Katy Montgomery

Katy currently serves as the Global Director of the Career Development Centre at INSEAD where she manages career services professionals across three campuses: Abu Dhabi, Fontainebleau, and Singapore. Katy previously served as the Associate Dean for Student Development at the Johns Hopkins Carey Business School.

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All the Woulda-Coulda-Shouldas

Layin’ in the sun,

Talkin’ ’bout the things

They woulda coulda shoulda done…

But those Woulda-Coulda-Shouldas

All ran away and hid

From one little Did.

By Shel Silverstein

Shel Silverstein, the famous poet and author of beloved children’s books The Giving Tree and Where the Sidewalk Ends, included this poem in his 1996 book Falling Up. Although the book was meant for children (suggested age range 6-8 years), the message is relevant to graduate students, adults, and business people. It is easy to procrastinate especially when it comes to difficult, uncomfortable, and tedious tasks. For a number of job seekers writing a cover letter is agony. Asking a stranger for an information interview is awkward. And, let’s not forget the dreaded salary negotiation. Shel Silverstein knew that the “Woulda-Coulda-Shouldas” could eat you alive. Make you anxious. And he also knew the simple solution—just doing what you dread most can erase a case of “Woulda-Coulda-Shouldas.” What are you avoiding? How can you get to the “one little did?”

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