How Motherhood and Career Coexist

—14 Personal Questions, Answered

I recently had the pleasure of connecting with Amanda Jane Jones and Jennifer Fernandez, authors of the new book, Mother / Founder, to chat about the intersection of entrepreneurship and motherhood. If you haven’t yet been introduced, Amanda is a brilliant graphic designer, illustrator, author, and co-creator of Kinfolk Magazine and Define Magazine. Jennifer is a talented writer and editor who has been on staff at Architectural Digest, Travel + Leisure, and Martha Stewart Weddings; her work has appeared in The Wall Street Journal, Elle Decor, House Beautiful, and more.

Mother / Founder profiles more than sixty empowering women who share their insights on raising children, running a business, and the complex ways these roles intertwine. To celebrate the book’s release, I’m answering Amanda and Jennifer’s questions on career and motherhood, from navigating mistakes to seeking balance to finding joy in the everyday.

You can find Mother / Founder wherever books are sold, including Amazon, Bookshop, Barnes & Noble, and your favorite local bookstore. I hope you enjoy our conversation!

Amanda and Jennifer: We’ve followed you for over a decade, from blog to Instagram to Substack. We’ve loved seeing your family grow, and your business evolve. Your style is iconic and always seems so ahead of your time. We’re excited to hear more about your entrepreneurship journey. Can you talk about your career arc and what initially drew you to entrepreneurship?

Kate: I grew up in a creative family. My mom stayed at home and spent evenings singing soprano in many choirs. There was always music on in the house and I played the flute and bassoon. My dad, a writer and poet, ran our family’s ad agency. There was always a lot of lively discussion around current events. I spent most of my time in childhood dedicated to my Irish dancing career, clocking twenty-one hours a week and competitions year-round. I think it all kind of primed me to move into a career where I’m firing on all cylinders. Creativity and purpose-driven action were just part of life.

Amanda and Jennifer: Did you have a lot of examples of female entrepreneurship in your life? If so, tell us about them.

Kate: I didn’t grow up with many, but there were women in my life I looked up to the same way I would a business owner. My grandmothers were forces. Active and engaged in different ways, through lifelong learning or travel, they were always busy and interested in what life had to offer. My high school boyfriend's mother was meticulously put together in every way, but it was the way she organized the house and schedule with the precision of a Fortune 500 company that had an impact on me. My dance teachers taught me a lot about turning seeds of passion into a full-fledged obsession with excellence.

My mom said something that took me years to not take personally. She told me to not be a mother. She didn’t mean it the way it sounded to me at eighteen. She meant don’t let motherhood be your identity. I think she had some complicated feelings about transitioning out of the motherhood years into her second act. That stuck with me.

Looking back on this, I never thought being a woman entrepreneur would be a disadvantage when I set out myself, which is part naivete (a trait that’s been a gift and curse for me) but also that I never really thought I could fail. I think I just stayed focused on the gifts I had and how I could use them.

My kids and me in the thick of it.

Amanda and Jennifer: We’d love to hear the best and worst parts of being self-employed. And are there things you’d change about the path you took? Would you ever go back to working in-house somewhere?

Kate: The best part is flexibility, freedom, and autonomy.

The worst part is flexibility, freedom, and autonomy.

When you have all the cards in your hand and all the responsibility for making the decisions, it can be a double-edged sword.

And yet, I can’t imagine myself going back in-house. I loved consulting roles that allowed me to be in-house for longer sprints. The longest position I took ended up being around two years. It was a joy. I’ve learned to never say never, so if the right opportunity comes at the right time, perhaps it could happen. I have tried to divorce the idea of willing the future to bend to my preferences.

Amanda and Jennifer: In American society, we're often toggling between this idea of hustle culture and self-care. How much of your free time do you sacrifice to your business (or your family) and how do you maintain your sense of self and sanity among the chaos?

Kate: I am at a phase where I can give myself time not to be locked into my computer. I don’t view it as not working, however. Life is a gorgeous buffet of inspiration. This is a regenerative mindset that only failure (aka life experience) can genuinely bestow. My kids are a massive source of inspiration now that they exercise more free will and personality. Yes, parenting is hard, but how they look at the world is infused into everything I make. Parenting has made me aware of what I lost when I started to play the “game” of “making it” or being successful. I rarely do my best work when measuring myself up to others' expectations. Kids are humbling in the best way.

Work always costs something. In addition to being privileged enough to have the space to entertain thoughts of purpose and fulfillment in my work, I am working part-time and setting my schedule, aiming for twenty hours a week, though I realized last week it has crept up to 30-35. My partner does drop-offs and pick-ups when I’m in the zone and cranking out writing or design work.

