Teachers Make the Leap

Navigating Business Through Life's Big Changes: A Candid Conversation

• Hillary Gale

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In this episode, Hillary and Kristin have an honest conversation about managing a business during major life transitions. Hillary shares her experience being on maternity leave with her second child, discussing the complex emotions of stepping away from business while caring for a newborn. Meanwhile, Kristin opens up about making significant pivots in her business model and the challenges and rewards of decision-making as a solo entrepreneur.

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Welcome to Teachers Make the Leap, a show that empowers educators to build online businesses they love and revolutionize the way work shows up in their lives. I'm your host, Kristen. And I'm your host, Hillary. We're two former teachers who have successfully made the leap from classroom to entrepreneurship. If you dream of finally leaving teaching to be able to make your own schedule and increase your earning potential, join us each week as we explore real ways to get there through online business.

Hillary:

Welcome to this episode of Teachers Make the Leap. Today, Kristen and I are going to have just kind of a candid conversation about how some things in business can feel really hard. I'm still on maternity leave right now. I'm enjoying time with my newborn and my 2 and a half year old, and some things about my business are feeling really, really hard. but there's also a lot of things that we're really grateful for. Even when we're feeling those hard things. So we're just going to have a conversation about, kind of what that feels like and what that's been like, for both of us in our different seasons of life.

Kristin:

Yeah. And I think talking about things like this is really important because a lot of business building talk and, um, you know, starting your own thing can tend to feel really sparkly and shiny and We can, we can honestly just tend to glorify all the good things because there's so many good things. And also, I'm really appreciative that we're going to dive into some of the things that feel really hard today. And I know Hillary, you're on maternity leave. And I think that's probably a great place to begin in terms of, you know, going through something in life. that you're really grateful for to have some flexibility. And I'm sure there's hard aspects of that as a business owner as well.

Hillary:

Yeah. And I will say, you know, this is my 2nd time around on maternity leave as a business owner. And so I think having that perspective to, um, Of like a lot of the feelings that I'm feeling right now are feelings that I felt on my first maternity leave and during that first maternity leave, I had no sense of if those feelings were permanent, or if they would ever go away, or if they would change and they did, they did change, you know, the further I got into postpartum and things like that. And so that's really helpful for me this time around. I'm like, oh, these feelings that I'm feeling that are kind of scary and. Yeah. Term oily and, you know, that kind of thing. I know that they're not going to last forever, right? This is familiar territory for me at this point. but it's still uncomfortable and it's still, I think, worth. acknowledging and talking about and just kind of, being real about it.

Kristin:

Yeah. So if you don't mind, can we impact some of those feelings that are bubbling up? Some of those turmoil y, scary things that feel familiar at this point.

Hillary:

Yeah. And just to give some context to this, I am an Enneagram type three, which is the achiever, which means that I, I love Work, right? I love what I do. I take pride in success. I, I'm kind of a perfectionist. I feel guilty if I'm not working, you know, all these kinds of things. And so these feelings for me, my first time around, in maternity leave were really surprising because the feelings I were having were like, I never want to go back to work. I just want to spend all of my time with this little person. I want to burn my business to the ground. You know, just, you know, Just these feelings that I had never had in my life before were all of a sudden coming up and they were really preventing me from, wanting to go back to work, wanting to work on my business, all of these things. And, it was a also kind of a weird feeling because I was taking three months off, whereas a lot of my friends who had had kids and we're working, you know, I have a sister in law who works for the state. They were, they were getting six weeks off and then they were going back to work. And so it's kind of. Strange, I suppose, in this country to say, like, well, I'm going to take 3 months off. And yet that still feels like not nearly enough time. I'm still totally dreading going back to work. Why am I feeling this way? and so that's very much how I'm feeling right now. My baby's about to turn, 12 weeks next week. And so I feel like, you know, logically, I should be getting back into work mode and I should be excited about going back to work. And, you know, I'm questioning why am I not feeling that way? But. It just kind of is what it is, I think,

Kristin:

Yeah, that makes so much sense. And I appreciate kind of your honesty and candidness in terms of like, maternity leave Is an interesting space, it sounds like, since I don't have children, but just kind of repeating what you're saying. It sounds like maternity leave is an interesting space where your priorities are shifting around. And even if you are an Enneagram 3, or like, really thrive in work and really love your work, you can still find yourself in a space where. You're not craving work at that time. And I think that's probably really normal especially when you just bring a brand new baby into the world.

