Climbing up Maslow's hierarchy, we've reached the Esteem level. Today, we're zeroing in on a crucial aspect of this: confidence.

Let’s get started

Earned Confidence

What is confidence?

Confidence is the cornerstone of esteem, this level of Maslow’s hierarchy. Confidence serves as the bridge between our abilities and our sense of self-worth.

This isn’t about bravado or arrogance, but rather a quiet assurance in our capabilities. We’re not talking Dunning-Kruger levels of (stupid) over-confidence.

Instead, valid confidence is born from a cycle of planning, execution, and reflection.

Crudely

• We set out to do a thing.

• We do the thing.

• And then know we’ve done the thing well.

Lack of confidence stems from either not doing the thing (procrastination) or doing the thing well and not giving ourself credit (imposter syndrome).

Overconfidence comes from doing the thing poorly and thinking we’re an absolute champ.

Confidence, in its purest form, is the ability to say "I can handle this" in the face of new challenges, not because we're certain of success, but because we trust in our capacity to learn, adapt, and persevere. We’ve done stuff out of our wheelhouse before and, most of the time, it went pretty well.

Confidence foundations

For entrepreneurs, especially those just starting out, confidence can be elusive. We often downplay our achievements or doubt our abilities. But here's the thing: confidence is a skill, and like any skill, it can be developed.

First up let's use AI to help recognise past achievements and build a baseline of confidence:

You are a supportive and insightful professional coach.

Help me recognise and appreciate my achievements and skills. Ask me questions about my professional and personal accomplishments, overcome challenges, and acquired skills. 

After our discussion, provide a concise summary of my key achievements and capabilities. Frame these as powerful, factual statements that I can use to boost confidence. Ask one question at a time and wait for my response before proceeding.

I’d recommend keeping a copy of the end result saved somewhere. Or, really powerfully, you could print them out.

Having an external reminder of your capabilities can be very useful. Especially when you are feeling a severe lack of confidence. If mantras and the like help you then you can also use the output of the prompt in this way.

Building confidence

Let’s now build on this base foundation.

Confidence isn't static. It grows when we push ourselves out of our comfort zone, realise we’re okay, and then establish a new norm. It's an incremental process.

The first time we do anything it’s scary. Our brains are programmed in that way. We don’t want to risk our ego. We don’t want to make mistakes. We don’t want to look stupid. So doing something new is always hard.

But at the same time our brains are really good at acclimatising. Do something enough times and you’ll get used to it fast. And that expands your boundaries and confidence.

This brings us to our next prompt

You are a strategic goal-setting coach with expertise in personal development. 

Help me define three significant achievements to focus on this year that will push me out of my comfort zone and build my confidence. They can be personal or professional goals.

Ask about my current skills, areas I want to improve, and my long-term aspirations.

Then, for each achievement, break it down into small, manageable steps. The goal is to make each step feel as effortless as possible while still pushing my boundaries.

After our discussion, provide a summary of my three main goals and the step-by-step plan to achieve each. Ask one question at a time and wait for my response before proceeding.

Run this prompt exercise to come up with 3 big scary goals to focus on. They can be personal or professional - building confidence in one area generally leads to confidence in others so don’t sweat the “best” goals here.

I’ve also set the prompt up so that it makes each challenge achievable. Instead of “run a marathon” this will generate a set of steps starting with “walk/run 1000 ft” or something equally achievable to get started. We incrementally push limits.

Repetition

Remember, this is a all an ongoing process. There’s no sudden witch from “not confident” to “confident”. It’s all degrees.

Because of this it’s useful to run this exercise repeatedly. Set a reminder to run the first prompt (assessing your achievements) next year. You’ll by then have new achievements to add to your list. And an ever better sense of self-esteem and confidence.

Confidence isn't about never failing; it's about knowing you can handle whatever comes your way. Hell, if you’ve read my work you’ll know I think failure is great. Failure is the only way to learn anything! It happens - and it’s a good thing.

Confidence is instead about trusting in your ability to learn, adapt, and overcome. It’s the “I’ve got this” feeling when facing a new challenge.

And that attitude? That can be learned. You got this.

Keep prompting,

Kyle