Can You Make The Right Choice?

I hate dress clothes. Screw you, business casual. On my way to the gym or out for errands, fine. I can throw on some gym shorts. But when I have to pull together an outfit for a meeting or presentation, I get analysis paralysis. I don’t like how the shirt fits right around the waist. The dress pants always feel too tight. My shoes are uncomfortable. It feels like my mind can take any choice and make it feel like the wrong one.

Clothes aren’t the only example. The same thing happens when I think about the future of my business and life. Questions like “where should I establish roots” and “what will I work on for the next 5 years” come with just as much frustration as a pair of pants that just don’t fit anymore. A rage washes over me. I should just know. It shouldn’t be this hard. 

This sometimes disastrous mix of confidence and self-doubt in my mind makes every choice look like a dead-end. The scariest part is that I can lean all the way into some idea to only end up exhausted and filled with self-blame. That’s the worst part of finally making a decision at all, if you ask me. The part where you wonder if it was a good idea after you’re 80% done with the work. See: multiple drafts of half-complete books on my desktop or when I’m halfway to the venue and realize there’s a big hole in the crotch of those pants. 

This week as my person and I started our plan for the next phase of life that includes some time on the beach and another year traveling in the van, I felt that overwhelm wash over me again. “Maybe we should just buy a house and settle down,” I found myself saying. 

But that wasn’t a vote for what I want, it was a bet on what seems predictable. I have been convinced for most of life that the trophy to tell the world I was doing it right was measured in square feet. The American Dream I was sold from a young age surely didn’t include living in a van by the river. No, I was sold picket fences and big houses with a lot of windows. 

I get so stressed out about making the right choice that I often forget just having choices is a gift. Those picket fences are an option, but not the path I want to take right now. In the same way I can choose to put on the dress pants or a pair of basketball shorts today, my life is filled with options. To my anxiety’s surprise, I am beginning to believe that’s the good part

Whether they take my life across the country in a van or into a home with a beautiful kitchen, options are the reward. I’m lucky. I owe it to myself to expand my horizons. Question my beliefs. Learn new things. Stimulate my heart and mind. 

The more I stress, I can see that obsessing over how to make the right choice is standing between me and feeling the joy of a life well lived. There’s no such thing as a right answer whether I’m picking pants or my place. Having options and trying them out is the fun part. Wherever I end up is right for now. If it’s not, I’ve got four wheels and the option to just keep going. 

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.

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