Welcome back to another episode of Quit Your Job, Sis: Unhinged!
In this episode, I take you back to the very beginning, and I dive deep into all my “failures” as an entrepreneur:
I discuss the fear of failure and its integral part in the entrepreneurial process. I share about my success - not to brag, but to shed light on the hurdles I’ve faced in the hopes that it inspires your journey, too.
I discuss the challenges that I faced despite small wins and struggling to pay my bills. How I reached a breaking point, how I handled each experience, and how they led me to where I am now.
My story is a testament to the power of persistence and the willingness to seek help when I need it. Through all the ups and downs, I’ve learned the value and importance of handling setbacks gracefully of not letting them stop me from chasing my dreams. I’ve learned the importance of believing I was worth it and investing in myself, even when finances were tight.
Remember: every successful entrepreneur has faced their share of failures and uncertainties. It's how we handle those challenges that define our journey.
Tune in to this week’s episode for some unfiltered inspiration and valuable insights on what it means to “fail” in business.
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[00:00:59] Lindsay: Hello, my loves, and welcome back to another episode of Quit Your Job Sis Unhinged. What I decided that I wanted to do today is walk through all of my failures as a business owner, and there are a couple of reasons why. So, just for myself personally, this is something that I was thinking about the other day, and I just remember there were so many times in my business when I didn't know if I would ever make it here.
[00:01:32] And it's not like I've reached my final destination, you know what I mean? I still have goals, and I still have a lot of things that I want to accomplish as a business owner, but there were so many times when I didn't even know if I was going to get here. And so, for myself, I kind of just want to reflect on the things that I had to grow through to get here.
[00:01:58] But also, I know for many of you who are listening, you might be feeling that way right now and wondering if you're ever going to make it. Or maybe you're thinking about quitting your job and starting your business, and you're worried that you're going to fail. And I'm here to tell you that you probably are, and you probably are many times, but that doesn't mean you can't make it because failure is part of the process, and that's something that I have learned to embrace, and so I'm hoping that this can be inspirational for those of you who might see where I'm at now and think that it was somehow easy for me.
[00:02:35] Think that I didn't go through the failed launches, the programs that no one signed up for. There were plenty of times that happened to me, and we're gonna go through them today. So, we're gonna take it back to the very beginning, y'all. 2018, right around this time of year, actually, five years ago now, which is crazy. This was the time that I quit my job and started my business, so...
[00:03:04] It was November, the Monday after Thanksgiving break when I went in and put my two weeks in. And the first thing I did after that, I think it was like the next day or sometime that week, was I hired a business coach. And that is not something that I regret doing; that's actually something that I'm really glad I did because I don't think I would have known where to start without having someone to guide me through that. So, I was working with that business coach. I think it was a six-week program with her that I started at like the end of November and into the beginning of January. So she helped me to put together my first program as a fitness coach, figure out what the heck to post on Instagram to get clients, and then launch that program in January.
[00:03:52] And because of that and the work I did with her, I signed on five clients in my first month. So again, that's not one of the failures. That's just to give you some context. But after a few weeks, I was no longer working with that coach. And I did sign three more clients in my second month. And then, after that, I was really struggling to sign on more clients.
[00:04:19] For a while, I mean, I don't remember the exact numbers. I could go back, but that's not really the point. I just remember feeling so lost because I didn't have a coach anymore. I thought that I knew what I was doing because it was working at first, but then it kind of stopped working, and I was like, "Well, what do I do now?"
[00:04:38] Looking back, I think I had just tapped out my Instagram audience of, like, 200 of my Friends and a few random people who had found me at that point, but I think I had just kind of tapped out that audience. If I could go back, I would probably have tried to reach other people's audiences or grow my audience in some way I might have done guest podcasts or guest appearances on other people's social media or programs or different collaborations with people to try to kind of reach someone who already had the audience that I was trying to reach, right? But anyway, I didn't know what I didn't know at the time, and so I started just trying way too many things to see what would stick. But the thing is, with marketing, you really gotta try something for long enough for it to actually work.
