Overthinking Decisions? Why Good Choices Still Go Wrong (and how to stop punishing yourself)

You replay it.
You analyse it from every angle.
You wonder if one different choice would have changed everything.

If you have been stuck in decision regret, here is a more accurate way to understand what happened.

The reality most people miss about decisions

Every decision is made under conditions of uncertainty.

You never have:

complete information
full control over outcomes
perfect foresight

What you do have is:

your current knowledge
your emotional state
your environment
your available resources

So when you made that decision, it was not random.
It was the best possible choice within your context at that time.

A simple way to understand this: The investment analogy

Think of decision-making like investing in the stock market.

You:

research
take advice
analyse risks
choose carefully

And still… markets crash.

Not because you were careless.
But because there are external variables you cannot control.

The same applies to life decisions.

Sometimes things go wrong because:

circumstances change
people behave unpredictably
new information emerges
external factors interfere

This does not automatically mean you made a bad decision.

Why hindsight feels so convincing

After something goes wrong, your brain creates a powerful illusion:

“I should have known.”

This is called hindsight bias.

In reality:

you are judging a past decision
using information you only have now

Of course it looks obvious after the outcome.

But at the moment of choosing, that clarity did not exist.

The real problem is not your decision

It is how you evaluate it afterwards.

When you say:

“I made a wrong choice”
“I should have done better”

What you are actually doing is:

removing context
ignoring uncertainty
expecting perfection

This creates:

self-doubt
overthinking loops
fear of future decisions

A healthier way to reframe your past decisions

Instead of asking:

❌ “Was this the right or wrong decision?”

Ask:

✅ “Was this the best decision I could make with what I knew then?”

This shifts you from:

judgement → understanding
blame → self-compassion
regret → learning

What to do when a decision doesn’t work out

Here is a grounded approach you can use:

1. Reconstruct your past context

Write down:

What did I know at that time?
What options did I realistically have?
What pressures or constraints existed?

This helps your brain return to the actual decision environment.

2. Separate outcome from decision quality

A good decision can still lead to a poor outcome.

Ask:

Was my process thoughtful?
Did I act with the information I had?

If yes, the decision was sound, even if the result was not.

3. Identify what was outside your control

List external factors that influenced the outcome.

This reduces:

false responsibility
unnecessary guilt

4. Extract learning, not blame

Instead of:

“I failed”

Shift to:

“What would I do differently next time?”

5. Practise self-compassion

You are not meant to predict the future perfectly.

Growth comes from:

honest decisions
not perfect ones

A simple expressive arts reflection activity

Since you work visually and emotionally, try this:

“Control vs No Control” Drawing

What you need:

Paper
Black pen or marker
Water or a brush

Steps:

Draw a clean line across the page (your “plan”)
Label it: control
Add water or ink and let it spread naturally
Label the distortion: no control

Reflect:

What part of your life feels like this right now?
What are you trying to control that may not be controllable?

This creates a felt understanding, not just a logical one.

Recommended tools to support reflection and grounding

You can deepen this process with simple, tactile tools:

🖊️ Journals for reflection

Guided self-reflection journals
Blank sketch journals for expressive writing and drawing

🎨 Art materials

Watercolour sets (for fluid, uncontrollable expression)
Brush pens or ink pens
Mixed media sketchbooks

🧘 Grounding tools

These are not just supplies.
They help externalise thoughts and reduce cognitive overload.

Watch the visual version of this insight

If you want to see this idea unfold through an art metaphor, watch the Short here:

It visually demonstrates how control and unpredictability interact in decision-making.

Final thought

You are not meant to make perfect decisions.

You are meant to make honest decisions with limited information.

And then learn, adjust, and continue.

💬 Before you go

Save this for the next time you start doubting your past decisions.

And if you feel comfortable:

What is one decision you have been hard on yourself about?