The Tax of Never Feeling Good Enough
The Hidden Work of Growth #3: Discover how self-doubt distorts your judgement and how to build self-trust through practice.
By Elina ·
It wasn’t that difficult. I was lucky. I could have done better.
Somehow, the achievement never quite makes it into your sense of what you’re capable of.
And then you look at other people.
There’s that guy with a good title, who’s tall and sporty and never seems to struggle to find the right words. Or the woman at work who challenges people openly, makes friends easily and seems to have an endless supply of energy.
You look at them and think: Of course, they believe in themselves. Look at them. They don’t have the doubts I have.
But what if you could hear the conversation happening in their heads? I know few people who look exactly like that from the outside and struggle with the same doubts.
David was one of those people. Maybe you are one of these people too?
He worked for a well-known company, ran marathons and had that calm, collected demeanour that makes you assume someone knows what they’re doing.
Yet his achievements didn’t seem to translate into a stable belief in himself. And the more he questioned his worth, the harder it became to take the steps he wanted to take.
This is the tax of never feeling good enough. You can spend years building your skills and still struggle to use them fully because you don’t quite trust the person who has developed them.
In Capability Practice, we work with these patterns by starting with a real professional challenge, understanding what gets in the way, and practising new ways of responding. Sometimes, the next step in your professional growth isn’t about learning something new. It’s about changing how you relate to what you already know and can do.
The problem isn’t always a lack of positive evidence
When David and I started working together, he was navigating uncertainty about his next chapter. He had ideas, experience and ambitions, but he didn’t feel he had the internal confidence to move forward as he wanted.
Initially, he expected coaching to help him clarify what to do next and identify practical steps. What emerged was a deeper question: why was it so difficult for him to trust himself?
We began to notice a pattern in how he interpreted feedback.
Positive feedback was easy to dismiss. An achievement could be explained away as luck or as something that wasn’t particularly difficult. A strength could be acknowledged and immediately followed by a “yes, but”.
Negative feedback, on the other hand, was much harder to let go of. If 99 people told him he was doing well and one person criticised him, he knew which opinion he was likely to remember.
Think about that for a moment.
If the opinions of others mattered so much, why did the positive ones have so little effect?
Perhaps the problem wasn’t the feedback itself. Perhaps it was the process through which he interpreted it.
We started to explore that process.
The box of tangled wires
I asked David to imagine what happened between receiving feedback and forming a judgement about himself.
He came up with a metaphor: a box full of tangled wires.
Every piece of feedback went into the box. Somewhere inside, it was processed, interpreted and connected to other things. But the system seemed to have its own rules. Positive feedback rarely came out the other side intact. Negative feedback, however, seemed to find its way straight into his sense of self.
The metaphor was useful because it gave us something to work with.
Instead of treating I’m not good enough as a fact, we could begin to examine how that conclusion was being produced.
What happened when someone praised him? What did he tell himself? What standards was he using to judge himself?
And why did he seem to need so much evidence that he was capable, while simultaneously finding reasons to dismiss the evidence he already had?
We could explore where some of these patterns might have come from. Perhaps they had been shaped by expectations, role models or messages absorbed much earlier in life. Perhaps being hard on himself had become a familiar way of making sure he kept improving.
But understanding the origins of a pattern is only part of the work.
In coaching, we don’t need to resolve someone’s entire personal history to start changing how they approach a professional challenge today. Therapy may be the right place to explore deeper emotional wounds or experiences that need healing. Coaching offers a different route: understanding how a pattern operates in the present, deciding what you want to change, and developing new ways of responding in real situations.
With Dave, one question became particularly important: Who gets to decide what his achievements say about him?
He had been treating other people’s opinions as powerful evidence of his worth. Yet he was also the one deciding which opinions to believe and which to dismiss.
He wasn’t simply at the mercy of other people’s judgements. There was an internal process giving some of those judgements’ authority over him.
The work was to understand that process, develop a more balanced way of evaluating himself, and strengthen his ability to respond to himself with greater understanding rather than automatic criticism.
Building self-trust through practice
Understanding the pattern didn’t make it disappear overnight.
David was still navigating uncertainty, making difficult decisions and taking steps that exposed him to the possibility of rejection. There was practical work to do, conversations to have and new situations to learn from.
When we reflected on the work, David described a shift towards greater self-reliance and a stronger internal belief system. He felt more capable, less dependent on other people’s approval and more able to recognise the positive things he had going for him.
He called the capability he had been developing self-trust. It was still a work in progress.
If you recognise yourself in David, perhaps you don’t need another list of reasons to believe in yourself.
Perhaps you need to understand why the evidence you already have isn’t changing how you see yourself and learn to trust your judgement in the moments when it matters.
You don’t have to wait until you feel completely confident to start acting differently. You can build self-trust through the way you act, reflect and learn.
If self-doubt is getting in the way of your next professional step, explore Capability Practice or start with the free Capability Vector to identify the capabilities that may help you move forward.
This story is a composite portrait inspired by several people I have worked with. Names and identifying details have been changed to protect confidentiality.
Originally published on Substack.