The Best and Worst Investments I've Made as an Educator & the ones I'll Always Make in 2026

Six years in. Full-time educator. Full-time marketer. And I have absolutely thrown money at things that didn't move the needle and at things that completely changed the trajectory of my business. I wanted to pull back the curtain on this one because I think we talk a lot about what to invest in, but not enough about why some investments land and others just... don't. And I have life financial goals and business financial goals, so at this point I'm very deliberate about where my money and energy go. What gives me the highest ROI? What takes things off my plate so I can actually show up and do the work that matters? That's what this episode and this post is all about.

What You'll Learn

Which investments genuinely moved the needle in my education business (and which ones I wouldn't touch again) Why peer-led masterminds didn't work for me and what to look for instead The software I use to run my entire online education business The 4 categories I will always invest in, no matter what stage of business I'm in When to invest in support and when it's too early

*This post may contain affiliate links, meaning that if you make a purchase after clicking one, I may receive a small commission at no extra cost to you. I only recommend products and tools that I personally use, love, and recommend.

What Were My Best Investments as an Online Educator?

Let's start with the wins.

A High-Ticket Launch Program (Together We Launch)

This was a significant investment, but it was 10 out of 10 worth it. The program walked a group cohort through launching in a very systematized, step-by-step way. And here's the thing launching is a skill. It's not something you just figure out. It's buyer psychology, communication, structure, all wrapped into one. I launched for the first time in 2020, very scrappy, get-it-out-there energy. It worked because I had already spent a lot of time building my audience. But I knew that if I wanted to scale beyond my existing community, I needed to actually learn how to launch. What I took from that program has since become the foundation of how I teach launching to educators now evolved, more flexible, but still grounded in structure. Because structure is there for a reason.

My First Coach (Before I'd Made a Single Dollar Online)

My first ever business investment was $5,000 in a mastermind before I had made a dollar online. And I will say it had immense ROI. She had built an online education business in the beauty space. She had done all the launching. She knew Kajabi. She could hype me up when mid-cart momentum dipped. And the biggest thing? I didn't have to spend hours Googling everything from scratch. Someone had been there and done it, and I could just ask. That's why I'll always offer one-on-one coaching. Yes, it's a bigger time commitment but the impact is so much more targeted.

A Social Media Management Certification

When I retired from doing hair and moved into the online space, I actually went through a full certification program with an experienced social media manager. I applied everything. I learned the fundamentals. I think this step gets skipped a lot now, and I think it's a real issue. People assume they can just ask AI and get the skills. But AI doesn't teach you problem solving. It doesn't teach you the foundational thinking you need to run a business for the long haul. For beauty educators and course creators especially the shortcuts AI offers can be great, but not at the expense of real skill development.

Kajabi (All-in-One Software)

In year two, I made the switch to Kajabi, and I haven't looked back. Before that I was cobbling things together Teachable, MailChimp, manual Zoom links, PDFs from Canva. It worked to get my first cohort off the ground, but it was eating up so much time that I couldn't actually focus on growing the business. Kajabi houses everything: sales pages, email marketing, course hosting, one-on-one coaching, invoicing, the student portal, all of it. And the portal experience for students is so much cleaner. They log in, everything is there, support is clear. That backend journey matters a lot when you're building an education business. (There are other options, Go High Level is popular with some educators I know but Kajabi is what I use and recommend.)

My Copywriting Mentor, Kaitlyn

As long as I'm in business and she's in business, Kaitlyn will be in my back pocket. Having an expert who can be a second set of eyes on my copy, my sales pages, my launch assets that's invaluable. The world's best authors have editors. And when you're working on your own stuff, you're just trying to get through it. Having someone who actually understands conversion copywriting look at your work? I've seen it make a real difference in my own launches and in my clients' results.

What Investments Didn't Work For Me?

