Sheryl O'Loughlin

The heart, I think, is so essential, but that’s the thing that, many times, gets lost.

Peter: This is going to sound like a strange question, but why is that important? Meaning, if you’re running a business and there’s a bottom line to it and you can think rationally and strategically about your next moves and you make those next moves, why is the heart an important piece of it?

Sheryl: I think one of the things that we have lost over time, and that there’s many business now that are starting to bring back, because quite frankly, millennials are demanding it, is that there’s human beings in these companies. We forget that. They’re people with lives that have emotions, and we’ve so much separated business where everything’s just about keeping thing at arms length and thinking through logically, and decisions.

What we’ve forgotten is that people are still at the end of that. What I’ve realized is, when I haven’t kept myself, my whole self, as part of this, my head, my heart, my spirit, I leave my people lost and that I no longer have that connection as a leader with them.

I think it is so critical to be able to stay connected with our teams and really provide purpose and meaning in our work.

Peter: I want to reflect back to you what I read in your writing which extends what you’re saying one step further, and which I agree with, and that’s that you’re not just doing it for them, for the employees, but you’re doing it for yourself, meaning, if you’re going to continue to be a powerful, present leader, to the internal world, to the external world, it’s not just showing up in that so that you don’t lose them. It’s showing up in that way so you don’t lose yourself, which is something that I think comes out loud and clear in the writing, and the struggles, frankly, that you’ve had as you’ve run the companies.

Sheryl: Yeah. I think that, taking a step back from it, we have created this culture around entrepreneurship that is all about how great everything is all the time, and we, as entrepreneurs, we need to many times be like, “Everything’s great,” because if we don’t believe it, nobody else around us will. We’ve got to bring investors on board and suppliers and employees to join our team, and we’ve got to be out there, positive about this journey, but there has to be a time where we can take a step back and talk to other people and get the support we need to say, “I’m worried. I’m scared. I feel like I’m falling apart. I can’t sleep at night.”

You talk to so many entrepreneurs who have been through this journey, and they will all say, “That was hell. That was going through hell and back,” but no one talks about it as a part of the process and even the media … I’m so grateful that you’re doing this, because even the media doesn’t give us that impression, that anything is hard, because it’s all about the money and the success.

Peter: Right.

Sheryl: What so many entrepreneurs are going through is they have lost themselves in the process, and experiencing things like depression, and bipolar disorder is highly associated with entrepreneurs, and drug abuse, and we hear all the callings of alcoholism, and suicide and divorce. It’s because you’re in such an intense situation and if you’re not keeping yourself grounded as part of it, it will take you away.

Peter: One of the things that I hear from people when I have this conversation with them, and this is especially true of women, who are leaders in organizations that I have conversations with, which is, “I can’t openly say that I’m scared. I can’t openly say that I’m feeling out of control. People will lose faith in me. I will lose credibility. That kind of vulnerability risks my power and my leadership, especially as a woman in an organization,” though, I think it’s true that men feel that in organizations, also.

I wonder, as a woman who is a leader, who is a CEO, who’s run several companies, how do you respond to that? How do you address that concern, which feels very real?

Sheryl: In some ways, I want to answer that question in two different ways. One is where I think the envelope is pushing out, in terms of more progressive companies. I would like to go back there after, so I want to stay really grounded in where many people probably are right now in exactly what you stated.

There is a time and a place to be vulnerable. It can’t be that, if you’re in the middle of a crisis, and you’re absolutely falling apart in the moment, to go up in front of your whole company and say, “I am in the middle of the crisis. I haven’t figured it out. I’m completely falling apart.”

That’s going to scare a lot of people. I think there’s different ways to approach this. One is to make sure that you’re finding people, a tribe of people, that you can be vulnerable with, that you can open up to to be able to get that support, and there’s many organizations like that, there’s starting to be many, that are out there, whether it be the Entrepreneurs Organization or Young Presidents Organization, YPO, or even just finding a group of entrepreneurs that you feel like you can open up to and that can support you.

You need to have that so that you can think through, “Okay. How can I get grounded again so I can go in front of my team and be able to say, ‘Hey guys. I’m going through a rough time here. Going through a rough patch, but I want to let you know I’m here with you, I’m focused on being with you, but I need to let you know I’m feeling this way because you’re going to see it.'”