[00:05:32] But I felt like I was just like throwing everything at the wall. I would do a free challenge. I was constantly switching up what my lead magnet or free offer was. I was doing free consultations, and then I was trying to offer a free workout program. I would create a free workout program for you. I was doing free challenges, it was all very confusing, which, looking back, I'm like, duh.
[00:05:59] It makes sense why no one was signing up because everybody was probably fucking confused, right? But also, I think, and this is probably something that happens to a lot of us, especially in the beginning, when people aren't signing up, and we think we have to offer more things for free. That's usually not it.
[00:06:17] It's usually just how you're marketing or who you're marketing to. But the thing with me... Offering more, more things for free to try to get people in the door, so to speak, is that I would end up targeting the people who are just looking for free stuff. They weren't actually ready to invest in a coach.
[00:06:39] They just wanted like a free workout program, and I don't blame them. That's what I was offering. So, I was getting a lot of interest, but no one actually wanted to invest in coaching. So anyway, at some point throughout those first few months, I remember I bought a thousand dollar course from someone who was like a pretty well-known business coach, and she put together a course with like A bunch of different trainings that she had done on different business topics and bundled it all up for a thousand dollars, which was supposed to be like a huge deal, right?
[00:07:23] And I bought it, and there was a lot of information in there, and I learned a lot, but I think the issue with that was that it was like information overload. And so it gave me, it just gave me more things to keep throwing at the wall. It wasn't really a focused strategy. It wasn't something that was going to help me identify what wasn't working in my business and why I wasn't signing clients.
[00:07:49] It was just like, here are more things that I could try and see if they work. So, I don't know that I would say I regret that purchase, but looking back, it wasn't what I needed at that time, and it really didn't actually help me in a tangible way. Okay, fast forward to, like, August or September of 2019. That was when I made the transition from fitness coaching to life coaching, and I sort of niched down to career coaching for accountants because that's what I knew. That's where I was. Those are the people who I knew I could speak to because I had been in their shoes, right? And so because I knew I was targeting accountants and specifically people who worked in public accounting and were kind of newer in their careers.
[00:08:41] I was like, well, they are all on LinkedIn. So let me figure out this whole LinkedIn thing and see if I can find clients on LinkedIn. So I remember I bought a course on Udemy for probably ten or however much it was that taught me how to optimize my LinkedIn profile. And I can't remember if it also gave me templates or guidance on how to message and reach out to people and find leads there.
[00:09:07] But I remember that's how I learned how to optimize a LinkedIn profile, and now I, you know, get paid thousands of dollars to do that for other business owners, but I got started on LinkedIn, and it started working for me, and I was getting calls booked pretty consistently, I signed a few clients between September and the end of the year, but it wasn't A lot of money by any means. I was really starting to drain my savings account and kind of getting to the point of like, "What am I going to do if I don't start getting more clients and making more money." So, I decided to invest; I think it was in November. I joined a group coaching program with the person running it was someone who I had been following for a while, and I really looked up to her and how she ran her business. And so, I joined her group coaching program, hoping that it would help me to give me some direction and figure out how I can sign more clients.
[00:10:12] During the course of while I was in that group coaching program, I had a call with a lead who I found from LinkedIn for one-on-one coaching and the call went really well, and she ended up signing up. Or saying that she wanted to sign up, she wanted to pay in full, ready to go. So, I sent over her agreement form and invoice.
[00:10:37] I don't even remember how I was doing those things back in the day. But I sent over whatever she needed to actually sign up after we got off the call. And then, the next day, I had a message from her saying that she wanted to back out. And... This was like, this is literally the most traumatic thing that's ever happened in my business, and I say traumatic not because it was like really that serious, but just because this literally altered the way that I interacted with clients from this point forward, and it really, it's just ...
[00:11:15] Let me just explain what happened. So I saw that message from her, and, one, I was really l devastated because it was literally going to be the difference between me paying my rent in January or not I if I got this client or not, but I was trying not even to focus on that because I don't ever want to put that on a potential client. It's not their responsibility to pay my rent, you know what I mean?
