The Bold Biz Podcast

27. The 7 Fears Every Midlife Woman Has Before Starting a Side Business (And What to Do About Each One)

Send us Fan Mail [https://www.buzzsprout.com/2551025/fan_mail/new] Are you too scared to start? Here are the 7 fears holding midlife women back from building a side business If you have been thinking about starting a side business but something keeps talking you out of it, this episode is for you. Jenny gets honest about the 7 most common fears women over 40 have before they take the leap — and what to actually do about each one. She has felt every single one herself, and after 4 years of trial, error, and finally finding her footing, she is sharing what helped. 👉 Grab the free Done Starting Over guide HERE [https://www.theboldbiz.com/doneoptin] The 7 Fears — Let's Name Them Because once you can name the fear, you can do something about it. Fear 1: Am I too late? You are not. The average female entrepreneur starts her first business at 42. The average first-time female millionaire is 49. Martha Stewart. Vera Wang. Mel Robbins. All of them built something big later than you might think. Your experience is not a handicap — it is your edge. Fear 2: I don't know what to sell Too many ideas, or no ideas at all — both feel paralyzing. Jenny shares how to use the Four-Filter Framework (Skills, Time, Energy, Momentum) to cut through the noise and find the one idea that actually fits your life right now. The full framework is inside the Second Chapter Starter Kit, linked below. Fear 3: I don't have time and I'm already exhausted Some gentle tough love here. You probably have more pockets of time than you think — you are just spending them differently. Jenny breaks down how she started in the tiny gaps, and why starting embarrassingly small is actually the whole strategy. Fear 4: I'm not techie enough Tech overwhelm is real, and Jenny gets it. But in 2026, not using AI in your side business means working five times harder than you need to. She shares one simple AI trick you can try today, right from your phone, even if you have never used it before. Fear 5: Who am I to do this? Imposter syndrome hits harder in midlife because we are not used to being beginners anymore. The reframe that actually works — you do not need to be the world's leading expert. You just need to be one step ahead of the person you are helping. Fear 6: What if I lose money? You do not need to spend thousands to start. Jenny breaks down how to get going for under $100 a month — and often for free — and when it actually makes sense to invest more. Fear 7: I don't want to be cringy on social media Jenny's biggest blocker for years. She shares exactly what finally helped her get comfortable being visible — including the 30-day challenge she did just for herself, with bad lighting and zero expectations. Start here 👉 Done Starting Over [https://www.theboldbiz.com/doneoptin] – free guide to break the fear cycle and take your first real step. 👉 The Second Chapter Starter Kit [https://www.theboldbiz.com/kit] – the Four-Filter Framework workbook, $27:  👉 The Bold Biz Collective [https://www.theboldbiz.com/kit] – free Skool community for second chapter women building something of their own:  Keep listening If this episode resonated, you will love these too: 👉 Episode 26: Why You Keep Abandoning Your Ideas (And How to Actually Finish Something): https://www.buzzsprout.com/2551025/episodes/19191244 👉 Episode 18: You Don't Need to Be an Expert – You Just Need to Be Two Steps Ahead: https://www.buzzsprout.com/2551025/episodes/18600721 Ready to stop letting fear run the show? Every single fear in this episode has a workaround. You do not have to feel ready. You just have to start. Stay bold ladies! ✨ /Jenny x Support the show [https://www.buzzsprout.com/2551025/support]

