Ep. 21: How I Knew it was Time to Leave Corporate & Start a Business

Note: This is the transcription from episode 21.

Do you ever feel like you were made for more in your career? Like maybe you've climbed the corporate ladder your entire career and now that you're up there, now that you have an incredible job or maybe you do on paper, you're just like, what else is out there for me?

Or maybe you're new to the corporate world and you're already feeling like it just isn't a fit. Maybe you're in a new job and you're like, why am I already feeling like this isn't for me when I've only worked here for a month or two? If you're feeling any of those situations, I first want you to know that you're not alone.

I think it's actually pretty common, especially when you work in corporate, to have a lot of influence on feelings of unfulfillment. I feel like corporate culture can be very damaging, it can be very toxic, but it also doesn't have to be, right? Sometimes we're in a job and there's not all these negative, toxic factors, but for some reason we're still like, I don't know why, but I just kind of hate it, or just don't feel like it's a good fit for me.

Well, I want you to know that I've felt this way multiple times throughout my corporate career. And we're talking like 13, 14 years. I've worked for startups. I climbed the ladder. I had the most “perfect” corporate leadership jobs that I've had in my career that I'm so proud of. But in a lot of those jobs, I was like, “Why do I just feel like this isn't for me? Or I feel like there's something else out there that might be a better fit.” I will admit I'm a little bit ADHD. I get excited about starting something new, about the possibility, about opportunities that are out there. Like when I was in school, I would rather be outside or I'd rather be in another class. I just couldn't sit still and focus when I kind of had a box around me. When I had these teachers telling me exactly what I had to do and it kind of just made me uninterested in whatever that activity was because I wanted to have more freedom. And honestly, that's why I almost failed out of high school.

But I went on after high school to go to grad school and I graduated with honors from business school, which I think that just shows that like, I can do well in school if I'm actually interested in it, right? I don't know if that relates to you at all, but my whole point is, sometimes we're just in a situation that we're not happy with and we can't necessarily put our finger on why we're not happy, but we're just so freaking curious about what else is out there.

So I also want to say, that's okay, especially again when it's your corporate job, like there's just a lot of box around you, right? And I think that was one of my big problems when I worked in corporate. There were so many rules and so many people around me and I had a boss and they had a boss… It was just this kind of environment that I couldn't feel 100 percent myself, but I still did it anyway.

And that's why I was able to climb the ladder in 13, 14 years. But now in 2024, I am almost a year into being an entrepreneur. I left corporate, my final corporate job almost exactly a year ago. And it's so wild to think that it's already been a year. Because whenever we're in a situation where we're just unhappy or unfulfilled, it kind of feels like it lasts for like at least 25 years.

I feel like my last job, even though I was only there for about a year, it feels like it was 10 years. And I loved a lot about that job. And I still learned a lot. I still gave it my all. I was all in. But there was just something about it that was telling me, “Lindsay, this is just not right for you. And there is something else out there and you have to trust it, but you're going to have no idea what that looks like until you go for it.”

So since I'm almost a year into entrepreneurship, I wanted to record an episode today that was dedicated to the woman who's like, How do you know if it's time? How do you know if it's time to leave corporate for good? Or maybe just for now. Like, maybe I just need to take a break from corporate, from that culture, try something else, and then realize, this is actually what I want to do. I'm going to go for that now. I get this question all the time because a big part of my story was being completely unhappy in corporate, especially my last few jobs. And just having this feeling of like, trust the process, there's something out there for you. But my fear held me back big time. Looking back, I'm so glad that I finally took that step toward leaving corporate. Like I remember the day I gave my notice and I was so worried. And I was like, “Is this right for me? Am I making the wrong decision?” Especially when it's such a big decision, because I'm single, I pay all my bills, I'm fully independent. And so I can't really just quit a job and not have one lined up. But I actually did that. It did work out. And now I want to share how I did this because no, there's not like a trick to it of, you know, I didn't have, you know, years worth of savings ready to go, that I could just live off on that for my first six months. I didn't have all my bills paid for. It wasn't like I had zero debt. So I had to have income. And it also wasn't like I have another job completely lined up. I quit. I had nothing lined up and it was during the holidays.

So if you're looking for a realistic story of someone leaving corporate, starting a business and doing it from the ground up without the, like I became a millionaire overnight story, then this is it. And so if that's you, if you're feeling like, okay, what's next for me, I just want someone to kind of inspire me or just support me. Then girl, you are in the right place. And when I was going through that, I honestly wish there was someone I could just ask all my crazy questions to who could just kind of help me decide what I actually wanted to do with my life.

So today, I am going to share answers to these questions that I've received all the time in the past year that I receive when I'm on podcasts. that I receive on social media, even on stage, when I'm sharing my story, there's so many women who come up to me and say, “My story sounds a lot like yours, or I'm thinking of leaving my corporate job.”

