Ready to Quit Your Job? Here’s How I Knew It Was Time.

  Sam Vander Wielen: So you’re about to walk into your nine-to-five, or you just piled into the car after work, and you’re wondering, “How much longer do I have to do this for?” You daydream at work about being outside of these four walls, doing things you love, spending more time with your family, and finally taking action on the things you say you want to do with your life.

That little side hustle that you started, well, you’re starting to wonder what it would look like for it to be your full-time job. The problem is you don’t know when to leave your job. Do you build the business first and then take the leap? Do you leap and then take all that time that you have on your hands now to build a successful business?

How do you know when it’s the right time to actually leave your job? How do you know if it’s a good idea to even leave your job, or if you’re just fed up?

Nobody seems to be able to give you the perfect answer or timeline. But today, I’ll share how I knew it was time for me to leave my corporate law career to start an online health coaching business, the business I had before my legal templates one, what I got wrong, and what I’d have in place before you ever give notice

And hey there, welcome back to On Your Terms® or welcome if you’re new here. I’m so glad you’re here. On Your Terms® is a podcast for online business owners who want to be as present in their lives, as profitable in their businesses. And I can’t think of a greater reason to be more present in your life than actually leaving your job so that you can be more present in your life. That’s one of the greatest gifts that I think leaving my job has given me, and you might be listening to this hoping for the same thing in the future.

Now, before I hop into how I left my job and all the things that I did and all the things I’ve now told thousands of people to do if they are thinking about leaving their job, I have to tell you that next Monday, October 19th, I’m hosting my last live legal class of the entire year.

It’s called How to Legally Start an Online Business Before 2026 Ends, and in it, I’m going to teach you everything that you need to know about how to actually start an online business the right way so you don’t accidentally make any mistakes. But I’m also going to keep you all updated on everything that’s going on in the online space, because in case you haven’t heard, there’s a lot going on this year between AI changes and AI laws that are coming for our industry.

We also have, our personal privacy concerns, and a lot of the different changes on the apps this year have not helped us with those. And of course, we have the continuing ADA lawsuit trend that’s hitting small business owners everywhere. So I’m gonna give everybody a little, like, state of the union update and also some very, very easy ways that you can handle all of those things in addition to actually starting your online business.

So go ahead and click the link in the show notes to sign up now. It’s completely free. It’s next Monday, October 19th at 3:00 PM Eastern. If you can’t make it live, sign up to get the replay. It’s the only way to get the replay. I’ll even send it to you by both audio and video so you have both options there.

But go ahead and click the link now in the show notes to sign up for this free legal workshop because it fills super fast.

So for those of you who don’t know, I used to be a corporate lawyer. That’s how I started out my career, and I pretty much hated my life as a corporate lawyer from day one. I spent most of my time working in law firms that had anywhere from thousands of lawyers, then to hundreds of lawyers, up in a skyscraper in the city of Philadelphia, my, my place of birth, mostly just staring out the window.

My very first office that I had as a lawyer was so high up that we were above the clouds, which was super cool on most days, except post-Hurricane Sandy, when you could actually feel the building moving. And everybody kept telling me, “That’s normal. Don’t worry, it’s supposed to do that.” And that does not help when you’re on the, like, 60-something floor of a building and it’s moving.

But I spent most of my time up there, honestly, staring out the window, wondering what it would be like to be out of there, and really thinking that would be an option for everybody else, but not for me. I didn’t really see a pathway out. So for those first few years as a corporate lawyer, I kinda just kept my head down.

I worked. I was super miserable. And I would complain to absolutely anyone who would listen, anywhere from, like, my cab driver, to my husband, to my friends, um, to obviously the other people at work who were mostly equally as miserable. And I really didn’t see it as like, “Oh, I wanna do something about this.” Uh, it was more just a, “I can’t believe I’m in this terrible situation. I hate it.” And I didn’t see any other option.

