50. Your First 50: A Roadmap for Mastering Any Business Skill
What if the key to mastering any business skill wasn't perfection, but simply showing up 50 times? In celebration of my 50th podcast episode, I'm sharing a transformative framework that has revolutionized my coaching business and can do the same for yours – the First 50 Challenge.
This milestone got me reflecting on the power of consistency and intentional repetition. Who I was on episode one last June is completely different from who I am today, not just because time passed, but because of the experience, learning, and momentum that came from committing to something 50 times. It's this exact principle that helped me transform from a nervous new podcaster to a confident content creator.
Join me this week to learn how the First 50 Challenge eliminates perfectionism, builds self-trust, and creates tangible results – all while being 100% within your control as a busy mom entrepreneur. Whether you're still in corporate dreaming of your exit, just starting your business, or in growth mode, this framework provides a practical roadmap for exponential improvement through deliberate practice.
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What You’ll Learn from this Episode:
How to identify the perfect skill or task for your First 50 Challenge based on your specific business stage.
Why committing to 50 attempts of anything builds unstoppable momentum and eliminates perfectionism.
The six-step process for committing to and executing your First 50 Challenge with intention.
How to transform mindless repetition into deliberate practice through intentional evaluation after each attempt.
The critical role accountability plays in successfully completing all 50 attempts.
Listen to the Full Episode:
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Full Episode Transcript:
When I first started my coaching business, I took on a challenge that transformed everything. 50 free coaching sessions. The true value wasn't just that 50 people learned what I did as a coach, though that led to referrals and my first paying clients. The real magic happened in the repetition itself. With each session, my emails got clearer, my confidence grew stronger, and my process became more refined.
Today, in celebration of our 50th episode milestone, I'm giving you this same transformative tool: a framework I call Your First 50. By the end of today's episode, you'll have a practical roadmap to master any business skill that feels challenging right now and a process for exponential growth through intentional repetition.
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. So, this is episode 50. Can you believe it? 50 weeks of showing up, sharing strategies, and building this community together. It dawned on me when my husband and I were both working at the kitchen table one Friday when I was putting the content together. And I was going to talk about competition in this episode, but he was like, absolutely not. You have to do something special for the episode. So here we are.
This milestone got me thinking about the power of consistency and repetition in business growth. Who I was on episode one last June is completely different from who I am today. And it's not just about the time passing; it's about the experience, the learning, and the momentum that comes from committing to and doing something 50 times, which is not a small number. It reminds me of Malcolm Gladwell's talking about the 20,000 hours concept to mastering any skill.
That's why today, I want to talk about a powerful concept that can revolutionize how you approach your business. And this is really exciting because this concept isn't something that I've had as a tool in my business. It's something that has evolved in my reflection of this 50-episode milestone. And so I don't even have a cheeky name for it. So we'll just call it the First 50 Challenge.
And no matter where you're at in starting a business, even if you have no intentions of starting a business, this challenge can be applied to almost any skill or task that you want to improve on. So if you're still in corporate, just starting a business, or tackling growth mode in your business, this challenge will be an opportunity to transform how you develop any skill in your business or in life really. And I will give examples of each of those.
So, here's what I want to talk about in this episode. I'm going to introduce the First 50 Challenge and why committing to it builds unstoppable momentum. We'll talk about how to identify the perfect skill or task for you to focus on for the specific business stage you're in. I'll share a practical system for committing and executing with intention, which is really the meat and bones of this episode, and what happens after completing the challenge and how to leverage your new experience.
The beauty of this approach is that it's going to eliminate perfectionism, which is a topic that has been coming up a lot recently with my clients. Similarly, it builds self-trust and creates tangible results, all the while being 100% within your control as a busy mom entrepreneur, which I will talk more about in a few minutes.
But on the topic of perfectionism, since that keeps coming up in my sessions. When we are working on our businesses, especially early on, we get caught up in the perfectionism trap. So we treat each task like it needs to be flawless before we can put it out into the world. This perfectionism isn't just slowing us down; it's absolutely paralyzing us and consuming precious energy that we just don't have as moms, okay?
So, I want to share a behind-the-scenes look at this podcast. Those first podcast episodes took me hours to create. I'm somebody who really likes to do the pre-work, map out what I'm going to say, really put thought into the script, into the points that I'm making, and really workshop it before I go live. And like I said, it took me hours to do that for my first few episodes. I would obsess over every word. I'd re-record sections multiple times and still feel anxiety when I was sending it off to my team and when they were then publishing it and when it was going live.
So fast forward to now, the process is smoother, faster, and honestly way more enjoyable. When I analyze my first 25 episodes versus my most recent 25, the difference is striking, right? The content now is more focused because I've really learned what resonates with you, my listeners. My delivery is more confident. My systems are more efficient, from planning to recording to promotion. I even upgraded my tech along the way, recently adding better lighting and a camera for future video content.
And when I'm promoting my podcast episodes each week, again, that used to take me hours, even with the help of my team. Now, I literally can do it. I just did it right before for the episode prior to this, and it literally took me 10 minutes. So it's amazing how much time we can save and how much less energy we need once we become more proficient in what we're doing.
So what I want you to really understand is that growth didn't happen with this podcast because I waited until I was ready. It happened because I was willing to be imperfect 50 times in a row. When we're on attempt one of anything, our brain spirals with questions. We're asking, will this work? Will I get anything out of it? What will the results be? That mental chatter pulls us out of learning mode and into judgment.
