Teachers Make the Leap

Year-End Reflections Part 2: Embracing New Growing Pains

• Hillary Gale

Share episode

In par two of their year-end reflection series, Kristin and Hillary dive deeper into the challenges, learnings, and transformative moments that shaped their 2024. From navigating business evolution to finding comfort in discomfort, they share honest insights about their entrepreneurial journey.

Hillary's Year-End Reflection Questions:

  1. What was an unexpected joy this past year?
  2.  What was your favorite book you read this year?
  3.  What was your favorite movie or TV show?
  4.  What worked out in your favor this year?
  5.  How satisfied were you with your work this year? What did you enjoy and not enjoy?
  6.  What was the biggest thing you learned about yourself?
  7.  What was your biggest challenge this year?
  8.  What is one magical moment that made you feel alive or grateful or joyful?
  9.  What are three adjectives you would use to describe 2023?
  10.  What will you choose to remember 2023 for?

Grab a journal and your favorite drink and enjoy some focused time of reflection on the year past. 

Want to ask Kristin and Hillary a question? Click here to submit your question to the podcast. We'll answer it on an upcoming episode of Teachers Make the Leap!

To make sure you never miss an episode of Teachers Make the Leap, subscribe now wherever you listen to podcasts.

And to stay in the know about all the exciting things we’re doing to help more teachers leave the classroom to become their own bosses, follow us on Instagram at @teachersmaketheleap or join our online newsletter by visiting www.teachersmaketheleap.com.

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. This is part two of our reflection on 2024 little mini series. In part one, Kristen and I talked about some of the lighter reflection questions that we like to do when we're looking back on a year and we ended up talking for way longer than we thought we would on the lighter side of things. So we thought we would split this episode up into two parts. And in this one, we're going to talk about A few deeper questions, that we, that we really like to do at the end of the year. Just as a quick reminder, I am going to put all of the reflection questions that I like to go over myself in the show notes in case anybody else wants to spend some time journaling, you know, around the end of the year and reflect. Yes, so the

Kristin:

I'm very excited to get to these questions as well. It's been super fun doing the more lighthearted ones and talking about our favorite books from the year and our favorite shows and all that. But let's get into the juicy stuff.

Hillary:

1st 1 that we're going to chat about is what was your biggest challenge this year? Do you want to go first? Okay.

Kristin:

Okay. So personally for me, my biggest challenge in 2024 is I've kind of seen this year as A year of kind of growth and evolution that has been a little bit uncomfortable for me, and what's always challenging about any type of growth is that. Usually you're growing into territory that you've never been in before, it's not like, Oh, I've, I've done this exact scenario. I know what I'll come next. I feel like I'm at a point in business where I'm growing and I'm not quite sure what's coming next. So there's a lot of challenge in trying to trust my gut in creating kind of new offers for my business or changing up my ideal client. Or thinking more intentionally about the packages that I have and how I'm pricing those, how I can reach my financial goals, and what type of marketing, you know, I want to kind of include in my business that feels authentically kind of like me. I think I've learned and I'm still learning all the time, that in business, there are so many options, infinite amount of options. That you can do, or you can try, or things you can implement, I hate to be talking in like, like so conceptually, but, you know, if you're thinking about marketing your business, you could show up on social media, you could have an SEO strategy, you could redo your website, you could create a podcast, you could create a YouTube channel, you could write blogs, you know, it's, it's virtually endless, the things you can try in your business, and that was just marketing, and I think I'm at a place. In my business where I'm realizing that some things, and this is such a nuanced conversation and such a nuanced thing to be learning, but I'm realizing that sometimes you're uncomfortable because you're growing in the right direction. And sometimes you're trying things that are uncomfortable and they're just not you, right? So it's so hard to figure out and you can only do it by trial and error. to figure out what feels uncomfortable, but still right. And what feels uncomfortable and you just want to kind of cut loose and not try that again. So I'm in a place in my business this whole year where I'm trying to figure out what comes next. which is a natural place to be because you're always evolving in business. And I think, we can glorify business and say like, Oh, I just want to create the perfect version of my business. That is set it and forget it. And that's on autopilot. And, you know, it just works for me and I never have to make any changes. And that has not been my experience at all. My business has always required me to actively shift or change or double down or try new things. and I, I'm at a point where I suspect it'll be like that for the long haul. So I'm just, yeah, this, this year has been a challenge for me to figure out what comes next in my business. I've served my clients in the same way for four years or so now. And I'm kind of getting excited to create some new offers and serve people in some new ways. So a lot of questions have been posed this year and I'm slowly making my way forward and, evolving in a way that I think feels right, but still it's, it's a process for sure.

