Ep 4: Anjarae Hamilton - The Through Line

Ep 4: Anjarae Hamilton - The Through Line

Guest: Anjarae Hamilton, Head of Retailer Sales & Account Management at Faire ---------------------------------------- Two engineering degrees. Leads a sales team. Make that make sense. Anjarae Hamilton built the kind of resume that comes with a very specific implied promise: you will go be this thing. Vanderbilt undergrad. Stanford master's. And then she walked away from engineering entirely -- not because she couldn't do it, because she found something that fit better. What followed was consulting at Bain, operations at Caviar, Square, and DoorDash, and eventually Faire, where she now leads retailer sales for one of the most interesting wholesale marketplaces in the country. Kate and Anjarae overlapped at DoorDash, which makes this one feel less like an interview and more like catching up with someone you genuinely admire. Bio:  Anjarae Hamilton is Head of Retailer Sales and Account Management at Faire, where her team works alongside thousands of independent retailers, helping them discover brands, place orders with confidence, and build lasting relationships with the makers they love. She grew up in a small town in Tennessee, where most of the businesses were owned by someone she knew. That early window into Main Street shaped a career spent helping small businesses grow, first at Square, then at DoorDash, and for the last five years at Faire. She lives in Los Angeles with her filmmaker husband, her 4-year-old daughter, and her 2-year-old son. ---------------------------------------- IN THIS EPISODE * 06:19 - How growing up in a small Tennessee town with an Air Force engineering base shaped who she became * 06:45 - What made her choose civil engineering -- and why the reason was more intuitive than logical * 15:09 - How she stumbled into Bain without knowing how competitive it was, and why that might have been the thing that got her in * 17:52 - What consulting gave her that engineering never could: the language, the frameworks, and the ability to influence without authority * 25:27 - The mentor who told her to pay attention to what she read in her free time -- and how that led her to Caviar * 41:49 - Why coming back from maternity leave to build a brand new team was actually easier than returning to her old one * 45:30 - Her annual life OKRs, the vision boarding tradition, and how she thinks about fulfillment without using the word balance * 52:23 - The through line she sees connecting all of it -- and what she tells her mom when she says Anjarae never uses her engineering degree ---------------------------------------- MEMORABLE QUOTES "Throughout every major decision, it would be: here's the pros and cons list rationally, and then how does it feel? Intuitively in my body." "My mom says I don't even use my engineering degree. I'm like -- I do kind of. I'm solving problems." "No one thinks about you as much as you do. I use that to quiet the overthinking, and as a reminder that I have to advocate for myself." "Almost all these decisions are two-way doors. Maybe you choose something and it sucks. You're still going to learn so much and be in a different spot to make a new decision." ---------------------------------------- RESOURCES MENTIONED * Radical Candor by Kim Scott * Faire -- faire.com [http://faire.com] ---------------------------------------- CONNECT WITH ANJARAE LinkedIn: https://www.linkedin.com/in/anjarae/ [https://www.linkedin.com/in/anjarae/] FOLLOW DIRECTION OVER PERFECTION Instagram & TikTok: @directionoverperfection A podcast for early-career professionals, career changers, and parents helping young adults find their footing. Hosted by Kate Crane.

