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

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

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 – free guide to break the fear cycle and take your first real step.

👉 The Second Chapter Starter Kit – the Four-Filter Framework workbook, $27: 

👉 The Bold Biz Collective – 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

Transcript

Main Into

SPEAKER_00 0:00

Can I ask you something? How many times have you thought about starting a side business and then quietly tucked yourself out of it before you even opened a single tab or wrote down a single idea? Because I did that for years, and I had a really convincing list of reasons why now wasn't the right time. Why I wasn't ready, why someone else was probably already doing it better. And it turns out most of those reasons had a name. And once I knew the name, I could actually do something about it. Welcome to the Bold Biz Podcast. I'm Jenny Lavalius, and this podcast is for women over 40 who are ready to build something of their own without the hustle, the burnout, or the pressure to be perfect. If you've ever thought it's too late for me, or that everyone else seems to have it all figured out, you're going to feel right at home here. Let's dive in. Okay,

Episode Intro

SPEAKER_00 0:57

ladies, today's episode is one I've been thinking about for a long time. And I genuinely believe it might be one of the most important ones I record for this podcast. Because here's what I know from my own almost four years of doing this, stumbling through it and finally finding my footing. The practical stuff is rarely what stops us. It's the stuff going on in our heads that stops us. So today I want to name it, all of it, honestly and openly, because I've personally felt every single one of these fears at some point in my own journey. And this isn't me talking at you from some elevated place where I've got it all figured out. This is me sitting right next to you saying, I know exactly how this feels, and here's what helped me. I've collected the seven biggest fears that women in midlife voice when they're thinking about starting a side business. And we're going to go through every single one of them today. So let's get

Fear 1: Am I Too Late?

SPEAKER_00 1:59

into it. The first fear, and probably the most common one I hear, is this. Am I too late? And I want to start here because I think it's the fear that quietly sits underneath all the other fears. Even when women don't say it out loud, it's often there in the background, just whispering away. Here's why I think this fear is so specific to midlife women. Most of us in our 40s and 50s have spent the last two decades in a kind of steady rhythm. We built our careers, we raised our families, we figured out how to manage a household and a relationship, and aging parents, and everything else life threw at us. And somewhere along the way, we quietly stopped starting new things. We became competent, we became the person who knew what she was doing. And starting a business from scratch means becoming a beginner again. And honestly, that's uncomfortable when you're not used to it anymore. But here's the thing, and I really want you to hold on to this. The world has shifted. The job market has shifted, with AI coming into the workforce in full force right now, job stability doesn't feel like what it felt like even a few years ago. And the general sense of shaky ground that a lot of us are feeling is making so many women think, what does my future actually look like? And if I want some kind of security that I've built myself on my own terms, can I still do that? The answer is yes. And not a polite yes, but a data-backed yes. Here are some numbers I want you to hold on to. The average woman pivots careers at 39. The average female entrepreneur is 42 when she starts her first business. And the average first-time female millionaire is 49. 49, ladies. And then you've got women like Martha Stewart, who built an empire in her 40s and 50s, and Vera Wang, who didn't design her first wedding dress until she was 40. And Mel Robbins, who was broke and in debt in her late 30s before she became one of the most well-known voices in personal development in the world. You are not late, you're right on time, and honestly, you've got something that a 23-year-old entrepreneur simply doesn't have. And that's decades of life experience, hard-won skills, and the kind of perspective that only comes from having actually lived. That's not a disadvantage. That is your edge.

Fear 2: I Don't Know What to Sell

SPEAKER_00 4:41

The second fear is what I call the direction paralysis question. And it shows up in a few different ways. I don't know what to sell. I've got too many ideas. I've got no ideas. How do I even pick something that actually makes money? I've got skills, but I don't know how to turn them into a business. And I felt all of these myself as well. I'm a graphic designer by trade, but in the beginning, I didn't want to freelance and just trade hours for dollars, because that felt like creating another job for myself. And with the family commitments I had, there just wasn't enough room to cap my income at however many extra hours I had per week. So I needed to build something I could scale, something that could make money even when I wasn't working. And for me, the answer was digital products. Because you can honestly start small. We're talking a simple PDF guide, a one-hour tutorial, a Canva template, a tiny specific little thing that solves one problem for one person. And you can package it, price it, and sell it without spending a fortune to get started. And here's what I got wrong in the beginning. Because I thought I needed to go big right away. I kept thinking if I create a big course, I'll make more money faster. But actually, starting small is so much smarter because a low-ticket product is easier to sell, the threshold to buyer is lower, and more importantly, it gives you the chance to practice the skill of selling, to build your confidence, and to learn how to talk about what you offer in a way that feels natural and aligned with who you are. And then once you've figured that out, you can build upward from there. As for figuring out what to sell in the first place, here's what I suggest. Grab a big piece of paper and just write down everything you could teach, share, package, or turn into a guide. And I really do mean everything. How to get your kids to sleep, how to find a great golf swing, the best carbonado recipe in the world, interior decorating, pet care, navigating a difficult conversation with a teenager. There's a market for all of it. And then once you've got your list, you can run it through my four-filter framework to figure out which idea is the best fit for your actual life right now. The four filters are skills, time, energy, and momentum. And the full framework is inside the second chapter starter kit, which you'll find linked in the show

