From Third-Grade Teacher to Global Entrepreneur in Midlife

From Third-Grade Teacher to Global Entrepreneur in Midlife

Gina realized teaching no longer fit, but the bigger pull was her desire to live abroad and build a life that felt more expansive than the one she had in Atlanta. This episode follows how that desire led her from the U.S. classroom to the Philippines, then into digital nomad life, expat living, and a location-independent business. Gina Oliver shares how she and her husband chose the Philippines, learned to navigate visas, housing, remote work, and culture shock, and eventually built Wave Enterprise into a location-independent podcast and social media studio. The conversation also gets practical about building a career abroad, finding community as an expat, and making your work support the lifestyle you actually want. ABOUT THE GUEST: Gina Oliver is the co-founder of Wave Enterprise Co, a location-independent podcast & social media management studio for female-owned wellness brands. After 7 years abroad, she’s unlearned a lot of societal norms & identified her core values: community, wellness, & connection. She hopes to inspire others to live well through her work & podcast, Ripple FX. WHAT YOU WILL LEARN: * (00:01:59) What teacher burnout actually looked like — and the decision to move abroad in search of a more expansive life * (00:03:34) How she and her husband chose the Philippines, downsized their life in Atlanta, and funded the move * (00:07:23) "Who am I without this job?" — the identity reset that comes with leaving a career you trained for * (00:16:34) Unlearning hustle culture from the inside out, and what shifted once she stopped performing productivity * (00:25:24) The emotional pattern of every big move — fear, grief, then the synchronicities — and how to trust it * (00:34:21) Building expat community from scratch: why it's non-negotiable, and the rooms she walked into first * (00:39:06) Practical considerations of life abroad — the financial realities, cost-of-living trade-offs, housing, Wi-Fi, healthcare, and running a business with a spouse * (00:42:00) How Wave Enterprise became a location-independent podcast and social media studio — and how she designed the work to support the life * (00:45:45) "Today is the day." — Gina's mantra and her one piece of advice for the woman still waiting GUEST OFFER: If you’re interested in building a life abroad, or you’re currently growing a business through social media and podcasting, you can book a free virtual coffee chat [https://calendly.com/waventerpriseco/get-to-know-you-coffee-chat] with Gina. She'd love to connect! GUEST LINKS: * Instagram: https://www.instagram.com/waventerpriseco/ [https://www.instagram.com/waventerpriseco/] * LinkedIn: https://www.linkedin.com/in/wellnesssocialmedia/ [https://www.linkedin.com/in/wellnesssocialmedia/] * Website: https://waventerprise.co/ [https://waventerprise.co/] * Podcast Ripple FX: https://open.spotify.com/show/0IeEWDyizz9idw4GPUaGrv?si=1a6cac7950be4383 [https://open.spotify.com/show/0IeEWDyizz9idw4GPUaGrv?si=1a6cac7950be4383] CONNECT WITH SPONSOR: Roots & Bloom * Instagram @ [https://www.instagram.com/rootsbloom_studio/]rootsandbloom_studio [http://@rootsandbloom_studio] * Listener promotion: Roots & Bloom 20% off plant purchase — mention “Her Intentional Reset” at checkout/to Ciera Curtis CONNECT WITH HIR * Instagram @ herintentionalreset.co [https://www.instagram.com/herintentionalreset.co/] * Facebook @ Her Intentional Reset.co [https://www.facebook.com/profile.php?id=61587329908947] * Website: www.herintentionalreset.com [https://herintentionalreset.com/?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGntCEey4YretrZ39A7mINUiy-Dmz7iRv0BDLhY2OcDQkfqMmMGK8--zTX20RE_aem_d_YskQDM9KyDWyA-8dxVVw] * Her Intentional Reset Experience: the Artist's Way Creative Cluster - Join here [https://www.facebook.com/groups/herintentionalresetexperience] * More information on HIRE: the Artist's Way Creative Cluster [https://www.instagram.com/p/DZFuTbGjdqS/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==] * The Artist’s Way by Julia Cameron - Amazon link [https://a.co/d/09E1ps0J] RESOURCES MENTIONED IN THIS EPISODE: * Girl Gone International (GGI): https://girlgoneinternational.com [https://girlgoneinternational.com] * Digital Nomad Visa: https://www.globalcitizensolutions.com/digital-nomad-visa/ [https://www.globalcitizensolutions.com/digital-nomad-visa/] * The Daily Dharma podcast: https://thedailydharma.buzzsprout.com [https://thedailydharma.buzzsprout.com] * Workaway: https://www.workaway.info [https://www.workaway.info] * Wise (international money transfers): https://wise.com [https://wise.com] * Time Buddy / World Time Buddy: https://www.worldtimebuddy.com [https://www.worldtimebuddy.com] If HIR has been valuable to you, you can support the show here: Kofi Support The Show [https://ko-fi.com/herintentionalreset] * No pressure — just making it easy for listeners who want to say so. Music from #Uppbeat (free for Creators!): * https://uppbeat.io/t/hemlock/the-way-forward [https://uppbeat.io/t/hemlock/the-way-forward] * License code: RVGOVVHKDJFBKVJC This post contains affiliate links. If you purchase through my link, I may earn a small commission at no additional cost to you. I only recommend books and resources discussed on the show and I genuinely use and believe in.