Hillary:

right? And I think that's part of it, too, is when you bring a brand new baby into the world, you know, it is work, right? And so I think that's probably where a lot of that comes from is, oh, I just want to give all of my work energy and all of my focus to this little child that requires so much of me. So it's really hard to imagine then splitting up my time between this child that still needs me, I would say, 16 hours out of the day. And then this business that is also in a way, kind of like a child that I brought into the world and that requires a ton of work and a ton of oversight. Right. so yeah, I think it's just hard to try to split your brain into caring for two things that really, really need you. Not to mention when you, like me this time around also have a toddler who also needs you all the time. So it was just this really interesting space and you said something to, how in this country specifically, We're expected to go back within 6 weeks. And if we take 3 months, people are like, wow, that's great that you can take that much time off. But 3 months still isn't enough. And you and I have a mutual friend and and you said, you know, she was just talking to you. She had a baby earlier in June and she said, you know, she didn't really feel like she was even remotely ready to go back until about 5 months. And I think that that is just really also important to acknowledge is that. Just because the corporate world or whoever, whatever world tells us you should be ready to go back in six weeks or three months or whatever it is. That's definitely not the case.

Kristin:

Yeah, and I appreciate too, and want to acknowledge that everybody's journey is fully different and there's that timeline is different for every single person when they feel ready to either go back to work or shift their attention away from like brand new baby.

Hillary:

Yes, absolutely. And I think that that's what I love about being a business owner. Is that, you know, I told myself I was going to go back after three months. but when I do go back, it doesn't have to be full time, right? It can be something like four hours every day, or it can be six hours or every day can look totally different. And so That's one thing that I really am grateful for, even though this time feels hard and I'm having feelings like. I want to burn my business down and things like that. I'm just so grateful for the fact that, I do have some more choice here and that's just such an unexpected perk, you know, of being a business owner and, I guess just not being tied to someone else's expectations and really just only having to manage my own expectations.

Kristin:

Yeah, and this reminds me of kind of one of these really cliche quotes that I'm sure everybody has heard all over the internet and in books and stuff, but it reminds me of, you know, the quote of choose your hard, where no matter what path you end up trudging down in life, it's going to be hard, right? Nobody can remove the hard, the hard aspect of your choices. And, with a nine to five job, whatever that is, there are certainly hard aspects of that choice, right? In that path, you know, being tied to somebody else's schedule or having to show up at a, a particular time that you didn't choose, having to meet maybe KPIs or metrics or report to somebody above you or ask for permission or, you know, needing to kind of plan and plot your, um, Time off or when you want to take a vacation or when you're allowed to take a vacation at the same time. There's there's stability that comes with that, right? There's predictability. There might be a promotional ladder that, you know, so, you know, exactly when you're going to get a raise or when you're going to get a bump in pay or responsibilities. So there's a predictability to come back to that word inherent to the 9 option in the business building option. There are also pros and cons. There's. so much freedom and flexibility to be found that it's almost overwhelming. You get autonomy, You get the ability to choose who do you want to serve? What niche do you want to be in? What do your services look like? What are your prices? How much do you want to work? what weeks do you want to take off? Like all of that is up to you. You do not have to answer to anybody, which is amazing. And there's those hard aspects too, which is, You have to steer the ship, You have to pedal the bike, so to speak. So all of your forward momentum really is up to you, which is scary and also exhilarating. And there's a whole roller coaster of emotions kind of packed into that, but it really does. Just what we were talking about. Remind me of of the choose your heart. There's so much good and so many hard moments to be found in no matter what path you choose.

