Side Hustles for Teachers: Why You Shouldn't Need One — and Why You Deserve One

Teacher Boundaries and Knowing When to Say No: Union Work and Online Summits — with Bryson Tarbet of That Music Teacher

Bryson Tarbet is a former PreK–6 music teacher and the founder of ThatMusicTeacher.com and Tarbet Education Network, where he builds content-specific professional development for music and arts specialists. He's also one of the earliest supporters of Teachers With Money — someone who helped Christa workshop the mission months before this show was live. This is a conversation between two former elementary music teachers who both stepped out of the classroom and never stopped fighting for the people still in it. Bryson coined a phrase for something a lot of teachers feel but can't quite name: the Specialist's Burden — the isolation of being the only one doing your job in the building, with no team and no support built for your content. From there the conversation opens into the bigger setup underneath it: the story that your sacrifice is your value, that asking for more somehow makes you a worse teacher. Bryson and Christa trace that same story across three levels — the classroom, the business, and the bargaining table — and land on the one boundary every teacher can start practicing tomorrow. This episode covers: * The Specialist's Burden — why being the only music, art, or PE teacher in your building leaves you isolated and underserved by general PD, and why naming it out loud is the first move toward fixing it * "Do it for the kids" as systemic gaslighting — how a phrase that sounds noble puts the whole broken system on teachers' shoulders, and Bryson's reframe that flips it: teacher working conditions are student learning conditions * The charging guilt that follows you out of the classroom — why "I should just give it away for free" is the same voice that ran you ragged in the room, and how Bryson made peace with charging by anchoring to his values: inclusivity, community empowerment, advocacy * Inside the summit model — how free access funds paid access funds free initiatives, and why putting it all on the table (no sneaky tactics, "we can still be friends if you don't upgrade") is both the kinder and the more sustainable way to sell * Paying speakers fairly — how Bryson moved from affiliate-only to a base-pay-plus-affiliate hybrid so it's not only the big audiences that get paid, and how he coaches first-time speakers to leverage the opportunity * The collective layer — Bryson's years as a union rep and then VP, what he saw on the negotiations team during a contract year that came right up to a strike, and why individual mindset work and collective action are the same conversation, not either/or * Where to start if you've never opened your contract — read it, know it word for word, and remember that a union is only as strong as the people in it * The one walkaway: it's okay to say no — why saying no is the boundary that protects both your health and your career, and how it pushes the system to deal with what it's been quietly offloading onto teachers 🎵 Music teacher friends: Join us for the Summer 2026 Elementary Music Summit! [https://christa_jones--thatmusicteacher.thrivecart.com/all-access-pass-jul26-fa/]*   Connect with Bryson: ThatMusicTeacher.com — for elementary music teachers [https://thatmusicteacher.com] Tarbet Education Network — for arts specialists [https://tarbeteducationnetwork.com] @thatmusicteacher (Instagram) [https://www.instagram.com/thatmusicteacher/] Bryson Tarbet (LinkedIn) [https://www.linkedin.com/in/bryson-tarbet] *This is an affiliate link — Christa may earn a commission if you register through it, at no additional cost to you. 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Teaching Abroad and Building a Side Hustle as a Financial Strategist — with Kennedi Crosby

Kennedi Crosby is a secondary math teacher with six years in the classroom, and a journey most teachers don't get to live. She has taught in New Orleans, Washington D.C., Kuwait, and now China. Somewhere along the way, she also became a financial strategist working specifically with teachers: walking them through the kind of financial education most of us never got. This episode moves through her winding path. From biochemistry pre-med at an HBCU, to teaching algebra in New Orleans. To the international classroom in Kuwait. Through the brutal reverse culture shock of coming home to the U.S. job market — over two hundred applications, less than ten interviews, a year and a half of stringing together seven jobs at once. And into her current dual life: math teacher in China + financial strategist for teachers stateside. Part travel story, part U.S. system reality check, part very practical money advice from someone who learned it the hard way. This episode covers: • Kennedi's path from biochemistry pre-med to math teacher  • What teaching internationally actually looks like — IB curriculum, 48-hour offer letter decisions, schools that start their hiring cycle in September, and the contract realities most U.S. teachers don't know about • The reverse culture shock of coming home: why returning to the U.S. job market after teaching abroad was harder than the original move • Seven jobs at once: tutoring, bartending, nannying, online teaching platforms, what a year and a half of stringing it all together actually looks like with no salary, no benefits, no safety net • How Kennedi became a financial strategist — a LinkedIn outreach from another educator that opened a new chapter of her teaching life • What a financial strategist actually does (a "thought partner" for your money) and what a first conversation with one looks like in practice • The generational money advice gap — why what worked for our parents and grandparents won't get you to retirement on a teacher's salary in 2026 • Pay yourself first: the one shift Kennedi most wants teachers to make next, and why it has to come before everything else 🍏 Heads up: this episode contains (very!) brief adult language. Tagged E for explicit. Connect with Kennedi: linkedin.com/in/kennedi-crosby [https://www.linkedin.com/in/kennedi-crosby-/] Kennedi Crosby works as a financial strategist with the Miliare Group. Always consult a licensed financial professional before making significant financial decisions. 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.

