LISA CHOW: From Gimlet Media, I’m Lisa Chow. This is Startup, the show about what it’s really like to start a business. On this episode, we’re going to hear a conversation between a founder and an executive coach.

JERRY COLONNA: What what would feel comfortable talking about and useful.

DIANA LOVETT :Yeah.

JERRY: Because that's the key.

DIANA: I mean, I think the biggest thing is for me personally, um you know— I'm like getting teary even talking about it. I find it very challenging to navigate being a mom and being an entrepreneur and you know really feeling so um... really guilty about,missing out on so much stuff at home. And then when I do you know leave work, about all the things I've left undone. So that although it's very personal and very vulnerable, you know, feels like something it would be super helpful to address.

LISA: This is DIANA Lovett. She started a company called Cisse Cocoa, which makes baking mixes, hot chocolate, and other cocoa products. She’s talking to JERRY Colonna, who will be familiar to longtime listeners. He was the CEO whisperer from Season 2. He’s also the executive coach to Gimlet’s founders, Alex and Matt. He used to be a venture capitalist and has a lot of experience working with entrepreneurs. A few weeks ago, we did a call-out to our listeners. We were looking for entrepreneurs facing some kind of problem connected to their business … and that’s how we met DIANA. She started her career working for international NGOs -- but she got disillusioned after seeing donors’ priorities shift. So she began thinking about other ways to have a positive impact. She wondered: what if I took this thing that I love, chocolate, and built a business on it that supports small growers around the world.

DIANA: Our cocoa is grown in the Dominican Republic. It's grown by a cooperative called Fundopo and // they've put in some clean drinking water wells. They've renovated schools they've built a community center. And that model really appealed to me, it was locally needs driven.

LISA: Cisse Cocoa is growing. DIANA’s products are on shelves in more than 4,000 stores, including at Whole Foods, Target, and Stop & Shop. She has visions of building out a brand as recognizable as Annie’s Organic. But the thing that she struggles with most, day to day, is balancing being a CEO and being a parent to two young kids. And so when DIANA sat down with JERRY, the executive coach, that’s what they talked about. It’s a conversation that a lot of working parents will probably relate to. I know I did. DIANA’s session with JERRY lasted an hour and a half. We’re going to play you a shortened version of their conversation.

DIANA: I mean it feels kind of relentless, you know what I mean, like from the minute I wake up in the morning I'm baking brownies for a meeting, trying to have a little bit of time to connect with my kids, running off to work -- you know like, I get home we make dinner. It's... there's... I don't have a place to be calm and present until like 9:30 p.m. and then I'm exhausted.

DIANA: I feel like I can get hacks from other people I can get like advice but the like, how I face this as a person is so hard.
JERRY: Yeah.

JERRY: We're going to be calm and present.

DIANA: Ok.
JERRY: So that your brain and your body can experience some of that and we’re going to talk about the challenges associated with that.

DIANA: OK.

JERRY: And we may or may not end up with a life hack or two.

DIANA: Ok.

JERRY: But life hacking doesn't really get us the answers.

DIANA: Yeah. No I think it's like emotion hacking or something so that you're.

JERRY: It's hacking being human.

DIANA: Yeah.

JERRY: So I have a couple of questions just to help give some context to this.

DIANA: Yeah.

JERRY: How old is the company.

DIANA: It's five and a half years old.

JERRY: And tell me you're married.

DIANA: Yeah. I have a husband.

JERRY: And what's his first name.

DIANA: Matt.

JERRY: Matt. And how long have you been together.

DIANA: We've been married for seven years.

JERRY: And how old are your children.

DIANA: Basically five and two. Like they're about to have birthdays.

JERRY: Gotcha. And what are their names.

DIANA: Noam and Tali. A boy and a girl.

JERRY: And Noam is the older.

DIANA: Yup.

JERRY: So both of them have only known mom as an entrepreneur.

DIANA: Um hm, yeah.

JERRY: And that landed for you just now.

DIANA: Yeah.

JERRY: What's up?

DIANA: I mean it's a lot of guilt. You know I didn't take a maternity leave with either of my kids. And I feel like that sort of I don't know paradigm or example of like I feel like I've prioritized work over my kids. And they never—

JERRY: Slow down. When I tell you to do that it's not that you've done something wrong.

JERRY: It's because our impulse when we touch really painful stuff is to speed through it but it's like hitting a speed bump and speeding up and all that's going to happen is we're going to wreck the undercarriage of the car. So we actually want to go slow over those tough spots. You feel like you prioritized work over your children.

