine failure helps automotive engineers figure out how to fix the problem and prevent future problems.

The 5 Whys and Finances

When talking about finances, the 5 Whys exercise can help you figure out the emotional root of your money preferences. I often recommend readers answer the following question, before engaging in the 5 Whys exercise:

If I had $1 million, the first thing I would buy would be____________________________

With the answer to the million dollar question, you can ask yourself why until you figure out the emotional need that money is fulfilling for you. For example:

· Preference: If I had $1 million, the first thing I would buy would be a whole new wardrobe.

· Why? I hate dressing in outdated clothes.

· Why? Wearing outdated clothes makes me feel invisible.

· Why? I had to wear castoffs and hand-me-downs when I was a kid, and no one wanted to talk to me.

This example only took three Whys to understand the emotional meaning that money is acceptance and connection.

I also recommend that readers use the 5 Whys to help them figure out what’s keeping them from meeting their goals. For instance, if you’ve been beating yourself up for not signing up for a solo 401(k) since striking out on your own, you might use the 5 Whys to help you figure out what’s keeping you from doing the work:

· Problem: I still haven’t opened a solo 401(k) for myself.

· Why? I haven’t filled out the application form

· Why? I don’t know my beneficiaries’ Social Security numbers

· Why? I don’t have the kids’ paperwork

· Why? My ex has it

· Why? I am uncomfortable calling to ask for it

The benefit of the 5 Whys technique is that it helps you clear away the incidental issues and help you get to root cause or root emotion that is prompting your choices, actions, or preferences.

Using the 5 Whys to Investigate Your White Allyship

I’ve long used the 5 Whys to help readers and clients figure out their irrational financial impulses and choices. But this weekend, my sister mentioned using this technique to question our responses to racism. Drilling down into why you want to do something in response to the murders of George Floyd and Breonna Taylor can help you avoid burdening your Black friends and colleagues with your emotional response.


To use the 5 Whys to investigate your own response to racism, start with the action you want to take, and ask yourself Why? until you have figured out what is prompting your impulse to act. If the root turns out to be making yourself feel better, then don’t take that action.

If I had done this after reading about Wonder Woman’s troubling erasure of Black women, my 5 Whys would have looked like this:

· Action I want to take: Ask my Black friends if Wonder Woman is really all that terrible in its portrayal of Black women.

· Why? To hear that they liked it, too.

· Why? To get their reassurance that we all felt empowered by the film.

· Why? So I don’t have to think deeply about how people who don’t look like me were left out.

· Why? Because it felt so good for me to watch it.

By the fourth why, I would have clearly understood that I was not asking my friends for their opinions because I genuinely wanted to hear what they thought. I wanted them to reassure me so I could continue to feel comfortable in my love for the film without grappling with difficult truths about something I loved. I asked them that question because I was centering myself. I’m lucky to have good friends who were willing to lovingly push back on my centering of myself.

Let’s look at some other potential actions a white ally might be thinking of taking right now:

· Action I want to take: Contact all of my Black colleagues with a message of support.

· Why? To let them know I’m thinking of them.

· Why? So they know I’m here for them.

· Why? To make it clear I’m a safe person.

With this third why, it’s clear that wanting to contact all of your Black colleagues comes from a place of wanting to prove to yourself that you’re not racist. This is centering your feelings, and it means you should stop the impulse to act. (In the next section, I’ll talk about some things we can do instead when we realize we’re centering our own feelings).

Here’s another common impulse among white allies:

· Action I want to take: Lead the chants at a protest.

· Why? I’m a veteran protester and want to keep the energy going.

· Why? To help spread the message.

· Why? To make it clear that Black Lives Matter to all of us.

· Why? So people know that not all white folks are racist.

· Why? To reassure myself I’m not a racist.

Again, getting deep into the emotional realities of what seems like a well-intentioned impulse can help you recognize when you’re centering yourself. This isn’t to say that you shouldn’t follow a chant led by Black folks at a protest. That’s a great way to amplify their voices. But if you’re feeling the urge to lead a chant or otherwise center yourself, that’s when it’s a good idea to stop, observe, and listen, rather than follow your impulses.

What Should I Do Instead?

Going through this exercise can feel uncomfortable and overwhelming. You might start thinking that you can’t do anything without causing harm—and that’s because we are so used to centering white folks in all arenas, that we even cause harm when we are trying to help because we are centering ourselves.

But that doesn’t mean there’s nothing we can do. If you find that all of the actions you want to take don’t stand up to the 5 Whys scrutiny, try the following actions:

1. Do your homework. There is a huge amount of information available about the history of police violence toward Black and brown bodies, the history of white supremacy, the common lived experiences of Black folks in America, and the policy suggestions for creating a more just society. Read, watch, listen, and learn. And don’t show off your new knowledge. You’re not learning this to ace a quiz. You’re learning it to understand. Here are some lists of great resources to get started:



2. Make specific offers of help. Reaching out to say “let me know if there’s anything I can do to help” is a meaningless courtesy. We say it because we want to let people know we’re thinking about them—and we may even mean it. But it puts the burden of deciding what help is needed on the wrong person. Instead, let the folks in your life know the specific things you are willing to do to help. For instance, you could offer to take over a hated office chore for a colleague, or you could offer yourself as a contact and ride home for friends going to protests if you’re not able to attend yourself.


3. Donate money. Donating to organizations that are working to put an end to racist abuse is literally putting your money where your mouth is. Even if you cannot afford a big cash outlay, a small donation, or a recurring monthly donation of a small amount, can help these organizations do their important work. Some of the organizations that need our financial support include:



Or any local organization serving Black folks, that is also led by Black folks.

This Will Be Difficult and Uncomfortable

Working to root out racism and white supremacy in ourselves and our nation is a difficult and deeply unsettling process. It will hurt and it will be uncomfortable. We will all make mistakes, even with strategies like the 5 Whys in our back pockets. None of us is perfect, and the path to a more just society is not an easy one for imperfect creatures like ourselves.


But ultimately, we will never learn to decenter ourselves and make progress on this important fight for justice until we lean into hard tasks that make us uncomfortable.

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