Episode 108

Leaving the Day Job

January 24, 2017

Is it time to leave your day job? Today we’re talking to all our bosses who are side hustling their business while working the day job. We’re sharing our tips for how to get in the right mindset, develop the right habits and routines, get your money in order, and create an action plan to actually take the leap and take your side hustle full time.

Learn More about the Topics Discussed in this Episode
This Episode Brought to You By:
"Make the plan, do the work, get there. Then decide if you want to leave your day job or not."
- Emily Thompson

Discussed in this Episode

  • Our experiences with leaving day jobs
  • The mindset shift of going from employee to your own boss
  • Developing habits + routines to set yourself up for leaving your day job
  • Creating boundaries around your day job and side hustle
  • Getting your money in line to leave your day job
  • Leaning on your family + creative community for support
  • Creating an action plan for leaving your day job


More from Kathleen

Braid Creative

More from Emily

Almanac Supply Co.


Kathleen Shannon 0:01
Hello, and welcome to being boss,

Emily Thompson 0:04
a podcast for creative entrepreneurs. I'm Emily Thompson.

Kathleen Shannon 0:07
And I'm Kathleen Shannon. All right, today we are talking about leaving your day job. As always, you can find all the tools, books and links we reference on the show notes at WWW dot being boss club. So we've got a lot of bosses listening in that are still working day jobs. And this might just be the year to leave that day job. So today Emily and I are going to be chatting all about what it takes to make the leap. Hey, guys, I want to pause here and tell you if you have a creative side hustle or if you're thinking about leaving your day job. Or even if you just want to get more organized with your money, and you've already been working for yourself for a while. My biggest recommendation is to use fresh books cloud accounting freshbooks is an easy to use software designed exactly for you as a creative entrepreneur. It makes tracking your expenses super easy. It makes setting up invoices and billing clients super easy. You can track your time, you can put together estimates, the software is super duper robust, but incredibly intuitive and easy to use. So you can try it for free today by going to www dot freshbooks comm slash being boss and enter being boss in the How did you hear about us section? Alright, back to our show.

Unknown Speaker 1:44

Emily Thompson 1:46
I'm excited about this one. So I pitched this episode to Kathleen a couple of weeks ago, whenever I was at a local, a local meetup thing. And this really adorable girl was sitting across the table from me and I was asking her what she does. And she has. Heather has a product business monogramming things for people doing some personalization. And then she also has a day job at a like retail store as a manager. And she was like, Yes, I'm working on, you know, leaving my day job and pursuing my side hustle full time. I've been doing it for a couple of years. And I was like, Alright, what's your exit strategy? And she goes, huh? And I was like, do you have a plan for leaving your day job? And she was like, Well, no. And I was like, Well, shit, it's time to do an episode about this. Because if you want to leave your day job and make your side hustle, I think you have to have a plan for a year happen. So Kathleen and I have put together some of our best notes and tips and experiences to talk about how it is that you actually make the leap from day job with a side hustle to full time. Creative.

Kathleen Shannon 3:00
Yeah, so let's start with sharing a little bit of our stories and backgrounds with working day jobs, and then leaving those day jobs to work for ourselves. So Emily, what was your experience? Like?

Emily Thompson 3:11
Right, I'll do mine first because mine's ridiculous. Um, I was pregnant a couple years ago. And I was working as an assistant manager at a retail store at like a he has a mall store. We weren't in the mall. But there were these stores in the mall. And my manager was a bit of an ass. Just ongoing always was I was probably five months pregnant. And I had a customer come in and requested that I get get a lamp because it was a home decor store, get a lamp from the back room for her. Or she wanted it and she needed it from the back room. And so I went to my manager, a dude a burly man, and asked him to go get this lamp this large lamp out of the stockroom because it was up on a big shelf. And I should not have been getting it myself and he wouldn't do it. So I take my pregnant ask to the back room and I get on ladder and I get the lamp and I get it down. And I handed it to the customer and she goes did you go get that by yourself. And I was the guest name I did. And she was so angry because my manager was just sitting up at the front desk just hanging out chit chatting being usual as self. Um, and so I walked over to him. And I handed him my keys and I was like, I'm going and he was like you going to lunch? And I was like, No, I'm going for good. And I left and I never came back. So for me it was pregnant hormones and just having had enough of an asshole boss. That made me take the leap and so I took the leap. I went home I did lots of creative things for a while. I sewed Lily's first diaper bag, and I did some scrapbooking and I started making jewelry and at that point, my first career A business endeavor was born. So I totally took the leap out of my full time job. I actually don't think I was quite full time. But maybe it was I don't remember, it was a really long time ago, out of my job, and just cold turkey leaped into creative freedom. And it was frightening, so frightening, but, but necessary for me at that time, and I have not looked back at all. So that for me was my crazy story of the last time I was employed by someone else. And how I left it. He What about you.

