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How to Stop "Shoulding" + Start Living in Order to Live Your Best Life

Stop Shoulding Yourself

June 11, 2021


For Jill Andersen, a speaker and coach in Greater Des Moines (DSM), “shoulding” had become a way of life. The Cedar Rapids area native and ISU grad majored in food science, which served her well for 20 years. She worked for General Mills, where food became a fun and interesting career. But the longer she was there, the more she thought there must be something more. So, she left the corporate structure and started to do freelance work. She hired a career coach to get some guidance and through that process, she realized she was meant to do something else.

As she worked through her next steps, Andersen’s own life coach gave her permission to do whatever it was she wanted to do. In that moment, she realized she had been shoulding herself her entire life, checking off that list of going to college, getting a job, having kids, etc., but forgetting to ask herself an important question: was this the life she really wanted? It wasn’t. 

Andersen saw herself as someone who could help others through coaching, too, and that’s where her new journey as a speaker and coach began.

Stop Shoulding Yourself

Andersen’s own podcast, “Stop Shoulding Yourself,” offers insight into shoulding tendencies and how to break free of shoulding in your own life. She said that when she’s in the deepest funks, she realizes she is shoulding herself the most and advises clients to keep track of all the times they say should throughout their day, as well as notice the times when their body is displaying resistance towards something on their to-do list. Is it something that they really need to do? Is it something someone is telling them to do? Andersen said the more someone asks these questions, the quicker they’ll get in tune with what their body is telling them. 

Andersen tells her clients that she doesn’t have the answers, they do. She recommended:

·      Listen to your intuition. 

·      Ask yourself, “Why not?” 

·      Try something new. Allow yourself to gravitate to new things in order to learn what fuels you in life.


Humans love routines, but getting out and seeing the world is worthwhile. There’s a lot to be said for trying something and not giving into perceived fears. 

Lessons Learned

Everything a person does in life has a place, and those things never go away. Andersen didn’t see the creativity in food science in the beginning of her career, but over the years she unlocked creativity and energy through her interactions with others. She brought all of that with her on her entrepreneurial journey, and said it’s important to figure out what makes you come alive and reflect on what has kept you stuck. 

Advice Post-Pandemic

With so many on edge about life returning to “normal” after the COVID-19 pandemic, Andersen said that going back to something is an expectation we’re holding over ourselves. We need to look at what we want to do with the days we’ve got. 


Listen to the entire podcast above.

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Startup Stories DSM

Startup Stories DSM is a podcast featuring conversations with entrepreneurs who share both their victories and failures on their paths to success. It is produced by the Greater Des Moines Partnership.