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 (un-boring) coaching program are currently closed. Our upcoming enrollment period is August 26 - September 9. Join the waitlist below!

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Wandering Aimfully


Let us show you exactly WHAT to improve in your online business and in WHAT ORDER, so you can grow your revenue and live a more spacious, satisfying life.

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Have you thought lately:

"I know my online business isn't working like it should, but I have NO IDEA what the key problem is."

Do you feel like you KNOW there are ten different ways you could be improving your marketing, or honing your messaging, or building an audience… but you’re overwhelmed with the thought of doing EVERYTHING, so you end up doing NOTHING?

We get it. Finding focus and clarity has always been hard, but it’s gotten 10x harder in these rapidly changing and uncertain times we’re living through.

But what if you were finally able to PINPOINT the areas of your business that need the most urgent help, and you had someone telling you how to fix them (and in what ORDER!)?

How good would it feel to stop trying to do it all, and instead methodically improve one aspect of your business at a time so you could start seeing real momentum?

That’s what we want to help you do with our Wandering Aimfully (WAIM) Unlimited Coaching Program and our Monthly Un-boring Coaching Sessions within it.

With our help, you’ll be able to shake up the patterns and habits that have been keeping you stuck, and you’ll have a practical plan to get more revenue in the door—all at a sustainable pace that works for YOU.

How good would it feel to stop trying to do it all, and instead methodically improve one aspect of your business at a time so you could start seeing real momentum?
Here's The Problem:

Being an entrepreneur requires you to pay attention to SO MANY puzzle pieces at one time and try to fit them together seamlessly. Creating content, honing your messaging, crafting a compelling offer, branding that stands out in a saturated space, the list goes on. And it’s A LOT. Which is why you probably feel pulled in ten different directions, not making REAL progress on any one thing.

You’re left feeling stagnant because it’s hard to feel momentum when you’re filling up twelve buckets one drop at a time.

But Here's The Solution:

When you give yourself permission to prioritize ONE major thing in your business every month, you know you can see real growth in at least one area of your business because you took action instead of letting the overwhelm takeover.

Even better, what if YOU didn’t have to be the person choosing what that one thing is? What if you let us take that off your plate and you just showed up each month, ready to learn something new and experiment with new strategies to improve your business. When you stop trying to do everything and go deep on one thing at a time, that’s when you’ll really start to see progress.

That's why WAIM Unlimited comes with monthly...

Un-Boring Business Coaching

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.

We have 50+ past coaching sessions, each focused on a different business skill for you to develop. If you're not sure where to start, don’t worry—we have our Un-Boring Business Roadmap that will point you straight to the area we think you should begin, all based on what you’ve already tried in your business (more on the Roadmap below!)

Our sessions span a wide range of business topics so you get the most comprehensive program when you join WAIM Unlimited. Here’s just a small taste of session topics included:

  • Content Strategy
  • Copywriting
  • Project Planning
  • Selling & Sales Launches
  • Debt Payoff & Budgeting
  • Live Workshops
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Not only will we teach you our business strategies, we’ll show you how to apply them!

You’ll also get six recorded monthly coaching sessions where we feature one lucky WAIM Unlimited member and their business as a case study, showing you exactly how we’d improve their business using our Un-Boring Business Roadmap framework.

We call this coaching session format: Unsolved Businesses! 🕵️‍♀️🕵️‍♂️

Watch a sneak peek of an un-boring coaching session!

That's right, if you want to get a real feel for the quality we pack into every monthly coaching session, you can watch one FREE from start to finish right here.

Note: When we say "un-boring," we mean it. Prepare to have a few giggles!

every session comes with:

→ 📺 LIVE two-hour video training session every month on the topic where you can chat with us and fellow WAIMers!

→ 🏆 Accountability to help you actually follow through on implementing what you learn with weekly action steps—complete your goals and collect our WAIM-finity stones!

Teach Roadmap (1)

"Teachery Field Notes" Sessions Through 2024

In 2024, we have a NEW format for our monthly coaching! Every month, you’ll go behind the scenes with us to see how WE are applying the Un-Boring Business Roadmap to our second business, Teachery, in real time! Teachery has always been our secondary focus, but we are finally aiming to go ALL IN and attempt to double Teachery’s revenue in 2024.

Every month, you will see us focus on ONE aspect of growing this business. You’ll see us apply the same roadmap we teach inside WAIM Unlimited, and you’ll also see the true transparent results. Every experiment, every challenge, every decision—you get a front-row seat. If you are the kind of person who learns by watching others DO, you are going to LOVE this monthly format! (And of course, we’ll have monthly action items for how you can apply each and every strategy we use to your own biz!)

