Should Is A Terrible Word

I’m not sure who taught me this originally. As with all things I can’t source back, I assume it was my awesome and supportive parents who unconditionally loved and encouraged my wacky and zany child self to develop into this effusive and certain blogger (?) or whatever I am now.

Anyway, something I learned growing up at our house was that:

should is a terrible word.

We should not be in the habit of telling anyone what they should or shouldn’t do. :)  It’s really rude almost 100% of the time when using the word should. You sound hypercritical using it in common vernacular. You (almost always) sound as if you know something that the other person does not and you are trying to enlighten the path for him/her. Even in very specific instruction - i.e. yoga or dance instruction - where there is a commonly agreed upon placement of the parts of the body. “Right elbow to the outside of left knee to twist” -- this can (and should!) be said without a twang of ‘should.’ Should is ableist in this context: it implies one way of doing something. Should is limited and finite; it doesn't leave room for possibility. 

Even if you’re speaking to yourself. Think of the internal dialogue: “I should stop procrastinating and go to the grocery store.” Be kinder to yourself. How about something like: “If I want to eat a healthy meal for dinner tonight, I will go to the grocery store in the next 20 minutes.”

When working with start-ups and founders, I resist the urge to use the word. No matter what I think they should or should not be doing, I try to get them to just talk out their reasoning and logic for making their decisions.  I tell them how I learned something - how I got to a conclusion -- but not what they should do. Some of the best business (and otherwise!) decisions come not from a place of should but from a place of if. Less lacking, more possibility. Less grasping, more optionality.  

By the by, I just looked up what should means -- here it is:

Yeah, fuck should. 


Nonetheless, I like to sit around and think of business ‘should’s’ for big companies. Because it’s fun to dream with limitless potential and with a very wide aperture about what could happen in a free and open world.

Here are some of my shoulds -- let me know yours!! Respond below or Tweet me!

Start ups that Uber Should Acquire

Bird, Lime, etc.

Postmates, Grubhub/Seamless,  AND the top 5 - 10 restaurant chains in each city (byChloe, Sweetgreen, Chipotle, etc.)

Local Messenger Services in cities

Tuktuk’s and Pedicabs Everywhere

Companies that Facebook Should Acquire

All the media companies - starting with the big ones

Production Studios

Sponsorship Model for Talent

Partnerships that Twitter Should Do

News Companies - LOCAL, LOCAL, LOCAL

PR Firms  - breaking news should always be on Twitter - ‘real time verification’

Bloomberg + any other live live financial news

Sports - any other live live sports news

Technologies that Amazon Should Deploy

Basket Technology for crowd-sourced pricing and  Best-Of lists

Those are my 'should's' in today's business landscape -- what are yours?!