Chrissy Rutherford on Vulnerable Leadership

Last week, I had the pleasure of sitting down with Chrissy Rutherford for a conversation on vulnerable leadership, the importance of truth, and how to meet yourself where you are.

I’ve been a longtime fan of Chrissy’s newsletter, FWD JOY, and she’s given me so much inspiration and confidence to share my own stories more honestly through Brightsiding. Chatting with her was an incredibly full-circle moment. Catch the full convo on the podcast right here!

XO
Erica

This interview has been shortened and condensed. Listen to the full conversation on my podcast.

EB: What does vulnerable leadership mean to you? 

CR:  Leading with your heart. It's so innate for me that there's not even much effort I have to put into how I operate or think about my newsletter. All these stories have just always been inside of me. They've always been stories that I wanted to tell about myself, even though some of them are really actually quite difficult. I have to question myself before I even hit send … like, do I really want to put this out into the world? Do I really want people to know these intimate things about me that I've felt shame and embarrassment around? 

But I think it's really important for us to see those struggles that other people go through because I think we all kind of think that we're the only ones to have ever experienced the things we've experienced and it's usually not true.

If I'm the first one to put my hand on the hot stove, it's like, I'll, I'll do it for the good of everyone else. I think I also have a level of detachment from the stories I'm sharing. And look, I'm almost like four years into this. So it's like, I'm kind of caught up. There were some like major bombs that I was sitting on and [by now] I've put them all out there. 

I'm not interested in being super reactive when I'm struggling with something for an audience. That is so, so not my style. Honestly, sometimes I find it to be a bit irresponsible. I'd much rather experience something, sit with it, process it, journal it, do all the things. And when I can find my equilibrium again, okay, then it's time for me to talk about it. But I'm not, yeah, I'm not really willing to put it all out there before I've really been able to sit with it.

EB: Was there a moment in your career that pushed you into this space, and encouraged you to lead with vulnerability? 

CR: You know, I think a huge catalyst for all of this (including starting this newsletter) was an essay I wrote when I worked at Bazaar about overcoming my chronic anxiety. Of course, you're never over it – it's a lifelong journey. I was really scared when that essay got published. You always have to hold both truths, right? I just knew that it was an important story to tell, but at the same time, I was definitely scared because it was something that I held so close to me for so long. And so I was like, my God, people I went to high school with or college with are gonna read this and think that I'm crazy. 

The response was so overwhelmingly positive that it really just made me realize like there's not enough stories like this. There's not enough examples of people like really being open about their experiences with anxiety and mental health struggles. 

So that's why ultimately I was like, okay, I'm gonna start a newsletter. I don't know that I like really knew where I was going with it… I knew I had some stories, but there was a part of me that's quite shocked that almost four years later I'm still doing.

Erica: I felt the exact same way when I sent out my first Brightside. It was December of 2019. I literally sent an email from a Gmail account to 12 of my close girlfriends. And it was just so like experimental and silly at the time. And now it's turned into my career and it's amazing and surprising to see that all unfold. 

Let’s talk about “being online.” How do you manage boundaries? Is there a difference between online Chrissy and personal Chrissy?

CR: I don't think so. I think I'm very much like what you see is what you get. I'm not sharing anything that I'm worried people are gonna use against me. It’s like that saying “whatever anybody is going to say about you...  I've already said it to myself.” So in many ways, I actually feel like by sharing some of these more difficult things I've struggled with I’ve actually set myself free. 

Like, I'm an adult and I've never been in a serious, like long-term relationship. For a long time, that was like a deep, dark secret of mine. 10 years ago, I don't think I ever would have imagined sharing that. Like my God, it was so uncomfortable. And now having shared that, I'm like, what are people gonna say? 

And sure, do I think about the ways that people might hypothesize of what's wrong with me? I've already thought about that as well. I talk about that in therapy. And also I'm at a place where I'm am so… aware of all the factors that have contributed to that. So I don't know. It's like, you really can't hurt me with that at all.

EB: Totally. My friend Holly has a great saying. She says, I have already swam to the bottom of that lake. And I agree that it does get easier. And the truth can be so freeing. 

Let’s talk about that, actually. Truth requires being able to see situations from all angles, even angles that are maybe very uncomfortable or have you confronting like a shadow side or things that feel somewhat shameful.

I'm curious about your relationship to truth. For me, it's taken a long time to kind of step into truth because it required stepping out of a victim narrative that kept me safe in a way. It's taken a lot of growing up to be like, actually this is what I'm accountable for. And to see the truth in the objective like facts of the situation. What has your experience been? 

CR: I think I'm a bit obsessed with the truth. One of my biggest pet peeves is like people who can't be straightforward and like say what they mean and mean what they say.

I think I had an issue in my twenties with actually being a bit too honest to the point of like hurting others. so learning a bit more tact around that was imperative. I feel like my dad set a very bad example for me because my dad is like, just says whatever's on his mind. He doesn't really care about hurting people’s feelings. I’ve had to learn how to not hurt people's feelings. So that was important. You know, and you're just like, well, I'm just being honest. God, it's terrible, terrible way to be. 