Ep 3: Emma Glazer - Every Decision Is Not a Forever Decision

About This Episode Emma Glazer spent junior year of college interning at a law firm and walked away knowing one important thing about herself: she does not like to argue. That single moment of self-awareness set off a career that has been anything but a straight line — and everything but accidental. In this episode, Emma walks us through nearly two decades of intentional moves: seven years at Target working her way from inventory analyst to beer buyer, an MBA from UC Berkeley's Haas School of Business, six years at DoorDash becoming the go-to voice for the Dasher community, and a director-level marketing role she earned by walking into her future boss's office and making one of the clearest pitches you will ever hear. We also talk about what it looks like to figure out what you need as a whole person — not just a professional — and what comes next when you have the courage to admit the answer has changed. This one is for anyone who has ever looked at their resume and wondered if the path makes sense. It does. You just might not be able to see it yet. ---------------------------------------- What We Cover 04:18 — How Emma decided law was not the right fit — and why trusting that signal early changed everything 09:38 — What seven years at Target actually taught her about problem solving, people management, and professional identity 21:58 — The real reasons she went to business school — and her honest take on whether it was worth it 35:27 — How she ended up on the Dasher team at DoorDash when she was certain she was a merchant and consumer person 39:29 — The Kofi pitch — how she talked her way into a director-level marketing role with a 10-week internship on her resume 46:46 — What the pandemic years at DoorDash felt like from the inside, and why she has never been more motivated before or since 54:09 — The tension between being consumed by work and wanting to be present as a mom and a partner 56:28 — Why she believes we carry a false sense of permanence around career decisions — and what changes when you let that go ---------------------------------------- Emma Glazer Brand marketing consultant working with companies at the intersection of food and technology. Connect with Emma on LinkedIn: https://www.linkedin.com/in/emmarothstein/ [https://www.linkedin.com/in/emmarothstein/] ---------------------------------------- Resources and References UC Berkeley Haas School of Business Target Corporation DoorDash Strava Liquid Death — Emma's pick for best marketing right now ---------------------------------------- About Direction Over Perfection Direction Over Perfection is a podcast for young adults who are trying to figure out what comes next. Not the perfect answer. Not the right title. Just the next right step. Host Kate Crane brings in people who have actually lived the reality of building a career — the pivots, the detours, the moments of doubt, and the moves that changed everything — so you can hear how it really works. New episodes every two weeks. Follow wherever you listen to podcasts. ---------------------------------------- Work With Kate Kate Crane is a private career counselor for young adults. She helps early-career professionals find clarity, build confidence, and make smart moves in today's market — drawing on her own unconventional path from art history major to startup executive. To inquire about one-on-one advising: kate@directionoverperfection.com [kate@directionoverperfection.com]  Follow Direction Over Perfection on Instagram: @directionoverperfection

Ep 2: Megan Stroud - Just Get Going: Megan Stroud on Building a Career in Motion

What happens when you answer a LinkedIn message you almost ignored? Or take a phone call in a janitor's alley at a trade conference when you were supposed to be thinking about starting your own company? For Megan Bohac Stroud, those moments changed everything. Megan Stroud is the CMO of SirDavis American Whisky, an award-winning brand founded by Beyoncé Knowles-Carter in partnership with Moët Hennessy. She joined at inception and helped build it from liquid and bottle design through its global launch, named 2025's Best New Product by Spirits Business. Before SirDavis, she held senior roles at Pernod Ricard and Coca-Cola, spent a year in cannabis, and holds an MBA and PR degree from UT Austin. In 2025, Inc. Magazine named her one of their Top 40 Entrepreneurial CMOs of the Year. Her career did not follow a straight line, and that is exactly the point. In this episode, Megan and Kate dig into the pivots, the moments of doubt, the cold calls she almost did not answer, and the philosophy that eventually tied it all together: momentum brings clarity. --- WHAT WE COVER 01:21 — What a CMO at a brand-new startup actually does, from pop-up activations to five-year inventory forecasts 05:47 — What Megan walked into when she joined SirDavis: not a brand, not a bottle. Just an idea. 22:53 — The LinkedIn message she almost ignored and the exact moment the universe made it make sense 32:24 — A phone call in a janitor's alley and how SirDavis found her before she found it 37:56 — Momentum brings clarity: the bike metaphor and why the next step is the only one that matters 46:36 — The rope swing: why relationships matter more than being the perfect candidate on paper --- QUOTES WORTH WRITING DOWN "A little bit beyond mediocre is noticed. No matter what the position, you can do it with integrity." "Momentum brings clarity. If you go too slow on a bike, you wobble. Get going." "It's not a ladder. At some point somebody's going to throw a rope swing to you. Grab it." "Every action you take is a vote for the type of person you want to become." — James Clear "Don't dim that inner knowing. If you listen to it, options will unfold for you." --- RESOURCES AND MENTIONS SirDavis American Whisky — sirdavis.com [http://sirdavis.com] The Honeybee cocktail — sirdavis.com/our-cocktails/honey-bee [http://sirdavis.com/our-cocktails/honey-bee] Atomic Habits by James Clear GLG — Gerson Lehrman Group, one of the world's largest expert networks --- FOLLOW AND CONNECT Follow Direction Over Perfection wherever you listen to podcasts. To work with Kate one-on-one, visit directionoverperfection.com [http://directionoverperfection.com] or email kate@directionoverperfection.com [kate@directionoverperfection.com]. Find SirDavis at sirdavis.com [http://sirdavis.com]. Direction Over Perfection is hosted by Kate Crane, a private career counselor for young adults and early-career professionals. Kate helps people find clarity, confidence, and their next right step, even when the path is not yet clear.

