The Magic of Trying, the Blessing of Committing, and the Grief (+ Gift) of Quitting

Lessons from my 100-day Prose + Pastels creative challenge, why I'm quitting + how a failed endeavor can be counted a success

The backstory

Back in February 2023, on a whim, I decided to try a “Haiku + Sketch” creative challenge on Instagram. That challenge led me on a journey of discovery and unexpected clarity, leading me to begin a new journey as an oil pastel artist.

Inspired by last year’s journey and wanting to stay connected to both my writing and my art, I decided on January 31st of this year (another impromptu decision) to challenge myself again. This time I was going to try a 100-day “Prose + Pastels” challenge, writing one piece of prose and painting one oil pastel mini each day.

A word on the magic of trying + the blessing of committing

The magic of trying is that it reveals what’s possible. Without taking the risk that comes with trying, we will never know what we’re capable of or what is possible, and we won’t grow.

To try something or try something again is beautiful and courageous—the willingness to try is a must for any creative.

Beyond trying is committing.

To commit to something moves from treating something flippantly or haphazardously and requires attention, intention, discipline, and diligence.

The blessing of a commitment is that it cultivates trust (trust with yourself and others), and it can also reveal what’s possible.

When I think of making such a creative commitment as this one, it’s about discipline, yes, but it’s also about cultivating a relationship. I believe that showing up in this way with consistency bears much fruit.

By just trying and committing to a creative challenge even without finishing it, I have experienced some of that magic, that blessing, that fruit. Because it’s not about reaching the finish line as much as it is about showing up to the race.

Journal Prompts for Reflection:

How do you feel about trying something new or beginning again in the realm of creativity, writing, art, or other pursuit?

Have you ever struggled to keep a commitment to yourself?

What activity would you want to try for 100 days?

Before I began, I knew that 100 days would feel vastly different from 30 days.

Could I really see this commitment through every day for nearly 1/3 of a year?

That seemed long and especially difficult to be certain about a thing in a life defined by uncertainty. Yet, in knowing a lot about myself, I believed I could do it.

As someone who keeps my word (to others and myself) and can easily be described as disciplined and devoted, I had faith in my ability to accomplish my goal. My type-A, overachieving, perfectionist, productive self loves a to-do list, a checklist, a habit tracker, and a good daily challenge to hold myself accountable.

“Ultimately, you have to sit down and start to write. And even if all you do is type out ‘I can’t write this morning; I can’t write this morning; oh, bother, I can’t write this morning,’ that will sometimes prime the pump and get it started. It is a matter of discipline. It is particularly a matter of discipline for a woman who has children or another job.”

—Madeleine L’Engle

I value integrity, and I want others to be able to count on me. The problem is that I can be loyal and committed to a fault. I have been known to stubbornly keep my word just because I’m afraid to fail or afraid to disappoint someone.

There have been times when I have bypassed a healthy need to stop, pause, or change course. There have been times when I saw a need to adapt or be flexible, yet I dismissed it—oftentimes out of pride. This is, for sure, an area where my strengths can become weaknesses that inevitably do harm.

For the longest time, I interpreted quitting as the same thing as failing, and failing was something I feared. I also personalized it to mean that if I quit, I didn’t just fail at something, but I was a failure. This internalized fear of being seen as a failure has been one of the most significant motivating factors in my life, leading me to many of my successes but also costing me a lot.

Now, I know how to flip that fear. I know failure can be a great teacher. I have learned to cultivate a growth mindset, embrace mistakes, and see the good that can come from failing.

Do not fear failure but rather fear not trying.

—Roy T. Bennett

The gift of quitting (or maybe the gift of reimagining quitting?)

With all of that being said, after 39 successful days of creating “prose + pastels,” even amid travels and other challenges, I decided to quit my 100-day challenge.

But actually, I don’t want to use the word quit. I didn’t quit or give up because I couldn’t do it or didn’t believe I could finish the challenge I started.

I’d prefer to say that I decided to stop, and this stop is leading to a pivot. So maybe I could more accurately say that I’m not so much quitting as pivoting.

I also want to say that I am still counting this challenge as a success because I accomplished the goal at its heart.

My purpose in trying this 100-day challenge was to help me remain connected to and practice both my writing and my art—and it has. That is a huge win.

There are other wins, or gifts, too.

And these mainly have to do with listening.

“If the artist works only when [s]he feels like it, [s]he’s not apt to build up much of a body of work. Inspiration far more often comes during the work than before it, because the largest part of the job of the artist is to listen to the work and to go where it tells him to go. Ultimately, when you are writing, you stop thinking and write what you hear.”

—Madeleine L’Engle

I succeeded in listening to my voice and the voice of our Creator and following where those aligned voices led.

In listening, I was reminded that we don’t have to fear running out of ideas. There is an endless creative well we are invited to drink from. As long as we’re returning to the well by paying attention and listening, we will never run out of creative material or ideas.