I just feel like the truth is so important. Also, I grew up in a family where it was like, just easier to ignore the truth or to sweep it under the rug or whatever. And I was (and still am) the only one who ever wants to confront things head on.

So yeah, in a way my family kind of pushed that obsession and I developed this sense of “you're not gonna keep things from me.” 

I've also taken that approach to my newsletter and just like who I am and how I show up like. I have certain friends who are like, I know you're always going to tell me the truth and what I think about something, what I think about their outfit or, you know, silly little things. And it's like, it's true. Like, it's really important to me.

EB: Yeah, and it's such a gift to be able to access the truth and share it with others and do it in a way that still has compassion and tact. I feel like I'm learning to step into my truth more, but I certainly have friends who are like gonna give it to me so straight no matter if I'm ready for it or not. I think I've come to really like value and appreciate those friends for that, but it’s definitely taken a lot of work on my own part to let that in and take it at face value and say “okay, great, how do I move on from here?” 

What has your self-discovery process looked like? When did you start to turn the introspection light on and really get in touch with your values? 

CR: I've always been deeply introspective. I’ve been a journaler since third grade, writing about my crushes or whatever was on my mind. I've always been curious about what's going on inside of my head and why I see the world the way I see it. But we only know what we know when we know it. 

I've been in and out of therapy since I was 11 years old. I've taken big breaks at various times, but more consistently, I would say I've been in therapy since 24 or 25. In my twenties, I thought I knew so much. But again, you only know what you know. So now to be where I am now, I'm like, holy shit. 

Sometimes, I'm hard on myself because I'm like, why couldn't I have gotten here sooner? That is such a terrible headspace to be in. I get there every once in a while and I'm like, no, because It's all part of the journey. 

I also I went through a pretty rapid transformation starting at 30 during my Saturn return. I wrote an essay about this for my newsletter about how it's called “I traded my therapist for a tarot reader” which was basically because of this situationship I had been in on and off. It makes absolutely no sense to me now when I reflect back on it… but I was just down so, so badly for this guy who I think was interested in me but did not have the emotional capacity whatsoever to go anywhere with me. 

In many ways, I like broke my own heart over him because I spent so much time chasing someone who was not interested in having a real relationship with me. And so when it all finally fell apart, it just all like blew up in my face so like magnificently that I was then forced to confront it and ask … how did I get here? Why did I do this? Like, why was I giving so much of myself to someone who didn't want what I was trying to give them? 

Then I found this tarot reader randomly and the journey really started there. He really saw and reflected what I was going through. And he had given me two books to read. One was The Places That Scare You by Pema Chodron. It is fucking incredible book. If you are going through a hard time, whether it's a heartbreak career or whatever, it's a great book to read. And I come back to it very often - and also Living Beautifully by Pema Chodron. 

And yeah, it's like layer by layer, I just started to unpack what was going on with me. I think also coming to understand what attachment styles were. I am absolutely guilty of pathologizing my attachment style and wearing it like a personality. I have since been able to course correct over the last couple of years, but Attached by Amir Lavigne, that book blew my fucking mind. It made me break up with one of my therapists because I like, I knew my parents' relationship and how they interacted with me like affected my relationship. But this book lays it out all so clearly. I was like, I'm not crazy. I just have anxious attachment. I'm not crazy. Like that was my first takeaway from it.

EB: This is all soooo relatable. This isn’t easy work, and it’s a long winding road. What advice would you give someone who is just starting out with their own introspection journey?

CR: No, it's not. And you should know that upfront. Like this is not easy. It's why a lot of people won't do it; it's not fun to self-examine. It's gonna make you feel really uncomfortable like quite often. But like, it's so fucking rewarding. It is so incredibly rewarding.

I don't know. think my best advice is like get a journal and use it often. It's so strange to me when people are like, “what journal prompts do you use?” Like, I just write and I never look back. And that's another thing. Don't edit yourself. There's nobody but you. 

I'm lucky if I can even go back and read my own handwriting because I'm writing so like furiously on the paper. Just write, just write what's in your head, write your deepest, darkest thoughts that you're scared of. Sometimes I find myself avoiding journaling because I'm scared of what I'm gonna put on the paper. That's when you need it the most.

I mean, sure. If you really feel like you need help, get a guided journal. They exist for a reason, but literally you can just write what happened to you today. Write about what's making you happy. What's making you sad? What do you feel like you're struggling with? What do you want to get better at? How are your friendships making you feel? How is your family making you feel? 

If you're a human, you've got endless material to work with. It's difficult to be an adult. I mean, sorry, it's difficult to be a human.

EB: Yes. I say that all the time. And if you, I feel like I meet people who don't understand what I say when I say that. I'm like, that means we're on like very different, very different levels. 

Tune into the podcast for more wisdom from Chrissy - and answers to some fun questions including her favorite thing about her life right now, her “don’t let me buy this”, and more.

Dopamine was FLOODING my system when I saw this planner at McNally Jackson the other day … but I was a good girl and reminded myself that I have three other planners at home, so I passed. But Next Chapter Press, you have a new fan!!