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Learning to Let Go | Katharine Chestnut

Learning to Let Go

You’ve probably seen the phrase on Instagram, or if you’re a Disney fan like my sister, you’ll remember it from Frozen

“Let it go.” 

I considered the phrase again recently, inspired by autumn and the season of “letting go.” After the last few months of summer and growth, many living things around us will shed their leaves or go into hibernation. 

Let go of the things that are no longer nourishing or supporting you. Then welcome the same kind of growth that you see in the world around you. 

What We Can Let Go Of

There are a few benefits to shedding the things that no longer serve us. Whether it’s an appliance that’s gathered dust in your cabinet or a negative belief that’s holding you back. Letting go of these things makes room in our lives for something more supportive. In a way, letting go can “lighten your load,” so that you can make progress in a new direction. 

Sometimes learning to let go could mean leaving a role that we’ve played in our lives. My own career path is a great example of how I shed my leaves after a season ended:

Learning to Let Go | Katharine Chestnut
  • After getting a degree in Fine Arts, I wound up in advertising.
  • Even though advertising wasn’t a good fit, the world of marketing was still attractive. I enjoy creating a strategy around communicating and connecting with people. 
  • I bumbled along my way into trade shows and face-to-face marketing. 
  • My passion for creating experiences and building community drove me to achieve the highest level of certification.
  • Which in turn led me to the coworking industry. Today, I own a coworking space, where I’m honored and overjoyed to support the small business and entrepreneurial community that grows here. 

I wouldn’t have guessed when I started working in advertising that I’d wind up with my own brands and businesses to run. The course of the ups and downs of my career reminds me of playing ‘snakes and ladders’. As I child, the game taught me that even an expected surprise can end up being a good thing. In my adult life, I learned that by letting go of certain things, sometimes a “good job”, can make room for experiences that are ultimately far more fulfilling. 

And you don’t need me to tell you that can be really difficult at times.

Why Is Letting Go So Hard? 

We’ve all been in relationships or jobs or situations that just didn’t work for us. We call that “being a bad fit.” Many times that’s because the role that we’re playing at the time isn’t totally authentic to us

There are more than a few reasons why some people just can’t seem to let go of an idea or person. 


Learning to Let Go | Katharine Chestnut

For many of us, clinging to old beliefs or toxic relationships is a kind of perfectionism. I know I can be determined to carry out a task or perform with no mistakes. Even though I’m working on not being a perfectionist, that determination has often helped me get through some challenging situations. 

Some perfectionists laser-focused on doing their best or “sticking it out”. Which ends up being a distraction from the path toward our true selves. 

Healthy striving is self-focused: ‘How can I improve?’ Perfectionism is other-focused: ‘What will they think?

Brene Brown


Letting go of what other people think about us can be quite difficult. Often we try so hard to live up to other people’s expectations of us that we carry those expectations around with us. When we meet their expectations, we’re rewarded.

It’s difficult to let go of the things that might have served us well in some way. Changing our behavior can be scary, because we don’t often know how it might impact others not to mention ourselves.

It can feel like we’re giving up on our goals. However, the opposite is the truth: letting go of expectations means you are taking full responsibility for your life and happiness. You stop expecting others to meet your needs and instead learn to take care of yourself.

Fear Of Change

And how about just NOT changing? It is just a lot more comfortable sometimes in the status quo! 

Clinging to those situations can actually become a burden. In fact, the fear of change is so prevalent, there’s even a phobia about it: metathesiophobia.

Some of the areas experts suggest to overcome fear of change are: research, organize, embrace the change and more.

How to Practice Letting Go

When we let go of habits, relationships, or roles that no longer support us, it can reveal some amazing things about who we are at our core. 

Some people believe holding on and hanging in there are signs of great strength. However, there are times when it takes much more strength to know when to let go and then do it.

Ann Landers

You might find that letting go of your perfectionist tendencies reveal a person who is hard working and creative. Letting go of a “bad” habit might free up time in your life to learn a new skill. Letting go of a relationship that negatively impacts your life makes room for healthier ones (or more time for yourself).

Letting go really just means that you’re writing a new story for yourself. 

How does your story shift?

Want to jump start your practice of letting go? Get your ideas out of your head!

For one week, I challenge you to spend just fifteen minutes each day writing out the things that you want to let go of:

  • The conversations you want to have with people (but don’t)
  • The frustrations you have with a coworker
  • The grief that you’re feeling for an old relationship

It can be messy, it could just be a series of bullet points, and it might not make sense to anyone else but you. That’s the goal, though: To unload whatever it is your brain is carrying around, so that you can make room for another story or idea. 

And, of course, I recommend using your Inner Affirmations journaling to connect with your inner wisdom quickly and be truly authentic.

Journaling Challenge | Katharine Chestnut