15 Years Failing at Blogging: Hard Lessons Learned (That Could Benefit You)

I’ve been blogging now, on and off, since 19 years old. Or should I say, failing at blogging since then.

In that time I’ve seen a lot of stuff. Thought about a lot of stuff too. This medium, for some reason, keeps on coming back to me. 

Unlike most posts you’ll read on the topic though this isn’t one of chest-thumping success. My story? Not the type that gets you pumped into thinking you’re gonna be a filthy millionaire overnight. Instead it’s more modest than that. Fifteen years of failed blogging? Not exactly. There’s been a few successes along the way.

What I hope you can see here though are parts of your average bloggers story. Not the outliers you see on social media. Nor those trying to fake success to get you in a sales funnel. While that stuff has its place – and I congratulate them for being good marketers – it doesn’t really sell you on what this game is actually all about. 

For those of you interested in blogging (or writing, more broadly), and want a different perspective, maybe this one’s for you. Everything I learned in that time trying to find, keep and captivate an audience? I’ve tried to share here. Some things obvious. Some things maybe not.


Before I get to the lessons; here’s a disclaimer. Yes, I’ve made a bit of money from blogging in the past. But instead of making money from writing and digital products – which is how I believe it should be done – it was mainly from selling links for search engine optimization (SEO) purposes. To people who might not understand any of that; here’s how it works. Companies pay you to put a link on their website so you help them show up on the first page of Google. This is called “link-building”. 

So, I guess my failed credentials are still kind of intact?

#1: Talking About Yourself (Too Much)


About five minutes ago I was writing a different article about something else. It was all about this other website I have; a site where I’m able to write much easier and faster because it’s disconnected from me. Then (because writing is hard) I came back to this article realising I could probably say it here better.

So yeah, lesson number one comes from the mistake of blogging about yourself (too much). That’s the primary reason I’ve struggled writing consistently at this site. Because being personal is difficult. And oftentimes you’ll run into trouble emotionally when everything centres on you. 

Of course there are lots of people that do an excellent job of this. The ones that do though generally weave their personal stuff into some greater philosophical point. Or have lots of actionable suggestions. It’s very rare to see a successful blogger who’s best content reads like a string of greatest biographical hits. But I know a few.

Another useful tip to stop you failing at blogging; it’s way easier to write at a site where the domain isn’t your name. The disconnect, particularly if you’re overly analytical like me, can really help free you up. Help you execute ideas or experiment with them with less fear. 

Extra tip: Sarah Aboulhosn details this dilemma of dealing with a self-named domain blog really well. Check out her excellent article “What all of my failed blogs have taught me” for extra advice.

#2: Not Having an Angle/Hook

Possibly the two best blogs I ever had; both in terms of audience and satisfaction, were MySpanishAdventure.com (MSA) and TravelSexLife.com (TSL). The things these both had in common? A specific topic. 

And yeah, while both ultimately failed (more on this later), the one thing that did work really well was the content itself. I generally always knew what to write. Or who to get to write it. 

Right now I’m spending a lot of time reading about affiliate marketing. This is something I’ve been involved in before but it’s also something I still find interesting. One thing I think would improve lots of dull sites I see? More time spent focusing on a hook. 

Sean Ogle, one of the first people who helped me with working online (definitely follow him if you’re interested in this stuff), does this really well. His sites, BreakingEighty.com and SlightlyPretentious.com, stand out from the others (and probably build more trust and hits) because he actively works in a narrative to go along with the subject. Travelling to 100 of the world’s best bars etc.

One possible pitfall – as I found with MSA – is the danger of going too specific. That site was all about my journey to Spanish fluency. And because I was actively working on that goal, had a time limit. Tight boundaries like that can often derail a blog project. Unless you’re creative enough to figure out where next to spin it (I wasn’t back then). 

#3: Don’t Get Freaked Out

You’ll probably start off blogging with big aspirations. Growing a platform fast is the usual aim, and generally you’ll risk a lot to get there.

Case in point: growing the small audience I had at MSA, feeling a sense of debt to them and then forcing myself to churn out a lot of low-quality content. Mainly because I was scared to lose them.

Managing an audience then, no matter how small, is a very tricky thing. They’re the people who make or break you as a writer and have the power to help you grow. That’s why they should be first in your mind when you set out to write an article. But not too much so that you feel pressured and get freaked out.

This is why, looking back, I advocate not interacting with your readers too much. Get a sense of what they’re interested in, sure. But don’t feel the need to address absolutely everything that’s getting asked. Otherwise you’ll get really bogged down in trivial stuff that works for one but not for the crowd.

Last tip (and one I don’t see many others recommending): gratitude. Treat every single person reading your stuff as a potential lifelong friend. I didn’t do this with most of my blogs looking back and now I really regret it.

#4: Consistency

I’ve written about the power of consistency before. It’s been the number one thing I’ve struggled with most in my life. It’s also the thing that’s killed every blog I’ve ever started.