Luckily around that time in the kinda mid-2010s was also when blogging had gotten so popular, health coaching and just coaching in general had kinda like come onto the scene and become more mainstream, where it was starting to even reach people, little people like me who were working at law firms.

And I was just very intrigued by like, what are all these things? What’s going on online? And I spent a lot of those early days just kind of consuming and getting to know what was all going on. I think it’s really important for you to see the possibility of what’s, you know, what’s possible for you, and like seeing examples of people who have come before you, and be like, “I didn’t even know that was a business that you could run.”

Or maybe you find someone who used to be in your exact career. Like, I found my friend Simi Botic, who was a lawyer who had left, and I was just like, “Wait, there’s another lawyer out there who like left, and she’s still standing, and she didn’t die, and nothing terrible happened. Like, actually she seems like she’s thriving and she’s doing better.”

Like, my mind was just blown by this idea. So I think it’s really, really important to … Everybody kinda goes through that period and has that aha moment that there’s something else out there for them.

I spent a lot of my time as a lawyer as we went on, you know, starting baby steps. Uh, if you’ve read my book, uh, called When I Start My Business I’ll Be Happy, I talk about how, like, first I started a food blog and so, like, I did that on the side while I worked as a lawyer, which then led me to say, “Hey, maybe I start this, like, health coaching thing on the side.” Still my idea was that this was always going to be on the side. Like, it wasn’t leaving the law to do this. It was something in addition.

So I start this health coaching business on the side, and I take a certification program, and I start going to events in person and meeting people who I had only known on Instagram.

And it really started to intrigue me that maybe, in fact, I could leave being a lawyer and do this. But I really didn’t know, like, when is the time, right? Like, when do I actually leave?

I didn’t see any sort of pathway where I was going to be able to, like, build up a health coaching business to be s- as successful or, like, make me enough money as I was making as a lawyer, because it was kind of like counterproductive because I was working so much as a lawyer that then I couldn’t work enough in my business. And so it was like, “Oh, if I had more time to spend on this business…” I bet you that you have had this thought too, because a lot of people tell me this, and I, I see this in my DMs and stuff a lot, where people will be like, “If I just had more time to work on my business, I think I actually could make it successful. But I, like, kinda wanna know it’s successful before I leave my stable job.” So it was like a very… I just felt like I was really stuck in this place.

And I realized then that there are really two categories of things to consider when you are thinking about leaving your job. There’s the logistical one, there’s the financial one, right? Where you have to be financially smart about it. I don’t know that it’s always the best advice that people give of just like, “Take the leap,” and like, “It’ll happen for you,” or like, “Fake it till you make it and then it’ll happen.”

I don’t think that’s very financially responsible. I also think that’s just kinda ignorant advice sometimes, that some people don’t have that situation in their life where they can afford to do that. So it’s like, it, it just might not be your situation. So there’s this logistical, financial consideration.

I also think there’s more of like an emotional component. There’s more of the s- part of like making sure that we’re not, you know, there’s a reason I titled my book When I Start My Business I’ll Be Happy. I think a lot about arrival fallacy, as they call it. And so like, you know, I certainly was the type of person who was like, “When I stop being a lawyer, my life’s gonna be amazing.”

You know? That’s why, that’s why it’s literally the title of the book, ’cause I thought leaving my job and all the shit that came along with that job, and I blamed everything on the job, and the bosses, and the hours, and the type of work, and adversaries, and all that, that as soon as I just removed all that and cut it out, e- everything would be great, right?

And obviously that’s not the case, so today I really wanted to talk with you about, yeah, let’s talk through the logistical steps of like what are some things that you can do to get prepared? What are some of my best recommendations, um, in order to get prepared to potentially leave your job? I think there’s some things you should absolutely do or not do before you go.

And then let’s talk a little bit about like how do we also start preparing for some of the emotional sides of it? How do we, how do we think through like are we just pissed off at our job? Do you just need a different job at a different company? Or is a business actually the, you know, answer to what you’re feeling right now?