Fear 3: I Don't Have Time and I'm Already Exhausted

SPEAKER_00 7:22

notes. Fear number three is one I hear constantly, and it's completely valid. So I'm not going to pretend otherwise. Midlife women are often carrying so much full-time jobs, kids, aging parents, partners, the house, the mental load of it all. And I know that because I live it too. But here's some gentle tough love. Because most of us have more pockets of time than we think we do. We're just spending them in ways we don't always notice. Think about the time you spend on Netflix in a week. The time you spend scrolling on social media. And even if you've just reclaimed one of those and even if you just reclaimed one of those hours, just one, and put it towards building something of your own, that would be enough to start. And in today's world, you can genuinely work from your phone in the gaps, on the bus, in the car while your partner's driving, sitting in the pickup line at school, even and I say this without judgment, on the bathroom break that has become your only five minutes of peace in the whole day. The key is to start so small that it genuinely doesn't feel overwhelming. So don't think about building a business. Just think about doing one small thing today. Write one email, record one short video, draft one post, create the outline for your new product, that's it. Just one small thing. That's honestly how I should have started. Tiny and inconsistently at first, but over time, those tiny moments compound into something real. And once you start seeing what's possible in just a few hours a week, you'll naturally want to protect that time and make more of it available.

Fear 4: I'm Not Techie Enough

SPEAKER_00 9:11

Fear number four is the tech panic. And it goes something like this. I'm not techie enough. I don't understand all the tools. AI scares me. All of it feels completely overwhelming, and I don't even know where to begin. And I completely understand this one. And I want to say very clearly that your fear of tech is valid and normal, and it absolutely doesn't mean you can't do this. Here's what I want you to hear. You start small with tech too. You don't need to learn 20 platforms at once. You don't need to understand funnels and automations and email sequences on day one. You just start with one tool, one platform, one task, and you get comfortable there before you add anything else. And here's the thing about AI specifically, because I know it feels like a lot right now. But in 2026, if you're not using AI in your side business, it's going to be a much harder road. And that's not me trying to scare you. It's just the reality of the landscape we're operating in. You've probably got a very limited time every week, and AI isn't about replacing you, it's about getting things done in a fraction of the time. Let me give you one tiny example that you can actually try today. If you want to send a newsletter to your audience, don't sit down and stare at a blank page for an hour. Just grab your phone, record a one-minute voice note of what you want to say, upload the transcript to Claude or ChatGPT, or whichever platform you prefer, and ask it to turn that into a polished email with a subject line, a call to action, and you're done in minutes. That's the kind of time saving that genuinely changes everything when you're building something on this side.

Fear 5: Who Am I to Do This?

SPEAKER_00 11:02

Fear number five is the big one for so many women, and it sounds like this. Who am I to do this? I don't know enough. I barely know how to do this myself. Why would anyone buy from me? There are so many people already doing exactly what I want to do, and they're so far ahead of me. So why would anyone choose me over them? And I've asked myself every single one of these questions at some point. Every one of them. But here's what I've come to understand about imposter syndrome specifically in midlife. We're at a point in our lives where we've been competent for a long time. We've been the person who knows what she's doing in most areas of life. And starting something new where we genuinely don't have all the answers yet, can feel really destabilizing because we're just not used to feeling like a beginner anymore. But here's the reframe that actually helped me. You don't need to be the world's leading expert, you just need to be one step ahead of the person you're trying to help. Marie Forlio, who built a multimillion dollar business helping women do exactly this kind of thing, has a phrase I love and come back to all the time. She says everything is figure outable. And the truth is, if you've figured something out that someone else hasn't, you've got something to offer. It's honestly that simple. You're not selling perfection, you're sharing a path. And your lived experience, the messy middle, the things you learned the hard way, that's often more valuable to your audience than polished expertise. Because it's real, it's relatable, and it gives people hope that they can do it too. So the next time imposter syndrome taps you on the shoulder and asks, Who are you to do this? I want you to answer back. I'm someone who figured something out that someone else is still struggling with, and I'm going to share it. Fear

Fear 6: What If I Lose Money?