Hillary:

Yeah, you know, it's funny to hear you say all of this because What I'm experiencing right now is kind of just these conflicting emotions, There's on 1 side. There's this. Intense gratitude that I'm able to take off the time that I want to take off and then I can ease back in whenever I want to. And then on the flip side of that, there's also almost this desire for someone to just be steering the ship for me for once, Because I am kind of steering the ship. Well, actually a two month old is steering my ship right now. Right. And so for me to then have to steer the ship for my business just feels like a whole other mountain to climb. And so there's a part of me that's like, man, I just wish there was somebody who could tell me when to show up and what to do. Just pay me for showing up and, you know, and so that's also kind of an unfamiliar feeling because that's oftentimes something that, you know, I'm so grateful I don't have to deal with anymore. so it's just the whole postpartum journey, I think, and being a business owner, it's just this massive, it's not even a rollercoaster, it's just a, like a, an entire theme park. So I know you too, Kristen, or, you know, even though you haven't brought a child into this world, you're going through some changes yourself in your life. So is this something that you're also kind of dealing with? I'm kind of curious. We haven't really talked about this.

Kristin:

yeah, for sure. and, and I think that everybody reaches points of change in their life, Where, um. It feels really hard to make all of the decisions, right? Like decision making is a fatiguing task. Like you have to spend energy there. So, one of the changes that's happening for me right now is I'm at a point in my business, and I think a lot of people get here where I'm kind of rethinking A lot of my business. What do I offer folks? What do I want to be offering folks? What are my price points? Are those serving me anymore? How can I raise my prices, but still offer something really premium and valuable to my clients so that I can earn more or you know, hit my income goals? So I'm at this point of pivot where I'm doing some growing in my business, and that feels really hard. there's nobody steering the ship, right? I'm the one steering the ship. And it's funny because that, that double edged sword is super present for me right now, like you were just talking about, where I'm so, so, so grateful to be able to make my own decisions. And like, for example, last week, I took an impromptu trip to LA with a friend of mine because we were really craving some like sunshine and ocean views. So that's what we did. and we did it on a budget. It wasn't like I splurged on kind of a huge vacation, but I had some flexibility where I said, do you want to go to LA for a few days? That sounds wonderful. Let's have some good meals. Right. That's just really what I needed. I was able to say yes to that. So, so grateful for this path that I've chosen. That never goes away for me and also it can be very difficult to make all the decisions over and over and over and over again. Right? Nobody's making the decisions for you and with making decisions. We talk about this on the show a lot, but with making decisions comes. A lot of second guessing, a lot of having to really have faith in what you are choosing. a lot of what ifs, a lot of projection. There's just, there's so much kind of mindset stuff that come up when you're making decisions. And as I'm kind of going through this mini rebrand, I'm going to call it, in my own business, I'm left with all these decisions. And not only, you know, Do you have to make the decisions, but then you have to bring those decisions to life, So when I decide, Oh, my signature offer that I offer my clients for the past three years is going away and I'm redoing that. Then I really have to put the legwork in to, to actually bring that to life. Right? So yes, I'm doing a lot of personal growth in my business right now. It's changing. and that's a normal part of doing business. But it, it doesn't make it easy, right? It's, it's a choose your heart moment. It's another one of those.

Hillary:

Yeah, it really is. And one thing that you said, I just kind of want to circle back to you because I, it really resonated with me is you never stopped being grateful for the flexibility and the freedom that this path has given you. And I, I couldn't agree with that more. And I think that's what prevents me from burning down my business when I have a new baby and I'm like, I'm never going great. Right? Because. And my ideal world, I would be independently wealthy and I wouldn't have to work at all. And I would just, you know, volunteer and spend time with my children and it would be great. But that's not the world that we live in. Right. And so I think that is truly what keeps me going and steering the ship and saying like, okay, I'm going to get back in front of this home. Right. Because I do love. What it has given me, even though sometimes it scares the shit out of me, like to be perfectly frank. And I think that's what it comes down to is like, sometimes it just feels like the scariest thing in the world to be a business owner.