Because to me, looking back on it, I would tell you that being miserable at your job isn’t a sign that you’re ready to leave it or that you’re ready to start a business. It’s a sign to start getting ready. So I think today, a lot of today is gonna be spent talking about getting things ready, kind of preparing. Like preparing as if we’re gonna move, right? That’s how I want you to think about it. It’s like you’re moving jobs or you- but in this case, you might be moving from a job to a business.

So let’s kick things off talking about the logistical steps, more of the financial steps, and how you can get financially prepared to either think about or actually leave your nine-to-five.

Now, the very first thing is that we have to talk about financial security. I do not want you leaving your job and having a business that’s, like, a little, itty-bitty baby business that is now responsible for financially supporting you. I think one of the biggest mistakes that I see new business owners make is that they leave their jobs or they go to start a business, and then they, immediately, like, you know, they’re in my DMs, like, three to six months later being like, “This thing isn’t making enough money to pay for my whole life.

Like, I’m so frustrated,” right? . So I don’t think it’s healthy for you or your business to have such immense financial pressure on it so early on.

And so because of that, that being kind of my, I guess, mindset and my approach to how I prepared to leave my nine-to-five, I want to make sure that you have financial security.

The very first thing I would encourage you to do is to take a look at what your personal expenses are. Do you know, either offhand or quickly looking at some spreadsheet or something, do you know how much it costs you to live, like, every single month or even on an annual basis? ‘Cause you wanna factor in those annual expenses that you have.

Now some of you might be listening and you might be like, “Well, I’ve done really great so far and I’m a good saver, and I can live without my business producing income for me for a year or six months or whatever.” And if that’s the case, congratulations. If that’s not the case, though, I want you to look at what it costs you to live and think about how you can beef up your savings to actually cover those personal expenses, I would say for at least six months.

Obviously, as, as far past six months as you can go, the better. You’re gonna give yourself more and more runway. But I think that that’s a, a healthy and a realistic runway to give you so that when you leave, you have six months of being a full-time business owner to go hog wild trying to, trying to build that business and get all these new people in and let yourself actually focus on your business because you know that you’ve got the personal expenses covered.

Now my hope for you would be that when you do leave and you have your business and you’re focusing all your time and attention on it, that the business is starting to generate money. But I think the key, and what was key for me, was that I didn’t pull out money very early on. I took that money and I kept putting it back into the business.

I invested in getting some branding done and then, you know, after having built out my first website myself, I went out and I found Ansley, who still works for me. And, uh, so I found her in 2016 and paid Ansley a couple thousand dollars and said, “Hey, can you make this website that I made myself just, like, look a little bit better?

And also, I can’t figure out how to make certain things happen.” So y- I put the money back into the business and did some of these things that I couldn’t do myself.

I talk a lot in my book about how once, once your business starts making money, that the way that I like to look at it is like, how much can I pull out consistently and pay myself for the next three months? So if you had $1,500, for example, extra that you could pull out and pay yourself, instead of paying yourself $1,500 this month, but then not knowing whether in months two and three you could pay yourself at all, I would rather pay myself $500, $500, $500 over the course of three months and get myself used to consistently paying myself.

I started my business bank account with $100 in cash. And so my first month, I made, uh, almost $5,000 in the business, and so I just put it, boop, right into the account. The next month, I think I made about the same. And I just kept it going until I said, “Okay, I think this is a thing, so I’m gonna start paying myself.”

I literally started paying myself $500. Um, and obviously, that is not enough to live off of, but I was only able to do that because I had prepared. I had done the financial security steps of figuring out, what are my personal expenses? How much do I need to live? So I just started getting used to paying myself a little bit over time, and then obviously up- upped it.

Now, once we know our personal expenses and what it actually costs you to live each month so that you’re not relying on your business for it, at least at first, we also wanna take a look at our emergency savings because even if we can just pay our month-to-month bills, we wanna make sure that if anything happens, the hot water heater goes, the tires on your car blow, like something happens, a, a dentist thing, we wanna make sure we can pay for that.