I think that’s the thing that we forget in our companies, is that people see it. They know it. When we’re walking through our companies and we’re completely shaken up by things that are going on, they take those signals for the leader. Without acknowledging them, we’re making it so it becomes scary.

I’ll give you an example of something that just happened today. I was dealing with a little bit of a crisis in our marketing group, and it was pretty intense, and then I went into this meeting that, ironically, was on our culture committee. It was a committee of people who works on, “How do we continuously improve our culture?”

It was about five minutes into the conversation, and I realized, I have been really intense, because I’m thinking about this other conversation, so I reeled back to them and I said, “Look, I’m really sorry guys. I am just coming off of a very intense conversation, and I know I’m bringing it into this one. Let me dial this back and take a deep breath and start over.”

It’s acknowledging what’s happening with you in the moment, and making it so that people understand what’s happening, and then making sure that you’re coming down and grounding yourself again.

Peter: That actually takes strength. In effect, what that communicates is, “I’m not weak. I’m strong. I’m willing to admit what’s going on for me that’s getting in the way, and I’m willing to correct it.” The asset in that situation is you were able to correct it in the moment, which is great, because that shows an incredible amount of groundedness and strength.

I think the challenge people have, that I talk to, is when they’re feeling that out of control, and they don’t know exactly how to correct it yet, so they’re in the middle of it, and it’s in that middle of it that feels really scary, and maybe the truth is, when they’re in the middle of it, they don’t share it broadly. They find their small tribe. They find people who they can share it with, until they feel like they’ve gotten their ground enough to be able to come out more publicly, and course correct in that way.

Sheryl: Yes. I think there’s a difference between letting it all out and who you let it all out with, and coming to terms with it, and what you are presenting every day in the company. In other words, when I was going through, and we can talk about this, some of the struggles that I had, it took a very long period of time to be able to come to grips with what was happening with me and to be able to even figure out how I was going to approach it myself.

Peter: Let’s be specific, because you’re right about it, and it will help listeners who haven’t read the book yet, to have a sense.

Sheryl: When I was at Plum … We can dialogue a little bit about the story, Peter, and tell me where you want me to go more in depth and less in depth. I had co-founded a company called Plum, and it was … It came after I was leading Clif Bar and it was all about nourishing kids from the high chair to the lunch box.

It was a company I co-founded with somebody, a guy that I had worked with … Hired, over at Clif Bar, brilliant product innovator named Neil Grimmer. We were both so passionate about feeding our kids healthy and organic and doing it in a way that it was great tasting and well-designed food.

I’m going into this thing, starting a company from scratch, and funded by VCs right from the beginning, and going through the typical ups and downs that you go through, everything from seeing your products out there in the world, which is a great high, to manufacturing problems where you can’t even get the product off the line to be even able to ship it to customers, so ups and downs.

At the same time, my husband decided to start a business, to, and his was called Blue Sky Family Club, and why we ever decided to do this at the exact same time, I will never fully understand. Warning to readers: not smart with your significant other to start a business at the same time.

The idea was great. Blue Sky was this indoor play space for kids where kids could eat healthy and do physical activities and creative activities, and parents could have a glass of wine or a beer. Every parent drooled over the concepts.

Peter: Let’s fast forward a little bit, because his concept failed.

Sheryl: His concept failed big time. The whole thing blue up in such a short period of time, and it was all self-funded, plus a lot of debt. We almost went personally bankrupt. We lost everything we had, every single penny we had. We moved immediately out of our house, had to sell it, and it wasn’t until a year ago, eight years after we closed the doors, that we finished the rest of paying off our SBA loan, and it was super intense and super stressful.

Then there went to the way I dealt with that. I started running and running a lot, and I felt like, “Wow, if I’m out here on the road it’s kind of clearing my head. I’m not hearing all the debt collectors calling,” and it was just my space, so very healthy in terms of the idea to begin with. What started to happen is, I would run more, and then every day I would run more than that, and I was up to … I was running hours every day.

Peter: The idea is, in some ways, you had no control in so many different aspects of your life, here was an aspect of your life that you could have control over, and you could have control over what you ate and how you exercised, and it led to the extreme, eventually, of anorexia.