26. Why You Keep Abandoning Your Ideas (And How to Actually Finish Something)

Send us Fan Mail [https://www.buzzsprout.com/2551025/fan_mail/new] Do you have a graveyard of half-built businesses, abandoned Etsy shops, and courses you never finished? You are not alone, and more importantly, you are not broken. In this episode, Jenny gets really honest about her own side business journey – from a $3,000 course she never completed, to Entrepreneurial Gals (a beautiful website with absolutely nothing to sell), to an Etsy jewelry shop, a Shopify store, a print-on-demand yarn accessories brand launched four days before Christmas, and everything in between. And then she breaks down the pattern underneath all of it – the loop that keeps so many second chapter women stuck in permanent restart mode. This one is raw, funny, and very real. Because the problem was never the ideas. It was never giving one of them enough time. In this episode you will learn: * The five-step loop that keeps you abandoning ideas before they have a chance to work * Why hitting resistance feels like the wrong idea – and why it almost never is * What finally broke the cycle for Jenny (and what grew her account from 47 to 10,000 followers in four months) * A simple 90-day framework to finally finish the thing you keep starting If you are tired of the restart cycle, grab the free guide Done Starting Over in the show notes below. It will help you break the pattern and commit to the one idea that is actually worth your time. ⭐ LINKS & RESOURCES: • Download Free Guide, Done Starting Over https://www.theboldbiz.com/doneoptin [https://www.theboldbiz.com/doneoptin] • Join the FREE Bold Biz Collective (Skool Community) https://www.skool.com/the-bold-biz-collective-5477/about [https://www.skool.com/the-bold-biz-collective-5477/about] • Download Free Guide, The Idea Filter https://www.theboldbiz.com/idea [https://www.theboldbiz.com/idea] • Visit The Bold Biz Website https://home.theboldbiz.com/ [https://home.theboldbiz.com/] Support the show [https://www.buzzsprout.com/2551025/support] Support the show [https://www.buzzsprout.com/2551025/support]

25. The Side Business Timeline No One Talks About

Send us Fan Mail [https://www.buzzsprout.com/2551025/fan_mail/new] Have you ever looked at your business and thought… what is the point? Like you’ve been showing up, trying, creating, learning, and still not seeing enough movement to prove it’s working? In this episode of The Bold Biz Podcast, Jenny talks honestly about the part of building a side business that almost nobody shares online, the valley. The slow season. The invisible progress. The weeks and months where it feels like everyone else is moving faster than you. This is not a “just keep going!” motivational speech.  It’s a grounded, honest conversation about what the timeline of building something meaningful actually looks like, especially for women building in the margins of busy lives. 💡 In this episode, we talk about: • Why side business growth is almost never linear • The “plateau of latent potential” and why progress feels invisible at first • What the valley actually feels like emotionally • Why women over 40 often experience the slow season more intensely • The different seasons of building a business, planting, growing, and harvesting • Why celebrating small wins matters more than you think • How to know whether to keep going or pivot If you’ve been feeling discouraged, impatient, or quietly questioning whether you’re cut out for this, this episode will help you see your journey in a completely different light. Because slow does not mean stopped. And the valley is not forever. ⭐ LINKS & RESOURCES: • Download Free Guide, The Idea Filter https://www.theboldbiz.com/idea [https://www.theboldbiz.com/idea] • Download Free Guide, Done Starting Over https://www.theboldbiz.com/doneoptin [https://www.theboldbiz.com/doneoptin] • Visit The Bold Biz Website https://home.theboldbiz.com/ [https://home.theboldbiz.com/] • Join the FREE Bold Biz Collective (Skool Community) https://www.skool.com/the-bold-biz-collective-5477/about [https://www.skool.com/the-bold-biz-collective-5477/about] Support the show [https://www.buzzsprout.com/2551025/support]