Hillary:

Yeah. There, there's two things I want to just kind of touch on that you said that I think are so important to really highlight. And the first one is that there's infinite number of things that you can try trying to figure out which one is right and which one is just uncomfortable is just, it's, It's like the symptoms are the same, And the hardest part is you often have to give something a good 6 months to a year before you even know if it works or not. And I think that that is the piece that gets people stuck is like, you can't even say if something works or not, unless you give it like time. that's super hard. And then the other thing, like you said, is, you know, Business is constantly changing and evolving and growing, but it doesn't always feel that way, right? Like sometimes there's a year or a peer or even two years or three years or whatever it is where your business doesn't really feel like it's changing or growing. Like you're kind of in a groove, things are going really, really well. And then. The time to evolve and change really like comes at you. And so then to be like, okay, now is the time that like big growth is happening. Right. It can feel like really scary. Even though when you look back at the long haul, you know that it's always been coming to this point too. So

Kristin:

for sure. 100%. and just want to say too, I think growth and change in business can arise for so many different reasons, Sometimes you want to grow and change because things are not working. Sometimes you want to grow and change because your priorities have shifted. Sometimes you want to grow and change because you want to kind of optimize your business in a new way that you didn't have access to or didn't think of, a year ago. So, like, growth and change is always good and it can happen for so many different reasons. And I feel like my year of growth and change is kind of coming from A more introspective place. Like I I'm asking myself, how do I want to serve clients going forward? What does that look like where I'm enjoying myself the most? And they're also getting something really valuable. And I think I've approached my business in the past from a bit of a different lens, which is kind of like, what can I create that'll be most Or, um, you know, what service can I provide? That's really premium tier white glove, you know, to, to attract ideal clients. And now I'm just kind of asking myself different questions. Like, how can I show up in my business in a way? That gives me maximum joy, so to speak, and also serves the client in a way they find really valuable. So yeah, a lot of trial and error, a lot of just introspective questions and, and a lot of growing this year.

Hillary:

yeah, I love that. Well, mine is actually a little bit similar when I was thinking about intentions for 2024. So a little bit less than a year ago, I really wanted to take more control over bringing clients in on a more regular basis. You know, I, I feel like up to that point last year, I was kind of bringing in referrals and bringing in clients passively when they would just stop by. And I wanted to take a little bit more control over my pipeline and, and have some more consistent like work coming in that I could really rely on in my business. And so I put together at the beginning of last year, kind of a more streamlined or more focused marketing plan, which is something that I had never done in the first year. handful of years in my business. And so, I started a podcast for that business in addition to the podcast that we do here. And so what really became my biggest challenge last year was putting myself out there in all these different ways and really kind of taking stances and finding kind of a platform for myself. You know, these are the things I believe about marketing. These are the things that I don't believe about marketing and really like holding strong to those opinions. And I found that really, really challenging because I'm a person that one is not only, you know, very introverted, but one that. Deals with a lot of like self doubt and questioning myself and things like that. And so all of a sudden trying to put myself into a space where I have opinions and I talk about those opinions was really, really, really uncomfortable for me. And it still is. And so I feel like I really had to kind of just bulldoze through those feelings a lot this year and just keep showing up even when it felt really uncomfortable. Like that felt like the only way that I was going to actually do these things that. I wanted to try. and so I think that, you know, I don't know if I have like a good lesson that I've taken out of that. Um, but it was just my biggest challenge was showing up publicly so often. And so consistently in these podcasts and on social media and things like that. And I think what I've come back to is just the same mantra. I know I've heard, I've shared it before on the podcast is that, you know, a good business owner is really just someone who kind of gets comfortable being uncomfortable. And, and that's just kind of what I'm trying to bring with myself into 2025, right?

Kristin:

That is so true. And such a great perspective to have that like a good business owner is somebody who gets comfortable being uncomfortable. That's. So, so true. because when we try different things, it's inevitably going to be uncomfortable at first. And then you, then you have to kind of figure out, like I was just talking about, okay, is this something I want to abandon because it's just not me? Or am I so grateful that I pushed through that uncomfortability because I'm seeing some rewards there. And I just want to mention. Really quickly that two things kind of came to mind, two thoughts. And I had to jot them down really quick. So I didn't forget them. Number one is that there can be this interesting stage aspect of having a business that I think. You know, we don't really sign up for, but whenever you're in business, you have to market the thing that you sell. And sometimes that involves showing up like as yourself to market those things, especially if you're a service provider or a personal brand or something. And. That stage aspect can be a very challenging place for people who are introverts. I absolutely consider myself in that bucket, like you mentioned. And there, there's just, you know, you, you have to figure out how you want to deal with that as a business owner. So I totally relate to, you know, like trying to tackle that aspect of things. How do I grow my audience? How do I Bringing clients, how do I grapple with this sort of stage aspect of marketing? Sort of, but still stay true to myself and grow in ways that are uncomfortable, but challenging, but not something that doesn't align with me personally. So a lot of nuance there and I totally relate to that challenge. And the other thing I really related to from your challenge for this year was sharing opinions publicly and that that's, that's Can be hard for some people and I'm definitely one of those people. for a very long time in my life and probably still have like trickles of this present today. I was very afraid to have opinions because I definitely always want to be somebody who Is open to new opinions. Does that make sense? I want to have an opinion, but I'm sometimes almost afraid if I share that opinion, that I'll change my mind later and then have to kind of backtrack in a weird way. There's so much flawed thinking there and you know, that's a whole box to unpack in and of itself. But I can totally relate to that. Like showing up and having some opinions can be very. Very difficult because a lot of my own behaviors, like, really push back against having opinions or I'm just internally sometimes very afraid that I'll want to change my mind or wait, this is one more big fear of mine that I think is like a core personality trait of mine that I'm afraid that I don't have all the information. So I, I'm afraid that I'm making a judgment or sharing an opinion that is. Uninformed in some very important way and that I'll kind of be like, like putting my foot in my mouth almost.

