134: Exploring Self Employment with Jenn Smith

Welcome back to Career Clarity Coach Jenn Smith! Jenn and I are talking about something that we don’t often talk about on the Career Clarity Show – self employment. So often, we are thinking about how to help people make a move from one corporate opportunity to another one, how to go from one day job to another day job. 

But there is another way to create a career for yourself. It’s one that I devoted a measly single chapter to in the Career Clarity Show book, but is a whole different future and life. And that is playing with the world of freelance and entrepreneurship. Jenn and I will be diving into questions like how to gain traction, the reality of being an entrepreneur, and more.

Want to learn more about our strategic framework for successful career change? Download The Roadmap to Career Fulfillment ebook right here!

Show Notes:

• Learn more about Jenn (and apply to work with her!) in her coaching profile
• Episode 20: The guide to creating a tenacity-driven career with Jenn Smith
• Episode 40: Monitoring and Managing Your Energy at Work with Career Clarity coach Jenn Smith
• Episode 54: Mastering the Top 5 Mental and Motivational Habits with Career Clarity certified coach Jenn Smith
• Episode 87: Tactical Tips for Marketing Yourself with Jenn Smith
• Episode 106: Practical Tips To Make Your Career Change Happen with Jenn Smith
• Episode 117: A Career Clarity Show Takeover with Career Clarity Coaches Jenn Smith and Kelley Shields
• Connect with Jenn on LinkedIn
• Follow Jenn on Instagram at @flourish.careers
• Roadmap to a Fulfilling Career eBook

Subscribe to The Career Clarity Show on Apple Podcasts, Stitcher, Spotify, and Google Play.

And, follow The Career Clarity Show on Facebook and Instagram — and sign up below to receive emails when new episodes come out!

Transcript

Lisa Lewis Miller  0:04   

Welcome to the Career Clarity Show. If you want to create a career path you’ll love, you’re in the right place. I’m Lisa Lewis Miller, career change coach, published author and your host. And each week, we’ll bring you personal transformation stories, advice and insights from experts about how you can find a more fulfilling, soulful and joyful career. Hello, and welcome back to the Career Clarity Show. I’m your host, Lisa Miller. And I’m delighted that you are with us today, because I’m delighted to have back on the podcast today. Our repeat guest, our Career Clarity Show certified coach, and complete delight, Jenn Smith.

Jenn Smith  0:48  

Ah, you are too kind. 

Lisa Lewis Miller  0:50  

Well, I am so happy to have you, Jenn. Because for our episode of the podcast today, we are talking about something that we don’t really talk about very often on the Career Clarity Show, because so often, when we are recording these resources for you, we are thinking about how to help people make a move from one corporate opportunity to another one, how to go from one day job to another day job. And you might be changing states, you might be changing industries, you might be changing roles, but you’re usually going from one state of employment to another state of employment. But there is another way to create a career for yourself. And it’s one that I devoted a measly single chapter to in the Career Clarity Show book, but is a whole different future and life. And that is playing with the world of freelance and entrepreneurship. And the association of freelancers or the National Freelancer union, whatever the trade association is, that represents freelancing individuals put out a study in 2017 that said that by 2027, they expected that 50% of the workforce was going to be freelancing, or have freelanced. So this idea of independent work and working for yourself, may be coming for you way more quickly than you might have imagined. Or you might be somebody who’s listening to this and thinking, actually, I have been secretly dreaming about entrepreneurship for years and years. But I haven’t known how to pick an idea how to make the leap. What I need to do to get traction, what even the reality is of being an entrepreneur or a small business owner, and going from all of these structures and supports that are provided by an employer, to having to do all of that problem solving myself. The any of these are questions that have caught your curiosity. Or maybe you’ve never actually thought about entrepreneurship for yourself. But now you’re a little bit curious what that would look like. Today’s episode of the podcast will definitely be for you. So Jenn, for us to dive into this juicy topic of ditching your day job, and exploring what self employment could look like. Tell me why you’re so excited about getting to record this as our podcast episode. Yes, thank

Jenn Smith  3:15  

you, Lisa. So I was very excited to talk about this topic, because it has been a theme in my client conversations recently. So with the shake up around the world with 2020, this idea of self employment or a side hustle or starting something as a passion project, or whatever it might be, has been a reoccurring theme. And I’m starting to get a lot of questions about, you know, how I went from a corporate job into self employment. And so I thought that it would be beneficial for you and I to share a little bit about our background and our story for all of our listeners to help them make decisions if that’s what they’re thinking about.