From Credit Card Debt to Financial Confidence: An Educator's Story with Rose Mendonca of Teacher Talks Money

If you're a teacher carrying credit card debt right now — the kind that sits in your chest at 2am — this episode is for you. Rose Mendonca is a 26-year educator, school counselor, and the founder of Teacher Talks Money, a financial education platform built for teachers by a teacher. She climbed out of credit card debt on a teacher's salary, paid off her mortgage years ahead of schedule, and built her platform without ever leaving the classroom. Rose's story is the spine of this conversation. The credit card trap she fell into as a first-gen college student. The merged-household debt she and her husband carried into newlywed life. The five to seven years of consistency it took to get out. And the single habit that did the most heavy lifting: automation. Plus the three steps Rose teaches educators to go from a $36,000 salary to a million dollars, the number one retirement mistake she sees teachers make, and why she believes every teacher should open a Roth IRA — even while still in debt. This episode covers: • Rose's debt story: the credit card trap that started in college, the merged-household debt of early marriage, and the five to seven years of consistency it took to climb out • The first move that did the heavy lifting: automation, and the specific weekly cadence Rose used to turn $50 a paycheck into seven figures • Rose's counterintuitive take on debt vs. investing: why she tells every teacher (even those in serious debt) to open a Roth IRA and start funding it with $50, before clearing the credit card balance • The 403(b)/457 conversation: how to find what your district offers, the fee question that quietly costs teachers hundreds of thousands of dollars, and the bad actors to watch out for • The pension myth: why "my pension will cover it" is the number one retirement mistake Rose sees teachers make • Building Teacher Talks Money while staying inside education — proof that financial confidence doesn't require leaving the work you love 🍏 Books mentioned in this episode: Your Money or Your Life by Vicki Robin · Clever Girl Millionaire by Bola Sokunbi Connect with Rose: @teachertalksmoney [https://www.instagram.com/teachertalksmoney/] (Instagram) linkedin.com/in/rose-mendonca [https://www.linkedin.com/in/rose-mendonca] (LinkedIn) teachertalksmoney.com [https://teachertalksmoney.com] Rose Mendonca is the founder of Teacher Talks Money and offers financial education and coaching. Always consult a licensed financial professional before making significant financial decisions. 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Side Hustles for Teachers: Why You Shouldn't Need One — and Why You Deserve One

If you're a teacher and you're tired — bone-deep, paycheck-to-paycheck tired — this episode opens with the sentence you need to hear: it's not your fault. The math hasn't been mathing for a long time. The system that's supposed to support the people who shape every future generation has been quietly underpaying you for decades. And then it pivots. Christa names what most teachers have been told to keep quiet about: you were never supposed to be broke, wanting wealth doesn't make you ungrateful, and building a side income is not selling out. It's surviving. It's thriving. It's refusing to wait for the system to catch up. This episode covers: • The teacher pay gap by the actual numbers — 27% less in weekly wages than other professionals with comparable degrees, and the gap widening (not closing) over the last decade. • The script teachers were handed and never asked for — "teachers don't do it for the money" as a personal ceiling on what you're allowed to want. • Why side hustles aren't hustle culture — the difference between grinding yourself into burnout and building something on your own terms that gives you breathing room, choices, and a real safety net. • The counterintuitive truth — a side hustle can give you energy BACK, not just take it. And for a lot of teachers, it's the thing that actually makes staying in the classroom sustainable. • A first taste of what's coming on the show — real teachers building real income streams (TPT, tutoring, curriculum writing, coaching, consulting, content) without leaving the classroom they love. 🍏 If this hits home, share it with a teacher who needs to hear "it's not your fault" today. That's how this grows — teacher to teacher. 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Career Growth for Teachers Who Want More Options: Teacher Career Cheat Codes with Courtney Johnson

Courtney Johnson is a career content creator, personal brand strategist, and the author of Career Cheat Codes. She's also Christa's personal brand mentor, business coach, and the person who helped her build the thing you're listening to right now. In this conversation: why teachers should work louder (not harder), and the smallest possible step toward building a personal brand. Plus: cringe mountain, why receiving compliments is the same muscle as receiving money, and Courtney's exact starter pack for anyone who wants to start posting online but doesn't know where to begin. This episode covers: • The case for working louder: why staying visible matters more than staying late, and how teachers can practice it without feeling like they're bragging. • Cringe mountain: the gap between where you are and where you want to be, and why everyone who's already up there had to climb it themselves. • Career advice that actually translates for teachers: most of it assumes a corporate ladder. What the cheat codes look like when your path isn't a ladder. • Receiving compliments → receiving money. Why one is the practice muscle for the other, and what teachers can do this week to start. • The personal brand starter pack: pick one platform. Post one time a week. For one year. That's it. Connect with Courtney: @courtlynnjohnson (Instagram) [https://www.instagram.com/courtlynnjohnson/] @courtlynnjohnson (TikTok) [https://www.tiktok.com/@courtney..johnson] Courtney Johnson (LinkedIn) [https://www.linkedin.com/in/courtneylynnjohnson/] Career Cheat Codes (Penguin Random House) [https://www.amazon.com/Career-Cheat-Codes-Unconventional-Unfiltered/dp/0593840054/ref=sr_1_1?crid=1F2HVYHADBBQW&dib=eyJ2IjoiMSJ9.A4aOyZ70enp7-Umpb_J46dYiRRz9sy1tYSUAO_X0Qmbr8gjbc1UJtRL0j1FDoG2c92cZrjDBKKwEoWYNV1u5zeJb1jU2n-dEsdbfqJ7OFyUXOmKw_uTfcBaMqmp9JHThfRlS2mRnMBALBJ0cpUgTOj2V86KfbWnU-hji73AJGR-SsZKputu04cUi6V6p6fTRhIfopI-l_0KJARE4Gx2oR9bZ4K0RasUv-i3Xk2uC6Hw.P1fEmr6Jc2QkI4uqoYF5xSVA_jL3FgGSTP_reZknSuo&dib_tag=se&keywords=career+cheat+codes&qid=1778553401&sprefix=career+cheat+codes%2Caps%2C204&sr=8-1] 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.