Quit Should-ing on Yourself

Written by David Tran

I recently spent a breezy Wednesday morning at a quaint, colorful brunch restaurant in Sorrento Valley. My friend and I both ordered Nutella Crepe and Eggs Benedict, eager to delve into our breakfasts and into each other’s lives. We conversationally scrolled through one other’s newsfeeds, smiling and expressing “hoorahs” at the highlights while empathetically nodding during the lowlights. A recent college graduate, my friend shared a dilemma that probably took a lot more self-awareness and insight than a brunch could produce. He then asked me, “What should I do?” 

Should. Every time I hear the word “should” when working through life’s biggest issues, I shudder. Why would someone do anything that isn’t being directly driven by their own values, priorities, beliefs, and passions?

I should spend less time doing what I enjoy and more time doing good for the world.

I should go to the gym more.

I should eat healthier.

I should forgive that person.

I should say yes every time someone needs help from me.

I should pick up the phone when my mom calls.

I should ask that person out.

I should choose a career that pays a lot of money.

I should chase my heart’s passion and trust that it’ll all work out.

I should do what he/she/they said.

I should cut social media from my life because it’s distracting me from real relationships.

I should stay together with my significant other because I feel bad for leaving them.

I should do something more interesting and more significant with my life.

I should take time to travel now, because I don’t think I’ll have enough time later with a spouse and kids.

I should learn a new language, it may be useful for my job or important down the road.

I should be in a more amazing job with higher pay, job satisfaction, and better work culture—whatever that means, but I don’t know what that means. I just feel like I should.  

I should have more friends on Facebook—more likes, more wall comments, more posts, and more acknowledgments.

I should be married by now, but I’m not. I shouldn’t be single.

I should devote more time to helping orphans, sharing meals with the homeless or maybe even volunteering at a charity.

I should sign-up for graduate school or take advantage of all my educational opportunities because they’ll be wasted if I don’t act now.

I should make my life look better than it does right now.

I should take on as many internships and jobs as possible to supplement my resume.

I should do ____ so I don’t look like a  ____ to others.

I should, I should, I should. 

At some point in our lives, we’ve all faced the shoulds and shouldn’ts, the dos and don’t dos, but our lives should never be consumed by the polluted gas of “shoulds”. Be it our parents, our closest friends, our professors, our spouses, our future employers or even the girl or guy we meet and fall in love with, our minds are constantly flooded with how we should think, feel, act, and see ourselves. Facebook, Netflix movies, magazine covers, salary.com graphs, and the shiny, pretty things other people have can create an unhealthy and unnecessary bridge between the type of person we want to become and the type of person we think we should become. How often do we find ourselves in a pool of shoulds and supposed-tos, with voices and outside judgments that cripple our imaginations with dreams that others purpose for us, rather than swimming in an ocean of our own dreams?

Meg Jay, author of the The Defining Decade, writes, “Shoulds can masquerade as high standards or lofty goals, but they are not the same. Goals direct us from the inside, but shoulds are paralyzing judgments from the outside. Goals feel like authentic dreams while shoulds feel like oppressive obligations. Shoulds set up a false dichotomy between either meeting an ideal or being a failure, between perfection or settling. The tyranny of the should even pits us against our own best interests.” 

Throw off the shoulds—who we think we should be, and what we think we should be doing. I’d rather people forgive one another because they want to rather than because they feel like they should, because shoulds don’t involve the heart, they only require a behavioral change. Shoulds don’t require us to look into our own hearts and explore the dreams and fears that we long to come face-to-face with.  

What I love about those who live a life not based on shoulds is that they really, truly enjoy their lives. This doesn’t mean commitment or pain are absent. It doesn’t mean that boredom knocks on the door once in a while, but it does mean that emotions—happiness or happen-stance—do not control our desires.  

People who live their true dreams know what they want and need. After my friend asked “What should I do?” I encouraged him to think through his values and priorities, and to make a decision based on what he finds most honoring to his identity. Asking someone else what to do is never a shortcut to doing the hard work of discovering the answer yourself. 

It’s time to let go of the shoulds and shouldn’ts. Take a few minutes to think about your life right now. Are there someone else's shoulds that are driving your behavior? Do you have your own shoulds that are adding unnecessary pressure, guilt or shame?


David Tran is a 2nd year MBA marketing graduate student at the Rady School of Management (UC San Diego), and a social entrepreneur committed to the multi-cultural, underserved City Heights neighborhood.