As told to Loré Yessuff, 2227 words.
Tags: Podcasts, Writing, Money, Success, Mental health, Day jobs, Failure, Inspiration, Creative anxiety.
On slowing down and showing upPodcaster and writer Katie Dalebout on finding a healthy life/work balance, the positive value of journaling, her ongoing battle with imposter syndrome, and readjusting our notions of success.
So much of the creative world can be so competitive, and toxic, and based on a mindset of scarcity. I’m wondering how you balance wanting to be everyone’s cheerleader and fighting that comparison sickness that we all get into sometimes.
I’m the least competitive person that you’ll ever meet. I was never competitive in sports or school or any of that. When I started the podcast, I was quite young. I was 22. And podcasting was not what it is now. It was just an excuse for me to be able to talk to people who I admired, people who I put on a pedestal, and get an hour of their time and ask them whatever I was curious about. Now, I consider the audience more than I did, but I’m never going to be an expert. I’m just letting my career be what it is and following what is working instead of being bummed about what isn’t. I try to focus on the people listening, not how many aren’t.
It’s a daily practice, right? It’s so easy to tell yourself those ideas, but then to actually digest and integrate them is another thing. What are some of the biggest challenges you’ve experienced with freelancing?
I want to be really honest. When I graduated college, I had this blog and it was like 2012, peak internet, peak blogging. All I wanted to do was teach yoga and blog, but I also wanted to be able to support myself. So I got a full-time job and I worked in marketing for this company. I was so nervous that working full-time would take me away from my creative work, so I was diligent about being a freelancer on the side of this full-time job. I started the podcast after I had that job. I wrote my book, went on a book tour, all while I worked that job. For six years I did all this stuff on the side, and I saved money and I didn’t have to put pressure on my creative work… I think if I had a higher uncertainty threshold back then I could’ve done freelance, but I didn’t. I didn’t have any models for freelance in my life. I didn’t know any entrepreneurs. My parents have both worked full-time jobs with insurance, so I just thought that’s what I had to do. And for me, I guess it was for a while. I feel like I missed my 20s because I was working a lot. But the reason I’m able to do a lot of what I’m doing now is because I have savings.
I really appreciate that you’re being so transparent, because money is often such a mystery. It can be disheartening when you people say, “you should freelance full-time.” But then don’t share their financial situation.
Yes. I agree. And who knows. I might have a full-time job again in a year. I don’t know what’s going to happen with this. This whole thing might blow up. I don’t know. I hope not. But also, it would be fine. I would figure it out. But when I was in my full-time job, I had this fear that I don’t think is true, but I was like, “Well I’m not a real writer. I’m not a real podcaster because I don’t make my money doing that.”
And I still feel that way, even though I don’t have a full-time job. But I’m like, “I’m not a real podcaster,” because I also do workshops, or I’m not a real work shopper, because I also do these podcasts, or I’m not a writer because I do a bunch of things. But our work is not our identity, and that’s something that I’m really wanting to take on.
I had some friends with big projects I admired tell me their parents gave them money to start them. I said, “I was happy to know that.” You never know who’s supported by their family, or supported by a partner. And I don’t judge people who are, it’s great and just helpful to know. People might look at my work and be like, “she must be doing well.” But I just worked a full-time job and saved and I have low overhead.
Money can be a tough thing for people to talk about. But I really wish people, including myself, were more upfront about it. Some people have more access to resources, some people have less. That doesn’t invalidate anyone’s art. But the transparency could be really helpful. Whenever you were working your full-time job, how did you balance working your full-time job and doing the creative work that you were doing?
I did a really, really bad job. I think my relationships really suffered. I didn’t have much of a personal life. Every second was measured, and I didn’t really have friends. It’s a time I look back on that feels kind of dark and boring and hard. There were of course good moments, and I did make friends and I did do some things, but it was really… It was not my favorite time in my life, and it was my 20s. It was from 22 to 26. I was just working a lot. I was also… I don’t know if this relevant. But I have had just years of eating disorders. And it was a time when I was really in my eating disorder too, and so it was like I was really controlled and dogmatic and everything was in this certain way.
Moving to New York really helped, because I was so happy to be there and started to really loosen the reins and care more about people than work. When I was in New York, it was kinetic, really moving, really fast.
Eventually, I decided I will never prioritize work, or my body looking a certain way, or these arbitrary things that don’t matter, above people. And I remember my mom left me a voicemail during that time because I was just like “fuck, I think I’ve ruined my life by having my priorities wrong.” And she said to me, “the work will always be there, but the people might not be.” And that has stuck with me. I feel like I went way too far in the other direction, I over-corrected this summer where I was so loose and chaotic. And now I feel like I’m coming back to center in a better way.
