Why Wandering Aimfully is the Best Online Community for Values-Aligned Entrepreneurs
If you’re a small business owner searching for an online community that goes beyond hustle culture, Wandering Aimfully (WAIM) might just be the haven you’ve been looking for. Founded by Jason and Caroline Zook, WAIM is an online membership that combines business coaching, a treasure trove of educational resources, and a supportive community—all grounded in deeply intentional values.
As someone who has been a member since 2017, I can confidently say this is one of the best investments you can make in yourself and your business if you’re not quite ready for the step into personalized, high-level coaching.
In this post, I’ll outline the pros and cons of Wandering Aimfully, why it’s such a fantastic fit for service-based entrepreneurs, and how it might be exactly what you need to grow your business intentionally and sustainably.
What Is Wandering Aimfully?
Wandering Aimfully is a membership program designed to help small business owners start, grow, and sustain their businesses in ways that align with their personal definition of “enough.” At its heart, WAIM is a combination of:
• Monthly Group Coaching: Live, values-driven calls that deliver practical, actionable advice on every aspect of running a business online.
• Educational Resources: A vast library of courses, templates, and tools that cover marketing, course creation, memberships, and more.
• Community Support: A robust Slack community where members freely share ideas, celebrate wins, and provide encouragement.
But what sets WAIM apart is its philosophy. Jason and Caroline encourage members to define and work toward their “enough number”—the financial and personal goals that feel right for you, instead of chasing endless growth just for the sake of it.
Key Features of Wandering Aimfully
1. Values-Driven Coaching
Every WAIM monthly coaching session begins with a review of Jason and Caroline’s values, which include transparency, creativity, and prioritizing what matters most. Unlike traditional business communities that push the “10x your revenue” mantra, WAIM’s coaching focuses on sustainable growth, intentional decision-making, and avoiding burnout.
2. Comprehensive Resources
WAIM offers a vast library of resources covering everything you need to know about:
• Creating and selling online courses
• Building memberships
• Marketing your business
• Managing time and productivity
• Pricing and financial planning
And it doesn’t stop at theory. These resources include actionable templates, spreadsheets, and real-world examples so you can hit the ground running.
3. A Thriving Community
WAIM’s Slack community is a treasure trove of support. Whether you need feedback on your latest project, advice on a tricky client situation, or just a cheer squad for hitting a big milestone, this is where you’ll find it. The community is generous, knowledgeable, and deeply aligned with the WAIM philosophy.
4. The WAIM Dashboard
The member dashboard is thoughtfully designed to help you navigate all the resources without feeling overwhelmed. With suggested paths based on your goals, you can find exactly what you need, whether you’re just starting out or refining an established business.
Pros and Cons of Wandering Aimfully
Pros
1. Values-Aligned Approach: WAIM‘s philosophy of defining and working toward “enough” is a breath of fresh air in a world obsessed with hustle culture.
2. Affordable and Accessible: At $100/month or $1,000/year, WAIM is incredibly affordable compared to most business coaching programs.
3. Incredible Value for Service-Based Businesses: If you’re building a service-based business, the resources and coaching cover every major challenge you’ll face.
4. Actionable Tools: From pricing calculators to course templates, WAIM gives you tools you can implement immediately.
5. Supportive Community: The Slack group is one of the most giving and helpful communities you’ll find online.
6. Fun and Informative Coaching: Jason and Caroline have a knack for turning coaching calls into engaging and enjoyable learning experiences.
Cons
1. DIY Approach: While WAIM offers everything you need, it requires self-discipline to dig into the resources and take action. There’s no hand-holding.
2. No 1:1 Coaching: WAIM is a group experience, so if you’re looking for personalized advice tailored to your unique challenges, it may not be the right fit.
3. Overwhelm for Beginners: The sheer number of resources can feel daunting if you’re brand-new to online business.
Who Is WAIM For?
WAIM is ideal for:
• Service-Based Business Owners: Coaches, consultants, designers, and other service providers will find the tools and strategies they need to grow sustainably.
• Course Creators & Membership Owners: If you’re building a course or membership, WAIM‘s resources are invaluable.
• Values-Aligned Entrepreneurs: People who are tired of hustle culture and want to build a business that aligns with their personal values.
• Self-Directed Learners: Entrepreneurs who are comfortable taking initiative and implementing strategies on their own.
Why I Recommend Wandering Aimfully
I joined WAIM in 2017 after Jason and Caroline sent an email about their concept of an “enough number.” That simple idea—determining how much money and success is enough for you—completely reframed the way I think about my business. Instead of chasing endless growth and falling victim to comparison, I started building my business intentionally and sustainably.
Over the years, WAIM has given me everything I needed to navigate the ups and downs of running a service-based business. The monthly coaching calls are equal parts informative and fun, and the community feels like a safe haven in an online world that can often feel superficial and salesy.
I’ve recommended WAIM to at least a half-dozen people who’ve all joined and loved it. It’s a fantastic option for small business owners who aren’t quite ready for my 1:1 coaching but still want values-aligned guidance to grow intentionally.
How WAIM Stands Out Among Online Business Communities
When comparing WAIM to other business memberships or small business online communities, it shines for a few key reasons:
• It’s Not a Cookie-Cutter Approach: WAIM helps you build a business that reflects your values, not someone else’s formula.
• No Upsells or Hidden Costs: Once you’re in, you have access to everything. There’s no “unlock premium” or upsell to worry about.
• It’s Built Around Fun: Business can be hard, but Jason and Caroline make learning enjoyable.
Final Thoughts: Should You Join WAIM?
If you’re an entrepreneur looking for an online business community that prioritizes values, sustainability, and joy, Wandering Aimfully is an excellent choice. It’s perfect for service-based business owners who want actionable strategies and a supportive network without the pressure to scale at all costs.
Whether you’re just starting out or looking to refine an existing business, WAIM offers tools, guidance, and community to help you grow in a way that feels right for you.
Ready to join? You can learn more and sign up at Wandering Aimfully. When you join through my link, know that I genuinely believe in this community—and I’m thrilled to share something that has been such a huge part of my business journey.
* This post contains affiliate links. If you join WAIM through my link, I’ll receive a small commission but the price you pay will not be affected. I only endorse products that I truly love and use, and this is no exception.