An Executive Coach on Facing Fear, Pivoting Careers, and Protecting Your Energy | Carrie Fabris, Career Frame

At home with her young kids, Carrie found herself with the space to ask a question a lot of women in midlife quietly carry: if I could do anything I wanted, what would it be? The honest answer didn't fit the career she'd already built — and figuring out what to do about that took more than one try. ABOUT THE GUEST: Carrie Fabris spent 20+ years in corporate leadership at companies like Google, Travelocity, and Sabre before leaving to start her coaching firm, Career Frame. When it didn't take, she went back to corporate for two years — then relaunched, this time to make it stick. Now an executive coach and author of All In: A Working Mom's Unapologetic Quest for a Juicy Life, she works with senior leaders and teams, but the same lessons apply just as much to a working mom wondering what's next or trying to avoid burnout — including her "Return on Energy" idea: like ROI, but for your energy — are you getting a worthwhile return on what you pour into something, even if the payoff is down the road? WHAT YOU WILL LEARN: * [04:02] Why her first attempt at leaving corporate failed — and why she had to go back before she could move forward * [11:07] What “all in” really means — the idea behind her book All In: A Working Mom’s Unapologetic Quest for a Juicy Life * [17:46] How to use her FRAME It executive-coaching framework at home — whether you’re leading a team at work or managing your own energy as a busy mom * [22:57] The Return on Energy framework — a simple gut-check for where your time and energy actually go * [26:11] The “busy” red flag, and the questions to ask yourself when you can't slow down * [32:53] How to use your Clifton Strengths to find work that actually energizes you * [42:05] Setting Your Rate — Why Carrie Doesn't Charge Hourly GUEST OFFER: Complimentary leadership quiz — “Discover Your Frame It Method Leadership Style” [https://carriefabris.myflodesk.com/theframeitmethodquiz] RESOURCES: * All In: A Working Mom's Unapologetic Quest for a Juicy Life — Amazon link [https://amzn.to/4uVKveU] * The Artist’s Way by Julia Cameron - Amazon link [https://a.co/d/09E1ps0J] * Clifton Strengths - Amazon link [https://amzn.to/4fr6sO1] GUEST LINKS: Wildflower Macarons * Careerframe.com: https://careerframe.com/ [https://careerframe.com/] * Instagram: @cdfabrice [https://www.instagram.com/cdfabris/] (primary) * Instagram: @CareerFrame [https://www.instagram.com/careerframe/] * LinkedIn: Career Frame [https://www.linkedin.com/company/careerframe-llc/] * LinkedIn: Carrie Fabris [https://www.linkedin.com/in/cfabris-reframe-coaching-training/details/experience/] CONNECT WITH SPONSOR: Roots & Bloom * Instagram @ [https://www.instagram.com/rootsbloom_studio/]rootsandbloom_studio [http://@rootsandbloom_studio] * Listener promotion: Roots & Bloom 20% off plant purchase — mention “Her Intentional Reset” at checkout/to Ciera Curtis CONNECT WITH HIR * Instagram @ herintentionalreset.co [https://www.instagram.com/herintentionalreset.co/] * Facebook @ Her Intentional Reset.co [https://www.facebook.com/profile.php?id=61587329908947] * Website: www.herintentionalreset.com [https://herintentionalreset.com/?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGntCEey4YretrZ39A7mINUiy-Dmz7iRv0BDLhY2OcDQkfqMmMGK8--zTX20RE_aem_d_YskQDM9KyDWyA-8dxVVw] If HIR has been valuable to you, you can support the show here: Kofi Support The Show [https://ko-fi.com/herintentionalreset] * No pressure — just making it easy for listeners who want to say so. Music from #Uppbeat (free for Creators!): * https://uppbeat.io/t/hemlock/the-way-forward [https://uppbeat.io/t/hemlock/the-way-forward] * License code: RVGOVVHKDJFBKVJC This post contains affiliate links. If you purchase through my link, I may earn a small commission at no additional cost to you. I only recommend books and resources discussed on the show and I genuinely use and believe in.