Lisa Lewis Miller  3:59  

Well, Jenn, I love the thoughtfulness and the generous pneus of your heart to want to create a resource for our listeners sharing our stories, because I think that you’re absolutely right, that when you’re contemplating entrepreneurship, sometimes it’s really helpful to have somebody else that you can point to and say, Oh, that’s how she did it. That’s how they created the financial runway they needed. Oh, that’s how they got market validation. So I love that we’ll both get to share our stories of entrepreneurship to give two potentially very different or potentially similar perspectives on ways to open that door and step into the world of self employment. And I guess the natural starting point would be with the question of if you were thinking about working for yourself, and you know, you like to do that, but you’re feeling a little overwhelmed or uncertain about What you want to do? For you, Jenn, how did you figure out where to start?

Jenn Smith  5:05  

Yes, I love this question because I thought about starting my own thing for years, for so long, but I just didn’t know where or how or what so. So I personally just started with resources. So reading and just kind of like figuring out what else what other people were doing to help me kind of get a good understanding or a framework in terms of what to start. And so one of the things that really resonated with me personally was Cal Newport talks about career capital, and talks about making a change in when you make a change, capitalize on the career path that you’ve already built, in order to make the most of that instead of just throwing something away that you’ve already built and starting completely new. So that concept really resonated with me, and my background in human resources, can, you know, be lots of different elements of you know, capitalizing on on the career that I had built. So starting with that kind of concept, and then narrowing that down a little bit further, especially for me listening to kind of like my intuition. So like, there was always this voice in my head, talking about like career shifts and career changes, and how many that I’ve actually made, and helping other people make those career transitions as well. And so, so kind of starting from there, I had a lot of other ideas as well. But I started with that, and then just kind of continued to play around with it. And there’s the the framework that iki guy, Japanese circle that talks about what you love, what the world needs, what you can be paid for, and what you’re good at, and it’s his diagram, and kind of the center of that is, is it. And so that’s kind of what I played around with and ended up coming to career coaching. And this was before career coaching was a thing. So it was a little bit unknown and a little bit scary. But that’s kind of where I started in and built it out from there. So how about you?

Lisa Lewis Miller  7:08  

Well, you know, what’s funny is I, I don’t think I’d ever come across Cal Newports concept of career capital and not throwing away everything that you’ve done before. But I. So I tried that in my previous life. Many moons ago, before I ever started career coaching, I was working in communications consulting, I was working in Washington, DC steps away from the White House and doing all this grassroots mobilization consulting work. And what I noticed was that there are things about the work that I really liked. But there are a lot of things about the work that I did not like. One of the biggest ones was that when you work for a very fancy pinkies out consulting firm that charges high prices, it limits you to a pretty specific subset of clientele. Right, it’s only the organizations that can fit the bill for the price that your organization has set. And a lot of those organizations were ones where I felt like they were not driven by a sense of purpose or mission or making the world a better place in a way that aligned with and resonated with my values. So I probably back in 2013, decided that I was going to start an LLC that was going to do communications consulting, for the little guys. For the underdogs, I was going to be consulting for nonprofits and schools and all of these heart centered organizations. And so I was, in a lot of ways leveraging my career capital there without even realizing that was the concept to say, Okay, let me take the skill set and the experience and the subject matter expertise that I bring to bear and just bring it over to some new and different clients that feel more exciting for me. And I ran after that business idea for a year. And it it was not successful, because I didn’t have any of the skills or the awareness of how to have a conversation with a prospective client, how to create a service package, how to price that, how to make sure that you are really meeting a market demand. And then how to kind of whip all that together into something that could be a viable business. One of the things that I learned from that first foray, and that failed experiment was that I needed to be solving problems for my clients that were big enough and painful enough for them to actually open up their wallets. And at that point, I was offering social media consulting for nonprofits. And at the time, I often joke that the beginning of my career I work did what was called New Media because the internet and having a website and having social media platforms and having an email list was all like very new and novel and shiny and weird. And the when you’re pitching social media to a nonprofit, they’re like, we can get an intern to do that, like, we will pay somebody $0 to do that work, that is not actually an important problem, to solve a problem that’s worth investing money and solving for them. So that was a, an entrepreneurial disaster. In my start. However, I learned a lot from that, about trying to find product market fit, right, so trying to offer a service to the world that the world really wants and needs and is willing to pay for. And that making sure that you get your pitch, right, and you know, the value of what you’re bringing to the table. And the marketing and the branding piece is so so important. So when I did my second launch into trying out entrepreneurship with this work in the career coaching world, after I got clear on what actually sparked joy for me, it started out small, and I started out working for free or low Bono, pro bono or low Bono to just gain more experience and get testimonials and get proof of concept. But I was able to learn from the things that didn’t work, the first time I tried entrepreneurship, to build a little bit more of a flywheel and build a little bit more momentum, and to notice my skill gaps, and upskill in those two years in between.