Kathleen Shannon 5:37
Um, so my day job was working as a senior art director in an advertising agency. So I was very much doing what I was wanting to do for a living, I was just doing it for someone else, rather than doing it for myself. And I never really thought about working for myself, I don't come from a family of entrepreneurs. And we all love having someone else pay our health insurance and taxes and pensions and all those things. So it just wasn't in my family culture, or it really even in my friend group to be a creative entrepreneur. I wasn't listening to podcasts or reading blogs about working for yourself, it was just a totally new thing. But I started getting the itch to work for myself, after I had published and posted on my blog, which I had been blogging a lot of the time, but I published on my blog, my wedding invitation designs, I had just married my husband. And whenever I publish those wedding invitations, they got a lot of attention. And I started attracting a lot of other like minded brides and creatives who were really interested in me designing their wedding invitations. So that kind of sparked this, working on the side side hustle, it was a total accident. And in the evenings, I would come home and work on wedding invitations that were really fun. And what I loved about it is that I was working in advertising, most of my design work was going toward my biggest accounts were working on credit unions and small local bank accounts, which was fine, but not really like my cup of tea. whenever it comes to using my talents. I did love. I was a senior art director for the NBA Hornets whenever they had come up from Hurricane Katrina to Oklahoma City, and I loved working on that account. So I was working on really fun projects. But what I loved about designing wedding invitations on the side is that I could just be creative and design for design sake. And there was no admin involved. Like it felt very much like I was just doing the creative stuff. I wasn't super bogged down with creating a business out of it quite yet. Anyway, eventually, I started getting enough of this side business, I did have to start thinking like an entrepreneur, I did have to start balancing how much I was charging with how much time I actually had to do these side projects. And at the same time, I was becoming increasingly unhappy at my job in advertising. And I think it's because the advertising market in general was changing and crashing. And there's a lot of stuff in the economy going down. And then even with the growth of the internet and social media, advertising just isn't what it used to be. So there's a big shift happening. And I felt like I wanted to jump ship. So I had enough work on this side that my husband really encouraged me to go ahead and make the leap. And I'll get more into like all the nitty gritty that went into my decision making process. But it was a really big deal for me. And it was super scary. But I think what really got me through a lot of it was blogging about it and sharing my experience as I went. And that's kind of what I don't think that being boss would be here today if I wasn't into sharing that process as I went. So that's kind of my story. And yeah, I was super freaked out. I was afraid that like what would people think? And who am I if I'm not a senior art director winning all these addys? Does my work even matter? Yeah. So for me, I think it was just a really big mindset shift versus a physical shift, if that makes sense.

Emily Thompson 9:31
Definitely. And I also want to bring up how you and I have both also recently left another kind of j day job for a side hustle. And that was leaving the one on one work that we were doing with our clients, which for us was very much like day job like it was paying our bills. It was all working the way it was supposed to but we had this itch to go do something else. And so we both did step away from one on one client work within the past year which for us was the day job. To do this side hustle, which was at podcasting, but then also for both of us some digital product. So I think that I think that's a fun little switch to where maybe even if you're, you are working for yourself. But if you're doing some one on one work, and you see yourself not maybe doing that anymore, or just transitioning your place in your business in a very dramatic way that makes you feel like the similar feelings of taking a leap to leave your day job to do a side hustle, I think, I think we can speak pretty knowledgeably to all of those facets of do yeah,

Kathleen Shannon 10:37
we were just kind of catching up on this last week, like our strategies as far as leaving the kind of work that we were doing, because braid creative still takes on one on one client work. And I still get a paycheck from braid creative for that one on one client work. Whereas you had to shift your model a little bit differently, because I know that you've tried the team within the shop biography, and it just didn't work out for you. So you kind of shifted in a little bit of a different way.

Unknown Speaker 11:06

Kathleen Shannon 11:06
there's a lot that goes into that

Emily Thompson 11:09
so much, so much. So over the next little bit, we hope to dive into, I guess, really just kind of the surface of this decision for anyone, because there are so many options for taking the leap. And it all depends on the kind of business, you are running your role within that business, what you're leaving behind and what you're going towards so many things. But I think that I think that we have some nuggets, we'll see how well they come out.

