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Inside of an overthinking mind
How I’m working on to break free from the loop
Reading time: 8min
Hi, I'm Nat and I write "Dear Self," documenting the emotional journey of peeling back the layers to become who we are. I share my journey with hopes that it can inspire you to grow more connected, confident, and in love with yourself.

It was August last year when the idea came to my mind: The title of the book I felt like I had to write.
In only a few days, I already had it outlined, revised it with a friend, reached out to other people to gather insights about the process of writing a book.
And then, after a couple of weeks, I wrote the first page of the book.
I shared with a few friends, some came to tears. It was so honest and vulnerable, they told me.
But something was missing, although I had the title, the outline, and the first page, a bunch of insight, ideas, and feedbacks. I still didn’t feel ready to write it.
So, I reached out to some more few people to ask for help and insights. I talked it out multiple times trying to find the red thread that would lead me to start writing the book. I followed all advice.
Someone told me to write a poem about the book. And so I did.
Someone else told me to write a book proposal. And so I did.
Another told me to ask people questions about what they struggled with. And so I did.
And still, I didn’t feel ready.
I let it “marinate” in my mind for a while. A while took almost 10 months. When circumstances around me threw this project back on my face, I decided: OK, it’s time. Let’s do it!
So, I write a newsletter about writing a book.
I talk to more few people.
I write a script and record a video about writing a book.
But, where is the dam book??? When I’m going start to write it?
See, that’s one of my life struggles. I’m an overthinker in recovery.
I can spend infinite amount of time doing work around the work that is not the real work, in avoidance of facing the possibility that maybe I’m not cut out to do the work I’m intended to do (unless I have a deadline for it).
It doesn’t happen every time, but it happens every time I set myself to do something that is really important to me. I want it so bad to get it “right”, that I never get it done in the first place.
Besides that, one of the things I love the most is to create systems & structures. It’s helpful on one side because it’s great for the work I do with others, but it turns out to be a slippery slope for my own projects when I can literally spend hours planning the perfect structure for the project, all the future routines I’m going to engage with, and all the systems to keep me on route, and end up never really using them.
Plansturbation

I saw this a few weeks ago. It felt relatable - a little too much.
Although I’m not plansturbating my life away, I recognize that some ideas take way longer than needed to see the light of the day. I loose momentum and opportunity for fast feedback and iteration. I end up feeling so exhausted of so much thinking and planning that it’s not uncommon I give up on projects mid-way.
Hitting my head on the wall
So, I finally decided to sit down and start writing the book.
Only to discover that the entire idea I’ve been nurturing all along doesn’t work the way I thought it would. I rewrote the first pages again, and again, but at the end, it didn’t make any sense in paper like it did in my imagination. In the real world, the idea didn’t sustain itself.
I enter my office taken over by frustration. I remove every planning post-it on the wall, trowing it on the trash bin with sadness and disappointment in myself. Why did it take me so long to test my ideas???? Now I’m back to point zero again.
Gather insights from the real world
Planning is great, but I what I know to be certain is that growth and learning happens from execution.
As an overthinker in recovery, sometimes I want to have all the steps of the journey planned before I give the first one. I want to be sure that it’s gonna work, and where it’s going to lead me.
But projects, business, or life exist as a complex living system with infinite variables that we don’t control, and have no idea that are in play. The only way to know is to give the first step, receive feedback from it, and see where the next step leads.
Planning, direction, and preparation are great, but they don’t mean anything if there’s execution and iteration (adapting the route from the feedback we get from execution).
The longer we keep ourselves planning the perfect thing, the longer it will take for us to know the real possible next step to take. Which will only add up frustration and feeling of failure, if we end up discovering that we will have to adapt our initial idea.
If you are an overthinker in recovery like me and have a project, an idea, a move to make, I urge you to just do it, and plan as you go. You’ll learn a lot faster, iterate a lot faster, and get to where you want a lot faster.
This is not about rushing things, and having to do anything fast in itself. It’s just about not letting grow ideas grow so big in your head that you end up not doing it because now you’re too scared that it won’t go as you planned.
Jumping from the skydive
I remember 10 years ago, I was visiting my brother in Rio de Janeiro when we decided to do paragliding for the first time. As soon as we decided, we booked it for the next day.
We found the instructor at the meeting point, he drove us to the mountain, we waited in line, we put all the equipment on, he invited us to step onto the platform... and then the clouds blocked the clear sky in front of us.
After multiple people had jumped, on our turn the clouds stopped us from doing it. The instructor told us we had to wait until the sky was clear again. So, we stood there on the edge of a mountain… waiting… 20 min… 40 min… 1 h… 1h30… The more time passed, the more my mind started wandering…
“Should we really be doing this?”
“Is this a sign for not doing it?”
“Is this safe?”
“What if my mom is right, and I’m putting my life in danger?”
The thoughts were just getting worse and worse to the point that I was about to give up and step down the platform when the instructor gave us a sign “It’s time, let’s go NOW, fast!”.
And before I could think twice, I was there up in the air, in the middle of the clouds.
It was one of the best experiences in my life.
The more we wait to execute on an idea, the more we are unlikely to do it.
Don’t let fear take over, just execute on it.
You can always delete the words, stop if it doesn’t feel right, change direction.
In the process of breaking the pattern
Chronicle overthinking can be a result of multiple things in life but so far my research shows it’s rooted in two things:
Anxiety, when the brain tries to solve discomfort or fear by over-preparing and considering all possibilities (specially the worst-case scenarios).
Developmental trauma (childhood experience) when the brain gets in over analysis trying to avoid repeating past experiences or negative feelings.
But either way, or both, it can become a learned pattern of internal dialogue, which means a habitual way that we learn to talk to ourselves in our minds - like narratives, fears, doubts we play on repeat.
Overthinking isn’t just a reaction to a stressful situation, but something we might end up training ourselves to do over time, even without realizing it.
What I observed from my own experience is that when I’m in overthinking mode, I’m anywhere but in the present moment. I’m focused on all possibilities about the future, and all past experiences I want to avoid repeating. Noticing that, has helped me at least to focus on finding ways to connect with the present, and reduce the ping-ponging between past and future.
Some things I noticed helps me overthinking less are:
Developing awareness, and noticing when I’m in the pattern.
Doing activities that grounds me in the present. Like breathing, meditation, or physical activity.
Limit information consumption. I reduced a lot of social media consumption, and just information gathering in general. Excessive consumption turns out to be fuel to an overthinking mind.
Challenge myself to a 48h challenge - whenever I have an idea, I have 48h to start executing it or I let it go.
If you experienced this and know other methods/ways that can be helpful, please share them! I’m very curious to learn.
That’s my reflection for the week, and happy executing to us!
I'd love to hear your thoughts and experiences with on this.
With Love,
Nat
P.S. Beyond these reflections, I help individuals turn their story and lived experience into a brand and business that feels true to who they are, if you’re curious, you can explore more here.