Jenn Smith  11:40  

Yeah, I love that you share that story about like, the missteps that led you to the actual thing that’s working, you know, so there it is a little bit of trial and error and a lot of different ways. And I think that, you know, when people are thinking about getting started into this world of self employment, like taking that first step is the scariest because of a potential failure. And, you know, trying to figure it out along the way, or making it perfect, and then never starting, like trying to get perfect, and then never starting so good for you for starting. And getting out there and then getting back on track. Well,

Lisa Lewis Miller  12:16  

let me also add a clarification, which I feel like it’s important to, when I did this, both times that I started businesses, I hadn’t ever quit my day job, I was working nine to five, or in the consulting world, it was more like eight to 630 every single day, and then trying to build the business in a couple hours a night on top of that. And so I was not in a situation where I’d put myself in any financial risk. I wasn’t in a position where this had to work out, or else. I was not loving what I was doing in my day job. And so it was bringing me a little bit more curiosity and growth and joy outside of work. But I went about it both times while maintaining a full time job in the interim. And by the way, I’m sure genuinely appreciate this checking in with my employment contract and with HR to make sure that there wasn’t a non compete or that I was being, you know, in compliance with whatever I had signed, to ensure that the way I was comforting myself, as I was building this business was not going to open me up for some sort of horrific potential lawsuit.

Jenn Smith  13:24  

Yeah, I mean that that’s important stuff to think about. But you know, as long as you’re getting in my opinion, my HR has long as you’re getting your day job done, and you’re not doing anything that’s gonna compete or complex, then what you do in your own time is what you do in your own time.

Lisa Lewis Miller  13:38  

Totally, totally. Well, so I kind of queued up a conversation about managing risk and thinking about the things that that you’re afraid of, because I know for me, I was really afraid of quitting my job in a rage, and then putting all my eggs into the entrepreneurial basket, and then not having it work out. And then being destitute. And I would sort of like catastrophize these things in my brain, I’m like, I’m going to be living under a bridge, and nobody’s going to be my friend anymore. And your brain can go to places that feel really extreme in fear. But I’m curious for you, what were some of the things that were popping up as fears and wonders and worries as you were tiptoeing into entrepreneurship.

Jenn Smith  14:23  

But yes, yes. And fear has that way of holding us back from things for sure. And so, you know, the biggest one I think a lot of people think about this is the biggest one that I thought about was the financial piece. And so, you know, just kind of really figuring out what that runway looks like. And I think you and I, from what I know about your story, I think you and I went about this a little bit differently, but, you know, just understanding what the runway is in terms of like your expenses and what you need to be bringing in what would be nice to be bringing in and having different layers of the financial aspect. So that was a big one for me, and I’ll tell you The way that I got over that was one talking with a financial advisor. So having someone take a look at all of my stuff and just say, like, you know, not that they’re going to tell me what to do, but just kind of give me the risks and the pros and cons about making the decision, which was really, really helpful. I didn’t want to rely on my husband for more, I wanted to make sure that I was still contributing in a way that was going to keep our lifestyle. And so that was a big, that was a big piece of it. And so once I talked to that financial advisor, it did help me kind of get over that big fear. The other fear that I hear from people and that I struggled with and I still struggle with is, what are other people going to think about, you know, you’ve got this great career trajectory in the corporate world, you’re working for really cool organizations, like, what are you thinking, you know, taking this leap of faith or taking this making this jump. And so I was really worried about that, especially like family, you know, I didn’t want them to be worried about me or anything like that. And so starting to have those conversations very gently over time. And I really, two things were very interesting. One is that the people that I was worried about, were more supportive than ever out of anybody, which was really awesome. And then when I really drill down to like, who are the people that I’m very concerned about, it was really just like one or two people that I was worried about judging me. And when it comes down to it, who cares about those one or two people, you know, like, in the grand scheme of things, they’re probably more worried about what they’re doing day to day than what I’m doing. So, you know, when I really thought about that, and it came down to those two people, I was like, this, this is easy. I can, I can totally move forward. You know, just thinking about that. So that’s kind of like those were kind of my two big theories and how I how I got over them. How about you?