Now, one of the biggest elephants in the room, unfortunately, being in America, is that we have to talk about benefits and healthcare coverage. So I have always been upfront about this to say that I was very lucky in this, in the fact that when I wanted to leave the law, I had just gotten married, so I had not only a partner where I could also rely on his income a little bit.

But to be clear, we very much needed my income. Like, my income was half of what we were paying for everything, so it… we couldn’t live off of him. It’s just that he could float me for a bit. But, but he did have all the benefits, right? So he had benefits through his, job, and so I was able to have health insurance and maintain all of that.

Obviously, an immense, immense privilege that not everyone has, and if I could be president for the day, I- it would be the first thing I would do, would be to stop tying our healthcare, uh, to our jobs so that people could go out and actually do these things and, and so that we could spark more entrepreneurship and innovation in this country.

But that’s neither here nor there. Unfortunately, we don’t have that. There are options that, are available to people who go self-employed. Obviously, there’s also COBRA, but it’s immensely, uh, expensive. You can always look at the marketplace for health insurance, just to start getting a, um, an idea of exactly how much this is going to cost.

Because I think one of the things people don’t think about, and I wrote about this a lot in the book, was like, there are, there are both expenses that go away when you don’t work in a nine-to-five anymore, and then there are expenses that come in. So an expense that would come in, an example might be something related to your benefits.

For me, expenses that went away were all of the lunches I used to go out to and all of the shopping I used to do because I was so miserable. And because I was making money and really hated my job, I would just spend it. I didn’t really care. Once I had a business, I felt much more like, I don’t know, this is what I wanna do.

So like, oh, it’s worth it for me to not buy more stuff I don’t need because I really want it to go to the business. So in a way, I saved more money being an entrepreneur, but then there were also these additional expenses, or there are additional expenses for people who leave.

Now the next step to, I think, kinda locking down this financial security before you leave your nine to five is looking at what we can sell, what we can cut back on, and obviously what we can save. So I, I know it sounds cheesy and people… I remember somebody making a comment one time of like, “Oh, let me guess. Are you gonna tell me to sell the stuff in my basement?” I’m like, “Actually, yeah,” because I think it generated a few hundred dollars when I started, my health coaching business to sell some things that were in my basement.

And to be honest with you, a couple hundred dollars gets you a domain name, it registers your LLC, and it could make your first, payment for business insurance. So that’s pretty darn good.

With that, you’re kinda well on your way to literally actually starting a business. But if the stuff is just, like, sitting in your basement or you’ve got a piece of furniture you’ve been meaning to sell for a while or clothes that you could get rid of or anything else, I mean, for me, I also got rid of a lot of attorney clothes, and that was something.

So, like, there was … It actually added up, so I, I wouldn’t look over it.

Again, knowing that I was so motivated to leave, a lot of what I did was actually just cut back, just saying like, “Hey, I don’t need to go out so much. I don’t need to, do so much online shopping.” Like, there was just a lot of things I was willing to give up.

I sold my fancy car that I only bought ’cause I was so miserable, and got a normal car ’cause I just didn’t need it and didn’t care, um, because it was so worth it to me to leave. So little things like that really added up and gave me that cushion, those, those several months of personal expenses to be able to leave.

Okay, so we’ve talked about financial security as, as the probably the most important logistical step to cover in order for you to be able to leave your nine-to-five. But the other one that you don’t want to skip over is looking at proof of concept.

If at any point in this time when you’re still working, if you can look at, you know, what’s going on in the marketplace, go through like the s- go through the demand and the supply steps that I talk about in my book about how to do research and, you know, looking for who’s out there asking for what you wanna offer, what are they looking for, where is there a gap in the marketplace.

But now is the time to take while you’re still working, while somebody’s still paying your health insurance premium, to actually do this backend research. You don’t need to do this once you leave, right? That should already be done.