[00:11:43] So I was just thinking of how do I even handle this situation because she was so on board yesterday, and I knew I could help her, and I knew, based on what she was telling me she wanted to do, I'm like, I know this is the right step for her, I know I can help her. And yesterday, she knew that too. And so, what changed?
[00:12:02] And I, I wanted to see if I could help kind of, I guess, understand her thought process or walk her through that fear, because likely when that happens, it's like, they know it's the right next step for them, but then fear steps in and doubt steps in, and they're like, “Maybe this isn't the right decision.”
[00:12:20] So I messaged the coach who I was within that group program and asked her what I should do and how I should handle it, and she was like, here's what you should say back to her. You should try to get on a call with her so that you can walk her through it and just let her know that you need to get on a call before she can just back out.
[00:12:43] Oh, I know what happened. She had paid. She had paid in full on the call and then messaged me the next morning, wanting to back out. So it was like she had already paid, but she wanted her money back. And so I sent her the message back, and I was like, yeah, it's fine. If you want to back out, I just like to have a call first so I can understand.
[00:13:02] And then it just so happened that she was traveling that week. So we couldn't get on a call until the following week. It was the holidays. It was a whole thing. And so that whole week, I was just like, it was in the back of my mind. I was anxious about it. And this is why it was a traumatic event, because it was just this prolonged thing that became a bigger deal than it ever needed to be, and it would just… it gave me so much anxiety.
[00:13:28] So... We got on the call, and it didn't go great, and she was basically annoyed at me for not just giving her a refund when she asked for it, which, again, is fair. Um, fully fair. And I just felt so uncomfortable with the whole situation because it really wasn't how I would have handled it, and I just was saying things because that coach was telling me that's what I should say. And she was telling me that this had worked for her. And so I was like, okay, this- it doesn't feel like it's really aligned with how I want to handle this situation, but I'm just going to do it and hope for the best, but long story short, I ended up refunding her the money, and she didn't want to continue coaching and.
[00:14:12] So then, it was the end of December, and I, literally, my bank accounts were drained. I didn't have any money left. I didn't know how I was going to pay my bills in January. I didn't know how that was going to happen, and I was just really discouraged after that whole situation. And I just had, I don't even know what to call it, but it was like the lowest I've ever been in my business, mental breakdown, existential crisis.
[00:14:45] I don't know if I can do this. I might have to go back and get a job. That was kind of the moment I had. After that point, I started applying to part-time jobs in my area because I was just like, I need a way to make money to at least pay my bills, or I don't even know what I'm going to do.
[00:15:04] I'm going to have to call my dad and ask him for money. That was my, that was my backup plan. And there was actually a day that I had, I literally put it on my calendar at some point in January when it was like the second to last week. And I was like, if I don't sign a client this week, essentially.
[00:15:21] I'm not going to be able to pay my rent on February 1st. And so I literally put something on my calendar to call my dad and ask him for money. And then, right before that call, I ended up signing a client. I've told that story before. So it's also in a past episode if you want to hear more about it, but yeah, I've actually not been able to pay my bills since starting my business.
[00:15:43] Fun fact. I've gotten very close to not being able to pay my bills. There were many months when I didn't know how I was going to make the money to pay my bills, but I always did. And that's an energetic money thing that I've also talked about before, but fast-forwarding a little bit to February/March of 2020. During this time, and I don't remember the order in which I did this or like how close to each other these investments were, but I invested in a life coach, and I invested in Amanda Frances's course, Money Mentality Makeover, which I've talked about before. And you're probably wondering Lindsay, I thought you didn't have any money.
[00:16:28] I didn't. I put both of those things on my credit card, and I was just like, "This is either gonna work or it's not." But it was my last ditch effort. Literally, I was like, "I don't know what I'm doing. I can't figure this out on my own." And so both of those, the coach who I worked with and Amanda Frances, I felt like I knew those things were the right next step for me, and I was willing to go into credit card debt for it.
