3. When To Quit Your Job: The Importance of a Departure Date
When you decide you want to leave your job to become an entrepreneur, there's one more pivotal decision you need to make: when? Choosing your departure date feels heavy, but it's simpler than you think, and doing so is the first step to living the life you dream about every day. However, while choosing a departure date is simple, it comes with a ton of mental drama.
Not having a plan is one of the biggest obstacles that stops moms like us from living the lives we truly want. Sure, planning is difficult and even overwhelming, but when you choose a date and commit to making your transition into entrepreneurship, the rest of the plan will begin falling into place.
Tune in this week to discover why picking your departure date gives you the direction and clarity you need to make important changes in your life. I break down the mental drama you experience around deciding on a transition date for becoming an entrepreneur, and you'll learn how to choose a date and leverage the aligned certainty this decision will bring.
Ready to set your own departure date and take the next step to creating a life and business you love? Download the FREE accompanying action guide for this episode, by completing the form below!
If you enjoyed today’s show and don’t want to worry about missing an episode, be sure to follow the show wherever you listen to your podcasts. I would really appreciate it if you could share the podcast with others who you think would benefit, and leave a rating and review to let me know what you think!
What You’ll Learn from this Episode:
What 'meaningful action' is and how it gets you closer to where you want to go.
Why it took me six years between deciding I wanted to be an entrepreneur and actually becoming one.
The mental drama that accompanies the decision of when to quit your job and transition into entrepreneurship.
Why knowing when it's time to quit is vital, even if you've already left your job and are full-time in your own business.
What happens when you want to become an entrepreneur but you don't set a departure date from your corporate job.
The transformative effect of simply choosing a departure date and deciding to stick to it.
What you need to consider as you decide on a departure date to transition into entrepreneurship.
Listen to the Full Episode:
Featured on the Show:
Click here for step-by-step instructions to leave a rating and review to let me know what you think, and don’t forget to share the podcast with others who you think would benefit!
If you're looking for more support, check out my free Mom Entrepreneurs Circle. We meet monthly and you can click here to sign up!
Full Episode Transcript:
Do you ever feel like you’re just treading water, going nowhere fast in your corporate job? What if I told you that choosing a single date could be the key to changing everything? Today we’re diving into that one pivotal decision, your departure date. It’s simpler than you think, but that doesn’t mean it’s not without mental drama. And it’s your first real step towards the life you dream about every day.
Welcome to How to Quit Your Job: A Mom’s Guide to Creating a Life and Business You Love. It’s a podcast that helps working moms just like you, optimize your time, manage your mind, and start a business that helps you create more freedom, flexibility, and, yes, fun. I’m business and mindset coach Jenna Rykiel. And I offer practical tips to help you ditch the nine-to-five. I have been exactly where you are, and I know what it takes to make the transition without trading one form of burnout for another. So let’s get started.
Hello, good morning and good afternoon or good evening wherever you are today. It is morning where I am. I am trying to record this episode before my household wakes up. And my household right now is my parents, my husband, and my son. My husband and I are getting construction done on our house so we’re actually living with my parents in their quaint little rancher. And as soon as everyone wakes up, there will be so much noise. So, I am trying to get this podcast recorded for you before that happens. So, it is early, and I am sorry if I sound tired. I’m not as tired as I might sound. So, let’s go.
If you’re listening today, I know you’re someone who’s been thinking about making a change but maybe you’re stuck on how to start. You’ve got dreams, but turning them into reality feels daunting so let’s change that.
In today’s episode, we’re talking about a little thing called planning and not meal planning or vacation planning, but I’m sure you’re doing all those things, too. We’re talking about planning your transition date, the date when you’re going to be leaving your company to finally work on your own terms. Every few episodes I’m going to give you tangible tools to create and execute a plan so that you can make these hopes and dreams turn into a true reality and this is one of those episodes.
When I think about what my clients are missing or what they really believe is holding them back from creating a life and really career they love, not having a plan is one of the biggest obstacles. So, as promised, we’re going to solve that little by little on this podcast, and especially in this episode. I’m going to provide you with tangible and actionable bite sized steps that keep you moving forward in a way that feels manageable with all the other things you have going on.
One thing I preach constantly in my program is that meaningful action, which is defined by small consistent steps, is what leads to big changes over time. It’s not about massive action steps or giant leaps. Those things are scary and often create a situation where we actually avoid taking action altogether. I want you to start with meaningful action. So small steps that are a little uncomfortable, a little scary, but that allow you to work a new muscle, a taking action muscle.
So today I’m going to encourage you and give you the tools to take a meaningful action step that has to do with planning your departure date. And if you know my work at all or follow me on any social media, you’ll know that I talk about the importance of planning all the time. It’s another pillar of my coaching program because if it doesn’t get planned it doesn’t get done. And especially if it doesn’t get on the calendar, it doesn’t get done. And planning isn’t just for organized people or type A folks. It’s important for all of us who want to live a conscious and deliberate life.
And there are tools and systems that make planning and sticking to plans more doable. Planning is even more critical for moms like you because you’ve got a lot going on, but you’ve also got a lot of big dreams that aren’t going to achieve themselves. You have a dream of leaving your nine to five job behind and starting your own business. And the reality is that if it doesn’t get planned, it doesn’t get done. How many years have you been thinking about this?
I know for me, I’ve shared before it was about six years. Six years that I had this idea to start my own business because I had all the education. I had my coaching certification. I had a master’s in counseling. I earned my MBA. But every year, at the end of the year when my husband and I would sit down and do our New Year’s reflection, career would get a low rank. And I’d write something like, I’m capable of more or I’m not doing anything meaningful. Who can relate?
The years keep going by and we look back and nothing has gotten done or very little has gotten done to move the needle. And I don’t want you to be like Jenna then. I want you to be like Jenna now who has a wildly different way of thinking about herself and business with so many more tools to be able to consciously plan and take action. I want you to be in the business of getting things done, not just in your nine to five, not just at home, not just for the kids, not just for your partner. I want you to be in the business of getting things done that will radically change the trajectory of your life so that you’re living on your own terms and calling the shots.