But the magic of committing to 50 attempts is that it completely shifts your mindset. Suddenly, those first few attempts are allowed to be, excuse my English, or French, shitty first drafts, okay? They're supposed to be. Doing anything new is scary, and your brain will absolutely freak out, and that's completely normal. But when you promise yourself 50 tries to improve, you release the pressure on those early attempts. You give yourself permission to be a beginner, which is incredibly freeing for perfectionist moms who are used to being excellent at everything, like myself.
Getting this mental drama out of your head is a complete game-changer. It allows you to experiment and take risks, knowing that improvement is the goal, not perfection. And we'll talk more about exactly how to ensure you're getting better each time in a minute, which is absolutely critical.
But what I also want to offer is that completing all 50 attempts is a goal that's 100% in your control. It doesn't depend on anyone else saying yes, paying you money, or making decisions. It's simply you committing to something that you can repeat 50 times, which builds massive self-trust and momentum. This is the full ownership I talked about in last week's episode, okay?
And yes, 50 is a big number. I've been told by my podcast team that I'm now part of an elite tier of podcasters, okay? Only 49% make it to episode 8, and just 11% cross the 50-episode mark. Just think about that with anything you commit to, right? It might not be these exact percentages. It probably won't be a podcast, but maybe. But no matter what you choose, if you do something 50 times, you are going to be in an elite tier of whatever that is.
I want you to take a moment and honestly assess what you're currently doing in your business and more importantly, what you're avoiding. If you're still in corporate and dreaming of your exit, maybe you've mentioned starting a business to your partner, you've listened to a few episodes of this podcast, but you haven't taken concrete steps yet. That's okay.
Your First 50 could be listening to 50 business-focused podcast episodes. And yes, there are thousands besides mine. It could be having 50 coffee chats with entrepreneurs to learn about their early days. It could be attending 50 virtual or in-person networking events. It could be journaling for 50 days about potential business ideas and your vision.
If you have a business idea, but maybe you're struggling to take action in your business, your First 50 might focus on industry connection and validation. Right? So maybe it's attending 50 industry-specific networking events or events in general, right? Maybe conferences or talks, speeches. Maybe your 50 will be conducting 50 marketing research calls with your ideal clients or 50 connections with other female entrepreneurs in your field. Maybe it's setting up 50 calls or connections with family and friends where you are simply talking to them about what you're doing and ask them what they think, getting better at explaining what you want to do and explaining what you've done so far.
Now, if your business is a little bit further along and maybe you're working on visibility and client attraction, maybe you know you need to be more visible but hesitate to put yourself out there. So maybe your First 50 would be social media or LinkedIn posts or emails to your email list, even if it's tiny. Maybe it's pitching yourself as a guest on 50 podcasts.
Now, what I want you to notice about that one specifically is that it is still completely in your control to reach out to 50 podcasts and pitch yourself, right? We are not depending on that podcast host to say yes in order for us to feel like we are making progress. It is just the act of getting better and cleaner at making that pitch. Or maybe it's having 50 consultations or sales conversations.
On that note, here's something important that I want you to consider is that this challenge doesn't have to involve something completely new to you and your business. It could be something you've already been doing but want to improve. So if you've done plenty of sales calls, but your conversion rates are low or not where you want them to be, go ahead and make your First 50 about intentional tracked sales conversations.
It doesn't have to be the first time you're doing these 50; it could be the next 50 of whatever that is, which I'll talk about in a second. But really, this is going to be the first 50, say, sales calls that you are doing it with this intentional process. So don't hold yourself back in that area.
I love thinking about this like strength training, right? And building muscles. If you committed to, let's say, 10 pushups every day for 50 days, the first day would be exhausting. I'd definitely be on my knees with terrible form. But by the 50th day of doing that, not only would those pushups be easier, but my form would be excellent, and I'd be significantly stronger. And it's not just about, this isn't about doing something 50 days straight. That's not what I'm talking about at all. But even if you committed to doing 10 pushups every other day or 10 pushups three times a week for 50 attempts, on that 50th attempt, you are going to be so much stronger than you were on the first and second. We are building this muscle.
So I want you to choose an area where you're currently holding back, where you're hiding, where you're struggling to take consistent action. And this isn't just about going through the motions. It's actually the exact opposite. We're treating these 50 attempts as your personal business classroom, which by the way is your free personal business classroom. So you're in training mode, learning through deliberate practice.
In last week's episode, I talked about making investments in your business. And this challenge is an investment in your business. It's free, but it's an investment of your time. The real challenge is that it's hard to embrace learning mode when we're judging ourselves, thinking we should already be experts at everything. But that's exactly why this challenge and framework is so powerful.
So I want you to identify your classroom, that skill or activity you want to level up. Then it's all about committing and executing, which I'm going to give you really clear instructions on next because we want to talk about actually making it happen. This is where most mom entrepreneurs hit a wall, myself included, for sure, until this podcast actually. And that is consistency.
I want to be real about what you are committing to here when you commit to these First 50. If you're doing something weekly like this podcast, that's nearly a year. If you're targeting 50 networking events, even at two per week, that's still six months. But here's the shift that I want you to consider is that the longevity is a hidden benefit and tool.
When you complete all 50, you won't just be better at the skill itself; you'll have built unshakable trust in yourself to follow through. I know that might make some of you nervous if you tend to bounce between ideas or if you've never been able to commit to something before and really prove to yourself that you can stick with something. And that's exactly why I want you to choose something truly aligned with where your business is right now. And I want you to meet yourself exactly where you are without judgment.
This podcast, one of the reasons that it came to fruition was because I failed so often at staying consistent with taking the value that I had in my beautiful brain, which is both the problem and the solution, and sharing that value on a consistent basis, right? I tried blogging, I tried social media posting, I tried LinkedIn posts, but nothing felt like I could be consistent and stick with it.