24. Why Women Over 40 Cannot Afford to Ignore AI

Send us Fan Mail [https://www.buzzsprout.com/2551025/fan_mail/new] Do you feel curious about AI… but also a little intimidated, behind, or convinced it’s “for younger people” or more tech-savvy entrepreneurs? In this episode of The Bold Biz Podcast, Jenny explains why women over 40 cannot afford to ignore AI, especially if you want to build a side business with limited time, limited energy, and no desire to do everything the hard way. This is not a tech-heavy episode. It’s a mindset and opportunity episode. Jenny shares her own journey from feeling unsure and hesitant about AI to now using it daily as a business partner to save time, create content, plan strategy, and remove the overwhelm that keeps so many women stuck. She also shares a recent real-life example of using AI to create 30 days of Instagram content in a fraction of the time it would normally take.  💡 In this episode, we talk about: • Why hesitation around new technology may be costing you time and momentum • How AI can reduce imposter syndrome and build confidence • The shift from using AI like a search engine to using it like a business partner • How Jenny used AI to plan 30 days of content in minutes • Why AI is a huge advantage for women building something on the side • How to start using AI today, even if you’re a total beginner • Why this moment in history is a real opportunity, not hype If you’ve been telling yourself you’re not tech-savvy enough, too late, or too behind to benefit from AI, this episode may completely change how you see what’s possible. ⭐ LINKS & RESOURCES: • The Bold (AI) Shortcut FREE Webinar: (May 3rd, 7 pm GMT+1) https://www.theboldbiz.com/shortcut [https://www.theboldbiz.com/shortcut] • Download Free Guide, The Idea Filter https://www.theboldbiz.com/idea [https://www.theboldbiz.com/idea] • Download Free Guide, Done Starting Over https://www.theboldbiz.com/doneoptin [https://www.theboldbiz.com/doneoptin] • Visit The Bold Biz Website https://www.theboldbiz.com/ [https://www.theboldbiz.com/] • Join the FREE Bold Biz Collective (Skool Community) https://www.skool.com/the-bold-biz-collective-5477/about [https://www.skool.com/the-bold-biz-collective-5477/about] Support the show [https://www.buzzsprout.com/2551025/support]

23. You're Not Behind. You're Right On Time

Send us Fan Mail [https://www.buzzsprout.com/2551025/fan_mail/new] Do you ever feel like you’ve missed your moment… like everyone else is already ahead, already building, already figuring it out? In this episode of The Bold Biz Podcast, Jenny dives deep into one of the most persistent and quietly limiting beliefs that keeps women stuck, the feeling of being too late, too behind, or too far removed from where they “should” be. This is not just a mindset episode. This is perspective, data, and a little bit of tough love. Jenny shares why this belief is not only untrue, but why midlife might actually be your biggest advantage when it comes to building something meaningful and profitable. From real-world data about women entrepreneurs to deeply personal reflections on starting before feeling ready, this episode will challenge the story you may have been telling yourself for years. 💡 In this episode, we talk about: • Why the feeling of being “too late” is so common, and why it’s misleading • The data showing women 40+ are the fastest growing entrepreneurial group • Why your life experience is your biggest advantage, not your limitation • The discomfort of being a beginner again, and why that’s part of the process • The difference between motion and real action, and why it matters • Why confidence only comes after you start, not before • How small, imperfect steps today can completely change your future This episode is both a wake-up call and an invitation. Because the truth is, you are not behind. You are standing at the exact moment where everything can begin. 💖 ⭐ LINKS & RESOURCES: • The Bold (AI) Shortcut FREE Webinar: (May 3rd, 7 pm GMT+1) https://www.theboldbiz.com/shortcut [https://www.theboldbiz.com/shortcut] • Download Free Guide, The Idea Filter https://www.theboldbiz.com/idea [https://www.theboldbiz.com/idea] • Download Free Guide, Done Starting Over https://www.theboldbiz.com/doneoptin [https://www.theboldbiz.com/doneoptin] My favorite all-round, beginner-friendly marketing tool: Systeme.io [https://systeme.io/?sa=sa0127489850ec8f668b5abdc09781294ba2cb5466] (affiliate link [https://systeme.io/?sa=sa0127489850ec8f668b5abdc09781294ba2cb5466]) • Visit The Bold Biz Website https://www.theboldbiz.com/ [https://www.theboldbiz.com/] • Join the FREE Bold Biz Collective (Skool Community) https://www.skool.com/the-bold-biz-collective-5477/about [https://www.skool.com/the-bold-biz-collective-5477/about] Support the show [https://www.buzzsprout.com/2551025/support]