Kristin:

Absolutely. And I, I do think that this is kind of a funny nuanced situation I'm wading into, but I do think that a lot of folks don't realize How, the, the choose your hard, you know, when you start a business, because by nature, so many of us, especially if we're coming from a place of burnout, we're looking for guarantees, right? We're looking for the easiest path downhill. We're looking for, the path of least resistance, essentially, how, how can I get what I want without hitting this wall of burnout over and over and over again. And. A lot of times the business ownership route can appear super, super rosy. and that's because there are rosy aspects of it. I know I said this earlier. but it's definitely a fair point to, to say, if you're thinking about starting a business or if you're new to business, feeling the full spectrum of immense joy. Gratitude, terror, hesitation, frustration, fear. Like the whole spectrum, feeling those things is a feature, not a glitch. as the kids say, right, it's exactly what's supposed to happen. It's, it's normal. now when I first got into business ownership, I'm not quite sure I even really appreciated. The, the emotional nuance and rollercoaster that, you know, would come along with the journey. Um, and, and honestly, this is kind of funny to say, but I think in hindsight, I'm glad that I didn't overthink it. Like, I'm glad that I just went with it. Um, and, you know, dealt with those emotions and those things as they kind of came up, because maybe I would have scared myself out of, out of walking down this path, if I would have known in the beginning, the emotional, you know, kind of turbulence, so to speak, that comes up with starting a business.

Hillary:

Right. Oh yeah. I think that's such a good point because I am definitely someone that can talk myself out of things, you know, and, and so I actually too, I'm kind of glad that I didn't know, I guess how hard it could get internally, you know, and, and just how much I would have to, I don't want to say fight with my brain, but how much I would just have to wrestle and work with my brain to keep going. Right. And, and I think that truly that ability to just take each day as it comes, I can credit that. Yeah. To the fact that I'm here today, four and a half years later, still a business owner.

Kristin:

Yeah. And it reminds me again of what we talk about sometimes, which is that the best way to exist in this space of owning a business is to think about the long game, right? Is to really kind of be rooted in the long game. And I, yeah, I think we can really start to convince ourselves out of things when we look at things in the micro. I don't feel like showing up today, so I should burn it all down. I don't feel like showing up for four weeks, three months in a row. So you know what, this is true that we got to like jump ship. I don't know how to make this next decision, so let me go look at jobs. You know what I mean? There we, when we react to the micro, it can just mean we're. Not thinking about the long game, and I do think that in the long run, if we can keep showing up through those emotions, through those doubts, through decision making, if that feeling of gratitude undergirds kind of everything, then the long game is going to play out for us because that's what we're banking on.

Hillary:

Yeah. I really love that. You just said that. cause it's so true just because I don't feel like showing up for three months doesn't mean I'm not going to feel like showing up. three months from now. and I think that I, again, just kind of going back to, my experience, I'm so glad this is my second time around that first time around, you know, postpartum was so scary. and this second time around is just a little bit less scary because I've been through it and I know that the feelings will just pass. So, I have actually found this conversation to be really rejuvenating and like, okay, you know what? I think I am ready to get back to it in a couple of weeks.

Kristin:

that's awesome. Thank you to everybody who tuned in. Hopefully everybody got, uh, to take away a little gem from this behind the scenes conversation of. how to kind of choose your heart in business. thanks again to all of our listeners and we'll catch you next week on the next episode of Teachers Make the Leap.

Thanks for joining us on this episode of Teachers Make the Leap. We can't wait to help you make the leap from teacher to thriving business owner. If you liked what you heard today, subscribe to the show on your favorite listening app and leave a review on Apple Podcasts. We'll see you back here next week.