I knew though that I would be able to do it with a podcast, and that would have a ripple effect on all other areas of my business where I wasn't staying consistent. Okay? And I'll talk about why in just a second, because you don't need a podcast to necessarily have success with this First 50 challenge.
But I want you to be intentional and find your thing, something that's truly aligned with where you're at. Something that is challenging, right? I mean, this is challenging no matter what, doing 50 of anything. But I want to make sure that you are thinking about it in a way that makes sure it aligns with you.
And let me clarify something important about this challenge. I've mentioned it earlier, but it's not about never missing a day or a week, right? It's about completing the full experience of 50 attempts of something. For this podcast, I committed to weekly episodes, but before maternity leave, I batch recorded 12 episodes in advance.
I wasn't actively working on the podcast for three months, but I still created the full 50 episodes and learned from the full 50 episodes. And you better believe I learned more about myself while batching 12 episodes while growing a human being and showing up in my business than I do most weeks when I'm not growing a human being and batching 12 episodes.
So, I want to share a six-step process for you to commit and execute on this. The first step is make a clear decision quickly. Choose your First 50 activity thoughtfully, but don't overthink it. If you spend a week deciding, that's seven days of valuable brain space that is spent on something that should take less than one hour. And if you need help deciding, email me at Jenna@jenna.coach, right? That's literally what coaches do. We help you make decisions.
So, utilize the resource and make a decision quickly. Hold yourself accountable to faster decisions knowing that owning a business and starting a business is full of endless decisions, and you want to make this decision quickly and intentionally so that you can move on to the next one.
The next thing is I want you to calculate your true time investment. I want you to be honest about how long each attempt will take, including preparation time. So if you're committing to 50 networking events, that's probably an hour per event, at least, plus maybe 15 to 30 minutes a week of finding and registering for those events.
If you are doing something with email marketing, let's say, if you're committing to sending 50 emails to your list, how long will each email really take to produce? Early in my business, creating just one email took me hours, sometimes days. They weren't even good. If you know perfectionism will creep in, account for that time realistically.
The incredible thing is that as you progress from novice to skilled in these areas, your time investment drastically decreases. Now I can create an email in under 30 minutes because I've built systems, right? I worry less about the judgment and I know my audience better. Like I mentioned earlier just before this, I created an email in less than 10 minutes.
The third step is to expect uncovering additional needs along the way. Through your 50 attempts, you'll discover gaps that need fixing. You'll discover other things you need to focus on. You'll discover exciting new challenges in the business. When I first started the podcast, I was using a software to record called Audacity, and I had countless issues. It felt like every week I was fighting the system, and around Episode 35, I switched to Riverside, which I use now, and it was a hallelujah moment.
It was like so much easier to use and had so many more features and has benefited me so much. Your First 50 will reveal similar insights. Maybe you need better systems, a more specific audience, or different tools. And that is one of the benefits of this challenge. This challenge becomes a diagnostic for your entire business. One of these steps in the framework is to expect that. Nothing has gone wrong; it's part of the process to figure things out along the way beyond just the attempts themselves.
The next step is to schedule it, non-negotiably. Once you've committed, schedule your First 50 attempts in your calendar, not just the next one. Block time for at least the first 10 to 25 attempts. Maybe you're not able to block off and schedule the First 50.
Maybe if you're doing a networking event and you don't know what those networking events are, maybe you're just blocking off a couple hours each week to actually schedule those networking events, right? Or to find those networking events. If you don't have a reliable calendar system, that's priority number one, okay? It's likely holding you back in multiple areas of your businesses. So, make sure that you are using a calendar system that works for you and that works well.
The next step is add intentional evaluation after each attempt. This is a game-changer most people miss. Don't just go through the motions. That's what we're likely already doing. I want this to be different. I want you to treat each attempt as a learning opportunity. This is the most transformational piece, and I talked about it a lot in Episode 49, but I want you to also see how it applies here.
What typically happens when we repeat something in our business, we go through the motions, ticking the boxes, feeling accomplished just for showing up. And don't get me wrong, showing up consistently is huge. But there's a massive difference between repetition and deliberate practice. It's like the saying, practice makes perfect is wrong, right? It's like perfect practice makes perfect. And granted, we are removing perfect from the goal, but what it means is that we need to be intentional about the practice. We aren't just going through the motions. It's not just showing up that gets us there; it's showing up intentionally.
Most of us are unconsciously operating on autopilot. We send the email, attend the networking event, create the content, and then immediately move on to the next thing on our never-ending mom business to-do list, okay? We're so focused on completion that we miss the goldmine of learning available in each attempt. So we need to slow down. I want you to think about what you're doing right now with recurring tasks in your business.
When you finish a sales call and maybe you either celebrate booking the client or you beat yourself up for not converting, but you don't systematically analyze what happened. We might publish a social media post, check likes a few times, and move on without studying which elements resonated and why, or what we could have done better in our caption or in the visual.
And this is the pattern I want to break with the First 50 framework. So instead of mindless repetition, I want us to implement reflective practice, a deliberate pause after each attempt to extract the learning. And this really turns the 50 attempts from a marathon of tasks into a personalized business masterclass. And that pause and reflect moment is as easy as asking yourself, what went well? What didn't go well? And what will I do differently next time? Okay?
I mentioned these questions in Episode 49 as well and how to use them to make the most of any business investment. And I want you to think of this challenge not necessarily as a monetary investment, but as a time investment that you're making in your life and business. These 50 attempts are an investment of your most valuable non-renewable resource. And so you want to make sure you make the most of it, which by the way is time, if you've never heard that phrase.
