Profile Complete!

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

Sorry, Charlie! The doors to our coaching program are now closed! Join the waitlist below!

Un-boring business coaching to 🤑 boost your revenue without 🧘‍♀️ sacrificing your values.

Get support from our private community and two-hour live coaching every month teaching you the strategies, tactics, and mindset-shifts you need to grow your business WHILE staying true to the lifestyle you want.


What if you knew exactly what to do to get more clients or customers WITHOUT using shady marketing tactics or working until dark every night or staring at your to-do list with an overwhelming sense of dread? 🤔

Would you finally be able to rest easier at night or look at your bank account without breaking into a cold sweat?

Would you take that vacation with your family and trust that things wouldn’t fall apart?

Would you see a movie in the middle of the day or start giving to that charity that’s been on your heart or spend the weekend playing with your kids rather than desperately trying to “catch up”?

The thing is… you have the ability to live a more freedom-filled life TODAY, exactly where you and your business are right now.

What’s stopping you are the patterns, limiting beliefs and habits that have become automatic.

All you need is a little outside help 👩🏻‍🦰👨🏻‍🦲to INTERRUPT business-as-usual and bring you back to your most passionate, productive, and confident self.

Maybe you think everyone knows some secret that you haven’t figured out yet.

Maybe you’ve invested in courses and memberships and webinars and conferences and you have a mountain of PDF’s saved in a desktop folder collecting dust. 🙈

Maybe you’re afraid to go all in on one more thing because you can’t take the disappointment of another year gone by without anything changing.

But we’re going to let you in on the big secret™ right now…

You don’t actually need more information. What you need is transformation.

You need an outside force to help you shake things up and get you out of your head. You need people in your corner that will challenge you to take the risk, make the ask, do the thing, stop the waiting…and over-thinking…and postponing.

Do we have tactical tips and processes that will help your business grow? YES. ✅

But we’re honestly more driven by seeing you grow into the person that boldly and confidently puts those plans into ACTION.

We have stumbled through the dark, gotten banged up and bruised so that we could light the path for you. Can you find the courage to walk it? We hope so.

Okay fine, The Big Secret™ is actually that until last year Jason thought Moulin Rouge was the sequel to Mulan. And, honestly, Caroline sometimes pees in the shower but she swears it's involuntary because the water is WARM, OKAY?!


So, here are the 4️⃣ things we promise you inside our coaching program.


Have you ever heard that phrase: “It’s hard to read the label from inside the jar?” When you’re IN your business every day and you’re wearing all the hats and doing all the things, it’s easy to feel like you’re lost in a forest of tangled paths.

You get so stuck in the weeds and the million different decisions you have to make that everything starts feeling muddy and uncertain. Our job is to periodically bring you back to your TRUE path with crystal clear focus. No matter how many dead-ends you walk down, no matter how many wrong turns you make…

…you’ll find your way back to clarity with the tools and processes we share.


We believe whole-heartedly that business should be FUN. Because what is all of this hustle for if it’s not lighting you up on a daily basis?

As business owners, we often focus on the destination (X revenue goal, X many followers, X many email subscribers) and we forget that the milestone is such a small segment of time compared to the journey. If you’re bogged down, burned out, and feeling uninspired, we will share as many gif stickers, emojis, jokes, and dance parties as it takes…

…for you to feel the joy again in your business.


The truth is, having an online business can be freaking LONELY. You can’t just mosey on over to Karen in Accounting to talk your latest Netflix obsessions because Karen in Accounting is YOU.

You wonder if you’re struggling because you’re just not cut out for this whole entrepreneurship thing, but you’re only doubting yourself because you can’t see that everyone else is just figuring it out too. Our community is full of intentional, kind, open-hearted doers who will make you feel seen and supported and…

…we will be right there among them always eager to cheer you on.


You know how you wake up and you’re a lifeless zombie and then you have that first cup of coffee and suddenly you feel like all systems are a go and now you’re an ACTUAL superhero and can do anything?

Wandering Aimfully Coaching IS that cup of coffee for your business. People think of motivation as a myth, but it’s a very real thing. It’s a FEELING. It’s an energy. It’s that spark that lights up your potential and reminds you of your own power. We promise to be the ones encouraging you when the lights have dimmed and you’re feeling unsure. We will be…

…the caffeine injection you need to remind you of your own potential whenever you need it.


And here's what YOU will promise us in return:

You will show up and do the work.

