March 15


How to Turn Your Blog Into a Second Income

Have you been blogging for a while?

Would you like to see better results from the work you put in?

(this post contains affiliate links.)

I’m going to describe a set of professional tools that will help you reach more readers, build a regular audience, and earn money from your work.

A Guide to the Technology that Runs this Blog.

Now, this is a post with a particular reader in mind.

I’m going to assume that 1) you know what blogs are, and 2) that you have something great to share with the world, and 3) that you like the idea of writing about it regularly.

I know that this doesn’t describe everyone. I definitely want to talk, in a later post, about finding one’s voice and choosing what to write about.

This particular post, however, has an ideal reader: you have some experience of writing online.

Maybe you have a blog on or Squarespace, and you wish you had more time to write for it.

You’ve tried to publish online in the past, but it hasn’t worked out quite as well as you hoped.

Here’s a four-part plan for changing that.

The Research Stage

These recommendations are the results of a great deal of research.

I’ve listened to hours and hours of podcasts, read books, joined email newsletters, and even paid for a couple of training courses.

I’m going to describe the tools and technologies that power this blog, and which you can use to make your own blog the best it can be.

We’re going to talk about email mailing lists, social media planning, and earning an income from affiliate links.

And, to frame how these tools are supposed to work together, I’m going to describe a problem or difficulty that blogs have, and then describe how you might overcome that problem with a small, focused suite of apps and services.

Now, I feel like you might be thinking — shouldn’t a blog just be about writing? Why do you need to worry about spreading the word, building a community, and so on?

Isn’t it purer, more appealing, to just keep writing, and attract interest that way?

Well, maybe you don’t feel this worry. But I know I do!

I look around at the Internet, and I see writers I really admire. Matthew Yglesias and Osita Nwanevu, Mallory Ortberg and Sarah Jeong.

A voice inside me whispers: these people just write. They just create.

Not really…

It’s somehow hard to remember that, while these people are indeed phenomenal writers, they also work for publications with a marketing team and a detailed social media strategy.

One suspects that Matthew Yglesias would be a successful essayist anywhere, with any set of tools, because he is brilliant — and yet it is also the case that, where he writes, was built around a plan to build enormous traffic out of Facebook, a plan that the company’s technology team seems to have executed with great success.

You need your own technology team.

This post will help you adopt methods and tools that will allow a one-person blog to offer more valuable posts to readers.

The Trouble with Blogs

Blogs have a lot of great advantages.

The trouble, however, is this.

  1. You aren’t a destination.
  2. The majority of visitors will never come back.
  3. It’s hard to deepen the relationship with your most committed readers.
  4. You aren’t making any money.

Now, I’d like to explain these four problems in detail, but before I do, I feel slightly uncomfortable about something.

I feel — I feel awkward.

This post is hard for me to write because it feels like a criticism of my old blog. That’s not my intention at all.

And yet the feeling persists.

Let me explain.

Imagine you are at a party, and it’s full of cool strangers.

These are people you would like to impress. They are all high-level players in your field, your discipline, your world.

Where is this party? It’s in a grand old house, somewhere high on a hill. The night wind is wild outside. You were invited by a friend, but unexpectedly, he didn’t show up.

You sit alone through dinner, tasting each delicious dish in silence.

Grand dinner party
It’s a strange party

You now feel like it was a mistake to come. Yes, you want to impress these people — it’s a great opportunity — but you are feeling so uncomfortable and awkward.

“Who is that mousy, dull nobody?” they must be thinking.

The meal ends, at last. Everyone retires to a deep, dark lounge. The huge fireplace smolders. Candles flicker in the corner.

You accept a glass of scotch.

Suddenly, unexpectedly, you are asked a question. You discover that someone here knows an ex-colleague of yours.

You answer the question, and this stranger seems pleased with your response.

And, to your surprise, the rest of the room listens in, going quiet.

She asks, “Do you know the story of how Sue lost her job? I’ve heard it was quite a tale, but –”

The thing is, you do know the story. And it is quite a tale.

Only — you are still friends with Sue, sort of. And she would hate it if you repeated the story here, with these famous, successful people.

