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159 – All The Things We’re Working On Right Now

Wandering Aimfully Through Our Podcast: What is it all for?

159 – All The Things We’re Working On Right Now

Ever wonder what someone is working on in their business? Here's what we're working on with WAIM and Teachery in Q1 of 2023.
Jason ZookJason Zook Jason ZookJason Zook

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Jason Zook

Listen to our full episode on All The Things We’re Working On Right Now below (with full transcript) or find our podcast by searching What is it all for? in your favorite podcast player.

Key Takeaways for All The Things We’re Working On Right Now

1️⃣ What we’re working on with this site: Wandering Aimfully (WAIM)

New WAIM Members-Only Dashboard

When we say dashboard, we are referring to an internal interface that’s basically a small “app” we built for our WAIM Unlimited members. In the WAIM Dashboard, you can save our resources (courses, workshops, coaching sessions, etc), mark resources completed, add notes, find other WAIM members, edit your profile, and more. One of us (that’s Caroline) is redesigning the ENTIRE INTERFACE! Our dashboard is almost 5 years old and is in desperate need of an update to improve the user experience, searchability, and overall freshening up of the design.

👩🏻‍🦰 Caroline’s Tip: If you want to update something within your offer or your program, definitely talk to your existing customers and see what they are having trouble with in the current experience that you can include in your update. Also, invest time in learning skills! You won’t regret it and I’m so glad I learned UI design and Figma back in 2020.

Client Off-Ramp Operating System (OS)

If you are a freelancer working with clients, but you’re feeling very hamstrung by the lack of flexibility (you’re trading time for money and hitting that income ceiling) we know how taxing that can be from a mental health perspective. If you’re craving more flexibility and freedom, we are building a new Notion dashboard, called the Client Off-Ramp OS. It’s an entire Notion system that’s specifically tailored for freelancers trying to shift to digital products. It’s a dashboard that will help you better keep track of your clients and make your processes more efficient so that then you can carve out the time and start building an audience and selling digital products.

New Articles (aka Narticles)

We talked about this in our 2023 preview podcast episode. At this point, we have about 130 published articles on the Wandering Aimfully website that are helpful, but they’re kind of all over the place. We want to improve that! The idea is to hone in on what eight to ten high-quality articles we can write (our “foundation articles”). Then, the missing piece is going to be, how do we amplify those new articles? We want to find out whether an article strategy can still be incredibly beneficial to your business in 2023 without being on social media.

👨🏻‍🦲 Jason’s tip: Put yourself in the shoes of your ideal audience member. Answer this question: “My ideal customer is so-and-so, they land on my website, can they IMMEDIATELY find resources that help them with their problems?” That doesn’t mean go to your blog and search or dig seven pages into your website, it means, on your homepage, in your navigation, how is that person getting their problems solved?

New WAIM Homepage

Our previous homepage served us very well but we, as people, change, and our focus changes! We want to transition from an extremely simple homepage design to one with a bit more fun, uniqueness, and a new lead magnet. We mentioned in a another previous podcast episode that we did this Behind the Build LIVE experiment. In that live project, we executed on the idea of creating a new homepage and a new lead magnet that was more targeted to freelancers transitioning to digital products. We just thought, let’s try to complete this in one day and have people watch us and watch our process. And it was a really fun experiment! We didn’t complete all of our tasks on the day that we allotted, but we got ~80% done. And now, a few weeks later, our new homepage is done and up!

Un-Boring Group Accountability Game: WAIM of STONES

The way we’ve offered accountability in WAIM Unlimited the past three years is that I (Jason) would exchange DMs with our members, 1-on-1, every Monday. This accountability system was very helpful, extremely personalized for each member, but it was also verrrry taxing on my time.

This has changed in 2023, and we are now running a fun, un-boring, group Slack accountability game we made up called WAIM of Stones. We create a monthly game board, we’ve designed a logo, and we even have silly made-up “WAIM-finity stones 💎” that our members can earn. It’s a weekly accountability system that, while silly in nature, has actually been super helpful in helping our folks reach their monthly goals.

Monthly Coaching Session

We are now at 41 total coaching sessions recorded! When you think about that, in seven more months of doing monthly coaching, we will have done it for four years… straight. The amount of time that we’re investing in the coaching session has ebbed and flowed. From the beginning, obviously, we were pouring more time into every month’s session. It was probably taking us 20 to 30 hours to build a session and a workbook and then to deliver it in a three-hour Zoom call (with an HD recording we create separately). But this year, we have been doing what we call Spotlight Sessions, and they’re a little bit shorter, a little bit more concise.

Oftentimes, as a business owner, you over-stuff your offer because you want it to be valuable. But what you don’t realize is what’s really valuable is saving people time. We needed to break down our coaching sessions in a way where our members can have helpful takeaways in just 45 minutes. It’s not always the time investment or the amount of stuff in a product, but how quickly can you deliver value in terms of them receiving a result or an outcome.

✨ NEW: Private Podcast of our Coaching Audio

This is the first time we’re actually sharing it publicly: we’ve created a private podcast feed of just the audio versions of our coaching sessions. It only took us four years to add that option 😅, but if you’re someone who is looking for more ways to have your content go further to make it more accessible, we think that’s a really smart way to do it. We’ll see how much people engage with it, but we’re just excited to always be thinking about and adding different ways for people to engage with and consume our resources.

Content Ongoing

For our ongoing content, we have our weekly email newsletter, and for 2023 we’re doing 4-8 week series’ around certain online biz topics. For the first time EVER, we have our entire email newsletter planned out for the full year! Our other ongoing content is our podcast, which for now, won’t change very much (but we do have an idea for a shorter, more actionable podcast). And then there’s YouTube… what are we going to do with YouTube? Well, have a strategy that includes our “Narticles” but we’re not making any plans just yet. YouTube takes the MOST amount of time and gives us the LEAST amount of return, so we tread very carefully with it.

That’s it for WAIM and what’s going on in Q1 of 2023, now…

2️⃣ What we’re working on with our online course platform: Teachery

New Trial Signup Flow and Experience

For many years, we had a pretty convoluted trial signup for Teachery. The goal was to help someone answer 7 questions and drop them into their first created course, but it never really panned out that way. Most folks would just type “asdkjsofkpl” in the course fields and then delete the course. Kind of a waste of everyone’s time! So, we rebuilt the trial signup flow, shortened it, and now we drop new customers into an already-created course with helpful tips to learn more about using Teachery.

Basic Admin Analytics

It’s kind of difficult to get truly reliable data these days from Google Analytics, et al. So, for Teachery, we finally created our own admin analytics area and are pulling in some 100% true data from our own logs and database. This new analytics dashboard is just an internal thing, but it will help us better track website visitors, trial conversions, customer conversions, and have a quick glance at our monthly revenue, refunds, etc.


All right, let’s talk about some features that are coming to Teachery because this is really where the rubber hits the road with this little application for helping people build online courses.

Show Notes for Episode 159: All The Things We’re Working On Right Now

This is one of those episodes we wished more people would record. What are all the things currently on the to-do list? How do we manage multiple projects? Who is working on what behind the scenes??

We break down everything we have going on with WAIM and Teachery in Q1 of 2023. We hope hearing some of the stuff we’re working on motivates and inspires you to work on something in your biz! If it does, make sure to send us an email and let us know you want more of these types of episodes. 😘

Links mentioned in the episode:

Client Off-Ramp Starter Kit:

Our plan with Social Media:

HelloAudio (aff link) for private podcasting:

Full Transcript of Episode 159: All The Things We’re Working On Right Now

⬇️ You can also download the .TXT file of the transcript

Caroline: Well, hello there.

Jason: Ooh, it’s a before the episode.

Caroline: It is. This is the pramvel to the pramvel. It’s a short message.

Jason: It’s not a pramvel anymore, by the way, because we’re not traveling so it’s pramble.

Caroline: I really like that word we made up.

Jason: I know. Anyway, let’s get into it. The sponsor is paying us for this time. Go ahead.

Caroline: That’s right. So our sponsor is back, our one and only sponsor of this podcast, and they want us to let you know that our Spring enrollment for our unboring coaching program called WAIM Unlimited opens up for two weeks starting on March 20. So mark your calendars. It’s going to be a two-week enrollment period, March 20 to April 4.

Jason: Yeah. And if you are a freelancer who’s currently working with clients, you want more flexibility and freedom in your biz. You want to move to digital products. This is definitely the program for you.

Caroline: That’s right. We have all kinds of fun things. Monthly coaching sessions. We have some really robust Notion templates for how to run your business.

