#5: Be Cringe About Trying
Be Cringe is a year-long experience centered on showing up more authentically — even when it feels embarrassing, difficult, and yes, cringe. 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 5: Be Cringe About Trying. Yes, we actually get to do something this month!
Below, I’ll share insights from our fourth month, Be Cringe About Your Why, as well as how our fifth month will unfold, for those that want to follow along in real time.
The insights from our previous month 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:
Month 4 Recap: Be Cringe About Your Why
There is a version of this challenge where figuring out your why could’ve been one of the first things I had you do. Figuring out why you want to do something is often the core to success, and can be more illuminating than knowing what it is you want to do, showing up for it, or knowing what’s stopped you in the past.
#4: Be Cringe About Your Why
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
One of my favorite TEDx talks is Simon Sinek’s Start with Why — and I’d reckon many of you have seen this one at least once, too.
I watched it in multiple college classes, at various trainings while I was at Apple, and have had teams I’ve worked on and with watch it as well.
Sinek explains his ‘golden circle’. He takes the angle of business, but this can be applied to us as people too. We all know what we do, some of us know how we do it, and only a few of us really take the time to figure out why.
So when I was designing this challenge, my gut was to have us start with the why — our purpose, our beliefs, our reason for doing. But I also wanted the why to be impactful, and in order to really get to the true core of our why, I knew we needed to define our what and go through what has blocked us in the past (or else we’d have started with why and would’ve probably needed a ‘Be Cringe About your Why Again’ month). You probably started this challenge with a loose idea of your why, anyway. Month 4 is just when we really were able to focus in.
My focus for this month was to get really clear on embarking on a journey of self-employment. As much as I know this is the right path now (my what), and I am experimenting with different ways of going about it (my how), I’ve been struggling to articulate why. I’ve been struggling to figure out what exactly I wanted to do, too, beyond a very loose shape, and I think not settling into my why absolutely contributed to that.
I spent the month reflecting, writing, and figuring out why I wanted to be self-employed. I paid attention to the feelings I wanted to evoke and why, the types of tasks I like doing and why, and why having some more freedom and autonomy around my time is so important.
Once I did that, I had secretly hoped that the perfect career would fall out of the sky. It didn’t, but what I found was much more profound.
I’ve realized that my journey to being self-employed is a bit more nuanced and layered, and that I am close to hitting on something. I don’t know what it is yet, but this month gave me the clarity to visualize what my perfect days look and feel like, how I define success, and to overall really get curious. For a while, every time I’d ask and answer the question why, I’d ask why again.
And through all of that, a few ideas were born. Most notably, I’ve launched a new column on my Substack called All of the Above, which is a space where I’m going to dig into all of the various whats I want to do and how I think I can get there, when it comes to my career. That would not have been possible without understanding my why — it’s also the thread I know I will carry as I work through that column, and keeps me honest as my foggy future unfolds.
Month 5: Be Cringe About Trying
Now that you know why you’re chasing after something (and also — what you want to do, showing up to that, and understanding what may be blocking you), it’s easier to actually try to go after what you want to go after.