You quickly explain a summary version.

You think you’ve done your part, but even through you omit all the juicy stuff, your outline still makes the other people in the room laugh out loud.

They are staring at you, ready to hear more.

Somehow, you find yourself telling the entire scandalous story.

The Story of Sue

They love it. Their grand faces chuckle at your jokes; they lean forward. Slowly you develop the tale, recounting one embarrassing situation after another. A typo-filled email; an unexpectedly public toilet in Beijing.

Soon you are standing on one of the leather armchairs, hunched over, imitating your friend. The men and women of the party are howling, weeping in laughter.

You put on your friend’s voice, her irritating shiver, her pinched, anxious unease. You exaggerate how annoying she is; you expand on all her worst features.

One famous politician is wiping his eyes from chuckling, watching you in admiration. They love you.

You prepare for the final punch line. Sue’s final moment. The end of her career.

Your listeners are ready. They are in the palm of your hand.

And then — then you get a weird feeling.

You look round — you look at the darkened corner of that room — by the dying fireplace — and you see — you see — in the corner of the room — lit by candles — someone is there.

Someone is sitting in the corner.

It’s Sue.

No! Impossible!

Sue is watching you. She is devastated.

She is sitting hunched over, legs drawn up, arms protectively crossed. She is pale with shame, shaking with betrayal.

She had been there the whole time. How could you have not seen her?

You blink, rub your eyes. Sue is gone. There is no one in the chair. It was a moment’s halluncination. The chair is empty. Sue was never there.

You turn back to your audience. The crowd urges you to continue. Finish the story, they cry.

They are wild for the final line, the concluding laugh.

But you now feel ashamed, awkward. You struggle to remember what you planned to say.

— well, that’s kind of how I feel, right now, explaining my decision to re-launch this site.

I do want to tell you everything.

And yet I worry that by talking about all this new stuff, it will seem like I am complaining about the blog I had.

I worry it will seem like I am complaining about my very lucky situation from before, as if it wasn’t good enough for me.

This is definitely not how I feel. I am very proud to have a readership, especially the people who come back again and again to comment, share my posts, and contribute to my Patreon. I am grateful.

In the grand scheme of blogging, I was successful.

I had regular conversations with readers. Teachers adopted ideas from my posts into their syllabi. Academics quoted my writing (not always positively). People emailed me month after month, saying I inspired them.

My readers even supported me financially, through my Patreon.

And yet I still had these four problems.

Here they are, in a list:
1. Everyone spends most of their time on fb.
2. Most new people who visit your site never come back.
3. It’s hard to provide extra value for your most committed readers.
4. You aren’t making any money.

Four troubles with my blog

A graphic about the four problems

To explain how these problems work together: firstly, your potential readers are not surfing the web looking for interesting blogs to fall in love with. They are hanging out on Facebook, or Pinterest, or (maybe) Twitter / Linkedin.

So you have to struggle to get their attention and get them to click a link.

Secondly, most sites have a very high “bounce” rate. When you do get new readers, most of them appear, read one post, and leave, never to return.

Rather than stick around, they “bounce.”

(As an example: my posts have repeatedly been awarded a “Freshly Pressed” promotion from WordPress. Each time I received this honour, thousands of new visitors rushed over to visit. Amazing. And yet a day or two later, the blog’s traffic numbers returned to normal. The new readers checked out the site, commented, and departed.)

Thirdly — for the readers who do love your writing — it’s hard to reach out to them and offer them something extra. It’s hard to deepen that relationship or create something particularly useful for them.

Often, you don’t even know who they are. If they comment, you might have a name and an email address. But you don’t have an easy way to stay in touch.

Fourthly, a blog is free to read, and so it’s hard to make money from its (modest) success. And while this problem is perhaps not a big deal — many people write for free and are happy about it — over time, it eventually makes all the other problems worse.

The lack of an income drags down all the other aspects of your blog, because your time to write is necessarily limited.

Money Makes Everything Easier, Obviously

You could spend lots of time marketing your posts on Facebook. You could spend more time researching and planning great blog posts so that readers are more likely to stick around. You could create a cool Facebook group or Slack channel to build a community. You could devise intricate ways to advertise or build your Patreon.