The Artist's Way at 40: One Woman's Unexpected Second Act | Calleen De Oliveira, Ep. 12

You’re good at your job, you’re juggling everything, and somewhere underneath all of it there’s a quiet question you haven’t answered yet: what do I actually want to do next? The problem isn’t that you don’t know how to work hard — it’s that no one ever taught you how to listen to yourself. ABOUT THIS EPISODE: In this episode, Molly shares how The Artist’s Way by Julia Cameron kept showing up in her life right when she needed it — and why that’s not as mystical as it sounds. Then she brings in Calleen De Oliveira, who used this exact book in her 40s to leave a 25-year advertising career, go to nursing school, and build a life she is proud of. What came out of those morning pages surprised even Calleen — and it went far beyond a career change. Plus: Molly announces the first Her Intentional Reset Experience: The Artist’s Way Creative Cluster, and is giving away eight copies of the book to listeners who want to join. WHAT YOU WILL LEARN: * [01:15] The three-day sequence that convinced Molly this book was worth paying attention to — and the neuroscience that explains why it happened * [06:52] What The Artist’s Way actually is — and why it’s not just for people who want to paint * [13:22] What morning pages did for Calleen that nothing else could: nursing school, sobriety, and a marriage she almost lost * [19:01] What a real Creative Cluster looks like — Calleen’s group of eight women stayed together for a decade * [24:15] The right mindset to bring into this 12-week practice (and what Calleen says to anyone who doesn’t want to commit) * [32:09] How to join the very first Her Intentional Reset Experience — The Artist’s Way Creative Cluster — and how to win one of eight free copies of the book RESOURCES: * "The Artist's Way" by Julia Cameron | Amazon Link [https://a.co/d/09E1ps0J] * "The Right to Write" by Julia Cameron | Amazon link here [https://amzn.to/49wcc5i] * Julia Cameron 12-Week Virtual Guide — will be available for HIRE: The Artist's Way Creative Cluster participants only. PODCAST REFERENCES: * Episode 11 [https://player.captivate.fm/episode/e4569537-51b1-4eda-a2ef-48e79a0888a3/]: HIR From Wall Street to Fashion Founder, Jennifer Conrad, Twigs * Episode 8 [https://player.captivate.fm/episode/a81d5444-53a5-4ca6-bb18-b610eac6eafe/]: HIR From Spotify Exec to Solo Founder, Courtney Reimer * Mel Robbins Podcast [https://podcasts.apple.com/us/podcast/the-mel-robbins-podcast/id1646101002?i=1000725966492]: (on Reticular Activating System - RAS) 8 Things to Tell Yourself Every Morning Her Intentional Reset Experience (HIRE): The Artist's Way Creative Cluster * Sign up for HIRE at: Her Intentional Reset Experience: the Artist's Way Creative Cluster - Facebook Private Group [https://www.facebook.com/groups/herintentionalresetexperience] * Book giveaway details and entry link follow on Instagram / Facebook at herintentionalreset.co (Winners will be announced on Saturday, June 6th, 2026) * Instagram @ herintentionalreset.co [https://www.instagram.com/herintentionalreset.co/] * Facebook @ Her Intentional Reset.co [https://www.facebook.com/profile.php?id=61587329908947] * Website: www.herintentionalreset.com [https://herintentionalreset.com/?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGntCEey4YretrZ39A7mINUiy-Dmz7iRv0BDLhY2OcDQkfqMmMGK8--zTX20RE_aem_d_YskQDM9KyDWyA-8dxVVw] LOGISTICS: Her Intentional Reset Experience (HIRE) * Week 1 starts June 15th, 2026 – Week 12, Aug. 31st * June 17th, 2026 first virtual meeting * Bi-weekly virtual meetings through end of August * Come when you can. No pressure, no perfect attendance, no guilt. If HIR has been valuable to you, you can support the show here: Kofi Support The Show [https://ko-fi.com/herintentionalreset] * No pressure — just making it easy for listeners who want to say so. Music from #Uppbeat (free for Creators!): * https://uppbeat.io/t/hemlock/the-way-forward [https://uppbeat.io/t/hemlock/the-way-forward] * License code: RVGOVVHKDJFBKVJC This post contains affiliate links. If you purchase through my link, I may earn a small commission at no additional cost to you. I only recommend books and resources I genuinely use and believe in.

