I created a tiny online space called “The Side Blogger,” where I help fellow tiny online space creators, such as bloggers and newsletter owners, make big money with small audiences.
I’ve owned my space for a little over seven years, and I’ve made a full-time living with it (six-figure yearly revenue) for about five of those years, selling online courses, workshops, affiliate offers, and templates.
And then, just a little over a year ago, I decided to make a big change.
Instead of offering a one-time buying option, I bundled all of my educational content and made it available inside a member-only website for a monthly or yearly subscription.
In theory, it made perfect sense.
Get everything a creator needs to know for an affordable monthly ($27) or yearly ($189) fee, instead of having to buy one course at a time for anywhere from $99 to $499….Who wouldn’t want this killer deal?
Reality though?
It bites!
My calculations (despite a Bachelor of Science degree in Electrical Engineering) were completely and embarrassingly off! Instead of having 500 members after one year, which was my initial goal, I don’t even have 100.
And yet, here I am, talking about my membership because while it isn’t a raging success yet, it has shown the promise to be one in the future.
This post is for the aspiring or budding membership creators, so that:
- You understand what to expect from memberships
- You do not make the same mistakes I made
Lesson 1: Research Before You Start
I’m the queen of knee-jerkiness. Maybe it’s ADHD, maybe it’s that and more. But here’s how I work: I wake up with an idea. And I execute.
Because of this, I made beyond rookie mistakes when I launched the membership. You’ll know what I’m talking about in lesson #2, but for now, let’s just say that you should really look at how successful memberships work before you launch your own.

Maybe join a membership program yourself. Not a struggling one, but one that’s been around a while and thriving. Observe what you like and what you don’t like. Pay attention to what makes you come back to a membership and keep paying for it.
Those are the things you’ll want to implement in your own membership.
Lesson 2: Static Content Doesn’t Bring Continuous Payments
My second lesson came as a rather harsh wake-up call.
My initial goal for the membership (beyond a predictable income for myself) was to create a space for my people to get all of my courses in one place, without having to pay for them individually.
It seemed like a smart idea at the time, but in hindsight (it’s a bitch, I know), I should have known that people do not pay you over and over for static content.
The courses attracted a lot of people in the beginning, but almost all of them canceled their membership after a couple of months. They simply had no reason to stay and keep paying after they learned everything there was to learn.
So, takeaway: You need to give your members reasons to keep paying you. It may be a community, regular new content, ongoing coaching, or a combination of these.
In my case, I’ve added a community for ongoing Q&A and monthly workshops. I’m still experimenting, but they seem to be attracting the right people, for now.
Lesson 3: New Members Must Not Create New Work For You
After the wake-up call about static content, the first continuous offer I created for my members was a custom, 1-on-1 business review/plan for each new member. Which I quickly scrapped because it wasn’t sustainable.
During a promo, I got a bunch of new members, and the regrets couldn’t come faster.
Suddenly, I had no time for anything else, and most of these members, once they got their content evaluated and a solid plan for how to move forward, canceled their membership.
In retrospect, this is not a bad idea. Many business owners offer this type of service to their members, but you have to be careful and smart about its execution. Which brings me to:
Lesson 4: Cover Your Bottom Line
My goal was to make the membership affordable. But in doing so, every custom offer I added, including the content evaluation and business plan, backfired.
There are a couple of ways to rectify that:
Create a more expensive tier that attracts people who already have the money and are not itching to cancel their membership as soon as they get some value.
Or, offer only yearly memberships so you get a good chunk of money upfront.
Maybe both!
For example, one membership creator, Travis Sago, offers his membership for $299 per month, or $1,999 per year. He only has 527 paid members. You do the math.
In my case, I did create a more expensive tier, but even at $75/month, it wasn’t worth it. So, I took away those custom offers (and sunset that tier) entirely.
The monthly workshops that I offer, on the other hand, are much more sustainable because they do not add more work for me, regardless of how many members I have.
Do not expire your existing, working system until your membership is a success. Or chances are that you’ll come to regret it.
Lesson 5: Clarity Creates Continuity
This is something I’m still struggling with: Clarity.
At first, my goal was to offer a course bundle. That was clear enough: “Become a member, and get X, Y, and Z courses.”
But since that wasn’t enough to keep members, I added more to it, and the whole thing became…confusing. Even to me!
Do I focus on my courses? My monthly workshops? The community where I answer my members’ questions daily?
And if the seller is confused about what they’re selling, you can understand how confusing it is to the buyers.
My current solution to this problem: promote only one thing at a time.
Some days I’ll promote one of the courses…like the List-Building course or the SEO course.
Right around the monthly workshops, I’ll promote only that workshop.
If I publish a case study, I’ll promote the case study.
It works, kind of.
But I feel like there should be a better way to consolidate all that. What that is, I don’t know. Not yet. But I’m working on it.
What I do know is this: My own confusion prevents me from getting new members to my program. And until I have solved that problem, my membership will continue to struggle.
Takeaway for you? Be clear about what exactly you’re offering. It may take you some time. You may have to experiment with different angles. But keep testing until you know what resonates with your audience.
Lesson 6: Have a Safety Net
When I launched the membership, I was so stupidly arrogant that I stopped selling all of my courses and templates and focused all of my attention on promoting the membership.
It was the 9-5 equivalent of quit before you build.
And the price of that oversight was hefty!
Now I have a better system. I continue to sell my courses and offers, while promoting the membership as a catch-all bundle.
This way, people can choose which version they want. And I’m financially more secure.
So, my advice to you is this: Do not expire your existing, working system until your membership is a success. Or chances are that you’ll come to regret it.
Well, that’s where I’m at.
I started the post by saying that my membership has shown promise.
And it has.
A few weeks ago, I needed cash, so I offered a limited-time lifetime upgrade to members for $500.
At the end of the promotion, I ended up with 32 lifetime members out of 43 total members, each of whom paid anywhere from a hundred or so to 300+ after proration.
This tells me that those who have been members for a while do see the benefit of being a member, enough to upgrade to the lifetime tier.
And that’s my sign that the membership has a future.
One of my favorite creators and membership owners, Sean D’Souza, who created his membership a couple of decades ago, said that it took him a couple of years to figure out how to make the membership profitable.
He also said that one of the definitive things you can do to make your membership a success is to… simply keep it going.
So, that’s where I’m at.
I’m going to continue with the membership because I want it to be a success. I want to be the go-to for others who want to make their membership a success. I want Membership-Whiz in my entrepreneur resume.
And for that alone, I’ll continue offering my membership.
Want more great stuff like this?
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