[00:16:57] And at the end of the day, if I had to go back and get a full-time job, I would have, but I wasn't willing to do that until I knew that I had tried everything. And so, to me, this was my last ditch effort of I'm going to try this. And see if it works. And if it doesn't, then maybe I'm not cut out for being a business owner, right?
[00:17:18] But at least I'll be able to say I tried everything, and I did everything that I could. And so, part of that is asking for help when you need it. But, after I started working with that coach and going through Amanda's course, I started seeing results pretty quickly. I think I signed a couple of clients within a few weeks.
[00:17:41] I started making more money. It was like enough to pay my bills minus my credit card bill. I don't really remember what I was doing in terms of practical business things. I remember that I didn't change much that I was practically doing, but through the work I was doing from Money Mentality Makeover and from working with my coach, it was a lot of mental work, and energetic work.
[00:18:06] And even just from doing that, I started seeing, like, I started signing clients. And I wasn't really changing any actual strategy that I was doing in terms of my marketing, right? So that was an interesting kind of shift for me to see that even just energetically, the mindset I'm in and how I'm showing up can have an impact on my marketing and getting leads through my business.
[00:18:29] So I started to sign on a couple of clients here and there. I was making enough money to pay the bills, but it still wasn't consistently profitable months. And I don't remember exactly what I was doing at that time. I feel like that was a time when I... I just remember recording a lot of videos. I felt like I really wanted to be on video and talking to my audience.
[00:18:55] I remember doing a couple... Running a couple of five-day free challenges in my Facebook group that I then turned into mini-courses that I put on my website. I think this was also when I launched my membership. Does anyone remember that? And that went okay. I did get A few clients in that membership, and I had some people who were in there long-term, but I never had more than four or five people in there at a time.
[00:19:25] I don't think so. It was good. I made a few sales, but I wouldn't consider any, anything I had done up to that point, a huge success. I mean, I guess my first month signing five clients was a success, but there was nothing... my membership launch wasn't a huge success. I think I signed a couple of people the first time I launched it.
[00:19:51] There was nothing that was really like, "Oh, I did that." I hadn't really had that feeling yet, but this was the time. Oh, actually. Okay. I forgot about this. After my little mental breakdown in December of 2019, where everything was falling apart, that was actually when I decided to start my podcast.
[00:20:13] I don't really remember why that was the moment, but I think it was just like, I had hit rock bottom, and I was like, I can only go up from here, and I had been thinking about starting a podcast, so I was like, you know what, maybe this is something that can help, or at the very least it's going to be a way for me to kind of like share my story and document this whole process and this whole journey.
[00:20:33] So I launched my podcast in January of 2020, and after a few months, I started getting pretty consistent coaching applications from people who had found my podcast. Which was pretty cool. And so, I remember, I think it was September of 2020, I had my biggest month in my business, a five-figure month. I signed three clients in a week, and it was the most money I had ever made.
[00:21:03] And... It was a little bit shocking. It was actually very shocking. And going back to that client, that situation where the client had backed out after signing up to work with me, by the way, the reason I say that was traumatic is because every single time I've signed a client since then, even now, like it's less so now, but even now I sometimes will have this thought in the back of my mind of like, "Oh, they're going to back out."
[00:21:29] If I sign a client and then I, the next day, have an email from them, I'm like, Oh, they're changing their mind. They don't want to work with me. It's literally never happened since then, and yet my brain still has this literal trauma from that one time it happened that still comes up, and I have to, like, remind myself, no, they probably just are asking when our first call is going to be. They're not backing out of wanting to work with you.
[00:21:57] So, anyway. After I signed three clients in one week, I don't think I knew how to process that, and it was like, this is too good to be true. It was like, it can't be this easy. And I just got really fucking triggered by that. And then, after that point, it was like it didn't feel safe to my nervous system.