But all of those things take time. And you need to be earning a living, and eating, and sleeping. Eventually, the lack of an income from the blog makes all the other problems worse.

Therefore, to run a more successful blog, I would need, somehow, to solve all four problems at once.

In other words: to be a successful blogger, you need to be able to market your work on social media, “hold on to” the casual readers who are visiting for the first time, offer extra cool stuff to your regulars, and earn some kind of money in the process, too.

If this can be achieved, then you will enter a virtuous circle: you boost the blog’s quality a bit, and please existing regulars a bit more, and gain more visitors, and earn some extra money: then, that money you earned would allow you to devote more time to boosting the blog’s quality, to building more cool stuff for your readers, which would then… etc.

However, until about six months ago, I was pretty sure that such a solution did not exist.

I knew what the problem was. But I figured there was no way forward.

A New Hope

Over the summer of 2016, however, my wife started researching how she might re-launch her food blog. She joined a great community of bloggers, Food Blogger Pro, a paid membership site, and she began forwarding me links.

We were both skeptically curious.

For Jeni, the most compelling factor was the income reports that successful bloggers posted. And these are inspiring documents. By reading the monthly reports of a blogger like Suzi Whitford, one could see a person build up a full-time income over the course of a year. This seemed like evidence that it could work.

But for me, those income reports weren’t so remarkable. After all, John Gruber makes a lot of money through Daring Fireball, but this is no guarantee that I would.

In contrast, for me, the really inspiring thing was learning about the blogging tools that had been at my disposal all along.

I began to see that there were some really remarkable tools available to “professional” bloggers that would solve my problems. If I could find the time to learn how to use this technology, and if my wife and I could afford the early cost of setting everything up, my blogging life could be transformed.

So around Christmas, I essentially shut down my old blog, and warned my readers that there would be only a few new posts for a couple of months. I read books. I listened to podcasts. I took courses.

And I developed a plan for re-launching my site.

Now, before I present the plan, and share the tools I’m using to level-up my blogging adventure, I do want to be clear: there are some costs involved. It requires a bit of financial investment. An outlay of sixty US dollars a month seems realistic at the start.

And while it’s possible to do some of these things more cheaply, or free, this will either make things a lot more complicated, or will require a lot of extra time.

So. Here’s what I am planning to do.

Solving the Four Problems

Just to recap — here are the four problems:

Problem 1: Reach (finding readers)
Problem 2: Bounce rates (keeping visitors)
Problem 3: Value (serving regulars)
Problem 4: Money (earning a living)

And remember: none of these problems are about writing. You could be a fascinating blogger, and a great teacher, and these problems would still exist.

Here are my solutions:

Solution 1: automate social promotion on Pinterest and (later) FB.
Solution 2: email opt-ins and mailing lists.
Solution 3: ConvertKit courses and FB groups.
Solution 4: affiliate marketing, consulting, and courses.

The first problem is: how to reach people on social media?

The goal here is to reach a large number of potential readers of your site, and attract them to pay you a visit. At this stage, you’re just trying to earn their visit. Because unless they find you, your cool essay on sentence-construction might as well not exist.

After looking through a great many professional blogs, it seems to me that there is one clear best practice for getting more traffic to one’s site.

What does “best practice” mean? It means an approach to social media promotion that is cheap to deploy, that is not scammy or disgusting, that can be planned out and automated with software, and that is not emotionally overwhelming.

The best three that I have heard about are: creating a (free) group on Facebook, paying for ads on Facebook, and automating a posting schedule on Pinterest.

And, given the criteria I outlined above, regularly posting on Pinterest appears to be the best option.

As a result, for the next few months, I am going focus on Pinterest almost exclusively.

Why Pinterest?

Well, I find Twitter very hard to be heard in. If you are not a natural tweeter, you will likely get nothing from trying to become one. And compared to the other social networks, relatively few people use Twitter.

Everyone, in contrast, uses FB. However, building up a professional page on FB is less useful than it might seem. The current search algorithm makes building a free following on one’s business page or personal profile hard work: even bloggers with ten-thousand followers say their status updates rarely get seen.

