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002: Overthinking: The Right Time

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Hi, it’s Christina, and this is the complex mind of an overthinking overachiever. This is episode two. When I woke up this morning, I kind of drew a blank. What the fuck am I gonna talk about? Because there’s literally a thousand things to talk about. And the whole concept behind this podcast is to contextualize my mind, but also to create like a safe place for yours. Because I think it can be very overwhelming when we are and chronic overthink and there is no outlet. And so today I want to talk about permission.

Permission is not freely given from anyone, but especially ourselves. I think that there is this, there’s this perspective that if no one wants it, I don’t want it. And if no one sees it all for the better and I would rather shrivel up and RAP before anyone sees me fail. So permission is not an offering available to us over thinkers, but I wanna talk about how to break through that because at the end of the day, one of the most prized qualities of an over thinker is we think a lot.

And so we constantly have new ideas, new concepts, new people in our, like there’s just a lot of newness all the time, which is exciting and also very overwhelming. So today I want to give us permission to create. Here’s the thing. We have seen this all over our TikTok. We’ve been watching this kind of happen since 2020 visually. Obviously it happened outside of it being shared on social media, but I think social media gave us a, permission to try something new.

What we witnessed were humans rejecting the idea of conformity, that life doesn’t have to look this way with full air quotes, and that maybe we can shake things up a bit to see what comes of it. And then we saw lots of different access points to creativity. We saw people out here taking pottery classes, making some DIY art, picking up little hobbies, shit making skits on TikTok when we all know damn well half of us shouldn’t have been making some skits.

I think being in a pandemic we were able to be less distracted by the conformity of existing in America. So we were able to kind of play with what would it look like to throw some clay at a wheel, what would it look like to paint a hallway full of faces if you know you know. What would it look like to become literally a plant head and buy 40 ,000 plants and put them all over your apartment and all of a sudden you’re a greenhouse? What would it look like to crochet, knit a blanket? I’m telling you, we really were like, what does it look like to not just choose work and school? I think the perspective was what would it look like if I didn’t choose obligation? Not that working or going to school aren’t obligations. I think that they are.

I think what came from that time was removing a bit of obligation, removing a bit of responsibility, responsibility to our workplace. I mean, truly, truly our workplace, that’s where a majority of us spend our time, right? And so we have this opportunity to explore other things. And so when we think about permission, my belief is that, because we didn’t have someone else dictating our time, we were able to explore.

And I think in a sense, give ourselves permission to create. And in 2024, what I’m continuing to witness is a decline in permission. While not in the same way we were, we’re not. I think that in 2024, what I’m experiencing, what I’m witnessing, is that there’s a decline in permission. And when there’s a decline in essentially choosing ourselves, you start to wonder who has control. Because when the world shut down, in a way, we regained control of ourselves. Choose the things we like, decline the things we didn’t, choose our time, navigate what’s best for us.


Not the betterment of a workplace, not the betterment of your boss, not the betterment of your partners, not the betterment of shit but yourself. And so four years later, we’re watching a decline because in some ways we don’t really have a choice, right? Many of us were not able to just stay home and work. We’re still living in like the romanticizing of what 2020 brought us.

Not that it was romantic at all, but it did what it did for us. And so we’re navigating this new way of existing, right? Four years post pandemic and a yearning to still be creative, a rejection of conformity. I think that we need to inject a bit more of that permission -based creativity that I truly think has gone on a decline. I personally see it every now and then from the people that I follow. So my circle, still trying to access semblances of freedom, not needing to create for financial gain, right? Or if you’re like me, you have a bevy of ideas, like ideas come to you all the time. And sometimes the most important thing is to choose one and just try. And so what would it look like to give yourself permission to just try?

I think the thing that comes up when you’re talking about permission is the idea that if I can’t guarantee this could be a business or that I would be any good at it, I don’t want to try. And I’m not saying that you need to become a ceramicist tomorrow. I’m not telling you to launch your sticker collection on Etsy today. I’m not telling you that you can be a creator overnight. What I am telling you, is to try.

I think we have all these little passions that come up for us, all the ways that we can express ourselves creatively. And I just want to give us permission to try, for you to really trust yourself enough to give yourself permission. It may not be a new business venture.

