Making Peace with Failure
Cheers to you from gorgeous late summer in Seattle.
I’m in the Pacific Northwest for the next few months, spending time around Seattle and Portland. My plans include, variously, planning out visions for Q4 and 2024, opening registration for the next round of CARE, eating my bodyweight in Ellenos yogurt, exploring this corner of the world, meeting up with museum world friends I haven’t seen in ages, making a dress that will be my first me-made clothing project (under the tutelage of my excellent friend, Stacey), and cat sitting for the adorable and cuddly Henry.
The most eagle-eyed among you might notice I didn’t mention the Work/Life retreat that I’d previously announced.
And that’s because the retreat isn’t happening.
I could tell you a tale of how this came to be that made it seem like a straightforward choice to cancel. I could spin a yarn about how the timing wasn’t right or the stars didn’t align or it wasn’t meant to be. Instead, I’m going to be straightforward about it: no one signed up.
And in the name of further transparency, I want to use it as a little case study on making peace with failure.
Before you think this is about to be a tech bro screed about moving fast and breaking things or an Instagram graphic spread about how failure is actually a great teacher for us all, that’s not at all my intention.
I hate the feeling of failure. I’m a lifelong, trying-to-be-in-recovery perfectionist, and a type A, oldest child overachiever. My emotional default is to internalize any failure not as “this thing didn’t work right now” but “this thing is worthless, I am worthless, I will never succeed again”. I’ve named my inner critic Should-erella because she is constantly telling me I should be doing more/faster/better and achieving greater things.
Should-erella is not pleased that this retreat isn’t happening.
Here’s the thing, though. Should-erella aside, I’m mostly OK with it.
I announced this retreat just over a month ago, and then headed off to Maine for my annual reading retreat, which happens in a cabin without internet. That meant I was spending my prime marketing window away from my marketing channels. Marketing does not come naturally to me. It takes me a long time to write and send newsletters and posts and to make social media content and to reach out to potential marketing partners to spread the word.
I could have used some of my vacation time to drive the half-hour to the nearest wifi spot and worked on writing and posting and getting the word out. I could have tethered my computer to my phone’s hotspot and set up shop in the cabin. I could have looked up and realized that whole days of my vacation time were taken up with work to get the word out about this retreat.
Should-erella tells me those would have been superior choices to the ones I made.
Because I didn’t do those things. Instead, I decided that the reading and break time was more important and that a “working vacation” is, in fact, not a vacation at all.
While my annual reading-by-the-lake time in August used to be a much-needed departure from the stress of New York City pace, I no longer need it as an oasis of calm in an otherwise bustling life. I’m happy to be living at a calmer pace overall these days, so I don’t feel the need to reach for tranquility the way I used to.
Instead, I’m now rolling through my Ball Bearing Era (all pivots, all the time), with the future much more open-ended than it was before I went professionally independent. Even when I’m feeling at my best about my business and prospects, there’s still a little internal reminder—hi Should-erella 👋—that I should be more successful, more financially stable, more aware of what’s coming next.
For the past few years, my reading retreat time in Maine has been more about providing one of the other benefits of vacation that is so often overlooked in our capitalist productivity-driven working world: time off.
Off, as in away from work responsibilities.
Off, as in giving a rest to the part of my brain that needs to strategize about what I’m doing to grow my business.
Off, as in giving myself the full-throated permission to compartmentalize and stop stressing about all of Should-erella’s urgings toward growth and scale and speed and just be at the lake.
I’ve always been good and vocal about how my time outside the office is just that: my time outside the office where I won’t be working or responding to work concerns. When I was working full-time in institutions, that was generally easy to uphold (with a huge red flag of an exception made for my last full-time gig where my boss often resorted to sending text messages to my personal phone at any hour of any day of the week).
Now that I’m working for myself, it’s harder to compartmentalize and “shut off” the work part of my life. Even when I’m not actively engaged in work tasks like meetings or planning or admin, I now have much more porous boundaries between my work-life and my non-work-life. I no longer want to have to keep my life quite so rigidly partitioned as it used to be, and since I’m running my own show, I can find the balance that feels best.
In creating offerings like CARE (my membership community of arts entrepreneurs) and Reorientation Retreats (dedicated time where we apply new approaches to familiar problems), I am very much inventing the things I want to see in the world. I’ve struggled to stop defining myself by my work and to change the role work plays in my life. I’ve been lonely in the world of new entrepreneurship and sought out people to talk to. Plenty of other folks have told me they’re wrestling with the same things.
And so I’m developing offerings that answer these concerns. They’re new and evolving and responsive to what I hear through a lot of listening and conversation.
That means that my work worries are a whole lot more existential than they used to be. They aren’t problems that stop at 5pm and wait to be picked up only upon return to the office. It’s not as easy for me to lay down my work worries now that they’re bigger and more amorphous than “ugh… tomorrow I’ve got to finish my budget spreadsheets”.
My Maine retreat is one of the few times that I’m still able to compartmentalize successfully. It’s such a particular environment, and the rhythms of reading and relaxing and waking/sleeping based around the sun have been well established after more than 20 years returning to the same region. It’s one place where I can still stop some of the ruminating spirals that get started, with Should-erella reminding me of all the actions I have yet to take.
I think you probably get the idea by this point that, even though what I need from my time in Maine is different than it used to be, I still need the break.
A working vacation was not going to give me that. It’s such an oxymoron, the term shouldn’t exist. #CapitalismMakesFoolsOfUsAll
So this year, I let my time off be time off, and even though that means that my Seattle retreat isn’t going to happen, I feel good about the decision I made.
Are there things I can learn from this failure? Sure. Pay careful attention to scheduling. Think about what work is required for a project and when it’ll get done. Give myself grace when trying to make a program happen in an area that’s outside my immediate networks.
But as I said up top, I’m not trying to turn this into a “nothing’s a failure if you learn from it” situation.
My Seattle retreat plans failed.
I prioritized my overall well-being above my business.
This one offering failing does not mean I am a failure.
I don’t feel good about the failure.
I do feel good about how I prioritized.
All these things are true, all at once.
My independent business isn’t even two years old yet. It is continuing to grow and morph and find its way. That’s not always comfortable (as change so often isn’t), but I stand by it and acknowledge it. As my Janine Antoni inspired tattoo reminds me, I can choose where to hold my ground and where to cede it.
I apply force, I rotate, I give way and transform, offering self
Failure is a sometime companion along the way.
Creative Prompt Coda: Choose something you do in your regular routine and for one day, do it as a celebration.