If access to all these coaching sessions overwhelms you, fear not! We've created a content hub that outlines a specific order for every single session so you know exactly where to begin and how all these tactics fit into your overall business strategy. It's called the:
Un-Boring Business Roadmap.
the roadmap

How does it work?

We’ve developed a methodical, five-step roadmap for improving your business and boosting your revenue from years of helping hundreds of entrepreneurs in their businesses.

The roadmap is based on a decision tree flow chart meant to guide you straight to the action step that will have the greatest impact on your business. Want a sneak peek? Use the button to view the flow chart and check it out!

  • 14

    Set a strong foundation.

    In this step you'll focus on defining the core aspects of your business that will inform your marketing strategy and you'll fortify your own mindset and processes, as neglecting these things can actually be limiting your progress further down the roadmap.

    You'll learn how to:

    Generate endless business ideas.


    Answer the 4 foundation questions of a business.


    Define your business goals & organize your finances.


    Develop an entrepreneurial mindset.

    Define a system for getting shit done.


    Design an authentic brand identity.

  • 06

    Improve your offer.

    Once your foundation is set, in this step you'll evaluate the core thing your business sells, whether it's an online course, membership program, or client service packages. Before you improve your marketing, it's crucial that you know you're selling something people want, and that you're communicating the benefit in a compelling way.

    You'll learn how to:

    Determine your core product offer.


    Create and produce your core offer.


    Learn to communicate your message effectively.


    Get in the selling mindset.


    Craft a sales strategy to sell your offer.

  • 03

    Architect your marketing bridges.

    Once your core offer is locked in, now the experimenting really begins! The vast majority of business owners we talk to who aren't seeing the sales they want actually just have a breakdown in their marketing strategy, or what we call "marketing bridges." In this step you'll learn how to map our your customer's journey to buy from you and you'll be able to identify whether you have gaps in that journey you need to fill.

    You'll learn how to:

    Set your marketing strategy and customer journey.


    Attract an email audience of potential customers.

  • 04

    Produce more content.

    So many people focus their time on creating social media content, but what if we told you there was a way to create content TODAY that would still pay dividends years from now? With your marketing bridges set, at this step you're in a great place to super-charge your traffic and publish strategic content designed to attract your ideal buyers.

    You'll learn how to:

    Create strategic content that attracts your ideal audience.


    Gain brand awareness using Instagram (optional)


    Consider creating a podcast (optional)

  • 04

    Optimize your website.

    Finally, your website is the arena where your marketing strategy gets put to the test. So many people START at this step, but we promise you, if you go through each previous step in this roadmap, your website will feel like a piece of cake to update because you'll know exactly what role each page plays in your strategy, and you'll see how your site serves your bigger business goals.

    You'll learn how to:

    Create a strategic website for your business.


    Adjust your website design to support your evolving marketing strategy.


    Optimize your website based on your analytics.

The Result:
Every month, every week, every day, you have a CLEAR idea of what work you need to focus on to improve your business. And when you have a clear focus, you finally start to see a boost in your revenue and more space to breathe.
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“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."

"WAIM has helped my Made on Sundays biz revenue grow 101% since I joined! On top of that, I’ve been slowly able to shift my business to more diversified income streams, helping me free up more time and grow a more sustainable business. I can't thank Jason & Caroline enough! The business mindset shifts I've been able to see in myself are incredible, and makes me so proud of the biz owner I've grown and will continue to grow into."

- Cheryl Chan

"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

Have you thought any of these things to yourself?


"I know the business I want to be running, but I’m not 100% clear how to position it to a potential customer so they’ll buy from me."


"I know I’m supposed to create 'content' but between articles, videos, podcasting, and social media, I’m 1000% overwhelmed and don’t know where to even start."


"I know marketing and audience growth are important, but I don’t want to spend all my time doing those things. I wish I had a clear marketing plan I could follow so I can spend time on creating."

WAIM Unlimited is designed to be a solution to these problems.

And this is right about the point where you find yourself asking...

Okay, okay, just get to the punch line...

How much does this program cost?

As a smart business owner, of course, you're going to ask yourself:

Is what I get with WAIM Unlimited worth MORE than what I'm going to pay? And to be honest, we're glad you're thinking that because that's what we're asking OURSELVES all the time too! We want you to spend your hard-earned money on something that will bring you results. So we'll tell you... our program is a LIFETIME price of $2,800 (meaning once you complete your payments, you don't pay us again!), and this is our most popular plan:

Our Most Popular Plan:

28 payments of



So, now the question becomes...

Is it worth $100 per month?