My days usually follow this pattern: I get deep-focus work done before the kids get up, the only time I feel is mine without guilt. Sadly, everyone has to be unconscious for me to feel like this, but a mother's brain is wired this way, I suppose. Later in the morning, I spend a chunk of time invested in physical movement or learning—tennis, yoga, Pilates, walks, cooking, reading, visiting art galleries, or catching up with a friend. I usually find something in that activity that sparks an idea or concept for writing or content. I return to work after lunch and am with the kids until bedtime. If I have energy, I log back on once they’re asleep.

Socializing has been a big part of keeping my life balanced; however, I’ve been called to a more introverted pace these days. I think when we’re going through significant shifts, there is always a need to go inward. I’m there right now.

Late nights working post-partum with my first child

Amanda and Jennifer: You recently downsized your business—letting go of your studio and, if we remember right, some employees for a better work/life balance, and you’ve seemed to thrive! Can you walk us through the journey you took to get here?

Kate: It took a long time to get to a place where I faced the fact I had to downsize. I knew it probably two years before I actually did it, but honestly, I just thought I could keep slogging away and ignore it. I knew this crisis was coming, and even with all the warning signs from my intuition and physical burnout, I didn’t feel like I could stop without it all falling apart.

The decision was partly financial, but really my heart hadn’t been in content creation at that scale for years. I wanted more autonomy and flexibility to take risks. I felt really guilty about all of it and spiraled afterward. The financial piece was what forced me to confront how I actually felt about trying to dig out of the hole I was in.

The irony is I had started to care for myself physically as all of this work stuff was imploding. I had gone off antidepressants and was tuning into my body through movement, and I felt like myself again.

But once I downsized, I felt this tsunami of failure and shame. It was crushing. I spiraled for a while and found myself in a career season where I questioned my entire identity and purpose.

It fell apart anyway, at least my inner world did. I needed rest and space. Then, I couldn’t figure out how to afford to do those things. The only regret I have is that I didn’t lean on the people who were there for me. If I’m being honest, I had no idea how even to start.

I think of my life as an entrepreneur differently now. I used to think of my job as driving a fast car from point A to B, efficiently and effectively, something I never did well but expected of myself. Now, I think of work as something I do, like dancing or running. Creating something tangible from my inner world is my job. I’ve connected making money with finding possibilities in ideas and things I want to make. I respect that process above all else and think sometimes it’s just my job to translate for wherever that impulse to make comes from.

Amanda and Jennifer: In addition to downsizing your business, this also coincided with a big move and a major renovation, for which we remember you received some pushback for your design choices. It’s been fun to be on the outside looking in and seeing all the style choices you made years ago begin to be mainstream now. We remember being impressed with your ability to ignore the negative voices and choose what brings you joy from your home. Teach us your ways!

Kate: I’ve always been sort of “in tune” with what’s coming next. It comes, I think, from being a visual listener. I sense a tone in the collective, see where people might be missing out on what they need, and then the visual pieces respond in kind. Significant shifts often stem from what we’re missing in our environments and relationships.

So, the negativity around my design decisions in my new home at the time, I giggle about it now. Seeing it all play out is fun, but I’ve already moved on to something that snagged my interest.

When I’m tinkering around with what I love or dealing with people triggered by something I’ve done or said or designed, I remember it’s not about people getting it; it’s about continuing to play and put things out there even if I’m not sure where they’re headed. It’s all play. And it’s not that serious.

Amanda and Jennifer: We know it’s a taboo subject, but we find money talk empowering. Many of the mothers in our book had to save up, work two jobs, or get business loans before starting their companies. Some had investors; some went on Shark Tank or did Kickstarter. What was your experience and what’s been the most helpful thing you learned as you became financially independent? Do you have any tips for being financially independent as a woman and mother?

Kate: I love talking about money. It’s been a shameful subject my entire life. I’ve associated it with greed, and my whole career has felt uncomfortable. Especially since so many people think influencers are rolling around on beds of money. Very, very few of them are.

I started Wit & Delight because I was so broke. I had maxed my only credit card and had no savings and no one to bail me out. I had to figure something out. I was a graphic designer and thought a blog would help with freelance clients. I coded everything myself and I was able to bring it to life pretty quickly. And then the rest snowballed. I don’t think I ever felt it was deserved, and as my team grew, I felt mounting pressure to make a system out of what felt like luck that could run out. So I hired out that role and learned a lot about asking for what you want. I still felt like an absolute fraud and eventually burnt out and you can read about what happened next above. Ha!

When you run a business and have lived most of your life without a safety net (or financial backing from family or investors), you come to rely on yourself to do what it takes. I’m learning that building in security and time for rest isn’t about being greedy. It’s about relationships, reciprocity, and community. I’m growing in this area.

I do now have something I didn’t when I started Wit & Delight, and that is the safety net of a partner. We couldn’t live the way we do without my partner's income, his significant parental support, or the health insurance his employment provides.