Kathleen Shannon 11:37
All right, I want to talk about mindset whenever it comes to leaving a day job. So I mentioned in my experience, this was a huge shift for me. And I really struggled with getting in the mindset of becoming an entrepreneur, going from being a star employee, to being my own boss. So I think the biggest mindset shift I really had to make was really identifying and acknowledging that even day jobs are uncertain, no matter how safe they feel. And especially since becoming my own boss, I realized that my CEO at the advertising agency, within the same position that I'm in now, and I found all this comfort in him as my leader, when he was probably flipping out behind the scenes not knowing where our next account was going to come from, or how he was going to sustain all that business. So I just think that it's really important to understand that nothing is certain. And any certainty that you feel in a day job is just an illusion.

Emily Thompson 12:49
Amen to that. Oh, right, I feel is every time, every time I'm talking to a neighbor who's like hating their job, because they're working like 40 hours, 40 plus hours a week for someone who doesn't give two shits, like, and they're like, oh, but I'm doing it because like, I know, I have a job, like, do you. On the surface, maybe you have the illusion of knowing you have a job, but no one's place is certain anywhere. And I think that is really huge, especially in today's society. And like today's economy, especially, you don't know that like that's a false sense of security. And though I helps people sleep every single night, I don't think it's enough to it's not enough to keep me anywhere, for sure. For me, mindset comes in the shift of understanding responsibility. I think that I actually every single time I run across someone who, who thinks they can do the entrepreneurial thing I do like little evaluation of whether or not they can actually hack the responsibility. Because because there is so much responsibility that goes into doing your own thing. It's you are then responsible for your own taxes, your licensing, making sure your business is up to snuff all of those things so that you can so that you can legally be operating. But also, you know, if you mess up with a client or a customer, you don't have an HR team to hand them off to like you are responsible for the happiness of everyone. Or if you're the one taking on the client or the employees, excuse me. If you're the one taking on the employees, then you are now responsible not only for your livelihood, but in lots of ways the livelihood of the people that you employ. So for me entrepreneurship or taking the leap. It's not just getting a job or you're the boss, it's you accepting the full spectrum of responsibility that comes from deciding to be your own boss. And I think that I think that all too often that's glossed over a little bit I think of I think of people who take the leap too early on who think that they have it in them just to find out soon that they don't. Because

Kathleen Shannon 15:06
I didn't take into account all that stuff whenever I quit my job, like I was just not really concerned about the LLC or the taxes. And honestly, that's not really the mindset shift that I had to tackle. And I know that a lot of people do. But mine was really just no one around me as doing this, I felt like I was forging an entirely new path whenever it came to my friends and family. And I will say, though, that you can start getting in the mindset of an entrepreneur, even at your day job. So in some ways, I really was prepared because in the life of a job at my agency that I was working at, I was, I was in a lot of those client meetings. So I got to see a lot of what a marketing plan looks like and developing out a campaign looks like and developing out a promotional campaign versus a branding campaign.

Emily Thompson 16:04
So I really started to get those tasks off to you. Good, sounds good, you go.

Kathleen Shannon 16:14
But also, I was trafficking the job. So I know that, you know, you actually handle a lot of that here at being boss for us, Emily, but I was doing a lot of that on my day job. And I was doing a lot of that at braid creative. And whenever I was working for myself as a freelancer, so I definitely have a lot of experience in that. But I was also tracking my time, which I think is why I'm allergic to it now because it was my least favorite part of my job working at an ad agency. And I was also working on billing clients, I remember one time I made a $15,000 mistake, I made out agency, and I got sick to my stomach over it. And I vowed to recoup that expense. And I really didn't have to. And in the grand scheme of things, looking back at it now, $15,000 probably was not a lot of money for my agency. But I really did feel responsible. So that weight of responsibility that you're talking about, I felt that at my day job, and I feel like that really did prepare me to become a creative entrepreneur. But another thing I think you really need to be responsible for. And the thing that I'm asking creatives to really see if they can hack it is if they have a point of view. So I think that it's so important to get in the mindset of understanding what it is you want to be an expert in? What is it that you want to be known for? And in what ways can you become what you want to be known for within the context of a day job. So we're gonna get into step by step how to leave your day job. But I think one of the most important things is, if you are not working at a day job that supports the expertise that you want to be known for, go ahead and try and find a different day job. Try and find something that is going to creatively fuel your fire and help you learn the skills that you need to know to eventually work for yourself. I think that that's huge whenever it comes to getting in the right mindset and really preparing to leave a day job.