Lisa Lewis Miller  16:59  

Well, you know, what’s funny is that that fear of what people will think, is one that our logical brains hardly ever register, like, Oh, that’s not a risk factor, blah, blah, blah, whatever. But oh, my gosh, it can have your emotional brain in a vise grip. And I remember when I was first learning how to do marketing, and to be visible, of this is what I am selling, this is what I’m doing. I would like to be compensated for this. I’m asking you for money to perform this service that was so confronting, and vulnerable and uncomfortable and gross. And I just had myself into this Tizzy about like, well, what, what is someone going to think? Like, Jenn, I didn’t even have the level of sophistication that you did, or being able to actually put my finger on who the person was who I thought was gonna judge me. It just felt like the world was going to judge me and the world was going to deem that I was an inferior life for him because I’m asking for money to do a service. And who did I think I was. And what was funny in my journey was that I probably didn’t get my first haterade about the work and being out there until maybe nine or 10 months in to running the business. And I remember it so clearly. But I got a message, an email from someone who I’d never met, who I’m not even sure I was connected with on LinkedIn, but who had seen a LinkedIn post of mine, and said, you come across as a wildly unprofessional no one in the Fortune 500 would ever hire you. Like, just wanted to give you the FYI. What. And I remember getting an email and not being able to sleep that night and feeling sick to my stomach. And then hitting a moment the next day where I was like, and if there are little ears listening to this, like maybe this is a good time to like pop your headphones in or, or pause the podcast. Like who the fact that you think you are, to reach out to me out of nowhere, and tell me that you think that I am unprofessional, and I’m never going to be able to work, then I’m a failure. It’s like who? Who must you think you are to give me this feedback to stoop so low as to correct me in the wrongs of my way. And what I learned in those 48 hours was I can survive this. I received a piece of hate mail. I mean, hate mail, sort of a strong way to phrase that one. I have gotten hate mail. Later, since in my career, that one maybe wasn’t hate mail, but I can receive disapproving feedback. and not die, I can receive that and get up the next day and continue to do good work for my clients. I don’t have to be everyone’s cup of tea. And in a lot of ways, that moment actually galvanized me in doubling down on some of the things in myself that make me stand out for, you know, for a reason, some people are gonna see as great and good, and some people are gonna see as problematic, like, using swear words, like talking about my vegetarianism, or I What does now pescatarian ism, are talking about falling into the millennial generation. So I think that some of the things that can feel like our biggest fears on the emotional side, not on the logical side, need just as much tending to and attention. And sometimes actually just going through the gauntlet, and experiencing your fear, in reality of your day to day life, can show you what you’re made of, and show you how resilient you are, and can teach you about your own character and perseverance, and can. And this might not happen for everybody, but it certainly did for me can help you double down on what you’re doing and why.

Jenn Smith  21:24  

Yeah, I agree with you. And that visibility thing is so hard, it’s still hard for me even after a few years of doing this. And I think like one thing that came to mind when you were sharing that story is that I feel like sometimes people have their own insecurities that they have to share with other people or project on other people. Unfortunately, that one sounds like it happened to you. But I think that that happens, you know, and they have these own feelings or even jealousy. And that kind of comes out in different ways. But being resilient and building that up and knowing that you have more to give. And I guess like the piece that always helps me get through that is, if this helps one human being, it’s worth it. That’s all that matters. One human, that’s it. And literally, that’s kind of like the I don’t know, like the concept that helps me kind of get through that emotional fear of visibility, and what other people are gonna think is just that one person, you just think of that one client, that one person and keep going so

Lisa Lewis Miller  22:28  

well. And Jenn, I feel like the converse of that is really important to have, if you choose not to post this, if you choose not to share this thing or not to be visible, you are actively depriving at least one person being helped

Jenn Smith  22:41  

100% Yep.

Lisa Lewis Miller  22:43  

And just remembering like, how does that feel like you, we all get into the game of exploring entrepreneurship, because we want to do work that feels good to us. And that matters and makes a difference. And feels worth it feels worth giving up a lot of the luxuries and privileges that employment has. And so reminding yourself of, I could help even just one person by speaking on this stage, or writing this letter. And if I don’t, I might be depriving that person of getting the message that they need today, or hearing the inspirational story that can help you get out of bed or get over your insecurities and fears and, and just do it.

Jenn Smith  23:31  

Mm hmm. For sure. I’m listening to one of Seth Godin books right now. And he talks about that with marketing. And like how, you know, scary sales and marketing can be but he explains how you’re actually doing a disservice to the people that could use your work and your efforts in that way. And that’s such a major reframe when it comes to sales and marketing, especially for people like me, who are uncomfortable with it. And man, is it powerful when you think of it that way.

