Why "should" is the most unhelpful word in the dictionary

During lockdown I realised that I subconsciously compare myself to others. A lot.

Mainly comparing myself to friends. Which is unhelpful because my friends are massive overachievers. Fit, financially sound and continually adding accomplishments to their CVs.

But also comparing myself to ex-colleagues. And comparing my business's progress to that of competitors or other founders.

I found myself using the word should a lot.

I should be in better shape. I should have more savings. I should have raised more money. I should eat less pizza. I should drink less wine.

Should, as it turns out, is one of the most unhelpful words in the English dictionary.

Saying we should do something means we've internalised the external voice of others - we've taken other people's opinions as fact. We've created a mindset that pins our happiness to the actions of others, actions which we can't control.

Stepping outside our social comfort zone.

Consider this famous thought experiment.

You wake up tomorrow and every other person on the planet is gone. Your partner. Your parents. Your friends. Everyone.

Obviously this is pretty distressing...but now you're free to get any possession within reach. Anything.

Step 1: You move into a mansion but then you get tired of all the maintenance so you eventually settle with a medium-size house or flat.

Take 2: You grab that SUV you've always dreamed of but then the increase in trips to the gas station causes you to downsize for something more economical.

3rd time lucky? You stock up on Hugo Boss or Chanel and feel glam for a while but then realise they're not very functional and a pain to wash so you revert back to what's comfy.

It's easy to see how so many of our wants and needs are driven by a desire to be perceived in a certain way by those in our immediate social circles.

We want to impress the people we like so we obsess over what we own and what image we project.

More more more!

When we compare ourselves to others, it's easy to believe that we're not fulfilling our potential. We think we could be better and therefore we feel we need to be better and should be better.

But what does better mean? Wealthier, healthier, more productive, more responsibility at work?

An improvement in these things can lead to a happier life. To a point.

The problem is that we don't stop and think why we want an improvement in these areas and when we'll agree to be content.

Instead, we just keep on wanting more.

No matter how much we grow, it's never enough. We always feel inadequate and dissatisfied with our situation.

Less is best.

We don’t know for sure what will make us successful and we can’t pinpoint exactly what makes us happy. But we know with certainty the things that destroy success or happiness.

This simple realisation is fundamental: Knowing what not to do is much more helpful than knowing what to do.

The Greek and Roman philosophers called this approach via negativa.

It means "the negative path" - focusing on removing or reducing things in your life rather than adding more. 

Why this approach? Because when you eliminate the downside, all that’s left is the upside. When you simplify your life in the right way, fewer things to worry about can mean more room for happiness.

The one thing you should do.

Forget your To-do list. Forget the hundreds of things you feel you should be doing, most of which are likely to be externally motivated by comparing yourself to people in your social circle.

Instead, create a Not to-do list.

?Write down the 10-20 internally motivated things that you are certain you don’t want to do. Things that are personal to you and not reliant on someone else doing something.

Why?

Because when you tell yourself "I should do X", you've created a vague, loose, mental commitment to an action that you probably don't fully believe in. Until you do it, if you do it, you'll feel guilty. The happiness that comes from it will be short-lived because the world has moved on and given you some more should do's and should be's.

On the other hand, when you tell yourself "I'm not going to do X", you've quickly eliminated a future scenario and can get back to being in the present. You've wasted little mental energy and you've stayed true to your north star. Having killed the downside of the situation, you're free to be and let the upside happen organically.

It's a subtle difference that might seem like semantics, but when you come to that fork-in-the-road moment each day, it's surprisingly powerful in helping you quickly avoid the things that will de-rail you.

Some of my latest Not to-dos are below (thanks to some refining and feedback from my team at Howamigoing.)

If you do take the time to look inward, I'd suggest printing your Not to-do list out, reading it each morning and reflecting on it each week to see if it can be refined.

Until next month...

In case you missed it...last month I wrote about listening - why it's the foundation of great relationships, why we all suck at it and how to improve. 

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About the author

Julian is the CEO of Howamigoing, a software company that helps people in small businesses get better feedback more often. Howamigoing was recently voted #21 in the UK's Top 100 Startups and in the Top 10 HR Tech Solution Providers in Europe. Julian previously worked in Mergers and Acquisitions at Goldman Sachs and J.P. Morgan, and he served as a fundraising committee member for the Victor Chang Cardiac Research Institute. Julian is an Aussie living in London, passionate about friends, feedback, food, wine, improv, comedy and science. You can connect with him directly here.