When the Past Feels Like Proof

A client came to her session recently with a goal she deeply wanted to reach—sign one new coaching client by the end of the month.

She was clear and committed. She even had the time blocked on her calendar to post, have conversations, and make offers.

But every time she sat down to write, follow up with someone, or make an invitation, she froze.

Not because she didn’t know what to do.
But because her brain was busy whispering:

This didn’t work last month. Why would it be any different now?
You’ve tried this before. You’ve tried putting yourself out there. And it didn’t lead anywhere.
You should’ve figured this out by now.

She wasn’t just doubting the present moment. She was ruminating on her past—and using it as evidence for why this wouldn’t work either.

I knew that voice well—because I’ve heard it plenty of times, especially recently.

For me, it shows up in small, sneaky ways:

When I get excited about a new idea, I feel a clenching in my stomach that says, You’ve tried something like this before and it didn’t turn out great.

Or when I make a decision, instead of moving forward to honor it, I replay every other time I’ve chosen too quickly, didn’t do enough research, or focused on a bad outcome.

It’s the kind of mental looping that feels like you’re being realistic, but really, you’re just building a strong case against yourself.

That’s hindsight bias.

What’s Actually Happening

Hindsight bias is when the past feels like proof of what’s coming.

It convinces you that what happened before is exactly how it will go again.
And it makes the fact that things didn’t work out last time feel like a personal failure you should have definitely seen coming.

But here’s what we miss seeing when hindsight bias is influencing our perspective:

You’re not the same person you were then.
You’ve learned more.
You are bringing different skills, information, or ideas with you now.

When hindsight bias takes over, we forget all of that.
And instead of staying curious about a new outcome or possibility, we get stuck circling the drain.

In that session, I asked my client one simple question:

“What else might be true about your goal of signing a client this month?”

She paused.

And then she said:
I’m actually way more visible now than I was a few months ago.
I’ve followed through on many things I used to avoid.
I can trust myself more to keep going.

That moment didn’t just shift her mindset out of hindsight bias—it gave her back some energy and excitement about a goal that really mattered to her.

Because now she was looking forward instead of backward.

This Week, Try This

If you catch yourself thinking: This always happens… I should’ve known… It won’t work out…

Pause. And ask yourself:

✨ What else could be true?
✨ What might I be learning right now that I couldn’t have known then?
✨ What other outcomes are still possible?

Coaching has taught me to ask better questions—not just of my clients, but of myself.

I want you to use powerful questions to help yourself shift from the limited perspective that hindsight bias can trap us in to something more expansive and possibility-focused.

If this feels familiar—if you’ve got a goal you care about but keep talking yourself out of it with “evidence” from the past—I want to invite you to join me for next week’s Community Coaching Call.

Click here to register for this free monthly coaching call.

Bring the story your brain keeps looping through. Or a decision that you keep second-guessing. Let’s explore other possibilities and find what else might be true.

It’s a powerful way to experience coaching in real time and reconnect with the part of you that still wants to move forward.