And so I wanted to share these answers. I wanted to get completely honest with you, give you the 411 on what it's really like to leave corporate and start a business from scratch. Okay. I just want to put that out there. But I'm going to be straight up with you because my hope is that you're not going to make a decision after listening to this podcast. My hope is that you're going to get inspired by thinking, okay, someone actually did this. So it is possible. And I also want to get you thinking, I want to get you to answer these questions because if you're serious about maybe leaving your corporate job and you haven't really told anyone, or if you only told a couple of people and you're like, that would be stupid, right?

But you're like, right, or tell me that it's not, I'm here to tell you that it's not stupid, but I want you to know the truth. I want you to know everything that I went through in this journey, because whether you're just like me in your situation, or whether you are married, you have a family like that's a lot of responsibility to just up and leave your corporate job for.

So let's go through these questions and have a fun little q&a.

How did you know it was time to leave corporate?

That's pretty broad, right? But when I think back about how I actually knew it was time to leave, I remember just at my end, like I remember feeling just so unhappy and so unfulfilled, like it was really messing with my mental health…where I didn't want to go to work anymore. I didn't want to travel and go on the trips anymore. I was just like, “This just isn't for me. And now that I've decided that in my brain, I can't get it out of my head.” But I didn't really know officially that I was leaving until December of 2022. I was having a conversation with my boss at the time, and I was just saying things like, “I'm feeling burned out. I'm overwhelmed. I don't feel like I have a lot of support. We don't have the right team to get done everything that we're trying to get done.”

And I want to be honest and say like, I'm a pretty hard worker. I never commit to something and give it only 50%. So I know that I was working my ass off. I just couldn't make everything happen. I just felt like I was working 12 hours a day and nights and weekends and I could never catch up. I couldn't breathe. And so I was having this conversation and there was just this answer or this reply that just made me realize, you know what, I already know the answer. And that was honestly when I knew it was time.

When I was like, I'm trying to have a conversation, I'm trying to meet in the middle, but in my heart and in my soul, I knew that it just wasn't worth it. I knew that I was going to leave anyway. And so I was given the question to come back and answer, are you ready to travel more, to work as many hours as it takes, or are you going to walk away?

And 24 hours later, I came back and I said, “I'm going to walk away.” But more than that, I was choosing me. Because I knew how many hours I was working. I knew how many tasks were on my plate. And I knew how badly it was messing with my health. Like, not just my mental health and making me not sleep at night and, you know, making me anxious about every day that I had to work, but my physical health too.

I was so drained. I was so burned out and I just felt exhausted and it was totally messing with me and because of that too, I couldn't really do everything in my job, right? If I was on like day one and I was just ready to jump in, that's one thing, but I was just so burned out. You know, it's like a candle that has only a little bit left, and there's still a wick in there, and you light it, and it's like, there's not enough candle in here for this wick to stay lit. But you try, you keep lighting it, you're like, there's a little bit left, there's a little bit candle left, right?

When we're burned out, there's nothing else left. There's really nothing else that will help us get through that besides rest. And besides like a break from whatever is burning us out. So truly, I knew it was time to leave when my body was telling me. It was like loud and clear. Not only did I feel it and hear it from my gut, but just my whole body was like, you know, you know what to do.

And you listening now, you know what that feeling is like. And if you're getting that feeling…I have totally been there. I know how scary it is, but you have to listen because you don't really know what's going to happen in the next week or the next month. And if everything in you is saying it's time to leave, then it's definitely time for you to start listening to that and start creating a plan.

How did you get the courage to leave your job?

This kind of relates to fear as well, because for me, I wasn't just thinking about, “I just need to quit this job so I can find something better.” I was like, “This is my dream job. I've been after this job for a long time. And it really does feel perfect for me. So, I'm scared to leave. I'm scared to give something up this good.” I was also scared to leave a consistent paycheck. I mean, I think that's a lot of us. We're just worried about what it's going to do to us financially. And that's just too big of a risk. Totally get it.

That's totally valid. But also, again, I was like, I'm either going to be burned out and I'm going to get fired because I can't complete the work that I'm supposed to do because I'm not sleeping at all. And I'm traveling every week or I have to have a break. I have to take time off or I have to quit or whatever it is.

So that's a big fear, right? Financially, it kind of takes over everything for you. But also, I don't know, I just had this connection with my body where I was like, “You know what? If you're being this loud and telling me that it's time, I'm going to find the courage to leave.” And what I will say is I don't feel like I actually got that courage until I actually said the words. Until I was like, I am going to give my notice and I am going to walk away. And I feel like instantly. Like, I feel like there was a high five in my stomach where it was like, yeah, like you knew it, you knew that was what you're supposed to do. So, I feel like you get that courage step by step and you continue to build that courage as a new entrepreneur and as you're figuring out what is next for you.

How did you know it was time to start a business?

