#4: Be Cringe About Your Why

We know what we want and what's getting in our way — month 4 is all about figuring out why we want to do it in the first place.

Be Cringe is a year-long experience centered on showing up more authentically — even when it feels embarrassing. Each month, I share a theme, reflect on how I’m working with it in my own life, and invite subscribers to explore it alongside me. Welcome to Month 4: Be Cringe About Your Why. Below, I’ll share insights from our third month, Be Cringe About Your Blocks, as well as how our fourth month will unfold.

The insights from Month Three are free to read, and the full Be Cringe experience is available for paid subscribers.

You can read about Be Cringe, and learn how to join us, here:

Introducing 'Be Cringe'

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Month 3 Recap: Be Cringe About Your Blocks

I’ll be honest. I did not want …Your Blocks to be the theme for Month 3 when I first created this plan. It felt a bit too deep, too much, too soon. Frankly, I wasn’t in the mood. Surely we can deal with this later, when we’re really warmed up, right?

My reaction was visceral, and this resistance told me everything I needed to know — I need to do this now in order to set the course of the rest of the year. Whatever was coming up for me likely was one of my blocks in action, and starting to tackle it now is how I can ensure I am able to approach the rest of the year as open and honest as I possibly can.

Hopefully, you feel the same. I mean, I did give us two months to warm up, after all. What’s to come can’t unfold the way I know it can if we don’t know what’s holding us back.

I knew the first block I needed to tackle was that reaction — why was I so resistant to going through this exercise, even when I knew it was right? What can I learn about how I resist other situations?

The answer came to me instantly. I don’t like dealing with hard stuff around other people, even those closest to me. I don’t exactly suppress my emotions — on the contrary, I feel them deeply, try to work through them, spend time thinking, ruminating, etc. But I do so alone, privately, and maintain an air of everything being “all good”.

But why?

Again, a few things came up immediately.

Loudly and at the forefront was my history in social situations growing up. I don’t want to say I was an outcast or a black sheep, because I always had some sort of grouping of friends. But I also was often made fun of, bullied, and through those experiences learned to wear a mask.

I am very lucky that my bullying was rarely physical or extreme (except for the one time on a bus ride in 6th grade when a girl¹ slapped me, seemingly for no reason, while everyone was singing Hey, Juliet) and that I largely existed before cyberbullying was a term that was well-known. I wasn’t psychologically tortured, but man, I dealt with a lot of assholes.

It was mostly being excluded on the playground, being made fun of for something I wore, said, or did, etc. It got to the point where it felt like no matter what I did, something would be taken the wrong way and there was no way out of it. It felt like something I was destined to go through, and I felt it would go on forever.

The fear of saying or doing the ‘wrong thing’ is something that lives deep within me.

In my American History class, I raised my hand and asked, “Where did the Boston Massacre take place?”

I assumed it was very obvious that the Boston Massacre took place in, well, Boston, so I didn’t feel I needed to specify that I had actually just come back from a trip to Boston, and I wanted to know precisely where in Boston this historic event took place.

My classmates also thought it was obvious that it took place in Boston, but did not understand that I knew that. Laughter erupted throughout the classroom, and my face turned instantly red.

“No, I mean where,” I tried to interject. “In Boston, but where?” It kept not landing, and the joke kept going.

The words I couldn’t get out were, “Obviously it took place in Boston, you fucking twelve-year-old asshole morons. I want to know the location within the city of Boston where this particular event took place, because I was just there and I am trying to orient my lived experience with the historical one”.

But I couldn’t find those words, and I kept asking variations of “where?” to try to explain myself further. I’m pretty sure this infamous question was referenced in my yearbook.

This is only one example of how the fear of saying the wrong thing started. It illustrates my worry of not looking ‘smart,’ and is one of many origin stories to my belief that I’m bad at spoken communication.

As I kept writing and working through my blocks, dozens of these stories poured out of me from all walks of life. It was deeply uncomfortable to go through, but sitting with it was healing and important. But letting these stories pour out onto the page² was illuminating.

I don’t know how dealing with that type of scrutiny for over a decade would have any other result, to be honest. Of course I keep things close to my heart now. Of course I second-guess the way I show up and how what I’ll do will be perceived. Even as I work through this particular block, I don’t know if I’ll ever move past it.

Other blocks also appeared — blocks around money and not having what other people have (and how I fear I’ll be in the same position with my child), around not being diagnosed with ADHD until I was 29, and how that has deeply impacted how I view my intelligence, my ambition, and my overall ability.

The way I dealt with these experiences was to put on a mask and hide how I was really feeling in an attempt to be less noticed and take up less space. I realize I’ve been wearing it for so long that it started to feel glued to my face. I’m in the process of prying that glue off.

So, I was cringe about my blocks. I faced them head on, and tried to understand as much as possible why these things came up in regard to the things I wanted to do in my life.

Another thing I learned this month is that it’s okay to have something come up and not know what to do with it immediately. I knew this when I picked this theme — this one isn’t going to be wrapped up in a bow in 30 days, and it’s okay to know that something is a block, not be able to really figure out why yet, and take action and push through despite that.

I’ve launched the podcast and quit the job, even though I don’t have all my blocks figured out. Just knowing they’re there allows me to continue to explore and push back as time goes on.

There are always people who are going to have something to say — who are going to see what you’re doing and have a comment. I’ve realized my life isn’t for them, and now that I understand some of the reasons why I gave this group so much power in the past, I’m finding it so much easier to be unapologetic.

Month three was powerful. I’d love to have you join us. And honestly? Even if the full series isn’t for you, I think there’s a lot to be learned from peeling back our own layers and understanding what stops us from reaching our full potential.

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Be Cringe About Your Why

Throughout the first quarter of this year, you’ve shown up and named what you wanted. You’re thinking and taking action, and you’ve reflected on what’s stopping you and your blocks (and why they exist). You’ve started to cast those blocks aside and maybe you’re getting clearer on the things you want.

But maybe you still feel a little disconnected from those wants in the first place. Or, you know you want them but are finding it hard to have real momentum in going after those goals.

It’s time to define your why.