Curating a Career Pivot and a Life That Fits | Jennifer Conrad, Founder & President Twigs, Ep. 11

From Wall Street trader to fashion entrepreneur, Jennifer Conrad moved from New York to Madison, WI, on September 11, 2001. While coping with the events of that day, Jennifer identified a need in her new city — and a vision for what to do next. So she did what a former day trader would do: she trusted her gut, moved quickly, and built it herself. Jennifer, Founder & President of Twigs, an elevated, fashion boutique, will discuss how she built this career pivot on instinct and discipline, how she's kept the business strong through pandemics and recessions for two decades, the importance of prioritizing your people, and what she's learned about building both a career and a life that fit. ABOUT THE GUEST: Twigs is an independent women's fashion boutique with locations in Madison and Brookfield, WI, with a nationwide online presence at shoptwigs.com. Jennifer opened Twigs on January 2002, drawing on the economics degree she earned at Columbia and a career as a money market trader at Citigroup. In 2012, Elle Magazine recognized Twigs as one of the best boutiques in America. What make’s Twigs stand the test of time is Jennifer’s approach to curation: a thoughtful mix of contemporary clothing, jewelry, and accessories for three generations of women — carefully pulling together pieces that are worth your time and attention. What keeps customers coming back is the Twigs team's ability to cultivate a community while providing exceptional customer service and attention to the little details. WHAT YOU WILL LEARN: * 08:49 — Spotting a need in a field you didn't come from — and deciding to act on it * 11:52 — How Jennifer uses her background as a trader to assess risk and make fast decisions when the business needs to pivot * 13:32 — The "big enough and small enough" philosophy that has shaped how she's grown — staying nimble while building real durability through a pandemic and a recession * 24:04 — When to take the leap to expansion — and how a candid conversation with another retailer helped her say yes to a second store * 34:25 — Jennifer's leadership style and why appreciating her team is the foundation of everything * 39:13 — The art and joy of curating — how Jennifer finds designers, edits a collection, and curates for three generations of women * 49:08 — What it takes to keep a business healthy over the long haul, including the team and the benefits that have kept her people with her * 50:55 — Jennifer's honest advice for any woman thinking about a real industry jump * 56:11 — Learning to take care of yourself in order to be there for others GUEST LINKS: * Website: www.shoptwigs.com [https://shoptwigs.com/] * Instagram: @shoptwigs [https://www.instagram.com/shoptwigs/] * Email: info@shoptwigs.com ADDITIONAL RESOURCES: * "The Artist's Way" by Julia Cameron, Amazon link here. [https://amzn.to/4v0RiUa] * Note, by using the link HIR will receive a small affiliate link compensation. CONNECT WITH SPONSOR: Roots & Bloom * Instagram @ [https://www.instagram.com/rootsbloom_studio/]rootsandbloom_studio [http://@rootsandbloom_studio] * Listener promotion: Roots & Bloom 20% off plant purchase — mention “Her Intentional Reset” at checkout/to Ciera Curtis CONNECT WITH HIR * Instagram @ herintentionalreset.co [https://www.instagram.com/herintentionalreset.co/] * Facebook @ Her Intentional Reset.co [https://www.facebook.com/profile.php?id=61587329908947] * Website: www.herintentionalreset.com [https://herintentionalreset.com/?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGntCEey4YretrZ39A7mINUiy-Dmz7iRv0BDLhY2OcDQkfqMmMGK8--zTX20RE_aem_d_YskQDM9KyDWyA-8dxVVw] If HIR has been valuable to you, you can support the show here: Kofi Support The Show [https://ko-fi.com/herintentionalreset] * No pressure — just making it easy for listeners who want to say so. Music from #Uppbeat (free for Creators!): * https://uppbeat.io/t/hemlock/the-way-forward [https://uppbeat.io/t/hemlock/the-way-forward] * License code: RVGOVVHKDJFBKVJC