At a photoshoot with both kids in tow

Amanda and Jennifer: In Mother / Founder, we love stories about learning from our mistakes. Can you share a mistake you made and how you overcame it?

Kate: Where do I begin? This entire interview has a singular thread running through it and that is this:

Most mistakes are us getting in our way.

My biggest failure was not one massive flub but the cumulative effect of believing I was alone in my struggles.

Please do not confuse this with grandiosity or pride. It revealed a painful truth: I had no idea how to tell people what I needed. I didn’t even know what it was I needed.

Unfortunately, this isn’t something you can just go out and find by taking an online course. It comes with putting yourself out there again, and this time, accepting not only help but the kindness and support of others. We have to believe we’re worth it.

I think it’s why doing something super hard, like starting a business, is so life-giving. The process shows us what we’re made of and where we’re vulnerable. If we’re lucky, we’ll fail a lot, and those failures will result in the kind of growth that benefits us far beyond any business metric we could measure.

Amanda and Jennifer: We think one of the biggest themes of Mother / Founder is that we can’t do it all. What tasks do you prefer to delegate and which ones do you like to keep in your queue?

Kate: Well, that was a nice lead-in!

I like to ask myself what I dread having to do. I hand over a lot of the tasks that overwhelm me to my husband with total autonomy. On something like the cake for my daughter’s birthday, he’s excited to step up. Often I’m called back in to give advice or pinch-hit, but because it’s totally off my radar, I’m not so ragey about it. I think the key is that it’s not sitting in my brain as a piece of unfinished business. I just have to let go of the outcome being exactly what I’d do.

For work, I have learned to do the things that I love to do as well. I’m not great with details and closing loops, so I have two people on a very part-time basis to help with editing and business deals. The editor helps me craft outlines and rough drafts for upcoming pieces and then edits them once I’ve written and revised them a few times. I also have someone who helps me with clients I decide to take on and project manages products I’m working on. She handles the contracts and billing and little issues that arise with revisions. Other than that, it’s all me, baby. And right now, this help is allowing me to return to my intuitive, creative process. I like sharing things off the cuff. I like being more in real-time. I like having my finger on the pulse of things.

I think it’s OK to hold on to a role that is life-giving for you. Just make sure it’s not from a place of control.

Bennett home sick during a Maria Stanely shoot

Amanda and Jennifer: Do your children appreciate what you do? Has self-employment been an empowering experience for your family?

Kate: I only recently introduced my work and brand to my kids. They think it’s cool that I am my own boss and they think my social media videos are a little silly. They make fun of my “work voice”. But my daughter has been talking a lot about her own business ideas. She’s full of them, and naturally comfortable expressing the value of her ideas. She’ll ask for money for her little creations she makes out of trash, connecting them with a need she picked up while observing the family dynamics. I love nurturing this spirit in her.

The picture.

Last week she drew this picture of me asking a man for money. My face looks devious, and the man looks withdrawn and sad. She drew herself behind me, cheering me on (see the bicep!), and her brother expressing confusion. It's clear she has ideas around what it means for women to be “in business” and thoughts on how gender plays out here, too. I didn’t share much of a reaction when she presented it, instead bringing the picture to therapy the following week.

A year ago, this picture would have gutted me. Now, I see that I am example of how female entrepreneurs build value—money is just one way to measure it.

Amanda and Jennifer: How did you navigate maternity leave?

Kate: I went right back to work. It’s hard to reflect on this. I don’t have many memories. My health suffered, long past postpartum. I was just surviving.

Amanda and Jennifer: One thing we love about Mother / Founder is we really debunk the myth of women needing to act like traditional businessmen to be successful. And we’re also redefining what success outside of monetary terms might look like for people. Would you agree with that? And if so, in what way?

Kate: I wholeheartedly believe this. I just started reading The Serviceberry by Robin Wall Kimmerer and my mind is reeling with all the ways reciprocity and abundance show up in our natural world. I think women are really powerful when tapping into their most intuitive and natural energies. I give myself permission all the time to structure my day to include more play and a little chaos for this reason. I work better when it’s less linear.

I dream of an alternative reality where the laws of nature are baked into how we look at creating and giving value. Sigh.

Amanda and Jennifer: Are there any books you recommend to read for someone starting out? (Aside from Mother / Founder, of course!)

Kate: I would recommend:

• Daring Greatly by Brené Brown

• The Perfectionist’s Guide to Losing Control by Katherine Morgan Schafler

• You Learn by Living by Eleanor Roosevelt

• Nonviolent Communication by Marshall B. Rosenberg

• The Obstacle Is The Way by Ryan Holiday
  

Amanda and Jennifer: If you could go back and tell yourself one thing before starting your business, what would it be?

Kate: Ask for what you want. If people are interested in what you’re doing or saying, believe them.