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My Letter to Expectations

3 min
Essays  ✺  Letters to

Dear Expectations, Stop shoulding on me!

Dear Expectations,

Stop shoulding on me!

I am doing the best that I can. And I want you to see that I am enough.

Yes, I get it. There are a lot of things I should be doing.

I should be already promoted at some prestigious muckety muck firm. I should already have found my soulmate and be getting married to them. I should have enough savings to buy a house. I should have rock-solid abs. I should have flawless tan skin from my stress-free life. I should be getting amazing sleep.

Expectations, you keep shaking the soda can so much and are adding too much pressure to the pop. I’m gonna blow!

I’m not here on this planet to please these stories that you are brainwashed to believe are the only way. I know these pressurized thoughts and goals are not created by all your own doing. They’ve been handed down from culture, society, and comparisons. They creep in through a backdoor without your permission masked in the word “should”. Just because they were put onto your plate and then transferred onto mine does not mean they need to be internalized as my responsibility to please.

I am me, and I have my own unique path that I am venturing down.

You, Expectations, are the reason I had my quarter-life crisis and decided to rebel and pick up my life and move to Hawaii in the first place. I realize now there are many other ways than the path that my parents traversed where they lived a more linear-looking life in Michigan after meeting when they were 25.

Rebelling against you, Expectations, makes me exhausted. I know that more of you will always arise. It is unrealistic to assume otherwise as my environment inevitably plants more of your seeds. You are either front row dictating my life or on timeout in the corner with the dunce hat on as I lead it myself.

I am not doing those things. But you know what, Expectations? You’ll never guess what I’m doing instead.

I am living out my dream on a beautiful island. I am empowering a small Hawaiian shave ice business into a mindful journaling community. I am single and figuring out how to love myself. I am investing in the now to better support my future self. I am fit and healthy despite being in the largest pants size I’ve ever been. I am a shiny-skinned person because it is humid and hot here in Hawaii so, yeah, I do have pimples. I am sleeping fairly well most nights, listening to my body, and waking up with the sun every morning.

I am becoming emotionally available and open to the world and the potential prospects of serendipitous opportunities and life partners in it.

I am living my life.

Now, your voice sounds like mere whispers, instead of a blasting megaphone like when I was in college. I’ve made progress against comparing myself to everyone on a similar-looking trajectory. But your voice still slips in from time to time, disguised as fear calling me an impostor for living life the way that I do.

Photo by 愚木混株 cdd20 on Unsplash

I want to stop feeling like I have to choose between being a rebel going against the grain, or just one of the pack — like an obedient lemming jumping off a cliff matching the status quo. Can we get to a place where I don’t have to feel like this?

While working with you, Expectations, life is more motivating, exciting, and quite frankly, flourishing. You propel me to make things possible that I could never fathom. I know partnering together is not easy and life is inevitably more challenging as you get hijacked by the external, and fantasy, worlds. I want to recognize what is in our control and what is not then re-evaluate based on that. I will probably come short time and time again, but with your support, I want to set real expectations for me.

I am ready to be partners and at peace. Expectations, can we call a truce?


A recovering people pleaser

This wasn't written alone. Thank you to Ben Schneider, Steven Foster, Allie Crawford, Ellen Donnelly, Dan McGlinn, Steph Vermet, and Emily Waguespack for providing me feedback on the contents of My Letter to Expectations.


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