So I want you to document it, make sure you have a digital note, a notebook, voice memos, whatever it is, but really capturing those insights to solidify your learning. When I started this podcast, I was honestly just relieved to get each episode done. I didn't systematically evaluate what was working and what wasn't. Of course, I had my team that was helping me evaluate along the way, but I wasn't doing that work myself in a really intentional and thoughtful way. I certainly grew naturally through the process and through the experience of creating, recording, and publishing 50 episodes.
But imagine if I'd intentionally reviewed each episode's content, delivery, and impact. I would have accelerated my growth exponentially, right? And this is the difference between passive growth and accelerated mastery. Without evaluation, you might improve 10% over 50 attempts, but with intentional evaluation, you could see 200 to 300% improvement in the same timeframe.
Now, here's the thing. I didn't go into this 50 podcast episode effort being intentional about growing each episode. The First 50 concept came to me in celebration of making it to 50 and being able to recognize my own growth and evolution in that process. I will commit to this process for the next 50 episodes, and you'll be able to see the evolution yourself, knowing the work that's going in on the back end to keep improving. Which by the way, only 7% of podcasts make it to 100 episodes, so I'm excited to be in that company this time next year as well.
Okay, so real quick, just some examples that might help. If you're committing to attending 50 networking events, I want you to think about after each event looking at, like maybe evaluating your introduction and how you introduced yourself. Maybe you need to do that differently next time. Maybe it didn't go so well. Maybe next time you'd want to multitask less if it's a virtual event. Maybe you want to be more active in the chat.
If it's in person, maybe you want to meet more people or set up one-on-ones after the event. Maybe next time you want to go up to people and approach them first. Maybe you want to shower before the event, right? Or get a nice jacket or outfit to wear to it. There are so many things that you can do differently and that you can evaluate in what went well and what didn't go well, no matter what you're committing to.
The last step, and this is really the most important step in this entire process, I will say, is to build in accountability, create accountability. This step is non-negotiable. There is no way I would have created 50 consistent podcast episodes without hiring a production company that enforces deadlines and charges late fees. Having a team that would push back if I considered skipping a week made it much harder to quit on myself or skip a week. They'd even probably suggest alternatives like they did around the holidays of how to repurpose content or, you know, do a quicker episode that would save me time and energy.
It is amazing also to have people cheering me on. I've been so energized by their positive feedback throughout the process, and they also have made me better by offering strategic expertise along the way, right? So some of the evaluation that I talked about has come from other experts. And you don't need to hire someone for this challenge.
When I'm talking about accountability, I'm not necessarily talking about hiring a production team or hiring a coach or hiring a mentor. But you absolutely need some form of accountability because sticking with something for six months or a year or however long the 50 attempts takes you is going to be something that is challenging to do without support.
I want you to tell a friend or a partner and ask them to check in weekly, right? Join a Facebook group and post your progress. Find an accountability buddy, also doing their own First 50, right? Share your commitment in a walking group that you're a part of, right? Get creative. Share the commitment with me. Trust me, I am a great cheerleader.
It's so funny. I cheered for like maybe a year of my life when I was like seven years old. But then, of course, I played softball growing up, which if you know softball and you know constant cheering on the sidelines. And I played basketball, which for my high school, they had cheerleaders. But all this to say that in my household, I'm constantly reciting cheers, and my husband Chris finds it hilarious sometimes and also really annoying sometimes, but I don't care. I literally have a cheer for every situation in life that I pull forward from our past or from my past.
So yes, email me at jenna@jenna.coach, J-E-N-N-A, and I will be your cheerleader. I even have my free Mom Entrepreneur Circle that meets monthly that you can come to for in-person accountability on a monthly basis. Whatever form it takes, external accountability is what will get you to number 50. I promise.
Now, let's talk about what you'll gain from this challenge because some of it's obvious and then some of it's not so obvious. And I want you to have a lot of motivation going into this about why it could be a really exciting and fun challenge for you at whatever stage you're in your business.
While signing clients or generating income might happen as a result, right? Like there are definitely clients that have come to me through this podcast and there's revenue that's been generated from this podcast in different ways. And that would be amazing for that to be a result of your First 50 to generate income. But that's not the primary goal here.
The true results of this challenge are far more valuable and long-lasting, okay? Because first, you're going to develop genuine expertise. And I've talked about that a lot. Those networking events where you once felt awkward, you're going to walk in with natural confidence and general connection skills, right? The emails that used to take hours to write, you'll craft messages in 30 minutes or less. That weekly planning ritual that you've been trying to establish, it will become as automatic as brushing your teeth by the 50th attempt.
You'll also reclaim precious time and energy. I've mentioned this a number of times. As a mom entrepreneur, these are your most limited resources, time and energy. So when tasks that once drained you become second nature, you free up mental bandwidth for strategic thinking and creative problem solving, or maybe even you can take a break and practice self-care.
The other thing is that you will develop systems that stick. Through those 50 attempts, you'll naturally create processes that work specifically for you. Not cookie cutter-templates necessarily from someone else's business, but custom approaches born from your own experience, right? You'll learn more about what works and what doesn't work. And you'll start to naturally create a system for that because if we're going to do something 50 times, we are going to create a system around it, not just how to do it, but how to do it efficiently.
And of course, the First 50 Challenge isn't the only thing that you're doing in your business during this time. It's simply one area where you're intentionally embracing the learning curve instead of expecting immediate perfection. And that shift alone is going to be revolutionary.
