Ep 9 - The Privileged CEO

Hiring an assistant and several contractors to help you in your business is the dream, right? More hands allow you to delegate tasks like a boss and focus on what you really need to accomplish to move the business forward. But what if it's harder than it seems? What if you have to come up against your own feelings of being privileged or bourgeoisie?

That's what Shannon is up against this week on ArtistCEO - how to reframe the guilt around delegation and create space for herself to become a true leader.


Shannon: Is it okay to hand off to your executive assistant calling your mechanic? And finding out what you should do about your decapitated driver’s side mirror.

Kerri: Hi, It’s Kerri. The content strategist and host of ArtistCEO. This week on ArtistCEO, we’re falling into the experience of making space. What happens when a sensitive, thoughtful overworked, and almost burnt out CEO needs to delegate? Here’s Shannon.

Shannon: Or asking her to make a call to a coworking space to find out what kind of wifi speed they have for when I want to try out working there on Wednesday to see if this remote working situation is going to work when I know that it would just take 5 minutes online or even just calling them myself. Is it okay to hand off things I know I can do, would take me almost no time to do them that don’t free me up much in terms of time, but do in terms of space? And especially mental space, emotional space, psychological space. That’s what I feel the issue of the day is where I’m having to face my own sense of, guilt, I guess, and feeling overly privileged and entitled, which is an ongoing thing that you don’t hear a lot about in business. And maybe that’s because there’s a whole bunch of people who they just know that’s what they have to do and maybe they’re better at being CEOs than I am, but here I learn.

Kerri: Or you might be like me and are just a control freak that can’t let things go. I’m working on it.

Shannon: I also think that it’s a female tendency to feel like, “Well I know I can do this so why burden someone else with it even if I’m paying them and it’s their job to do so.” I think women are really good multi-taskers and we’re used to taking care of the small things in the background and why bother handing it off it it’s really no big deal? But that’s the whole thing, it’s all the little things that are no big deal, that if you don’t hand them off become a very big deal because then you don’t have the hands and the space to deal with the things that are really big. Like a client call that only you can handle.

Kerri: So Shannon commits to start handing off more of the little things to make room for the big things. She starts by clearing out a Sunday so she can have some time to just be - and some time to think.

I’m going to tell you now that this episode is going to be a little different. It’s more...meditative? I just loved listening to Shannon work through this so much and tell this story that, I wanted to give you a deeper peek inside her mind.

Shannon: Oh my god it was so nice, I had Sunday OFF. I mean, I had work to do, there’s always work to do, but I had Sunday off in that there was nothing I had to do...and I almost didn’t know what to do with myself. I hit a bout of depression early in the morning because I was like, I have all this time to exercise and do yoga and write and think and I didn’t even know what to do first, so I actually ended up sitting on my butt for a good portion of the morning, just sipping tea and zoning out and fighting the impulse to check my email and start checking things off in Asana. But instead I waded through it, I persevered and even though I skipped the morning dance class I was going to go to, I did decide I was going to give myself a significant amount of space to do a trivial little task. But it was an enjoyable little task and it was something I knew I couldn’t hand off because I had to physically be there, I had to go find some new running shoes. So I walked there, I didn’t drive there, I took my time, when the register didn’t work when they were trying to ring me up and they kept trying to start it again and again, she was getting really flustered the woman behind the register and I was just like, “Its okay.” Today I have a lot of space and if it takes me 2, 2 ½ hours to buy tennis shoes, so be it.

And it was because I had intentionally decided to hold that space and to carve out that space and try to not shove in a bunch of activities, even if those activities were for self-care. Like I’m gonna wake up, go to exercise, do my home yoga, sit on my zafu, meditate, then load the dishwasher and the washing machine because I’d like to do my own housework every once in awhile, but I didn’t. I just got new tennis shoes and it took me the afternoon, but it was nice, it was enjoyable. I got to walk in the sun and I ended up walking over to Whole Foods…

Kerri: If you are really busy right now, I’m sorry but this section is going to annoy you. What I recommend is imagining that you are in the sunlight with Shannon now, it’s a Sunday, you have lots of space and you’ve just bought yourself your favorite artisanal beverage that is at least $2 more expensive than it should be. You know the one I’m talking about. Enjoy.

Shannon: And I have to say they have very good espresso and I got myself a bottle of coconut milk from Whole Foods and then I sat outside in the sun with my sunglasses and hat and poured that coconut into my espresso and made myself a wonderful little coffee drink and I sat and I wrote all the tasks I do in this business. Some of the things were just a brain dump, getting it out of my head, things I would hand off normally. - Call this person, check on this thing, do a little research on this topic and I wrote those things down just to get them out of my head. And then I also walked myself through the process of a normal day and normal week and thought, What are the kinds of responsibilities that are on my plate? And a lot of them are things that currently I do and it would take some training to have someone else do them, but I think it’s totally possible that someone other than me do it and even fairly soon, with my current team I could do a little bit of explaining, impart a bit of information and for a week they can handle it and it would be fine and nothing would go to hell in a hand basket and my business, unless something totally out of the blue happened would probably keep on running without me - for just a week.

