Mom Guilt, the Village & Why Women Wait to Be Ready (When Men Just Do It)

Small Fish, Big Pond: A Fine Jeweler, Lawyer & Mom of 2 on Imposter Syndrome, Legacy Building & Showing Up Anyway

Pamela Adewoyin James was answering business emails from her hospital bed after giving birth. Her warehouse had just been set on fire during the riots. Forty thousand people had hit her website in under 24 hours after a Cosmo feature she wasn't prepared for. She had a full-time job as a lawyer. And a newborn. She kept going anyway. Today Pamela is the founder of Lola Day, a fine jewelry brand with a mission that goes beyond the product. She just completed a water tower in Niger providing clean water to up to 20,000 residents. She's building custom pieces with responsibly sourced materials. And she's on a mission to become the nation's fastest growing African owned fine jewelry business — because she couldn't name five African fine jewelers herself, and she refused to let that stay true. In this conversation with hosts Malliha and Corinna, Pamela gets real about what it actually feels like to be a small operation when big opportunities come knocking. The retailer who wanted 30,000 units by Friday. The payment that couldn't be released because her CFO and CEO were the same person — her. The opportunities she had prayed for that she had to say no to because she simply couldn't handle them yet. And underneath all of it, two kids who can't say it yet but are counting on her. And a woman learning to give herself grace while building something bigger than herself. Topics covered: * Going from hobby to Cosmo feature overnight — and the chaos that followed * Why she made the leap from fashion jewelry to fine jewelry * What the legal definition of conflict-free actually means — and why it bothered her as a lawyer * Building a water tower in Niger and what social impact really looks like * The big retailer experience that made her feel like a small fish in a very big pond * Saying no to opportunities she had prayed for * What she needs more of: grace, sleep, and less worrying * The sewing machine still in the box — and what it says about mompreneur burnout * Delegation as a survival strategy — not a luxury * Building systems before life forces you to About Pamela: @pamazonwarrior | @shoplolaade — lawyer, fine jeweler, founder of Lola Day, mom of two, and someone building a legacy one custom piece at a time.

Letting Go Is the Whole Job: A Mompreneur & Producer on Grief, Presence & Why Joy Is a Radical Act

In this conversation, Cat and Malliha get into the territory most mom content won't touch. The grief that comes with every developmental stage your child moves through. The way presence feels almost impossible in a world that is, as Cat puts it, designed for dysregulation. The difference between saying no from fear and saying no from power. And what happened the day her nine-year-old brought her a glass of water and said "Mom, you need something" a small moment that revealed something enormous about the home they'd built together. Cat also talks about joy not as a reward you earn after everything else is handled, but as a radical, necessary, non-negotiable act. And why she's centering it for herself so her daughter learns to center it too. This one is for the mom who is always on, always producing, always giving and is starting to wonder what it might feel like to just stop. Topics covered: * Letting go as the central practice of motherhood * Grieving every developmental stage and why we don't talk about it * Presence as a practice in a world built to pull you out of the moment * Why Cat thinks her career choice is connected to her anxiety * Saying no from fear vs saying no from power * Partnering with your child instead of leading them * Joy as a radical act and why it belongs at the center of your life * Raising a digitally native kid and the social media question she's not rushing to answer * What rest actually looks like for someone who is always producing * Becoming a lifelong student as the only real parenting strategy About Cat: @catjimenez — entrepreneur, producer, creative, single mom, Radical Monarchs troop mom, WNBA Valkyries fan, and someone learning to make space for the questions she doesn't have answers to yet.

The Balance Myth: A Video Editing Mompreneur on Why You'll Never 'Have It Together' — And Why That's Actually Okay