Jason: We have a full episode about a fun product that’s coming soon for you. And then we also have something new at, in case you’re not on our email list.

Caroline: That’s right. So if you are in the least bit interested, head and sign up for our Client Off-Ramp Starter Kit. It’s kind of like a mini coaching session and a workbook so you can get a taste of some of the things we teach. It’s really just the tip of the iceberg in terms of getting started. Like, if you’re finally, like, haven’t been able to make the time to start building an audience to shift to digital products, this is a great place to start. So, again, head, if you’re interested. And we’ll be back in some pramble to the pramble to remind you. But let’s get into the episode, Jason.

Welcome to What Is It All For? A podcast designed to help you grow your online business and pursue a spacious, satisfying life at the same time. We are your hosts, Jason and Caroline Zook, and we run Wandering Aimfully, an unboring business coaching program. Every week we bring you advice and conversations to return you to your most intentional self and to help you examine every aspect of your life and business by asking, What is it all for? Thanks for listening. And now let’s get into the show.

Jason: And I’m here, too.

Hello there and welcome to the episode. Thank you so much to everybody who sent in Grammy nominations for me for my singing last episode. Our inbox was overflowing.

Caroline: Overflowing.

Jason: With messages.

Caroline: About…

Jason: SAG Awards.

Caroline: Have you gone on the…?

Jason: Tony’s. I was nominated definitely for a couple of Tony. Tony, tony tones as well.

Caroline: One of my favorite thing about you is just that you have just such not a deep understanding of pop culture.

Jason: AMCs.

Caroline: And so… the AMCs.

Jason: AMGs. What is it? What’s the American Music…? Country American…?

Caroline: Let’s say the words. Are you thinking of the American Music Awards? That’s AMA.

Jason: Yeah. That got it.

Caroline: Are you thinking of the…

Jason: I’ll do an AMA right here.

Caroline: Academy of Country Music Awards. That’s ACM.

Jason: Let’s do it. I’ll do it.

Caroline: Let’s just say the words, and then let’s see what the letters are.

Jason: I mean, when you have the singing talent that I was blessed with last episode.

Caroline: It’s hard to keep track of all the nominations and the awards.

Jason: Yeah, I mean, it’s weird to get nominated for, like, a SAG Award when you’re a singer.

Caroline: AGT, America’s Got Talent. You can go on there.

Jason: I definitely got nominated for that. Anywho, that was a silly thing we did last episode, and I’m just referencing it. Let’s talk about a little pramble stuff here.

Caroline: What’s going on?

Jason: With our life in Portugal.

Caroline: In Portugal world. Not much to report. I mean, we’re really getting in deep on the Portuguese lessons. We’re enjoying it very much. I’m so proud of you.

Jason: Okay.

Caroline: Because…

Jason: This is of me, not of the person listening.

Caroline: I am so proud of the person listening.

Jason: Right.

Caroline: But I’m also proud of you sitting across from me because I know this isn’t easy for you, and it warms my heart when we sit down to do our homework and you just stay there and you slog through it, and you practice, even though you might stumble or whatever, but you try again. And I just want to say it’s very gratifying for me to watch you persevere.

Jason: I do appreciate the compliment because I know that you’re trying to give me positive affirmation or trying to coach me up so that I want to keep doing this. I understand, but I will just let everyone listening know. It is hard to learn language as an adult, and I know that there are many of you who, as we’ve been talking about this, have reached out in some capacity. Whether you’re a WAIMer and you’ve reached out in Slack or whether you’ve just been kind of commenting through email or what have you, it’s difficult. Your brain is just, like, hardwired for the language you know. And there are a lot of things in Portuguese that are just close enough that it feels like you got it, but then you really don’t got it.

Caroline: I’m also amazed. I have a lot of compassion for myself. There have been times in the past where I’ve been like, I really want to learn Italian or I really want to learn this or that, and I’ve tried and kind of, like, fallen off the wagon. And I look back now and I’m like, well, no doy.

Jason: Wow. Easy.

Caroline: Because not only is language learning hard, but we have arguably the strongest motivation we’ll ever have, which is that it will make our lives easier.

Jason: Because you live in a country where this is the language spoken. Yeah.

Caroline: You live there. Right. I’m like, no wonder it was ten times even more difficult when I didn’t have an immediate and also here you’re running into people all the time who are speaking it, so it’s a little bit through osmosis as well. But if you’re just trying to learn a language by yourself, not in that country, just for fun or for a hobby or just because you like learning more. Power to you. Congratulations.

Jason: I just thought it’d be interesting for folks who might want to know how much time we’re spending each week on this.

Caroline: Okay.

Jason: And also, we’ve mentioned this in previous episodes, but my personal goal is by the end of a year, one year, I’d like to be able to walk into a coffee shop and be able to have a small talk conversation of, like, how’s your day going? What are you roasting this week? What pastry do you recommend?

Caroline: I have no doubt that you’ll get there based on our current progress .

Jason: Yeah, but to feel confident in it. I know that in even, like, a couple of months, I could probably know the things to say. But there’s a difference between understanding how to conjugate a verb and ask a question in a sentence.

Caroline: And just like…

Jason: But feeling the confidence to respond to someone and not freezing completely.

Caroline: Definitely.

Jason: So, anyway, just to close the loop, what I was going to say is we do a 1 hour lesson with a private tutor through Zoom.

Caroline: On terças.

Jason: On terças, which is Tuesdays. And then we do like an hour and a half homework on Sundays.

Caroline: Domingo.

Jason: Domingo. And then we usually do like, a cram session right before the Tuesday session as well.

Caroline: Now that we’re getting more homework, we didn’t get through all of our homework in an hour and a half on Sunday, and so I did probably 30 minutes last night.

Jason: It’s also one of those things where, like, the Sunday homework for me this week, my brain hurt by the end of it. I just was cramming verbs into it as much as I could and conjugations and wow.

Caroline: It’s a lot.

Jason: Okay. Anyway, that’s the update on the Portuguese lesson stuff, in case you were curious of how that’s going. And then the other thing we did last week was we got to spend a whole day with some Portuguese friends.

Caroline: A whole day with Portuguese friends.

Jason: Yeah. And actually one of which is a WAIMer, which is amazing, Maria, and her partner Rui, which is very difficult for us to say because as English speakers, we just want to say Rui. Like, the R is just Rui, but it’s Rui, which is kind of like the Hvar from Croatia. I haven’t learned that. But it was fun to spend a whole day with people who they’re from here, they know the culture here, and we’re just trying to like…

Caroline: And it was the best, not just from the Portuguese perspective, but also as a couple who works together and have such an entrepreneurial spirit. And it was really fun to be able to have so much in common and talk business, but also talk life and talk about carving your own path in life. And it was cool to blend because sometimes, especially the few people that we have hung out with here, maybe they don’t necessarily are in the entrepreneurial world, but we get the Portuguese perspective, and that’s really fun. Or vice versa. We have entrepreneur friends who don’t live in Portugal, and so it was fun to blend the two.

Jason: Yeah. Maria is also currently on this kick of crocheting, and she went and got photos of her crocheting in front of the dinosaurs because I think she’s making it for one of her cousins or family members.

Caroline: If you don’t know, Lourinhã is known for…

Jason: The town that we live in.

Caroline: The town that we live in is known to be the dinosaur capital of Europe.

Jason: Which is fantastic. And I loved getting these photos from her on WhatsApp of just, like, crocheting in front of the dinosaurs. I’m like, yes, this is why we live in this town because it’s amazing. So, yeah, it was just a really fun day to spend with people. And I think for us, it really has been a long time since we spent a full day with people. With COVID and everything else, it was very draining by the end of it, but it was also I woke up the next day, I was like, oh, wow. We really spent, like, a lot of time just having, like, conversations with other people.

Caroline: And it was fun, and it was, like, so many things to talk about. So that was fun.

Jason: I also got a comment at dinner that I threw out a perfectly pronounced obrigado.

Caroline: That’s right.

Jason: Which little pat on the back.

Caroline: See, that’s what you should… bring that into every…

Jason: I can say thank you well.

Caroline: Every time we go into new Portuguese lesson, you need to remind yourself, like, gosh, wouldn’t it feel great?

Jason: Yeah. All right, so those are our small updates on Portugal. By the way, if you ever have any questions, things you want to ask us about life in Portugal, feel free to send them along. We’d be happy to answer them in our prambles here. We might even do a full episode, maybe a couple of months into living here full time, just to share what it’s been like. if you want to send any questions. But now let’s get into this week’s episode, which is kind of an extension of our goals for 2023 episode, but what the heck are we working on, and where did this episode stem from, Carol?