All the knowledge and tactics and processes in the world can not do it for you. Knowledge is power but only if you USE IT. You will commit to showing up each month to our coaching sessions with an open mind and an action-taker’s heart. You will check off your monthly action items with the enthusiasm of someone who just discovered there’s still $20 on that five-month old Target gift card.

If you fall, you BOUNCE BACK.

When life gets busy or you fall into old patterns, you will not shame yourself or feel like a failure for falling off the wagon—you will act like you just fell onto an Olympic-sized trampoline and you will double-somersault your way back into action with excitement and resolve to give it another go.

You will ask for help when you need it.

When you join us, you’ll quickly learn that we LOVE helping people solve business problems. Seriously, we consider business one of our hobbies we like it so much. We want to be in the trenches with you, helping you figure out what moves the needle. But we aren’t mind-readers. We don’t know how to help you if you don’t tell us HOW. The benefit of being a small business is that you don’t talk to moderators or assistants…you talk to US. But this is only a benefit if you’re willing to be vulnerable and ask for what you need.

Listen, combined we have 15+ years in the online business game. We’ve experimented with selling services, courses, bundles, art, workshops, memberships, the list goes on…

Why? Because we won’t teach it to you if we haven’t tried it first. 🙌

No second-hand knowledge schlepping here!

We DON’T love talking “figs” around these parts, but if it leads to a HELL YES for you joining us, we’ll happily share. We have consistently made a multiple six-figure income online since 2014. That doesn’t mean we haven’t had failures or missteps like you, but we hope it shows you that we know what we’re talking about, and, more importantly, we believe that is achievable for you too—whatever your version of financial freedom is.

Listen 2@2x-Compressed

Learn clear processes

to implement now


Get Re-inspired

on a regular basis


Form connections

with fellow biz owners


Save yourself time

by learning from our experience


Ask us anything

and get direct feedback


Wandering Aimfully (WAIM)

Un-boring monthly programming and support to FINALLY gain momentum in your business without burning out in the process.

🚀 Boost your revenue. ⏰ Gain free time. 🎉 Have more fun.

What you get:

→ 📺 LIVE two-hour group coaching video session every month on a tactical topic that will move the needle in your biz

→ 📓 Companion workbook with clarity-inducing questions and clear action items to implement what you’ve learned

→ 🌎 Access to our private Slack community bustling with an international group of like-minded business owners who are only interested in sharing the raw, REAL experience of being an online entrepreneur

→ 👫 Direct access to US! No moderators here, just Jason and Caroline ready to answer whatever questions you have!

→ 🏆 Accountability to help you actually reach your goals through 1-on-1 weekly Slack check-ins with Jason

Next COACHING session:

September 30, 2020

What you'll learn:

Masterfully Managing Memberships 👥✅

How to create, manage and sell memberships as a revenue model

Join now to register for this session ↓

What our program members have to say 😍:

“I remember the feeling a few years ago when $10k/month was only a dream. Today, that’s a reality and I’m loving the freedom and the flexibility it allows me to create more products, spend time with my community, and provide consistent income for my family."

"I’ve been saving an average of $700 a month just from one Wandering Aimfully exercise. I finally feel in control of my numbers and income goals and have solid data to base them off instead of imaginary numbers in my head."

"In my first month, WAIM paid off huge for me. I just have to say that I’m super appreciative for WAIM. At the end of a long workday, after getting kids to bed, a dog walked, a lawn mowed, etc… I’m exhausted. The simplification of the WAIM Unlimited (getting all the past courses) is AMAZING. It keeps me moving even when I only have 15 minutes in an evening. And while there is no way I can possibly be on Slack as much as I want to, it’s awesome having engaged people that are interested in helping each other when I do jump back in. Cheers to you fine people of WAIM, cheers to you!"

- Jeremy Smith

"I’m on pace to triple the income I was making in 2016 as an assistant principal before I joined Wandering Aimfully. This year I launched my first serious course in an attempt to keep building without burnout. Even with a super tiny email list, I made $8,000."

- Brendan Hufford
Read the full case study →

"I saved $2,000 annually using the Build Without Burnout expenses exercises (which saves me almost double what it cost me for to join). Within 4 months of joining Wandering Aimfully, I launched the beta round of my first live branding program that brought in $1,500, which was about 10x what I've ever previously got from 'launching' courses."

Read the full case study →

"Caroline and Jason both share so much value by showing the nitty gritty detail-y stuff. Their thoughts/inputs when someone asks a question in Slack and how they put their business on display are the premium product in WAIM. I just love them, their creative entrepreneurialism, and look forward to continuing to follow their process!"

- Cynthia Luna

Okay, now I'm pumped!

