Ask Yourself "Why?"
Starting a new habit can oftentimes feel impossible. You’ll have a few good days, but then all of a sudden the momentum is gone. This week, I explore how asking yourself “why?” might help keep those new habits running by better understanding your core values.
If you’ve ever tried to make a habit stick only to fail a few days later, this week’s post might be for you.
It happens to me all the time.
I’ll come up with a plan for a habit I think is meaningful, but when the time comes around to start, I’ll feel like it’s easier to climb a mountain than to do this habit.
It happened when I started to write for this website. I knew on some level that I wanted to do the work, but I couldn’t bring myself to sit down and write at times.
A habit can be hard for us to begin if we don’t know why exactly we’re doing it.
One solution is to find the core value, the part of our identity, that is the moving force behind the desire. And sometimes, finding that value is as simple as asking ourselves, “why?”
Adam Grant and Brené Brown
The relevant moment in the interview starts at the 18:37 mark
Recently, I came across an interview between Adam Grant and Brené Brown.
Grant and Brown are both podcasters, academics, and authors. Grant is probably best known for his book, Think Again.
I’m guessing more of you have heard of Brown. Either in work training or on social media, her videos and content are everywhere. She’s done a few books and shows, but she really broke out with her TED Talk, “The Power of Vulnerability.”
In the interview, Grant puts Brown to the test by running through a value-finding exercise with her. He starts by asking why vulnerability is important to her, then repeats with variations of “why?” depending on her response.
Eventually (and rather quickly), she gets to her core belief, courage. Brown wants to be vulnerable because she inherently believes in the importance of being courageous.
Ask Yourself “Why?”
A lot of times a new habit doesn’t stick because we don’t fully explore why we want to do that thing.
If you want to eat healthier but aren’t clear with yourself on why you want to do so, it’s going to be harder to maintain that new diet.
Do you want to eat healthier to extend your life? Look better? If you’re able to tie in that habit to a core belief or identity, you’re much likelier to continue it.
It doesn’t matter if you want to eat healthier to live a long life or to get six pack abs. It all depends on what you want and value.
Brené Brown knows it’s important that she be courageous, which makes being vulnerable easier. Being vulnerable plays into the core value of courage.
One way to get at our core values is to ask ourselves the question “why?” repeatedly.

Some people will say to do this 5 or 6 times. I’m not convinced there’s a magic number, though.
Much like with the example in the video, there is a point where you just toss your hands up in the air and say, “because that’s who I am!” There’s the core belief.
I’ll give you an example.
Why Work on This Blog?
One question I asked myself as I was getting in the habit of writing this blog was, “why do I want to do this project?” Surely, it’s easier not to spend my free time this way.
I ran through the above exercise with this topic. Here’s how it went.
- Why do I want to write a blog?
- Because I want to have a better understanding of the world around me and try to help people along the way.
- (Sometimes it can be tough to pull on two threads at once, so I’ll just focus on one.)
- Why do I want to have a better understanding of the world?
- Because I don’t know everything, and I think knowledge can help me live a better life.
- Why do you think knowledge will help you live a better life?
- I think we’re all supposed to pursue knowledge in some form as humans, and learning more gives us more options.
- Why are you supposed to pursue knowledge?
- I think that’s just part of the human experience.
That last bullet feels like my “because that’s just how it is!” moment. I believe that seeking out more knowledge is central to the human condition. That’s just how I’m wired.
The next time I don’t feel like sitting down to write, I can remind myself that by working on the blog I’m grappling with and expanding my knowledge, which is central to what I believe is a human’s purpose on this Earth.
It makes doing the thing that much easier.
Beyond the Why
Asking yourself why (unfortunately) won’t answer all the questions in your life.
Using “why?” is best saved for exploring why you want to do something specific or what you value.
Other questions aren’t easily answered by “why?”

People might be tempted to ask, “why did a loved one get sick?” or “why do I always feel so low?” We look for logical answers for questions like these, but sometimes, bad things just happen.
A way to reframe these questions might be to use “what?”
What is this injury teaching me? What’s a common denominator when I feel low?
Maybe there are even better questions to ask yourself, but we can’t always get to the root of a big problem with “why?”
Understanding Ourselves
If you find yourself trying to start a new habit but feeling like you’re unable to make any progress, consider exploring the core value associated with that habit.
You might even find that you don’t care as much about the habit as you thought, and you can happily abandon it for a better one.
Asking yourself “why?” can help you reach your core beliefs, which will help you better understand who you are as a person.

“Why?” won’t always be the right question to ask, but it might just help you set off in the right direction.
It can be hard to navigate this human experience, but by digging in on your values, you make it that much easier to be true to yourself.
What’s one of your core beliefs? How did you come to understand it?
If you’ve got a topic (a book, a movie, a song, etc.) that you want me to break down, leave a comment below!