DIANA: Yeah.

JERRY: That's a big statement.

DIANA: Yeah.

JERRY: And I'm staring into your eyes and I'm seeing someone who can't believe she just said that.

DIANA: Umhm.

JERRY: Yeah, yeah.

DIANA: Cognitively I know that they are deriving benefit from seeing me you know chase my dreams and...

JERRY: Bla bla bla.

DIANA: Exactly. Exactly. Exactly. Yeah. So.

JERRY: But emotionally.
DIANA: Yeah.

JERRY: --it feels like crap.

DIANA: Yeah. No I feel t-- I mean you know my son... Noam asked me this morning, "Mama can you take me the aquarium today?" And I was like, well that's a good question. You know I said well I can take you over the weekend. And he was like well... I want to go with you today.

JERRY: Right.

DIANA: So you know it was 7:15 this morning. And you know like he's really happy he's well adjusted you know he's great. So I don't think he's living in a world of deprivation. But I am missing that. And I think it elevates my stress level at work because I try and be home for family dinner so I have that internal cut-off like have to be there at 7. So I feel like it's like sort of negative at home because I'm not there enough.

JERRY: And negative at work--

DIANA: And negative at work because I'm so aggressive on like —no I can't take that on too, you know I mean like... I feel like it's putting all sorts of boxes around it that's making it harder everywhere.

JERRY: Yeah.

DIANA: So that's what--

JERRY: So you feel like you're failing on both ends.

DIANA: Yeah I don't think it-- I don't think it's helpful. Yeah.

JERRY: Boy howdy you've got a lot of guilt. You feel guilty because you're not a good enough leader.

DIANA: Yeah.

JERRY: And you feel guilty because you're not a good enough mother.

DIANA: Yeah. You know for me it's the, it's the time I just I don't know how you're supposed to you know spend every minute with your kids and spend every minute at work.

JERRY: Where did you get the impression that you're supposed to spend every minute with the kids at work.

DIANA: Yeah. That's a good question. I'm not... I don't want to have... you know I wouldn't want to have no profession. But I think the you know the challenge for me is just you know making more time.

JERRY: Making more time.

DIANA: Or making better--I don't know. You know I don't know what the answer is. You know making better time. You know just like getting into that mental space where I feel happy and present at home and I feel happy and present at work. And I'm not.
JERRY: Sorry. Yeah.

DIANA: You know feeling tethered or guilty about the other one when I'm you know what I mean.

JERRY: Yes.

DIANA: Like, I do this when I get home from work. I zip my phone into my backpack and I hang it in our mudroom so.

JERRY: Nicely done.

DIANA: It's like not present. You know, so that this family dinner and putting the kids to bed is separate from that.

JERRY: Yes.

DIANA: But even during that time, you know if you have a bad day. It's sort of like dour cloud. You know it affects you. I can't I can't zip the way I feel about work into my bag. It’s -- I may not be checking my email or you know transacting business at the dinner table but sometimes it's occupying my attention even when I'm sitting with my family.

JERRY: OK. So let's stay with this so. I love your I'm going to zip my phone in my bag. But that's a hack.

DIANA: Right.

JERRY: And what you notice is it actually doesn't alleviate the anxiety that you're carrying from work and so then you're fee-- And this is what you're doing. You're feeling guilty because you're feeling anxious and then you're feeling anxious because you're feeling guilty. And the only question, the only choices that you seem to be holding onto is make more time or make better use of the time that I have.

DIANA: Yeah.

JERRY: How about not feeling guilty.

DIANA: I know! How?

JERRY: OK. I want to read you something. And um...one of my teachers is a Buddhist teacher named Sharon Salzberg. And this is from a book she's written called loving kindness

JERRY: "Buddhist psychology makes an interesting distinction between guilt and remorse. The feeling of guilt, or hatred directed towards one's self, lacerates. When we experience a strong feeling of guilt in the mind, we have little or no energy available for transformation or transcendence. We are defeated by the guilt itself because it depletes us. We also feel very alone. Our thoughts focus on our worthlessness. I'm the worst person in the world. Only I do terrible things. However, such an attitude is actually very quote self promoting. We become obsessed with self in the egotistical sense. Remorse by contrast is a state of recognition. We realize that we have at some point done something or said something unskillful that caused pain and we feel the pain of recognition. But crucially remorse frees us to let go of the past. It leaves us with some energy to move on. Now it's a long quote but it's an important quote I think for you to work with because, I get moving back and forth between feeling like I'm doing a crappy job at the office and a crappy job at home. And you're too sophisticated to fall into the trap of thinking you're supposed to have it perfectly figured out aren't you?