And I realize how much of my identity is tied of up in this sense of importance, because it’s true - I built this business, I built this team and without me I think there would be a significant lack of center of gravity holding it all together. But that’s not to say that I’m absolutely needed all the time, even if I’m necessary.

I think that what I’ve created at this point has enough momentum and the team that I’ve created has enough cohesion and information and skill to be able to make pretty good decisions without me. And yes there’s a certain level of expertise that at this point I just can’t hand off. Until I get someone much more senior at a brand strategy and management level, I think it’s going to be me for while. But writing out this list while sitting in the gorgeous sunshine and watching people come and go with their various whole foods shopping bags, filled to the brim with organic quinoa and collard greens, I got a more realistic picture of the things I don’t actually need to do. And there were only a couple things that I did and those things are

  1. Knowing how it all fits together

  2. A certain level of creative direction

  3. And also Vision - being able to see and guide this entity, which is now outside of me in the direction I think it can go.

That role, that visioning, what that requires is space. It doesn’t require a whole lot of skill per se, I think skill and experience definitely comes into it - but I got to see that the true value of my role, as I’m doing my job is not about productivity most of the time. It’s about space and vision and perspective. And if that’s my value and if that’s what I’m responsible for within this team - then I sure as hell better make sure that I have that space and I carve out that space and what that means is that everything else that would otherwise fill that space or that psychic room - there’s only so much furniture I can fit inside that room! It’s not just that I can, or I should hand those things off, but I must. And actually It’s a disservice to the company for me to do otherwise.

This sounds silly and I’m even afraid to say it because I have a lot of shame about sounding bougie, but I’m really trying to reframe this for myself because I think it’s absolutely necessary to find this new perspective. I am the daughter of two elementary school teachers and the granddaughter of a dairy farmer - I like to joke that I’ve been in the branding industry for four generations - aha haha. But seriously, we have a brand, a DeJong brand that they actually use to stick on cattle. But the point is, I am used to being a worker and I feel like I value rolling up sleeves and working and therefore doing oneself all of the little things in order to achieve the big things.

This sense of getting help, at first in my brand team and in my personal life, I’ve really struggled with it. I’ve really struggled with feeling privileged and bourgeoisie and spoiled and like my fingernails aren’t dirty but have high-priced manicures on them. That’s very uncomfortable for me, but I’m having to reframe away from that dichotomy because i don’t actually think any work is better or worse I just think that it’s different and we all contribute. And if we recognize that no one is more important than the rest, it feels like a true collaboration and in the organization I’m building here I want everyone to feel like that, I want everyone to feel valued and important. And not in a kitten hanging off the branch “Hang in There!” cheesy 1980s corporate posters sort of way, but truly. If any one of those people were missing, we would all feel it. And the entity, the organism of the company itself would suffer.

I don’t know if this is a bunch of bullshit or not, you tell me! But it’s just where I’m at in my process. And I feel really strongly and I becoming ever-more passionate about learning what it takes to be a good leader and what does it take to be a good CEO and creative director. Those are my roles, that’s what the company is paying me to do and I take that responsibility very seriously. I want to honor the work that everybody puts in and I want to honor the work that I put in. And If I’m being absolutely neutral and totally unemotional, I realize that it’s actually my duty to hand things off and it’s disempowering to my executive assistant, to my project manager, to my creative team, to my finance director, bookkeeper - If I try to micromanage those tasks by thinking it’s my job to do them -  that’s disempowering to them. It’s saying, “Oh no you can’t handle your job, so I’m going to do 50% of you job and 100% of my job.” Which by the way, if I’m doing 50% of your job, I’m not doing my job at 100% capacity.

So, fuck it. Here I go handing off every single thing that I can and realize that in doing so I’m serving my team, my company and yes, I’m serving myself. Because I am determined to be a motherfucking badass spirit in a CEO human body - to birth this creation and this company into the world that I know is possible. Because I believe in it, I believe in it’s mission and it’s creative gifts. And part of it is that just as an artist would ruthlessly defend their space so they can facilitate, cultivate and foster the quietest, deepest, most mystical parts of the creative process, so must I, in my professional life - hold space. I must create boundaries, I must hold to those boundaries, and I must, with eyes on the horizon and feet deeply rooted and heart radiating open and gut, simple, but sharp - I must declare “This is my space. This is my space. And my solitude and my quietude and my truth. And from here - no rush, no pressure, no stress. From here - is where I am most powerful. From here is where I will be of greatest service to this world.

Kerri: So there you have it. Shannon has her “Why” behind delegation and creating space. Do you? Next time on ArtistCEO you’ll hear more from Amanda Peterson on valuing your work as an artist and a creative professional.

ArtistCEO is an Arthouse of Who Production, a division of House of Who, Inc. Find out more at www.houseofwho.com. Subscribe to our newsletter at helloartistceo.com to get a heads up when the next episode releases. Music is by cf watkins at cfwatkins.com. My name is Kerri Lowe, you're listening to the story of Shannon DeJong. Signing off.

Kerri Lowe