So, like I said, we’re going to do that in tangible bite sized steps which are far less scary. We’re going to build a muscle. You need to take action because it’s a muscle and as you work it, it grows, taking action gets easier. Everything is a muscle that either grows or deteriorates. And I want you to be in the business of growing, not deteriorating. And a lot of you listening right now may feel like you’re deteriorating. I know I felt like that most days waking up and signing into a job that felt like it was holding me back from being the best version of myself.
And in this episode, we’re just taking our first bite of planning. And it’s an incredibly important element in the big picture of planning for your business. It’s going to be quick and trust me, there’s going to be a lot of mental drama. But when this one tangible item is planned and crossed off the to-do list, you’re going to be on your way to becoming your own boss.
So, let’s talk about deciding your departure date from corporate life. It should be easy enough. Maybe, maybe not. And if you’re sitting there and you’re like, “Boom, I’ve got my date, we’re good to go,” Or, “I left corporate a few months ago.” Then, kudos to you. You picked a date and made it happen. I encourage you to keep listening, because this doesn’t just have to apply to leaving your job. It can also be when you launch your first program or a date that you move to a different city.
Any big transition date in our life and our business we can sometimes delay making it happen because we haven’t been clear about the date of when it needs to happen. We’ll talk a lot more about why picking a date is so essential, but planning and picking that departure date gives you direction and clarity.
Let’s imagine you’re on a road trip and you have no idea when you’ll get to the destination. You’re just driving and driving and driving, I’ve driven across country a lot and I would never get in that car unless I knew the date that we’d be arriving. If you’re just driving with no timeline to consider, you’re aimlessly driving and you lose all purpose, you get antsy, anxious, and truly tired of being in the car. This is so many of you at your jobs right now, you’re antsy, anxious, and tired of being in your role.
You’re aimlessly showing up each day and not feeling good about it. I live in Maryland now. My husband and I moved back to where we’re from, to be close to family when my son Adley was born. But we lived in Denver for six years prior to that. And at least twice a year made the 26 hour drive because we were loving dog parents and our dog, Bubba, needed to be home with us, of course for all holidays and visits. So, we did that drive a lot. Never once did we get in that car without having a clear idea of when we wanted to be at our destination.
We planned our trip based on what day we needed to get back home. That informed so much about the trip. We could then plan where we would stay overnight and book the Airbnb. We had an idea of, if we left a day earlier, could we stay a day longer with a friend who was living in Dayton? You get the point. In order for the trip to be a success, we need to plan and that plan really starts with knowing when we get to our destination. It’s absolutely essential. And this isn’t always easy because there are a lot of factors involved.
And we will talk about all of those factors in just a couple of minutes. But our brain loves that clarity. And just to go off on another analogy tangent, just because you plan the arrival date, doesn’t mean the trip goes exactly as planned. We’ll talk about this at length on the podcast, the unexpected nature of kids and life because we all know that life with kids is unpredictable and that can present some obstacles for us in this venture.
My husband and I chose the date that we would be arriving. You can plan all the things in your trip, and then your van can have a belt blow in Park, Kansas. And if it’s a Sunday, you definitely aren’t getting that belt fixed. And so, you would absolutely need to be towed over four hours with your dog to get back to Denver. So yes, just because you have a plan doesn’t mean everything runs smoothly but it’s so much better to have a plan to work off of for that road trip than to just drive aimlessly, especially if kids are in the car.
And when it comes to quitting your job, planning starts with deciding your transition date. It’s the first step towards turning your dreams into reality. It’s knowing what day you want to get to that destination that you’ve been thinking about for however many years. The destination that allows you to wake up each day feeling like you’re doing work that’s meaningful and that you have control over your time.
So, let’s talk about and understand really the power of picking a departure date. It seems like such a small detail, but it’s so powerful. You’ve been at your job, comfortable, yet unfulfilled, always thinking about what could be. Like many, you might feel trapped in this endless cycle of some day. Setting a departure date, transforms that someday into a concrete plan. It’s about marking a day on your calendar that boldly states, this is when my new life starts. It’s not just about leaving a job, it’s about embracing a future that you control.
So, choosing a departure date might seem like a small administrative step in the grand scheme of leaving your job and starting your own business. However, it’s much more than just marking a day on your calendar. It’s about setting a powerful intention that can fundamentally change your approach, mindset, and actions. I want to sell you on this, not just why it’s so crucial, but also what could happen if you don’t set one and the transformative effect it can have once you do.
By the end of this episode, I want you to feel energized to take this one small, yet meaningful step, it’s like tipping the first domino. Let’s revisit why setting the date is so important, it creates a sense of urgency and commitment. Setting a departure date shifts your goals from the abstract, I want to start a business someday to the concrete, I’m starting a business on this specific date. This commitment creates a sense of urgency, which compels you to take action rather than allowing your ambitions to remain in this realm of daydreams.
Without a departure date on the calendar, it’s a daydream, one that takes up a lot of energy because it’s floating around in your head without legs. And there are moments when you come back to it and talk about it and get energized about it but it’s not concrete. So, it’s taking up mental space, and really there are no benefits. It doesn’t necessarily feel good to think about something else you could be doing all the time without an idea of when you’d make it happen. It’s a road trip you’re dreaming about without a plan to start.
With a departure date in mind, your planning becomes more focused and strategic. And this is another benefit of picking that transition date. You begin to work backward, setting milestones and deadlines that are necessary to meet your ultimate goal and that ultimate deadline that you’ve set for yourself. This includes everything from financial planning and network building to maybe acquiring additional skills or resources needed for your new venture.
Most of the women I work with coming out of corporate thrive on deadlines. Well, partly we want to live a life without deadlines, but we also know how to meet a deadline. So, with this departure date, the strategy and focus to meet that deadline becomes so much more real. Maybe you’ve talked to a few people about your business idea. Maybe you don’t even have a business idea. But once you have a departure date set, it’s a catalyst for the rest of the strategic planning.