Emily Thompson 18:15
Yeah, I think creatively, that's really huge. But for me, the mindset that I would like to challenge everyone to cultivate in line with the responsibility is to go ahead and start thinking of yourself as the entrepreneur. For a lot of us the creativity part comes really easy. And especially if you're in a job where you are already having that cultivated in you, the entrepreneur, side of your of that personality is what you need to start cultivating, as well. So for me, it's thinking of yourself as a is to go ahead and start thinking of yourself as a working for yourself entrepreneur and think about how that affects the life that you're living now, are you maybe saving a little bit more or spending a little less freely? Or maybe not? Are you maybe waking up earlier because you know that you have more things that you personally are responsible for. For me, it's all about treating your day job as the temporary thing. And really building the weight and the foundation into the creative entrepreneur side of what you want to do. Because your passions do lie elsewhere. So start shifting the weight of who you are, from your day job to your side hustle slash creative entrepreneurship and see what that feels like. Because as you do it, that will start being the thing that feels more real, you'll find less comfort and the comfortable day job and more comfort in the side hustle because you are pushing all over your energy into that space.

Kathleen Shannon 19:46
Okay, I want to talk a little bit about developing habits and routines to set yourself up for leaving your day job. So I think this is the thing that we get asked about most How do I carve out Time to work on my side hustle, even whenever I'm working my day job, and then especially if you have a family or kids or animals that you have to take care of on top of all of that. It's a lot. So Emily, what do you think here,

Emily Thompson 20:15
I think you have to treat this as a day job. It's just here, your day job doesn't start until 6pm, or maybe only on Saturdays, or whatever it is. But for me, it's about creating structure around the time that you do have to work on your side hustle. So if you are doing it every like Monday, Wednesday and Friday at 6pm, then know what you're doing at 6pm. So you sit down, you answer your emails, you write a blog post, and you get into the client or in customer work, or whatever it may be having that structure of building yourself a work day, even if it's at a weird, unorthodox time or day, can give you a ton of structure and stability and knowing that the work that you are trying to get done will get done. And you're treating it with that sort of respect and responsibility that comes from you depending on this part of your life for future growth, whether that be in creative fulfillment, or in financial security. So for me, it really is creating for yourself a work day, knowing when every single week you're going to be working in what that work looks like building that structure. creating those those habits around sitting down and doing the work for yourself, is how you start treating this thing like it's real.

Kathleen Shannon 21:33
Yeah, I'm trying to remember back to how I was doing it when I was working a day job and then designing my invitations on the side. But even more than designing on the side, I was blogging every single day, and back then sometimes twice a day. So what I would do, and granted, I didn't have a family back then I was newly married. But I felt like I had a lot more free time than I do now. But I would wake up early. And I would go into work early, I worked in a creative environment that I loved blogging from my desk at work, and I had a lot of freedom and flexibility there as far as Internet sites not being blocked. So I would grab my coffee, and I would write a post in the morning. And then sometimes I would maybe finish it up at lunch from my desk. So if you have the opportunity to do some of your side hustle from your day job, you should totally do that. Bosses everywhere can kill me for saying that

Emily Thompson 22:33
during your lunch hour when your time is your own. I feel like that is nothing wrong with that. And I think of all the all the bosses who've, like visited our webinars and like at work, no one's watching, we know who you are. It's fine.

Kathleen Shannon 22:47
I was but I had a lot of habits and routines in place. So I would do that every single day. And I would only maybe spend 30 minutes in the morning and an hour at lunch on it. And it was really no big deal. And I was able to get a lot done in that time. So that's one thing I want to make sure that you all know is that you can get a lot more done in a little bit of time than you give yourself credit for. So set a timer for maybe 30 minutes, do anything that you can do in that 30 minutes. But I want it to really fuel your creative genius. And not be like excuses for procrastination, like I need to get this thing set up, I need to look into how to set up an LLC, that is not a good use of your time, make sure that you are using your time to work on your core genius.

Emily Thompson 23:36
Agreed. And the thing I want to follow that up with is is another mindset shift around this like you are choosing to work more like you could just hang out in your day job and get your paycheck and everything will be fine and good. But you're choosing to do something more with your life. You're choosing to work extra you're choosing to spend your evenings or your weekends doing work that's fulfilling, do you be happy about it? I think that it will not fuel you in any way. Nor will you create anything that you're super proud of. If you're going into this with it with super procrastinating mindset or if you're annoyed that you're having to work more like whenever I hear people like pissed off that they have to like leave their day job to go pursue anything that they want to pursue. You're not going to love it like just stop. So that is a mindset shift. I'm going to encourage everyone to grasp a hold of I think of whenever you and I were starting being boss, if we had showed up for every recording angry that we were fitting another recording into our week, this would not have gone very far. So be happy about this, this, the side hustle that you were you are trying to grow because that energy will feed into so much more than just in the moment activities, but really the ability that you have to grow the side business. You know, this