Lisa Lewis Miller  23:59  

And a lot of folks have a hard time buying into that. Like, what do you mean marketing is serving, I get so many marketing messages during a day, I feel like I could barf. But think about the things and the purchases in your life that you treasure, and you value. And imagine that for whatever reason, you would never stumbled across that store or that brand or that item or that offering. Like your life would probably be measurably less good because of that. And if you are wanting to be an entrepreneur, at some level, you got to believe that what you’re doing is valuable. And if you believe that what you do, be it selling a product or a service is valuable. In this weird, twisted way you have a moral obligation to tell people and to help them and to serve them by letting them know that’s possible and it’s available.

Jenn Smith  25:01  

Yeah, and I think like the feedback that you get from the people that you’re serving or working with is so valuable to help you be able to move forward. So you think of that one person, you know, in our sense of career coaching, like we’re supporting one person, and making a fulfilling career change. And when you see that happen, and you see their lives transform, you know, it gives you that energy to do one more and to do one more and to do one more. So, you know, same thing, if you were, you know, helping people plan parties, or writing a book, or whatever it might be, you know, you get that one little nugget of feedback of that one person that it impacted, and it keeps you moving forward. Super important.

Lisa Lewis Miller  25:41  

Well, let’s talk a little bit more about marketing and visibility, because there’s the moment when you make the internal decision of okay, I want to give entrepreneurship a try. And then there’s the moment when you first have to tell people outside of your own head, that you are starting this journey towards entrepreneurship. How did you know when you are ready to start sharing that externally? Yes.

Jenn Smith  26:09  

So the first thing for me was that I didn’t see another role for me in corporate. So I was so used to like, knowing what’s next, knowing what’s next, knowing what’s next. And I hit a point where I was like, There’s nothing next to like, what’s going on here, you know, and so then it’s like, okay, maybe it is time to explore this other thing a little bit. And so, starting to talk about it was one of the hardest things. So I was, so it’s like an identity shift. You know, like, you’re so used to saying, you know, I’m a corporate HR leader, and here’s what I do. And so shifting that to an I, the way that I went about self employment was starting a side hustle. So I started a side gig doing career coaching. And so when people started asking me what I did, I started sharing that piece of my work versus the corporate piece of my work. And it felt so awkward and so weird. I mean, even something so simple is like telling somebody at Starbucks, you know, when you’re in the drive thru, and they ask you what you do, because you’re waiting for coffee, I was like, You freeze, like I froze, and so it just, but just practicing it and starting to get it out there and share stories and why you do what you do. And that’s really, once you start and you start feeling good about it, and you start practicing it, it really becomes more natural. So talking it out, I felt like was a really big piece of it.

Lisa Lewis Miller  27:32  

That makes sense. And it’s such a testament to your courage, of being willing to start trying on an expressing yourself through this new identity. Because you’re totally right, that it’s it’s an identity shift. And in a lot of ways it can feel like a certain amount of loss, like I am allowing this old me this old identity that was tethered to the corporate world to fade away. And if we want to use kind of dramatic language for allowing that version of you to die, Mm hmm. And allowing you to step into this new sense of you, and this new identity and the new frontiers and possibilities that are open to that version of you. But it’s, I will oftentimes talk about this kind of metaphor of having one foot on a dock, yes, and having the other foot in a boat. If you leave those two feet, where they are, you ain’t going nowhere. Right? One foot is going to be highly unstable and kind of drifting out to sea, your other foot is gonna be very stable, you are going to have thigh muscles of steel, trying to support yourself and keep yourself from doing the splits. And you have to at some point, put both feet somewhere. Either put both feet on the dock or put both feet in the boat. And it can be terrifying. But it’s also the path forward no matter what.

Jenn Smith  29:00  

Yeah, I love that. I love that visual of like the split, like you’re doing a split and it’s like okay, what’s gonna happen I’m gonna end up falling in the water here, you know, if I don’t do something and so, you know, kind of, I think that’s where it comes to, like, you start talking about it, you start testing it, and then you kind of figure out like, okay, we’re which piece of this like which foot you know, is generating my energy the most and let me do that is kind of like my next step and testing it out and figuring it out along the way is kind of part of the work but but yeah, I mean, a lot of us you know, kind of have that split or even if we’re like walking a fine line between the two of them for a long time until you feel like you know, you feel like you’re ready to give it a shot full time. You know, and I think like going back to like that financial piece because I think that’s another one of those you know, they’re just the the thing that holds a lot of people back and so if you’re doing this because of the financial piece, you know, figuring out what that you know, figuring out what that looks like for you and then knowing So for me, it was like knowing that I could make money doing this work was a big thing. So like, that’s where the side gig comes in, like just figuring out what people need testing it out knowing I could make money, not that I had to like match my corporate or anything like that, like I was okay, just knowing the fact that I could do it. And that allowed me to step both feet on the dock and give it a shot versus, you know, continuing to kind of teeter that way. Where I know some people in terms of like, when they are teetering like that, and the Financial Peace is a concern. They kind of go towards like, Okay, I got to make even like I got I, in order for me to get both feet on the dock or both feet in the boat, I need to be making what I’m making in my day job before I can leave, you know, before I can leave. So I think everybody’s different in that aspect. But it helps you kind of like just doing it helps you get both feet on either side.