You’re no longer talking in terms of what ifs, or it would be nice. The conversations shifts to, “Okay, I want to quit this job by November 1st and want to have at least one client by that time. What do I need to do right now in order to create my first paying client?” Knowing that a significant life change is on the horizon can serve as a powerful motivator. It helps you focus your energies on what truly matters, reducing the likelihood of getting sidetracked by the less important tasks or commitments that really don’t align with your future goals.
If you’re leaving your job November 1st, you know that you need to start planting seeds months in advance in order to bear fruit by the winter. If you want to eat that fruit, that’s a powerful motivator to start planting seeds and not get distracted by scrolling or mindless TV. You need to start cultivating towards that fruit and cultivating towards your future goals. Scrolling and other distractions become far less easy when your brain is focused towards that departure date. That’s why it’s so, so important to pick a date. And we’ll talk more about how to pick that date and what to consider, but again, it’s just such an important step.
And if you don’t choose a date, which is likely a glimpse into something you’ve been living for however long. Again, for me it was six years in corporate. There is a risk of stagnation. Without a departure date there is no urgency to push you forward. As a result, it’s easy to remain in a comfortable but unfulfilling routine, telling yourself you’ll make the change some day. Years can pass without significant progress, leaving you with regrets and what ifs.
And this was me, every year at the end of the year review that I talked about. I’d look at my career and it felt like no one thing had changed. Even though I had promotions and team changes and even took advantage of the company’s education benefit to get my MBA. At the end of the year, I still felt like my career was falling short. Another thing that happens is that just like when we have a date, we have more direction and focus, when we don’t have a date, we lack direction and focus. Without a clear deadline, your efforts to prepare for a career transition can be sporadic and disjointed.
Like I said before, you have a conversation here and there, but the puzzle pieces aren’t fitting together. This lack of direction not only wastes valuable time, but also diminishes your chances of success. As you’re likely doing a few random things that feel easy or comfortable and you aren’t putting yourself out there in a way that moves the needle, you’re doing just enough to feel productive and like you’re actually doing it but it’s not leading you to your destination. It’s not getting you anywhere.
It almost pacifies the dream and helps you to feel good in the moment without the results on the other side. You’re planting some seeds, but maybe it’s in the dark and you don’t have a plan to then water them over the next few months. Or maybe you plant the seeds and the next day you forget where you planted them. And this is likely where you’re at now, or some version of this. And we can break this pattern with a simple date marked on the calendar.
Choosing a departure date is more than just a logistical decision. It’s a profound psychological strategy that sets the entire career transition process into motion. It marks the shift from dreaming to doing and aligning your daily actions with your long term vision. So, if you’re serious about changing your life for the better, the first step is simple but so powerful. Mark in that calendar, this isn’t just a date, it’s the starting line of your new life adventure.
So as promised, the next big question is, how do I choose the date? I know that picking a date can seem overwhelming. You don’t want to pick a date that’s too soon. But you really need to leave your job yesterday, so you can’t stand being there too much longer and all the what ifs start to crowd your mind. I get it.
So, let’s break it down by your priorities, whether it’s financial security, aligning with significant life events or ensuring you have enough experience to feel confident. We’ll go through how to balance these factors, to choose a date that feels right without overthinking it, to paralysis. I want to share a little bit about my thought process when I was leaving corporate because it may help you to figure out what factors to think about when picking the date.
My biggest factors were the experience, finances, and family. So let me dig into those a little bit so you can get the juices flowing for what maybe you want your departure date to be. And I don’t want you to get bogged down by this decision. My grandfather always used to say, “You think long, you think wrong.” So do your due diligence and be thoughtful but make this decision by the end of the day. Give yourself a deadline. The faster you can make decisions as an entrepreneur, the more successful you’ll be, I promise. Decision fatigue is real and there are no right answers. I repeat, there are no right answers.
My decision to leave corporate was laborious. I thought about it again for six of the 10 years I was working at my company. I knew I wasn’t doing something that I was truly proud of. I knew my skills and experience were meant for a different career, but I had no idea what to do with that information. And since I never saw myself as an entrepreneur, that felt incredibly scary and risky. But when I finally decided to give it a go and I had hired a career coach that I worked with for a few months leading up to that. I actually based my departure date on a couple of factors that I’d encourage you to think about as well.
So, I officially left my corporate job in July 2021. And at that time, I had about 60 hours of coaching under my belt. So, I knew that coaching was something that energized me. None of those hours were paid actually, they were all donated hours with a housing coalition I partnered with that supported single parents with no or low income. But gaining the direct one-to-one coaching experience was extremely important to me because I wanted to know for sure that this next step was something that energized me. I thought it was since I had worked in mental health and counseling prior to my corporate life, but I didn’t know for sure.
And the last thing I wanted to do was trade one burnout for another. And that’s something we’ll talk a lot about too, is making sure that you are not building a business you hate. So, at 6:00pm every week night after my exhausting day job, I saw clients for an hour or two. And the amazing thing was that I felt more energized than on days that I didn’t have clients. That told me right away that coaching would be different and that it was a good fit.
The next really important factor that I considered was, of course, finances. And I have promised we’ll talk a lot about financial security and how to minimize financial risk in this podcast. But right now, we’re just going to scratch the surface of it. Since I had been thinking about leaving and had many conversations with my partner. We did a lot of math and saved enough money and figured out what could be cut out or shifted in our lives. So that if I didn’t bring in income for a year, we’d be okay.
And that math was super important to me because I didn’t want to have that kind of pressure on me or my business that I had to create a successful practice immediately to support the family financially. So, I sort of had two dates in mind, my transition date and then the date that my business would need to bring in a certain amount of income which would have been July 2022. I could create a savings plan to save a certain amount of money that would give us a year of expenses covered. So that my business didn’t have to be immediately successful, that I didn’t have to replace my income immediately.
The next major factor was that my partner and I were getting married in August of that year. And it was important to me that if I was going to leave my job anyway, then I’d do it before all the wedding festivities so that I could really enjoy that time without being stressed about returning to work. So, my last day was a couple of days before my 32nd birthday. And when I closed my laptop for the last time, I was surrounded by all my favorite girlfriends, because it coincided with my bachelorette weekend, and this was all intentional.
