Inner Voice & Trust with Jenna Bott


Today’s bonus episode features Jenna Bott, Art Director for the Sheryl Sandberg & Dave Goldberg Family Foundation, who worked on the visual identity for Sheryl Sandberg’s new book Option B.

Amidst holding down full-time jobs and having three children, Jenna shares how she came to call herself a designer over a decade of freelance projects, working at a small agency, and landing clients like Lean In. She also talks about dealing with rejection and imposter syndrome, and what it means to be “paid to learn.” For anyone looking to bridge into what they really want to do, Jenna has fantastic insights and advice to offer.

Subscribe and listen to the full episode here (you must subscribe to receive latest episode).

Highlighted Excerpt

Majo: Let’s talk about this challenge of you being self-taught, of not taking the traditional route so to speak… working the side hustle, going through ups and downs, but then getting a big client like Lean In. And then getting a job offer from them! Are you feeling any, like… Who me?!

What are you feeling?

Jenna: Yes. There was that. However, from the moment I stepped through the door at Lean In and started there full-time, they have relied on me. I worked closely with Sheryl on the book cover and on the identity of Option B... It’s almost like I didn’t have time to think about my self doubt – I just had to do it.

And I had to embrace my voice and what I thought. Embrace that girl way back when who was particular visually and had a taste, the girl who grew up and then hacked away at it – I needed to trust that voice, to lean into it, if you will.

Majo: Yeah. Trust the voice that knew how to do it, that could execute…

Jenna: Yes. But I’d be lying if I said I don’t struggle with imposter syndrome or thoughts of, Is this really still who I am? Am I still good at this? There are so many kickass designers everywhere! So why me… Right?

Majo: Comparison is the big imposter syndrome trigger.

Jenna: Mmm hmm.

Majo: So what’s helped you? What has supported you in processing that?

Jenna: I have a mentor I was talking to a while ago, and she brought up a really good point when I was in a period of Who am I?and Man, I have such a crush on that kind of work… or the thought of working for an organization like that… but that could never be me… (this was before Lean In).

And she told me, “You know Jenna, maybe the fact that you’re attracted to people doing these things or to these kinds of roles is more a clue about who you are than of what you’re not. And with that idea came this passion... this feeling that the gift is there, so how do I feed it? How do I let it blossom and not hide or question it? 

For me, especially with this job at Lean In and Option B, I’ve really had to embrace my voice and be okay with bringing my full self to the table. Whether or not that voice gets critiqued or people disagree – the only way I am personally going to grow at this stage is if I let that person show up.

Show Notes:

  • Jenna growing up: A “visually particular” tomboy who didn’t identify as an artist. [2:32]
  • How she felt a strong pull to the arts in college, but went in a completely different direction, plus her one creative outlet and the job that sparked her love for design. [6:55]
  • Jenna shares the pivotal motivation and insights that came after a crushing rejection. [10:28]
  • On her decision to switch things up after becoming pregnant, and the internal challenges around embracing herself as a designer that she had to get over. [14:08]
  • Growing her freelance business while working full-time with three kids... how this hustle phase paid off when Jenna landed Lean In as a client. [19:59]
  • Persevering through self-doubt by trusting her inner voice, plus great advice from one of Jenna’s mentors. [23:18]
  • On being in process and still figuring things out, and how she approached her work on Option B. [27:57]
  • Majo and Jenna discuss Sheryl and her new book: Her goal to normalize the conversation around grief, making it okay to talk about, and the importance of knowing how to comfort others. [31:51]
  • What Jenna has learned from her work on Option B, and her final words of wisdom. [34:40]

Subscribe and listen to the full episode here (you must subscribe to receive latest episode).


Option B – Get the book

The Sheryl Sandberg & Dave Goldberg Family Foundation


by Lucia Lilikoi

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