A few things not blogging (publicly) for a couple of years will tell you; momentum is everything, habit is key and detachment to the outcome is critical. Become consistent by assuming you will fail. Then just do it anyway.

One of my favourite subreddits at the moment is r/juststart. It’s another community about affiliate marketing that deviates into blogging. Their basic ethos? Just f*cking start. Get the ball rolling. Post consistently for six months and don’t expect any kind of result. I dig that message.

Another big regret? Selling or letting go of old blogs for lack of updates. The content sitting there alone (most of it “evergreen”) was valuable enough in itself. For example, I remember writing very lengthy articles on the camino and my silent mediation experiences – since now disappeared – that would probably do well in search and still help a bunch of people today.

So resist the urge to delete or remove your stuff. Even if it’s been years since you last wrote. You never know when you’ll pick it back up again. Or just how valuable (even if only to a single person) that old content might be.

#5: Keep Your Day Job (Or Another Creative Outlet)

Neil Patel (huge name in blogs and SEO) says the difference between a failed and successful blog comes down to the notion of seriousness. Making it work, he argues, depends entirely on shifting gears. And learning to treat your blog as a business.

I don’t think that always works. At least in my case it hasn’t. My early days working on content (full-time) at gap year start-up GapDaemon.com gave me huge leverage in getting MSA off the ground. Knowing I had the money to fall back on (they let me work remote), took the pressure off as I built out that blog in the early days. Enabling me to experiment more, and help me find a voice.

Without that level of support, a regular pay-check etc, I think failing at blogging (in the beginning at least) can be almost natural. In some ways, having something else to do in life, other than writing, can help give you the mental space to make your content better (I’m also finding this more now – given my main focus is on studying medicine).

Taking the leap from amateur to professional blogger too, for me at least, was rough. I got sidelined by the industry. Networked too much with people doing the same thing. Ultimately ran out of ideas and inspiration.

If you can avoid that, stay sidetracked by some other hobby or job, I think blogging (or creating in general) can be a lot easier.

#6: Keep it Simple

The main reason why TSA, my website about global sex culture, failed? Became too complicated. 

In the beginning it started as a simple idea. I thought it would be interesting to profile backpackers (and other travelers) sexual experiences or impressions of other countries’ sex culture. Not in a pervy or misogynistic way (like most of the internet does), but in an open format. Filled with women’s voices just as much as men’s.

Where it all went wrong – despite the web traffic being insane – was that it became a group project. I gave the concept away to work with two friends of mine (Stephen, now a successful New York advertising guy) and Michael. And because more voices were now involved it became impossible to implement my original vision. 

Everything we wanted to get done? Had to go through the three of us. Hence us having many long and unnecessary meetings about things that could have just been tried on the spot. Because of that, I just lost interest in the idea. Became unmotivated to work on it.

Don’t get me wrong, without those guys the site wouldn’t have been as great as it was (at least in my eyes). Both brought so much to the table. And things I couldn’t have possibly done on my own. But, at the end of the day, it’s easier to keep things simple. Execute your own idea first before bringing others in to help. 

Side note: it’s also hard to make money with a blog related to sex. Advertisers just shy away from it on impulse, despite your best intentions. Nat Eliason mentions this too, although he found an interesting way to do it regardless.

#7: Remember Your Reason Why

It’s easy to get carried away with blogging. I guess the same could be said for art in general. You find success with one thing – and then you do everything in your power to replicate that thing. Over and over again.

Doing that however is a surefire way to monotony. Both for you and any potential audience. That’s why it’s best to stay grounded if possible. Come back to the original reasons you started creating in the first place. And forget about all the other stuff that happens afterwards.

For me, at least, that’s the place I feel most comfortable and productive making things. When I simply feel like answering a question in my head. Or addressing an email I’ve got as a broader article. Not trying to reinvent the wheel or force things too much.

You might also find that you’re the type of person that money can corrupt too. I don’t mean in the evil sense. Rather in the purity of your art-style sense. Where you get financially rewarded for something you don’t think necessarily reflects your true voice (or true philosophy) but you capitalize on it anyway. Because you can’t see any other way of succeeding (financially at least) at the time.

This is another reason why I think many bloggers have been able to pass me by these past years. They’re not as emotionally invested in what they do. Maybe doing it solely for the money rather than because of a need or want to simply say something. There’s nothing intrinsically wrong with that. That’s just not me. So be careful in considering where you fall on that spectrum.

Failing at Blogging: Final Thoughts

I’ve been wanting to write an article like this for quite while. I’ve spent a long time thinking about the platform – more than’s probably healthy – and still find myself coming back to it. I just love words. Learning about people. And all their interesting ideas. 

But I also want to sell the message that it can be exceptionally difficult. And not as easy as these “how to blog” articles (although they do give a lot of great practical advice) suggest.

Sharing my personal story failing at blogging over the last fifteen years? Hopefully can help show some of that.