I sometimes contextualize confidence as the ability to take action as soon as one conceives it. Lately, it came up in the coaching sessions with a client who contemplated quitting her job. The work here was obviously not about evoking confidence for a task, but about establishing confidence for her options.

We did a deep dive into her values and options – philosophically, financially and every other-ly in between. Her career options included more full-time jobs, part-time gigs and building her own business. It evoked my own amusing of how we derive our confidence and regret.

Funny how confidence & regret works

When I examine my regrets, it’s largely made of the things I didn’t do. 

The conversation I avoided. 

The hand I didn’t hold. 

The project I didn’t start. 

The question I didn’t ask.

The spot I didn’t try for.

The words I didn’t say. 

Treasured memories tend to be things that I did do. Even the tiring, scary and embarrassing things. What’s noteworthy is that almost all of these ‘negative’ experiences made me more confident and secure today; they feel like victories. But the stuff I avoided doing (in order to avoid failure) doesn’t make me feel proud today; they feel like my failures!

Same action, same outcome, different experience

From the present, I look back at the past. I wished that instead of not trying things because of “what might happen”, I tried more things just to see what might happen. Yes, whatever might have happened would likely still have happened, if I made those attempts. But I would probably have very different experiences of them.

Back then, I only had enough awareness to focus on the negative aspects of the possible outcomes. If I focused on how I might benefit from the experiences, I would have learnt a whole lot more. My guess is that I would be a more confident person than I am right now.

Reminds me of what John Gray said:

Confidence grows not when you succeed. Confidence grows when you take a risk & survive.

(if you liked this, here’s a snappy piece on IG, featuring this and other powerful confidence-quotes)

The cost of learning is cheaper the younger we are

Pretty much can’t go any other way.

What might happen – when we’re younger

We make countless and seemingly endless mistakes. We break things and upset people. We might injure ourselves or others. We might lose money. The damages we incur tend to be repairable, either because they are simple, inexpensive or can be taken care of with time, which we have more of, in front of us. We tend to frame this as ‘learning’. 

What might happen – when we’re older

Our communities – and often ourselves – expect us to make little to no mistakes. We are penalized for breaking things and upsetting people. Not performing as expected is described as ‘failing’, because we are assumed to already be ‘learned’. The damages we incur tend to be either irreparable or expensive to repair. We may not have the time to spend on it. 

Why you should act with confidence right now

 At this point, I’m assuming you’ve labeled yourself as either younger or older. If you’re older, you might be feeling some regret, or doing the mental calculations to see if it is indeed too late for that thing you wanted to do. Maybe you should have started 5 years ago.

I invite you to ponder: in just five years more, would it feel even later for you? What might you wish for, if you could time-travel to 5 years ago – back to today?

Do you want to pay less or more for your learning?

Would you want to enjoy the benefits of learning for a longer or shorter duration in your life?

We look back at the shit we did ‘back then’ and call it learning. But today, when we consider our options, we invariably focus on ‘not wanting to fail’.

In a few decades more, might you also look back to today, and call it learning? If so, would you allow yourself to learn today?

Can you grab this opening, and free yourself to act more confidently right now, in the present?