Should-ing Myself To Death

For the first time in a very long time, I turned my phone on airplane mode and gave myself a day of no scrolling. No projects. No “I really should” to do lists. 

Going back to a more typical travel adventure in cities versus the van has inevitably meant fewer breaks. It was far easier to disconnect when I was driving for 3 hours, had crappy service, or my phone died. I could find something beautiful to see. Something of a higher priority than social engagement. When I’m on a plane and in a city, there’s always service or some excuse to charge and check my phone. Beautiful places are a rideshare away. Plus, a plane ride isn’t nearly as relaxing as a long drive, even if the middle seat is empty. 

That digital connection and endless scroll have only made me feel more alone. In times when I used to wake up then take in the fresh air and the quiet of the woods around me, I now scroll. For what? I’m not sure. I’ve never found what I was looking for. I don’t feel uplifted or excited about what’s next in my day after mining for endorphins through this endless social feed filled with recommendations for my life. Instead, I leave with this scrolling list of tasks. All the things that I could be doing. Things I tell myself I should be doing.

My mind responds in a few different ways when I’m should-ing myself to death. First, I become the person with a strategy. I find a way, build a system, set my alarm. With all good intent, I build rigor that implies that somehow I’ll be better for it on the other side. A routine for avoiding this feeling in the first place. 

On other days, I will console myself with reality. I’m busy. I don’t have time for a new routine. I’m overwhelmed. I give myself an excuse for breaking the rule without ever ridding myself of the “I’m a failure” feeling. 

The days where I’m doing this living right, I respond with kindness. My mind has ridden enough rollercoasters to barely trust that what I want is enough or that this happiness will last. I can be gentle with the part that wants to create a list of should-do tasks simply because that was the old formula for success. I can recall in the moment that comparison is a thief of joy. I can let myself feel and know that today is enough. That I am enough.

I can also remember that if I wanted to change everything, I could. I have. So can you. But right now, this day, wasn’t made for should-ing ourselves to death, applying more rigor, or comparing our lives to a social media stream. This day was made for finding something beautiful in the sunshine or another person. Finding something beautiful in the life we are living today, not the list of where we should be. 

Weekly Letters

Kat Kibben View All →

Kat Kibben [they/them] is a keynote speaker, writing expert, and LGBTQIA+ advocate who teaches hiring teams how to write inclusive job postings that will get the right person to apply faster.

Before founding Three Ears Media, Katrina was a CMO, Technical Copywriter, and Managing Editor for leading companies like Monster,, and Randstad Worldwide. With 15+ years of recruitment marketing and training experience, Katrina knows how to turn talented recruiting teams into talented writers who write for people, not about work.

Today, Katrina is frequently featured as an HR and recruiting expert in publications like The New York Times, Chicago Tribune, and Forbes. They’ve been named to numerous lists, including LinkedIn’s Top Voices in Job Search & Careers. When not speaking, writing, or training, you’ll find Katrina traveling the country in their van or spending some much needed downtime with the dogs that inspired the name Three Ears Media.

1 Comment Leave a comment

  1. Just what I needed to hear today. I will take time to find the sunshine and stop worrying about the “should-ing”. Thank you for sharing your wisdom.