How to Know When to Jump into Your Side Hustle

LinkedIn: [00:00:00] Linkedin presents.

Listener Megan: [00:00:05] How do you know when the best time to make this jump is? I'm in this transition point. I could make that jump right at the end of the school year and dive head first into the business, but I don't know if it's the right time. It's a big question and I don't know how to make that decision.

Jonathan Fields: [00:00:21] Hey there. And today's episode listener Megan asks, how do you know when the best time to make a jump is? Especially when you're clear on exactly what you're jumping into and in fact, have already started building it on the side and on deck with me to help out this week from the SPARKED Brain Trust to tease out what really matters and share insights and ideas, is bestselling author of Life After College and the groundbreaking book Pivot and Free Time, and also an incredible career and business strategist, Jenny Blake. So quick note you'll hear us mention something we call Sparketypes in conversation. So what is that? Well, it turns out we all have a unique imprint for work that makes us come alive. This is your sparketype. When you discover yours, everything starts to make sense. And until you discover yours, it's a little bit like fumbling in the work life, dark. And just like today's listener did, you can discover your Sparketype for free at sparketype.com. You'll find the link in the show notes. Now on to Megan's story and question. I'm Jonathan Fields and this is SPARKED.

Listener Megan: [00:01:30] Hi Jonathan and the SPARKED team. My name is Megan. I go by she her. I am in a very transitional point in my life right now where I am a high school biology teacher, feeling very burnt out with the state of education and just how things are shifting right now. Even though I love my students and I love the content that I teach, there are a lot of things outside of my control that just are frustrating. I am also a small business owner, and my husband and I started a winery where we make honey mead. We started in 2020 right after the pandemic started and it's something we do when we are not teaching. So in the evenings, weekends, summers, we focus on making our wine. It's made from all local ingredients, so very hyper local to our area. Some of the things we even grow ourselves. So that includes the honey we. We started raising a handful of beehives last year and adding on about 50 more hives this year. I'm really excited about that. We have fruit trees, we grow vegetables, and then we source everything that we can't grow ourselves. We source them right from our friends within about 20 minute radius. So we make a really, truly unique wine, local alcohol that's not really found anywhere else, the style that we make. And so that's something that I'm passionate about and really love and and hoping to transition to that full time. But I've been in this journey where I'm trying to figure out what the best approach to do this is because I'm also a parent. I have two young children that are two and almost four, and trying to make sure that I make good decisions for them, keeping them safe and secure and, you know, benefits, pension, all of the things that are worth considering, uh, that I do have right now and I wouldn't necessarily have in a startup company.

Listener Megan: [00:03:19] So I met a very big transition point, which is why I actually took the Sparketype assessment to begin with. I found that I am a maven and my shadow Sparketype is a maker, and as soon as I saw those results, it made a lot of sense because I love learning. I like picking up new things and always learning something new. And that's probably why I'm so interested in this business is there's so many facets that really that help us do what we love and what we're passionate about, but it requires a lot of learning as well along the way and always acquiring new information. And I enjoy that. But I also like having that that maker ability. I do a lot of the digital creation for our company and and those things just really make me happy. I thought I was going to be more of a scientist, which is funny, um, that I wasn't, but taking that assessment just answered a lot of questions for me. So one specific question that I have for you all is, how do you know when the best time to make this jump is? And I'm in this transition point, I could make that jump right at the end of the school year and dive head first into the business, but I don't know if it's the right time. It's a big question and I don't know how to make that decision. So I would love it if you could help me answer that. That would be amazing. I do hope to hear from you all. And in the meantime I will keep listening. Thanks so much.

Jonathan Fields: [00:04:41] Okay. So first, do you also like are you excited to try and figure out how we can order some of her honey mead? Because I don't think I've ever had that.