I wanted to be surrounded by my biggest cheerleaders in the moment that my brain would most likely be freaking out. And as you heard, the factors that were important to me and these factors are going to be different for all of us, but financial safety, life events and experience in the role. I wanted to know that we were going to be okay financially if I didn’t immediately bring in an income. I wanted to know that I could truly enjoy and relax during so much time with friends and family at my wedding.
And I had put myself in a position to really understand whether coaching, my next career, the thing I would be transitioning to, energized me. And for you this may not be free work. You may want to work with a client or two on the side or start selling your product before you leave corporate. But for me it was important that I got more client experience under my belt before fully committing to it. I was actually worried that maybe no matter what job I had, I would be resentful and miserable.
After being in that headspace for over a decade, it’s easy to think that there are no other options or maybe it’s me. So, I wanted to make sure that that next step, what I invested so much time and energy in was worthwhile. You may want to consider things like mental health, contract timelines, bonus, or payout schedules. And when I say mental health, I really mean your health and wellbeing.
If staying at a job is taking a toll on your health and wellbeing, it might be better to factor in and create a timeline that’s shorter than say somebody who is not incredibly uncomfortable or burned out at their job, and so they can build a longer runway. Put thought into it, but also like I said, don’t get caught up in picking the ‘right’ or ‘perfect’ date. Just get something down on paper and we’ll figure out the rest.
I recently had a client I started working with who was hell bent or leaving as soon as possible. The burnout at her job was really taking a toll on her and impacting everything in her life, especially her relationship with the kids and her husband. And shortly after we started working together, she found out that her company was acquired and that if she stayed a few more months, her equity would vest, and she’d get a much larger payout. So, she made the decision to stay longer.
This is one of those examples of planning and then life happens. But we can always adjust, which is important to remember. And of course, we worked on all the things within her control to minimize burnout and exhaustion during that time. And I’m excited because next week’s episode is all about how to make work suck less while you’re there. So, tune in next week because I will be giving a ton of strategies to make sure that you make it to that transition date and that work doesn’t continue to suck. Because I promise there are small and big tweaks you can make right now to make that happen just like this client did.
We worked on all the things within her control to minimize burnout and exhaustion while she was still there. And it was perfect because that payout ended up being something that would help her feel more financially secure when leaving her six figure job for the consulting business that she started.
So, what I want you to do is jot down a few factors that are most important to you and answer a couple of questions. And I want you to check the show notes because there is going to be a PDF guide that you can access to help you think through some of these questions and think through what transition date makes the most sense to you. If you are an auditory learner, listening to the podcast is great, but I really want those who maybe are more better at writing down things and learning or need to process in different ways this information.
I’m going to try and provide as much as possible, PDF resources that you can print out or edit on your computer to really allow this information to soak in. It’s another bit of help for you to take action. So, I’m going to go through these questions, but also definitely access those PDF guides. And again, I want you to think about these questions or write it down if you’re not driving. Why is this a priority to consider for the departure date? Remember, we’re thinking about the factors that we want to factor in into our departure date.
Why is this a priority to consider? What is the goal for this priority once I get to my departure date? So, for example, if you want to have a certain amount of money saved, write that number down here. And if you want to have a certain amount of clients, write that down. What is the actual goal? And what will I gain by reaching this goal by my departure date? So, let’s say that you want to consider finances, that is the priority. You want to answer, why are finances a priority to consider for the departure date?
Sometimes we do actually need a runway for expenses. Sometimes we actually do have enough in savings, we just have a lot of mental drama about money. What is the goal for this priority? You’d write down the number like I said. And what will I gain by reaching this goal? Maybe there is being able to maintain your lifestyle. Maybe it’s just feeling less pressure like for me, less pressure for my business to succeed immediately.
So, access the PDF guide. Answer those questions. Reflect on it for all of the priorities or areas that you want to consider. But I really don’t want this activity to hold you back from taking action. Completing that guide, you’ll see that the guide will also ask you to pick a departure date. So, work through these questions, but don’t let it hold you back. Don’t let your brain make this too complicated. Yes, you might want to go and figure out all of your expenses before saying how much you want to save, but if that takes more than five minutes, take a ballpark guess.
You can guess whether your family spends 10K a month or 20K a month. Once you have those priorities set, look at your calendar. I recommend a Google calendar, and go ahead and set an event on the official departure date. If you have that hand held calendar, write it down, put a big X or a star or a fun Lisa Frank sticker on the calendar. Write it down on a post-it and put it on your bedside table or on your bathroom mirror. You want to see this date and be reminded of this date all the time so that you can reap the benefits so that your brain will kick into action.
So, what is the date that you chose? I want to hear from you. You can send me an email at jenna@jenna.coach or feel free to DM me on Instagram or LinkedIn. This is exciting. It should be exciting. And it’s terrifying. If you’re hesitant or feel like you want to throw up, it means you’re doing it right, trust me. You don’t need to know the how right now, that will come. Right now, we’re just taking a small step to tip the domino, to plant the seed, to make one decision right now that will change the way your brain works for the next few months. This is what we need in this moment.
And if you haven’t picked a departure date, now is the time. Again, the how will come with time. I know my audience is intelligent, ambitious, women who are the CEOs of their family. So, I know that you will figure this out. And I will be here every step of the way, giving you the business tips and mindset shifts you need to take the next action but for now, let’s just pick that departure date. Picking the date is enough. Fear, doubt, and anxiety are going to be your constant companions when you think about actually taking the leap.
But I’ll also be a constant companion, talking about strategies to manage these emotions and move forward with them in the vehicle. They are coming on the road trip whether you like it or not, but they will not be driving the vehicle. You are driving the vehicle and I’m in the passenger seat giving you direction, telling you what to watch out for and pointing out all the fun, exciting, beautiful stuff along the way.