Still wondering exactly what you'll get every month?

No sweat. 😅 Keep this train scrolling to find out! 🚂
group coaching Part one:

📺 Live 2-hour group coaching video call every month.

We believe there’s nothing like the revitalizing energy that comes with showing up LIVE. During these private group coaching sessions, you can expect a few awesome things:

  1. UN-BORING teaching on one tactical business strategy that you can implement immediately.
  2. We’ll peel back the curtain on the latest “experiment” we’re running in our own business so you can use us as guinea pigs to test out different marketing strategies.
  3. A two-week action plan so you know exactly what to do AFTER the call is over.
  4. A Q&A session to ask us anything AND chat in real-time with like-minded fellow entrepreneurs.

Our intention is always to make these live sessions simple, actionable, unique, memorable, fun & energizing. We want you to leave these coaching sessions feeling UNSTOPPABLE. 💪

part 1 photos@2x-compressed
workbook photo@2x-compressed
Group Coaching Part Two:

📓 An action-oriented workbook so you can APPLY what you learn.

We don’t know about you, but we LOVE a good workbook. It’s so much less daunting to take action when you have prompts, exercises and clearly-outlined steps to light the way. Each month, we’ll deliver to you the monthly coaching workbook 1-day before our session so you can use it to take notes AND you’ll have follow-up checklists and thoughtful questions so you can start applying what you’ve just learned. Print it out or fill it in digitally, but you’ll start accumulating a library of powerful resources to move your business forward.

Group Coaching Part Three:

🌎 Use the private Slack community for support, feedback and feeling connected to fellow business owners.

If there is ONE thing we hear over and over it’s this: Wandering Aimfully coaching is worth it just for the community alone. We pride ourselves in attracting a group of kind, supportive, vulnerable, fun-loving entrepreneurs. This is not the kind of community where everyone is trying to “network” all the time or compete or one-up each other. This is a place where you can be yourself, share your struggles, feel seen and understood by people like you, and get your questions answered. As a bonus, many of our members end up hiring each other for work and meeting up in real life!

community photo@2x-compressed
direct access photo@2x-compressed
Group Coaching Part Four:

👨🏻‍🦲👩🏻‍🦰 Get direct access to us—not our assistants or butlers. (Yes, we obviously have multiple butlers.)

Here is the biggest difference between us and other coaching programs out there: we are not just figureheads. We don’t believe in taking your money and then you never hear from us again. We show up for our people, we answer questions, we hop on calls if you need us, we help you figure things out because WE LOVE IT. We transformed our lives through online business and our driving motivation is to see YOU change yours too.

Group Coaching Part Five:

🏆 Opt-in to our Momentum Mondays (patent not-pending) accountability program

Maybe other programs haven’t worked for you because those habits, patterns and limiting beliefs have gotten the best of you. That’s okay. We are all human and our mental conditioning is POWERFUL. But the question is if you’re going to let those things hold you back forever or take steps TODAY to change the outcome. We have a built-in accountability structure to help you bolster that willpower with some outside support. Every Monday, you'll DM Jason (yes, it's really Jason!) on Slack a list of 3 things you intend to accomplish in the week ahead, as well as the 3 things from the previous week you either did or didn't get done. This is not meant to shame you or make you feel bad if you weren't able to get to everything; it's to FINALLY hold you accountable to following through on your intentions and finishing what you say you're going to do.

accountability photo@2x-compressed

📈 Boost your revenue.
🌬Get some breathing room.
🌈 Design a business that leads to more FREEDOM.


Wandering Aimfully (WAIM)
Coaching Program 🏋️‍♀️


By now, we know you're probably thinking to yourself... okay, Jason & Caroline, I'm into this whole coaching thing but what's it going to cost me? For private 1-on-1 coaching we have charged $500/month or $1,500 for an in-person strategy session. In our monthly sessions, we share similar mindset-shifting advice and tactical action steps that we share in our private coaching—you just get to do it with other humans by your side and...

...for a fraction of that price.

Enrollment period ends in:
Sorry, friend! Coaching is now closed for enrollment!

Enter your details below to make sure you get notified when WAIM Unlimited becomes available (which will include recordings of our monthly coaching sessions.)


Trust us, we know that this kind of monthly investment is no small thing for you. But we also know...

You likely won't change those patterns that aren't serving you until you commit to something you truly value.

The FREE PDFs and video workshops and $39/month memberships will give you the information, but they are far less likely to give you that

Remember, if you commit to WAIM today, you are showing up for yourself to say:

I will show up and do the work.
If I fall,
I will ask for help when I need it.

