“Stop ‘should-ing’ on yourself,” someone once said to me. It made me laugh when she said it, and then I immediately realized how much I had been “should-ing” on myself my entire life.
We are conditioned for it. Our upbringings, societal pressures, and life experiences can all lead us into massive amounts of self-limiting behavior. “I can’t do that.” “That would never work out.” “I’m not good enough for that.” I was adept at regularly telling myself those false stories.
In March of 2020, the real awakening began for me. I was staring down the barrel of the COVID pandemic lockdown, having just received word that my divorce was final. I realized that I had “should-ed” my way through too many years in a marriage that didn’t feel right and felt trapped in a job that was becoming more and more unhealthy.
For many people (myself included), lockdown was uncomfortable because it meant sitting with all of the hard feelings we usually try so hard to distract ourselves from or otherwise avoid. I was in a swirl of some of the most difficult feelings I’d ever encountered, and ended up spending way more quality time with myself than I would have preferred. Looking back now, though, it was exactly what I needed. Excruciating, but simultaneously freeing, it opened my eyes to how many dreams I had put on the shelf all in the name of “should”. How much I had lost faith in myself and given that power to others, all because I thought I “should”. How I let fear take the wheel far too often and, in the process, sacrificed the very thing that makes me a vital and vibrant human…being true to what I know is right for me.
I had tried so hard to live a more conventional life. Good job. House in the suburbs. Married. A dog. I didn’t have the white picket fence yet, but that was on the list for the following year.
I was bored, miserable, and completely burned out.
When I started to question what my life would be like if I took those limits off, it felt scary. I liked plans. Order.
When I was younger, I used to pretend I wanted a more conventional life because I thought that’s what I “should” want, when in reality, I was in the corner flipping through National Geographic magazines and encyclopedias*, dreaming of seeing as many places as I could before I died. I aspired to be “successful” (i.e. good job, nice car, beach house) because that’s, of course, what I thought I “should” do in order to be accepted as someone who wasn’t a failure. As a teenager, I went on unhealthy diets trying desperately to shrink myself into an image of what I thought I “should” look like. I was a straight-A student. Valedictorian of my 8th grade class. Enrolled in Honors and AP courses in high school. Nothing was ever good enough, and running on that hamster wheel of “should’s” was exhausting. Always trying to fit into the boxes laid out for me, no matter how uncomfortable. Trying to cram myself into them was going to be the end of me.

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Dreaming big dreams while standing on this dune was
a pivotal moment in the returning to myself.
When I started to question what my life would be like if I took those limits off, it felt scary. I liked plans. Order. It felt good to know what was coming around the bend…or at least to have planned and overthought every eventuality so I could prepare myself for anything.
In service of trying to plan for some of those worst case scenarios, I was frequently the master of the “What if….?” What if I end up penniless on the street corner? What if I fail? A good friend looked at me after a session of my “What if-ing” and said, “Yeah, but…what if it all works out?” I remember that now anytime I feel myself slip into catastrophizing. “What if…” can actually be a really empowering question.
Success means something very different to me now than it did a few years ago.
So, what does all this mean for me now? I’m certainly not perfect at it, but I’ve made some significant progress at keeping the “should’s” in their place. And my “What if’s…” are now reframed as dreams when I catch them peeking around the corner at me trying to entice me down the fear-based rabbit hole. When I used to think about the future, it would be 90% terror and 10% excitement. Now, it’s the other way around.
I’m completely in love with the fact that I’m no longer striving for a conventional life. I have been liberated now that I’m not trying to contort myself to fit into those boxes anymore. I don’t know the specifics of what the future holds, but I know this…I’m the happiest I’ve ever been, and my dreams are no longer collecting dust on the shelf. Success means something very different to me now than it did a few years ago.
I took the leap into a job that was much healthier for me. I’m going to be self-publishing a book that took me years to write. I don’t care if it becomes a bestseller—putting my creation out into the world is enough. I’ll be traveling overseas this spring and am counting down the days like a kid counting the days until Christmas. I’m pursuing a future that will allow me to live abroad and see the places I saw only in pictures as a child. And I will continue to run full-out toward the soul of myself again and again. No matter what. I hope you do, too.
*If you’re too young to know what an encyclopedia is, check this out and be glad you’ve never had to flip through an index with 8-point font and a 28-47% chance of finding what you wanted.