Jenny Blake: [00:04:51] Yes. I'm sitting here picturing Megan teaching walking people through these adventures of the winemaking process. It just sounds so epic. What she's doing. The fruit trees, growing vegetables. She says it's so casually like, oh, I have 50 beehives that we're cultivating. I'm just my jaw is on the floor, right?

Jonathan Fields: [00:05:10] And at the same time, the full time teaching job. Mom of two kids. Um, yeah. And if we zoom the lens out, you know, I mean, we'll dive into the details, right? Of her unique circumstance, but bigger picture. I mean, how many times have you heard sort of like a different fact version of a really similar scenario in the work that you do?

Jenny Blake: [00:05:33] I mean, I hear this all the time. I think what Megan might not realize is how far along in the process she is just hearing the difference between her starting and saying, I'm feeling very burned out, which is so understandable given the work that you're doing. Megan. Oh my goodness, I don't even know how you're carrying everything that you are. High school is intense as is. Throw on a pandemic and two small kids at home. You're my hero. The what's so incredible is that you have this this epic magna. And knowing that you're a maven maker, I cannot say I'm surprised. We could say with a scientist twist, it's so incredible that you have this clarity and this passion and this company that you're already building with your husband. I think you're way farther along than you think. And to your question, Jonathan, I hear so many people who say, I'm burnt out, I'm bored, or I'm at a pivot point or a plateau and I have no clue what's next. In Meghan's case, she's pretty clear and it's so epic, this unique, as she said, truly unique product that she's creating. And the joy in her voice that it's not doesn't seem as much a question of if she should go all in, but when.

Jonathan Fields: [00:06:35] Yeah. And that in fact was was her question. But but I agree with you. I think so often one of the things that we forget to do is acknowledge where we are in the moment. And sometimes we don't do that because we're struggling and we realize, okay, if we if we own that, it's going to be difficult because we have to own what we also don't know. This is an interesting scenario because at other times, sometimes we don't own how much we've already done, how far down the path we've already come, because all we do is we look at how much, how much there is left to do to grow, to quote, make happen. Um, and so I love the fact that you're kind of starting out by saying, can we just acknowledge right here and now how astonishing it is, how, how much you have accomplished already, the fact that you're literally you've got two more or less full time jobs, three if you count running a family. And certainly that does get factored in there. And you've got, you know, she's got clarity around not just clarity around her vision, but implementation. She's like, this is something that exists. She's clear about, she's passionate about, and she's excited to move it to the next place, which is I think it's so it's so important to just acknowledge how much has already been accomplished.

Jenny Blake: [00:07:48] It also shows you how contagious it is when someone is SPARKED to use your term for this, you and I are both listening with a huge smile on our face. I could just see us both with the number one foam finger going like go Meghan, go in your husband and seeing how much joy is in this process for you. And I think it's rare that you find a maven maker who knows how to apply their skills in such a hands on, comprehensive way. The big thing that jumps out to me is just fear, which is so normal. I don't say just fear as if it's some small thing. I think the reason that career changes like this can be so intimidating is that it feels like our survival is at stake, that if Meghan makes the wrong move, or in the wrong timing, or if it doesn't work out, it's the very ability to provide for yourself and your family long term security, stability, health insurance. I mean, these are very real concerns. And they get to our root fears about survival. So it's also I just want to normalize how scary this moment is that even with all the clarity in the world and all the excitement about what might be next, it is so terrifying to contemplate leaving anything secure for something that feels very unknown.

Jonathan Fields: [00:08:56] Yeah, I so agree. You know, I think it's it's important to both acknowledge the top of Maslow's hierarchy, the aspirational, the self-actualization, the. This is amazing. I want to make it happen. And I have a clear picture and I'm making it happen. And at the same time acknowledge that that that is always still built on the bottom of the pyramid, you know, safety and security, sustenance is there. And if we don't have that part, then all the aspirational stuff doesn't have a foundation to sit on, and it tends to crumble the minute it gets a bit too scary. Which is exactly what Meghan is referencing here. Right? And she's saying, this matters to me, I acknowledge it. You know, that security that making sure like financially we're okay thing. Actually it's important to me and. Saying, I have that now with what I'm doing as relate the full time thing, even though that's the thing I want to phase out of. So clearly she's also has she has a deep value around financial integrity. And this is something that I, that I think is a really interesting thing that comes up often people who have this shared value around financial integrity or security, whether it's just for themselves or for an extended family or whoever it may be, and at the same time, a deep yearning to do something that they sense, um, in some way has to at least temporarily pull them out of the place of honoring that value. What are your what's your take on this, this dynamic?

