When we're kids, we try our sticky little hands at all sorts of activities and skills and, unsurprisingly, we’re often terrible at it the first time we try. But we try again, and we get a little kick of dopamine when we can see progress, and if we enjoy it (and/or it gets a rewarding response from those around us), we try to recreate the conditions that brought the most reward.

A strange thing happens however when we progress to our older years. Being unskilled at something through lack of experience takes on negative connotations. Even the language we use to describe it (as I have in the first line of the blog); we’re bad at something, we’re not good at it, we’re rubbish at it. To the degree that we fear ridicule from our peers if we’re unskilled at a task, particularly in high school; the ‘Thunderdome’ of our social development.

So how does that translate later in life? Well we might then begin to associate being unskilled at something as a character flaw, or even a moral failing.

“I am bad at cooking therefore I am a bad person.”

The tendency to skip over the fundamental facts of any skill acquisition, in that it takes hours and hours of dedicated practice (Malcolm Gladwell would suggest up to 10,000 hours) to even become competent in a skill, leads us to catastrophise to the worst possible outcome almost immediately.

Here’s an example:

An 11-year-old boy who has never played football in his life, is then put in a situation where that’s part of the curriculum in high school, inevitably is unskilled and ‘plays badly’. He is then judged and ridiculed as being ‘less-than’ by his peers (as 11-year-olds may tend to do, the little savages!).

The boy then feels hurt and embarrassed; shamed by his ineptitude and makes a choice. That choice could be any number of things: internalise that shame and forever suffer negative consequences for any feeling of inadequacy later in life. He could choose to not play football ever again to avoid any further shame or embarrassment. He could even be deceptive and manipulate circumstances to avoid being put in situations that would reveal his lack of skill in a task (this one hits home for me in particular).

He could however recognise that he has never invested any time in that skill, accept that he is inexperienced, and make a much more powerful choice. He can choose to be humble, open-minded, and practice playing football (accepting a perhaps unavoidable dose of high-school ribbing). Or he can choose to accept that he is unskilled in football, but prefers to invest his time in other skills: music, art, writing, martial arts, BMX riding, etc. and be unaffected by shame for his lack of football prowess.

One of the difficulties I’ve faced with Stronghold, which I continue to face on a daily basis, is accepting the fact of being unskilled (or at least ‘less’ skilled) at running a business and all the sub-skills that come with that. This is made even more difficult when you are already “sorta good” at something else.

I’m already skilled at playing musical instruments for the simple fact that I’ve invested a lot of time into doing so. To then take on a new skill that I’m not skilled at engages a wrestling match with the Ego (which, as Ryan Holiday will tell you, is ‘the Enemy’).

So, when it comes to improving the business in which I believe in and have tied to my fate; I’m faced with the same choice as the 11-year-old boy we pictured earlier.

It’s no different really: either 1) learn to play the game humbly and with an open mind, 2) decide that this isn’t the game for me and invest boldly in a different game with the same optimistic attitude, or 3) run away from it and forever live in fear and regret.