Caroline: The episode stemmed from me going, hey, you know what a lot of people don’t talk about? Is that where it stems from?

Jason: Yeah. This wasn’t a quiz. You said this earlier.

Caroline: For me, where it stems from is I just wish… I would love to hear more of what people are working on. What do you do every day? What’s going on in your business? That’s the stuff that fascinates me as much as the tips and the kind of general advice is really helpful at times, and it is, the actionable stuff. I also learn quite a bit just from people telling stories about what are they working on? What are their challenges like, oh, that gives me an idea about this.

Jason: I also just get really excited because when you hear what people are working on, it makes you think like, oh, I haven’t been working on that, or that’s the thing that I’ve wanted to do. And this actually got me excited. Now I have momentum and energy to work on this thing, whereas it could have gone by and you never would have worked on it.

Caroline: So we just thought it would be a fun episode to kind of we’re almost two months into the year, give you a rundown of all of the things that we are working on at various times. It’s not like we’re trying to juggle all of these at the same time. So we’re excited to get into it. A couple of caveats. I looked at this list and I told Jason, I’m like, I don’t know, I feel like this might overwhelm people if they listen to it because it’s a lot of things. But I wanted to so before we get into it, I wanted to remind everyone we are coming off of a year of basically not creating anything in our business. It was very much a Sustain year last year when we were traveling full time. We didn’t get to create really anything new. We just were maintaining. And so one important thing to note is we’re coming up this year with an intense amount of energy and creativity and desire to work, which is not always the case. That’s not a thing that you need to keep up with that or that you need to aspire to that at all. It’s more of just sharing authentically that we’re just really jazzed about the business right now. So that’s probably why we’re doing more things. Number two, Jason always likes to remind and everyone that we are two people.

Jason: We’re two people. Yeah. So when you listen to our podcast and you’re like, oh, wow, I want to do this thing that you all are doing, but then you realize it’s going to take you a lot longer than it took us, it’s probably because we’re two people.

Caroline: Yeah.

Jason: So we have double the capacity.

Caroline: Now that being said, we don’t have a team. We do work with some contract help.

Jason: The way you said that was like are they mercenaries?

Caroline: Sorry.

Jason: Every once in a while.

Caroline: Go ahead. What’s the code word that you would use for that?

Jason: Mercenary?

Caroline: Spies?

Jason: Sure. Spies.

Caroline: It felt very code word.

Jason: I was going like the Jack Ryan route and you were going like the spy next door route. Like goofy comedy.

Caroline: The reason I stumbled is because I’m like, what is the appropriate word? Like, first of all, I don’t like… I just didn’t know. Contractors. That sounds so cold.

Jason: For the people that we work with?

Caroline: Yes.

Jason: Freelancers, I would say.

Caroline: Okay. Because it’s not an in-house team.

Jason: Exactly.

Caroline: They’re not working exclusively. They’re not employees and they’re not working exclusively on our businesses. But then I was like, I don’t just think of them as like people who come in and out. So I don’t know. We need to come up with a better word for that.

Jason: Yeah. Anyway, yeah, just to reiterate your caveat, we’re two people, we work with some freelancers, so we’re not always doing every single thing ourselves, especially when we get to the Teachery stuff. There’s a huge bottleneck after us of where our work stops and other people’s work picks up. And then I think the other thing to just remember too, is like, we don’t have kids. We have a lot more time to invest in our businesses right now.

Caroline: Which is also kind of part of the reason that we’re maybe doing more than we have in the past this year is because we know that that’s coming down the pipeline, that being kids. And we know our time is going to be very… this might be the last year that we have to actually put forth this amount of effort towards growing things. So all of those factors combined. So let’s just get into like, what are we working on? What do you want to talk about?

Jason: Great. So the first thing, we’re going to break these into two categories. Here we have Wandering Aimfully, which is our unboring coaching program, which shameless plug is going to be open for enrollment here in just a couple of weeks if you want to check out. And then we have Teachery, which is our online course software. So we’re going to go Wandering Aimfully first. And we call Wandering Aimfully, WAIM. So if you hear us talk about that, we’re not mentioning some guy named Wayne all the time, because I know there are…

Caroline: Despite our transcript that we used to do always with…

Jason: Yes. For our captions.

Caroline: Autocorrect.

Jason: Because I do know that we’ve actually had some podcast growth over the past couple of weeks, which has been really cool to have new listeners.

Caroline: Thank you for sharing the episodes. If that’s you out there, doing that.

Jason: Yeah, it’s really helpful. So let’s start with WAIM and the new dashboard.

Caroline: Yeah.

Jason: So just to give a little bit of context to our dashboard. So what we mean when we say dashboard is a person joins our program, Wandering Aimfully Unlimited, and we have a whole thing built behind the scenes that essentially is like…

Caroline: It’s basically an internal app is what it is.

Jason: It’s a login area. It’s a library of resources.

Caroline: Desktop app.

Jason: It’s a dashboard where you can save things. You have a profile. It’s a whole page of everybody who’s created a profile that wants it to be public. And then there’s a bunch of other like random bits and bobs in there that are like community-only access things.

Caroline: And we created this in 2018 with the advent of Wandering Aimfully because Wandering Aimfully started out not as a coaching program, but really as sort of like a membership of getting all of our access to our courses. So there was a lot of resources to be able to look through. And so we wanted to create a custom experience for someone to do that. Of course, over time, it sort of morphed into a coaching program with sessions being added every month. So there’s still very much a need for that, which is to be able to sort through all of our resources. Now, it became very clear to Jason and I at the top of the year, we knew that we wanted to redo the dashboard. I think we sent out a survey maybe at the end of 2021.

Jason: Well, and I’ll even give the caveat that in 2018, when we finished the build of this dashboard, which cost us just full disclosure, about $30,000 in development costs, when it was done, we had already said in two to three years, we have to redo this.

Caroline: Yeah. Because by the end of it, we were just like, it didn’t turn out to be what we wanted it to be. I think we do have an episode somewhere where we talk about that.

Jason: I’m sure we do. But yeah.

Caroline: It served the function that it needed, which was to allow people to search our resources and save them and to just access them. And so it served that function. But immediately, it’s so disappointing to spend that amount of money on something and immediately be like, well, going to have to redo that in a couple of years.

Jason: But I think it’s a really good example. And we’ve talked about it before. It did serve us well for five years. It does solve a couple of specific problems for our members. And it is a more customized experience as a customer than you get from a lot of other platforms where you just get dropped into a Google doc with a bunch of links.

Caroline: Absolutely.

Jason: So what have you been working on? Because you’re the one redesigning the whole thing.

Caroline: And so we did send out a survey. So this is the first kind of tip I would say, is if, you know, you want to update something within your offer or your program, definitely talk to your existing customers and see what are they having trouble with in the current experience that you can bring that. So a lot of the feedback was searchability and just ease of finding things. And we realized that part of that was the design was so cluttered and so just visually, it was hard to discern between things. So I have been redesigning all of the screens in Figma. And this just as a side note, this is a perfect example of like, no time that you invest in building your skills is ever wasted. So in 2020, I taught myself UI design to be able to redesign Teachery, which is our other business, which we’ll talk about. And boy, was that a hard skill to learn, UI design, because I was already like, but I had to learn Figma, and I had to learn all these tools in order to be able to do it well. But every time I work on doing the dashboard now, I’m like, oh, my gosh, all those hours spent are helping me to do this now. So we always tell people, like, invest time in learning skills. You will never regret it because we easily… redesigning this, paying a designer to redesign it, it would be tens of thousands of dollars.

Jason: Yeah. I think it’s safe to say that this would have been a $10,000 plus just redesign, not to mention the development. So that’s just getting all the things that you’ve designed. And so just to kind of maybe wrap this one up, because we have a bunch of things we want to share that we’re working on. So our goals are we want it to be a lot more usable. We want it to be and in that we mean searching, being able to find things just scalability visually. Like, right now, it’s very visually cluttered because there’s so many colors and images and things, and we’re just stripping a lot of stuff back while still keeping it fun and beautiful, a better design, just overall, like, more actionable things. And it’s the UI stuff that you’ve learned.

Caroline: Also, for a long time, we had our coaching sessions live outside, like, the main hub for where you access all of our coaching sessions outside of it. And that was because when we launched the coaching program, we had two tiers. One was just a coaching tier.

Jason: A six-month program.