It may not be a financial gain. It may not be anything, but the goal is to try. I’m going to give you an example. So in the pandemic, I got really into expressing myself through art and feeling before that I did not think that I could have access to being creative with a paintbrush or paint or fucking markers. But for some reason the pandemic gave me permission. I gave myself permission to to do that.

So I like had this idea. I have been working on these like little faces and I’m not a good illustrator by any means. And so what I am really good at is writing. I really like my handwriting. People like my handwriting. So I said, okay, that’s what I can utilize is letters. So the letters were E for eyes, D for mouth, J for nose.

And I just kept repeating this process, plain, truly just plain. So I decided to take that idea and turn it into art and put it all over my hallway, I had a really long hallway in my apartment, and I painted all these little faces like it was wallpaper, and it kinda just became my thing. And it was a fun little video I made for Instagram, but really it was like this cool feature of cheap art in my house. And I loved it.

And then last year, I took that same concept and started really playing with what faces could look like using the same method of writing. And I was able to create a completely different face and I was able to paint it, like really paint full scale. The one on my wall, I think is like three by two feet, something like that. And I just started painting them on big canvases and a friend reached out and was like, I want to commission like a series of three paintings paid.

And here’s the thing, that freaked me out one because this was just like me playing, but I was giving myself permission to play and let other people see me play, which resulted in someone paying attention and someone wanting what I was creating. And so if I relate that to permission, had I not given myself permission to play, I may not have found something that I really enjoyed was very cathartic and could actually be something that could be something.

Now, clearly I’m not a painter. I’m not an illustrator. I’m not out here struck in my eight by tens. You know what I mean? But it allowed me to see that I’m capable of more than just one, entertaining people, and two, educating people, which are the two lanes I’ve been in for 10 plus years.

So when I’m speaking to folks who are really struggling with I don’t know what to put out there. I don’t know what people will be interested in. I don’t know. I don’t know. It’s the simplest request, but it’s the hardest to accomplish is to just do it, to just try. Here’s another example. So when I launched my first company, Jigsaw, in 2016, it was 2015 when the idea was formulated. 2016 was the first event.

It went as well as I think it could have without anyone having any idea who I was. All that they knew, they being the audience and the attendees, were this messaging aligns with them. The concept was a couple of things, get shit done, women who hustle. It was like aligning with the times.

We could go out and build our own businesses. And so, and under this like helm of like, jig+saw will help us help you resolve the four pillars of your business so that you can just be creative. Okay. So that was 2016. That was in like May. And there are two things that happened. One is Jig+saw was not making money, obviously, because it was nothing yet. It had just been an event.

So I, at the same time, was building an agency, like a Facebook ads, acquisition agents and I worked with a lot of DTC brands for their Facebook and Google advertising. And that became the bread and butter to continue Jigsaw. However, Jigsaw did not really have impact until the end of 2016. So seven months later, we didn’t open doors to our first physical space until February 2017. I can tell you at the time, I thought it was a failure.


I can tell you at the time I thought that this was not working. I could tell you at the time I was probably in like the 20th investment pitch at that point. I was traveling a lot, seeking investment, trying to build the big vision of Jig+saw. And that’s why I emphasize MVP all day long. I believe you needed proof of concept to really garner not just brand awareness, but attention from investment. They need to see you in operation that it’s not just an idea in your mind. Some, some do. That’s not what we’re here for.

So I had taken, I had like $2 ,000 in my savings and then I did a friends and family like Venmo request essentially. I reached out to all my friends and I raised another $2 ,000. So I opened my first space with $4 ,000 and I hated, I hated the concept. I knew building coworking was a vessel for something else, but I didn’t know how to translate it.

And I stuck with it, right? Because if I want to double down on my ideas, I’m going to double down on them. I knew it would come to me at some point. So when we talk about permission, I had no real experience in building a business. I would only been a part of startups and like the inner workings of it and fundraising for it and being scrappy. So I took that same mindset and built my own business.

Now I was constantly giving myself permission to keep going. Even when I thought it was failing, even when I felt that no one gave a shit, even when I thought that if I just had investment, this would actually work. That was my continuous mindset, which is why I was fundraising a fuckton and having doors shut all the time.