Jenny Blake: [00:10:23] Oh my gosh, I have so many thoughts here. You're right. There is this value of financial integrity, security and also responsibility being the responsible adult and keeping the lights on for everybody. I've been running my own business for 11 years now, and I still remember how afraid I was. I was working at Google for five and a half years and I was so afraid to leave. I mean, just really, really, truly did not see myself as an entrepreneur or being able to, quote, make it on the other side. And I kept saying to myself, what if I end up in a van down by the river? So to counter that, I just started to open the possibility in the inquiry. But what if I earned twice as much in half the time? And the number one thing that I underestimated in that moment of fear? Dan and Perry talks about being in between trapeze bars in a beautiful essay on this topic. I underestimated the power of my full creative energy. After I left Google, there was about a month or two where I was really just sitting on the couch every day, kind of a vegetable, because I was so tired and I was so burnt out.

Jenny Blake: [00:11:22] I can relate so well to what Meghan was talking about. But then I realized that once I could harness my full energy that I had been giving to Google and a side hustle and everything else I had going on once it was all harnessed toward my business. It was incredible how much the business gave me energy, how much available, just space I had to problem solve to figure out how I was going to earn enough money every month to keep the lights on. And that's something that I say to a lot of people who are at this decision point. You will have so much more creative resourcefulness once you kind of recover and recharge from juggling so much that you're not going to let yourself down, especially if you have all this financial responsibility, you're going to figure it out, and you're going to have your full focus and creative energy to apply toward that instead of having it be so dissipated, spread out, and then, as a result, exhausted. It's really hard to think creatively and earn financially from that place.

Jonathan Fields: [00:12:20] Yeah, I love that. Um, and I have I think we have both experienced that a number of times over now. Like I have a very past life at this point, you know, like working in big enterprise as well. One of the things I wanted to ask you about, also because it's kind of implied as a sub question in Meghan's question, is this notion of burning the ships, you know, so so there is a mythology in the world of entrepreneurship that basically says when you walk away from that sort of like main focus thing, and you step 100% into the world of entrepreneurship, that you have to basically completely close the door and never, ever think about it again and pretend that whatever that past life is no longer exists in your future. That's the only way that you unlock your creative and cognitive and generative energy to do the thing that you want to do. And at the same time, there's also interesting research that shows that many of the largest companies that that were, in fact, startups not too long ago, um, they didn't start that way. They actually started with at least one, if not all, founders holding on to their day jobs as long as humanly possible. Sometimes, you know, like there would be one final one who was holding on for years. And it's this notion of, on the one hand, you want to free up all of your capacity to devote to the new thing. But on the other hand, there's something about building it to a point where you can feel like you can almost make this lateral move without having to take a hit where, like, you're building as, as long as humanly possible, where it's literally it's proved itself already and you just slide into it and you kind of know at that point you're going to be okay. What's your sense on that?