Caroline: A six-month program. And the other was you get everything in WAIM Unlimited. And so you might have this in your business where, like, you had a solution that no longer works, because now we just have the one offer, which is WAIM Unlimited. And it’s a bad experience to have to go, here for some of the coaching sessions and then if you can also search them in the dashboard.

Jason: Yeah, and also, the coaching hub was great when there were twelve coaching sessions in it. But now that we’ve done 41 and you have, what, four Januarys in there, it’s almost visually difficult to find out, like, where am I? I don’t even know what I’m looking for.

Caroline: So the last thing I’ll say about the dashboard that I’m really excited about is we took every single resource.

Jason: Which you counted, not including coaching sessions. Including coaching sessions.

Caroline: It’s like 75.

Jason: I think 90 something, you said.

Caroline: 97. Oh, I think we said 75, like, really solid. And then some of them are like old workshops and stuff.

Jason: Only two crappy ones, which I think everyone can relate if you’ve been doing something for five years.

Caroline: For five years.

Jason: The five years ago stuff you’re like, I don’t know.

Caroline: Yeah. But we took every single resource and we categorized it and tagged it based on what does it help you do? And then we organize those tags in sort of the unboring business roadmap framework, which is what we teach inside of WAIM Unlimited. It’s like a five step way to kind of diagnose, where do you need to put attention in your business? And so my favorite thing is in the library now. It’s like, okay, I need to work on building my audience and getting my content. And so then under that, you have like, getting your email newsletter started, you have setting up your marketing bridge.

Jason: Very specific resources we created.

Caroline: It’s like just specifically instagram.

Jason: Yeah, the thing that I love is that it’s based on the problem someone has not needing to know, oh, they did a coaching session on email and I have to go find that.

Caroline: Exactly.

Jason: No, I just need help growing my email list. Give me the resources you all created.

Caroline: It’s like, do you need help with sales? Do you need help with mindset? And so that’s my favorite part about it.

Jason: Yeah, the real sad part about the dashboard is you’re going to work on it for like a month amongst all the other things, and then we still have at least a month of development time, right. So that will not cost us $30,000 this time around because we just don’t have that money to spend on this. But we do have, I think, a better developer this time around who’s better at communicating at what his limitations are.

Caroline: Yeah, we got price gouged last time, just to be honest.

Jason: So, yeah, that’s the dashboard, and we’re excited for our WAIMers to get that. We’re really actually hoping that it might be done right at the end of our enrollment period. That’s very wishful thinking for the Spring, but we’ll see.

Caroline: So another thing that we’re working on is usually, again, we’ve been thinking a lot lately about WAIM Unlimited can solve so many different problems for so many different types of business owners, but lately we’ve been trying to narrow that down a little bit into solving a specific problem. And so what we’re focusing on right now is if you are a freelancer, if you are someone who already has established a business and you have clients, but you’re feeling very hamstrung by the lack of flexibility.

Jason: Trading time for money.

Caroline: Trading time for money. Kind of hitting that income ceiling, having to manage different personalities of clients, that can be very exhausting from a mental health perspective. So if you’re craving more flexibility and freedom, our story is that digital products gave us that flexibility and freedom. And so it doesn’t mean you don’t have to stop working with clients. It just means that if you had online courses or digital products or some other way to make revenue, you could only take on the clients that you really want to work with. So right now we’re focusing WAIM on attracting those freelancers, and part of that is building a new Notion dashboard, which we will offer with our Spring enrollment, and we’re calling that the Client Off-Ramp OS. And so it’s an entire system that’s specifically tailored for freelancers trying to shift to digital products. So it’s a dashboard that will help you better keep track of your clients, make your process more efficient, so that then you can carve out the time, start building an audience. And it has all of those content calendar pieces to it and it’s again, specifically tailored for a clear roadmap for people who want to make that transition.

Jason: Yeah. And I think what’s been really helpful for us is in having hundreds and hundreds of people join Wandering Aimfully over the past five years, we’ve really learned that we attract to Wandering Aimfully these exact people. So freelancers who are looking to move to digital products. And we knew that in the beginning because that’s really who we targeted with our Build Without Burnout program that we created. But we’ve never really kind of come back to that and said, okay, you all are still coming here, but we don’t have any new, newer resources to help with that. So this is the new resource that we’re going to build that will help with that. And especially, I think Notion has been a game changer to create things, to help people do things.

Caroline: Right. Because we’re always talking about like, information is only one piece of the puzzle. We love teaching, I love coming up with curriculums to teach concepts to people, but there’s a gap between information and action. And Notion for me helps bridge that gap. Because a checklist is one thing, but if you have it in front of you and you go, oh, here’s how I actually plot these on my calendar, here’s how I bring all this information to the surface. Like, to me that helps you act on it. And that’s a game changer. It has been for us, and so I want that for other people. And then also the second thing I want to mention here is just that if you’re like us and you have more of a general audience, like we’re talking to all online business owners, maybe experiment with not… You don’t have to niche down your entire business. You can just niche down your messaging for a launch to try to speak to a specific segment of your audience. Right. I think that’s a way that we’re trying to navigate right now because I love the diversity of different types of business owners in WAIM, but it also makes messaging kind of difficult because you’re trying to solve everyone’s different problems.

Jason: Yeah. And it makes problem solving difficult.

Caroline: Exactly.

Jason: Yeah. Okay, so that’s the Client Off-Ramp OS. And if you’re not a Notion user, we also have a Notion Starter Pack that we created that Caroline basically… like this entire system for getting started with Notion that’s included as well. So that’s a fun thing that we already have. So that’ll be done by the time like our enrollment is finishing for this Spring. And the next step that we are going to start working on but have not started working on is Narticles. So we talked about this in our 2023 preview episode. This is new articles. And the whole idea here is that we have, I think at this point, 130 published articles on the Wandering Aimfully website. There is no rhyme or reason to them. There is no series to go through where it walks you through solving a problem. It’s just like a bunch of haphazard thoughts that we had.

Caroline: Yeah.

Jason: That are helpful, but they’re kind of all over the place.

Caroline: Yes. Again, you’re going to have this if you’ve been blogging for seven years at this point, and that’s a lot of our content is and we have really high quality guides and things in there, but it’s so hard to find them. And again, you learn this after you’ve been in business for a number of years, of going, okay, here’s why I really want to help. Here’s what they really struggle with. So we know that we want to improve that. And as Jason said, we talked about this in our 2023 Goals episode, but the idea is to really hone in on what are those like eight to ten high quality articles that we can write? And then the missing piece, to me, I think, is going to be, how do we amplify those?

Jason: Yeah, I think it’s amplification, but I think it’s also just in, like, the display of those. So, like, you come to and it’s like if you go to the articles page, it’s like, here are ten articles to help help you go from point A to point B.

Caroline: Definitely.

Jason: You want to create more time with your client, your freelancer business. This is that article for you. And then it takes you all the way to the last one, which is like, now you’re running a digital product business. How do you manage that?

Caroline: Yeah, also the not competitive part of me, but the experimenter part of me is also just curious, like, I want to show or I want to find out, like, that an article strategy can still be incredibly beneficial to your business in 2023.

Jason: Without being on social.

Caroline: Yeah, because…

Jason: I think that’s the other thing.

Caroline: Yeah. Because and I think I think it’s it’s not just about traffic, which I think that will happen, but it’s also about, like, when people come to your site finding information that they’re looking for and going, wow, this person does have a lot of helpful content for me.

Jason: And I think that’s really the big AHA thing for us. And maybe this is something you can take away as you’re listening to this. Put yourself in the shoes of your ideal audience member. So, like, for us, a freelancer who’s looking to move to digital products, come to the Wandering Aimfully website. Is there any way that we’re helping that person? Not at all.

Caroline: There is, but it’s like you have to dive so deep.

Jason: Exactly. It should be front and center. So for you listening to this, maybe do that same exercise where you go, okay, my ideal customer is this. They land on my website. Can they immediately find some resources that help them with their problems? And that doesn’t mean go to your blog and search. That doesn’t mean like, dig seven pages into your website. It means, like, on your homepage in your navigation, like, how is that person getting some problems solved?

Caroline: Exactly.

Jason: So we’ll be working on the Narticles project probably for the next two months, I would imagine. And then you mentioned amplification.

Caroline: Yeah. And actually next two months is like we probably won’t even be able to get started until April.

Jason: Yeah. And then amplification. We’ll be experimenting with Pinterest, we think.

Caroline: Yeah, I think we’re going to try Pinterest. And I think we…

Jason: It’s this newfangled app that’s just getting some traction.