Lisa Lewis Miller  30:55  

Yeah, absolutely. Well, I think that that that proof of concept that you’re talking about, I need to ensure I can make money doing this before I go all in is such a logical, pragmatic way to approach it. And for me, when it came to making the leap, the financial runway piece was a big piece for me, because I had started doing this side hustle career coaching work back in 2015. And I was still employed nine to five at that time. And I looked at the numbers, I looked at, like, what am I making from my current job? What is my current lifestyle cost? Like, what are my fixed costs of, you know, what I’m paying to live? What are some of my variable costs that I might be able to tamp down for a little while. And I gave myself the decision making criteria, if I can get my side hustle to be generating 50% or more of the salary that I’m currently making in my nine to five, for three consecutive months. If and when I do that, I am allowed to put in my notice and make the leap. Because I was putting probably 10 hours a week into my side hustle. And my my brain went through this logic chain, it said, if I can use 10 hours a week to make 50% of my salary, it should be pretty easy to go to 40 hours a week, and at least match the salary that I was making, if not exceed it. So I remember, it was the end of 2016. And it was September, October, November, were my three months that I made 50% of what I was making in my day job through the side hustle. And at the end of November, I thought well, I gave myself this criteria, I guess I have to go for it. And I put in my notice. And one of the things that that decision making criteria allowed for me to have was once I made the leap, I had squirreled away the money that I had been making doing career coaching on the side. And I had about three months worth of matching my current full time income. But I was already making a halftime income. So I figured, okay, I’ve got about six months of financial runway, because I’ve got like a an extra half of a paycheck to augment those next six months. So six months feels like a pretty good financial runway, given the recurring revenue and the recurring options I’ve got going on right now. To give myself the opportunity to hack it and make it happen. And Jenn, I love that you shared your story about wanting to be an independent financial contributor to your household. Because when I first made the leap, I wanted to be self sufficient to I at that point was was unmarried. But I was with somebody who I was about to get engaged to. And I thought you know, if this all goes to shit, at least, you know, my partner at the time can support me, right? Like he could be the final safety net if I need one. And then of course, the engagement totally blew up and everything went sideways. But because I got into it thinking I’m going to be financially independent, and he’s just, you know, a safety net for a safety net. I could weather that just fine. As an independent single lady, figuring out insurance, you know, figuring out how to do the tax stuff, figuring out how to generate more revenue and more opportunities and landed on my feet. And you know, made Six years of running a business without ever running a deficit in the business. I love that

Jenn Smith  35:07  

story. And you were definitely much more logical than I was. So that’s definitely where the differences here because I saved money. So my financial runway like I squirreled away just like every penny that I possibly could, for a good amount of time. And I gave myself a one year runway in terms of lifestyle and having that money saved, I gave myself that one year runway, but I did not do the piece that you did around the matching income. So the second I saw the demand for the work that I was doing, plus the fact that people would pay me at that point was very little amount, but just the fact that someone would pay me and the demand was there. That was my ticket, I was out. So the second I saw that, and I knew that I had a good amount of money saved up. That’s those two kind of things, where were my decisions, so you were much more logical? Anyone listening? I would recommend following Lisa’s logic in that from that perspective, well,

Lisa Lewis Miller  36:07  

I think both ways, we had proof of concept that we can be paid for the work we want to do. And both ways we had been living under our means to squirrel away some capital for a rainy day just in case to take care of ourselves. And ultimately, you know, neither one of us exhausted those financial runways. And we were able to come up with ways to make it work and make sure that our business models built in a little bit more recurring revenues so that you kind of could forecast out like, am I going to be able to eat next month? Yes or no? So even though we had different decision making processes and different ways of getting there, I think that the the bones of what set both of us up to be successful and stable entrepreneurs is very similar.

Jenn Smith  36:50  

Yeah, good point.