So here we are at Episode 50, a milestone that honestly felt impossibly far away when I recorded episode one last June. If there's one thing I want you to take away from this journey we've shared, it's that your business grows when you grow. And growth happens through consistent intentional action. Your First 50 doesn't have to be podcast episodes like mine; it could be sales calls, networking, planning rituals, right? The specific activity matters less than your commitment to showing up as a student, ready to learn through doing rather than perfect planning.
And again, I'd love to hear what your First 50 will be. Send me an email, jenna@jenna.coach. And for those who want support in choosing and implementing their First 50, join my free Mom Entrepreneur Circle. It can be a great networking space for you if you're going that route, but it can also be a great space for accountability and inspiration.
Thank you for celebrating this milestone with me. I would love for you to leave a review on the podcast. Let me know what's working, what's not working, and what you'd like me to do differently next episode so I can continue to grow and evolve each episode. I am cheering you on every step of the way, and I'll see you next week for the first episode of my next 50 on my way to 100.
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.
Today, in celebration of our 50th episode milestone, I'm giving you this same transformative tool: a framework I call Your First 50. By the end of today's episode, you'll have a practical roadmap to master any business skill that feels challenging right now and a process for exponential growth through intentional repetition.
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. So, this is episode 50. Can you believe it? 50 weeks of showing up, sharing strategies, and building this community together. It dawned on me when my husband and I were both working at the kitchen table one Friday when I was putting the content together. And I was going to talk about competition in this episode, but he was like, absolutely not. You have to do something special for the episode. So here we are.
This milestone got me thinking about the power of consistency and repetition in business growth. Who I was on episode one last June is completely different from who I am today. And it's not just about the time passing; it's about the experience, the learning, and the momentum that comes from committing to and doing something 50 times, which is not a small number. It reminds me of Malcolm Gladwell's talking about the 20,000 hours concept to mastering any skill.
That's why today, I want to talk about a powerful concept that can revolutionize how you approach your business. And this is really exciting because this concept isn't something that I've had as a tool in my business. It's something that has evolved in my reflection of this 50-episode milestone. And so I don't even have a cheeky name for it. So we'll just call it the First 50 Challenge.
And no matter where you're at in starting a business, even if you have no intentions of starting a business, this challenge can be applied to almost any skill or task that you want to improve on. So if you're still in corporate, just starting a business, or tackling growth mode in your business, this challenge will be an opportunity to transform how you develop any skill in your business or in life really. And I will give examples of each of those.
So, here's what I want to talk about in this episode. I'm going to introduce the First 50 Challenge and why committing to it builds unstoppable momentum. We'll talk about how to identify the perfect skill or task for you to focus on for the specific business stage you're in. I'll share a practical system for committing and executing with intention, which is really the meat and bones of this episode, and what happens after completing the challenge and how to leverage your new experience.
The beauty of this approach is that it's going to eliminate perfectionism, which is a topic that has been coming up a lot recently with my clients. Similarly, it builds self-trust and creates tangible results, all the while being 100% within your control as a busy mom entrepreneur, which I will talk more about in a few minutes.
But on the topic of perfectionism, since that keeps coming up in my sessions. When we are working on our businesses, especially early on, we get caught up in the perfectionism trap. So we treat each task like it needs to be flawless before we can put it out into the world. This perfectionism isn't just slowing us down; it's absolutely paralyzing us and consuming precious energy that we just don't have as moms, okay?
So, I want to share a behind-the-scenes look at this podcast. Those first podcast episodes took me hours to create. I'm somebody who really likes to do the pre-work, map out what I'm going to say, really put thought into the script, into the points that I'm making, and really workshop it before I go live. And like I said, it took me hours to do that for my first few episodes. I would obsess over every word. I'd re-record sections multiple times and still feel anxiety when I was sending it off to my team and when they were then publishing it and when it was going live.
So fast forward to now, the process is smoother, faster, and honestly way more enjoyable. When I analyze my first 25 episodes versus my most recent 25, the difference is striking, right? The content now is more focused because I've really learned what resonates with you, my listeners. My delivery is more confident. My systems are more efficient, from planning to recording to promotion. I even upgraded my tech along the way, recently adding better lighting and a camera for future video content.
And when I'm promoting my podcast episodes each week, again, that used to take me hours, even with the help of my team. Now, I literally can do it. I just did it right before for the episode prior to this, and it literally took me 10 minutes. So it's amazing how much time we can save and how much less energy we need once we become more proficient in what we're doing.
So what I want you to really understand is that growth didn't happen with this podcast because I waited until I was ready. It happened because I was willing to be imperfect 50 times in a row. When we're on attempt one of anything, our brain spirals with questions. We're asking, will this work? Will I get anything out of it? What will the results be? That mental chatter pulls us out of learning mode and into judgment.
But the magic of committing to 50 attempts is that it completely shifts your mindset. Suddenly, those first few attempts are allowed to be, excuse my English, or French, shitty first drafts, okay? They're supposed to be. Doing anything new is scary, and your brain will absolutely freak out, and that's completely normal. But when you promise yourself 50 tries to improve, you release the pressure on those early attempts. You give yourself permission to be a beginner, which is incredibly freeing for perfectionist moms who are used to being excellent at everything, like myself.
Getting this mental drama out of your head is a complete game-changer. It allows you to experiment and take risks, knowing that improvement is the goal, not perfection. And we'll talk more about exactly how to ensure you're getting better each time in a minute, which is absolutely critical.
But what I also want to offer is that completing all 50 attempts is a goal that's 100% in your control. It doesn't depend on anyone else saying yes, paying you money, or making decisions. It's simply you committing to something that you can repeat 50 times, which builds massive self-trust and momentum. This is the full ownership I talked about in last week's episode, okay?