Caroline: Yeah. As you know, listen, when you’re short on time and resources, you have to intentionally deprioritize things. And so, yeah, we’ve never experimented with it. We’re excited to get into it. Also, I think coming circling back on our YouTube strategy and trying to get more mileage out of our articles by turning them into videos. Because I do think video is, as we all know, a very important piece of marketing in this current landscape. But we’re always trying to figure out, can we do video without being on social media? And to me, YouTube is not the same as being on Instagram or TikTok.

Jason: Yeah, can we do video and it not be a complete slog? Because I think video is one of the hardest things that we work on together. And so we have to figure that out. Okay, so that’s Narticles. Next up is a much shorter project that is going to be done by the time you’re listening to this, which we’re excited about, which is the new Wandering Aimfully homepage.

Caroline: Yes. So if you were listening to episodes a couple of weeks ago, we mentioned to you we did this Behind the Build Live experiment. And it was the first time doing anything like this, but we just had this idea of we wanted to create a new homepage and a new lead magnet that was more towards this audience segment that we’re talking about, freelancers transitioning to digital products. And so we just thought, let’s try to complete this in one day and have people watch us and watch our process. And it was a really fun experiment. We didn’t complete all of our tasks in the day that we allotted, but we got probably 85%, 90% there. And what’s great about it is that now we basically took everything that we did in that day and worked on a new homepage design that we’re really excited about.

Jason: Yeah. And what I love about this, so if you’re curious, since the inception of Wandering Aimfully, we’ve had five home pages, different home pages. I actually thought it was more.

Caroline: It’s got to be more.

Jason: One or two stragglers in there that got deleted. But really, that’s been it. And the one that we’ve had now has been up for three years. And it’s very simple and you won’t see it if you go to Wandering Aimfully now, but if you had not been there, it’s literally just like one sentence, three bullet points, a photo of us and then an embedded quiz. That was our home page.

Caroline: And I think the important thing to note here is when we moved to that extremely simple design, it converted better than the one before it.

Jason: And that was our goal, our email conversion.

Caroline: To boost our email conversion with the quiz. We did that because we just made the call to action so simple. But now we’re at this place where the efficacy has gone down over time. I think that happens with time because people who inevitably come back, it’s not new anymore. I do think there is something to not changing your home page every year, but adding some new freshness to it.

Jason: Yeah. I also think that the data tells us that 80% of our traffic is brand new traffic. So I think in three years… well, no, I think in three years, more people have seen more quizzes on websites. So the novelty has worn off of like, oh, what’s this business quiz? I’ll take this. It’s like everyone has a business. Not everyone, but like, a lot of people do. So with new users constantly coming, those people have seen quizzes elsewhere. So now let’s do a new thing that feels kind of like unique to us in a way that’s a little bit more in depth. So with that, we have the new design, which I love that you’ve been working on, which is very fun.

Caroline: Thanks. I like it too.

Jason: I think it kind of blends this app design that we have really been into a ton lately with a fun and friendliness of a coaching program that’s unboring.

Caroline: Yeah, we’re trying to from like a branding perspective because I always go back to like, what emotionally, are we trying to communicate with our branding and with our design? And we very much try to ride this line between friendly, approachable, fun because I think that is who we are, and also serious, strategic, bold.

Jason: We’re going to help you with business.

Caroline: Exactly. And so it’s like, how do you kind of find that line? And so that’s what I’ve tried to do.

Jason: You know how you do it? Use Impact font because it makes an impact. Yeah. So if you want to check out the new homepage, that should be up and live with our new lead magnet, free coaching session. Just if you’re interested, check that out. The next thing I wanted to talk about is something very leaning into the fun. This is a members-only, Wandering Aimfully members only accountability game that we created. So just to give a quick bit of context for this.

Caroline: I think this is really fun because I think it also shows people you do not have to do things the way that they have always been done.

Jason: Exactly. So the way that things have always been done is for the past three years, I have offered up space in my Slack direct messages to do one on one accountability with our members, where they could send me messages every Monday, and it was just called Momentum mondays. And they would send me messages, they would check in, we would talk about what they’re working on. And I did this for…

Caroline: Extremely high touch.

Jason: Yeah. Hundreds of our Wandering Aimfully members. Some people would do it for a couple of weeks, some people did it for the entire three years. It was incredible. But it was also extremely draining on me. And it was basically right after enrollments, we would get a surge of people who would want to do it, and I would be sending basically two full work days just answering direct messages.

Caroline: Two full work days a week.

Jason: A week, yeah. So there was a lot of work.

Caroline: Which is incredible because it’s like, yeah, you definitely want to offer… it’s like, we’re a coaching program, so obviously we want to coach people. But this is also where you have to balance how your offer serves people with what is it taking from you personally and how sustainable is that. And Jace just reached a point where I think you were just like, I can’t give two full days of my week every week, not only time wise, but also emotionally wise, because we make fun of you for being an emotional robot. But it’s a lot to be sort of like holding space for people.

Jason: Because these check ins weren’t just people sending me bullet points. Like, it was like sharing what’s going on. And I think the other big shift here that I wanted to make was these were all very personal one on one things. And we have a group coaching program and what’s the way that we could bring the group together to be in more of like, hey, we’re working on stuff together. We can see other people are doing things and get inspired. So we came up with this silly idea and it started in the beginning of February, and it’s a monthly game and it’s called WAIM of Stones.

Caroline: It’s like Game of Thrones, but it’s WAIM of Stones.

Jason: So the idea is we have a Slack channel. And in that Slack channel, it’s accountability at the beginning of the month. And we do… it’s basically one post every Monday of the month. So at the beginning of the month, you just have to reply with what your goal is for the month. And it’s completely custom to you as the person. And then each week I post a new post and you have to check in within 24 hours of me posting, because the part of this that matters is being accountable. You can’t just, oh, I’ll just check in on Thursday. It’s like, yeah, you’re not going to get it done because I’ve watched this happen directly with people.

Caroline: Yeah. There has to be a little bit of a discipline to it.

Jason: Exactly.

Caroline: In order for that accountability to really move you forward. And it’s really fun seeing everyone reply in that thread and say and so you’re basically just saying what were three things that you did towards your goal.

Jason: Yeah, as you move on throughout the weeks. What’s really fun is, as of recording this, we just finished the first month.

Caroline: Wait, let me say an important part of it is because we didn’t say it, the WAIM of Stone’s part is that there’s a game board that has four spots. And if you check in every week that you check in, you move forward one spot on the game board. It’s like Candyland. Right.

Jason: Or Jumanji without all the scary stuff.

Caroline: Yes, we created game boards. And the thing is, if you check in all four weeks, you make it out of the game board into the final spot on the board, where you attain a WAIM-finity Stone.

Jason: A WAIM-finity Stone. Please don’t sue us, Marvel. We’ve made up eight of these, and they’re just different character based things.

Caroline: So February was the Apprentice Stone.

Jason: They’ll be the Knight Stone. They’ll be the Squire Stone. And we have, like, little silly illustrations that Caroline came up with that have our faces on them. It’s just ridiculous. But here’s the really fun part. I expected when we started this at the beginning of the month, just to give context, our Slack Channel has 1000 total people in it, but at any given time, it’s like 100 to 150 people are active. That’s very normal for a community, a Slack Channel like this.

Caroline: That’s been open for…

Jason: Many years.

Caroline: Six, seven years.

Jason: Yeah. I expected, personally, like, 30 people would join the channel, and then I didn’t know how many people would then do it. So maybe like ten.

Caroline: Right.

Jason: 99 WAIMers showed up for this thing. It’s the most active thing we’ve ever had in our Slack Channel. It’s the most consistently active thing we’ve had week over week. So we just finished this month, and in the last thread, we had 91 comments, people posting and wanting to get credit for this.

Caroline: By the way, the thing I love about it, too, is that you can make it to spot four and get your WAIM-finity Stone. It doesn’t matter if you achieved the goal. What’s important is that you showed up every week. Because that’s the part that is important to us, is not about whether you succeed. It’s like, what did you learn along the way? Did you show up? Did you just keep showing up? Because that’s so much of what success in business is about.

Jason: What I love and I don’t have well, actually, I do. Let me just real quick, I just want to pop in and read some of the comments. I’m not going to say any names and I’m not going to call anybody out, but I just want to share some of the phrases and things that people have said because I think it’s so fun just to say.