DIANA: Right.

JERRY: Thinking about your children for a moment-- what what do you believe about the world that you would like them to know. What is value would you like to have?

DIANA: Yeah I mean I think I I want them to be conscious. I.

JERRY: Empathetic perhaps?

DIANA: I want them to be empathetic. I want them to have a sense of empowerment that when
they see an injustice that they're empowered to be change makers.

JERRY: What if they fail.

DIANA: I would be proud of them for trying.

JERRY: Yeah. What creates the pride in trying even if you fail.

DIANA: I mean it's better than doing nothing you know or... so I did this you human rights fellowship after I graduated from college. And we used the Holocaust as a framework for understanding contemporary issues of human rights. And in that framework. There was people who were bystanders. There was people who are collaborators. And then there were people who were part of the resistance. And you know, I want them to be part of the resistance.

JERRY: Oh yeah, yeah. So is it possible that if they hold the understanding that mom was part of the resistance--yeah. And that sometimes we couldn't go to the aquarium. But she loved us nonetheless.

DIANA: I think so, but I don't know so. You know and... and I think even well-intentioned parents can do things that you know affect children later in life in different ways. And maybe I inspired them to be part of the resistance but all they wanted was for me to be at the lacrosse game, you know. And that's like that's my little agenda. That may not have been their little agenda.

JERRY: Well that's the self-laceration.

DIANA: Yeah.

LISA: Coming up: How do you stop self-laceration and express remorse to a five-year-old … and what exactly does it mean to be a good parent. That’s after the break.
AD BREAK

Welcome back to Startup. When we left off, Diana was talking to Jerry about the conflict she feels … wanting to do the work that she’s passionate about … but also wanting to be there for her kids. Jerry continued the session by asking her about her expectations for herself.

JERRY: Can you forgive yourself for leaving home in the morning.

DIANA: Yes.

JERRY: Can you forgive yourself for leaving work.

DIANA: Yes.

JERRY: Can you forgive yourself for not taking your son to the aquarium today.

DIANA: No.

JERRY: If the shoe were on the other foot could you forgive. Noam for disappointing you.

DIANA: Yes.

JERRY: So you're holding yourself to a standard that you don't hold anybody else that you love to.

DIANA: Yeah but I think it's different for parents.

JERRY: What are parents supposed to do.

DIANA: I mean, they're supposed to be the people that are you know unconditional love, they're supposed to nurture and support you. They're supposed to, you know, that's my framework right. Like you're supposed to bring your own values and share those with your children. But then you're also supposed to be like “but who are these tiny creatures and how do they express--” you know and then be supportive of that. OK. We know we took them to skating, they hated that let's do painting, you know mean like, to constantly be taking the feedback of who they are, and incorporating that into how you raise them and constantly kind of reading the tea leaves of their faces. I think they just need a hug right now, you know what I mean, like to intuit their needs on all levels. And I think.

JERRY: What are the... what are the... what is the skill set or the way of being that's most in service to them. There you are reading the tea leaves of their eyes, trying to gauge do they need a hug? Do they need a trip to the aquarium? Do they need a mom that they can believe in as a leader of the resistance? What do they need?

DIANA: Unconditional love.

JERRY: What would unconditional love give them about themselves.

DIANA: Self-empowerment.

JERRY: Yeah. So when you spend all this energy trying to anticipate and meet their needs, how does that help their self-empowerment? Look I'm going to respond to you, not even as
a coach but as a fellow parent. Only my children are adults now. I lacerated myself in the same ways.

DIANA: Yeah.

JERRY: So I really relate to where you're coming from and the one salvation for me was the realization that, stumbling our way through, we gave our children the ability to speak to say this is what I need from you. Sometimes modeling for them what it means to be a participant in a larger more conscious world. My therapist once gave me a really powerful piece of parenting advice. You are going to screw it up. Get used to that. The issue is not how do I prevent that but how do I instill in my children the resiliency so that they can grow into their own adulthood.
DIANA: But why? Why do we have to accept that we're going to screw it up?

JERRY: Because we are imperfect beings. And because learning to actually be with our imperfections as parents perhaps is their most important lesson. Do they love you regardless of your imperfections.

DIANA: Yes.

JERRY: That's a powerful powerful lesson. Can they be loved despite their imperfections.

DIANA: Yes.

JERRY: Would you love them nonetheless. No matter what.

DIANA: Yes.