Sheryl: That’s right. Yeah. The scale … I could control those numbers even though nothing else was in control.

Peter: Right. Were you able, in those moments, to talk about it? We could talk about it now. Were you able, in those moments, to speak about it? Did you know what was going on? Were you able to see it?

Sheryl: I didn’t. I didn’t know what was going on. What I felt like is it was such an out of body experience. I couldn’t think. I didn’t have the energy to think, and literally, I felt like, “I can not run this company anymore,” but I didn’t fully understand what it was that I was really dealing with.

Peter: Why I think this is such an interesting question to explore is because it’s in those moments when people feel the most out of control. Once we have a grasp over it, and we know how to move forward, we’re approaching life with a certain amount of strength. When we’re in the midst of it and it’s a blind spot and we don’t exactly know what’s going on, and we know we’re losing some control, we know we’re not showing up the way we want to show up, but we don’t quite have our arms around what’s happening.

That’s such an important moment, because that’s, in my view, the most vulnerable point in our leadership, where we’re leaders, and I’ve seen people hit this in so many different ways, where we’re leaders and we’ve lost … We’re a little lost, and from that place, we have to move on and we have to ground ourselves and do that thing that you were talking about doing in the meeting.

My question is, what advice do you have, from your own experience, of moving through that space without losing everything, moving through that space to get to a place where you can get re-grounded?

Sheryl: In hindsight, one of the things I should have done was I should have said, “I need a little time off.” I should have gone and said to my team, “Hey, I got stuff going on in my life. I need to take a week, a couple weeks off, to get re-grounded, and come back to you to be the leader that I should be with you.”

Peter: I have to say, I love … Just to reflect to you, when you said, “Time off,” I was thinking, “Yeah, when someone’s at that place, they might need a year sabbatical or something,” and you’re saying, “One to two weeks,” which talks to your drive. You’re saying you didn’t need that much time. All you needed was a couple of weeks of completely separating yourself from the business to re-ground.

Sheryl: That’s right. Now, would it have fully solved it? Probably not, but it would have given me the time to slow down, to think about what was happening, and to be introspective and talk to the people that I needed to talk to, my family and friends, to be able to understand what was happening with me.

I had people telling me that something was terribly wrong, my friends and family, that I was losing too much weight, but I didn’t even take the time, and I think a lot of driven people do this, to slow down enough to be able to be reflective of that. After that one to two weeks, I might have said, “Wow, I really need some massive time off,” that you’re talking to. “I need to take a leave of absence. I can’t do this anymore right now,” or I could have come back and said, “You know what? I understand exactly what I need to do in order to resolve this. I need to see a therapist. I need to work on my nutrition, that I can come back fully into this space,” but I never did that. I never took the time to pause and understand what was happening.

Peter: It’s a powerful lesson. Really, the first step is to recognize that something’s not working, and one of the ways in which you recognize that is feedback from other people, because you might be so deep in it that you don’t recognize it, but another way that you recognize it is you have a sense. You know internally something’s not right. You don’t exactly know what it is.

You’re probably feeling a little scared. You’re probably feeling a little uncomfortable. You’re probably feeling a little depressed or unhappy, but you know that something’s not quite working, so maybe there’s a combination of an internal knowing and some external feedback from people who are close to you to say, “Something’s not right here,” but if you haven’t been able to put your arms around the whole thing and understand it and move forward, step two is to say, “I need to remove myself from the system that I’m in,” to take a pause, to take a break, to give yourself a time out, in order to create a little bit of space from what you’re experiencing and to let what’s going on sink in and settle.

Maybe have some conversations with people, to get a better grasp over what’s going on and what your next steps might be, and then step three might be, follow through on those next steps or take some more time if you haven’t figured it out.

Sheryl: That’s right. I think we’re talking about an extreme situation in this case, but regardless, I still think that being willing to be open with people and say, “Look, either I need to take some time,” or, “Hey, in this moment there’s a lot going on right now, in my personal life, in my professional life,” whatever it is, that acknowledge it, because I think it’s in those moments where we’re not acknowledging what’s happening within us that we’ve got to know that each of those moments, our whole team is seeing that. They’re experiencing it with us, and not giving voice to it makes it scary. That’s what we have to do, is give voice to it.