Caroline: While you look that up, I just want to say I think this is yet again, just an example of you don’t always have to do the boring thing. Right? It’s like, okay, it did start out as quite a boring idea, which was, okay, it’s not sustainable for you to do this anymore, so let’s just create a Slack channel and let’s have a monthly group accountability program. And then we just said, what if? You’ve heard us talk about this phrase before, but just when you put what if in front of a question, we were just like, what if it’s fun? Like, what if it’s not the normal thing? What would that look like? I know exactly what the inspiration was. We were both playing that language game.

Jason: Oh, yeah, Lingo Legend.

Caroline: It was called like Lingo Legend or something and it was just like so just a world of… oh, and also maybe you were into Zelda at the time.

Jason: I think I just started playing Breath of The Wild again. Yeah.

Caroline: It’s a lot of these things and we just were like, what if it’s that? Like, what if it’s an adventure?

Jason: All right, so let me read just a couple of these real quick. And again, not names. I can’t say anything, but… I’m so happy. This kept me accountable and I completed my goal, even with a bit of bonus work this month, which is just wonderful. I didn’t hit my goal, but I learned better how to prioritize things in my business. Bonus that even shifting my priorities felt good this month.

Caroline: Love to hear that.

Jason: I love that so much. I didn’t hit my goal, but I’m still really happy with the progress that I made this month. I love that because I think so often if you don’t hit your goal, you might feel like any progress you made isn’t helpful.

Caroline: Like the homepage thing from Behind the Build, it’s like just because we didn’t hit the goal, which was to have both of those things done by the end of the day, wasn’t the point. We look back and I’m like, man, we got so much done that we wouldn’t have gotten done otherwise.

Jason: Yeah. I was all over the place this month, but I did find focus and I worked on one small bit ahead of this week that I wouldn’t have worked on before, which is fantastic. Focused on all of my client work, got it done ahead of time for the first time this month. And then I’m not going to read too many. Literally, I have to scroll so much to get through these. But I love there was one final message that I really appreciated because I felt the exact same way. Again, I have to scroll through like 90 some on things here. Someone said, is it weird to feel this immense collective pride at how much everyone has achieved this month? Even if you didn’t reach your goal, you still made progress and it felt so good to do it, like, together.

Caroline: Yeah.

Jason: And I think that like that to me is as we were doing this game every single week and as we were kind of tracking along, I could read that in so many of these comments is so many people were saying things like, I normally would give up if I didn’t show up, but I wanted to come back to this channel and be with everybody else. And so huge check for us on this game, being silly, being just something very different, but it really working.

Caroline: And also we had no idea if people would do it, but we also were coming at it from a place of what would we want to keep up with every month? And so whatever I think the lessons for this, for the person listening, are like, what could you do differently in your business? It doesn’t have to be boring. And also what’s going to make it fun for you to engage with it so that you’ll stick with it too?

Jason: Cool. So that’s our WAIM of Stones accountability game. And again, it’s it’s not to put any pressure on people to have to get things done. That’s not what we’re trying to do. It’s just to try and make little bits of progress every week on whatever it is is important to you. Cool. So two more things here with WAIM and then we’ll move on to Teachery. Number two on this last two is our monthly coaching sessions. We do this every single month and we try and blend unboring with teaching and practicality and learning stuff and you do an amazing job of the curriculums. But one thing I wanted to share, I’ve said this on previous episodes, but I just love bringing it up. We are now at 41 total coaching sessions. When you think about that, seven more months of doing monthly coaching, we will have done it for four years straight.

Caroline: That’s wild.

Jason: That seems so weird. It does not feel like something we’ve done every month for four years that’s 3 hours of valuable content.

Caroline: No. And what’s so interesting is like, I don’t know, maybe if you had told me in the beginning you’re going to do this every month for four years, maybe I wouldn’t have done it because it would have felt so overwhelming. And so…

Jason: I don’t want to be tied down.

Caroline: I want to be tied down. But the truth is, first of all, I think a couple of things. Number one, we didn’t back ourselves into a corner because it started as a six month program and we just said, we’re going to try this. And then that was really a pivotal point in Wandering Aimfully where we positioned to a coaching program. And then people were like, oh, this is really valuable because I get something to focus on every month. And then we were like, well, not only do people really love it, I think that’s, like, to use the app world or the tech world, that’s where we found product market fit, it feels like. And then what happened was I realized, oh, I actually really love this. And I think that going back to what we just said about WAIM of Stones, what helped me love it is that we did it in a way that worked for us. So instead of being like, oh, okay, I have to do this like a webinar where I do… it’s like, we always had this story time element where I thought of a fun metaphor and I got to add these design elements.

Jason: These like, six and eight dollar Creative Market illustration packs.

Caroline: Right. We’re talking about content strategy, but our content strategy is a content salad. And so here’s what that means. Or I was just thinking about memberships we did, and it was like comparing it to a gym membership and what are the elements? And just having these metaphors that were really helpful. Your website wizard like…

Jason: The marketing bridges.

Caroline: And so by encouraging us to do it in a way that felt unique to us, it hasn’t felt like four years of work, because I really enjoy it.

Jason: Yeah, and I think what’s been really helpful, too, is the amount of time that we’re investing in the coaching session has ebbed and flowed where, from the beginning, obviously, we were pouring more time into every month’s session. And it was probably taking you 20 to 30 hours to build a session and a workbook and then to deliver it in a three hour session.

Caroline: But here’s what I learned about that too, because this year we have been doing these what we call Spotlight Sessions, and they’re a little bit shorter, a little bit more concise.

Jason: Like a little bit shorter.

Caroline: But what I learned is that oftentimes, I think, as a business owner, you stuff your offer full of all this stuff because you want it to be valuable. But what you don’t realize is that what’s really valuable is saving people time. And so it got to this place where I was like, oh, it’s actually not as valuable if someone has to sit through 3 hours to get value out of it. We need to break it down in a way where they can get something in 45 minutes. And so that’s just a revelation, I think, that people need to hear it’s not always the time investment or the amount of stuff in a product. It’s like, how quickly can you deliver value in terms of them receiving a result or an outcome?

Jason: Yeah, I’m really excited. So one thing that we’re going to add here very shortly that is actually already created, but we haven’t announced it or shared it yet. This is the first time we’re actually sharing it publicly, which is cool, is we’re going to do a private podcast feed of just the audio versions of our coaching sessions.

Caroline: Right. Which we’ve always had the audio files for accessibility.

Jason: But like who downloads an mp3?

Caroline: Well, people.

Jason: No, I’m just saying but this is a much better experience to be able to do that.

Caroline: Yes, because where are you going to play that?

Jason: Exactly. Yeah, I’ve tried to download an mp3 on my iPhone and been like, where does this go? Where do the files go?

Caroline: It does, it goes in your files, but then it’s not a player. So if you go off of that screen, you can’t come back.

Jason: Exactly. So anyway, I think a fun example too of like, we have evolved to our coaching sessions had audio mp3s that you could actually download and listen to and take with you and find them in the files of your phones. But now we’ll have this private podcast feed that I’m very excited that someone can just subscribe to and any podcast app will have this QR code and these links that’s set up and it should be really easy for you to just plug in and listen. And so if you’re someone who likes to show up and you want to be there and you don’t want to take a ton of notes, you just like the energy, and then you want to listen maybe two days after that to assimilate more of the info that we talked about, you can just plug in your podcast player.

Caroline: If you’re someone at the beginning of your journey of building your program or building your content, it’s like, sure, you don’t have to worry about that, right? It took us four years to add that option. But if you’re someone who is looking for more ways to have your content go further to make it more accessible, I think that’s a really smart way to do it. We’ll see how much people engage with it, but we’re just excited to always be thinking about and adding different ways for people to engage with our resources.

Jason: And this was a good one. It wasn’t a lot of time investment. This is where we had a freelancer who helped us set it up. And I think it took them under ten total hours to take all of our previous audios that had already been added to coaching sessions, put them in the feed, change the name, change the descriptions, and the app that we’re using, Hello Audio, made it super simple to create the feed and then just hit publish. So really like, not a ton of time investment to set up and move forward, which I really liked about it. A lot of these things on this list are time intensive, so I think it’s helpful to say like, say this one took a week.

Caroline: For sure.

Jason: And then just to finish off here with WAIM, not Wayne, is our ongoing content that we’re working on so we have our weekly newsletter, which we have been doing series, and we have all of the series planned out for this year. So those are like four to eight week emails. So we’ll keep doing that. And then this podcast, which we will continue to do. I think we do have some semblance of a possible idea of another podcast we might want to do or maybe different episodes in this podcast. I don’t know. There’s something else with podcasting this year we might experiment with, but that’s later in the year.

Caroline: Later in the year.