JERRY: That's the lesson.

DIANA: Yeah.

JERRY: Teach them how to speak that they felt disappointed. Teach them how to think about responding to somebody knowing that unconditionally no matter what they say they will be met with love. And to say, mom, I was mad that you didn't come to the game.

DIANA: Yeah.

JERRY: That hurts. But it's a powerful lesson.

DIANA: Yeah.

JERRY: From where I sit, I think that's as important if not more important than actually you being at the game. Learning at an early age, I am OK whether or not mom's at the game. Sure, I want mom at the game.

DIANA: Yeah.

JERRY: But I am not annihilated and devastated because moms not at the game because I know mom loves me. And when I tell her that I'm mad she's still going to love me.

DIANA: Yeah. Yeah.

JERRY: That's a pretty powerful gift.

DIANA: Yeah. I mean maybe it's hard because they can't articulate that right now. You know what I mean.

JERRY: That's right.

DIANA: They're so little that they're not really that's why I was saying it's like reading the tea leaves. You know your kids are older so and they can tell you they're upset about it. And like I think my 5 year old kind of can because he's like I want you to come to the aquarium and that I'm like I can't because I have to work, but then if I tried to say you know and how does that make you feel, he's be like, OK.

JERRY: No, but might say you might model.

DIANA: Yeah.

JERRY: And that makes me feel sad Noam. And so I want to spend time with you. And sometimes I can and sometimes I can't and that makes me feel sad. That makes me feel sad too, Mommy. You see what I'm saying. What you're reaching for is presence where I think, if I may, where I think you’re still getting tripped up is a kind of hacking that the only way to meet Noam's need in that moment was actually go to the aquarium.

DIANA: Yeah. Yeah.

JERRY: That's an impossibility.

DIANA: Right. Right.

JERRY: So here's the kind of leadership assignment slash growth assignment.

DIANA: Yeah.

JERRY: You made the connection before to your own company.

DIANA: Yeah.

JERRY: Leaning into these spots, learning how to be with these conflictual feelings is really important for the company. It's really important for your own resiliency. And it's really important lesson to model for
those kids.

DIANA: Yeah.

JERRY: Because they're going to face the same kind of conflicts in life.

DIANA: Yeah.

JERRY: They're going to be torn.

DIANA: Yeah.

JERRY: They're going to want to be in one place and the other. What you can give them, which very few other people in their world will be able to give them, is modeling a way to be with those conflicts. Not with guilt that lacerates. But, yeah I'm sorry I missed that. And I'm going to let it go. And I'm going to look forward to the thing that we are doing together.

DIANA: That would be amazing to give them.

JERRY: Imagine they enter their 30s and 40s with that kind of a perspective. They enter their parenting with that kind of perspective.

DIANA: That makes a lot of sense. I mean to give them that I think especially my daughter, because I do think it's more powerful for women but.

JERRY: I think it is intensely powerful. It is a torture for women.

DIANA: Yeah. That concept of you know of no guilt or whatever else. I do think that that's a pretty powerful thing for myself, for them, and probably for my other colleagues who are parents you know.

JERRY: Tell me how are you feeling.

DIANA: Yeah I mean, I think the part that's really like connecting for me is you know saying it. So instead of just be like oh I wasn't here, I didn't make it to the aquarium, is being able to say, you know I'm sad we didn't get to go together, we could go together on the weekend, or you know whatever else. I think the the point that I'm... I think is going to be harder for me is to, as you said you know guilt is very lacerating, is actually you know I can verbalize the remorse you know but actually just shutting down that you know stopping that and redirecting it that feels harder.

JERRY: So a word about that.

JERRY: Learn some slow time. As you're putting the kids to bed tonight, look into their eyes. Don't just put the phone in the bag. Look into their eyes. Here's a memory. You know what they smell like after they've taken a bath.

DIANA: So good.

JERRY: So good. You know what they feel like when they snuggle you and they have their pajamas on and they're getting ready for bed and mommy will you read a book to me.

DIANA: Yeah.

JERRY: Those are the precious slow times. Those are the times. Watch the laceration it just came back in.
DIANA: I know I feel like I've been rushing through it you know I'm like oh let's get the kids to bed so we can clean up. So like... because it's so compressed, you know.

JERRY: Yeah.

DIANA: But I'm with you, I mean that is the good... you know. That's not one more thing. That is the thing.

JERRY: Yes.

LISA: When the session between Diana and Jerry ended, Diana took the train back home to where she lives, outside of New York City. I caught up with her a couple of weeks later.