I often think of Julia Cameron’s explanation here (this is my mixed paraphrase) that we’re not trying to think something up when we write our morning pages or create, we’re more simply putting something down and transcribing what we hear.

Again, the win here is that this creative challenge helped me refine my hearing and continue listening to life (hat tip to Frederick Buechner here), offering me the greater gift of spiritual attunement and connection.

This challenge also reaffirmed and revealed some things about myself as a creative.

Though I can do it, I don’t like churning out content quickly.

My pace is slow, and I enjoy creating prose and pastels that are afforded longer amounts of time to simmer.

Now, I could have approached this challenge in a different way that would have allotted space for my creative pace, such as working on the same piece of writing or painting day after day, but alas, I did not. Each day, I chose to start and finish a new piece of writing and a new painting. I gave myself permission to make them small and brief to make this possible.

Even so, I found myself wanting to spend more time on either the prose or the pastel. I wanted to return, refine, and shape my words and art into something more.

The prose and pastels I created each day felt like beginnings. I wanted to see what they could become if I slowed down and spent more time with them.

Of course, as a creative person, I want my creations to connect with others like yourself. And that was another gift—they did. The positive responses and feedback for my prose and pastels were overwhelming, affirming, and encouraging. You seemed to enjoy it—and so did I.

So, even though I’m no longer going to continue this 100-day challenge, I’m not really quitting.

I will, in fact, continue to create prose and pastels.

I’ll just be pivoting so that I’m doing them at a different pace. I’ll be engaging more deeply and thoughtfully with my art and writing in a way that is more enjoyable and sustainable for me.

In this sense, quitting doesn’t mean walking away from something or giving up on something. In fact, this decision is more like opening a door early to continue on the creative path.

Journal Prompts for Reflection

What thoughts, feelings, and experiences do you have about failing or quitting?

Do you feel inspired to rename or redefine any times you’ve failed or quit?

What is your life revealing right now when you listen?

Do you need permission to pivot?

But there’s more…

(I know this is getting long, and if you’re still reading, much appreciation to you).

So far, this may read with a shiny positivity that “this has all worked out how it was supposed to.” That is not entirely the case.

I want to share a confession of sorts regarding one of the main contributions that led me to end my 100-day endeavor early. If it hadn’t happened, I might still be pressing forward…

The truth is that my main motivation for stopping is due to painful happenings in my personal life. I stopped because this season has become busier and more stressful than I anticipated. Some of the difficulties in my personal life have thrust me anew into depression and caused me to rearrange my priorities and responsibilities just so I can survive the day.

I’ll be honest, I don’t like this place. It’s a place I’ve been too many times before. And there’s a fair amount of grief to be processed privately here.

I’ve learned how to be gentle and honor myself and the season I’m in while not abandoning myself or my creativity entirely—even when everything seems to scream, it’s all going to sh*t, it’s not.

The inner critic and perfectionist in me cringes for not finishing 100 of 100 days. Honestly, there’s some genuine grief to be felt around this. I don’t want to dismiss that reality. It’s a bummer life swung at me the way it has and that it was a contributing factor to this decision to stop.

And yet…

I’m still here.

I’m still writing.

I’m still painting.

And even amid the sorrows here, there are new creative joys on the horizon.

Now, I will officially bid farewell to this 100-day creative challenge. Thank you for your time, service, and gifts and for leading me down (and helping me say hello to) the path I need to be on.

Cheers to those of you who need permission to pivot from a commitment and redefine your idea of quitting.¹

Cheers to those of you who keep showing up with grit to the writing and art that help you breathe and come alive.

Let me be honest; the lyrics “I get knocked down, but I get up again”² are playing in my head as I finish writing this.

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If you’ve enjoyed my prose + pastels

I’m so glad!!

I’m going to keep sharing (and maybe re-sharing).

You can continue to enjoy them over on my Instagram account which is basically like a mini-virtual art gallery.

You can also find a few original minis available for purchase in my shop.

When life allows, I will be releasing more originals to my shop, updating my art print shop, adding some prints of my prose to the shop… and creating new prose + pastels.

Thanks for your support. Now I’m going to go rest for awhile.

—Kristin

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P.S. Do you want to devote some time to your writing?

Join me for March’s Pen & Mend Writing Room opening tomorrow (Friday, March 15th) at 9 am PT/noon ET. I really need this one. I hope to see you there!

And mark your calendars for April’s writing room opening on April 19th at 9 am PT/noon ET.

1. The idea of quitting something has come up repeatedly for me. If this resonates with you, I want to share two such related resources with you: 1. Listen to Write Your Story with Ally Fallon episode “How To Know When To Quit Something,” 2. Read How to Walk Into a Room: The Art of Knowing When to Stay and When to Walk Away by Emily P. Freeman.

2. For your listening pleasure, see “Tubthumping” by Chumbawamba.