A Peer-Led Mastermind

This one is recent, and I want to be careful here because I know people who got a lot out of it. But for me, it didn't work and I've had this experience more than once with peer-led formats. The design was centered on pods and community rather than expert-led direction. Random topics got submitted by the group each month. The main value proposition was community. Here's the thing: I love community. I genuinely benefit from it as a byproduct of any group container. But when I'm investing in something to grow my business, I want to cut through the noise, not wade deeper into it. Too many cooks in the kitchen. Unsolicited advice from people who don't know the nuances of your business. Things that don't go deep enough. Information is everywhere right now. When I invest in something, I want it to speed things up and give me clarity, not add more voices to the mix. If community is the main value proposition, that's a flag for me now.

Hiring an OBM From a "Save Me" Energy

I've made bad hiring decisions when I was overwhelmed and just wanted someone to swoop in and take things off my plate. That was the wrong approach and it led to unclear expectations, too much access given to people I couldn't fully trust, and outcomes that weren't what I needed. What I've learned: as a leader, it's my job to clearly define where I need support before I bring someone in. Hiring from desperation doesn't give you the time or clarity to do that well.

Paying to List Events to Broad Audiences

This one was fairly niche but worth mentioning paying for exposure to audiences that weren't my people just didn't translate into ROI. If I were going to spend that money on marketing, I'd put it into building my own audience through ads or content.

What Are the 4 Categories I'll Always Invest In?

These are the filters I run every investment through now. If it doesn't fit one of these four buckets, I think twice.

Expert Consulting

There is no replacement for someone who has done the thing, has helped other people do the thing, and can sit down with you and actually audit what's going on. One-on-one time with a true expert shortcuts so much and it protects you from spinning your wheels for months on problems someone else could help you solve in an hour.

Specific Skill Building

Launching is a skill. Branding is a skill. Content creation is a skill. Copywriting is a skill. When you invest in building a real skill, nobody can take that away from you. Right now I'm actually going back to learn Facebook and Instagram advertising again because it's changed significantly. Specific skill building is not a one-time thing. It evolves with your business. One of my students once said to me: "You don't just give us a fish. You teach us how to fish." That's always the goal because skills compound.

Support

There's a caveat here: don't hire too early. When you have more time than money, invest in consulting and skill building first. But once you're making money and time becomes the bottleneck? That's when support changes everything. I have team members in specific, clearly defined roles. I have expert retainers (like my bookkeeper) who are autonomous. Together, that structure gives me the capacity to grow and to actually show up for my clients and students the way I want to.

Experiences That Give ROI

Events, retreats, in-person photo shoots, content studios anything that gets you out of your day-to-day environment. There's something that happens when you're in person with people who are on a similar journey. You think bigger. You make real connections. You leave with assets, ideas, and momentum you couldn't have manufactured at your desk. I include brand shoots in this category too. Getting out of your normal environment does something for your mindset that's really hard to replicate any other way.

How to Apply This to Your Education Business

Early stage (more time than money): Prioritize expert consulting and specific skill building. One good mentor in your space can save you years of trial and error. Growth stage (making money, time is the bottleneck): Start investing in support but be intentional. Define the role clearly before you hire. Know exactly what you're delegating and why. At every stage: Run every investment through these four filters: Does this build a skill I'll have forever? Does this get me an expert's eyes on my business? Does this buy me time and capacity? Does this give me an experience that expands how I think? If the answer is yes to any of those it's probably worth considering. If the main value proposition is "community" or "exposure" with no clear ROI attached? Think twice.

Key Takeaways

‍Launching is a learnable skill and investing in learning it properly pays off every time you launch

Your first coach matters find someone who has done what you want to do in your specific industry

Don't skip the fundamentals AI can speed things up, but it doesn't build the problem-solving skills that sustain a business

Kajabi (or a solid all-in-one platform) is worth it once you're past the scrappy stage

Hire from clarity, not desperation; define the role before you bring someone in

Peer-led formats have limits community is great as a byproduct, not the main event

The 4 forever investments: expert consulting, specific skill building, support, and ROI-generating experiences

Ready to Build Your Education Business the Right Way?

If this post gave you an idea or a new perspective, send me a DM on Instagram  @itsJodiebrown. I'd love to hear your thoughts.

And if you’d like to listen in on the exact podcast episode that accompanies this blog post, you can do that here, or wherever you get your podcasts.

Xo Jodie

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