Featured Artist In Action: Caitlin Kunkel

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Today’s featured Artist In Action is Caitlin Kunkel, who is here to share about her path as a writer and how private coaching has supported her along the way, especially as she published her first book last month!!  This is a great insider’s view to how personalized the private coaching experience can be, and we hope you enjoy learning more about coaching from Caitlin’s perspective. Oh, and do yourself a favor and get her new book asap – it’s the perfect holiday gift for your feminist friends. 


1.  What initially brought you to Private Coaching?

I came to private coaching in a complete frenzy – along with my three co-authors, Brooke Preston, Fiona Taylor,and Carrie Wittmer, I had gotten a book deal off a satire piece we wrote for McSweeney's called “New Erotica for Feminists” that went unexpectedly viral. I had insomnia and my physical and mental health was ROCKY. I talked to Betsy for the first time right after we had written a book proposal, secured a US and UK deal, gotten a lit agent, and been given some truly frightening deadlines. Usually a book has 1.5-2 years in the publication process. THIS book needed to be written in three months to meet the deadline for the publisher to have it out by Christmas and to capitalize on the viral success.

Sounds amazing, right? And it truly was, except as a freelancer, I was already stretched really thin with jobs booked out for those three months – teaching comedy for Second City, writing for a public radio show called Live Wire, and all the various freelance assignments you line up to make your income goals.

The four of us also edit the comedy website written by women and non-binary authors,The Belladonna, about 5-6 hours a week per person, and that was unpaid as we were growing the site and deciding how to scale it.

So the idea of adding the intense process of writing and editing a book of JOKES pretty much sent me over the edge mentally. I have a friend who is a great humor writer, Jiji Lee, and she had mentioned Betsy and the PATH course to me before. I decided I needed to lay out some cash to have someone help me manage this unexpected upswing in my career to be sure I didn’t burn out between March 2018 and the end of the year, when we would be done with the first major push of promoting it. Basically, I came to Betsy in crisis mode, worried about not being able to truly leverage the biggest professional opportunity of my life to date.

2.  What goals have you set in your Private Coaching work? Did you meet them?

At first my goal was pretty dire - not to burn out (and die??) and lose all my work because I couldn’t handle all the deadlines – I had already felt a bit on the brink prior to getting the book deals, so I think they pushed me to a breaking point I would have reached eventually anyway. I LOVE to work, and I love what I do, so I kept taking on more and more students, lecturing, writing assignments, etc. thinking that I would just work harder. I was a long-distance swimmer growing up all through college and still really believed that I could do anything if I just put more and more and more effort into it. To me, failure to meet a deadline really felt like a personal failure of discipline and focus. That’s…a rough way to work.

So when I started talking to Betsy it might sound silly, but for the first time in my adult life I had reached the absolute ceiling of what my brain and emotional state could handle. I needed triage from her at first – our first session we just wrote on paper every single assignment and deadline I had for that month. It was horrifying to see how overextended I was, but like when you finally open the overdue bills, knowing just have MUCH time debt I was truly in was the first step to being able to make a workable plan. I worked weekends for about four months in a row, but KNOWING I was going to have to do that and knowing when it would be over, rather than doing it every weekend in a blind panic of “wow this is my life forever haha everything is fine!!!” actually helped me mentally.

Since talking to Betsy over the past six months, my goals have become to be realistic with myself and how long my various types of work are actually going to take me. I Iay out my week on a blank sheet of paper every Sunday night to visualize the amount of tasks I have to do (so not a schedule as much as a visualization of how much brainpower needs to be expended on each day). Betsy also helped me realize that constantly switching between teaching to speaking to business writing to creative writing to meeting with people to social media saps my strength and focus, so I allot certain days to certain tasks rather than trying to hit 5 different spheres of work in one day. This helps me feel a lot less frantic at the beginning of each day, and to go into each area for a longer and deeper period of time.

3.  Can you talk about what your career path has been like since you started coaching?

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Well, with Betsy’s help, a lot of support from my husband, and the creative partnership of Brooke, Carrie, and Fiona – we DID finish the book! It was published by Plume (Penguin Random House) in the US, and Sceptre  (Hodder & Stoughton) in the UK. We wrote it from March to June, edited it from June to the end of August, and then took about two weeks off prior to beginning to promote it! It came out in the US on November 13, 2018, and the UK November 15, 2018, and now we’re doing a bunch of events in NY, DC, London, Portland, Chicago, Columbus, Providence, and more to get the word out! The launch week was the absolute highlight of my career so far – to travel around to places like Google and Books are Magic (Brooklyn’s awesome indie bookstore) to talk about satire and feminism with excited, smart, amazing people really makes all the work and thought and worry feel like it’s paying off.

For years I’ve felt very confident in my skills as a teacher, and I know that I am very good at it. I haven’t always felt the same amount of confidence in my own creative work, but I am extremely, extremely proud of this book. To have created a thing that people can read and hold and share and laugh at is a tremendous confidence booster in my own creativity and sense of self.