SPEAKER_00 13:04

number six is the financial fear, and it's a real one, especially for women who've watched their savings get eaten up by courses and memberships and tools that didn't deliver on their promises. And I spent a lot of money in the early days of my journey chasing shortcuts, so I really want to save you from that if I can. So here's the truth. You don't need to spend thousands of dollars to start. And most of the software I use has a free plan. So you can genuinely get started for well under $100 a month for all the tools you need. In many cases, for free. YouTube is free, the Bulbus Collective is free, and the information you need to get started is absolutely available to you right now without spending a single cent. And my advice when it comes to investing money in your business is this don't buy a course or a coach or a mastermind until you've done everything you possibly can for free, and you've got actual traction, some real evidence that your idea is working. Then, when you're ready to level up and you've got the money to invest, you'll be in a much better position to use that investment well. Because you'll actually understand what you need. Start free, start small, and let the business pay for its own growth.

Fear 7: I Don't Want to Be Cringy on Social Media

SPEAKER_00 14:25

And fear number seven. Oh, this one, this was honestly my biggest blocker of all. Because I just did not want to be cringy on social media. I didn't want to fill myself, I didn't want to watch myself back. It just made me want to disappear. I was terrified of what people would say. And I don't want to become one of those people doing trendy dances in front of their kitchen and calling it content. Ladies, I felt all of this deeply and for a long time. For years I tried to build a business where I didn't have to show up. The faceless Instagram accounts, the Amazon KDP coloring books, the print-on-demand shops. I even spent weeks creating an AI avatar of myself, thinking that would solve the problem. And honestly, some of those approaches can work for certain types of businesses. But here's where I eventually landed for myself. I'm building a personal brand. I want to help women start businesses. And if I'm not willing to show up and be real and be seen, how am I going to convince anyone else that they can do that? So I had to figure out how to get comfortable being visible. And here's what actually worked for me. I started with my voice first, because I launched this podcast in November, and I could record it in sweatpants with no makeup on any day of the week and nobody would see my face. And that was such a relief. It gave me a way to show up consistently without the visual pressure. And then last year I did a 30-day YouTube shorts challenge for myself. Just for myself. One short per day, bad lighting, no script, no editing, just me talking for 30 to 60 seconds about something related to what I was building. And I want to be clear that I didn't care if anyone watched it. The whole point was just to get used to being in front of the camera, to stop flinching when I saw my own face on the screen. To stop obsessing over every filler word and awkward pause. And it worked, because visibility is honestly a muscle. And the only way to build it is to use it. Even imperfectly, even privately, even when you think nobody's watching. Now I script my content because that works for me right now. I use a teleprompter app and it means I can stay confident and clear without losing my train of thought mid-sentence. And there's absolutely no shame in that. You use the tools that help you show up. But if your dream is to build a personal brand and connect with real people, you're going to have to step into visibility at some point. And the good news is you don't have to feel ready. You just have to start. Okay, ladies, seven fears, all of them valid, all of them real, and all of them workable. I want you to do something after you finish listening to this episode. Grab a piece of paper and write down which of these seven fears

Episode Outro

SPEAKER_00 17:30

is the loudest one for you right now. Just one. The one that's sitting in your chest the most heavily. And then I want you to remember that you're not the first woman to feel it. I felt it, and every woman who's ever built something has felt it. And the ones who built something didn't do it because the fear went away, they did it while the fear was still there. If you're sitting with a few of these fears right now and you're wondering where to even begin, I've got a free guide that walks you through exactly how to break this cycle of overthinking and take your first real step. It's called Done Starting Over, and you can grab it in the show notes below the episode. And if you want to be part of a community of women who are doing exactly what you're trying to do, come join us in the Bolt Biz Collective. It's free, it's warm, it's full of second chapter women building something of their own without the hustle or the perfection pressure. And the link for that is in the show notes

Main Outro

SPEAKER_00 18:30

as well. Thank you so much for spending this time with me today. And if this episode resonated, I'd love for you to follow the show, share it with a friend who might need it, or leave a review. Because it really does help more women find the show. And if you want to keep the conversation going, come find me inside the Bowl Base Collective. The link is in the show notes. Until next time, stay bold, ladies!