How Jack Dorsey’s ‘Acts of Inconvenience’ Built a Twitter Empire

Convenience is the quintessence of societal progress. The more tasks we can outsource – to computers, machines, or other people – the better our standard of living.

What if in our infinite search for ease, we are unknowingly foregoing an essential element to living a rich life: our need to feel inconvenienced from time to time.

The reason is because inconvenience leads to problem-solving. This involves identifying threats and opportunities in our environment and devising strategies to exert control over them. Problem-solving allows us to put into practice cognitive systems we’ve inherited from our ancestors and which need to be stimulated.

But, as creatures of comfort, if the opportunities are too easy to come by, and the threats are all but eradicated, what’s left for us to chew on? 

One solution is to intentionally inconvenience yourself.  

Jack Dorsey lives a life of intentional inconvenience. He starts his day with a glass of salt water and lemon, eats only one meal a day (dinner), and dabbles in 3-day water fasts. As co-founder and ex-CEO of Twitter, his inconvenience turned out to be pretty convenient.

Here’s why you should do it too, according to science.

Challenge + Skill = Flow

When a challenge is too easy, we get bored. When it’s too difficult, we get frustrated. When it’s just right, we enter a state that psychologist Mihaly Csikszentmihalyi calls Flow.

A life of convenience can get boring. It lacks the necessary psychological immersion we need to adequately stimulate our brain’s reward centres

Introducing intentional inconveniences (like fasting, or sitting in silence, or always taking the stairs) means curating our life’s challenges in ways that meet, and lightly push, our skill level.

The result? We become better at regulating our emotions, more mindfully engaged with our lives, and ever-closer to the highest version of ourselves.

Failing upwards

Convenience means limiting the number of steps there are between Point A and Point B. Inconvenience is the opposite. That’s not only burdensome, but when we introduce more steps into a process, we also increase our risk of failure. And we don’t like to fail. 

That’s okay – after all, our ancestors’ risk aversion is the reason we’re all here today. 

But there are psychological benefits that come with intentional failure. 

When we fail, we become fearless. It’s when our creative problem-solving skills shine, what develops our resilient coping skills, and how we become more empathetic towards others around us.

The result? We become self-confident in our ability to handle anything that may come our way, and thus feel much more in control of our lives.

Make meaning from aversive experiences

When fasting, Dorsey says that time feels slower. 

This makes sense: with fewer hours taken up by preparing and consuming meals, there’s a lot more time left to go around. 

To some, this might sound nerve-wracking. Fewer distractions means having to sit with your thoughts, which can become an uncomfortable, anxiety-inducing activity.

But we need these kinds of inconveniences. They force us to reckon with who we are and who we want to be. And because our human nature is necessarily oriented towards meaning-making, engaging in these meaning-making inconveniences means we take challenges and turn them into intellectual sharpness, emotional intelligence, clearer goals, and a life lived deliberately.

AKA how you build a tech empire.

The opinions expressed here by columnists are their own, not those of

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