69. Break the "Someday" Cycle: It’s Time to Start Your Business

September has this fresh start energy that reminds me of January - the kids are back in school, you finally have a moment to breathe, and suddenly, those goals you set months ago start bubbling back up. 

That quiet moment after drop-off, that first hot cup of coffee in months - these are the moments when that little voice whispers about the business idea you've been carrying around. But then the practical voice jumps in with all the reasons why you can't: no time, no idea where to start, not qualified enough.

Tune in this week to hear why so many moms get caught up in the “someday” cycle, and what it takes to start building something that's truly yours before the year ends. And if you want to learn the 4 simple steps that every successful mom entrepreneur has followed to start their business, make sure to come to my free webinar and I promise, you'll walk away with clarity that you didn't have before.


If you’re ready to stop waiting and start building your business right now, you need to join my *FREE* webinar, Start a Business Before Winter Break. It’s happening on September 19th, 2025, at 1pm ET/10am PT. Click here to register. 


What You’ll Learn from this Episode:

  • Why September's back-to-school season creates the perfect window to start your business.

  • The difference between having time and making time for what matters to you.

  • Why confidence comes from taking action, not from feeling ready or having all the answers.

  • What the "someday cycle" is and how to break free from waiting for the perfect time.

  • How working on your own business can actually give you more energy for your family (not less).

Listen to the Full Episode:

Featured on the Show:

Full Episode Transcript:

The three biggest obstacles I hear from moms are: I don't have time, I don't know what to do, and I don't know where to start. But here's what I've learned. It's not about having time. It's about making time for what matters to you. None of us have time to start a business, but somehow we make time to rush our kids to the doctor when they're sick or make it to those evening recitals for them. We make time, we create time for that because it's what matters.

Welcome to How to Quit Your Job, the podcast for moms ready to ditch the nine-to-five and build a life and business they love. I’m your host, Jenna Rykiel. Let’s go.

Hi mom friends. You know what I love about September? Besides the leaves changing and the cool air, it has this fresh start energy similar to January. The kids are back in school, you finally have a moment to breathe, and suddenly those goals that you set back in January, they start bubbling back up to the surface. And if you're a mom who's been thinking about starting a business, maybe for months, maybe for years, and you keep getting stuck in the same cycle of, "I don't have time. I don't know where to start. I don't know what to do. I'm not qualified," then I am so glad you found this episode because it's going to change everything.

Because today, I want to talk about why this season, the end of summer and shifting into fall, is actually the perfect time to stop waiting and start building something that's truly yours. Here's what I know is happening for so many of you right now. If you're catching this live or within the first few weeks of it going live, then your kids just went back to school. And for the first time in probably months, you had a quiet moment. Maybe you were drinking coffee while it was still hot or sitting in your car after drop off. And with that quiet moment, you might have heard that little voice in your head, the one that says, "Remember that business idea you had? Remember how excited you felt about the possibility of doing something just for you?"

But then, almost immediately, and this happens for all of us, that other voice jumps in, the practical one. The one that says, "Who are you kidding? You don't have time for this. You don't even know where to start. You can't take away time from your family. You've moved up the corporate ladder. You're not an entrepreneur." And I want you to know you're not alone. I hear this exact conversation from moms every single day. And I want you to know that voice, the practical one that's usually driven by fear, it's not telling you the truth.

Okay, here's what's really true. You are exactly where you need to be. And September is actually the perfect time to get started. Back when I was working my corporate job, I used to come home every single day like a ticking time bomb. I was so drained, so resentful, so completely empty from pouring everything into work that didn't fulfill me, that I had nothing left for my husband when I got home.

And this was pre-kids for me. So I can only imagine how much exponentially worse this would have been if it were just a few years later when my house was loud and chaotic and when there's so many more little people and beings that need things for me. So I'd come home drained and my husband would be the target of my misery and resentment. So we actually created what we thought was this creative solution to that problem.

Every day after work, we'd take these walks around the park, City Park, if you're familiar with Denver. But here's the thing: he wasn't allowed to speak to me until I spoke first. When I finally said something, anything, that was his cue that I was human again and it was safe to interact with me. For years, this was our normal. It was years of me being the worst version of myself the moment I walked through the door. I thought this was just how life worked when you had a demanding and stressful job. I thought being completely drained was the price of being successful, was the price of having a six-figure job.

But then something happened that changed everything. I hit a breaking point. I hired a coach and finally started that business I had been thinking about for six years. I didn't know the first thing about where to start or how to get clients. So what I did was I decided to start volunteering free coaching services at a local single parent housing coalition. Of course, unfortunately, single parents are usually moms. And so I worked with a ton of moms at an organization where I lived for free. I'd work my corporate job from 8:00 AM to 6:00, and then from 6:00 to 7:00, I'd coach moms for free.

