October Theory: Fresh Starts Aren’t Just for January (Solo Episode)

Text Kristen your thoughts or feedback about the showIt’s Thanksgiving week — the season of gratitude, chaos, & calendars that somehow manage to fill themselves.If you’ve ever said, “I can’t use an online scheduler… my schedule’s always changing!” or “I don’t want to be boxed in!” — this one’s for you.I’m busting the biggest myths about online scheduling & showing you how a scheduling link doesn’t take away your freedom — it protects it.Spoiler alert: an online scheduler can help you set clear boundaries, avoid double-booking, & give clients an easier way to connect — all while saving you hours each week.If you’ve been hesitant to share your calendar, you’ll leave this episode ready to set one up — and finally feel like your schedule is working for you, not against you.*** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showAuthor and entrepreneur Charity Alyse shares the heartwarming story behind Austen’s Shelf, her tiny bookshop on wheels — a Jane Austen–inspired mobile bookstore bringing literary magic to communities across New Jersey.After a health scare reminded her that “someday” isn’t guaranteed, Charity decided to stop waiting and start building. Within weeks, she and her husband transformed a simple trailer into a charming, book-filled escape — complete with wallpaper, shelves, and the warmth of Jane Austen’s parlor.In this episode, Charity shares ALL the details of learning how to run a bookstore — budgeting, inventory, and the steep logistics of transporting and setting up hundreds of books. She also shares the lessons she’s learned about knowing your audience, building community, and staying calm when everything goes sideways (including losing the keys to her bookshop on launch day).Her story is a beautiful reminder that courage, curiosity, and persistence can turn even life’s scariest moments into something extraordinary — and that sometimes, the fairytale begins when you stop waiting for “someday.”Connect with Charity at austensshelf.com or on Instagram (@austensshelf | @charityalyse)*** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showIt’s National Checklist Day, which might as well be my personal holiday! In this episode, I’m sharing the tools that keep my solopreneur business organized, my brain calm (mostly), & my systems running smoothly.From my digital checklist in Asana, to client management made easy with 17hats, to two years of weekly newsletters powered by Flodesk, these are the essentials that help me simplify & scale. You’ll also hear about my favorite podcast tools, a few can’t-miss integrations, & why fewer tools that work together beat juggling twenty tabs any day.Resources & Links:Get 50% off your first year with 17hats and Flodesk using these links or code FAIRYTALE.Podcasters & Content Creators: check out Descript and BuzzsproutAdditional platforms mentioned: Google Workspace, Zapier and Canva Grab my Tech Stack PDF hereCheck out all my other freebies mentioned at kristenlettini.com ICYMI Episode 132: Email Marketing Made Simple*** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showVlada Bortnik, co-founder & CEO of Marco Polo, the video messaging app, shares what it really means to build technology that helps people feel close, not just connected.Vlada’s journey—from growing up in Ukraine to working at Microsoft to creating one of the most intentional, human-centered apps in tech—reminds us that business can be both purposeful and profitable. She shares how she and her husband built Marco Polo while raising two young kids, how they’ve kept their company values at the center of every decision, and what it looks like to “work joyfully” for the long game.If you’ve ever felt like technology is pulling you away from what matters most, this conversation is a beautiful reminder that it doesn’t have to be that way.Connect with Vlada on LinkedIn and download the Marco Polo app at marcopolo.me. (BTW if you join Marco Polo and want to try the paid version, use my affiliate link to try 2 months free!)*** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showUse October Theory to end 2025 strong & step into 2026 ready!October is the “Second New Year” — the perfect time to reflect, reset, and realign before the year ends. In this solo episode, I share 4 simple steps to make October Theory work for your business: review your 2025 goals, refresh your systems, refine your content calendar, and protect your energy.✨ Links & resources mentioned in this episode:Grab your free step-by-step Asana content calendar guideListen to my full episode on content calendarsBook a free 30-min consult to chat about your backend systemsStay tuned for Black Friday deals on my fav tools like 17hats + Flodesk — join my email list so you don’t miss them*** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showEmail marketing is the most powerful tool in your business toolkit as a solopreneur—but most people overcomplicate it. In this solo episode, I’ll show you why email matters, how to start your list, and how to stay consistent so your subscribers look forward to hearing from you. 