The Overthinking Trap


Clarity isn’t the starting point. This is.

Hey Reader,

Let me guess: there’s something you’ve been circling for a while.

A decision.

But you haven’t moved because you’re not clear yet.

You're stuck in analysis paralysis because you think you need to figure it all out before you take the first step.

I hate to break it to you, but this is how you stay stuck.

You're never going to think your way to clarity.

I know this because I spent years trying; thinking, is, after all, what I've always done best. I'm also a recovering perfectionist.

This is also something I've seen in the introverts I've coached, who often feel stuck, lost, or unclear about their next steps. I even coached a high-performing introverted executive unable to sleep at night because she was so consumed by her own overthinking.

Here's what's really happening: you're waiting for a level of certainty that doesn't exist before you take action.

And that wait is costing you.

The Overthinking Spiral

As introverts, we're natural overthinkers.

We're more likely to research the options, weigh the pros and cons, make informed decisions. It's served us well in many areas of life.

But when it comes to major life questions:

What should I do next?

What will make me happy?

How do I want to spend my time?

...this approach backfires spectacularly.

Instead of gaining clarity, we spiral deeper into confusion.

We create elaborate mental models of hypothetical futures. We debate endlessly with ourselves about paths we've never actually walked.

Meanwhile, life keeps moving. Opportunities pass by. We stay exactly where we are, waiting for the perfect moment of crystal-clear knowing that never arrives.

What Actually Creates Clarity

Stanford University's Life Design Lab has tracked thousands of people redesigning their lives. The ones who create fulfilling changes don't start with perfect clarity - they start with curiosity and small actions.

They try things. They pay attention to what energises them and what drains them. They gather real data about what it actually feels like to do different kinds of work, live in different places, spend time with different people.

This isn't random experimentation: it's intentional exploration. They're testing hypotheses about what might work for them, then letting the results guide their next steps: micro-experiments.

The Method:

If you're tired of thinking in circles, here's a different approach:

Start with what sparks your curiosity, not what you think you should want. That random interest in pottery? The article about remote work that made you pause? The friend's career that sounds intriguing? These are all potential starting points.

Design tiny tests. Instead of committing to major changes, create small ways to explore. Take a single class in something new. Join a community. Have a conversation with someone already doing the thing.

Pay attention to your energy. After each small experiment, notice: Did this energise, or drain, me? What parts felt natural? What felt forced? Your body often knows before your mind does.

Let one experiment lead to the next. You don't need a master plan, or to make any commitment. You just need to follow the thread of what's working and what isn't.

This approach works perfectly with the Odyssey Plans we were generating a couple of weeks ago.

And, best of all, taking action builds confidence.

It's win:win.

Your Challenge

So this week I challenge you to do one small thing to explore something you're curious about.

Book a class. Have a conversation. Volunteer for an hour. Read a book.

Then pay attention to how it feels. What energises you? What feels off? What do you want to try next?

Don't overthink it, or wait for tomorrow: choose something and take one small action. It's just an experiment to get feedback.

I'd love to hear your results, so bonus points for hitting reply and telling me all about it! 🙃 I read every email I receive.


Life, Unbound

Next week, I'm officially launching my shiny new product, Life Unbound and, as a subscriber, you're being given first dibs!

It's been structured in a way that simplifies the life design process to help you take meaningful action, even if you're currently exhausted or overwhelmed.

Here's what one of the Beta testers had to say:

I'm excited to share it with you here, so please make sure this email is in your primary inbox so that you don't miss it (replying also helps)!

In your corner always,
Sam 💛

Sam Sheppard

Let's connect! You can find me on LinkedIn, Instagram, TikTok and Threads.

P.S. When you're ready these are the ways I can help you:



1. Work directly with me:
I offer a limited number of coaching slots and you can apply for a place here.

2. Get inspiration from how I live, not exist, by reading my
book - this link is for the UK but it's available on Amazon worldwide, just search 'to live not exist'.

P.P.S. If you found this email valuable, please forward it to another introvert who might need to see it.

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