The Problem With Asking “What Could I Have Done Differently?”

“What could I have done differently?” is a classic coaching question. It can give rise to awareness, encourage learning, and connect with the fact that other options and possibilities exist. But it can also be a double-edged sword, especially for people with a tendency to take too much responsibility for things that aren’t ours.

Maybe you look back at an event and instinctively think, “that could have gone better”. Even if it went to plan. Perhaps you experience difficulties with another person and ask yourself, “What am I doing to cause their behaviour?”

Taking over-responsibility for things that aren’t ours can be draining and disempowering. And while this question can often be helpful, it needs framing in a way that doesn’t create frustration and resentment.

When it lacks openness and playful curiosity, “What could I have done differently?” can be a source of judgement, criticism, and blame. We need to know how we’re holding it, what we’re using it for, and how it lands for others when we ask it.

In my coaching, I have become more aware of how judgemental it can feel if asked in the wrong manner and moment.

The Problem With Asking "What Could I Have Done Differently?" Jigsaw Pieces

Deep Processing and Threat Elimination

A characteristic of Sensory Processing Sensitivity is the pause to scan for potential threats, absorb lots of environmental information, and process deeply before choosing the right action to take. Much of this happens below the surface.

On the one hand, what we “ought to do differently” might implicitly underpin this process. But on the other hand, if we ask it explicitly, the conclusion might be, “The fact you’re asking tells me I SHOULD have done that differently – I didn’t do it right”. And this can leave us in limbo without a concrete understanding of what went wrong.

A Recipe For Self-Doubt

It’s not that we shouldn’t ask that question. Instead, we need to ask it gently and at the right time.

A friend reflected on the considerable self-doubt they experience when sharing their creations with others. We traced it back to life with a well-meaning parent whose training as a teacher left an unexpected red mark next to every endeavour. The routine was to ask, “What could you do to improve this next time?” after almost any activity. It applied to creative projects, household chores, and social interactions.

It wasn’t intended as criticism, but it was internalised as such.

Rather than encouraging a steady growth of competence and confidence, this question eroded the latter. It impacted the self-belief needed to explore and develop the necessary spirit of freedom and playful curiosity that underpins learning. The new belief became, “I’m not yet good enough, and I need to get better to be acceptable”. Without any anchored sense of what good enough would ever feel like. It set coordinates for an imagined destination, forever just out of reach.

This type of unanchored self-doubt can emerge from many places. Maybe you recognise it as part of your story too (or you can think of someone for whom this is a perpetual message they tell themselves).

If I Could Do It Again, What Would I Do Differently?

Until a couple of years ago, this question was one of my daily journal prompts. I would reflect on the previous day and consider things I could have done differently to make them better. The intention was to raise awareness and avoid unnecessarily repeating unhelpful actions.

One morning, I answered it with the word “nothing”. It felt good. Freeing. Even a little rebellious. “I am satisfied. No regrets. I wouldn’t have done anything differently”, I continued.

It dawned on me that this question had contributed to a feeling I didn’t want. And while it was meant to be a helpful awareness-raising prompt, I noticed that it put me in a state of internal disconnection. I no longer wanted to start each day bathing in regret. So I changed the question and asked, “What was my favourite thing about yesterday?”

A harder one to answer. But it became a doorway to a world of fascinating and farther-reaching insight. Strangely, if there are things I would do differently next time, they have space to emerge with this question too. Except they arrive as possibilities rather than criticisms.

  • “What did you enjoy about that?”
  • “What surprised you?”
  • “What will you be taking with you from this experience?”

We are naturally drawn to notice negative things to help us mitigate threats and dangers. But the more we focus on them, the more we see life in light of them. Rather than solving problems, we might end up attuned to seeing more and more of them.

Over-Responsibility for Other People’s Feelings, Reactions, and Thoughts

The other issue with asking ourselves questions like “What could I have done differently?” emerges when we take over-responsibility for the well-being and happiness of other people. This can lead us to focus on their reactions, emotions, and behaviours as outcomes that we are responsible for. The question implies that something we did or didn’t do is why they acted a certain way.

Our frame might ask, “What could I have done differently to stop them from responding how they did?” Or “What could I have done so they remain calm?” And even, “What could I have done to make them like me more?”

Taking over-responsibility is disempowering and draining because it ties our sense of well-being to things we have no control over. And it takes away the other person’s capacity and accountability for their choices.

I can’t make you feel anything, and you can’t make me feel anything. And yet we often talk like that’s how things work.

While it makes sense on the surface (and we say it all the time), “they made me feel angry” is not true. I feel what I feel because of the story I tell myself about a situation. It’s true the other way around, too, so we can’t ask what we could have done differently to make someone happy or to like us more.

This is discussed in The Courage to be Disliked, which explores the Adlerian notion that how someone feels about and toward us and what we do is not ours to worry about. We interfere in one another’s “life tasks”; we invite suffering. Our thoughts and judgements (sometimes described as feelings) are responses we choose to hold or let go of.

Pain vs Suffering

It is said that pain is inevitable, whereas suffering is a choice. In other words, we will react emotionally to people, things, and comments. But what we do with initial feeling gives rise to suffering (holding onto the story we tell ourselves about the pain).

“What could I have done differently?” This is a question that can help us process and let go. Or it can invite “suffering” by opening the doorway to thought baggage we lug around as a story we tell ourselves.

If something doesn’t go to plan, we might experience the pain of disappointment, sadness, anger etc. That’s natural. We can process that emotion along with the situation and let go, recognising that what’s done is now done. But if we take over-responsibility for what happened, we might ruminate (fall into persistent thought loops) about how we caused the outcome. Guilt turns into shame, which replaces the story of something that happened with a story about who we are.

Anchoring in a Shame Spiral

When we find ourselves in these shame spirals, questions can help re-anchor us in a more objective harbour. Here are some examples you are welcome to play with and adapt.

The Cue (i.e. a situation, interaction, experience etc.)

  • What happened? (non-judgemental observation)
  • What story am I hearing/feeling within me about what happened?
  • What feelings are coming up for me as I think about this story?

The Connection

  • What did I hope or expect to happen?
  • What made this meaningful for me?
  • What surprised me about how the situation turned out?

The Shift

  • If I encountered this event again, what wouldn’t I change about my approach?
  • If something similar happens again, what story would I love to be telling myself afterwards?
  • What am I ready to let go?

If any of this resonates and you would like to develop a gentler approach to self-awareness and learning, I’d love to chat. Pick The Lock sessions are a great way to begin exploring what’s on your mind. Learn more here.

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