We believe without a doubt it is, but to prove it to you, let's play a little game! Scroll down, and when you feel it's worth $100 per month to you, click that handy little link to join us. 🤝 Deal? Let's do it.


Wanna see how we organize all the awesomeness in WAIM Unlimited for you?

Watch this inside look at our new and improved fully-custom members-only dashboard!

"What makes WAIM Unlimited different than other coaching programs?"

We're so glad you asked!


Transparent realness, not silver-bullet promises

We love sharing EVERYTHING with our members. The good, the bad, the ugly, so you can learn along the way with us.


Success defined by more than "six or seven figs"

We aren’t about that “figs” life around here. Yes, we like money as much as other people, but success is more about living a balanced life.


The belief that business doesn't have to be boring

Silly emojis, cheesy dad jokes, LOL-worthy GIFs, we’re all about making business coaching fun and enjoyable.


What is all your hard work FOR if you’re not enjoying your LIFE in the process?

Our goal is to always remind you to enjoy the journey WHILE you reach for your goals.

Hello there, fellow human 👋:

(Unless you’re an alien 👽  reading this, then, well, hello to you too!)


We wanted to take a moment to speak to you like an actual *person* (not a sales page) and to be brutally honest about a few things as you’re thinking about joining our WAIM Unlimited Program…


Thing #1: Inclusivity

First and foremost, we care deeply about our WAIM family. We aim to welcome and celebrate people of every race; ethnicity; gender or non-gender; sexuality; mental, physical, intellectual, and sensory disability; neurodiversity; body size; or any other characteristic. It's important to us that we treat everyone as being on the same “level” within WAIM, regardless of where you are in your business journey. If that's not cool with you, or if you're adamant about denying the existence of real things like systemic racism and discrimination, WAIM is not the right fit for you.


Thing #2: No Dream Selling

We do NOT "sell the dream" and we do NOT have a “foolproof plan to guarantee you $100,000+ (6-figs!) in your business.” Many other business coaches want to promise you the moon when they only end up delivering you unmet expectations and searching for the next coach or program. That’s not us. Do we have a business roadmap for you to follow? Heck yeah, we do! Has our roadmap and monthly coaching program helped our members reach success on their terms? Abso-freaking-lutely! Can we guarantee any amount of success for you? No, we cannot, and neither can anyone else. All we can do is share our huge breadth of *actual* business experience and give you practical steps to follow while being there to support you along the way. Getting people to buy into the dream is easier, but it's not REAL. If you're tired of buying into empty guarantees, we're glad you found us.


Thing #3: Real Business Experience

We don’t just make money teaching people how to make money. In fact, we openly admit that we aren’t great at things like creating passive income funnels and FB Ad growth machines. What we ARE good at is defining what actually matters in our lives, building profitable and sustainable businesses that support our specific goals, and ensuring that the systems and processes are in place to avoid burnout at all costs. While we do focus on helping people build profitable online businesses, our actual business experience comes from running design/marketing agencies, working with clients, selling a variety of courses, getting books traditionally published, building a physical art business, doing paid public speaking, creating and selling software applications, and many other business experiments since 2006. You get the benefit of that wide range of experiences when you're in our program!


Thing #4: No Business Bullshit

We are all about honesty and transparency. We have shitty weeks and we have up and down moments in our businesses just like you. Anyone who wants to pretend otherwise is lying to you. We keep it REAL and we share our mistakes and missteps with you so that you can try your best to avoid what we do wrong. If you’re looking to learn from a “perfect business coach,” that’s not us. 


To sum this entire section up, we want you to know we care. We care about constantly learning how to be better people. We care about having the mentality of “enough” when it comes to money. And, we care about being available to you and being part of your unique journey in business (and life).

If all of this resonates with you, then hell yes, keep reading!

⚠️ Halt! ⚠️

Before you join WAIM Unlimited, we think it’s important you know a bit more about who you’re learning from.

We want you to be able to make the most informed decision possible about whether we are suitably equipped to support you on your business journey.

That includes knowing more about our backgrounds, perspectives, experiences, privileges, limitations, strengths, and struggles, as these form the unique lens with which we coach our business owners inside WAIM.

First, let’s start with privilege. This is important because every person moves through this world with a unique set of unearned advantages or uncontrollable disadvantages, and us being honest about those things will help you take our experience with the necessary context. We recognize that we are two cisgender, heterosexual, white, able-bodied people, and this often means we have gaps in our knowledge when it comes to the lived experience of people who have been marginalized and oppressed due to race, gender non-conformity, sexuality, ethnicity, disability, neurodivergence, etc. It’s our job to educate ourselves on experiences outside our narrow perspective, to always aim to do better the next time when we screw up, and to apologize when those gaps in our knowledge cause harm.

