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.
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”?
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.
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?!
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…
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…
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…
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…
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.
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.
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.
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.
to implement now
on a regular basis
with fellow biz owners
by learning from our experience
and get direct feedback
“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!"
"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."
"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."
"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!"
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:
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. 💪
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.
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!
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.
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.
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...
Enter your details below to make sure you get notified when WAIM Unlimited becomes available (which will include recordings of our monthly coaching sessions.)
"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."
"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."
"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."
"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."
"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!"
"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!"
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.🌹
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.
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!
Now, on to the real ones. Take your best guess!