Lisa Lewis Miller  36:53  

Let me ask you this. So you and I both used to be well entrenched in the corporate world. And I’m sure the both of us just dreamed of working for ourselves and being our own bosses and having the freedom and the autonomy, getting to set our own schedule and decide exactly what we work on. When you actually made the leap, and became your own boss, what surprised you most?

Jenn Smith  37:25  

Two things come to mind. One is that I was actually looking forward to Monday. And I still am to this day. So my timeline was my my last month in corporate was the end of 2019. So coming up on two years, I’m still looking forward to Monday, which I know, being in the corporate world, you can’t even fathom that. But it is legit. It is true. Even sometimes on the weekend, I’m like, okay, Jeremy, go back to work. Like, I’m ready. Like, I’m ready to get back into it, I want to be with my clients, I want to you know, write the next blog, you know, so. So that was a super exciting, fun surprise that has held true to this day. And then the surprise on the opposite side. So I’m a pretty introverted person, I like my alone time, I don’t like a ton of interruptions, you know, drive bys, dings of all the things I like to, you know, have my space and be quiet a lot of the time. But one of the things that has surprised me is that this, this self employment thing can be a little bit lonely. So, you know, kind of like being on your own, it can get a little bit lonely in the sense that you don’t have your friends at work. Um, that is a big deal. You know, so I think, you know, the, the thing there is to have a network of other self employed humans, which is one of the reasons I’m so grateful for Career Clarity Show and the team that we have, just to be able to support each other, you know, in that sense that sometimes the dates can get a little bit lonely. So a good surprise, and then a little bit of a struggle, surprise, but one that’s, you know, easily fixable, you know, kind of putting yourself in those situations with others.

Lisa Lewis Miller  39:16  

Easily. Let me let me say easily fixable with intention. So right before I hit record, Jenn and I were talking about another podcast guests that I’m having Smiley Poswolsky And he wrote this book called friendship in the age of loneliness. And he is this expert on both friendships and loneliness. And he’s self employed, like Jenn, like you and I are. And he talked about how addressing that sense of isolation and loneliness. isn’t rocket science, right? Like it’s not some sort of complicated formula, but it doesn’t mean it’s easy. You have to be intentional and you have to be proactive. You have to be thoughtful about what kind of interactions will fill up your cup. And seek out that kind of community around you. And so I think, Jenn, to your point about the the loneliness that can come with entrepreneurship, the if you’re wanting to go out on your own, like, this is a time to double down on making friends that, that persevere outside of work, and finding communities to connect in with where you can be supported by other people who can understand what the freelance or entrepreneurial or self employed life is like. So, John, I think that’s such a good reflection. And I think I cut you off when you were asking the question back to me about surprises. One of the biggest surprises for me was that I was not as stressed as I thought I was going to be, I thought that entrepreneurship was just going to be like one giant ball of stress. And that I was going to quit after three months, because I just couldn’t hack it, I couldn’t take it, My nerves would be fried, my adrenals would be shot, I would hate everything about that sense of uncertainty and wondering where my next meal was gonna come from and whether or not I had enough clients to be able to, to make rent. And that was so not my emotional experience of entrepreneurship. Was it hard? It’s still hard? Yes. Was it an Is it challenging and stretching your ability to problem solve? Yes. Does the ups and downs bit of uncertain or unstable income trajectories still scare the bejesus out of you? Yeah, sometimes. But when I had this dream, to be an entrepreneur, and I gave myself permission to do it, it, it changed me. And it made me feel so much more capable and self assured of like, well, I don’t have any crutches, I have to figure this out. I’ve got a problem. So I need to figure out how to do quarterly taxes, I need to figure out how to do appropriate marketing, and build up a list of prospective clients to chat with the fine folks who are really good bits. And that sense of quiet capability and confidence has been such a gift, and such a blessing. And I think really changed the way that I related to stress and to problems that popped up in my day to day life.

Jenn Smith  42:40  

Yeah, and I you take, you know, kind of those learnings from the corporate world and bring them into your own. It’s like, you know, you build up that tolerance, resilience, whatever you want to call it, and then you’re able, you’re able to do it so much better, easier, maybe not the best words, but you know, you’re able to kind of get through it, you know, when you when you are in it for yourself. So yeah, that’s a lovely surprise.

Lisa Lewis Miller  43:05  

Agenda. The piece of that that was also a surprise to his height, didn’t realize how much anxiety and stress I was carrying around day to day in corporate life, that it didn’t completely melt away. Right. Entrepreneurship was never sort of a cakewalk. But I felt like my day to day blood pressure went down. Like yes, I still have problems, but I have to figure them out myself. And I know I can rely on myself. And I’m going to do this some way somehow. So I think that the the exhale that came with leaving corporate for me was totally surprising. I like to fancy myself a pretty self aware person, and I just had no idea.