How do you define success and failure?
I think success is keeping going after a bunch of failures and I heard this once on a podcast in like 2012, and I don’t remember whose quote this is, but he said something like fail fast. I think if you can fail quickly and get to the learning part, that that is a success, you know? The way I define success for myself is being really present with each thing you do, not just creatively, but also for your mental health. So then you can bring your most mindful creative mind to everything.
If I have a day when I feel like I’m easily bouncing between things, it feels really good. And if I have a day when I feel really overwhelmed and have too much on my plate, I can’t show up fully. That’s the only way I define failure and success as, you know, mindfulness and presence and showing up.
I like your definition of it being something that’s simple and a little less tied to like a certain accomplishment or a certain stage in our life. Do you rely on any routines? What are some of your favorites?
A close friend of mine happens to be a therapist. She and I were just talking about morning routines recently—how your morning routine can feel like a prison. I actually wrote an essay about this too. My morning routine used to be like a mile long. It was really rigid and dogmatic. I had to meditate. I had to have lemon water. I had to exercise and then do morning pages. And it was just this very rigid, controlling thing. Traveling really got me out of that. It was good for me to go off balance.
To answer your original question, the biggest one for me is walking. It’s a good one for me because I’m such a talker. So I love walking with other people and talking, and I love listening to people talking while I’m walking. I edit my podcast while I’m walking. I’ll stop and I’ll write what I want to cut into my notes. And then I’ll walk and listen more. It feels like I’m doing what the people who listen to the podcast might do, I’m consuming it like they would be consuming it.
And also journaling. I do morning pages, a version of that every day.
I’m glad you brought that up because like segues into the next question, which is what draws you to the journaling practice?
I wrote this book about journaling that came out in 2016. I started writing it when I was 24 and I’m about to be 31. And my work is still related to topics in the book, but 24 to 31 is like a big jump. I was really into wellness at the time and wellness culture, things that I now see as classist. Wellness has become a class system, there are good things in it, but I think it’s quite problematic and has been hijacked by the diet industry. A lot of the things that I say in that book, I’m sure I would change now. I would also definitely change the cover and how it looks, but I am so happy it exists. I’m happy that of all the things I was into during my early twenties, the one that rose to the top was writing for emotional wellness.
My favorite part about writing is that anybody can do it. You can do it anywhere. You don’t need anything for it. It’s a gentle practice. It allows you to skim the scum off the top of the pond in your mind, and let out your fears and neuroses and worries. Your lofty goals and big dreams and ideas— you can put them somewhere and collect them. It’s an organizing system for our brains and, you know, there’s so much research about it. It’s just a really effective tool for mental health. And journaling slows you down. I think that any practice that slows us down is probably good for us.
Katie Dalebout Recommends:
Voice texts — It’s quicker for me to communicate speaking than writing. I’m in these long voice text exchanges with friends all over the world. We chat when we both have the space for it, without having to think about timezones or schedules. For me, it’s usually while I’m walking or in the bath.
Picnic meals — Once a week my friends have what they call a “picnic meal” which is how I eat pretty often. It’s a platter of things…think tinned fish or smoked salmon, sliced carrots, berries, dips, hunks of bread, avocado, and maybe wine.
Working one day a week at a shop in my neighborhood — I met one of the six owners when I was going in during the beginning of the pandemic. I was in LA unexpectedly. Since I was new and without a car, I really stayed in my small neighborhood and got to know it well. Working in this shop every Thursday feels like a little party I get to host. Most of my friends have come to visit me or come every week. It gives my week a little structure as a freelancer. The shop is called Sip Snack in Highland Park. I do their Instagram sometimes, too.
Extremely long walks — While walking, I listen to podcasts, audiobooks, music, or talk on the phone but mostly I send and answer voice texts. I go on a weirdly long walk every morning with coffee and I’ll stop to answer work emails or listen back to my podcast episodes, so it is often a productive work walk. Other times, I go on what my friend Zoë calls “noticing walks” where I just look at what’s around me. I’ll walk with my friend Christine in her neighborhood and that has been some of our best conversations.
Close close close chosen family friendships — Kayleen Schaefer’s book Text Me When You Get Home is the best book I know about female friendship. It articulated the closeness I feel for my female friendships. Moving to LA was unexpected but I have a community now that I love and my friends back in NYC or other places are still a huge part of my life. There have been ups and downs, and moments where I’ve felt disconnected but now I feel, supported, connected, and close with my friends around me. It feels like I got closer to my friends here quicker than I did with older friends, maybe nothing bonds people like living through a global pandemic, like spending every holiday together and unpacking the wildness of this year.