Jenny Blake: [00:14:03] Right. It's almost like you've built the new boat. Yes, you might burn the old boats, but you built the new one and your feet, you just need to leap into it with both feet. Now, what's interesting about Meghan's situation? It's not like she's saying, I'd love to quit my teaching job and someday start a winery. Wouldn't it be cool if it's happening? This business exists. I mean, once I heard 50 beehives, I was. I was just thinking, this exists. This is real. She's in it. She's already rolled up her sleeves with her husband and building something truly unique. And the energy in her voice was so inspiring to me. And oh my goodness, it just feels like she's there. So it's at least. Talk about acknowledging progress. At least she's not just it's not a figment of imagination that she's thinking about moving toward the biggest practical consideration to me. I know with leaving a teaching job the big risk, it's a little harder to just go straight back to it, because a it's hard to get those jobs and you are giving up tenure and a pension that you accumulate. You accrue for the duration of the time that you've been teaching in that district. So that does feel a little riskier than someone saying, oh, you could just go get another teaching job. I know that it's not like that. What I would get really curious about is, is the business earning any money or is it losing money? If you need your paycheck to actually fund the growth of the winery, to get it to that escape velocity point where you can leap over to it full time? That's one thing.

Jenny Blake: [00:15:26] But if the school commitments are actually draining your ability to earn money through the wine business, it seems like where your energy and attention is is that you're kind of ready to go all in over there, then you just need to know how long are you willing to give yourself Megan and family until you go to plan B? So how long is that in time and months and years? How long is it in financial runway? And what I like to do is just set a point about halfway to that point where I say, what are my worst case scenario, cash outs? So if you were to leave your teaching job, how much do you need to earn through the winemaking business and how quickly? But I just see so much possibility for you. I see Megan still being a teacher, honestly, and giving tours and teaching virtual classes and on beekeeping and growing fruit trees and like harvesting and this unique wine making and we all making honey, mead, wine. I mean, there's just so much that I still I still see you teaching Megan just in a slightly different way.

Jonathan Fields: [00:16:23] Yeah. It's so funny that you say that because I was sort of getting a similar thing. I was thinking to myself, you know, um, a number of years back on, uh, on Good Life Project. podcast, we interviewed a couple that started this biodynamic farm north of LA after both leaving these long time, big, full time careers in media and stuff like that. And part of the way that they were building this farm, because they believed in this, they believed in sustainability and all this, but also part of the thing they love to do was they turn it into a learning center, you know, where they were constantly bringing students and adults and having tours and experiences and workshops. And so what you're keying in on is this notion of maybe you actually, it's not about leaving teaching, it's about leaving the current institution or container within which you teach, but also knowing that if you still have this passion to do this thing and you're just learning a ton, which he said is, you know, like her primary Sparketype is the maven that's all about knowledge acquisition. And she loves how much she's learning. And it sounds like she also loves to share what she's learning. Then maybe it's less about thinking, when do I leave teaching? And more about thinking, how do we bring the parts of teaching that I love into this endeavor also, so that it even brings a a secondary form of marketing, and at the same time, a secondary way to express that same Jones that she's getting satisfied in, sort of like in the container of more traditional teaching environments all wrapped up in this new endeavor.

Jenny Blake: [00:17:53] Yes. And that the teaching might become one of the more profitable parts of the business, let's say through teaching courses or being able to teach virtually that winemaking, that's probably takes a lot of resources, time and energy and money and materials and all the ingredients that go in and the packaging. So the teaching could actually be this great supplement to the winemaking itself that's in your zone of genius, Megan, and serves serves the world. I would also ask, what is the pension? It's almost that instead of worrying, what if I lose my pension? You could turn it into a creative question what kind of pension do I want to create for myself? And that you and your husband dream a little bit and say, what is that number? What does a pension, a self-created pension look like? How much would we need to earn through the business? Maybe all teaching money goes into a separate pension account, and only when it's filled to a certain point. Then do you start to take that back as profits. I don't know, I mean, you could just get creative with this, but I just found that it's more helpful to turn those fears into open ended questions, especially if, like you just said, Jonathan, if you're a maven and a learner, I know you're going to hunt down these answers like, I know you're going to have conversations, listen to podcasts, read books until you find those answers like that is a skill that's really going to help you here.