And you would think that working an extra hour each day would make me an even bigger monster when I got home. But the exact opposite happened. On the days I had coaching calls, I came home with more energy than the days without them. I came home ready to talk to my husband about my day. I came home wanting to share about and ask about his day. And it's so interesting because how could working more hours make me less angry and more present with my family?

It was because I was finally doing work that aligned with who I really was, work that made me feel alive instead of drained. I was still doing the work that made me feel drained, but now I had this piece of my identity, this piece of myself that made me feel alive, this project that I was working on, this impact that I was making, and it changed everything. And here's what I see happening with so many brilliant, capable moms: they're stuck in what I call the "someday cycle." And I was in this cycle as well, right? We keep thinking that we'll start a business when the kids are older, when work calms down, when we have more time, when we feel more confident.

I did that for six years and I didn't even have kids, but somehow my brain found even more excuses. So pile on kids and other responsibilities and recitals and vacations, and of course, our brain wants to push these things off till someday. But what I want to be honest about is that someday never actually comes unless we're intentional. Because there will always be something. There will always be a reason to wait. And meanwhile, you're pouring all of your energy into someone else's dreams: your employer's vision, your family's needs. Everyone gets the best of you, except for you.

The three biggest obstacles I hear from moms are: I don't have time, I don't know what to do, and I don't know where to start. But here's what I've learned. It's not about having time. It's about making time for what matters to you. I just did an episode on this, episode 61, How to Create Time When You Have None. None of us have time to start a business, but somehow we make time to rush our kids to the doctor when they're sick or make it to those evening recitals for them. We make time, we create time for that because it's what matters.

So it's so important about making time and deciding that this business and these goals matter. And right now with kids back in school, you actually do have pockets of time that you didn't have all summer when you were on vacation and watching the kids and trying to puzzle together all of those summer months. I know how that goes. You have to decide that your goals are a priority.

When moms say, "I don't know what to do," this one breaks my heart because every mom I've ever worked with is beyond brilliant. I know that if you're listening to this, you are beyond brilliant as well. You have skills, experiences, and perspectives that the world needs. But it's so hard to see your own value when you're in the thick of it. I know that deep down there's a part of you that not only knows what you enjoy doing and what you're good at, but there's also maybe a part of you that, if you knew you couldn't fail, has a business idea brewing.

And if you're thinking, "I don't even know where to start" or "I'm not an entrepreneur," of course you don't. You've never done this before. But I want to let you in on a little secret: none of us feel confident when we start something new. Confidence comes from taking action, not from feeling ready. And in this podcast and throughout the time, if you're on my email list, I share so many ways that you can start taking action. You don't have to know what to do first or next. You just have to decide to take action and create forward motion and learn as you go.

And listen, everyone I've ever worked with has built their career working for someone else. That's why I call what I do "helping moms transition out of traditional roles." No one I've ever worked with has the entrepreneur bug. That doesn't mean you can't make the transition. It just means that you'll have to adjust how you're used to working. But us moms, if we know one thing, we know how to adapt.

So what's the answer here? How do you go from stuck in the someday cycle to actually building something that's yours? There are four simple steps, and I mean simple, that every successful mom entrepreneur I know has followed. Not complicated strategies, not fancy tech skills, not some secret formula, which I know we all think that there is this secret formula or answer out there that we just have to find. But these are four accessible steps that work regardless of your background, your experience level, or how much time you think you have.

And I'm going to be sharing those four steps in a free webinar that I'm hosting on September 19th at 1:00 PM Eastern Time, 10:00 AM Pacific. It's called Start a Business Before Winter Break. And this is genuinely about giving you the roadmap to stop waiting and start building. This is too much to share in just one podcast episode, but I promise that these are themes and tools that I've talked about throughout this podcast.

I'm also going to share why most business advice doesn't work for us moms. I've learned that myself and I've learned that with working with so many other moms. We're going to talk about the real obstacles that keep smart, capable women stuck in the dreaming phase and how to know if you're actually ready to take this step and start building a business. Listen, there are only a few months left in the year at the time of this recording and you have the choice to end this year exactly where you started, or you can use this September energy to finally move forward and start that business.

I want you to imagine showing up to the holiday gatherings at the end of the year excited to talk about the business that you've been working on. Just imagine confidently sharing what you've been up to, talking about those exciting new ideas, no longer feeling a pull to talk about feeling burnt out in your traditional role, and instead excited to talk about the energy of your business. This doesn't mean you have to leave your job or a regular paycheck by the end of the year. It just means you're going to have all the puzzle pieces to start building something of your own.

You're going to start laying down the foundations so that you can keep taking action and so that you can evolve this business, because it can't evolve, no idea can evolve without first allowing it to come to life. And what I'm going to talk about in this webinar on September 19th is the four things to focus on to help this thing come to life, even if you have no idea what that idea is right now.

