How Overthinkers Can Achieve Their Goals

Source: Engin Akyurt / Unsplash

Many overthinkers are motivated to excel, but face a paradox: Overthinking often slows or even stalls progress by causing muddy thinking and overwhelm. It's aimed at preventing mistakes but overthinking itself becomes a bigger threat to success than mistakes.

To prevent sliding into this pattern, overthinkers need regular reminders, practice, and tools to prompt them to break problems into clear, manageable steps, think logically, and work methodically.

Overthinkers need bounding boxes to prevent them going on tangents of overthinking, engaging in premature optimization, and letting the perfect be the enemy of the good.

Why Breaking Challenges Into Milestones Can Prevent Overthinking

Defining clear milestones is a powerful antidote to overthinking—it prevents overwhelm, scope creep, and premature optimization, while providing steady reinforcement. Checking off each milestone makes progress tangible and motivating.

The Types of Milestones That Can Help Overthinkers

To illustrate how milestones can help an overthinker, let's walk-through a simple challenge. This example comes from a coding class from Stanford University. You won't do the challenge—this is just to demo how milestones help.

random circles

Source: Dr Alice Boyes

The challenge: write code that draws 20 random circles inside a rectangular canvas (a box). All the circles should have the same diameter, but a random color and random position within the rectangle. In other words, each time the code runs, it generates a different picture, like the image shown.

The task could be accomplished by breaking it down into these milestones:

• Draw one circle of the correct size.
• Write a loop that runs 20 times (draws 20 circles. The position doesn't matter. They could be just on top of each other in the same place on the canvas).
• Write a function that places each circle at a random position within the canvas.
• Write a function that makes each circle a random color.

This example shows what milestones look like in practice, but let's clarify the term further.

What Milestones Are and Aren't

Milestones mean different things in different contexts. In this context, milestones don't mean:

• Outcomes you can't control, like when your YouTube channel reaches 100,000 subscribers.
• Habit streaks, where you're just repeating the same behavior.

Milestones can mean those things in other contexts, but here they are self-contained, discrete building blocks that you control and complete step-by-step as you progress toward your larger goal.

Why Milestones Matter for Motivation

We do more of what's rewarded. If you're overthinking, but not making real progress, you're not being rewarded for your efforts. This hurts motivation.

Milestones help fix this. When each milestone is clear and self-contained, it creates a natural opportunity for small wins. That moment of completion reinforces your progress and gives your brain an earned reward, something overthinkers often miss because they're mentally already ten steps ahead.

How to Create Milestones

We've talked about why milestones are helpful and what they are, here's how to get better at creating them:

• Practice with an already familiar task: Take a task you already do regularly and spell out the milestones you already work through each time you do it.
• Try breaking a new task that will take you 30–60 minutes into milestones. Your first milestone should be something you can hit in 5–10 minutes. Don't include more than 4–5 milestones. Refer back to the random circles example for inspiration.
• If you have any interest in coding, the free course I drew the example from (see references) will give you extensive, fast practice working through challenges using milestones. There are many short challenges to practice with. Sometimes the instructions for the challenges provide the milestones for you, to model how to do it, and sometimes you're expected to do it yourself. The course lectures also teach this.

Overthinking Threatens Your Success More Than Mistakes Do

Milestones are the tools you need to overcome this. They solve the problem by creating bounding boxes for your efforts. They stop the endless refinement and give you permission to move forward. You'll experience earned rewards and the progress you crave and deserve. If you're interested in more tools for simplifying your thinking (perfect for over-analyzers), try this guide.

Motivation Essential Reads

Why Trying Harder to Motivate People Doesn’t Work

The Three-Step Path to Optimal Living

Facebook image: PeopleImages.com - Yuri A/Shutterstock