DIANA: This is Diana

LISA: Hi Diana; it’s Lisa

DIANA: Hi Lisa, how are you?

LISA: Good, how are you?

DIANA: I’m good

LISA: Talking to Diana, I wanted to know how things had been since her meeting with Jerry. My kids are about the same age as Diana’s, and when she talked about her guilt, I understood where she was coming from.

LISA: You know hearing your conversation you know it was very... I was actually living vicariously through you. But it was very helpful.

DIANA: Yeah.

LISA: Because I mean just hearing your guilt I think a lot of moms experience that level of guilt.

DIANA: Totally

LISA: I certainly do and hearing Jerry talk to you about that guilt was interesting to kind of hear him challenge you a little bit on it.

DIANA: Yeah.

LISA: So I'm curious like... in the last couple of weeks has there been an instance where you caught yourself feeling guilt again.

DIANA: Of course. I mean it's impossible to you know flick that on and off so, absolutely. You know my son was like Mama I don't want you to go to work today.

LISA: In that moment … Diana borrowed some of Jerry’s language from the session.

LISA: And what did you -- how did you respond to Noam when he asked you that.

DIANA: I would say I want to stay home with you too. I'm so sad I'm going to miss spending all day with you. I'm going to go to work and I'm working on building something that’s about you know doing good and helping other people. And I'm really passionate about it. And say you know what I'm sad I'm not going to be here with you.

LISA: Right right…

LISA: Before how would you talk to Noam about, about leaving.

DIANA: I guess I would say you know oh don't worry you know I'll be home for dinner and you know we'll be together on the weekend or you know kind of maybe more dismissive or distraction

LISA: Right.

DIANA: Than acknowledgement.

LISA: And how did Noam respond.

DIANA: I mean you know he was like OK. He's five so he was like oh is that a bouncy ball. It was not like a big profound moment.

DIANA says she’s leaning on Jerry’s advice in other ways, too… being gentler on herself … and experiencing the “slow times”...

DIANA: I was like you know what I’m gonna sit at the table// with my coffee you know they're eating breakfast // you know when you really lock eyes with your little ones and you're connecting you're making them laugh or whatever else it's like what are you rushing through. You know whatever time you are spending with them like there's nothing that you know like what are you going to put them down here in like clean the dishes and do more work like that kind of stinks. So Why not really enjoy it.

LISA: Right. Right. It didn't cause any anxiety about not getting those things done on your to-do list.

DIANA: I mean now that you're mentioning it yeah but at the time no! thanks a lot Lisa!

LISA: Sorry!

LISA: Diana’s still looking for new hacks, like trying to include her kids when there’s downtime at work. A few weeks back, her company got a delivery in, and she invited Noam and Tali to the office to hang out while she unloaded pallets. She’s also planning to take Noam along the next time she demos her company’s products. But learning how to go easy on herself … that’s going to take time.

DIANA: It's probably like a 16 point turn and not a u-turn. //

Lisa: Right right.

DIANA: It's hard not to feel guilty about missing out on time with your kids. You know I'll -- What did you do today. Oh I went to swimming and you know I got a badge and I'm a slime eel now and you know you're just like I want to be there, I wanna see you get your little badge and so you know just that's always the challenge right.

LISA: Diana Lovett is the founder of Cisse Cocoa, a company that makes chocolate products.
The executive coach she talked to, Jerry Colonna, has his own podcast called "Reboot." If you’re an entrepreneur who’s facing a challenge in your company, and would like to talk about it on Startup with a coach, email us at startup@gimletmedia.com with the subject line “Coaching”. Tell us about the problem you’re struggling with, and how best to reach you. Next time on StartUp, a founder who’s trying to revolutionize medicine gets some unexpected lessons.

JAKE: I had to like learn a bunch of stuff about pigs because I knew nothing about pigs. So I was looking at like people who have pigs as pets. They have these lists of things to do with the pigs that they're real smart and they'll get bored if you don't give them toys. They get sunburned easily. Things like that.

LISA: The lengths you’ll go to, to follow a dream. That’s next week on Startup.

StartUp is hosted by me, Lisa Chow. Our show is produced by Bruce Wallace, Luke Malone, Simone Polanen and Emanuele Berry. Our senior producer is Molly Messick. We are edited by Caitlin Kenney and Pat Walters. Production assistance and fact checking by Alvin Melathe.

Mark Phillips wrote and performed our theme song. Build Buildings wrote and performed our special ad music.

Additional music by Bobby Lord.

David Herman mixed the episode.

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