Well, here's what happened with me. So I did quit and I gave 30 days notice. So I had 30 days to find a new job or figure it out. It was during the holiday season, which I do not recommend. That was a terrible time of year to quit my job, but I actually did get a bunch of interviews. I think I had like 12, 15 interviews total during a one or two month timeframe. But something that happened is I would interview and I would try to get the job because again, that's what we're supposed to do, right? We're trying to go after these jobs and we're just going to accept it no matter what. If we're getting a paycheck, if we know how to do most of the job, then we're just going to go after that job no matter what. Well, there's like something changed in me after having gone through two jobs that just, I felt like weren't a fit for me.

And I was like, you know what? I don't want to go into another company or to go into another job just because they're hiring me if I'm not going to be happy. And it was clear during these interviews, I was like, um, that is a red flag. That's a red flag too. Okay. They're taking this out of the job description. Like there was just so many things that I was like…this is a warning to me. I need to listen to that. And so I had this realization of like, you know what? Maybe I should do something on my own. So I joined Upwork. I joined Fiverr, the sites where you can get a contract overnight. It's kind of easy to get these contracts because they're a little bit smaller and they're one time usually.

So I went all out there and I did get a couple of clients right away. I mean, there were smaller projects and definitely not enough to keep me going in a business. But what I did get was some confidence. I was like, okay. So I tried something on my own and I proved to myself that like, this could actually be a thing.

This could actually be a business. And so for me, it was kind of an accident, this falling into starting the business. And even though I thought about it. In my life before that, I just wasn't serious because I was like, “I am at my wit's end. I need income. There's no way I can start a business and make money right now.”

But I did. And it was so wild. So how I knew I wanted to start a business was because like I needed income. And so I had to find income right away and honestly doing some contract work filled that void for me. But it also showed me again that I could actually do this. Another thing that I did was I kind of workshopped my strengths and my weaknesses and what I actually wanted to do. Like the actual work that I wanted to do I knew what my experience was, but I was also doing stuff every day in corporate that I was good at, but I didn't like doing anymore.

I feel like we wear all the hats in corporate. And so for me, I workshopped those things. I workshopped, I'm really good at this and I love doing that. And then once I kind of had this list of what I really want to do and what I don't want to do, I built my business around that because here's one of the things I figured out is like, you can start.

You know, your first business or your first month in business, just to kind of test it out. And then you'll realize, you know what, I actually really like this, or this taught me something else that I want to offer. And so I think just kind of going for it, testing the waters a little bit within your field, but as a contractor, or maybe you're taking an online course or a workshop and you're learning something new, you kind of have to figure it out, like what you like and what you want to do.

And then you'll figure out the rest, right? Like the services that I started with almost a year ago, I now niche down to only offer two services rather than like 10 because I was just open to any client, but you figure it out as you go. And the most important thing, the most important reason behind this is like, you're not going to know without trying.

You're not going to know what starting a business is like until you're in it. And it is definitely a roller coaster. I've learned so much like every week of being an entrepreneur, but you do figure it out. And there is the motivation there because you don't have a full time job, a consistent paycheck. So you're going for it. You're figuring it out. And that's honestly a really fun part of becoming a new entrepreneur. So even if you have the idea of starting a business with your past experience, or maybe you're really good at something that you've never gotten paid for… So you just never know what is possible. Write down all the things you like doing. The things that you don't like doing and freaking create your business out of all of that.

What advice would you give to someone who's interested in leaving corporate?

The first thing I would say is, I want you to write down your why. Your why in life, in general, and in corporate, in business, you know, in your career. What is your why? Do you really like helping customers? Do you really like solving problems? What is your why? So I want you to start there. The next thing is, again, do that workshop where you're figuring out what really lights you up and the things that maybe you're not into anymore.

So definitely write those things down and don't create a business of doing something that you really don't enjoy doing. That's just going to kind of burn you out again or make you realize that maybe it wasn't corporate, maybe it was the actual duties in your role that you didn't like. So just write those things out.

And then the third thing is I would say go for it. If you're curious about starting a business, look, you don't have to quit your corporate job before you do that. It could start as a side hustle, or maybe you're learning more about how to start a business while you still have a job. But if you don't go for it, you're never going to know what it's like to be on the other side.

And let me tell you, I am so happy. And I'm so grateful that I took the chance because now I know what it's like to be an entrepreneur. And it is not easy by any means, but it is something that I love. I love to figure out how to do it. And looking back at a year ago when I was super unhappy and just wondering like, “What the hell am I going to do in my career?”

Now I know, and I wouldn't have known if I didn't take that risk. So I'm just really grateful for that, but I'm just excited for you. because even if you're listening to this episode and you're like, “I'm curious, I'm scared.” Try to figure it out, girl. I am just excited that you have this passion and this curiosity in you.

So keep going in that direction. Don't put it on the back burner. Don't just deal with the job you have. You really truly deserve to be happy. And let me tell you from being completely depressed and anxious and unfulfilled almost a year ago, I am so grateful that there are other opportunities out there and sometimes you just have to create them.