Today we have covered not just why you need a departure date, but how to choose it and use it as a springboard for your new life. Remember that the date you set isn’t just the date on the calendar, it’s the beginning of your journey toward a life of greater fulfillment and freedom as a mom and career woman. So now it’s your turn. Set your departure date, write it down, maybe even share it with someone you trust. If you’re feeling bold, share it with me. Please share it with me, even if you’re feeling scared. I’d love to be here to cheer you on.
And if you’re looking for more support, check out my free mom entrepreneur circle that meets monthly. I will make sure to put the link to sign up in the show notes. This is a safe space where you can share your departure date and be cheered on by other women going through the same life transition. And stay tuned for next week. We’ll be talking about how to make work suck less while you’re there, which I mentioned earlier. Chances are your departure date isn’t tomorrow, which means you’ll be showing up to a soul crushing job each day, and truthfully, it doesn’t have to be soul crushing in the meantime.
There are exciting changes on the horizon, and I want you to enjoy every minute of it. And no, it doesn’t mean that your boss or the job itself will change. It means that you’re going to change a little bit in order to be in a better headspace to make all these entrepreneurial decisions coming up.
So, goodbye for now. I think I made it. I think the household is still asleep. So, take care of yourself today. And if no one has told you today, you’re doing a great job.
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.
Welcome to How to Quit Your Job: A Mom’s Guide to Creating a Life and Business You Love. It’s a podcast that helps working moms just like you, optimize your time, manage your mind, and start a business that helps you create more freedom, flexibility, and, yes, fun. I’m business and mindset coach Jenna Rykiel. And I offer practical tips to help you ditch the nine-to-five. I have been exactly where you are, and I know what it takes to make the transition without trading one form of burnout for another. So let’s get started.
Hello, good morning and good afternoon or good evening wherever you are today. It is morning where I am. I am trying to record this episode before my household wakes up. And my household right now is my parents, my husband, and my son. My husband and I are getting construction done on our house so we’re actually living with my parents in their quaint little rancher. And as soon as everyone wakes up, there will be so much noise. So, I am trying to get this podcast recorded for you before that happens. So, it is early, and I am sorry if I sound tired. I’m not as tired as I might sound. So, let’s go.
If you’re listening today, I know you’re someone who’s been thinking about making a change but maybe you’re stuck on how to start. You’ve got dreams, but turning them into reality feels daunting so let’s change that.
In today’s episode, we’re talking about a little thing called planning and not meal planning or vacation planning, but I’m sure you’re doing all those things, too. We’re talking about planning your transition date, the date when you’re going to be leaving your company to finally work on your own terms. Every few episodes I’m going to give you tangible tools to create and execute a plan so that you can make these hopes and dreams turn into a true reality and this is one of those episodes.
When I think about what my clients are missing or what they really believe is holding them back from creating a life and really career they love, not having a plan is one of the biggest obstacles. So, as promised, we’re going to solve that little by little on this podcast, and especially in this episode. I’m going to provide you with tangible and actionable bite sized steps that keep you moving forward in a way that feels manageable with all the other things you have going on.
One thing I preach constantly in my program is that meaningful action, which is defined by small consistent steps, is what leads to big changes over time. It’s not about massive action steps or giant leaps. Those things are scary and often create a situation where we actually avoid taking action altogether. I want you to start with meaningful action. So small steps that are a little uncomfortable, a little scary, but that allow you to work a new muscle, a taking action muscle.
So today I’m going to encourage you and give you the tools to take a meaningful action step that has to do with planning your departure date. And if you know my work at all or follow me on any social media, you’ll know that I talk about the importance of planning all the time. It’s another pillar of my coaching program because if it doesn’t get planned it doesn’t get done. And especially if it doesn’t get on the calendar, it doesn’t get done. And planning isn’t just for organized people or type A folks. It’s important for all of us who want to live a conscious and deliberate life.
And there are tools and systems that make planning and sticking to plans more doable. Planning is even more critical for moms like you because you’ve got a lot going on, but you’ve also got a lot of big dreams that aren’t going to achieve themselves. You have a dream of leaving your nine to five job behind and starting your own business. And the reality is that if it doesn’t get planned, it doesn’t get done. How many years have you been thinking about this?
I know for me, I’ve shared before it was about six years. Six years that I had this idea to start my own business because I had all the education. I had my coaching certification. I had a master’s in counseling. I earned my MBA. But every year, at the end of the year when my husband and I would sit down and do our New Year’s reflection, career would get a low rank. And I’d write something like, I’m capable of more or I’m not doing anything meaningful. Who can relate?
The years keep going by and we look back and nothing has gotten done or very little has gotten done to move the needle. And I don’t want you to be like Jenna then. I want you to be like Jenna now who has a wildly different way of thinking about herself and business with so many more tools to be able to consciously plan and take action. I want you to be in the business of getting things done, not just in your nine to five, not just at home, not just for the kids, not just for your partner. I want you to be in the business of getting things done that will radically change the trajectory of your life so that you’re living on your own terms and calling the shots.
So, like I said, we’re going to do that in tangible bite sized steps which are far less scary. We’re going to build a muscle. You need to take action because it’s a muscle and as you work it, it grows, taking action gets easier. Everything is a muscle that either grows or deteriorates. And I want you to be in the business of growing, not deteriorating. And a lot of you listening right now may feel like you’re deteriorating. I know I felt like that most days waking up and signing into a job that felt like it was holding me back from being the best version of myself.
And in this episode, we’re just taking our first bite of planning. And it’s an incredibly important element in the big picture of planning for your business. It’s going to be quick and trust me, there’s going to be a lot of mental drama. But when this one tangible item is planned and crossed off the to-do list, you’re going to be on your way to becoming your own boss.
So, let’s talk about deciding your departure date from corporate life. It should be easy enough. Maybe, maybe not. And if you’re sitting there and you’re like, “Boom, I’ve got my date, we’re good to go,” Or, “I left corporate a few months ago.” Then, kudos to you. You picked a date and made it happen. I encourage you to keep listening, because this doesn’t just have to apply to leaving your job. It can also be when you launch your first program or a date that you move to a different city.