Kalee Isbell started her video editing company in 2019 with no business plan, two kids under two, and a single Instagram DM she almost didn't send. Seven years later she runs a team of nine editors all moms and has built a business around one simple idea: the videos sitting on your phone deserve to actually be watched. But this conversation goes way deeper than the business origin story. Kalee gets honest about what it actually looked like to build something in the margins of motherhood editing videos from the hallway while her kids took a bath, trying to work through COVID with zero childcare, and the year her revenue dipped and she told her husband it was all over. She talks about the moment she stopped measuring success by growth and started measuring it by whether she still enjoyed what she was doing. And she talks about surrender not as giving up, but as the quiet practice that made her a better mom and a steadier business owner. She also gets into something that doesn't come up enough: the question of whether we're over-documenting childhood, who gets to decide, and why asking your kids for permission before you press record matters more than you think. This one is for every mom who's tired of chasing balance and just needs someone to tell her that building something messy and imperfect is still building something. Topics covered: * Starting a business from a DM with no plan — and what year 7 actually looks like * Why every editor on her team is a mom and why it makes all the difference * The balance myth and why chasing it is making us feel worse * Working through COVID with two kids and no childcare * Surrender as practice and what those hard moments are building in you * What kids teach us about forgiveness and starting over * Over-documenting vs under-documenting childhood — where's the line? * The mom she thought she'd be vs who she actually became * How to start when your creative idea scares you About Kalee: @kaleeisbell | @isbellfamilyfilms — video editing entrepreneur, former teacher, mom of 2 (soon 3), and founder of a company built entirely in the in-between moments of motherhood.

Mom Guilt, the Village & Why Women Wait to Be Ready (When Men Just Do It)

Pumping in a Courthouse Bathroom: A Lawyer, Mom of 2 & Firm Owner Gets Real About Ambition, Mom Guilt & Refusing to Choose Mona Tash is an employment lawyer, co-founder of her own firm, and mom of two boys under seven. Four months after having her first son, she had a trial. She pumped in the bathroom between sessions. She brought him to an arbitration in Palm Springs when she had no other option. She didn't get maternity leave — because there was no one to pass her cases to. And she kept going. In this episode, Corinna, Malliha, and Mona get into the conversations most working moms are having in their heads but rarely say out loud — the guilt that shows up even when you know you're doing the right thing, the mental load that follows you on vacation, and the moment Mona's six-year-old told her she needed a break and she realized he actually gets it. They also talk about what it looks like to hold onto yourself through motherhood — the board seat Mona has kept for nine years, the 8am Saturday workout class she doesn't apologize for, and why she's actively trying to let her kids fail a little more so they can actually grow. And for any mom sitting on a dream right now? Mona's closing advice is the push you didn't know you needed. Topics covered: * The real cost of having no maternity leave when you own your firm * Mom guilt — where it actually comes from and what to do with it * Building your village and why the support system isn't optional * Letting kids fail as an act of love * Self-care that goes deeper than a spa day * Holding onto your pre-mom identity on purpose * Why women wait to be ready — and men just start * Taking the first step even when you don't have all the answers About Mona: @monatash — lawyer, firm co-founder, mom of two, and someone who has built her life around helping others fight for what they deserve.

Dr. Lisa vs. Lisa: An Acupuncturist Mompreneur on Yin Energy, Softness & Building a Business That Actually Fits Your Life

You know how some guests just say the thing you didn't know you needed to hear? This is that episode. Dr. Lisa Upshaw is an acupuncturist, holistic wellness practitioner, and mom of a 14-year-old — and she's been running her own practice since 2006. She's also someone who figured out early on that you have to become two different people to survive this whole mompreneur life. Not fake. Not split. Just intentional about who you're being and when. In this conversation, Malliha and Dr. Lisa get into the real stuff: Yin and Yang energy in business (and why mompreneurs are almost always stuck in Yang), what it actually means to listen to your body, and why so many of us stopped playing long before we had a reason to. They also talk about the "car moment" that five minutes in the driveway before you walk into the house as the unofficial therapy session most moms don't realize they're already having. Dr. Lisa doesn't believe in perfectionism. She doesn't believe in hitting a ceiling someone else set for her. And she's finally, at this point in her life, starting to define what success actually feels like, not what it looks like. Topics covered: * The two-names trick for separating work-you from home-you * Yin vs. Yang energy and where mompreneurs get stuck * Listening to your body's actual cues (not the caffeine or the sugar) * What softness looks like when you're always "on" * The car moment and why it counts as space * Play: what it was, where it went, and how to find it again * Entrepreneurship as liberation * Defining success without anyone else's blueprint About Dr. Lisa: @drlisaupshaw — acupuncturist, TCM practitioner, holistic wellness expert, dancer, astrology student, and mom doing it all on her own terms since 2006.