So what I’m talking about creating, I had no, there was no justification for me to get be offered a free space, a free tendency to open up the first iteration of Jigsaw. Because people saw me doing, it was just given. And then, we opened doors and now the real game started, which was figuring out how this was a business model. So co -working wasn’t it. What really landed were events and education. So that became the forefront of the business. 70 events later in our space, it felt like we had, I had found like a, yeah, this is momentum.

And there were a couple other things that we launched inside that. We had launched something called HerLab, which was thinking of it like a database of creatives and entrepreneurs and specifically service providers to create this intersection of I need a graphic designer, I need a product designer, I need a copywriter, da da da. And you would just come on the platform and find the woman you wanna hire. It was a great idea. I didn’t have the technology. I was building it through Squarespace. I didn’t have the technology to really build it. But anyway, there was lots of ideas coming from the home of Jig+saw.

Now, two years later, I shut it all down because…

What was making money was the agency and I couldn’t funnel any more money into a business that I hadn’t really had. There was no idea left. So one of my students is an incredible athlete, truly incredible athlete. And I’ve watched her build in many different ways, but her constant North Star is community. And so while she’s been able to build a business with like brand partnerships and things like that,

She’s starting to build what it looks like as like her, her name as like a standalone business, not attached to a brand. And I just looked at her, like her broadcast channel and it’s at almost like 700 members and she only opened doors in February of 2024. It is a reminder that if you want something to happen, if you know, I really want this idea to be out there. I’m just really afraid of what people will think.

You really do have to try. You really have to find this like, you have to release the fear. The fear is gonna be there, but release it as its North Star because fear can’t possibly navigate you. Your ideas can, your creativity can, your purpose can, but fear will constantly hold you back. I have put a poll a couple of weeks ago on Instagram that was like, what’s the thing that holds you back from launching your idea?

And… the number one thing was that there will be crickets. That’s the fear and it’s trust. I get that. I get that. Coming back to Jigsaw’s Instagram, which is now Huddo, and having been gone for four years and being like, hi, I’m back. Do you care? Was so scary. But had I started over, it might’ve been a different experience. But had I not in general, I would have never seen this business evolve into what it is today.

Had I not done it, had I not been so secure in what I was building that yeah, I might lose and I have, that’s not my concern. I am, I would much rather lose and have people who are really invested than have an astronomical amount of following and subscribers and have no interest at all. I just like have people just peering through the curtains. What I hope for you is at minimum, you put it out there.

You don’t have to make a big splashy campaign. All you have to do is be seen trying. I’ll close in a minute, but there’s another student of mine who has a subsec and it’s really good. And when she entered one of my programs, she hadn’t written, I think in like months, months, but the writing was really good and she had a very substantial following on subsec.

She just wrote her first post in January that she was like being back. And I think we think that no one sees us and that no one cares. And not that we do it for people to see us or for people to care. I think it’s a, it’s like a cause and effect. If I put some, if I put some shit out there that I’m passionate about, somebody might care. I’m not hoping that someone cares. It just happens that way. And her writing created connection with her community after being gone for so long. That happens all the time.

And we sometimes can feel apologetic about leaving and she didn’t offer apologies, of course. Thank goodness. But I think we tend to do that as like, I’m sorry I’ve been gone for so long. Sorry I’ve been away for two weeks. I’m sorry, I’m sorry, I’m sorry. All that they care is that you’re back and they get to watch someone that they love to witness do their thing. So I think we can remove a little bit of the pressure of like what it means to put our ideas out there, what it means to be creating fully.

If I could leave you with one thing today, whatever the idea that you’ve been noodling on, and maybe it is that you have no real experience, i .e. me painting, maybe it is a vertical of your business that you’ve never tried before, I hope that you just try. Let me define trying for you because I think this isn’t gonna translate by me saying just try.

Trying can look several ways. Trying looks like talking about it, talking about it out loud to your close circle, to your partner, to your family, to the internet. Talk about it, one. Trying number two is be in action about it. So if you’re feeling like, well, I talked about it, now what? Start showing the doing.