And yes, 50 is a big number. I've been told by my podcast team that I'm now part of an elite tier of podcasters, okay? Only 49% make it to episode 8, and just 11% cross the 50-episode mark. Just think about that with anything you commit to, right? It might not be these exact percentages. It probably won't be a podcast, but maybe. But no matter what you choose, if you do something 50 times, you are going to be in an elite tier of whatever that is.
I want you to take a moment and honestly assess what you're currently doing in your business and more importantly, what you're avoiding. If you're still in corporate and dreaming of your exit, maybe you've mentioned starting a business to your partner, you've listened to a few episodes of this podcast, but you haven't taken concrete steps yet. That's okay.
Your First 50 could be listening to 50 business-focused podcast episodes. And yes, there are thousands besides mine. It could be having 50 coffee chats with entrepreneurs to learn about their early days. It could be attending 50 virtual or in-person networking events. It could be journaling for 50 days about potential business ideas and your vision.
If you have a business idea, but maybe you're struggling to take action in your business, your First 50 might focus on industry connection and validation. Right? So maybe it's attending 50 industry-specific networking events or events in general, right? Maybe conferences or talks, speeches. Maybe your 50 will be conducting 50 marketing research calls with your ideal clients or 50 connections with other female entrepreneurs in your field. Maybe it's setting up 50 calls or connections with family and friends where you are simply talking to them about what you're doing and ask them what they think, getting better at explaining what you want to do and explaining what you've done so far.
Now, if your business is a little bit further along and maybe you're working on visibility and client attraction, maybe you know you need to be more visible but hesitate to put yourself out there. So maybe your First 50 would be social media or LinkedIn posts or emails to your email list, even if it's tiny. Maybe it's pitching yourself as a guest on 50 podcasts.
Now, what I want you to notice about that one specifically is that it is still completely in your control to reach out to 50 podcasts and pitch yourself, right? We are not depending on that podcast host to say yes in order for us to feel like we are making progress. It is just the act of getting better and cleaner at making that pitch. Or maybe it's having 50 consultations or sales conversations.
On that note, here's something important that I want you to consider is that this challenge doesn't have to involve something completely new to you and your business. It could be something you've already been doing but want to improve. So if you've done plenty of sales calls, but your conversion rates are low or not where you want them to be, go ahead and make your First 50 about intentional tracked sales conversations.
It doesn't have to be the first time you're doing these 50; it could be the next 50 of whatever that is, which I'll talk about in a second. But really, this is going to be the first 50, say, sales calls that you are doing it with this intentional process. So don't hold yourself back in that area.
I love thinking about this like strength training, right? And building muscles. If you committed to, let's say, 10 pushups every day for 50 days, the first day would be exhausting. I'd definitely be on my knees with terrible form. But by the 50th day of doing that, not only would those pushups be easier, but my form would be excellent, and I'd be significantly stronger. And it's not just about, this isn't about doing something 50 days straight. That's not what I'm talking about at all. But even if you committed to doing 10 pushups every other day or 10 pushups three times a week for 50 attempts, on that 50th attempt, you are going to be so much stronger than you were on the first and second. We are building this muscle.
So I want you to choose an area where you're currently holding back, where you're hiding, where you're struggling to take consistent action. And this isn't just about going through the motions. It's actually the exact opposite. We're treating these 50 attempts as your personal business classroom, which by the way is your free personal business classroom. So you're in training mode, learning through deliberate practice.
In last week's episode, I talked about making investments in your business. And this challenge is an investment in your business. It's free, but it's an investment of your time. The real challenge is that it's hard to embrace learning mode when we're judging ourselves, thinking we should already be experts at everything. But that's exactly why this challenge and framework is so powerful.
So I want you to identify your classroom, that skill or activity you want to level up. Then it's all about committing and executing, which I'm going to give you really clear instructions on next because we want to talk about actually making it happen. This is where most mom entrepreneurs hit a wall, myself included, for sure, until this podcast actually. And that is consistency.
I want to be real about what you are committing to here when you commit to these First 50. If you're doing something weekly like this podcast, that's nearly a year. If you're targeting 50 networking events, even at two per week, that's still six months. But here's the shift that I want you to consider is that the longevity is a hidden benefit and tool.
When you complete all 50, you won't just be better at the skill itself; you'll have built unshakable trust in yourself to follow through. I know that might make some of you nervous if you tend to bounce between ideas or if you've never been able to commit to something before and really prove to yourself that you can stick with something. And that's exactly why I want you to choose something truly aligned with where your business is right now. And I want you to meet yourself exactly where you are without judgment.
This podcast, one of the reasons that it came to fruition was because I failed so often at staying consistent with taking the value that I had in my beautiful brain, which is both the problem and the solution, and sharing that value on a consistent basis, right? I tried blogging, I tried social media posting, I tried LinkedIn posts, but nothing felt like I could be consistent and stick with it.
I knew though that I would be able to do it with a podcast, and that would have a ripple effect on all other areas of my business where I wasn't staying consistent. Okay? And I'll talk about why in just a second, because you don't need a podcast to necessarily have success with this First 50 challenge.
But I want you to be intentional and find your thing, something that's truly aligned with where you're at. Something that is challenging, right? I mean, this is challenging no matter what, doing 50 of anything. But I want to make sure that you are thinking about it in a way that makes sure it aligns with you.
And let me clarify something important about this challenge. I've mentioned it earlier, but it's not about never missing a day or a week, right? It's about completing the full experience of 50 attempts of something. For this podcast, I committed to weekly episodes, but before maternity leave, I batch recorded 12 episodes in advance.