Hillary:

Oh, my gosh. 100%. I am very much a person that is comfortable admitting that I don't know everything. In fact, I almost think I use it as a crutch where I'm like, I don't know everything and I'll never know everything. And that becomes a really good excuse to not have opinions, Because I am very, very uncomfortable. Thinking that I have all the answers and, and one, one thing in particular comes to mind, I will say, so just to lend a concrete example, so I had a person on my podcast, on my finance marketing podcast, who does things. That I, I just have a kind of a visceral reaction against, Like she is very all about doing cold DM marketing on LinkedIn, which to me is something that one, I hate doing myself too. I hate getting cold DMS from people pitching to me on LinkedIn. I don't like that. I immediately disconnect from them. But she is someone who believes in it so strongly. And so I'm like, you know what? If she believes in it so strongly, it must work. And it's true. Like for a lot of people, it does work. There's value, there's merit towards it. And for that reason, I just have a really hard time coming out and saying, I don't like to do things that way. Right. Even though there's totally valid reasons for why I don't like to do that. But yeah, it's just kind of this warring, this battle of like, well, if it works for some people, that means I can't have an opinion against it, you know? And so, yeah, it's just, it's hard and it just feels like there's no right answer. And I'm a person that really likes to have right answers.

Kristin:

for real. this just reminds me so much of a conversation I have with some of my friends. Sometimes we might have mentioned it on the podcast once or twice. I don't remember, but it's this idea that Folks have fatal flaws that are also their superpowers and before anybody gets all up in arms about, like, fatal flaw and character flaws and all that, it's a lighthearted game. It's supposed to be fun and funny. and it's just kind of like, recognizing in yourself that you have some characteristics or personality traits or tendencies that are at once. Something that is, that can hold you back and can kind of work against you. And also that same trait is also sort of a superpower. Like it can be used to also do really good things in your life. Right. And this is kind of one of those, those traits that I think it sounds like both, we both share where using the lack, quote unquote, lack of information as a crutch to not form or share, you know, Opinions is a fatal flaw superpower. Like, it's a fatal flaw because you want to have opinions, right? Like, I want, I want to be able to share what I think with people. I want to be able to actually have something valuable to say and a perspective that, that adds value to conversations. And I want to share those and I want to be proud of those and it's also a fatal flaw Because you will never have all the information, right? I will never have every single piece of the puzzle to create a two million percent informed opinion. It's like, you know, I'm expecting myself to be a robot, uh, in order to give myself permission to like, say something out loud. So anyway, anyway, really long roundabout way. Just to say, I totally understand that 2024 for you was a challenge to like, have opinions and share them publicly. that's a challenge for me all the time as well.

Hillary:

Yeah. And I, I feel like what I want 2025 to be, and we'll have a whole episode on like intentions for 2025, but what I want it to be for both of us is just like, I think getting more comfortable, saying what we believe and, and, and being okay with the fact that other people are going to have different opinions and that's just the way it is.

Kristin:

I also want to say this out loud so that I I cement it in my brain because I know this to be true. and I know that being afraid to share your opinions has a lot of irrationality around it. Like there's just a lot of fear that drives that those decisions. but, you know, having an opinion and then being open and To changing your mind or to amend those opinions like those, those two things can coexist. Like you can share an opinion and also be open to new information and new perspectives that may make your opinions evolve over time. And I I have to, uh, I think actively remember that more often,

Hillary:

Absolutely. Well, it's so funny. That kind of segues somewhat nicely into our next question, which is, What's something that you learned about yourself this year? Right.