Any big transition date in our life and our business we can sometimes delay making it happen because we haven’t been clear about the date of when it needs to happen. We’ll talk a lot more about why picking a date is so essential, but planning and picking that departure date gives you direction and clarity.
Let’s imagine you’re on a road trip and you have no idea when you’ll get to the destination. You’re just driving and driving and driving, I’ve driven across country a lot and I would never get in that car unless I knew the date that we’d be arriving. If you’re just driving with no timeline to consider, you’re aimlessly driving and you lose all purpose, you get antsy, anxious, and truly tired of being in the car. This is so many of you at your jobs right now, you’re antsy, anxious, and tired of being in your role.
You’re aimlessly showing up each day and not feeling good about it. I live in Maryland now. My husband and I moved back to where we’re from, to be close to family when my son Adley was born. But we lived in Denver for six years prior to that. And at least twice a year made the 26 hour drive because we were loving dog parents and our dog, Bubba, needed to be home with us, of course for all holidays and visits. So, we did that drive a lot. Never once did we get in that car without having a clear idea of when we wanted to be at our destination.
We planned our trip based on what day we needed to get back home. That informed so much about the trip. We could then plan where we would stay overnight and book the Airbnb. We had an idea of, if we left a day earlier, could we stay a day longer with a friend who was living in Dayton? You get the point. In order for the trip to be a success, we need to plan and that plan really starts with knowing when we get to our destination. It’s absolutely essential. And this isn’t always easy because there are a lot of factors involved.
And we will talk about all of those factors in just a couple of minutes. But our brain loves that clarity. And just to go off on another analogy tangent, just because you plan the arrival date, doesn’t mean the trip goes exactly as planned. We’ll talk about this at length on the podcast, the unexpected nature of kids and life because we all know that life with kids is unpredictable and that can present some obstacles for us in this venture.
My husband and I chose the date that we would be arriving. You can plan all the things in your trip, and then your van can have a belt blow in Park, Kansas. And if it’s a Sunday, you definitely aren’t getting that belt fixed. And so, you would absolutely need to be towed over four hours with your dog to get back to Denver. So yes, just because you have a plan doesn’t mean everything runs smoothly but it’s so much better to have a plan to work off of for that road trip than to just drive aimlessly, especially if kids are in the car.
And when it comes to quitting your job, planning starts with deciding your transition date. It’s the first step towards turning your dreams into reality. It’s knowing what day you want to get to that destination that you’ve been thinking about for however many years. The destination that allows you to wake up each day feeling like you’re doing work that’s meaningful and that you have control over your time.
So, let’s talk about and understand really the power of picking a departure date. It seems like such a small detail, but it’s so powerful. You’ve been at your job, comfortable, yet unfulfilled, always thinking about what could be. Like many, you might feel trapped in this endless cycle of some day. Setting a departure date, transforms that someday into a concrete plan. It’s about marking a day on your calendar that boldly states, this is when my new life starts. It’s not just about leaving a job, it’s about embracing a future that you control.
So, choosing a departure date might seem like a small administrative step in the grand scheme of leaving your job and starting your own business. However, it’s much more than just marking a day on your calendar. It’s about setting a powerful intention that can fundamentally change your approach, mindset, and actions. I want to sell you on this, not just why it’s so crucial, but also what could happen if you don’t set one and the transformative effect it can have once you do.
By the end of this episode, I want you to feel energized to take this one small, yet meaningful step, it’s like tipping the first domino. Let’s revisit why setting the date is so important, it creates a sense of urgency and commitment. Setting a departure date shifts your goals from the abstract, I want to start a business someday to the concrete, I’m starting a business on this specific date. This commitment creates a sense of urgency, which compels you to take action rather than allowing your ambitions to remain in this realm of daydreams.
Without a departure date on the calendar, it’s a daydream, one that takes up a lot of energy because it’s floating around in your head without legs. And there are moments when you come back to it and talk about it and get energized about it but it’s not concrete. So, it’s taking up mental space, and really there are no benefits. It doesn’t necessarily feel good to think about something else you could be doing all the time without an idea of when you’d make it happen. It’s a road trip you’re dreaming about without a plan to start.
With a departure date in mind, your planning becomes more focused and strategic. And this is another benefit of picking that transition date. You begin to work backward, setting milestones and deadlines that are necessary to meet your ultimate goal and that ultimate deadline that you’ve set for yourself. This includes everything from financial planning and network building to maybe acquiring additional skills or resources needed for your new venture.
Most of the women I work with coming out of corporate thrive on deadlines. Well, partly we want to live a life without deadlines, but we also know how to meet a deadline. So, with this departure date, the strategy and focus to meet that deadline becomes so much more real. Maybe you’ve talked to a few people about your business idea. Maybe you don’t even have a business idea. But once you have a departure date set, it’s a catalyst for the rest of the strategic planning.
You’re no longer talking in terms of what ifs, or it would be nice. The conversations shifts to, “Okay, I want to quit this job by November 1st and want to have at least one client by that time. What do I need to do right now in order to create my first paying client?” Knowing that a significant life change is on the horizon can serve as a powerful motivator. It helps you focus your energies on what truly matters, reducing the likelihood of getting sidetracked by the less important tasks or commitments that really don’t align with your future goals.
If you’re leaving your job November 1st, you know that you need to start planting seeds months in advance in order to bear fruit by the winter. If you want to eat that fruit, that’s a powerful motivator to start planting seeds and not get distracted by scrolling or mindless TV. You need to start cultivating towards that fruit and cultivating towards your future goals. Scrolling and other distractions become far less easy when your brain is focused towards that departure date. That’s why it’s so, so important to pick a date. And we’ll talk more about how to pick that date and what to consider, but again, it’s just such an important step.
And if you don’t choose a date, which is likely a glimpse into something you’ve been living for however long. Again, for me it was six years in corporate. There is a risk of stagnation. Without a departure date there is no urgency to push you forward. As a result, it’s easy to remain in a comfortable but unfulfilling routine, telling yourself you’ll make the change some day. Years can pass without significant progress, leaving you with regrets and what ifs.