🫶 We’ll cover:Why email beats social media (40× more effective!)How to build your list—even if it’s just your two best friends to startThe role of consistency in building brand trust + better deliverabilityMy favorite tools for email marketing and content planning✨ Plus learn how to use the free version of Asana to create a Content Calendar and plan your email content with ease!+ICYMI: Episode #117 Why You NEED A Content Calendar 🗓️ & How to Make One - FREE!✨Snag 50% off your first year of Flodesk with code FAIRYTALE*** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showSpoiler alert: I learned a lot being part of my very first collaboration— not just about launching, but about how even the best laid plans can change AND how important the client POV is. In this solo episode, I’m pulling back the curtain on what it was like to contribute to a recent collaboration bundle that I was genuinely excited about! I’ll walk you through what went well, what threw me off, and the biggest lessons I took away after opting into my fellow contributors’ offers.Whether you’re planning your next launch, offering a freebie, or hosting a collab of your own, these lessons and reflections are intended to help you keep your user experience as seamless as possible.*** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showJosh Hall shares his inspiring journey from building a successful web design agency to becoming a sought-after business coach for creative entrepreneurs.Today, Josh is a web design business coach, podcast host, and course creator who helps creatives build businesses that give them freedom and flexibility.We dive into how showing up as your authentic self is the key to standing out in a crowded industry – you are your brand’s biggest differentiator. Josh's story is a great reminder that you have permission to evolve, pivot, and design your business around what matters most to you.Tune in to hear Josh’s tips on differentiating your brand, adopting a business-savvy approach, and creating a thriving business that truly supports the life you want to live.Learn more and connect with Josh at joshhall.co or webdesignerpro.com. *** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showGet ready for a little lesson in confidence 101 - with some sandy vibes!Janel Hawkins shares her journey from courageously quitting her job to moving back home to Alabama to pursue her passion for building sandcastles.Janel attributes her "false confidence" and "secondary confidence" to allowing her to keep moving forward, despite some skepticism and negativity around building a business in the sand; she was determined to figure things out, no matter what!Today, as the owner of Sandcastle University, Janel is redefining the art of sand sculpting. Her awe-inspiring creations grace the shores of Alabama, bringing joy to all who encounter them before they vanish with the tide. She also shares her knowledge and passion with people of all ages and skill levels through her classes. In this conversation, Janel discusses the challenges she faced, her strategic approach to overcoming obstacles, and how she expanded her business into teaching sandcastle building classes and creating custom sculptures for events. She also offers valuable advice to aspiring entrepreneurs and insights into her business model, including navigating seasonality and leveraging social media for growth.Tune in to discover Janel's resilience, creativity, and unwavering commitment to her craft and her team.Learn more about Janel and Sand Castle University at sandcastleu.com or follow her on social: Tik Tok | YouTube | Instagram *** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫

Text Kristen your thoughts or feedback about the showWhen the life you've built no longer feels like yours — what comes next?This week, I’m joined by Jenn Arthurton, founder of Old Chicks Know Sht* and host of the podcast by the same name, for a conversation all about identity, reinvention, and redefining success in midlife.After a career shakeup in her 50s, Jenn found herself at a crossroads — one that required deep unlearning, quiet listening, and a whole lot of courage. What came next was a brand, community, and mission designed to empower women who feel like they’re just getting started.Jenn’s wisdom is an inspiring reminder that it’s never too late to create a life that feels like you again.Whether you're navigating a season of change, feeling disconnected from your purpose, or simply craving more meaning in your work… this conversation will meet you where you are.Learn more and connect with Jenn at oldchicksknowshit.com and on Instagram.*** If you’re a 17hats user, I’ve got a quick way to help you stress less. Take my free, 2-minute “How Many Hats?” Quiz to see how you’re using 17hats today — and get a few simple tips to make it even more powerful. ✨ It’s like a mini clarity check for your business — short, simple, and surprisingly therapeutic. 💚 Take the Quiz → kristenlettini.com/howmanyhats Because you deserve a business that feels a little more fairytale 💫