Kathleen Shannon 24:58
is a really good point too. I didn't want to leave my day job angry. And I know that anger fuels a lot of people's decisions to leave their day jobs. But I think that if you're already working, it's kind of like, um, before you break up with someone, you want to just villainize them as much as possible, but what would it be like to leave your day job out of happiness and excitement for the side hustle that you're going to create. And so I along with being happy about working extra, because you're trying to build your hustle on the side, I think that if you can try and create really solid habits and routines, and a mindset around your day job that comes from a place of happiness, and productivity and efficiency, it's only going to help your side hustle, be that much more efficient, and happy. And all the things. So I think that this also takes us into boundaries, I want to talk about creating boundaries around the day job and around the side hustle to be a happier creative person. What do you think about this one, Emily.

Emily Thompson 26:11
So I have to, first of which is you have to still have a life, like you have chosen to work double at this point, which is for a greater good, both for you personally, but also probably for your family, and maybe even for the world as a whole, which I think is really important. But you have to still take care of yourself. So for me very strong boundaries around giving your site yourself permission and time to have a life. So whether that's having one day where you're not working on anything, like having a legit weekend day, I think is a super powerful thing. Or, or if you can't do that, then having one day where you are only working one of those jobs is really important. So for me, one of those boundaries is around taking care of yourself. And structuring your business and your day job in a way that gives you the freedom to maintain that life. And remember, you'll have more of a back once you quit the day job. And another boundary for me is picking a date. Knowing that you have this end date in sight. It's on your calendar as the day you're leaving your day job for me, that creates a very strong boundary around when you have to reach whatever level of success you need to be able to quit your day job. So maybe open up a calendar right now, pick a date, X number of months into the future and say this is the day that I put in my notice. So that you have a boundary within which do make the money book the client, sell the products, grow the team or structure the thing so that you are able to actually leave Otherwise, you'll be like that girl who has been side hustling for years and had never even thought about when she would leave her day job.

Unknown Speaker 28:02
What about you, Kathleen,

Kathleen Shannon 28:05
I see a lot of people working overtime and giving their day jobs, so much more energy than is actually required of themselves or of the job. I feel like these are people who are especially set up to be creative entrepreneurs, they already have that work ethic, and they're pouring it into their day job instead of into themselves. So I just want to remind everyone here that you can create boundaries around your day job where you're only working 40 hours a week, that is legally all that is required of you. Now I know that culturally or even like as far as the company culture goes, or even your own self drive to be the best might keep you at work more than 40 hours a week but you don't have to.

Emily Thompson 28:54
So you're a taxing comes into play. Like you can certainly I think of one poor person I know right now who works so much. And and like they'll ask him to come in on the most ridiculous days and He'll do it. And I'm just like, one, don't talk to me. Like I don't even want to hear you argue or be sad about it or whatever. Because you're choosing to say yes, but I do. I feel like I'm just ranting now I'm so mad about that. Um, what was I saying?

Kathleen Shannon 29:21
I was saying something good that your friend goes in extra. And they don't have to. Right? I mean, could they say no? Do you think that they would get fired? If they said no. And then maybe it's not such a bad thing?

Emily Thompson 29:35
Right? Oh, I know. So anyway, so yes, I think around around your day job creating boundaries because you're choosing to do something else. You're choosing to start stepping away to make your side hustle a thing. So do that by giving your day job more and more of yourself and not gradually stepping back, which I think is a great tactic. We've talked to people who were working 4040 plus hours a week at a day job. And started having the conversation even that they were wanting to leave. And so it went down to 30. And then it went down to 25. And then 20 until they were able to, to wholeheartedly leave. So if you're in a place where that relationship is a possibility, I don't think it's a, it's a bad, bad way to do it. But make your priority your side hustle. If you want your side hustle to become your main gig.

