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14: What It Feels Like to Should On Yourself

In bed this morning, watching the stripes of daylight that came through the blinds, I had this thought: you should be making more money by now.

I was thinking about a coach I’d love to hire, but she’s pricey. Yet in my fifth year of business shouldn’t I have the cash for a $15,000 investment in coaching? 

I went to the living room to write this, but first I spent 30 minutes watching a YouTube compilation of a podcast. This is such a waste of time, I thought as I listened. You should be writing or stretching or reading or exercising or cleaning or…. 

When you slow down and observe, it is AMAZING how many thoughts and actions start with a “should” thought. In my experience, these thoughts don’t feel good, because they tell you that you’re doing something wrong.

What IS a should thought, and why are they so painful? It’s somebody else’s voice. It’s an idea that comes from the outside world, instead of from your heart. For example:

  • You should be making more money by now. Says who? Why do I think this? It’s not like there’s some external rubric that indicates how much money everyone must make by a certain age. No, this thought comes from articles I’ve read about how you should make money when you’re young, before you have children, so you can take time off to parent if you want. It comes from the people I follow online, young women entrepreneurs like me, who talk about their six-and-seven figure businesses. It’s from comparing myself to my friends, who are making more money than I am even though our businesses are the same age
  • You should be writing or stretching or reading or exercising or cleaning. Some people watch YouTube videos every day to entertain themselves. But I feel guilty when I do, because of what I learned as a child: that watching TV will turn your brain to mush. Or because watching YouTube isn’t “productive,” and you shouldn’t do things that aren’t moving you towards your goals. Because of articles I’ve read that tell you to eliminate whatever doesn’t bring you joy (in my case, videos don’t usually bring me joy).

It begs the question: how much of your work and what you spend time doing is motivated by someone else? It could be your parent, a teacher, a friend, or a stranger who wrote an article online. And what would it take to sail your life-ship motivated by whimsy, spontaneity, desire and joy? What would it look like?

When I ask myself those questions, it brings up a lot of fearful thoughts. I fear that I would become unreliable, that I wouldn’t make progress toward my goals, that I would disappoint people, that I would lose my way.

What happens when you ask yourself those questions?

Image by Yoori Koo.

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ABOUT THE AUTHOR

EVA JANNOTTA

Eva is the founder + CEO of Medusa Media Group and supports women through every phase of thought leadership, from developing, to writing and producing, to marketing and amplifying magnetic thought leadership content.

Eva's clients are bestselling authors, TEDx speakers, LinkedIn Learning instructors, keynote speakers, podcast hosts, and named among LinkedIn's Top Voices.

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