Kristin:

Okay. I think this year, more than most, I've learned that things take time. And I've, I say this because I have always been somebody who Would prefer the sprint over the marathon. Like I'd much prefer going on a hike and trudging up to the top of the mountain in one go, rather than like taking the meandering paths to like, go see a waterfall or whatever, and making the whole day longer. Like I'm just like a let's power through type of personality. And. I think I have leaned into that a little bit, strongly as I've, you know, grown throughout the years. And this year, I'm really starting to like, in my heart and soul, appreciate that consistency over time is how any good thing really happens. And good things take time. which is of course a saying that we all logically understand, but at the end of the day, like I absolutely have been before somebody who would prefer to do it all at once and get it all done. And like, you know, just sit down and hunker down and, power through. but this year has taught me, that. Patience, which is something that I think I inherently have a lot of, but that patience, and work over time, like over a long horizon will take you to places that you've never really even dreamed of going

Hillary:

Kristen, I think that's such Such a good one of, of, of like, just kind of looking at yourself and tempering your expectations of what you want or think you should happen and and equating that with what actually does happen and how long it takes to happen. I think that's such an important lesson. And, you know, I'm trying to think about, I'm trying to put into words what I learned about myself because it's there. It's in my brain, but it's hard to put into words and to quote 1 of our favorite TV characters of all time. Michael Scott. I think I'm just going to start a sentence and hope that it ends up where I want it to end up, That was a paraphrase. But I think going back to what my biggest challenge was and, and thinking about, you know, how my biggest challenge was this continual process of putting myself out there and showing up publicly, I think what I've learned about myself is that might not be something that I ever enjoy, but it's something that I can do. It's something that I can do and that I can feel good about, even if it's something that I don't particularly love or enjoy and that, you know, That's okay. I don't have to love or enjoy every single thing that I do when it comes to my work. in order for it to still be an important part of my work, if that makes sense, because I want the result at the end of it. Right. And so I'm willing to do what it takes to get to the result that I want. And I think that's 1 thing that I learned about myself this year.

Kristin:

That's really interesting. think a lot of business owners can relate to that because as a business owner, you inherently wear a lot of hats and the odds that you're going to love putting on every single one of those hats and working in those roles in your business, you know, the odds that you're going to love all of those is pretty high. Is, is low, you know, there's definitely things you're going to do in business that, don't light your soul on fire. Contrary to what you will hear, you know, on, online. but it's important. I think that this discovery that you're talking about, that if you want, what's on the other side of taking some actions enough, and that is really connected to your, why, and a big priority for you, then you It's okay to do some things that, you know, you're not looking forward to or, or aren't excited about, and I think that a lot of people hit this road bump early on, in particular with client acquisition, when it starts to become time to reach out to clients and that is inherently uncomfortable, especially when you're first starting out. And it's like, Oh, business involves this piece. Forget it. I don't want to do it anymore. But if you want what's on the other side of that enough, If you can really connect with that feeling of I want a successful business and I want to work for myself and I want autonomy and choice of my days and all of those things. Doing client acquisition becomes kind of a no brainer, It's just like, of course, I'm going to do that. It might suck a little bit, but I'm going to do it and, and we'll be fine. so yeah, I just wanted to, to throw that out there to relate to that.

Hillary:

Well, I love this next question. This next question, and maybe this will be our last question, if, if, you know, we kind of start to run outta time. But, um, the question is what will you choose to remember 2024 for? I

Kristin:

This is a good one. I, I think for me, when I look back on 2024, You know how some years when you look back and you're just like, It feels like everything was in bloom, which I think for me was maybe the year prior, 2023. I think for me, when I look back on 2024, overall, it's been kind of a hard year. it just, just personally, and you know, like, there's just been a lot to work through this year. and I think I want to remember this year as a year where I planted a lot of seeds. that will come to fruit in future years. So I would love to just kind of look back on this year starting now and, and think about it as a year where I was just tilling soil, planting seeds and really nurturing something that I know will grow into a beautiful garden in the future.

Hillary:

love that, you know, it's, it's very similar for me too. I feel like I started a lot of new things in 2024 and so that's kind of what I wanna remember it for. I wanna, I wanna remember it. For being a year of trying new things, And not all of those new things panned out, at least not in the way that I thought they would. Maybe they will pan out later in future years. but I also just want to look back at 2024 and be proud of all the new things that I tried, whether they worked out or will work out or not. And, and just kind of being okay with the fact that like some of the things I tried flopped. Right. And that's sometimes just the way that it is. and, and that's okay. And so, yeah, I just, I just want to look back at 2024 is like a year of experimentation and just be proud of that for what it is. And I, and I'm glad that I tried new things and put my put myself out there.

Kristin:

Exactly. I could not relate more. Well, thanks for this conversation, and thank you for sharing these questions with me and with all of our listeners. Again, if you want to answer some of these questions for yourself, or you're curious what other questions Hilary answers in her reflective journaling at the end of the year, go ahead and check the show notes. We'll have the whole lineup there. And thanks again to everybody who tuned in. We'll catch you next time 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.