Kathleen Shannon 30:27
I will say that whenever I was working as a senior art director at an advertising agency, that job was my priority. It was definitely my priority over doing freelance wedding invitations on the side. It was 100% my career and my expertise and what I wanted to be known for, but I wasn't willing to work more than 40 hours a week, and I wasn't impressed by people who were working more than 40 hours a week, because more than anything, it just showed me that they weren't being very efficient with their time. So if I found myself working more than 40 hours a week, which was very rare, it was an exception and not a rule. And if I was consistently finding that I was having to put in 125%. In my day job, I was going to my boss and saying, We need more help. And I think that's kind of an entrepreneurial mindset, when you can recognize that you are doing too much and that this is inefficient. I think that day jobs, you can put a lot of systems and processes in place. And don't wait for your boss to do it for you. Again, this is about getting in the entrepreneurial mindset. If you can set up systems and processes and habits and routines and boundaries in your day job that help you work 40 hours a week, you are doing your entire company a favor, and you're doing your future entrepreneurial self favor as well, because you're basically training yourself how to work like a boss. And I will also say while working a day job only do work that you want to be known for on the side, I see a lot of creatives trying to hustle their worth by taking on anything they can on this side. I'm just to prove that they can do it. But then they're taking on a lot of work that doesn't really fit into what they want to be known for. And you'll be tempted to do this because you want to prove to yourself that you can do it. But if it doesn't count toward your portfolio, and I use that word loosely like obviously for graphic designer, your portfolio could be a very literal thing but for let's say a coach, if you're taking on a coaching project, that is not what you want to be coaching around. Don't do it.

Unknown Speaker 32:41

Kathleen Shannon 32:43
All right, let's talk about money. Right? Whenever we interviewed our friend barrel on episode number 90, I got a really specific with her because I really wanted to know exactly how much money she needed to feel comfortable leaving her day job. And our friend barrel. If you haven't listened to this episode, be sure to listen to it. It's episode number 90. And she spent three years hustling it out on the side before she left her day job as a teacher. So I think that money is a huge aspect and a big part of understanding what you need to do to leave your day job. So for me, I think that you need to be 50% there with a side hustle. So let's say I was making $30,000 a year as an art director, I wanted to be bringing in a projected $15,000 a year with my side hustle before I felt comfortable making the leap. So I think that if you can bring in enough money that you're at 50% of what you're making to survive, then you can trust that whenever you leap and you have an extra 40 hours a week to dedicate to your creative career, you'll be able to pull more resources resources being time to bringing in the rest of that income required. What do you think about money and how much you need to stock away? I mean, you hadn't? You had nothing right whenever you quit?

Emily Thompson 34:07
No, I didn't think about numbers at all. I was just fueled by pregnant hormones and was done which worked out fine. Um, so but now I would definitely go about it much, much more smartly. So I think about whenever we decided to stop doing one on one projects to move into digital products and for focusing on being boss, and David and I sat down and got very clear about our numbers in terms of how much do we really need every month to survive. If we were going to be cutting off, you know, 150 $200,000 of revenue a year by doing away with one on ones like if we needed to get down to two like the bones of what we need to survive, what do we need, and with how much projects we have left, like how much of your day job you have left, how much more Can we save? What do I need to do to be creating the thing to get me to, you know, completely comfortably leaving one on one projects to go into digital products? So we just got really clear on our numbers, how much do we need? How much? How much do I need to make, and how long have a how long of what is it called, like a grace period Do I have before I need to start busting shit out. So we just got really clear on our numbers. We knew what they all were, we knew how much money we had the bank, we knew how much money I had coming, we knew how much money I would be making in some future projects and was able to, to know how long we would feel comfortable before we'd have to maybe go back to the day job, which was one on one projects. And I think that's another mindset shift, I want to encourage everyone to take as well is this idea of whenever you leave your day job, if you take the leap, that's not the last day job you'll ever have. If it goes to shit, and you have no other choice, you can go get another job. I think all too often people fear leaving the job because they think they'll never get another one. They fear if they leave it, if they take the leap and do the side hustle, and it doesn't work. They're just left homeless. And that's not the case. Chances are, especially if you leave that day job with relationships still intact, you will be able to get a day job again, if you ever so need for me hustled shut out, didn't need to do it. But maybe we're still in that little grace period, we'll see.

Kathleen Shannon 36:36
I will say our day job that I worked at and that my sister worked at, ended up hiring us for contract and we ended up working with them a little bit more to help them with projects moving forward. So that's totally an opportunity. And I also want to say that so many more business models, like even even day jobs are going toward hiring contract creatives versus full time employees. So I think that the way the world is going is that more and more people are going to be independent contractors and freelancers and small business owners versus the traditional employee employer model. So this is I mean, I think it's kind of a hopeful thing. For those of you who don't come from a family of entrepreneurs, like neither of us do, that you're not alone. There are a lot of people in this with you. Which brings us to the next step of leaving your day job, which is really cultivating your creative Wolfpack and your business besties and the people that will make you feel less alone in the process.