I also want you to be in a position where you’re leaving your nine to five with at least some confidence that you actually have a business that’s, like, ready to go and, and has some people that are waiting. Now, we can’t control what happens and how successful it is. As I shared earlier, I left corporate law to start a health coaching business.

By no means was that health coaching business, uh, successful on paper or by any other measurement, but it is what allowed me to start another business, right? So I couldn’t really control whether that business was successful, but I’m so glad I left and I did that because it gave me the idea to do this one.

And last but not least, I would say the last logistical step that you should take care of before leaving your nine to five is to use your time when you’re getting paid by somebody else to do all the boring backend setup stuff, like getting your LLC registered, like buying a domain name, maybe even starting to play around with a website.

Maybe even starting to play around with posting on social media, like just getting comfortable with that. I mean, depending on what you do for work, you might not be used to any of the things that you’re about to go do in your business. For me, coming from corporate law, I didn’t know what an email list was. I didn’t know… Instagram was a, a, especially back then, was a platform that some of my friends posted, like, hyper-filtered or, like, Polaroid-looking photos on.

I had no idea that people were selling stuff on it. Like, I remember even in 2016, the concept that somebody would get on Zoom with a person they didn’t know and then sell something to them, like, it just sounded like a scam to me. So even just, like, spending that time wrapping my mind around it and figuring it out.

As I always tell people, I, I literally remember to this day googling, “What is an email list?” And, and so it’s like just taking the time to educate yourself and, you know, start playing around. Like, I became a Kit customer in 2016, uh, back when it was ConvertKit, but I became a Kit customer in 2016 and set up that account and got everything up and running and just messed around with it a little bit before ev- anything ever became legitimate.

And obviously I would recommend that you get all the legal stuff situated like contracts and registering your business and getting business insurance and all of that. If you want to figure out exactly what you need to do, make sure you click the link in the show notes to come to my last live legal workshop of the year, ’cause it’s next Monday, October 19th.

Um, and it fills really, really fast. So I’ll drop that link in the show notes so you can sign up for that and learn all the steps that you could take before you ever leave your job.

Okay, so I mentioned at the top of the episode that yes, there’s all these logistical issues about, you know, the money and getting things set up and making sure you actually have proof of concept but the part that we probably talk about less often, but that’s actually even more important, are the emotional steps to get ready. Because leaving your job, leaving a nine-to-five, leaving a traditional office to start your own business is not a panacea. Now, I don’t know many people who are as like rah-rah entrepreneurship business as I am.

I love it so much. I get… I just, like, love everything about what I do. Doesn’t mean I don’t get burnt out and frustrated and all that kind of stuff, ’cause I’m human. But I, but I truly, truly love what I do, and I, I literally don’t think there’s anything other than, like, entrepreneurship generally that I really should be doing.

And so even with that, there are really hard parts about it, right? And so, like the reason I called my book When I Start My Business I’ll Be Happy is because that’s not how my story went. That’s how I thought my story was gonna go. I was in your position where I hated my boss or I hated my job.

I blamed everything and everybody for it. And while some of that, a lot of it was true, right, that it did suck, looking back on it I realize that I actually also wasn’t doing much of anything to change how I felt about things while keeping the circumstances the same. Like yes, I think that my ultimate, like, path should have always been entrepreneurship.

I was entrepreneurial since I was a child. But even if I had stayed being an attorney, there were many ways for me to have been a lot happier as an attorney than what I was, and I don’t think I had to leave in order to be happier. I think I’m much happier for having left, don’t get me wrong. But, like, there were things I could have done.

And the reason I think that’s important is, well, one, we have to set the stage as like real- I think it’s important to be realistic.

But two is that you might be listening to this and be like, “I’m not… I can’t change jobs,” right? Like, I hear from so many people because I am somebody who shares openly about, like leaving my job and starting a business. I hear from people all the time who are, are desperate to do that, but can’t for whatever reason.