If you are a person who has been marginalized because of your identity, we want you to know you are welcome in our community and we hope you feel celebrated for exactly who you are.

That said, if you feel you'd be better served by coaches who share your same lived experience and who can fully relate to your unique challenges and triumphs, we want you to know we honor that inner wisdom and encourage you to seek those folks out! Choosing a coach is an incredibly personal decision, and we just hope you find the right support to help you meet your business goals and chase a beautiful life!

More Details about Caroline's perspective:

I identify as a Highly Sensitive Person, which means I have to be very mindful of the energy I absorb, the stimuli I expose myself to, and taking rest when my body and mind become depleted. I don’t have the same work capacity as someone who may not be an HSP, and that’s okay! You’ll hear me talk about this often in our sessions. I have also struggled with an anxiety disorder for most of my life. I experienced a sort of rock bottom with my anxiety in 2019, but since then I have been able to develop many coping strategies and have invested in difficult but necessary therapy to thrive in spite of my mental health challenges. I'm happy to say that most days now I don't even think about my anxiety! 🙌 This journey has clarified for me that mental health is the #1 most important priority in my life. I believe whole-heartedly in trauma therapy (specifically EMDR) with a licensed professional, and while Jason and myself are NOT therapists (nor do we try to be!), you will probably hear us discuss mental health and therapy often in an attempt to de-stigmatize these kinds of conversations.

More Details about Jason's perspective:

Hi there, my name is Jason Zook and I am a recovering “hustle bro.” Over a decade ago, I ran a social media marketing company, and during the five years of building that business I believed in working 80+ hours per week, burning the candle at every available end, and I preached the gospel of more, more, more. Since that time, and after a pretty gnarly dose of burnout between 2013-2015, I’ve realized that there were a lot of toxic productivity thoughts I was sharing out into the world. At that time, I believed everyone made their own luck, had all the same opportunities as me, and just needed to “work harder.” That’s absolute utter bullshit and I apologize for previous-Jason and all of the ways he didn’t understand his inherent privilege and advantages. I try really hard these days to understand and embrace that we all have unique life circumstances and “working harder” is not just something you can snap your fingers and do, nor is it even a guarantee of the same outcomes across the board. I’ve learned so much about supporting and understanding people who think differently than I do and who have a brain that operates differently from my own. These days, I am happy to encourage folks to work at THEIR pace, using whatever amazing skills THEY bring to the table, and if I can help offer support, I’m happy to do it (but I’m also happy to take a backseat too!)

Listen, we’re going to let you in on a secret here…

You don’t actually need more information;
What you actually need is focus and consistency.

That’s what our business coaching is designed to bring you.
So, here are the 4️⃣ things we promise you inside our WAIM Unlimited 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 and focus 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 Sheila in Accounting to talk your latest Netflix obsessions because Sheila 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 or tea and suddenly you feel like all systems are a go and now you’re an ACTUAL superhero and can do anything?

Wandering Aimfully Unlimited 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 in return you promise...
1. You’ll show up and do the work.

You will check off those monthly action items with the enthusiasm of someone who just discovered there’s still $20 on that five-month old Target gift card.

2. 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.

3. You’ll ask for help when you need it.

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.

"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

WAIM Unlimited

We’ve developed a methodical, five-step roadmap for improving your business and boosting your revenue from years of helping hundreds of entrepreneurs in their businesses.

  • ✓ Access to ongoing monthly live coaching sessions through December 2024
  • ✓ WAIM Unlimited Un-Boring Roadmap with 50+ training sessions and workbooks with clear action items
  • ✓ Free lifetime access to our course platform, Teachery (Make all your online courses for FREE!) & the Teachery Theme Pack
  • ✓ The Notion Starter Pack
  • ✓ The Page Layout Library
  • ✓ Access to our private WAIM Slack community
  • ✓ Access to the WAIM Vault with specialized courses and workshops
  • ✓ Whatever we create in the future at no additional cost!
Enrollment closes in:
 Sorry, friend! WAIM Unlimited is currently closed for enrollment! It opens back up August 26.

Enter your details below to join our newsletter and make sure you get notified when WAIM Unlimited becomes available.

About Us Photo 2023
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 15 👴, her for over 7 👵. We technically met on Twitter in 2010 🐦, when Caroline was still pursuing a career in advertising 💼 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. 🌊⛰👰🤵💍🍩🍹💞 In 2022, we left California to travel Europe full-time for a year 🛫🗺️ and ultimately landed in Portugal 🇵🇹, a stunning country we now call our home.

Her superpower is self-reflection 🧐; 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 binge-watching old seasons of Survivor. 🪃

Frequently Asked Questions