Sam Holstein

4 Big Ways I Messed Up My Blogging Career in the Last 12 Months

4 Big Ways I Messed Up My Blogging Career in the Last 12 Months

The past year has been a rough one for my writing career. I ended 2019 on a historic high, making $18,000 in two months and feeling like I’d finally “made it.” Then the pandemic hit, my Medium income cratered, and now I’m living off of food stamps and the continuing generosity of those around me.

I can sit here and complain about how the pandemic has affected my life or about how Medium corporate’s questionable business decisions have screwed creators like me, but the fact of the matter is, the position I am in is largely my fault. I made some bad business decisions and now I’m paying the price. 

I’d like to tell you about them so that you don’t make the same mistakes.

1. I should have built my WordPress blog and my Medium blog at the same time

For the last year and a half, my WordPress blog has been nothing more than a static page. The home page had a few words about me, some links to my Medium blog, my newsletter signup page, & my LinkedIn profile, but it didn’t host copies of my Medium posts or serve any business function.

This was a mistake.

When you post your articles on only Medium, you are giving Medium the SEO credit for your stories.

When you post your articles on your own blog, then post them on Medium, and then use a canonical link to credit your own blog, you get all the benefits of Medium traffic but the SEO credit goes to your own blog

This is important for building a long-term strategy outside of Medium. When your personal website SEO is weak, you’re relying on Medium and only Medium for traffic — which means as Medium continues to cycle through this painful up-and-down experience, your results are along for the ride. 

When your personal blog’s SEO is strong, you are always building credibility on Google. Eventually, that pays off — your personal website’s traffic will be stable and/or grow even when Medium is not producing results.

Recently, one of the Medium writers I admire told me that thanks to their efforts with canonical links, they are experiencing more newsletter signups from Google than they are from Medium for the first time.

I have been writing on Medium for a few years and have had some whopper viral hits. I could be experiencing that too. But I’m not, because I didn’t bother. Stupid.

Make a personal website. Post a copy of every Medium story you publish to your personal website. Set a canonical link for your Medium story. It’s extra effort, but it’s worth it.

2. I should have sold courses

For years, I had a complex about selling online courses. I had a couple of issues around the whole thing:

  1. To me, a writer was a writer, not a course creator. A course creator is a teacher. Leaving writing behind in favor of creating a course felt like abandoning my original mission.
  2. I don’t like buying online courses. They’re expensive as heck, I’m poor, and the one time I did shell out for a course it ended up being a huge disappointment. Whenever I need to learn something, I make heavy use of my local library. I didn’t want to sell a product I never buy.
  3. One of the themes of my writing is frugality. It seemed like the height of hypocrisy to advocate frugality for my readers only to turn around and try to sell them some expensive information product when I know from experience the information can be had elsewhere for free.

I’ve been struggling with this tension for the past year and a half. I even launched a course about making money on Medium and got several sales, only to suffer a fit of regret later. I pulled it off the market within a month and refunded all the buyers.

But after a year of reflection, I’ve realized a few things.

  1. Unfortunately, personal bloggers just can’t make a living wage without high-profit-margin products like courses, coaching, and consulting services. I’m barely scraping by, and I’m tired of being poor. If I want to keep being a blogger (and I do, I really, really do), I will need to find a way to raise my profit margins, and the only way to do that is to offer an expensive product. 
  2. It’s not immoral to offer an expensive product if I preach frugality — I just need to make sure it’s an excellent product that’s worth the money for the people who decide to buy. Frugality isn’t about never spending money ever, it’s about spending money on things that are worth it, and I like to think buying a course from me about personal growth would be a lot more worth it than many of the silly things people spend money on.
  3. It’s not my decision how people use their money. If I offer a product and they choose to buy it, that’s their choice. In fact, if I’m honest and upfront about what my product is and they choose to buy it, I’ve done a good thing in the world — they wouldn’t have had access to a course they enjoy without me offering it for sale. 
  4. I’m not Jeff Bezos. I’m not accumulating billions of dollars of profit at the expense of exploited workers and devastated economies. I’m just a blogger. 
  5. I am an expert. I’m an expert in making money on Medium for sure. I’m also kind of an expert on personal development (if there is such a thing). I’ve read every bestseller and tried every productivity tactic on the face of this earth. I’m certainly an expert in how to make personal development advice work for mentally ill, neurodivergent, and chronically ill people. That knowledge took the better part of a decade to build. When you look at it that way, being able to buy it for $199 a course is kind of a bargain.

Last but not least, nonfiction writers are teachers. We’ve chosen to use words to do our teaching, but we’re still generally teaching things. People don’t read my articles for amusement, or entertainment, or escapism, they read my articles because they want to learn something that will make their life better.

In general, I think being too hung up on writing hurts a lot of nonfiction writers. We may be the people who grew up enchanted with the power and accessibility of books, but books have their downsides, and there are many people out there who aren’t in a position to benefit from books. There are other ways to change the world.

