Wandering Aimfully: The Show

It's the night before our launch and I'm recording this from bed while Leon sleeps upstairs and Caroline finishes a few things with our SceneRoll sales page

Caroline's first solo unfiltered episode!

Unfiltered episode recorded on a Sunday walk while Leon naps:Haven't felt this excited about building since iWearYourShirt in 2009Claude Code (especially the Mac app) has been a game changer (way beyond what Lovable could do for us)Built an autonomous Teachery blog engine in ~2 hours: 3 articles/day, Telegram updates, auto-publishedAlso built a content digest that turns voice memos into tweets and newsletters that sound like meMade my first real commit to Teachery's codebase! WOW!The tension: endless ideas, not enough hours, still wanting to be a present dadPrediction: 2026 creative output will be 10-30x any previous year. Does it feel that way to you too?

Trying a new thing with our podcast! We're going to record and release unfiltered episodes.On my walk this morning I had some thoughts about Teachery I wanted to share:Where the business startedThe main 3 evolutions Teachery has hadThe big ah-ha moments in 2025 that reignited my passion for TeacheryThe next version of Teachery I'm stoked about (v4.0)The first BIG financial goal I've set for Teachery in a lonnnnnng time!Hope you enjoy and look for more of these episodes from each of us soon

After a few months away, we’re back behind the mic with a real-time life and business update. In this episode, we share what the first four months of parenthood have been like, how our parental leave actually played out, and where our work is headed next.We talk about:Life with baby Leon and what surprised us most in the early monthsHow stepping away from WAIM Unlimited and work impacted usWhat’s happening with Teachery and why it’s entering a new chapterTwo very different paths we’re considering for what we build next—and why we’re tornWhy clarity still comes from action, not overthinkingThis episode is part catch-up, part behind-the-scenes, and part open-ended invitation to follow along as we figure out what the next iteration of our work looks like in 2026.

In this episode, we’re answering a handful of questions about our pregnancy journey so far (36 weeks as of recording!) We talk about everything from favorite (and least favorite) parts, to how Jason’s been helping, to what’s surprised us most along the way.We also chatted about:How we’ve prepared financially for babyWhat it’s been like stepping back from WAIMSome of the more emotional, unexpected shifts we’ve experiencedPlus, a few questions about what work and childcare might look like and the baby’s future citizenship in Portugal.

We just wrapped our last-ever launch of WAIM Unlimited. All while 7 months pregnant, grieving the loss of two family members, troubleshooting a broken-down car, a 5-hour medical snafu, and somehow still exceeding our high goal for our launch. Let’s break it all down.In this episode, we’re going to cover:What actually worked (and didn’t) across email, Instagram, affiliates, YouTube, and moreA surprise takeaway about boosting IG ReelsThe total revenue, MRR, and where we spent moneyHonest reflections on marketing, momentum, and managing real life during a major launchIf you’re curious about what went into a “final launch” of a signature program, the tactics, the lessons, and everything we did to beat our high goal this one is for you.***

This is part three of our 3-part series sharing the real-time updates of our LAST-EVER launch of our un-boring coaching program WAIM Unlimited.As of recording this FINAL installment, we have just 12 hours left in the launch

Since we've been running WAIM, certain questions come up over and over. In this episode, we’re answering the top 10 things we hear most from creative business owners who feel stuck and don't know what to do next.We cover:How to increase sales without feeling pushyHow to get clarity on what you're building and who it's forHow to overcome fear and self-doubt…and 7 more honest, practical questions that we think every solopreneur asks themselves at some point!Whether you're considering WAIM Unlimited or just want some grounded guidance, this episode is packed with the real stuff.

♾️ WAIM Unlimited: Past, Present & Future opens for enrollment for the FINAL TIME on June 9, get early access and bonuses here: https://wanderingaimfully.com/waitlist**Are digital product launches dead? Not at all! But in 8 years, we’ve noticed a few changes and we wanted to share what we’ve seen firsthand. How many sales emails matter? Do you actually need launch bonuses? Is there value in using AI to write sales page copy or does it sound too… AI?Here’s what we cover in this ep:Why pre-marketing matters more than ever (and how to start sooner)The power of “carrots” and launch events to drive urgencyWhy inboxes are cluttered and what to do about itHow specificity and social proof are becoming non-negotiableWhy it's easier than ever to execute a launch (doesn’t mean sales are easy)Whether you’re prepping for a big product launch or rethinking how you sell altogether, this episode will help you show up with more intention, strategy, and confidence.***

⏳ We're just a short time away from the FINAL enrollment of our un-boring coaching program. Get on the VIP Waitlist here: https://wanderingaimfully.com/waitlist**We are many months away from 2026 and the big shift in our Wandering Aimfully business, but we wanted to pull back the curtain and share how we ideate business ideas BEFORE they see the light of day.This episode, we hope you get to hear how we brainstorm, how we go back and forth, and when we get excited (or not) about a potential new idea.In 2026, we’re going to shift from monthly coaching to building tools using AI no-code platforms (like Lovable). These are a handful of the ideas we might embark on. Let us know if one or two resonated with you!

If you’re like us and using GPT (or Claude, etc) on a daily basis, then you have an AI that is gaining context about you constantly. With that in mind, we decided to ask AI to come up with questions they thought would be compelling for us to answer!In this episode, we have two AI Speakers joining us to ask us questions about our businesses, content creation, and our lives. The AI voices were created using Descript and the questions were created via ChatGPT.We thought this was SUPER interesting and very fun to see what things stood out to the artificial intelligence we spend time interacting with daily.***

We’re one month into our return to Instagram after a 3-year break, and in this episode, we’re pulling back the curtain on what’s working, what’s not, and how we’re approaching Instagram in a way that actually feels good (and sustainable). Spoiler: we’re not here to growth-hack, we’re here to experiment, stay aligned with our business, and TRY to enjoy the content creation process.We cover:What our first month back looked like (formats, topics, opt-ins, and spaghetti-throwing)Surprising lessons from low-effort Reels and a spur of the moment carouselWhy we’re pivoting to a focused content series, 40 Days of Launch Prep, and how we’re using storytelling as strategyA behind-the-scenes update that we’re already a bit behind on our Month 2 plan, but we’re moving forward!How to reflect on your own content strategy and find what fits your seasonIf you’ve been thinking about returning to social or just want to create in a way that’s more creatively fulfilling, this one’s for you.

With just a few months to go before our Tiny Zook

This is the second part of our discussion about retiring our WAIM Unlimited coaching program. We are going to do ONE final enrollment period in a few months and we answer some of your questions about this decision.The questions we answered in this ep:How are we feeling confident when it comes to the money side of this decision? Do we have savings? Other skills we can fall back on? Are we freaking out about this at all?Monthly coaching has been so valuable for our customers, why would we stop doing it?We talk about running a “calm business” does this completely change how calm things will be for us?Why should someone buy WAIM Unlimited during this last chance to purchase? Hope you enjoy hearing us discuss more of the real-time decision-making and thought process to this big shift in our business! ***