How do you go from stuck in the someday cycle to actually building something that's truly yours? I want to tell you about a few of the moms that I've worked with because their stories will show you exactly what's possible. One of the moms came to me feeling completely stuck. She told me, "Jenna, I don't even know what strengths I have to offer the world." She's a single mom and actually had no plans of leaving her job. She planned to retire there but wanted to make more money so that her and her son could travel and so she'd be able to retire a little bit earlier and still be financially stable.

But here's the thing. Like I said, every mom has incredible value to offer. We worked together using my business idea mapping process, which focuses on interests, experiences, and strengths, even the ones or especially the ones you can't see. And within a few sessions, she settled on a business idea that made her feel alive. And a few months ago, she signed her first major client contract, a $10,000 government contract.

I know she recently started prioritizing travel with her son. We talked a lot about how to step into what she wanted more of in her life, maybe before the business was mature, right? I wanted her to start living her life and not wait around for the results, but to really make those things that were important to her, like travel with her son, happen even before the business was happening. But what I want to say is that it's just fun to think about the type of trip that they can splurge on with that extra income.

So going from "I don't know what I have to offer" to landing a five-figure contract, that's what happens when you stop underestimating yourself. There's another mom who was working in corporate, feeling completely drained, just like I was, just like a lot of you are. She was scared to leave her “stable" job, but she was miserable. Similarly, when we started working together, she had maybe a vague idea of what she wanted to do, something she had been thinking about but never took seriously. And once she started taking herself and the business seriously, we set the foundations of the business and she was able to sign her first big contract before she even left her role.

Not only that, this client was special because she started the program wanting to leave her job as soon as possible. She was burnt out, she was miserable. But shortly after signing up for coaching, she found out that staying an extra few months would mean that equity that she had in the company would vest. So we really worked on things like boundaries and how she was staying in control of her time and honoring her own priorities and truly her mindset around work to make it suck less, which I have an entire episode on that topic. It's episode 4. And she was able to not only stay at her job those additional months to secure that extra money, she actually enjoyed it.

And the kicker here is that the first big client contract that she signed was at that previous company. She wanted to keep working with that company, but now she was getting paid a higher rate per hour. She was able to design and control the projects she worked on. Her work was now flexible, and she didn't have to request PTO when her kids were sick. And she didn't have to deal with all the company emails. A win-win, right? When she put in her two weeks notice, that scary conversation turned into a client. It's amazing what moms can do.

And I want to share what one of my clients told me recently. She said, "Your coaching transformed my mindset and gave me both the skills and support I needed to launch my dreams. But this program hasn't just been about business, it's been about personal growth and empowerment." Entrepreneurship truly is a personal development journey in disguise, just like motherhood, right? We learn so much about ourselves. There's so much personal growth and empowerment in the process.

Every single mom I've worked with has started a business, every single one, whether they came to me with a fully formed idea or absolutely no clue what they wanted to do. Every mom is capable of starting a business. Every mom is capable of bringing their idea to life because there are just 4 simple steps, and I mean simple, that work regardless of your background, your experience level, or how much time you think you have.

And as I mentioned, I'm sharing these four steps in a free webinar that I'm hosting on September 19th. There is a beautiful gap of time right now before more holidays consume us, before winter recitals, before winter break, and especially before, and I want to emphasize, the dreaded sick season that we all know is coming because winter is coming. Now is the time and this webinar is genuinely about giving you the roadmap to stop waiting and start building, because right now is the perfect time.

If you are listening to this and thinking, "Yes, that's exactly how I feel," then I want you to mark your calendar right now, September 19th, 1:00 PM Eastern, 10:00 AM Pacific. One hour of your time could change the entire trajectory of your career and life. You can find all the details in the show notes at Jenna.Coach/69. Or you can go directly to the registration link at Mom.Jenna.Coach/winter. And this webinar is completely free. And I promise you'll walk away with clarity that you didn't have before.

If you're catching this episode after September 19th, please send me a quick email, Jenna@Jenna.Coach, or you can DM me, find me on LinkedIn or Instagram, and I'll make sure you get the recording of the webinar. You don't need to have it all figured out to start. You don't need more credentials, more experience, or more anything. You just need to start taking yourself and your dreams seriously. You need to decide that going for your goals is not going to take away from your family. And in fact, it's going to make you a better version of yourself, which will 100% give to your family in the most amazing ways. And I know that 100% to be true.

Those goals you set back in January, they're still valid. That voice in your head telling you that you're meant for more, that voice is right. And this month, this beautiful fresh start moment when the kids are settled and you finally have space to think, this is your time. I hope to see you on September 19th. Reserve your spot at Mom.Jenna.Coach/winter or pop into the show notes and you'll get the link to register. Come ready to start taking action to create something of your own. And until then, remember that you don't have to wait until someday. Someday can be right now.

Thanks for listening to this week’s episode of How to Quit Your Job: A Mom’s Guide to Creating a Life and Business You Love. If you want to learn more about how I can help you stop making excuses and start making moves, head on over to www.jenna.coach. I’ll see you next week.

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