4.  Was there anything about the coaching experience that surprised you?

How much it helped just to verbalize how panicked I was. I know Betsy isn’t a therapist, but it was majorly helpful to me to talk through WHY I kept taking work, even as I felt the burnout coming on. I realized that I can let some teaching tasks go and it’s OK to feel sad about that, since I truly love to teach, and when I was inclined to want to overbook a week or month, I pulled back and tried to ask myself what emotional state was driving that urge to overwork. Did I feel isolated and want connection? Did I want to feel like an authority? I like money obviously, but a lot of times I would do work for free or for a low amount of money just because I love to feel competent and respected. I learned to try to untie those emotional urges from work and be more dispassionate – did I have the time? According to my rubric Betsy helped me make, was this worth the investment and energy? Or was I kneejerking the response? I’ve always thought of myself as not a very emotional person, so to really start to understand the role emotion was playing in my work life has really changed my perspective on work and how it fits into my life.

5. How would you explain the coaching process (from your POV) to someone who isn’t familiar with it?

For me, it was like getting someone into the mess of my brain and helping me sort it out in a way that made long term sense. Basically, Betsy Marie Kondo’ed my ass.

Just like having a friend come organize your closet or office can feel so relaxing and freeing and easier than tackling it yourself, having to explain to Betsy WHY I worked all the these jobs, what my current schedule was, how I thought the book could fit in, showed me both areas where I could optimize and also where my initial choices weren’t sound. I now only meet with people on Wednesdays or Fridays, for example, because commuting around for meetings (I work from home) even if they were great, was taking big chunks out of my days each week and preventing me from getting into the flow state I needed to write so much on such a tight deadline.

Same with teaching – she had me move the bulk of it to the top of the week, so if something came up later, I didn’t have a large, deadline-based, high—labor thing to do in the second half of the week. She would ask me WHY I was doing something a certain way, and if I didn’t have a strong reason, we would discuss whether there were better options. Electronic scheduling and task managing feels stressful to me, so we went to a pen and paper method. Knowing that I couldn’t take a meeting on a Monday because that’s when I did student feedback meant that if someone could only meet that day, I just said no rather than hustle to try and adjust my schedule.

Coaching to me feels like creating some hard and fast rules of my work flow so that I didn’t have to consider every single decision from all angles, which takes a lot of mental energy. The same way I didn’t argue with my swimming coach about the benefits of a certain set on my training, I didn’t argue with Betsy about the benefits of creating more of a structure – the power of coaching is giving yourself up to the instruction and guidance of someone else!

6.  What advice do you have for anyone struggling with their careers?

For me, so much of my career changed at two key moments – 1) when I specialized. I went from a general comedy writer to someone specializing in satire, to the point that I taught it, wrote it, and created a website featuring it. Once people could see I had become a specialist with highly honed skills, I started to get much more widely known and sought out for that skill. I think there is value in dabbling for years when you first start, but then I think pulling in and getting very, very good at 1-2 things can be very beneficial.

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The second moment was seeking out collaborators and realizing I no longer wanted to work alone most of the time. When I was younger, I wanted all the glory myself, and I wanted to write the way I wanted to write without outside feedback. I do think that’s key to developing a voice as a younger writer or artist. But as I got older and more experienced, I wanted to work with people who had the same goals and work ethic as me and use our collective powers to rise together. Starting The Belladonna with Brooke, Carrie, and Fiona, writing with them, and realizing that we had the same desire to open pathways for other writers has galvanized me in new ways. When I’m exhausted and need to drop the ball, they can pick it up for me, and vice versa. I don’t think I would have ever written a book like this or started a site alone – it was their partnership that made it seem feasible to me. We say a version of this to our Belladonna contributors as well – we can go further and farther and faster together, as a group, than we each can on our own.

7.  Anything else you would like to share with us about yourself or your career?

I’ve said to Betsy before, my career has sometimes felt like I’m walking forward in the dark, one hand in front of me feeling for obstacles, not sure where I’m going. But things keep panning out! For a long time I thought because I couldn’t visualize a long term goal, there was something wrong with me and I didn’t know what I was doing. But I feel confident now that I’m creating the career that I want and that works for me, and there might not actually be a clear path that I can see in front of me to know every next step. As a Type-A maniac, it was scary to give myself over to that. But this year and New Erotica for Feminists has shown me that the best things in your career can emerge fast and furious, and you can shuffle your life around to make room for them in a way that honors the other elements of your life (health, family, relationships).

There’s feast and famine in any creative career. I’ve always been good at getting through the famine periods – writing on my own, learning new skills, creating things like The Belladonna, etc. This was my first feast period when I had to turn things down and really define what meaningful work is to me. I’m very, very happy to have learned skills and tools to deal with this side of things! Please follow me on Twitter @Kunkeltron, check out my workshops and writing on my website, and check out the book on Instagram @neweroticaforfeminists and consider buying a copy or requesting it from your local library. One thing I’ve never had a hard time with is promoting myself :)