In contrast, many bloggers swear by Facebook ads. You can target very specific audiences with ads, pay for the exact right readers to see your posts, and direct them to the precise page on you blog you want them to see.

While this approach seems like it works very well, it breaks the “free or cheap” rule.

Secondly: I like the idea of a Facebook group, but given that it’s a separate venue to my blog, and one I need to monitor and oversee, I feel like it’s a thing to do after one has launched a new blog.

What about Pinterest? Pinterest is a massive collection of images, and most of those images link to blog posts. People arrive on Pinterest primed to read a blog post.

And, with an subscription to an affordable app like Tailwind, I can automate and plan which pins I will post. And I can see on Tailwind the stats from the pins I post, the growth in my followers and so on.

The way Pinterest works, if you’re not familiar with it, is that you maintain 10-20 boards, plus the group boards you belong to, and you pin to each board perhaps once a day.

An app like Tailwind makes this manageable. Tailwind is free at first, so you can try it and see if you like it.

It’s also possible, I hope, to create a lot of pins in succession, with an app like Adobe Spark Post or Canva. My plan is to devote a morning a month to producing dozens of my own pins to post, and to collecting dozens of other people’s pins to repost, through the following month.

If you would like a summary of this strategy from an expert, listen to this podcast: How to Drive Massive Traffic with Pinterest, with Rosemarie Groner.

PS the other side of social media success is, of course, getting people to share your content, too.

Some of this is about writing, not tech. My new plan, based on a lot of research, is to write fewer, but longer and more in depth posts. I’m planning to take the time to produce bigger, more amazing essays on this blog — and see how people respond.

The second problem is: most people who visit don’t come back.

Even when they like what you have written, they don’t come back.

My solution here is to offer visitors the chance to join my mailing list.

This is the part I’m most excited about.

I’m most excited to build stronger connections with my readers.

In order to run a real mailing list, you need an email service provider. This is a company that manages large email lists and offers you ways to segment and tag different members of your “list.”

The famous company among these providers is Mailchimp. But to really master the process of building up a list, I looked for an even more powerful option: ConvertKit.

ConvertKit not only manages my emails and helps me organise who receives what, it also allows me to build “opt-in” forms across my site.

Here’s one opt-in, for instance:

Remembers those times I was “freshly pressed”? When thousands of visitors arrived, liked my post, and departed?

If, back then, I had set up a proper series of opt-in forms, and a working mailing sequence (a sequence of mails to explain who I was, introduce the best posts on the blog and so on), I might have permanently benefitted from that surge.

In a normal month, even if only 20% of my visitors join the mailing list, and only 20% of those begin reading the emails I send them, that’s still an extra 80+ interested, engaged people who are involved with my site (at my current level of visiting traffic) every single month.

But here’s the twist.

You can’t just ask people to join your mailing list. People are busy.

And so I’ve designed several “rewards” for different kinds of readers — different kinds of offerings to make it worth their while to join my mailing list.

If you look at my homepage, you’ll see:

  1. A link to the actual mailing list, for people already interested in the blog. But I have put this at the bottom of the homepage because new arrivals are unlikely to be impressed with such a vanilla offering from an unknown (to them) blogger.
  2. A ebook on writing better sentences. This ebook is a revised and simplified version of the most series on my old blog: my 11 essays on prose style. It’s detailed information that is hard to find elsewhere, and it’s among the work I’m proudest of on this site. If someone signs up to the mailing list via that link, then I know they are likely to be very interested in the complex, comprehensive writing advice this site offers.
  3. An email training course for fiction writers. Not everyone is enticed by a sixty-page manual on prose style. So I took some of the ideas from an old blog series on this site, significantly revised and streamlined it (this took a lot of time), and turned it into an email training course. If you like to write short stories, and would like a helping hand for writing the next one, check out the course!

If you would like a detailed guide to how you might deploy a strategy like this, check out ConvertKit’s guide to email marketing. It’s a comprehensive guide to building a mailing list, and while they will (obviously) encourage you to sign up to ConvertKit if you download the book, you can use the techniques they describe with any advanced email software.