Jenn Smith  43:49  

Yeah, I love that. I think like the creativity that comes with whether you’re problem solving, building something, whenever the creativity that comes with being self employed, and being an entrepreneur really outweighs you know, the kind of the struggle or the stress or whatever, you know, comes with it, at least for me, it definitely does. Well, Jenn,

Lisa Lewis Miller  44:11  

I’ve loved having this conversation with you. And I feel like we could go on for hours and hours talking about the lessons that we have learned through our years of entrepreneurship. And congratulations on your entrepreneur anniversary coming up here to bring us to a close. What advice would you give to somebody who’s kind of standing on the precipice of possibly exploring entrepreneurship?

Jenn Smith  44:33  

So my advice is to just start so if you and it depends on the stage, but if you have this idea and you have this kind of chirping voice, I want to tell you that it is not going to go away. And so what I would say is give it a try, just start there’s really something to be said when you Give it one little shot and start that momentum. And you know, kind of figure out that meandering path along the way. There’s also something to be said, when you dedicate your time and energy to it and actually do it versus thinking about it, that can be a game changer, and really help you decide if you want to do it. Full time are not

Lisa Lewis Miller  45:24  

so good. I had a college friend who had this acronym, and it was different. And it stood for, do it for the story. And it was kind of this mental model this modality of, you know, I’m just going to try it, I want to be the person with the stories, not the regrets. And it doesn’t mean that you burn everything down around you, right, it doesn’t mean you march into your employer’s office and hand them your two weeks notice or virtually turn in your two weeks notice and the world that we live in. But it does mean giving yourself that permission to just try it. Just Just dip a toe into the water, you know, take a teeny bite and see if you like it. So Jan, I think that’s fabulous advice. And I think I would totally agree with that. I feel like I want to give some other piece of advice, but that’s so good. Maybe the other advice is, start taking a look at your finances to figure out how you can give yourself optionality. Because even if you decide you try entrepreneurship and you hate it, maybe you realize you need a sabbatical. Or maybe realize you want to go to grad school and start a completely new career path. And if you start thinking today about what your future self might want, the might want to have the option to do. And you start financially trying to make that possible for yourself. It makes the the buffet of options, the portfolio of options that are available to you when you’re ready to make a change. So much bigger, and so much more useful. So just do it, start diving on in and think about making some financial decisions that are going to make your future self really happy. Yeah, and

Jenn Smith  47:20  

just to add to that point, instead of just thinking about the finances, or going through all the what ifs in your head, write it down. So like, write it down, go through the budget, there’s tons of different worksheets, you can Google, that’s what I did to get it, write it down and see what it looks like on paper, something transforms when that happens. And it can give you kind of that note to just start or just give it a try.

Lisa Lewis Miller  47:45  

And you know what, Jenn, we should put into the show notes from today, the money and happy article series and worksheets that we’ve got, because we’ve got something just like that. So if you’re listening and thinking, you know, Jenn, it would be great to have a worksheet to do that. Jenn and I will hook you up, go check out the show notes. We’ll have a link to that so that you can use that and dive in today. Well, Jenn, thank you as always, for coming on the Career Clarity Show. And if you’ve been listening and think Jenn is as delightful as I do. She is one of our beloved career coaches here at Career Clarity Show. And she loves to work with folks, certainly budding entrepreneurs, but all kinds of folks who are wanting to make transitions, you can check out more about her on her coaching page at get Career Clarity show.com. And we’ll have a link to that in the show notes too. But Jenn, thank you again for coming on in sharing your brilliance with us today.

Jenn Smith  48:38  

Thank you, Lisa.

Lisa Lewis Miller  48:46  

And that’s a wrap. Let us know what you thought about today’s episode. Leave us a review on Apple podcasts. Because not only can your stars and word to help us find great guests and topics to feature on future episodes. Your input also helps other people find the resources they need to discover the work that lights them up. And make sure to check out my book Career Clarity: Finally Find The Work That Fits Your Values and Lifestyle. For the link to order it go to GetCareerClarity.com/book. And don’t forget to get your other tools resources and helpful goodies at GetCareerClarity.com/podcast. Thanks again for joining us for the Career Clarity Show today. And remember, if you don’t love your work, we should talk because life is too short to be doing work that doesn’t light you up. Talk to you next time.