Jonathan Fields: [00:19:13] Yeah, I totally agree with that. And there's another really interesting dynamic that I thought we might talk about. So Maven Maker, when you're leading with a just mad love of learning everything that you can about anything, and then you reach an inflection point where you've got to make a fairly substantial decision. I have seen this interesting pattern where when your fundamental impulse for effort is to learn, learn, learn, I need to know more and more and more and more and more that can sometimes get embedded in a bit of a frustrating way in a decision making process, because you keep feeling like, oh, but there's so much more to know. I don't actually know enough to make this decision, when in fact, sometimes the way that you get the knowledge to know, to really finally know whether this was a right call or not is to make it to almost like set a date, make it, and then everything you learn the moment after that is going to start to. Form, like how you're going to move forward, what was right and what was wrong, how you might have to, Jenny, in your language, pivot to make this whole thing work. Not in a negative way, but in in a possibility oriented way. But there's a really interesting dynamic between this, um, this just fierce desire to perpetually learn more and the need to at some point say, I don't have perfect information, I'll never have perfect information. I just need to make a decision.

Jenny Blake: [00:20:37] Yes, I say in pivot, decisions are data. I'm an essentialist with a maven shadow. I have this feeling. I wonder if you feel this way, Jonathan. But that mavens we might struggle with imposter syndrome a little more because at least I'll speak for myself. I know how much I don't know, I know how much is out there. I'm so hungry for learning, and often I hold a really high bar for myself because I'll read business books or listen to podcasts and think, I'm not there yet. And that's that love of learning. But you're right that it can turn into analysis paralysis and compare and despair. Let's say the not in your sense of the word shadow, but the shadow side of being a lifelong learner. I when I left Google, I did not think I was equipped to be an entrepreneur. I say that I don't have FOMO. I had font fear of not trying there just reached a point where I wanted to know that I tried. I genuinely had no clue if I would make it longer than six months, but for the first time in my life, I was willing to try, and I was willing to spend the amount of money that I had in the bank to last me six months, and I kind of figured it might just all go to zero. And that, I think, is part of the Maven impulse, like you said, is like we we love learning.

Jenny Blake: [00:21:47] And if if we don't hold too high of a bar that at some point you trust yourself. And I think that's the thing that comes to me as well, when I'm listening to Meghan's question, is just how big a role intuition is going to play in this decision that if you really tune in, you will know when it's time. And I already hear the whisper of maybe at the end of the school year, maybe at the end of this summer. And one thing I like to do is try on a decision. So why not just assume that you are not going back in the fall? This year is your last year teaching. Just try it on for the next month or two. How does it feel? Are you terrified or are you kind of excited? And are you holding yourself back out of fear of not knowing enough like Jonathan was describing? Or are you excited to turn your attention like like you said, Jeff, it takes a lot of mental cycles to spin and chew on a decision. So I think what's really freeing is once you make that decision now, it's like, great, how do I build the plane while I'm flying it? And I think a maven maker is a really exciting combo for a business owner entrepreneur, because business building involves so much making, even though it's not the same as the wine making, it's still a very creative process.

Jonathan Fields: [00:22:59] Yeah, 100%. And what a lot of mavens do, especially a maven maker pairing, is they actually lean on the process of making of creation as their core mode of learning. So it's not just book learning, it's doing. It's the creation that actually becomes the the sort of the central mode of knowledge acquisition. One last thing that just came to me that I want to run by you, Jenny, that, um, I wonder if it might be sort of like an interesting bridge move for Megan here. And that is, um, what if you take your experience, your, you know, your history, your credentials, and what if there's there's actually a middle step here, which is you sort of decide on a date where you leave behind that conventional teaching modality, and maybe you haven't ramped up whatever you might do on the teaching side in the new business yet. But what if there was this bridge, sort of like window in the middle where you say, you know, actually my skills and abilities are deeply needed, deeply desired, and actually often more highly valued outside of conventional teaching paradigms, in sort of like more of a professional setting or tutoring or individual like working individually.