The third problem: enhancing the experience for regular readers.

My plan here is firstly to begin a regular newsletter, offering tips on new books, new inspirations, and quick tips on writing.

I also plan to offer additional short ebooks and email training courses — available only to people on the mailing list.

I’m looking forward to asking questions of my readers, to discover what everyone is looking for.

(I would love to hear now what you would like this blog to become, too: email me.)

I also have plans for one or two FB groups, once the site is running smoothly, so that we can get to know each other and collaborate on writing challenges, sprints, and opportunities. But I’m going to take that slowly.

The fourth solution: money.

Right now, I have three main ideas for how to earn some income from this site, and to increase that income as the blog grows. These three options do not include Patreon, which I have been using for the last year: Patreon is fantastic, and you should try it, but I have not had much success turning my Patreon into a sustainable income.

So I need new sources of income from this site.

The first is affiliate income: when I link to a book, or app, or service that I really like, I’ll add an affiliate id to that link, which will earn me a commission from the seller if a reader actually buys the product.

This seems like a good first step to running a profitable blog because it is the kind of writing I was already doing on my old blog, and doesn’t impact the reading experience the way banner and sidebar ads would.

Now, I’m aware that with affiliate links, sometimes the tail starts to wag the dog, and the blogger starts writing new posts simply to describe a thing that they hope to earn affiliate income from. It’s actually hard to find good reviews of Studiopress blog themes, for instance, because the first eight or nine entries on Google are all very bland, formulaic blog posts written purely to generate affiliate clicks.

If you, dear reader, ever feel like one of my posts looks like that — feel free to tell me to knock it off.

Now, if you are curious how this works, the answer is that it’s surprisingly complicated. Amazon has its own affiliate program, which is easy to set up, and lets you link to everything on the store. However, Amazon is strangely willing to throw people off their affiliate program, including as high-profile a blogger as John Gruber, so do make sure you research all their rules.

Some companies run their own affiliate programs, and you will need to sign up individually. ConvertKit, for instance, runs a separate site just for customer referrals, showing your stats and income.

And lastly, a large number of businesses run their affiliate program through a special marketplace site, such as Shareasale. These sites feel rather old and creaky, but they clearly offer a lot of convenience for companies.

The second approach: to use the site as a source of consulting leads. I do a lot of work helping scholarly teams and small businesses produce great writing, and it would be lovely to make that income more dependable and regular. I will let you know how this approach goes.

The third approach, however, is the one I’m most excited about: once I have a thriving mailing list and a fully-fledged blog, I will launch an online writing course. I actually have ideas for at least three courses right now; I love teaching, and I have some very powerful techniques I would love to share with you all.

My hope is that I will launch one of those courses by the end of 2017.


That was a lot of information. If you would like more information about any of the above, send me an email.

Two final points on blogging:

To carry out a lot of the above, you will need a self-hosted WordPress blog. The free service will allow you to do some of the things I’ve described, but not all.

The actual software for a blog like this, WordPress, is free. However, you will need to pay for hosting, for a service to actually maintain your site on their servers.

I use Siteground, because they have excellent customer service.

To be completely honest, Siteground’s dashboard, at least for a new blogger like me, is pretty confusing.

However, once you get used to calling the (very helpful) customer service team every time you hit a speed bump, you quickly grow to like the company. Recommended.

You should also buy a professional theme: this site is built on Studio Press’s Wellness Pro Theme, which I like I lot. I’ve customised the CSS and functionality a bit, and it’s not that hard to figure out how.


This new approach means that I will post less frequently than I once did. No more semi-daily publishing: every blog post will take longer to write and design.

It also means the site will become much less of a personal journal. Posts will be much more reader-focused, solving problems-focused, rather than Daniel-focused, I think.

However, the “about my life” aspect of the blog will transfer to my newsletter.

For now, here is my suggestion to you.

Join one of my training courses, or download my ebook on writing well, or simply join the mailing list.

In addition, as I mentioned before, if you would like to learn more about this whole “advanced email” thing, ConvertKit has produced a free ebook on the subject, offering everything you will need to know at the beginning. Take a look!

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