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Before we drop you off in your brand spanking new member dashboard, would you like to take the grand tour?

Calling all creatives, coaches, and client-based business owners:

Build a thriving online course business without burning out

We offer UN-BORING business coaching to help you turn your expertise into a scalable, fun digital product business

textGrow your revenue beyond the limits of your time 📈
textSo you only take on the clients you love 😍
textWith the flexibility to work how & when you want ✌️

If you want online courses to be a game-changer for your business, what you need first is an engaged audience.

But how do you build an audience (much less an online course) when you’re already stretched thin with clients? The answer is with a clear path forward, cash leverage and non-negotiable time. Let us show you how. 👇


You want a clear path forward.

It would be helpful to know exactly which essential steps you need to undertake, so you don't have to waste precious mental resources coming up with a game plan to build a bigger audience.


You want cash leverage.

It would be helpful to build out your client roster and runway so you'd have the financial peace of mind to turn your attention to this future pivot.

You want non-negotiable time.

It would be helpful to eek out just a few more hours a week somehow, but your existing schedule keeps eating up what little time you feel you have.

We teach you how to get all three of these 🗺️💰⏰ in the

Client Off-Ramp 🛝 Starter Kit


How Wandering Aimfully's Un-Boring Business Coaching supports your transition to a digital products business


Un-boring monthly coaching sessions for more focus

Our sessions give you ONE topic to narrow in on at a time so you can see real momentum instead of trying to do it all at once.


WAIM of Stones Accountability for more fun

We host a monthly challenge where you can collect "WAIM-finity stones" when you reach your goals. Ridiculous? Sure. But also highly effective!


Un-Boring Roadmap for more clarity

Not sure what your next step is for max impact? Our 5-step roadmap helps you diagnose your businesses opportunities so you don’t feel lost on how to move forward.


Client Off-Ramp OS for more calm

Notion has completely transformed our business since 2020 and brought peace and calm through a methodical system. We show you how to do the same!


Lifetime access to Teachery for more ease

Making online courses, digital products and payment pages is 10x easier because we offer our course software platform as part of our program!


Slack community for more support

A place where uniqueness and vulnerability are celebrated so you can be yourself and share the highs and lows of your business journey.

Our un-boring coaching program called WAIM Unlimited offers training, tools, & community to help you build a flexible, intentional online business using digital products.

Q: Can online business be used as a tool to improve mental health?

We think it can, because it was for us. Read more about our story. 👇

Hey there! We’re Caroline & Jason Zook—
your un-boring business coaches.

Those photos you see are from our year of full-time travel through Europe in 2022 and our move from California to Portugal in early 2023. Those adventures were only possible because of the freedom and flexibility that our online businesses have provided us.

We found out pretty early on that working for other people just couldn’t offer us the true flexibility we wanted—honestly, needed—out of life. That’s why we traded in our corporate paths in the design and advertising worlds in favor of the riskier, but far more malleable world of entrepreneurship. We’ve been building businesses for 10+ years now (first separately and now together), and the freedom we’ve gained working for ourselves is what we want for every person out there like us.

This freedom has allowed us to stop trying to fit into what society expects from us, and instead design a life step-by-step that is 100% tailored to who we are. This has alleviated anxiety, delivered joy, and brought a tremendous amount of inner peace to us. That’s why it’s our mission to provide comprehensive online business education to more people who crave lives of more ease, flexibility and creativity.

Some fun facts:


While Jason would like to share his love of cinnamon rolls as a fun fact, a more interesting tidbit is that at 6’5, he can do a flawless cartwheel!


After one vivid dream in 2015, Caroline taught herself to paint and successfully sold her paintings and prints under her previous art business, Made Vibrant.


We're movie lovers! Since 2019 we've hosted a Classic Movie Night every Saturday night where we watch two movies (preferably terrible ones) and laugh-cry at the cringiest moments.

Here’s how we’re different

We know there are a lot folks out here teaching business, so you may be wondering "What makes these Zooks the right coaches for me?" Here are a few things we do a little differently than most coaches out there.


Enough-based goals

Hustle culture, begone! Our approach is about reaching for enough so you can stop chasing more all the way to burnout. We help you define what satisfaction looks like so you know it when you feel it.


Emphasis on un-boring

Emojis! 🙃 Weird metaphors! Acronyms that make little sense. The occasional fart joke. 🫣💨 We believe online education is wayyyy too serious, so we try to sprinkle FUN into everything we do in our business. .


Nuanced teaching style

Quick Q: did you know every person is... different? Yeah, we thought it was pretty obvious too, but a lot business teaching out there is very one-size-fits-all— which is frustrating. Our teaching style leaves room for your unique perspective.


Real business experience

We have hands-on experience with different biz models, not just regurgitating what we've learned from others. We've sold sponsorships, art prints, design services, speaking, memberships, software, and more. We love putting what we preach into practice.

Take the 3-minute quiz!

Which of these is your Calm Business Bottleneck and how can you fix it?

As business coaches, we often see these are the 5 major roadblocks keeping people from growing a profitable AND peaceful online business. Find out which one might be affecting the growth of your business, and we'll give you our best tips for fixing it starting right now.