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Security Questions

Last week, I was logging into the human resources portal for my job when I was prompted to reset my password. As I went through the various 2-step authentications, mindlessly confirming my cell phone number and email, it pulled up a previously answered security question:

What was your dream job as a child?


I typed writer as effortlessly as I’d typed my phone number and then moved through the rest of the login process. A moment later I paused at how obviously that had occurred to me—and what a telling gift that was for a couple reasons.

First, specifically to security questions, I am a classic overthinker. When asked my childhood best friend’s name, I immediately begin to wonder if I put just their first name, their full legal name, their nickname with their last name, or some other combination. I no longer pick that question.

Second, regarding dream jobs, this was something every student at my elementary school was asked annually for the school year book. Once I said artist, once I said Dunkin Donuts worker, once I said veterinarian. But the one I said most frequently and from the youngest age was writer. Writer. Writer.

Perhaps it’s a testament to the truest versions of ourselves to be able to, without thinking, confirm something your heart has known for a long time. It is, of course, easy to make excuses, to wonder what the past you would have said, to think about the myriad paths you could have taken.

Ah but again, if you had to answer the dream job question without a moment’s notice or space for reflection, what would you say? And it’s not just the dream job question, which at its core can be hyper-capitalistic and problematic. But other questions we ask ourselves under the guise of security.

Where do I want to live? How do I want to spend my time? Do I enjoy being around my friends? What would I do if I had an entire day with zero responsibilities? Who do I miss? Am I happy with how much time I spend on my phone?

What if we had to answer these as quickly as we’d answer a security question? Have you held enough space this week for listening? Are you making room for the quiet inner work of reflection?

I was talking to a designer last week who made a joke about spending two hours staring at the blank page before beginning. I played along, comparing it to the writing process. But what happens when you don’t have those two hours?

Allow space for staring. For thinking. For nothing. Relentlessly allow your mind to breathe. And then, someday (perhaps when you’re mindlessly answering a security question), you’ll be reminded of who you are at your core… and you’ll know that some things are wildly worth pursuing.

Love always,



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