How She Turned a Hobby Into a Business While Caregiving | Jenny Huynh, Wildflower Macarons, Ep. 10

You've got a hobby you can't stop doing. But between the caregiving, the family, the life that's already full, you're not sure there's room for it to become anything more — or if you're even allowed to find out. A gentle note before you listen: this episode includes Jenny's experience with postpartum depression and suicidal thoughts. If that's a tender topic for you, please take care with this one. Support resources are linked below. ABOUT THE GUEST: Jenny Huynh is the baker behind Wildflower Macarons, a home-based small business in Eden Prairie, Minnesota that she started in 2020 during a postpartum she didn't yet have a name for. Five years in, she's grown it from a kitchen hobby into a custom-order business known for intricate, hand-painted novelty macarons inspired by her Southeast Asian heritage — all while being the primary caregiver for her father-in-law and raising her own son. Her story is a real look at what it takes to grow a small business in midlife when life keeps adding to your plate, not subtracting from it. WHAT YOU WILL LEARN: * [00:02:20] How a birthday party started a business — with zero initial plan * [00:05:33] What postpartum looked like for Jenny as a new mom, and why we all need to share our experiences * [00:13:20] Going from kitchen hobby to officially licensed cottage food business — and why it was easier than she expected * [00:16:06] The sandwich generation reality: raising her son and caregiving for her father-in-law while running a business * [00:21:00] How she used her macarons to raise money for community rent during ICE raids — and why every role matters, no matter how small * [00:30:01] The strength her husband sees in her that she didn't see in herself * [00:31:53] The advice she'd give her younger self: why she's "more than enough" GUEST OFFER: Wildflower Macarons is generously offering Her Intentional Reset listeners 10% off first-time customer order. Reach out and mention Her Intentional Reset podcast. All details below. GUEST LINKS: * Instagram: @wildflowermacarons [https://www.instagram.com/wildflowermacarons/] * Website: wildflowermacarons.com [https://www.wildflowermacarons.com/] * 10% off first-time customer discount code — "Welcome10" CONNECT WITH SPONSOR: * Instagram @ [https://www.instagram.com/rootsbloom_studio/]rootsandbloom_studio [http://@rootsandbloom_studio] * Listener promotion: Roots & Bloom 20% off plant purchase — mention “Her Intentional Reset” at checkout/to Ciera Curtis CONNECT WITH HIR * Instagram @ herintentionalreset.co [https://www.instagram.com/herintentionalreset.co/] * Facebook @ Her Intentional Reset.co [https://www.facebook.com/profile.php?id=61587329908947] * Website: www.herintentionalreset.com [https://herintentionalreset.com/?utm_source=ig&utm_medium=social&utm_content=link_in_bio&fbclid=PAZXh0bgNhZW0CMTEAc3J0YwZhcHBfaWQMMjU2MjgxMDQwNTU4AAGntCEey4YretrZ39A7mINUiy-Dmz7iRv0BDLhY2OcDQkfqMmMGK8--zTX20RE_aem_d_YskQDM9KyDWyA-8dxVVw] COMMUNITY CAUSES * PROP (People Reaching Out to People): https://propfood.org/ [https://propfood.org/] ADDITIONAL LINKS * Postpartum Support International: postpartum.net [https://postpartum.net/] | helpline 1-800-944-4773 If HIR has been valuable to you, you can support the show here: Kofi Support The Show [https://ko-fi.com/herintentionalreset] * No pressure — just making it easy for listeners who want to say so. Music from #Uppbeat: https://uppbeat.io/t/hemlock/the-way-forward [https://uppbeat.io/t/hemlock/the-way-forward] * License code: RVGOVVHKDJFBKVJC