Like, they have personal circumstances that just don’t allow for it. So I want you to know if you’re listening, that there are things you can do to improve your circumstances, I think, or just the way that you think about it. I think for me, looking back on it, I would’ve said that if I hated my job and my career so much, why was it like the only thing about me?

That would’ve been… That, but that would’ve probably been the hardest thing to, to take a look at, but it would’ve been the most true and honest. I really only hung out with other lawyers. I identified a ton as being a lawyer because, you know, when you tell people you’re a lawyer, it does bring a certain level of street cred.

Like it’s a, it’s a good door opener. You know? It’s like just being like, “Hey, I’m a lawyer.” And then people… There’s a certain level of like automatic respect. It’s like, kind of like when you see a cop in a uniform, it’s just like an automatic level of like, I’m scared of you, right? Like, I’ll respect you.

I’ll do… I’ll, I’ll cross the street in the crosswalk, you know? So I think that there’s, there’s a, um, something to that. But also it gave me this ability to like hide behind it and define myself by it. And looking back, all the stuff that I do now in my free time, like playing tennis and reading and traveling and hiking, like doing all this stuff, I’m like, I didn’t do any of that.

All I did was lawyer stuff. And then I said I hated being a lawyer, so like no wonder I hated my life. And so I think that’s just very interesting and something that was definitely within my control that I did not feel was in my control back then.

But don’t get me wrong, if I could sit down with you for coffee, I would be like, “Yeah, go start a business. It’s amazing. I love it. It’s so much fun,” right? I don’t think everybody is cut out to be an entrepreneur. I don’t think that every person who’s cut out to be an entrepreneur, that their idea is cut out to be a successful business.

So I think that there’s, like, a lot of that front-end work. Like, you might be a very entrepreneurial person, and you’re the kind of person who’s gonna figure it out, and you’re gonna put in all the hard work and effort into figuring it out. But sometimes it’s just that people don’t have the right idea, like they haven’t developed the right idea. That’s why I spent so much time talking about it today and also writing about it in the book.

I think it’s important to think about what am I making starting a business mean? Like, what do I think that that will be, what will be different? What do I think will be, uh, available to me once I start a business, and what do I think’s gonna go away?

I also think another thing you could ask yourself is assuming that everything else in my life stays the same, how will this job change, change things? Like, how will not being a nine to fiver and how, how will being an entrepreneur change those things in your life?

Obviously, I didn’t know when I left the law that I had, I had a real doozy coming for me on the other side with, like, I literally had brain surgery right after then my dad got sick, then my dad died, then my mom died. Like, everybody died. And so I feel like, you know, uh, in a way I feel really lucky because i- if I had stayed, I almost feel like I would’ve been locked in. And I don’t even know how I would’ve navigated having had brain surgery and being employed as a lawyer ’cause I wouldn’t have been able to work for, like, a year.

But I was able to do some stuff in my business ’cause it could be really flexible, and I could sit on the couch and, like, fall asleep or something. So I, I, I don’t know. I don’t… I think I got lucky actually in terms of timing, for being able to do that. But you know, it’s interesting because I just didn’t, I didn’t know any of this was coming, and at the same time I’m like, “Oh wow, look how much, like, worse my life actually got when I started a business.”

But I was able to navigate those things because of my business, so it was both a blessing. Like, those things were gonna happen no matter what. I literally don’t know what I would’ve done, uh, especially once my dad got sick because I was taking him to chemo every three weeks and, and then tons and tons of appointments between, and just, like, h- I wouldn’t have been able to keep my job.

So, uh, yeah. I’ve also heard stories about, like, how after I left people got laid off and things changed and all of this. So I do think there’s also something to this idea, and I’ve had a lot of conversations with you all privately about this, like, there’s… I think sometimes society has this story about how, like, nine to fives are super stable and secure, but, like, entrepreneurship is not.

