Dear Overthinker

I’ve always been an overthinker. Whenever I think about one thing it ends up splitting off into a multitude of other ideas and considerations, all of which end up spiraling around each other, and before long, I’m pondering something only tangentially related to my original thought. It’s a messy process that’s difficult to describe. But on the other hand, it also constructs a vivid, constantly evolving world in my head. 

I don’t know. Maybe it’s just me. I mean, I know I can’t speak for everyone, but I feel like we live the most exciting moments of our lives in our heads. We create enthralling and extensive conversations that are never actually going to take place. We imagine entire relationships with people we’ve barely even spoken to. Our minds paint strikingly beautiful works of art and choreograph dramatic fights to the death. With such rich imaginings constantly filling our heads, it can be depressing how little those thoughts translate to our experiences in the real world. 


When it comes to overthinking, it’s both a blessing and a curse. I never run out of things to think about, but I also talk myself out of a lot of things that I genuinely want to do.  Why won’t I start that conversation with the person I’m interested in? Why won’t I make that joke? Why won’t I send that DM? It’s because I’ve thought about it so long that I’ve convinced myself that I’ll come off as creepy; that no one else will find that joke funny; that I’ll get left on read. 

But that’s just social anxiety, right? It’s not like I’m overthinking things that have nothing to do with anyone else. Oh...Oh, no. I stop myself from writing because I’m worried they won’t be interesting or engaging. I refuse to develop doodles into full drawings because I fear that I won’t be able to do my visions justice. 


Why am I like this? Why do I let the worst-case scenarios dictate what I am willing to do? Why can’t I just do things? Just do it, little wonder this swoosh brand is one the biggest - so much power in three words. 

I miss being a little kid without a care in the world. I miss the creative liberty of expressing my thoughts. I miss being five years old and happily scribbling whatever I was passionate about in crayons on a piece of paper. The excitement of sharing my doodles with my friends (which are mostly incongruent shapes littered with crayon strokes). I want that expressive liberty.  

I imagine traveling back in time to when I was five years old. I grab a blank piece of paper and a pack of crayons. Taking a deep breath, I start to write a letter: 

“Dear Overthinker,” 


I am stuck. What exactly would I tell my older self? What wisdom would I give myself? How would I prepare myself for the rigors of adult life? To be honest, I don’t even think current me has the whole adulting thing down yet. In fact, I might never really get it down. Geez, that’s depressing. Ok, I should focus on what I know. What do I know? Certainly not calculus. This doesn’t make any sense. know…? 

I’m an overthinker. 

I think myself out of the things I want to do. 

I should take those scary spontaneous actions. 

I need to live a little more. 

Hold up! Seems I have just found a strategy; indulging my worst-case scenarios, maybe that might just influence the breakthrough I have so much wanted. 

“Dear Overthinker,

Ask that person on a date. If she/he stands you up, hey, your couch makes good company. 


Dear Overthinker, 

Like and leave those social media comments, every other person knows of your unparalled  stalking ability. 


Dear Overthinker

Slide into that DM. Technically, the blue tick can pass for a valid reply.


Dear Overthinker, 

Write that article. There are billions of people on this planet and your article is the least of their worries.


Dear Overthinker, 

Put out that work of art. No one’s going to hate it more than you already do. 

After what seems like hours of cerebral processing and mental time travel, I am brought back to my reality, still, feebly holding my colored pencil with these two words on a paper “Dear Overthinker”.

I realized my younger self is still me after all; an overthinker. 

Dear Overthinker

… (still overthinking)



Dear Overthinker

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