Jason: And then YouTube.

Caroline: We already, lol…

Jason: Yeah.

Caroline: We already said that. I think coming back around to YouTube again later in the year will be a focus for us. These first two quarters of the year are all about kind of reinvesting in the foundation of WAIM. And the last thing I wanted to say is, I think I just realized a lot of the reason that we have the time to work on all of these things and to move the ball forward on so many different aspects of the foundation of our business is actually because we chose not to be on social media.

Jason: Absolutely.

Caroline: And I think it has freed up so much mental space, and I know that that’s not a reality necessarily for everyone, wherever they are on the journey of their business. It’s very rich for two people who have been building audiences for almost ten years to sit back and say, you don’t need social media, and someone who just gets started is like, okay, but I kinda do.

Jason: But I need some people to know that I exist.

Caroline: Yeah, exactly. So we’re not telling you that you don’t need it. It’s just if it’s something that is not, if you’re someone who struggles with the benefit, it brings your business, but the detriment it brings your mental health. I think we always go back to this notion of creating an off ramp for yourself. So it’s like use it for a year strategically to grow an email list, to grow another place where you have an audience. Right? And so I was looking at this list and I was like, man, are we more productive than we used to be? Are we this, are we that? And it’s really just like, no. A lot of that time was seeping out into this hamster wheel of Instagram creation.

Jason: I do think there is just a reality, too. If you are an honest person about your time and you look at your week and you go, oh, I spend 20 hours on social media a week, maybe it’s 10, maybe it’s 40, whatever it is for you. But let’s just say it’s 20. That’s 20 hours every week. You could put toward a new dashboard, new articles, a new product, an accountability game. It’s all of these things that you will now find the time for which can lead to other things. So I just say that as an example of sometimes folks think, oh, if I get off social media, everything’s going to fall apart. It’s like, no, you now gain 20 hours a week to work on other things to replace that.

Caroline: Right.

Jason: Okay, so that’s WAIM. That’s what we’re working on. And then obviously we’ll have more stuff in Q2 and Q3. So if you really like this episode and you want us to do this again, send us an email, And maybe we’ll make this a quarterly thing to check in on what we’re working on.

Caroline: Totally.

Jason: Now let’s talk about Teachery because we have this whole other business.

Caroline: Just a whole other dang business.

Jason: Yeah. And I think if we would have recorded this episode a year ago, we wouldn’t have had much to talk about because Teachery didn’t get much time or focus. But we’re really trying to invest more time and focus into it. So let’s share some of the things that we are working on, starting with our new trial flow.

Caroline: Right. So the idea is to grow our customers this year, and we did…

Jason: Do you want to share what that is? Just as a reminder from our… we said in the 2023 goals.

Caroline: What?

Jason: What our customer growth goals are.

Caroline: You say it.

Jason: It’s like 3x-ing our customers. So we have like 250 active customers. Yeah, we’d like to get to 750 active customers by the end of the year. And that’s like if everything went right, it’s probably not going to happen. But that’s our high goal.

Caroline: That’s our high goal. That’s the aggressive goal.

Jason: I think our low goal is just not to lose all the customers.

Caroline: But we started by doing what we would tell anybody to do, which is look at what’s working and see how you can optimize that first so that you can get leverage in order to pour into other things. So we kind of looked at where are the points in our quote unquote marketing bridge where we’re losing people right now and we realized that our trial sign up flow could be better. So we did a couple of little tweaks to that, being more clear about the fact that it’s no credit card required, which is pretty unique. Getting more clear about the fact that it’s 14 days, which is longer than most, and then simplifying those steps so that someone actually does complete the free trial sign up before we have this whole thing where you say what your lessons are going to be. And that was really optimizing for people to complete their course. But what we need at this stage is for people to just get inside Teachery and start playing around.

Jason: Yeah.

Caroline: So we simplified that a lot.

Jason: Yeah. And I think one big change from there that was helpful, which is it’s done it’s up. We have the new trial flow going. It took us about, I think, two weeks total. We had a little bit of a development hiccup that we ran into but before we would have people go through the trial flow, they would kind of, quote unquote, create their first course through that. But it was very basic and didn’t have much in it. And I think if we just went back and looked at a cursory glance, almost everybody started a course that just said, like asfdasfdasfd, because they were just like pressing keys to get through it.

Caroline: Gobbledy gook.

Jason: Because they didn’t know what they wanted their course to necessarily be at that moment.

Caroline: Yeah, exactly. And they’re like, I just want to get…

Jason: I want to get in and see this thing.

Caroline: I want to get into the thing. I want to play with the thing.

Jason: So noww we kind of just do this thing where we spin up a course for them, just called Your First Course. And it just is a very meta example of here’s a lesson that you would teach this in, but also here’s some tips about using Teachery. So it’s a much better experience. I think it’s fun that we’re giving people very helpful actionable things right away to get into as opposed to dropping them in and being like, well, now what do I do? I don’t know what I’m looking at. So that’s going on. And then along with that, what you bring a lot to this is like, let’s look into some analytics and data and let’s see some things we need to track. And in doing that, we found out there’s not real reliable information that we’re getting from any of the sources that we’re tracking. And it’s also not the super helpful information that we want to know if our business is growing.

Caroline: Yeah, this is where metrics just really come in handy, especially in a software business. You need to know how many people are coming to that sign up page and how many of those people are then signing up. Right. How many people are dropping off? These are the things. And for me, you can very easily kind of go way too deep into that stuff. And so it takes a little bit of discipline to go, we have very low time resources right now. Let’s not go absolutely nuts on tracking all the things, all the events, all the signals. Let’s just identify the handful that are going to help us move forward at this stage. We actually just had our developer spin up an internal admin dashboard for our analytics, rather than going to these third party resources, just taking the most true data, which is our data.

Jason: Which I think is really helpful if you run your own business and you hate logging into Google Analytics like the majority of us do. I know that things like Fathom, my buddy Paul Jarvis started, which is like a much better experience, but it’s not the data that we necessarily need. We need the trial conversion data. And I know you can set up events and do things, but that stuff really just like it boggles my mind and it tends to be more cumbersome.

Caroline: Yeah. And down the road, maybe when we have a marketing person in house, that would be something that they could set up, but it’s not a good use of our time and attention to try to learn that right now.

Jason: And also, the one thing that I really like, because this is one thing that our developer was telling me when he was building this simple dashboard, was even like, Fathom’s data is skewed because it’s not necessarily 100% true. Like, they’re filtering out some things and whatnot. So this is helping us get the absolute true data from our database, which I think is helpful. So that was something that we did and that’s up and running.

Caroline: These things are just so investing in the foundation, and maybe we’ll do an entire episode on this idea. But it’s like when you’re working on things in your business where you’re in like a season of planting seeds, sometimes it can be so frustrating because you’re like, nothing I’m doing right now is bringing me any type of gratification, like instant gratification, which things like Instagram do, right? You go, oh, I can see my numbers growing and I can see some con–. It’s like everything we’re working on right now will not pay off for like months and months, which is hard. But also we’ve been doing this long enough to know that that is how it goes. You have to plant seeds if you want to see that growth in the future.

Jason: Have you logged into the dashboard yet, the little analytics dashboard yet? Every day I’ve logged in just to watch the numbers grow. And it’s just fun because it’s our little dashboard we’ve created and it’s just fun. All right, let’s talk about some features that are coming to Teachery, because this is really where the rubber hits the road with this little application for helping people build online courses. So the first feature that is almost done and will probably be out in the next coming weeks is course admins. So this is allowing someone else, a freelancer or a VA or anybody else to log into your Teachery account and tweak your courses, your customers, take actions within your course. This has been a long time coming. A lot of people have asked this feature, and it’s one that we have just been putting off because it’s very complex on managing the role of the person. So I think the design for this took like a day and the development has taken three months. And granted, our developers juggle multiple projects. But even now, yesterday, our developer that’s working on this was telling me, he was like, oh, I found this weird edge case where if a course creator has a custom domain and the admin logs in not from the custom domain, they’ll be blocked from using it. And I’m like, we never would have discovered that. That would have been something people ran into and it was just a nightmare. So there’s like a lot of things going into this, but that feature is coming which I’m excited about because it’ll just help people manage their account better. And then the next feature people are really excited about because we actually sent an email out with a teaser that you put together is course hubs. Do you want to talk about course hubs?