And I’m like, “Oh man, I feel way safer in my own hands than in the hands of some giant company that could, like, cut me at any time for their profits.” So I don’t know. I mean, I, I a- am more confident these days betting on myself. But obviously that took time. I d- I didn’t think that when I was first leaving, you know, people ask me all the time if I’m worried about my current business being impacted by AI. I’m like, “Well, we’ve had our biggest year yet so far, so, like, I’m not really sure.” I mean, I’m aware of it, and I’ve made certain adjustments as I’ve needed to, but I also am not gonna lose sleep over it because I know I would just steer the ship in a, in a different direction for me and the team.

And so, like, I have confidence that I would be able to figure this out, not confident that I can control whether or not AI impacts my business, you know? So there’s, like, there’s shit on the other side of starting your own business. There are things that come up. There’s, there are mean comments. There are annoying people.

There are angry customers. There’s people who you can never do enough for them, and they’re always gonna be disappointed in you. There’s management of a team, right? Like, I, as a lawyer, I never had to manage anybody else. I don’t think it’s my greatest skill, and it’s not something I thought about when I started the business, I just thought like, “Hey, it’d be fun to write and create content and, like, sell things.”

But I never thought like, “Oh yeah, there’s gonna be people, like, who need me and are asking for things,” right? So there’s all these, like, new roles that it brings to your life, which I think is great on the one hand because it stretches you as a person and you have to learn new things, and it’s challenging.

Like, there are other, there are new challenges that businesses bring that your current job doesn’t. So I guess I say that as like the, the big sister moment of just saying like it’s important not to make this leap mean something more than maybe it does. I think being realistic about what a business that you, of course your business is going to have challenges, just like your job has challenges, and so it’s like, are, do they sound like challenges though that you want to tackle? I think that’s the biggest question. Like, my business has so many things day to day, year to year, that would probably drive somebody else crazy and really would bother them.

And for me, it’s just like, yes, they bother me, But there are also things that I just want to work through, and I’m okay with it, whereas when I was a lawyer and something would go wrong, everything felt monumental and like something I did not want to deal with, and I just didn’t even have the energy to navigate it.

I also just wanna say quickly that fear of leaving your job, fear of like, could I get this wrong? What if I take the leap and then I regret it? That that’s very normal.

I left my job on Friday, August 19th. My… I took my dad and Ryan to Carrabba’s to go get some pasta, and we went to Carrabba’s. And I remember sitting there and having this meal with my dad and Ryan, and they were talking, as always, ’cause, like, oh my God, those two, they just would not shut up.

They always talked. I would just be like, “Why don’t I just go? Like, you guys don’t need me.” You know? So they would talk probably about football or, like, arguing about something, and they love each other more than, like, life itself. And so I was sitting there, not paying attention to them as usual, and I was like, “Oh my God, what did I do?”

And it was, like, 6:30 on Friday night, the n- the day that I left, and I remember thinking that the managing partner, I had her number, and I was like, “Maybe I should just text her. Like, maybe I should just text her and be like, ‘I’m so sorry. I I messed up. I, I’ll come back.'” You know, it’s like, like begging your lover, but I was like, I just, I was like, “I’m so sorry.

Like, I shouldn’t have left you,” and like, “You guys were right. Like, I’m a fool.” Like, when, when I went to go leave, they were, they were like, “Hey, you know most businesses fail, so we’ll keep your job for you, like, forever. You can come back whenever you want.” And I, you know, the Philly s- girl in me was like, “Pfft, I won’t need you.

Like, bye.” You know? And I was fine, and then I was like, “Oh, God, I should text her and be like, ‘I’m so sorry. I, I was… What an idiot,’ you know? ‘Take me, please. I’ll work for anything. $5 an hour.'” So I really panicked, and I spent that whole weekend just feeling really frozen, uh, feeling like I had messed up. And Sunday night, again, like, “Okay, I would’ve been going back to work tomorrow, and I’m not.

