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We’re Jason and Caroline Zook, a husband and wife team running two businesses together and trying to live out our version of a good life in the process. In this business podcast, we share with you our lessons learned about how to run a calm, sustainable business—one that is predictable, profitable AND peaceful. Join us every Thursday if you’re an online creator who wants to reach your goals without sacrificing your well-being in the process.
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Sleeping With The Boss

Jason Zook and Caroline Winegeart host Sleeping With The Boss, a relationship show about living together, working together, and loving together.

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Sleeping With The Boss is a weekly show about relationships, work life balance, and entrepreneurship. Hosted by a couple that live, work, and sleep together - Jason Zook and Caroline Winegeart.
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Here we go, folks! We’re back on the short-form video creation train and this week we’re sharing our plan of action for Teachery. We’ve been off social media for 2.5 years, so this is quite the journey! If you missed last week’s episode, we’re embarking on a 5-week content extravaganza 😂 for our two businesses. This week is the official first week …
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Bring on the 5-week content EXTRAVAGANZAAAA! We are getting back in the content creation saddle for the first time in almost 3 years. We’ve only been creating “nurture” content for the entirety of our WAIM business and that’s about to change! This week, we’re kicking off a big content creation project for both WAIM and Teachery. Now, Teachery is a …
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We LOVE a launch recap episode! And as two people who value transparency and honesty in the online business world, we hope you appreciate this one because our latest launch (Spring 2024) didn’t quite hit the mark. Now, we want to be 100% clear: We are not upset by a 6-figure launch. There is nothing to complain about or shed a tear about. However, …
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Join us this week as we celebrate episode #200 of this podcast by sharing a few untold (maybe just lesser known?) stories from our entrepreneurial pasts. We each picked a few stories for the other to share without telling them ahead of time — fun! In some ways it feels like we’ve recorded 200+ episodes of this podcast, but in other ways, it kind of…
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We’ve been working together in some capacity for almost 15 years! In that time, we’ve learned how to communicate, navigate each other’s emotions, but we still run into difficult moments like we did this week. In this episode, we want to share our experience as a couple who works together (on two businesses!) but also how you can apply some of our l…
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What do you do when you have a TON of ideas and all of them feel like they need your attention? How do you sort them, prioritize them, and schedule them? Thanks to listener Leah W. for submitting this week’s podcast topic! This is a timely one for us as of recording because we’re overflowing with ideas for our two businesses (Teachery and Wandering…
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We thought it would be fun to share the tools that we’re super excited to be using in 2024! Most of these are used for biz purposes, but a few them overlap with life too. If you’re a fan of the video game MarioKart (any version!) then you’ll know about the items you can collect in the “?” blocks throughout each race. As we shared the seven tools, J…
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Who wants to talk about burnout?? Intervening before reaching burnout is crucial skill we’ve tried to learn over the years. How do you know you’re on the cusp of burning out? There are clear signals we’ve noticed: neglecting texts, rushing through moments, feeling unfulfilled despite productivity, brushing only half your teeth 😂, and struggling to …
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This week, we’re all about action taking! We have a handful of tasks you should be able to accomplish this week to impact the growth of your audience and overall business. Here are the 14 quick wins written out: Rewrite your homepage so it speaks to a problem Make your home page lead magnet obvious and enticing Remove clutter from your site that is…
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For the last 5 years we’ve run a paid coaching program that includes a community. During that time, we’ve learned a lot about what works and doesn’t work and thought we’d break down in this episode. We go over 4 crucial parts: The Audience, The Offer, The Community, and The Launches. Not only do we share what has worked for us in each of those four…
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Is lifetime pricing better than an ongoing membership model? What about individual course launches? And what if you only sell a $97 product? We go over all our thoughts on our lifetime pricing model in this episode and answer listener (and customer) questions! There is no perfect way to make money with online business, but from our experience, usin…