Peter: I think what’s scary about that for us as leaders, entrepreneurs and leaders, is that it’s hard for us to give voice to something for which we don’t have a solution. I can give voice to something and say … The example that you gave in your meeting earlier, “Sorry, I’m bringing my last meeting into this meeting. Let me take a breath. Let me reset. Great, I’m here.”

To say, in that meeting, if you said, “Look, I’m totally frustrated, annoyed, I don’t know why, but you people are bugging me, but let me try to be present anyway,” that wouldn’t land so well, in effect. The challenge, when we don’t really know what’s happening, if you don’t realize you’ve brought your last meeting into this meeting, is you’re just feeling annoyed and you don’t exactly know why, and I think that is a very, very hard place from which to operate.

Sheryl: Yes. It’s a very hard place, but you said it earlier. You know it in you. You know it in your body. Something is not feeling right, and if we’re not feeling that and paying attention to ourselves, we are going to miss it, but I still think that in that moment of saying, “I’m feeling really intense now,” to be able to ground ourselves, literally, in our chair, and stop, and take a breath, a physical breath, and say, “Guys, I am trying to get present with you. I’m feeling un-present right now. I’m trying to ground myself.”

Voice it, because when you voice it, it gets out of you. It settles with it the group so they know what’s happening, and you can restart the meeting. It doesn’t mean that you have to say, “Here’s everything going on. I’m totally frustrated with everything that’s happening.” It’s just taking a pause and a moment to say, “I need to ground myself,” and give voice to that.

Peter: Do you have a regular meditation practice?

Sheryl: I don’t myself, although I will breathe in at times, and I think what my meditation practice … Let me put it this way. Everyone has their own meditation practice. For me, it might be defined differently than what you’re traditionally saying is meditation, but to me, my meditation practice is, as soon as I go into my house with my family and I ground myself with being in them, that, to me, is my meditation, when I can be fully focused on what’s happening with them, it brings everything back to me as to what the most important priorities are in my life, and I bring that energy back into work.

It also, quite frankly, reminds me about love and being able to bring my love into my work, into my interactions with my people, is a part of my core philosophy as a leader. My connection with my family is what reminds me as to what’s important to me as a leader.

Peter: That seems like it’s very useful to have some kind of regular practice, and that practice might be being present with your family. That practice might be what you’re calling traditional meditation, which would be to sit on a cushion or chair and breathe, but something that gives us a practice in coming back to being present, so that in the heat of the moment, we actually have access to the internal tools that allow us to say, “Something’s not right. Let me take a moment and go inside and be present and figure out what’s going on.” If we don’t have some kind of a regular training in that in some ways, then it would be very hard to do in the heat of the moment, I imagine.

Sheryl: Yeah, and I think that it all boils down to, at the end of the day, what’s most important to us, as people and as leaders? To me, gosh, if those two things are totally separate, then there’s a core issue in terms of leadership, because you can never be bringing your authentic self. To me, my mantra is love. We talk about, in my work, being rebel-hearted, and to be able to keep grounding myself in what brings me that feeling of love and joy so I can make sure that I’m bringing it into my company every day is what is critical.

I think when you talk about grounding yourself in some ways, through meditation or whatever it is, it’s being able to dig deep inside as to who you are as a person, who you are as a leader, what’s most important, and what are the practices that allow you to keep bringing that back out, and making sure that that’s front and center for you as a leader.

Peter: Her book is, Killing It: An Entrepreneur’s Guide to Keeping your Head without Losing your Heart. Sheryl O’Loughlin, thank you so much for being on the Bregman Leadership Podcast.

Sheryl: Thank you so much, Peter, so, so much. I really appreciate the conversation.

Peter: If you enjoyed this episode of the Bregman Leadership Podcast, please subscribe and leave a review on iTunes. For more information about the Bregman Leadership Intensive, as well as access to my articles, videos and podcasts, visit peterbregman.com. Thank you to Clare Marshall for producing this episode, and to Brian Wood, who created our music. Thanks for listening, and stay tuned for the next great conversation.