Emily Thompson 37:43
Amen to that I think of whenever I did start, did start selling my creativity as a creative entrepreneur. It was definitely the Etsy community for me that really gave me so much. So much like fuel for my fire to keep going knowing that other people were in it with me that I had someone there to answer questions about payment processors, or photos or naming or product descriptions, or whatever it was like having, knowing that you have people in it with you is really, really powerful for for taking such a big scary leap. And I also have to have to like have a moment of gratitude around my family. And the people who support like my friends and family, the people who support me, have always supported me in my decision to be a creative entrepreneur. And granted, I don't think I would have given them a choice otherwise. But that has been really helpful to have a partner who's totally in it with me, or even to have parents and friends who don't question it too much. Just smile and wish me the best is a really powerful thing. And that for me is also my tribe, in terms of having people who support me, for me, friends and family have been super, super impactful, but also this larger tribe of internet people who were in it with me just chugging along right there alongside me it does wonders for knowing that you're not in this by yourself. Yeah,

Kathleen Shannon 39:14
whenever I quit my day job, my sister was actually my boss and my creative director. And so that made it also really personal because we were a family business before we were working for ourselves. And before we had gone into creating breed creative together. So it was really scary for me to go to her as my boss and say, I think I need to leave. And I really needed kind of her as my permission giver to help me fly the coop. And so that was really huge for me getting the support of my sister who was also my boss to leave. But then beyond that getting support from my family was definitely huge. And we've been asked by creatives, what do you do whenever your family doesn't support you? I think it's really just recognizing that they are scared, they are putting themselves in your shoes, and they're scared thinking about what they would do. So I think the biggest thing that you can do if your family and friends aren't on board is helped make them a part of the process. Let them know what you're into. This is why I love blogging my journey, because in some ways, I was able to craft the narrative of becoming a freelancer and small business owner, I was able to share the parts of it that I wanted to share the struggles and victories alike, and then really invite dialogue and conversation from there. So I think it was really kind of exciting for my family to see it unfold as a story. So I would recommend sending out almost like a weekly email or newsletter to your friends and family of what your journey is like. And I mean, maybe some family and friends would be like, Can you take me off this list? So maybe just once a month? I don't know. But I think that you can really get out of the box in how you share with your friends and family to get them on your side. And but yeah, that's huge. And then also, for me, my internet friends was a huge part of me becoming a creative entrepreneur. Because again, like I mentioned, even though I had the support of my friends and family, it was more like, they were just kind of watching from the sidelines me doing this big scary thing. Whereas my internet friends, a lot of them had been through it. And a lot of them could say, Hey, here's what this is like, you might try this, or Hey, I know you're struggling with this. Have you thought about doing this, and I just felt really in it with them. And also the thing that I love about the being boss clubhouse, which is our member, wolf pack that we have over at being boss. So if you guys want to check that out, if you're truly feeling lonely, and if you're gearing up to quit your day job and you've got a side hustle, that is a great way to get started. Just go to www dot being boss club slash clubhouse to learn more there. So yeah, your tribe is huge. It's everything. Relationships are everything. I'm learning this more and more.

Unknown Speaker 42:18

Emily Thompson 42:20
Alright, so let's go into action plan because go back to that girl scenario across for me, girlfriend wanting to leave her day job, but had no action plan. I would love for you, Kathleen to lay it out. What do people need to do to leave the day job to make their side hustle a full time thing.

Kathleen Shannon 42:42
Alright, if I was speaking to that woman, I would say First, make sure that you're working a job that gets you closer to what you actually want to be doing on your own. Or I love how Elizabeth Gilbert in Big Magic talks about your day job really funding the dream. And so really getting in the mindset there. Then next, I want you to get on the same page with your family and friends. And especially your partner. If you have one, you need to outline an action plan with them of how much money you need to have in savings, how much money you need to be pulling in with your side hustle before you can leave. It's really so so important that you define what those metrics are. So you know, whenever you've hit that point, I think also setting that boundary of that date. Like you mentioned, Emily, like, Okay, this is happening by this date, we'll put a little hustle in your bustle. And then you'll want to really get your side hustle set up as a business. So branding and website and a few clients or projects under your belt is huge. You can also start setting up your systems and processes now. Get that project management software in place, get fresh books, cloud accounting setup, do what you need to do to get as much stuff set up as possible so that whenever you make the leap, it's not as painful. And get your support system in place. So you've gotten on the same page with your family and friends and your partner. But also start looking into online support. You can join a Facebook group, you can join the being boss clubhouse, you can set up monthly dates with a business bestie who will help keep you accountable. You can also hire a coach who can help you get through this transition of day job to full time creative boss. And then finally, you've decided on your date. You've almost reached that date, give your job two to four weeks notice. Or if you're Emily, you can just leave before you just hand in the keys and say Nah, but it's very like it's just very practical and tactical and it's step by step. There's no there's no other way around it. So That's how I did it. And it worked. For me, it felt very scary and dramatic in the moment. Looking back, I mean, that was six years ago, it doesn't feel like a big deal at all anymore. But at the time, I remember I was a wreck like, I don't think I could eat. I was freaking out every other day about what this meant for me and for my future, and even my identity. And so for me, the biggest part was probably mindset stuff. So I definitely had to really pull on the support of my tribe and my friends and