I wasn't actively working on the podcast for three months, but I still created the full 50 episodes and learned from the full 50 episodes. And you better believe I learned more about myself while batching 12 episodes while growing a human being and showing up in my business than I do most weeks when I'm not growing a human being and batching 12 episodes.
So, I want to share a six-step process for you to commit and execute on this. The first step is make a clear decision quickly. Choose your First 50 activity thoughtfully, but don't overthink it. If you spend a week deciding, that's seven days of valuable brain space that is spent on something that should take less than one hour. And if you need help deciding, email me at Jenna@jenna.coach, right? That's literally what coaches do. We help you make decisions.
So, utilize the resource and make a decision quickly. Hold yourself accountable to faster decisions knowing that owning a business and starting a business is full of endless decisions, and you want to make this decision quickly and intentionally so that you can move on to the next one.
The next thing is I want you to calculate your true time investment. I want you to be honest about how long each attempt will take, including preparation time. So if you're committing to 50 networking events, that's probably an hour per event, at least, plus maybe 15 to 30 minutes a week of finding and registering for those events.
If you are doing something with email marketing, let's say, if you're committing to sending 50 emails to your list, how long will each email really take to produce? Early in my business, creating just one email took me hours, sometimes days. They weren't even good. If you know perfectionism will creep in, account for that time realistically.
The incredible thing is that as you progress from novice to skilled in these areas, your time investment drastically decreases. Now I can create an email in under 30 minutes because I've built systems, right? I worry less about the judgment and I know my audience better. Like I mentioned earlier just before this, I created an email in less than 10 minutes.
The third step is to expect uncovering additional needs along the way. Through your 50 attempts, you'll discover gaps that need fixing. You'll discover other things you need to focus on. You'll discover exciting new challenges in the business. When I first started the podcast, I was using a software to record called Audacity, and I had countless issues. It felt like every week I was fighting the system, and around Episode 35, I switched to Riverside, which I use now, and it was a hallelujah moment.
It was like so much easier to use and had so many more features and has benefited me so much. Your First 50 will reveal similar insights. Maybe you need better systems, a more specific audience, or different tools. And that is one of the benefits of this challenge. This challenge becomes a diagnostic for your entire business. One of these steps in the framework is to expect that. Nothing has gone wrong; it's part of the process to figure things out along the way beyond just the attempts themselves.
The next step is to schedule it, non-negotiably. Once you've committed, schedule your First 50 attempts in your calendar, not just the next one. Block time for at least the first 10 to 25 attempts. Maybe you're not able to block off and schedule the First 50.
Maybe if you're doing a networking event and you don't know what those networking events are, maybe you're just blocking off a couple hours each week to actually schedule those networking events, right? Or to find those networking events. If you don't have a reliable calendar system, that's priority number one, okay? It's likely holding you back in multiple areas of your businesses. So, make sure that you are using a calendar system that works for you and that works well.
The next step is add intentional evaluation after each attempt. This is a game-changer most people miss. Don't just go through the motions. That's what we're likely already doing. I want this to be different. I want you to treat each attempt as a learning opportunity. This is the most transformational piece, and I talked about it a lot in Episode 49, but I want you to also see how it applies here.
What typically happens when we repeat something in our business, we go through the motions, ticking the boxes, feeling accomplished just for showing up. And don't get me wrong, showing up consistently is huge. But there's a massive difference between repetition and deliberate practice. It's like the saying, practice makes perfect is wrong, right? It's like perfect practice makes perfect. And granted, we are removing perfect from the goal, but what it means is that we need to be intentional about the practice. We aren't just going through the motions. It's not just showing up that gets us there; it's showing up intentionally.
Most of us are unconsciously operating on autopilot. We send the email, attend the networking event, create the content, and then immediately move on to the next thing on our never-ending mom business to-do list, okay? We're so focused on completion that we miss the goldmine of learning available in each attempt. So we need to slow down. I want you to think about what you're doing right now with recurring tasks in your business.
When you finish a sales call and maybe you either celebrate booking the client or you beat yourself up for not converting, but you don't systematically analyze what happened. We might publish a social media post, check likes a few times, and move on without studying which elements resonated and why, or what we could have done better in our caption or in the visual.
And this is the pattern I want to break with the First 50 framework. So instead of mindless repetition, I want us to implement reflective practice, a deliberate pause after each attempt to extract the learning. And this really turns the 50 attempts from a marathon of tasks into a personalized business masterclass. And that pause and reflect moment is as easy as asking yourself, what went well? What didn't go well? And what will I do differently next time? Okay?
I mentioned these questions in Episode 49 as well and how to use them to make the most of any business investment. And I want you to think of this challenge not necessarily as a monetary investment, but as a time investment that you're making in your life and business. These 50 attempts are an investment of your most valuable non-renewable resource. And so you want to make sure you make the most of it, which by the way is time, if you've never heard that phrase.
So I want you to document it, make sure you have a digital note, a notebook, voice memos, whatever it is, but really capturing those insights to solidify your learning. When I started this podcast, I was honestly just relieved to get each episode done. I didn't systematically evaluate what was working and what wasn't. Of course, I had my team that was helping me evaluate along the way, but I wasn't doing that work myself in a really intentional and thoughtful way. I certainly grew naturally through the process and through the experience of creating, recording, and publishing 50 episodes.
But imagine if I'd intentionally reviewed each episode's content, delivery, and impact. I would have accelerated my growth exponentially, right? And this is the difference between passive growth and accelerated mastery. Without evaluation, you might improve 10% over 50 attempts, but with intentional evaluation, you could see 200 to 300% improvement in the same timeframe.