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This week, we wanted to share an episode that was a bit more off the cuff. We had a friend visiting for a week, we both got sick, and momentum has slipped from our grasp! Now… what the heck do we do? We share the steps we’re taking to regain momentum and we also talk through the idea of “starting ugly” and what to do with the feelings of wanting to…
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Welcome to the next era of our podcast!!! After 5 years of the name “What is it all for?” we’ve rebranded to Growing Steady. The podcast content itself will stay the same, but it was time to evolve and grow 😉. In this ep, we share the process and thoughts we had around changing the podcast name. We also go through the nuts and bolts of why we chang…
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This week, we share a bit of a roadblock we’re running into while focusing more on our online course software Teachery. And it’s not just one roadblock, it’s multiple, very technical, confusing, and difficult roadblocks 😂😂. Which is especially tough for us because our main business (WAIM) has become such a smooth operator over the course of 5 years…
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To kick off this episode we’re sharing a “mini meltdown” that Caroline experienced the day before recording. We wanted to share that and talk about how we’re trying to reframe using Uncle Jhery as a metaphor/story to continue to move forward when we experience something difficult in growing our second business Teachery. Then, it’s time to go throug…
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Whenever you change something, whether it’s a routine, a process, or pivoting your entire business, there are so many unforeseen ripple effects that will create resistance. We bumped up against a few of these and want to share the emotions and roadblocks we encountered as well as how we worked through them as a team (even if it was difficult in the…
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This episode starts with an important question for 👩🏻‍🦰😂 and then we dive into a brief history of our online course software (Teachery) that’s been a side project for 10 years. We walk you through four essential steps we’re taking this year to take Teachery from an afterthought in our work week, to priority #1! You’ll hear how we’re changing up our…
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We absolutely LOVE doing year end reviews! You can read the written version of this one with a few accompanying photos over at https://wanderingaimfully.com/2023-review If you’ve never done your own year end review, we love the simple format of answering these questions: What went well in 2023? What didn’t go well in 2023? What did you not do on PU…
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After about 5 minutes of research, we realized we *thought* we’d recorded a podcast episode on the idea of practicing “enough,” but alas, we had not done that. We’ve talked about it here and there in a few other eps, but we wanted to have an entire conversation about enough because it’s been so impactful for us. We’re going to walk you through our …
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In this episode, we’re going to chat about the pros and cons of living in Portugal, the biggest differences to the U.S., as well as a handful of lessons learned. We’re also going to talk through a few categories, like our home and neighborhood, making friends, the food, the pace of life, all the admin crap when you move to a new country, as well as…
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We know that running a business can sometimes feel overwhelming, with countless tasks, offers, and marketing strategies to juggle. That's why we're here to help you simplify and streamline your business so you can focus on what truly matters! We also share our own experiences and perspectives on simplification, including how we developed frameworks…
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We open enrollment for our coaching program twice per year and have done so for the past four years. We love sharing the launch recaps to give you the good, the bad, and any lessons/takeaways that might help you with your next launch. We don’t use paid ads, and we aren’t on social media, yet this enrollment period saw the highest amount of customer…
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The Calm Business Encyclopedia project reached its finish line and we’re equal parts excited and exhausted 😂. As with any big, DAILY, content project, the repetitive nature of it can wear you down. While we are a bit worn down, we’re also stoked to have a great resource out into the world to help online business owners (and our own biz!) We go thro…
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This week, we wanted to record an episode about simplifying your business, but also share how we look at a topic that might become one of our coaching sessions or a bigger article/video. If you like hearing how the proverbial sausage is made then you are going to LOVE this one! We walk through how we take an idea and concept and break it down, answ…
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We have this phrase around the WAIM office (aka our living room) that’s the “Straddling Strategist.” It’s the idea that so many people are straddling between two ideas or two businesses and can’t quite go all-in on either. This week, we share a pretty big update as it’s the future of our focus in our work! We sat down last week and had a 3-hour bra…
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