Unknown Speaker 45:35
those things,

Emily Thompson 45:36
I think that's a good point that you make mindset was not obviously not something I ever struggled with, um, I had already owned a business at that point. So I already knew what it felt like to work for myself. And I think that's why it was so easy for me to leave someone that I didn't respect as a boss. For me, I think the biggest struggle, I guess at that moment, like I didn't even have a side hustle. Like, that's legit to guys. For me, it was really just setting up the business. And I think that, I think that's also something that too few people do whenever they think about taking the leap. Actually, maybe not too few. But I have absolutely seen it happen where people, they want to do this side hustle thing, or they want to make a side hustle their full time, but they haven't put in the work with their side hustle for it to support them yet, and they take the leap and they're lost. I also think that that problem is usually right alongside people who don't understand the responsibility in which they are jumping, they haven't done the responsible thing of actually setting up a business that's making the money yet. So the responsibility of their day to day processes is overwhelming. I think there are lots of things Kathleen and I just went through. plenty of options are plenty of places for you to focus on in taking the leap. Think about which one sort of stirs up the most anxiety for you? Is it the mindset Are you not sure if you are the boss who can do it, or maybe you know that you are, but your habits and routines are, are not in place yet. Whatever it may be, I think focus on the thing that that you're struggling with most of the moment and get her done, because there is tons of freedom and, and beauty and not waking up to an alarm clock. Those happy things that come from working for yourself, you are putting an energy into a side hustle, so make it worth it.

Kathleen Shannon 47:34
I also think anytime you're making a transition, it's really important to lean into it. So that is what my coach Jay Pryor always tells me whenever I'm making a big shift in my life or in my career, he says to lean into it. So almost like practicing or pretending as if you're going to leave even if you're not ready, I think about it as the time that I jumped out of a plane. I pretended as if I was not jumping out of that plane. But I went ahead and signed the waiver, I leaned into it, I went ahead and went through the training course, I went ahead and got in that plane and went up 10,000 feet in the air. But I knew that I could always not jump out of the plane. And then at the moment where I had to jump out of the plane I really didn't want to but I did. And it was fine. And that feels a lot like quitting the day job jumping out before analogy.

Emily Thompson 48:29
I love that.

Kathleen Shannon 48:31
I don't know that that was that great. But I loved it. I just had to lean into it.

Emily Thompson 48:37
Right? You can get all the way to the point. I think that's the key is do the work, like make the plan, do the work, get there. And you can decide then if you actually want to leave your day job or not. But you can't sit back not having made any plan and want to leave your day job. That's going to be a bit of a waste of energy.

Unknown Speaker 48:55

Unknown Speaker 48:57
There you go.

Kathleen Shannon 48:59
So you guys, I'm not the most tech savvy person when it comes to integrating and automating my life with software. So I was a late adopter to acuity scheduling, but once I set it up, I was so grateful and I cannot imagine my life without it. I use acuity scheduling to schedule client meetings, special projects, podcast recordings, interviews, and even coffee days with my friends. It helps me keep my calendar sane. The best part is it integrates with my Google Calendar. So anytime I update my Google calendar that time is automatically blocked off in acuity. There are no double bookings or meeting scheduled for when I'm on vacation or scheduled something else already Alright, try it yourself. Sign up for a free 60 day trial of scheduling sanity at acuity scheduling calm slash being boss. Thank you for listening to being boss. Find Articles show notes and downloads at WWW dot being boss club.

Emily Thompson 49:58
If you're a creative entrepreneur, freelance or small business owner who is ready to take your goals to the next level. Check out the being boss clubhouse, a two day online retreat, followed by a year of community support, monthly masterclasses book club secret episodes and optional in person retreats. Find more at www dot being boss club slash clubhouse.

Kathleen Shannon 50:21
Thank you so much to our team and sponsors who make being boss possible our sound engineer and web developer Corey winter. Our editorial director and content manager Caitlin green, our community manager and social media director Sharon Lee, and our bean counter David Austin, with support from braid creative and indicia biography.

Emily Thompson 50:39
Do the work. Be boss, and we'll see you next week.