Now, here's the thing. I didn't go into this 50 podcast episode effort being intentional about growing each episode. The First 50 concept came to me in celebration of making it to 50 and being able to recognize my own growth and evolution in that process. I will commit to this process for the next 50 episodes, and you'll be able to see the evolution yourself, knowing the work that's going in on the back end to keep improving. Which by the way, only 7% of podcasts make it to 100 episodes, so I'm excited to be in that company this time next year as well.
Okay, so real quick, just some examples that might help. If you're committing to attending 50 networking events, I want you to think about after each event looking at, like maybe evaluating your introduction and how you introduced yourself. Maybe you need to do that differently next time. Maybe it didn't go so well. Maybe next time you'd want to multitask less if it's a virtual event. Maybe you want to be more active in the chat.
If it's in person, maybe you want to meet more people or set up one-on-ones after the event. Maybe next time you want to go up to people and approach them first. Maybe you want to shower before the event, right? Or get a nice jacket or outfit to wear to it. There are so many things that you can do differently and that you can evaluate in what went well and what didn't go well, no matter what you're committing to.
The last step, and this is really the most important step in this entire process, I will say, is to build in accountability, create accountability. This step is non-negotiable. There is no way I would have created 50 consistent podcast episodes without hiring a production company that enforces deadlines and charges late fees. Having a team that would push back if I considered skipping a week made it much harder to quit on myself or skip a week. They'd even probably suggest alternatives like they did around the holidays of how to repurpose content or, you know, do a quicker episode that would save me time and energy.
It is amazing also to have people cheering me on. I've been so energized by their positive feedback throughout the process, and they also have made me better by offering strategic expertise along the way, right? So some of the evaluation that I talked about has come from other experts. And you don't need to hire someone for this challenge.
When I'm talking about accountability, I'm not necessarily talking about hiring a production team or hiring a coach or hiring a mentor. But you absolutely need some form of accountability because sticking with something for six months or a year or however long the 50 attempts takes you is going to be something that is challenging to do without support.
I want you to tell a friend or a partner and ask them to check in weekly, right? Join a Facebook group and post your progress. Find an accountability buddy, also doing their own First 50, right? Share your commitment in a walking group that you're a part of, right? Get creative. Share the commitment with me. Trust me, I am a great cheerleader.
It's so funny. I cheered for like maybe a year of my life when I was like seven years old. But then, of course, I played softball growing up, which if you know softball and you know constant cheering on the sidelines. And I played basketball, which for my high school, they had cheerleaders. But all this to say that in my household, I'm constantly reciting cheers, and my husband Chris finds it hilarious sometimes and also really annoying sometimes, but I don't care. I literally have a cheer for every situation in life that I pull forward from our past or from my past.
So yes, email me at jenna@jenna.coach, J-E-N-N-A, and I will be your cheerleader. I even have my free Mom Entrepreneur Circle that meets monthly that you can come to for in-person accountability on a monthly basis. Whatever form it takes, external accountability is what will get you to number 50. I promise.
Now, let's talk about what you'll gain from this challenge because some of it's obvious and then some of it's not so obvious. And I want you to have a lot of motivation going into this about why it could be a really exciting and fun challenge for you at whatever stage you're in your business.
While signing clients or generating income might happen as a result, right? Like there are definitely clients that have come to me through this podcast and there's revenue that's been generated from this podcast in different ways. And that would be amazing for that to be a result of your First 50 to generate income. But that's not the primary goal here.
The true results of this challenge are far more valuable and long-lasting, okay? Because first, you're going to develop genuine expertise. And I've talked about that a lot. Those networking events where you once felt awkward, you're going to walk in with natural confidence and general connection skills, right? The emails that used to take hours to write, you'll craft messages in 30 minutes or less. That weekly planning ritual that you've been trying to establish, it will become as automatic as brushing your teeth by the 50th attempt.
You'll also reclaim precious time and energy. I've mentioned this a number of times. As a mom entrepreneur, these are your most limited resources, time and energy. So when tasks that once drained you become second nature, you free up mental bandwidth for strategic thinking and creative problem solving, or maybe even you can take a break and practice self-care.
The other thing is that you will develop systems that stick. Through those 50 attempts, you'll naturally create processes that work specifically for you. Not cookie cutter-templates necessarily from someone else's business, but custom approaches born from your own experience, right? You'll learn more about what works and what doesn't work. And you'll start to naturally create a system for that because if we're going to do something 50 times, we are going to create a system around it, not just how to do it, but how to do it efficiently.
And of course, the First 50 Challenge isn't the only thing that you're doing in your business during this time. It's simply one area where you're intentionally embracing the learning curve instead of expecting immediate perfection. And that shift alone is going to be revolutionary.
So here we are at Episode 50, a milestone that honestly felt impossibly far away when I recorded episode one last June. If there's one thing I want you to take away from this journey we've shared, it's that your business grows when you grow. And growth happens through consistent intentional action. Your First 50 doesn't have to be podcast episodes like mine; it could be sales calls, networking, planning rituals, right? The specific activity matters less than your commitment to showing up as a student, ready to learn through doing rather than perfect planning.
And again, I'd love to hear what your First 50 will be. Send me an email, jenna@jenna.coach. And for those who want support in choosing and implementing their First 50, join my free Mom Entrepreneur Circle. It can be a great networking space for you if you're going that route, but it can also be a great space for accountability and inspiration.
Thank you for celebrating this milestone with me. I would love for you to leave a review on the podcast. Let me know what's working, what's not working, and what you'd like me to do differently next episode so I can continue to grow and evolve each episode. I am cheering you on every step of the way, and I'll see you next week for the first episode of my next 50 on my way to 100.
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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