“Oh Right… We Were in the Pit of Despair” (And Why That’s Actually Progress)

You walk into your therapist’s office (or log onto Zoom), coffee in hand, ready to get started.They smile and ask, “So, where did we leave off last week?”

You think for a second… and suddenly remember: Oh right. We were knee-deep in my emotional baggage, unpacking the heaviest suitcase.

Cue the meme-worthy moment: “Ah yes… In The Pit of Despair.”

Why the Pit Shows Up in Therapy

Therapy isn’t just small talk and surface-level check-ins — it’s a process of digging into the real, layered, sticky stuff that keeps showing up in your life. That often means returning to certain themes week after week.

And here’s the thing: that’s not because you’re “stuck” or “failing.”It’s because healing is rarely a one-and-done conversation.

Big themes in therapy — grief, trauma, self-worth, trust, relationships — are like knots in a rope. You don’t untangle them in one pull. You loosen them, revisit them, and gradually make space for the rope to straighten out.

What “Picking Up Where You Left Off” Really Means

When you’re back in the Pit, it’s tempting to think you’re just rehashing the same thing over and over. But often, you’re actually:

• Looking at it from a slightly different angle than last time.

• Bringing new insights or coping skills you didn’t have before.

• Testing how your old triggers feel now that you’ve been practicing change.

In other words, the Pit might look the same… but you’re not the same person climbing into it.

The Pit of Despair vs. The Work of Repair

Yes, the Pit can feel dark and uncomfortable. But that’s also where repair happens. By coming back to the hard stuff, you’re:

• Processing instead of avoiding

• Integrating your experiences into your story in a healthier way

• Building tolerance for emotions that used to overwhelm you

• Strengthening trust in yourself and your ability to cope

The goal isn’t to stay in the Pit forever — it’s to give yourself the tools and understanding you need so it eventually becomes a gentle dip instead of a freefall.

Making Your Return Trips to the Pit Easier

1. Start sessions with a “temperature check.”Share how you’re feeling that day before diving back in. This can help set a pace that feels manageable.

2. Ask for grounding moments.You can tell your therapist you need to slow down, take a breath, or end on a lighter note.

3. Track your progress.Keep a journal of key takeaways after each session. It’s easier to see how far you’ve come when you have a record.

4. Balance depth with rest.The Pit is important, but so is climbing out for air. Let your life include joy, connection, and simple pleasures in between sessions.

The Bigger Picture

The Pit of Despair is more than a meme-worthy moment — it’s a reminder that therapy isn’t about avoiding the hard stuff, it’s about building the capacity to face it without losing yourself in it.

Every time you go back, you’re proving to yourself that you can.And every time you come out, you’re a little stronger, a little clearer, and a little more you.

So yes — when your therapist says, “Where were we?” and you think, “Right… the Pit,” know that you’re not regressing. You’re doing some of the most important work of your life.