So we talk a lot about co -creation, right? This is that. When you’re in co -creation with what you’re building, let’s say you want to open up a plant shop, but you’re not an expert at plants, be seen trying, AKA, showing the try is you curating plants and showing them on Instagram and sharing the things that you learned about this plant and that plant and showing how you nurse the plant back to life and how to repot and so on and so on and so on until you become an authority in your niche. And I try really hard not to use these fucking marketing words, but it is really that. People love POVs.

We can follow as many plant people as possible but we’re following them for a specific, very nicheed B of E. Here’s what I’m gonna leave with you. I don’t know where you’re at. I don’t know in what part of your journey you’re at. I don’t know what you’re struggling with, but if you’re like me, you’ve been overthinking where to begin. So I’m gonna give you a scenario and I want you to try to apply it to yourself. You know you do not want to work a nine to five. You know you are creative. You know you want to provide a service.

You’re just not sure which or what or how. So, and there’s a bevy of services under the world of service provider. Choose one. Choose one that you’re really passionate about. Maybe it’s newsletter, email marketing. Maybe it’s acquisition like me. Maybe it’s content creation. Maybe it’s copywriting. Maybe it’s website design. You’re finding your niche. You’re finding the thing. Choose one, get really invested in it. Like, let’s take email marketing, for example. Start looking up how MailChimp and Flodesk and Flavio, but start looking at these platforms and spend time on YouTube.

What are people saying about these platforms? What’s really exciting about these platforms? What’s not? And then as you start to educate yourself, start talking about that online. Start talking about your POV on some of these platforms and then start to formulate at some point your niche. For example, if you were like, you know, I really like Flodesk, I like how it’s functioning, I think it could be really great for first time entrepreneurs who need to have a newsletter, who need to have some email marketing, and I think this could really be a service I could offer because I can teach them how to story tell through email marketing. And so maybe you build your first service.

And in the meantime, you’re educating your community, even if it’s 500 followers on Instagram, your POV on email marketing. And specifically, maybe you’re talking about the new things that are coming out with Flodesk. I mean, you are becoming the expert as you’re learning. And at some point, at some point, someone’s going to say, I really like your perspective. I really want to understand how I can do this or.

I really want to work with you because you’re resolving a problem I didn’t realize I had, or you’re so educated on flow desk and I know nothing about it, can I hire you to run my email marketing? It’s just choosing the thing, choosing one of your ideas, doubling down on it, be seen trying in it, and eventually turn it into a service or a product or an offering or an extension of your business. This conversation is not create to create, that’s for another time.

This is to create for the hope that this could become a business, for the hope that you could quit your job, for the hope that creativity could pay your bills. When we started, we talked about giving ourselves permission to create and exploring what that could look like, right? Now, let’s take that permission, start to create, find out what we really like, turn that into an offering. Even if that offering becomes, you’re gonna start selling ceramics on Etsy and see what happens. And if you fail,

Always remember that failure is not an end all be all. Let me be an example to that. It’s just the next step. This was a hard episode to talk about, mostly because it’s asking you to really lean into something that feels extremely uncomfortable and likely feels impossible.

Because how can we take the thing that we really find so exciting for ourselves, but have no belief that people will want it, pay for it, engage with it?


We have to get a little uncomfortable. As I talked about in episode one, I do this and I’m uncomfortable every minute of every day. Only because this is new for me. I’m still doing it because I know the end result is something I can’t even imagine. I hope you enjoyed today’s episode. If you follow me on YouTube long ago, I used to sign off with a very specific sign off. So I’m gonna bring that here because it still has so much meaning to me. So go out, get coffee on your lunch break and go connect to someone in real life. Because at the end of the day, that’s all we have. I’ll see you episode three. Bye.

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Welcome to my podcast; a love letter and a space for the Overthinking Overachievers, the Overwhelmed and the Over-Ourselves-Being-Stuck.

“What I hope you gain from this podcast is to feel a little less alone in how you're processing building your business, creating your side hustle, quitting your job, lighting your life on fire and starting over.”

(The HDDL Podcast)

The Complex Mind of an Overthinking Overachiever

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