Don't 'Should On' Yourself

reader story Jan 28, 2024

We're excited to share this week's blog post written by Grieve Leave community member Dillon Cobb, "Don't 'Should On' Yourself." In this post, Dillon reflects on his grief journey and how removing "shoulds" from his vocabulary was crucial for him as he grieved.

"You should be…

 …doing something.”

…doing something different.”

…thinking a certain way.”

…looking a certain way.”

…spending your time, money, or energy on ___________.”


Let me stop you right there. How about we not “should on” other people, and let's also not "should on" ourselves. 


The voice in your head often has good intentions and usually contains good advice. Unfortunately, that good advice was tailored for someone else and then repackaged for you. You are not them. You are unique. Your journey, your past, and your future are different than theirs. How do they know what is best for you? How do you know what is best for you? 


This is ironic coming from me. I own a business called Simply Human Advisors. Yet, these days, I mostly listen to stories while giving little advice. To be clear, some things need immediate attention, but sitting and waiting solves many problems. I am continuously surprised at how many problems solve themselves with time. 


With that said, people regularly ask some variation of the following question: "What must be done now? And what can I put off until later?"


Sometimes, what must be done now is to simply take a step back and just be. There’s nothing that illuminates that truth more than grief.

The short version of my story is one of loss. My best friend was killed in a car wreck on his way home (we were neighbors, too), but calling him a friend falls way short. We called ourselves a framily. The Cobbs and the Rogers had become the Cogers. I made a short video of our friendship story


In March of 2024, it will have been three full years, which is hard to fathom. It feels like yesterday. I still occasionally pull out my phone to text Mark, only to remember he is not there. You probably know the feeling. 


His widow and all three kids were also in the car during the accident. All survived, but their daughters were both badly injured, and one was critical for a while. In the hospital, Jenn asked my wife and me to sit bedside with one of the kids in the ICU. She wanted us to be the first face they saw upon waking. Not grandparents, aunts, or uncles, but the Cobbs! 


Upon hearing that her daddy was gone, their oldest daughter asked, "How is Dillon?"


I'm not ok, baby girl. 


Three years later, my life has taken a path I only ever dreamed of because, well, you see, I am a CPA. Most CPAs live in a constant state of fear. We are hyper-aware of risk. We are the original bubble boy. Please do not ask us to spend money. We are the kings of living for tomorrow. 


After the most incredible human was taken from us, fear means something completely different. I can no longer afford to live in fear. Fear means missing out on life. Fear means waking up as an old man with a laundry list of regrets. Fear means not being present today. Fear means missing out on the journey.


Enter my own “Grieve Leave.” I never intended to take a leave from work, but that is essentially what transpired.  Going back to my old job was no longer an option for me. I had to start on my own. My wife took a different job (think bigger role with more responsibilities) that could support us while I spent a lot of time…grieving.


I cut back on lots of commitments. I focused on the things I enjoy. I read more books and listened to more podcasts in that year than the previous 5+ years combined. I walked in solitude. I played games with my kids. I cried a lot. 


My friend Mark made everyone feel loved. He was the best at staying in the present moment. He was a master at not wasting time. He never took life for granted. He rarely delayed gratification. At least in this way, he and I were on the opposite ends of the spectrum. 


I realize now that a life lived for some future place and time is not a life lived well. We talked about this for years before he died, and his death cemented this for me. I have learned how to hold space for grief and joy at the same time. I can be happy and sad. I can use my head and my heart together. I can intentionally plan ahead but also live in the present moment carefree. This is not an either/or discussion. This is not black or white. This is life. 


The more people I talk to, the more I see nuance. No two stories are the same. Every journey is unique. Because my path is unlike anyone else, the first step for my healing was to remove "should be" from my vocabulary. So maybe next time someone says you should be doing something, tell them, "Don't should on me!"


And don't "should on" yourself either!


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