3. I should have created only one or two lead magnets

List growth is critical for bloggers. Our newsletter lists are our primary asset. They are invaluable. You can’t buy them, you can’t steal them, and you can’t hack them. The only way to have one is to build it yourself.¹ 

The best way to grow lists is with lead magnets. People want to download the shiny useful thing, they give you their email, they end up liking your emails, bingo bango. A lot quicker than waiting for someone to decide “Hey, I should sign up for this person’s list!”

I took it a little too far. Instead of just creating one lead magnet for all my articles like Anthony Moore, I created a new lead magnet for each type of article I write, and a general invitation for my newsletter for articles that don’t fit with any of the lead magnets.

Photo courtesy of author

My newsletter in general has great stats. As of this writing, my open rate for 2825 subscribers is 48.1%. (For context, the average open rate is 17%. I’m doing fantastic.) Maybe having many hyper-specific lead magnets helped with my conversion rates, but generally, they were just a distraction.

See, any time I created a lead magnet, I felt incredibly productive that week. As sign-ups for my new lead magnets came in, I congratulated myself on doing something good to grow my list. But list growth was never the issue. I already have a good-sized, engaged list. What I didn’t have was a solid blog (see problem #1) or any truly profitable products (see #2) to sell to these engaged list members. Which is a damn shame, because many of them have emailed me to tell me they would buy a course from me if only I would sell them one. ?

I should have not spent so much time creating different lead magnets. I should have created one or two all-purpose lead magnets, and then focused my time on creating actual products that could put actual money in my pocket.

4. I should have focused on creating fewer, higher-quality stories

As I became more despondent about my falling income and more torn about offering high-dollar-value products, I unintentionally hopped on what I’ve come to know as the content treadmill.

The content treadmill is what happens when a professional writer writes each article with only the next paycheck in mind. Instead of working strategically to build my website’s Google ranking and to build a body of content that would continue to support my work for years to come, I just produced essentially random articles as fast as I could. Some were great hits, but some were total losers. 

I think this strategy is great for people in their first year or two of blogging. It’s hard to know what interests you when you are just beginning, so blogging about whatever the heck you feel like is a great way to get a feel for what you enjoy writing and what readers want from you.

But I’m not in my first year or two of blogging. Continuing to strike out at random is no longer part of my beautiful growing process, it’s just a sign of entrepreneurial immaturity.

Specifically, it’s a sign that I’ve failed to build a viable business (so far). If I had more passive income — which I absolutely should, given the size and health of my email list — I would be able to focus on producing longer, more focused, higher quality content. But because I’m on the content treadmill, I need to keep printing out content at unsustainable speeds until I get that passive income built.


These are not little mistakes I’ve made. They’ve crippled me enough that I’ve thought more than once over the past few months about giving up my blogging business and just taking a regular job. But I’m not ready to give up, for 2 big reasons:

  1. Building a lifestyle business has always been my dream. I’m still chronically ill and it’s still difficult for me to hold down a full-time job, and I don’t see that changing anytime soon. It would be nearly impossible for me to run this side hustle and work a traditional job. Also, I want a lifestyle business for all the normal reasons people want one, like travelling and pursuing my own interests and that sort of thing.
  2. If I take a normal job, I lose my Medicaid, and I am hugely dependent on my Medicaid. With Medicaid, my copays are $0 on everything — but if I take a normal job, I would have my employer’s insurance (or heaven forbid, the hilariously expensive plans) and I’d immediately start having to pay hundreds of dollars in copays a month, making getting a traditional job pointless in the first place.

Obviously, if I manage to build my business, my income will rise and I’ll lose my Medicaid anyway. But it will be easier to stomach having to pay for health insurance out-of-pocket when the money is coming from my blogging business, my dream come true. If I give up on my dream, take a traditional job, and then have to fork over a large amount of the money to medical providers anwyay, then giving up on my dream will have been pointless.

(For most people, I wouldn’t recommend what I’m doing. If you’re generally healthy and aren’t dependent on Medicaid, stay at your traditional job until your side hustle brings in enough money to replace your traditional job.)

But you don’t have to go through the same journey. You can avoid the same mistakes.

  1. You can set up your personal website and take advantage of canonical links now, so that when one of your stories gets 100k views, all that sweet sweet Google credibility goes to you instead of Medium. (It happens more often than you think. I have eight stories with over 100k, one with over 300k — and all that SEO value is lost to me now).
  2. You can start thinking about your business model now. Instead of feeling bad for monetizing your blog, you can pick one kind of profitable information product, make it the best it can be, and sell it to a happy and excited audience.
  3. You can focus on marketing that works. Instead of casting about with a bunch of silly stuff, you can focus on making one or two great lead magnets that provide a lot of value.
  4. You can write focused articles. Instead of writing about whatever silly thoughts cross your head that day, you can ask yourself hard questions about whether what you have to say is thoughtful and valuable.

Of course, you’ll make some mistakes of your own. But maybe they can be the fun kind, like messing up how you scale your rapidly growing blogging business, or messing up how you invest or donate your gobs and gobs of profits. 

I hope that here in the next few years, I’ll have the chance to make those kinds of mistakes.