How to go from Overthinking to Expert Thinking
Making the shift is easier than you realize

Overthinking and deep thinking are the exact same skill set, with one key difference. Learn about this small mindset shift to start turning your overthinking energy into more productive thought.
Last week, I stumbled upon a great article by Jano le Roux: Four Signs That Separate Deep Thinkers From Overthinkers
He focuses on deep thinkers, which I would argue are people who have mastered expert thinking. As such, deep thinkers will be a proxy for expert thinkers throughout this article; they are related forms of productive thought.
The main takeaway from his thought-provoking article is this:
While overthinkers are driven by anxiety, deep thinkers are driven by curiosity.
That leaves us with a big question:
How do we shift from an anxiety mindset to a curiosity mindset?
Let’s break this down. Starting with looking into the ways that overthinking is reflective of an anxiety mindset, whereas deep thinking embodies the curiosity mindset.
Differences between overthinkers and deep thinkers
Jano shared four key differences between overthinkers and deep thinkers; I’ve summarised them here:
- Overthinkers get stuck in the details; deep thinkers see big pictures.
- Overthinkers get paralyzed in their thoughts; deep thinkers get sh*t done.
- Overthinkers look for comfort; deep thinkers seek discomfort.
- Overthinkers look for instant gratification; deep thinkers delay their gratification.
You can read his full article to dive deeper into each of these differences.
These four points align closely with my PDF guide of 10 things you’re doing to get in your own way. The items in my list are the overthinker’s territory, too. Therefore, I’d like to use the 10 things list to add a few more points to Jano’s first four above:
- Overthinkers ruminate about what others think of them; deep thinkers wonder what others think about the world and all the interesting things in it.
- Overthinkers overcheck their work, anticipating all the possible scenarios; deep thinkers let things be ‘good enough’ and move on to planning for the best possible outcome.
- Overthinkers hold onto everything…in their heads; deep thinkers delegate so that they can free up headspace.
Before we focus on how to make the mindset shift from the overthinker’s pitfall to the deep thinker’s strength, let’s have a look at what’s already working.
What overthinkers get right
The way that an overthinker gets stuck is sometimes tragic. It is the strength of deep thinking, but applied inefficiently.
Which is to say, overthinkers already have the abilities necessary for a mindset shift. They’re just not applying those skills well. For example…
- Just about every overthinker I’ve met has an incredible ability to focus…on the irrelevant details.
- They also are amazing at analyzing…unhelpful data.
- And at rehearsing…past interactions.
- They can be great at defining what gives them gratification…then guilting themselves out of actually enjoying it.
- And finally, overthinkers are fantastic seekers…of short-term fixes.
But what if they could do something different with all that ability to focus, analyze, practice, define, and seek?
Such as…
- Using the ability to focus on the most important details of any challenge.
- Analyzing meaningful data points.
- Rehearsing the desired outcomes.
- Defining what success looks like and its rewards.
- Seeking out longer-term solutions.
Good news and bad news
If you find yourself identifying with the overthinker’s challenges, I have good news! It is possible to shift your mindset toward the deep thinker’s way of doing things.
The bad news is that this is going to take a bit of change. Specifically, managing the anxiety that draws you inward and turns your strengths against your self.
Turning anxiety into curiosity means…
Here’s the work to be done to move yourself from anxiety-based thinking to curiosity-based thinking. This is akin to going from scarcity mindset to an abundance mindset, if you prefer that framing.
- Shifting your analysis from an obsessively detail-oriented focus (overthinking) into bigger-picture perspectives (deep thinking).
- Moving past procrastination and perfectionism (overthinking) to productivity and flow states (deep thinking).
- Going from overactive self-soothing behaviours (overthinking) to more resilience and greater capacity for growth (deep thinking).
- Not seeking quick fixes to relieve anxiety (overthinking) and heading toward more sustainable solutions with bigger payoffs (deep thinking).
- Stopping rumination about what others might think of you (overthinking) and getting your needs met so that you can start wondering about broader topics (deep thinking).
- Reducing the need to overcheck and anticipate all possible scenarios (overthinking) and developing strategies to create the outcomes you want (deep thinking).
- Not using the mind as a messy storage container for all thought (overthinking) and working on cultivating a managed mind to create an open space for deep work (deep thinking).
There is a lot here to possibly work on. Fortunately, perhaps not every point resonates with you.
Reviewing the list above, what one change would make the most positive impact for you? Start there.
Some small things you can try now
Change is all about small steps and practice over time. Here are a few ways to get started.
If you’re obsessing over the details
If you find yourself often lost in minutia, here’s something you can try before you begin your next task:
Take 5 minutes to do these two things:
1. Describe your definition of done for the task.
2. Then, list the steps required to achieve ‘done’. Do not include anything that doesn’t lead you directly to ‘done’.
By doing these two steps, you increase your likelihood of staying on track and not getting lost in the weeds.
If you’re reeling in rumination
Here’s a tip if you find yourself stuck in rumination about what someone else thinks about you:
Ask yourself if there’s an unmet need you might have in the moment.
- Are you looking for reassurance about something you’ve shared? This could be related a need to feel confident about who you are and how others relate to you.
- Are you feeling a lack of stability in an area of your life? This could relate to a need to feel secure.
- Are you feeling unclear on what it is you should be doing? This might indicate a need for more clarity on a particular topic.
Noticing what you need is a great start toward allowing you to ‘solve the puzzle’ of the ruminations and start thinking beyond it.
If you’re repeatedly checking things you’ve done
If you find yourself overchecking and anticipating all the possible scenarios, here’s a new perspective you can work toward.
First, know that anticipating what’s next is a form of self-defense against an unknown future. The goal here is to build your resilience, so that you don’t need to overcheck or run scenarios; you can handle whatever comes your way.
Take five minutes to write a list of things you can start doing to help you become more resilient, so that you don’t need armour against the unknown.
The things on your list can small, big, unrealistic, obvious, whatever. Generate as many ideas as possible and add to your list as new ideas occur to you. You don’t need to act or take any of them further, but the options are there if you choose to.
Takeaway Thought
Deep thinking is one of many forms of productive thought. The key difference between overthinking and everything else is one of mindset.
The commonalities between all these types of thinkers is the strengths they share.
If you can find ways to harness your mental energy and play to your strengths, you can become an expert thinker in all that you do.
The great news is, you already have the skills you need to make a start.
Kim is a life-long overthinker who has overcome many challenges to turn her mental energy into a super skill for getting things done and feeling great about it. She’s on a mission to help others do the same. Join the expert thinkers who are gaining clarity and focus with weekly insights in the Hold That Thought newsletter.