[00:22:18] And so after that month, I literally couldn't sign a client to save my life for like months. Because it didn't feel safe. I mean, I didn't know that at the time. I was like, I just signed three clients in one week. Why can't I sign anymore? But it was like, looking back, I'm like, Oh, my nervous system was freaked out by the fact that I easily signed three clients in one week.
[00:22:43] And the thought of being able to do that over and over again is like, I can't fathom how quickly my business would grow and how quickly my life would change. And it felt unstable. And so, energetically, I wouldn't allow myself to sign any more clients. I was having discovery calls, but it just… it wasn't happening.
[00:23:03] And so in early 2021, I reached a point where those clients who had signed on in September all had kind of wrapped up their programs. And I was deeply in credit card debt because I had been putting my coaching payments on a credit card for almost a year at that point. And again, I just felt like I was back at this place of like, what am I doing wrong?
[00:23:28] All the things that I was doing before that worked are no longer working. And I felt like a failure, and I felt like, what the fuck am I doing? And then I also just, I like, could not afford to continue with my coach and get deeper into credit card debt. And so, I... It was just, it's a rollercoaster, y'all.
[00:23:49] Entrepreneurship is a rollercoaster, especially in the first few years. So, like I said, I stopped working with my life coach, who I was working with, and I was trying to think of ways, outside of coaching, that I could maybe make some money. I think this was the time when I launched my Business Builder Bundle course, which, again, I had a couple of signups but nothing. It wasn't, and I wouldn't call it a successful launch.
[00:24:18] This was also a time, if any of you remember this, when, I think this was when I launched my Patreon for the podcast that literally no one signed up for. Not a single soul. I was promoting that for months, but no one ever signed up for it. And looking back, I'm like, probably because I did zero market research to see if that was something my audience even wanted.
[00:24:41] Yeah, make sure your audience actually wants something before you launch it. Friendly tip there. But... So again, two other kinds of failed launches. And this was also the time when I started offering social media management, and the rest is kind of history. By history, I mean, literally two episodes ago, I walked through my whole journey of how this side hustle of LinkedIn profile optimization turned into a full-blown marketing agency.
[00:25:11] And here we are today, right? Looking back, I wouldn't say I had a successful launch, I guess, other than social media marketing, but it wasn't really a launch. I didn't like to launch anything; I was just gaining some traction on Fiverr, and I signed a couple of clients by reaching out to people that I knew.
[00:25:30] Outside of social media management, I've had exactly one successful launch in my business, I would say, and it was my Fiverr masterclass. That I launched earlier this year. So literally, it wasn't till year four of my business that I had a launch that I felt like went really well. I think I had over 20 people sign up for the masterclass when I first launched it. I've had more people continue to sign up since then because it's still something that you can sign up for. And I talk about it on TikTok a lot, but that was something that, looking back, I almost couldn't even tell you what made it so successful because there wasn't a ton of strategy behind it.
[00:26:17] But I did know that I had a lot of people in my audience asking me about how to get started on Fiverr, so I did know it was something that people wanted, that they were asking for. And it was just something that I felt like I needed to create. It was like it needed to be birthed out of me. I wish I could show you guys the note.
[00:26:36] I remember having a note on my phone with all the different things I wanted to include in the masterclass, and I had so many ideas for content to create to help promote it, and I think a lot of my content. I showed up with such good energy, and I had so much belief behind this masterclass that I think that just really came across in my content and allowed people to really see me as an expert and an authority and like, oh, she knows what she's talking about.
[00:27:08] And I had the testimonials because I had already helped some of my clients get started on Fiverr. And I had my results to show for it, so I think having all of that social proof and just how I was showing up and talking about it. Literally every single day, I was on Instagram, I was on TikTok, I was on my stories, I was talking about it, and it went so well.
[00:27:27] I'm so happy with how that launch turned out. It wasn't easy, though, because I literally remember a couple of days into that launch, I started spiraling, and it was like, the thoughts in the back of my mind were like, "no one's gonna sign up," which wasn't true, because I literally already had signups at that point is usually, it's kind of rare to get signups the very first day of a launch, but It doesn't matter, because, the trauma of all the failed launches from the past came back up, and I literally had to sit down, breathe, journal, work through every single negative thought that came up, and change the story that was playing in my mind so that I could keep going with that launch, and I'm so fucking glad I did.