Caroline: Yes. So course hubs is basically a way for you to showcase and organize groups of your courses. So if you’re someone who has first of all, you want a page to send people to almost like a shopping cart for all of your courses, this is a way for you to do that. But you can also have the flexibility to organize them. So if I’m someone who I have design courses, but I also have hand lettering courses, I can separate those courses because they’re all in Teachery and I can have sections of those. And so not only can I send someone to all of my courses where they can individually buy them, but they could just buy all of them too.

Jason: Yeah, that was kind of like a last minute decision, was like, what if we just put a buy all button on here for that’s optional for people to turn on?

Caroline: Because then you can also create these robust bundles, right? Of all your courses. Like you can just have a one set price for all your courses.

Jason: So yeah, we got some really good feedback. And also I think the thing about course hubs, it kind of pulls from Teachery’s customizable course design where it just looks better and you can add your own design flair to it. You can add your own custom CSS to make it look however you want and it’s just very easy just to click and add courses or remove them. So I think course hubs is going to be great just in the feedback that we got from people when we sent the teaser out. But that one will probably be done in the next next month as well.

Caroline: Great.

Jason: And then one that we just got the designs back on that hasn’t been started yet. Go ahead.

Caroline: We finally separated our courses page because for the longest time on your main courses dashboard page, inside of Teachery, you would not only see courses that you’re creating as a teacher, so to speak, but if you had purchased any other peo–, of other people’s Teachery courses, you would see your purchased courses in the same place and we just felt…

Jason: Not exactly the same place on the page, but on the same page.

Caroline: And we just felt like it got very cluttered very quickly. And so we finally have reorganized that. So you have all of your courses of the things that you’re creating and then that’s under your teach section and then you have a learn section where you can see all of your purchased courses. So that when you’re in learn mode and you’re learning from other people, you’re not being distracted by courses that you have that are half done.

Jason: Yeah, and shout out to our designer, freelance designer, Maddy, who has been working on this.

Caroline: She’s done a fantastic job.

Jason: She’s done a fantastic job. And also I love that in the learn section, so this is for customers who have bought courses from people. Now it’s a little bit less Teachery branded and kind of just simpler to see your purchased courses because Teachery matters in the grand scheme, but not to someone who just wants to access courses they’ve purchased. And I love that she made that simpler, but then also added like a light mode, dark mode, which is kind of fun. So you can toggle back and forth that, which is just a nice little touch. So that one’s probably going to be like a month or two away because we have a couple of other things in the works. But next up is another one that’s been on the list that people have been asking for and I’m just really hoping we get this one done by the end of the year because it’s when people ask for it is gifting a course. So this is just simply allowing on a payment page a toggle that someone can buy this on behalf of someone else. You would think this would just be such a simple addition. It is not, because there are so many things behind the scenes in the app.

Caroline: It’s the complexity of separating the purchasing data from the user data which is difficult.

Jason: Because if Caroline wants to create a payment page that someone can buy as a gift, let’s say her friend Sharon is buying the course on behalf of her family member. Sharon should not get access to anything and she doesn’t need an account in Teachery, she just has to be the purchaser. This breaks our entire system. So this is why we put this feature off for such a long time. But we’re hoping by the end of this year it will be ready, it will be available and that will be done. And then one that we’re hoping to work on sometime soonish.

Caroline: This is the big one.

Jason: I don’t know when it’s going to get done.

Caroline: It’s a very big one because the reason I’m the most excited about this one is because this to me is an example of product led growth, which is prioritizing features that also have a marketing opportunity built into them. And so this is our theme showcase. And so we worked at the end of last year, one major feature that we worked on was just the ability to create themes, meaning basically custom design settings of a course. And then you can also sell a theme. So if I create a Teachery course and I have all the styles and I make it look custom and beautiful, I can sell that as a theme and somebody could buy that and then just spin up a Teachery course with all of those styles and colors and all of that. What we now can do because we have that feature is we can create themes that we have made. So imagine I designed ten different themes. These are the basic infrastructure of a Teachery course, but different colors and different kind of design vibes.

Jason: And what I like is that we can really focus on a couple of different archetypes with the themes.

Caroline: Exactly.

Jason: It could be like a course for yoga instructors, a course for photographers, and so that as a customer who might use Teachery, you go, oh, there’s a photography theme that I can just immediately grab and spin up my course and change a couple of colors and my logo and I have a course design done for me. That’s a huge win for that person.

Caroline: Exactly. So that’s really going to be huge. We want a place where we can really showcase those different themes that people can start right away with themes so you’re not just starting from scratch. You basically have pre designed themes. And then we also think that that is going to help with converting people to free trials as well because if we feature that on the homepage and just the ease of being able to start with a theme, I think that will encourage people to get into Teachery, play around with it for the first two weeks, and really play up that unique differentiator that I think Teachery brings to the online course creation space, which is just extreme levels of customization and making your course look branded the way that you want, which is not always something that is easily available in the other course creators.

Jason: Yeah, and I think really it’s taking a page out of Squarespace’s book from when they had all the templates that people could say, oh, I want to just spin up a website, I want it to look similar to this. I can one click, get this template and start working on templates. These things, themes are no new thing in this space but for us it’s a new thing and we already have enough traffic coming to Teachery, we think. And so it’s really just about trying to get that traffic to see the value to become a trial member and theme showcase is going to be a way to do that. So that will also lead into a whole new homepage of Teachery that’s going to be much more simplified, focusing on the theme, getting started and doing that. And then the last thing just to touch on is ongoing content for Teachery. Right now we do absolutely nothing. So any more of it will be an improvement but we don’t know exactly what that is yet. The first thing we’re going to do is basically just do a big cleanup of our email system and the automation and then look at like do we start sending like a monthly update consistently with what we’re working on? Because as you can hear, we’re working on plenty of stuff and we want people to know about those things, so that might be a good place to start and then we’ll think about if we want to do any external content, but way later in the year. How do you feel? Got a lot of stuff going on.

Caroline: That is a lot of stuff.

Jason: Yeah, and just as a reminder, like, we’re not doing it all this week.

Caroline: Yeah, no, we’re not doing it all at the same time. It’s just at any given moment, these are all different kind of things that we’re moving forward. And I think we’re able to do all of this because we’re many, many years into this now. And I think in the beginning, it’s really important to focus and be extremely narrow in the things that you’re trying to achieve. And I think the more that you have some of these plates spinning already, you could just optimize. A lot of this stuff is actually just optimization. It’s quite a bit of like, none of these things are really… I’m just trying to think. Nothing is just like starting from scratch actually.

Jason: For Teachery or like…?

Caroline: No, actually, if you go back through all of these things, every single one of these things is something that already exists. It’s an optimization of something that already exists. So I think that’s an important point as well. It’s just we’re in that season of reinvesting, refreshing, optimizing.

Jason: Yeah. All right, cool. Well, we hope this episode was…

Caroline: Interesting, at the very least.

Jason: And what I was really hoping, too, was as of recording this, I listened to an episode like this from another podcast and I go, oh, that’s an idea of a thing I want to do in my business. I just took one thing from that that now I’m energized and motivated and I want to go work on.

Caroline: Exactly.

Jason: And we hope that you didn’t get overwhelmed listening to all the things we’re working on. And instead, it motivated you to go, oh, I want to redo my home page. Or I want to go build a new lead magnet, or I want to add a new feature. I want to try an accountability game that’s silly and weird, too. And whatever those things are for you. We hope this was helpful. So that’s it for us now we need to go work on these things.

Caroline: Yeah, but we’re going to take a walk first.

Jason: I think we need to just, like, do them all.

Caroline: Although walks are dangerous because lately when we go on walks, we have more ideas.

Jason: So it’s a silent walk.

Caroline: I think we need to institute silent walks.

Jason: It’s actually a Portuguese only walk, which means that I’ll say, like, numbers. I know you would love that, but…

Caroline: That’s a good idea.

Jason: Yeah, but we’re not doing that. I’m just letting you know. I’m not there yet.

Caroline: I think that’s a good idea.

Jason: I know, but I’m not there yet.

Caroline: Okay. Can we just do…?

Jason: Maybe.

Caroline: That’s a practice thing.

Jason: Okay, that’s it for us. Goodbye.

Caroline: Goodbye.

159 – All The Things We’re Working On Right Now

(Big Fat Takeaway)

Ever wonder what someone is working on in their business? Here's what we're working on with WAIM and Teachery in Q1 of 2023.


This article written by

Jason Zook

I'm all about that Cinnamon Roll life (that just seemed like a "cool" way to say I love baking and eating cinnamon rolls). Also, I co-run this WAIM thing as well as Teachery. Currently, 75ish% completion of Tears of the Kingdom 🧝‍♀️⚔️.

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