Ep 1: Brooks Miller - Direction, Not Destination, Building a Career and a Life at the Same Time

Ep 1: Brooks Miller, EVP, Creators @ Edelman & UEG Direction, Not Destination: Building a Career and a Life at the Same Time Direction Over Perfection with Kate Crane · 45–60 min ABOUT THIS EPISODE Brooks Miller has one of the most interesting careers in the creator economy — and it started with a child acting agent in Dallas, Texas. From local commercials to the University of Texas, from an advertising internship in LA to a front-row seat as influencer marketing was invented in real time at Twitter, Brooks' path was never obvious. It was curious, intentional, and guided far more by instinct than by plan. Then Elon Musk bought Twitter. Five months postpartum, back at work for three weeks, Brooks got the axe along with thousands of colleagues. And she landed somewhere better. Today she's EVP of Creators at Edelman & UEG, leading creator strategy for some of the world's most recognized brands across a team of nearly 200 people globally. In this conversation, Kate and Brooks talk about what it really means to build a career in a field that didn't exist when you were in college, how geography and love shaped every major move, what it's actually like to be laid off and come back stronger, and why the best advice she's ever received is: nobody thinks about you as much as you think about you. IN THIS EPISODE 00:00 — The child actor origin story and how it shaped everything that came after 08:20 — UT Austin, an advertising degree, and the agency tour that launched her career 16:29 — Moving to San Francisco for love — and falling obsessed with tech 19:47 — The Instagram moment that made her realize everything was about to change 22:11 — Joining Twitter to invent a job that didn't have a name yet 25:33 — The layoff — and two practical tips for being layoff-proof nobody tells you 38:53 — Parenting, partnership, and building a village that makes it all work 45:59 — What she'd tell her 2010 self — and why the best careers don't make sense until they do QUOTES FROM THIS EPISODE * "No career is a permanent sentence." — Brooks Miller * "Nobody thinks about you as much as you think about you. And in some circumstances, that is so freeing — it allows you to take bigger risks and listen to your gut a little more." — Brooks Miller * "Everything is data. Even taking a coffee with someone is data. That's so much more valuable than being right — whatever right means." — Brooks Miller RESOURCES + LINKS MENTIONED * Book: The 15 Commitments of Conscious Leadership — Jim Dethmer * Cannes Lions: Brooks and the Edelman Creator team will be at Cannes — reach them at CreatorAtCannes@edelman.com [CreatorAtCannes@edelman.com] CONNECT WITH BROOKS * LinkedIn: linkedin.com/in/brooksdennardmiller [http://linkedin.com/in/brooksdennardmiller] * TikTok: tiktok.com/@brooksiedm [http://tiktok.com/@brooksiedm] LISTENER REFLECTION Where in your career are you waiting for permission to make a move you already know you want to make? FOLLOW THE SHOW If this conversation resonated with you, follow Direction Over Perfection wherever you listen to podcasts — it helps more people like you find the show. New episodes drop every other Tuesday. And if you're a parent helping a young adult find their footing, share this episode with them. Sometimes the most helpful thing you can do is show someone a path they didn't know was possible.