You can DO THIS.

"I used to be addicted to online courses and subscribing to newsletters and learning whatever I could from whoever wanted to teach me. After an overwhelming amount of overwhelm, I’ve since cut much of it out of my life. I have chosen a very few people as my teachers, as people I want to keep listening to in this noisy world. I knew I wanted to learn from people with your energies: fun, vibrant, authentic (I could go on …) I don’t know how you do it, but the live topics are always timely. Thank you so much for being you, and for somehow knowing what I need to hear."

- Kristen Otenti

"There is a certain dynamic and energy that Jason and Caroline bring to coaching sessions that's hard to describe. You can tell they actually know what they are talking about, and have tested out what they are presenting firsthand. They focus on helping you with real issues, and provide actionable advice that isn't overwhelming and just works."

- Edward Danilyuk

"Taking the leap to be a part of WAIM felt big for me months ago, and now I don't know what I'd do without it. My Mom has been a coach for 20 years, and she's noticed a difference in how clear I am, how I'm approaching my business so much more confidently, and how I'm inspiring her to do more with her business since I started working with you."

- Bridget Baker

"I've been part of a lotttttt of online communities and joined a lotttttt of programs, but there's nothing quite like WAIM. Learning from you both has been SO DAMN REFRESHING and makes it so much more simple, easy and fun to execute. Carol, we ADORE those incredible workbooks you work so hard on...and Jason, I'm convinced you're a robot because the way you love on the community is beyond anything I've ever seen."

- Ash De Filippis

"Since I joined WAIM, I felt like I joined a family of amazingly warm and awesome people and the coaching was no different! It felt like I was chilling with some friends that know a lot about a certain subject and are super excited to share their knowledge! ...I really like your approach. Oftentimes I feel like these coaching things are too dry and very number oriented and too businessy. I REALLY want my business to bring me joy and serve my lifestyle and your approach is just that!"

- Julien-Pier Belanger

"WAIM Coaching (and WAIM Unlimited in general) is the best money I've ever spent. I'm a recovering course + program + buying all the business things junkie, so that's saying a lot. I watch the replays (because, timezones, and I need sleep) and I love being able to pause + take breaks to really mull things over. You stay true to the name of unboring coaching and I love watching the sessions knowing that 1) I'm going to learn something super practical and 2) I'm probably going to spit my tea across the room because you both make me laugh. Thank you so much! You guys are the best!"

- Brogan Micallef
About Us @2x-Compressed

Who are your coaches again?

Hey there!

We're Jason & Caroline Zook. 👨🏻‍🦲👩🏻‍🦰

We are best friends 👫 and business partners 🤝who have been at this online business gig for years—him for over 10 👴, her for over 5 👵. We technically met on Twitter in 2010 🐦, when Caroline was just a college advertising major 🎓and Jason was at the height of his first crazy entrepreneurial adventure where he earned $1,000,000+ wearing t-shirts 👕 for a living (Yes, really! Google it.🔍) We've been together ever since, and we made it official by eloping on a cliff overlooking the ocean in March of 2017. 🌊⛰👰🤵💍🍩🍹💞

Her superpower is self-awareness 🧐; his superpower is action-taking ✅. She's an Enneagram Type 4 (Individualist)🎨; He's an Enneagram Type 8 (Challenger)🙅‍♂️. His guilty pleasure is Dragon Ball Z 🐉; hers is anything Bachelor-related.🌹

Frequently Asked Questions

Whoa, you made it to the bottom!

Are you up for a little emoji challenge?👍🥇❓

You didn't realize it, but you've been practicing for this moment all your... well... all the time you've been scrolling this page.

Once you join Wandering Aimfully with either package listed above, if you can correctly guess ALL FIVE movie titles whose "emoji plots" are listed below, we'll give you $50 off your first month.

Why? Because we're weird like that and we think online business education doesn't have to be BORING. Neither do sales pages! Give it your best shot!

Once you have your guesses: join using one of the plan options above and then shoot us an email with your guesses and we'll let you know if you won!

Here's an easy one to get things started: 🍫🏃‍♂️🍤🏓👨‍👦.
Any guesses?... Forrest Gump!

Now, on to the real ones. Take your best guess!

1. 🍀👮‍♂️🍺🐀🔫

2. 👽💬👩‍🏫⌚️👩‍👧😱

3. 🤗🏌️‍♂️🐊🤚🏠

4. 🧑🏻👴🏻⏳🔫♾

5. 🥄☕️😳🏃‍♂️🚪