Jonathan Fields: [00:24:16] I wonder if there's this interesting sort of like intermediate step that says, okay, so we're we're closing the door on the way that I've been teaching for like however long it's been now. But at the same time, I'm opening the door to this interim, this bridge thing that potentially allows me to generate a similar amount of money or enough so that we're very comfortable between that and what the the wine business is generating. But I'm doing it in a way where me and my time are valued at a much higher level, which means that I can work less doing that and devote more energy to this new thing. And that way, it's sort of like this interesting bridge move of honoring that value of financial integrity, and at the same time, being able to free up that creative and cognitive and learning and making bandwidth to devote more of it to. A new venture. So it's what do you think about a move like that?

Jenny Blake: [00:25:14] I love what you're describing, and I love having that in mind as either the bridge that gets Megan to full time at the winery or a plan kind of plan B or A plus, you know, something right on the side, right close by. Because I think that can also give her a lot of confidence in making this move. But I love the idea of tutoring or it's so a different per school and per district. I have a friend who runs the computer lab and he's like the head of tech. Now that might sound totally cringeworthy to Megan, but maybe there is some you will know better than us, Megan. But like, maybe there's some slice of the role where you go from full time to part time. You switch your schedule, you work out different hours, you can shift into a district wide role of some kind of consulting. Training new teachers in the science category like you will know better. You will spot these little openings. But something, as Jonathan said, that is just a shift that gives you confidence and starts to free your time a little bit. And then doing this kind of step wise pivot, or I call it an interim pivot, you know exactly what you want to do. Two moves out. You just need one thing in between that's going to help you get there.

Jonathan Fields: [00:26:23] Mm. Love that. So as we wrap up this conversation Jennie, is there any sort of like one takeaway that comes to mind that you might offer, um, up to Megan.

Jenny Blake: [00:26:34] That she's incredible? I mean, her enthusiasm and creativity and what she's already created is so inspiring. And I'm not just saying that to blow smoke or be nice. Really, genuinely. I wrote back to Jonathan and his team and I said, thank you for choosing this question. I love it. And so, Megan, I just want to say kudos for building the business that you are, for juggling all that you are, and for even having the courage to submit a question to this podcast. I think I'm not worried about you. That's my takeaway is I am not worried about you for a minute. I know that as soon as you make this decision, I have a feeling you and your husband are going to be off to the races and you're going to look back and laugh a little bit. You're going to say, wow, can you can you remember how scared we were and how what a great decision it's been on the other side.

Jonathan Fields: [00:27:21] Um, I love that. Um, and I would, I would wrap I just offering also sometimes you have to do your way through it rather than think your way through it. And mavens can sometimes be in their head a whole lot, but you've got that maker side to you also, which is very, very action focused. So, um, bring that into the experience. You've been doing it clearly already because you're building something, but continue to think about, um, decision making by doing as much as by thinking. And we're going to call that a wrap for today's episode of SPARKED. Thanks so much, everyone. Hey, so I hope you enjoyed that conversation. Learned a little something about your own quest to come alive and work in life, and maybe feel a little bit less alone along this journey to find and do what sparks you. And if you'd love to share your own moment and question with us, we would love to hear from you. Just go ahead and click on the submissions link in the show notes to get the details on how to do that. And remember, if you're at a moment of exploration, looking to find and do or even create work that makes you come more fully alive, that brings more meaning and purpose and joy into your life, take the time to discover your own personal Sparketype for free at sparketype.com. It'll open your eyes to a deeper understanding of yourself and open the door to possibility like never before. And hey, if you're finding value in these conversations, please just take an extra second right now to follow and rate SPARKED in your favorite podcast app. This is so helpful in helping others find the show and growing our community so that we can all come alive and work in life together. This episode of SPARKED was produced by executive producers Lindsey Fox and Me, Jonathan Fields. Production and editing by Sarah Harney. Until next time, I'm Jonathan Fields and this is SPARKED.