And this was me, every year at the end of the year review that I talked about. I’d look at my career and it felt like no one thing had changed. Even though I had promotions and team changes and even took advantage of the company’s education benefit to get my MBA. At the end of the year, I still felt like my career was falling short. Another thing that happens is that just like when we have a date, we have more direction and focus, when we don’t have a date, we lack direction and focus. Without a clear deadline, your efforts to prepare for a career transition can be sporadic and disjointed.
Like I said before, you have a conversation here and there, but the puzzle pieces aren’t fitting together. This lack of direction not only wastes valuable time, but also diminishes your chances of success. As you’re likely doing a few random things that feel easy or comfortable and you aren’t putting yourself out there in a way that moves the needle, you’re doing just enough to feel productive and like you’re actually doing it but it’s not leading you to your destination. It’s not getting you anywhere.
It almost pacifies the dream and helps you to feel good in the moment without the results on the other side. You’re planting some seeds, but maybe it’s in the dark and you don’t have a plan to then water them over the next few months. Or maybe you plant the seeds and the next day you forget where you planted them. And this is likely where you’re at now, or some version of this. And we can break this pattern with a simple date marked on the calendar.
Choosing a departure date is more than just a logistical decision. It’s a profound psychological strategy that sets the entire career transition process into motion. It marks the shift from dreaming to doing and aligning your daily actions with your long term vision. So, if you’re serious about changing your life for the better, the first step is simple but so powerful. Mark in that calendar, this isn’t just a date, it’s the starting line of your new life adventure.
So as promised, the next big question is, how do I choose the date? I know that picking a date can seem overwhelming. You don’t want to pick a date that’s too soon. But you really need to leave your job yesterday, so you can’t stand being there too much longer and all the what ifs start to crowd your mind. I get it.
So, let’s break it down by your priorities, whether it’s financial security, aligning with significant life events or ensuring you have enough experience to feel confident. We’ll go through how to balance these factors, to choose a date that feels right without overthinking it, to paralysis. I want to share a little bit about my thought process when I was leaving corporate because it may help you to figure out what factors to think about when picking the date.
My biggest factors were the experience, finances, and family. So let me dig into those a little bit so you can get the juices flowing for what maybe you want your departure date to be. And I don’t want you to get bogged down by this decision. My grandfather always used to say, “You think long, you think wrong.” So do your due diligence and be thoughtful but make this decision by the end of the day. Give yourself a deadline. The faster you can make decisions as an entrepreneur, the more successful you’ll be, I promise. Decision fatigue is real and there are no right answers. I repeat, there are no right answers.
My decision to leave corporate was laborious. I thought about it again for six of the 10 years I was working at my company. I knew I wasn’t doing something that I was truly proud of. I knew my skills and experience were meant for a different career, but I had no idea what to do with that information. And since I never saw myself as an entrepreneur, that felt incredibly scary and risky. But when I finally decided to give it a go and I had hired a career coach that I worked with for a few months leading up to that. I actually based my departure date on a couple of factors that I’d encourage you to think about as well.
So, I officially left my corporate job in July 2021. And at that time, I had about 60 hours of coaching under my belt. So, I knew that coaching was something that energized me. None of those hours were paid actually, they were all donated hours with a housing coalition I partnered with that supported single parents with no or low income. But gaining the direct one-to-one coaching experience was extremely important to me because I wanted to know for sure that this next step was something that energized me. I thought it was since I had worked in mental health and counseling prior to my corporate life, but I didn’t know for sure.
And the last thing I wanted to do was trade one burnout for another. And that’s something we’ll talk a lot about too, is making sure that you are not building a business you hate. So, at 6:00pm every week night after my exhausting day job, I saw clients for an hour or two. And the amazing thing was that I felt more energized than on days that I didn’t have clients. That told me right away that coaching would be different and that it was a good fit.
The next really important factor that I considered was, of course, finances. And I have promised we’ll talk a lot about financial security and how to minimize financial risk in this podcast. But right now, we’re just going to scratch the surface of it. Since I had been thinking about leaving and had many conversations with my partner. We did a lot of math and saved enough money and figured out what could be cut out or shifted in our lives. So that if I didn’t bring in income for a year, we’d be okay.
And that math was super important to me because I didn’t want to have that kind of pressure on me or my business that I had to create a successful practice immediately to support the family financially. So, I sort of had two dates in mind, my transition date and then the date that my business would need to bring in a certain amount of income which would have been July 2022. I could create a savings plan to save a certain amount of money that would give us a year of expenses covered. So that my business didn’t have to be immediately successful, that I didn’t have to replace my income immediately.
The next major factor was that my partner and I were getting married in August of that year. And it was important to me that if I was going to leave my job anyway, then I’d do it before all the wedding festivities so that I could really enjoy that time without being stressed about returning to work. So, my last day was a couple of days before my 32nd birthday. And when I closed my laptop for the last time, I was surrounded by all my favorite girlfriends, because it coincided with my bachelorette weekend, and this was all intentional.
I wanted to be surrounded by my biggest cheerleaders in the moment that my brain would most likely be freaking out. And as you heard, the factors that were important to me and these factors are going to be different for all of us, but financial safety, life events and experience in the role. I wanted to know that we were going to be okay financially if I didn’t immediately bring in an income. I wanted to know that I could truly enjoy and relax during so much time with friends and family at my wedding.
And I had put myself in a position to really understand whether coaching, my next career, the thing I would be transitioning to, energized me. And for you this may not be free work. You may want to work with a client or two on the side or start selling your product before you leave corporate. But for me it was important that I got more client experience under my belt before fully committing to it. I was actually worried that maybe no matter what job I had, I would be resentful and miserable.
After being in that headspace for over a decade, it’s easy to think that there are no other options or maybe it’s me. So, I wanted to make sure that that next step, what I invested so much time and energy in was worthwhile. You may want to consider things like mental health, contract timelines, bonus, or payout schedules. And when I say mental health, I really mean your health and wellbeing.