Maybe I should text her and say, ‘Can you take me back?'” I remember talking to Ryan about it and him saying, “Why don’t you give it a week or two? Like, they said that they’ll take you whenever, so why don’t you just give it some time?” And I’m so glad that I did, because I think that fear after the leap doesn’t mean that you chose wrong.

It doesn’t mean that you did something wrong. I think fear is just normal. Like, I would probably have been more nervous if I wasn’t fearful, because I think either, A, I would’ve been a narcissist, or, B, like, I was just delirious about what I had just done. And so it’s normal, and I would encourage you not to make any rash decisions, to give yourself some time.

Um, but I also think that’s why it’s really important to have done the things that we’ve talked about today, because I knew I had the financial stuff set up. Like, I had saved, and I had set aside my expenses. I wasn’t relying on the money from my business yet. And so I was able to just, like, take my time, because things were slow in the start

now, three months before that Friday, August 19th, when I was, uh, walking out of the firm for the last time and I took a grainy, grainy little photo on my old iPhone of the, uh, dark mahogany doors into this, like, the waiting area of the law firm, which I have saved as a favorite and look at it all the time, uh, with a gigantic smirk on my face by the way.

But, um, w- three months before I took that photo, I was on a plane. I was on a plane on the way home, uh, from Amsterdam back to Philadelphia, and halfway over the Atlantic, we experienced what could only be described as a horrifying s- like, as- event of turbulence, uh, where the plane dropped and it kind of rolled t- really hard to the left, and shit went everywhere, and people were crying, and I was freaking out.

I thought I had a heart attack for sure. But as we were, uh… What I thought was going down turns out was just really bad turbulence. But as we were, as I thought that that’s what was happening, I, I had as what I can only describe as, like, my only come to Jesus moment where I was just like I am done with this.

I am sick of being that complaining attorney. I’m sick of walking into that law firm staring out the window. I’m sick of everybody t- asking me, “Why are you here?” ’cause obviously you care about all this other stuff that has, like, nothing to do with legal. And I was just tired of waiting for something to happen.

I guess I realized that I was waiting for something to happen. So within three days of that airplane ride and landing back in Philadelphia safe and sound, I bought a domain name. I registered an LLC. I set up business insurance. I obviously wrote my own contracts ’cause, you know, lawyer things. And I got all of the backend stuff done and set my mind on leaving that law firm, setting aside money, starting to save, selling stuff, doing all the things that we’ve talked about today.

And by August, I was walking out of those doors. Now, s- side note, I left that firm to go work… Like, I, I worked part-time for, like, another three months before I fully, fully left, so it wasn’t, like, my final out, but it was my final out of a full-time law firm gig and that allowed me, again, financially to just, like, float myself a little bit longer.

But point is, I left, and I am so glad I did. And if I could tell you anything as you’re maybe considering this, is that the legal setup is the easy part that you can actually do before you quit. And that’s going to get even easier if you come to my last free live legal workshop next Monday, October 19th at 3:00 PM Eastern, because there I’m going to show you every single thing that you need to do, the five easy steps you need to take in order to get an online business started the right way.

Plus, I’m gonna keep you updated on all things AI, ADA compliance, and personal privacy. So make sure you click the link down in the show notes to save your free seat at my last live legal workshop of all of 2026. It fills super, super fast, so go ahead and click that link, and I hope to see you there. If you can’t make it live, make sure you sign up anyway so you can get the replay.

I’ll send it out to you both by audio and video. With that, thank you so much for listening, and I can’t wait to see you hopefully all at my last live legal workshop of the year next Monday, October 19th. See you then.

Thanks so much for listening to the On Your Terms® podcast. Make sure to follow on Apple Podcasts, Spotify, or wherever you like to listen to podcasts. You can also check out all of our podcast episodes, show notes, links, and more at samvanderwielen.com/podcast. You can learn more about legally protecting your business and take my free legal workshop, Five Steps To Legally Protect and Grow Your Online Business at Samvanderwielen.com and to stay connected and follow along, follow me on Instagram at samvanderwielen and send me a DM to say hi.