Jessica Rolph on Managing 'Micro Failures' at Work

Two-time entrepreneur Jessica Rolph is embracing what she calls “micro failures” at work. You know, when you say the wrong thing to a team member, make a mistake on a project, or you don’t communicate about something. These moments can feel small, but they can take a big toll on us. But Jessica believes it doesn’t have to be that way. As the co-founder of baby food biz Happy Family, which sold to Danone in 2013, and as the current co-founder of the child development company Lovevery, Jessica’s learned to push through the shame and lean into those moments to become a better leader. 

In this episode, Jessica shares: 

• Why she scaled back on her friendships when she was working at Happy Family 

• How she thinks about “micro failures” 

• Why she was sad when they sold Happy Family 

• A moment where she felt lost at work

• When she decided to launch Lovevery

On Micro Failures

Jessica: One of the things I feel today is I kind of almost have these micro failures all the time,  like, "Oh, I wish I had said that differently to that team member or I wish I had done that differently." And I sort of think about it at night. I process it. I don't know if anybody else does, but I’ll go through my day … with this critical eye. And sometimes I'll even apologize to people or say, "I think that that came off wrong and let me reconnect with you on this."

…. Sometimes I think I try and just shove it away, but then if I can push through the shame of it and be like, it's okay, I can begin again. I am human. I will make mistakes. Is there anything I can do to make this better and be honest about this and vulnerable and share that I feel embarrassed or I didn't handle this well or whatever it is.

On Selling Her Company

Jessica: I was not an internal facing COO type. I really wanted to share ... the excitement and some of the glory, right? And so I think that for her [co-founder], she probably was looking for a more internally focused COO and co-founder. And for me, I was looking to have this like ride and this experience with a partner that I could share that with. And so that lack of alignment I think caused us some stress. And for me it was self-esteem…. And I think that on the day we sold, I remember feeling sad and it was weird, right? Cause we had like accomplished the impossible. We built a multimillion dollar company out of nothing together and we had a three year earn-out…. But I just felt sad and I felt bad about myself. Like I wish that I had not had such an ego response. And then also feeling like, wait a second, like I did this and I give credit and I want to receive some too.