[00:28:11] It can be so hard when you've tried something, and it didn't work, and especially if you've tried multiple things that didn't work, for you to not just keep playing that story in your head every time you try to create something else. And it can be so hard to even have the motivation to launch something else when everything you've tried in the past hasn't worked.
[00:28:33] But I... I'm a stubborn bitch. And I just, I knew that there was going to be something that would eventually click, and I wasn't going to stop until I figured out what that was. No matter how many things I tried, that didn't work. I just knew I had to keep going. And that's really the moral of this story because I could have used any of these moments where a client backed out, where I didn't know I was going to pay my bills, where I launched something and it, and no one signed up, and then I launched something else, and no one signed up and then I tried, you know, I, I mean, I was promoting my membership for well over a year and I never had more than like, I don't know if more than ten people ever signed up for that. It was exhausting because I would try to run a sale on it every month, and then maybe one person would sign up.
[00:29:27] So I was constantly in a state of this isn't working. Everything I tried was not working. All the evidence on my face was telling me this is not gonna work. And yet I kept going. I didn't choose to see any of that as failure. I didn't make any of that mean that I wasn't cut out for entrepreneurship, but I easily could have. I could have just looked at all that shit and decided, "This isn't working. And I should just go back and get a real job." Quote: real job. But I need you to hear this. The only reason why my business didn't fail was because I kept going. Is because I chose not to label all of those things as failures. And every time that I was knocked down, I made a conscious choice to keep going despite all the evidence in my face telling me it wasn't going to work.
[00:30:24] Do you get that? It's a choice for you to view whatever has happened as a failure or just a temporary setback. You're the one who decides that you're the one who gives meaning to these situations. You're the one who gives meaning when you launch something and no one signs up, and you can choose to make it mean that you suck and you're not cut out for entrepreneurship, and no one wants what you're selling, and it's never gonna work, and you have to go back to a nine to five, or you can choose to make it mean that it's just a temporary setback, it's a learning opportunity, it's just you see an example of what doesn't work so that you're getting one step closer to what does work. What's that quote? Isn't it like Thomas Edison tried 10,000 different ways until he finally figured out how to make a light bulb or make electricity work?
[00:31:23] And he's like, I didn't fail. I just found 10,000 ways not to make a lightbulb. Do you get that at any one of those 10,000 attempts he could have thrown in the towel and he could have decided I'm never going to figure this out, but he didn't. He just kept going. The only way you can fail is if you stop trying.
[00:31:40] Because if you keep going, you're eventually going to figure it out. So the only difference between someone whose business fails and someone whose business succeeds is that the person who succeeds didn't give up. The only way your business can fail is if you decide it does. So, I hope that this message reaches whoever needs to hear it right now.
[00:32:03] I know that it was something I needed to hear many times, and I just never want to forget where I came from, I never want to forget what this journey has been like, and where I started, and where I am now, and where I'm gonna be next year, or five years, or ten years from now. But I also would never want someone to look at where I am now, and feel like they are behind, or feel like they can never do that, or I think it's easy to assume that it was somehow easy for me, and I didn't have the same, setbacks or bad days or bad weeks or months where I didn't know how I was going to pay my bills.
[00:32:43] Like, no, I, I will be the first one to remind you that there were many months in my business where I didn't know how I was going to pay my rent. And I just want you to know that if I can do it, you can too. And it's just a matter of persevering through all of the shit until you find what clicks and you find what works for you.
[00:33:04] And it's so worth it on the other side. So. I love you. Thank you for listening. Thank you for being here. Keep showing up for yourself. You absolutely, 100 percent can do it, and I have no doubt in my mind about that. I love you. I appreciate you. I am here for you always. I will talk to you in the next Unhinged episode.