If staying at a job is taking a toll on your health and wellbeing, it might be better to factor in and create a timeline that’s shorter than say somebody who is not incredibly uncomfortable or burned out at their job, and so they can build a longer runway. Put thought into it, but also like I said, don’t get caught up in picking the ‘right’ or ‘perfect’ date. Just get something down on paper and we’ll figure out the rest.
I recently had a client I started working with who was hell bent or leaving as soon as possible. The burnout at her job was really taking a toll on her and impacting everything in her life, especially her relationship with the kids and her husband. And shortly after we started working together, she found out that her company was acquired and that if she stayed a few more months, her equity would vest, and she’d get a much larger payout. So, she made the decision to stay longer.
This is one of those examples of planning and then life happens. But we can always adjust, which is important to remember. And of course, we worked on all the things within her control to minimize burnout and exhaustion during that time. And I’m excited because next week’s episode is all about how to make work suck less while you’re there. So, tune in next week because I will be giving a ton of strategies to make sure that you make it to that transition date and that work doesn’t continue to suck. Because I promise there are small and big tweaks you can make right now to make that happen just like this client did.
We worked on all the things within her control to minimize burnout and exhaustion while she was still there. And it was perfect because that payout ended up being something that would help her feel more financially secure when leaving her six figure job for the consulting business that she started.
So, what I want you to do is jot down a few factors that are most important to you and answer a couple of questions. And I want you to check the show notes because there is going to be a PDF guide that you can access to help you think through some of these questions and think through what transition date makes the most sense to you. If you are an auditory learner, listening to the podcast is great, but I really want those who maybe are more better at writing down things and learning or need to process in different ways this information.
I’m going to try and provide as much as possible, PDF resources that you can print out or edit on your computer to really allow this information to soak in. It’s another bit of help for you to take action. So, I’m going to go through these questions, but also definitely access those PDF guides. And again, I want you to think about these questions or write it down if you’re not driving. Why is this a priority to consider for the departure date? Remember, we’re thinking about the factors that we want to factor in into our departure date.
Why is this a priority to consider? What is the goal for this priority once I get to my departure date? So, for example, if you want to have a certain amount of money saved, write that number down here. And if you want to have a certain amount of clients, write that down. What is the actual goal? And what will I gain by reaching this goal by my departure date? So, let’s say that you want to consider finances, that is the priority. You want to answer, why are finances a priority to consider for the departure date?
Sometimes we do actually need a runway for expenses. Sometimes we actually do have enough in savings, we just have a lot of mental drama about money. What is the goal for this priority? You’d write down the number like I said. And what will I gain by reaching this goal? Maybe there is being able to maintain your lifestyle. Maybe it’s just feeling less pressure like for me, less pressure for my business to succeed immediately.
So, access the PDF guide. Answer those questions. Reflect on it for all of the priorities or areas that you want to consider. But I really don’t want this activity to hold you back from taking action. Completing that guide, you’ll see that the guide will also ask you to pick a departure date. So, work through these questions, but don’t let it hold you back. Don’t let your brain make this too complicated. Yes, you might want to go and figure out all of your expenses before saying how much you want to save, but if that takes more than five minutes, take a ballpark guess.
You can guess whether your family spends 10K a month or 20K a month. Once you have those priorities set, look at your calendar. I recommend a Google calendar, and go ahead and set an event on the official departure date. If you have that hand held calendar, write it down, put a big X or a star or a fun Lisa Frank sticker on the calendar. Write it down on a post-it and put it on your bedside table or on your bathroom mirror. You want to see this date and be reminded of this date all the time so that you can reap the benefits so that your brain will kick into action.
So, what is the date that you chose? I want to hear from you. You can send me an email at jenna@jenna.coach or feel free to DM me on Instagram or LinkedIn. This is exciting. It should be exciting. And it’s terrifying. If you’re hesitant or feel like you want to throw up, it means you’re doing it right, trust me. You don’t need to know the how right now, that will come. Right now, we’re just taking a small step to tip the domino, to plant the seed, to make one decision right now that will change the way your brain works for the next few months. This is what we need in this moment.
And if you haven’t picked a departure date, now is the time. Again, the how will come with time. I know my audience is intelligent, ambitious, women who are the CEOs of their family. So, I know that you will figure this out. And I will be here every step of the way, giving you the business tips and mindset shifts you need to take the next action but for now, let’s just pick that departure date. Picking the date is enough. Fear, doubt, and anxiety are going to be your constant companions when you think about actually taking the leap.
But I’ll also be a constant companion, talking about strategies to manage these emotions and move forward with them in the vehicle. They are coming on the road trip whether you like it or not, but they will not be driving the vehicle. You are driving the vehicle and I’m in the passenger seat giving you direction, telling you what to watch out for and pointing out all the fun, exciting, beautiful stuff along the way.
Today we have covered not just why you need a departure date, but how to choose it and use it as a springboard for your new life. Remember that the date you set isn’t just the date on the calendar, it’s the beginning of your journey toward a life of greater fulfillment and freedom as a mom and career woman. So now it’s your turn. Set your departure date, write it down, maybe even share it with someone you trust. If you’re feeling bold, share it with me. Please share it with me, even if you’re feeling scared. I’d love to be here to cheer you on.
And if you’re looking for more support, check out my free mom entrepreneur circle that meets monthly. I will make sure to put the link to sign up in the show notes. This is a safe space where you can share your departure date and be cheered on by other women going through the same life transition. And stay tuned for next week. We’ll be talking about how to make work suck less while you’re there, which I mentioned earlier. Chances are your departure date isn’t tomorrow, which means you’ll be showing up to a soul crushing job each day, and truthfully, it doesn’t have to be soul crushing in the meantime.
There are exciting changes on the horizon, and I want you to enjoy every minute of it. And no, it doesn’t mean that your boss or the job itself will change. It means that you’re going to change a little bit in order to be in a better headspace to make all these entrepreneurial decisions coming up.
So, goodbye for now. I think I made it. I think the household is still asleep. So, take care of yourself today. And if no one has told you today, you’re doing a great job.
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.
Enjoy the Show?
Don’t miss an episode, follow the podcast on Spotify, Apple Podcasts, or RSS.
