As I wrote this newsletter draft (which was initially on time optimization), I felt guilty.

I should be in my office, standing straight, sipping warm tea whilst writing.

I should be in a socially-agreed decent setup for work. I’m not. I’m at the beach, scribbling this edition on a notebook like it’s 1997.

Handwriting is slower than typing, then I have to write on the computer, and decipher my own words (see exhibit A). This is not exactly efficient. And frankly, what kind of driven entrepreneur spends a meeting-free afternoon at the beach instead of the office?

As I become aware of my guilt, and these inner chats, I realize that ‘should’ has been the main theme of my week.

It came up in various coaching and mentoring sessions, my good friend Cordu forwarded a newsletter about it, and my mind is currently exploding with shoulds and shouldn’t.

So I should want to make it this week’s theme.

Let’s dive in!

Over-thinkers are in the business of manufacturing problems

By shoulding ourselves we create problems in series. 

We refuse the way we, situations, or our desires are. It generates tensions, usually with superficial (yet feels real) pressure and guilt.

Why?

Tension #1 - Society says it should be hard

How dare we have fun when we want to be successful? Playtime, since our youngest age, has been classified as frivolous. It was limited, scheduled, allowed if you’re done with your tasks time. We bring this into adulthood.

You’re likely at the stage of your life, where you know this is not always true, and most importantly you don’t want to live this way. You want to thrive, and have fun and be relaxed along the way.

Yet when you make it fun and easy, or if you take a deserved break you feel guilty (so do I).

Tension #2 - We want ease, but difficult means success

Anyone successful in a specific area will tell you: difficulties will pop in on your journey.

Because we associate being successful with grinding, our mind uses a shortcut, which turns into a maze.

The unconscious logic: success happens after overcoming difficulty/ solving challenges ➡️ let’s create challenges ➡️ when I overcome them, I’ll be successful.

The result: the mind becomes a problem manufacturer. It creates shoulds, to add in a level of difficulty and pressure.

The price to pay: If we listen to the shoulds, we create solutions that don’t make sense. A weird, unsatisfying in-between compromising what we want, and/ or our goal.

Tension #3 - Reaching the goal can feel wrong

I left Airbnb, and corporate in general to run a business I love (writing and coaching on mindset). But also, and mostly, to build a certain lifestyle. One where I’m relaxed and get to work from the beach without an angry boss breathing down my neck.

I live my vision as I write from the beach. I am also delivering the newsletter (you’re reading it right now), plus I’m tanned. This should feel like a win.

Yet, I turn into the angry boss. I focus on only one tiny aspect of the goal (running a business), and how other people say it should be done. I’m disregarding the overall goals (business + lifestyle + mindset + written newsletter).

When you ignore the shoulds to follow what you want, it feels wrong. That can bring a controlling mindset, that zooms in on one details and forgets the rest.

It’s actually not wrong, it’s just new.

New feels weird, uncomfortable and generates doubts, which can generates more shoulds.

Tension #4 - We’re afraid of being lazy

Remember Ofman’s cadrant from the edition on perfectionism?

Driven professionals are ‘allergic’ to passive, lazy people. We’d rather be over-demanding than passive. Being balanced feels scary, we may end up on the lazy side of the spectrum (☠️).

How do we bring in balance? We challenge the ‘shoulds’.

What if I get too relaxed or passive? Chances are, you won’t. But just in case, aiming for balance requires self-trust, self-awareness, and a constant internal check-in. Take into account the task, your current mindset, your physical energy, and your overall goals. Challenge your shoulds accordingly.

One nudge for you

Next time you say I should…

• Replace should with want
  If you don’t want to do it, don’t should yourself.
  If you want to, then replace I should with I want. It will change the energy with which you accomplish it.
  Remember sometimes we don’t feel like doing it but we still want to (go to the gym for instance).

• Remind yourself of your goals
  Zoom out. Challenge how the should vs your way serves your broader goals.

• Notice how much space you free up when you stop guilting your way into shoulds. 

Thank you for reading, I shall go for a swim now!

Happy Friday,

O.

Was this forwarded to you? Read my previous post and subscribe here.

Too many shoulds in your head and want support? Let’s explore coaching together.

Curious? Meet Cordu (she has an awesome marketing newsletter) and, or read the newsletter on should that she sent the me.