Ask Colin: Starting a Blog

Hey Colin!

I dropped you a line over a year ago about how I was leaving my stressful job for a less stressful job that afforded me more time to do those things that I loved.

Since then I have gotten divorced, found the best partner in the world, and am back to looking at jobs as I find my current one unfulfilling. I struggle with looking for jobs that are fulfilling yet still afford me the opportunity to have a life.

I have also been struggling with feeling “behind” in life. I am 29, divorced, childless, I don’t own a home. Even though these aren’t necessary metrics of success, I find I still come back to this thinking pattern. It is something I am working on and one way I am working to think differently is to incorporate more of what makes me happy even if the mainstream world wouldn’t approve.

I have started to really dig into frugality and minimalism. I have found myself more and more wanting to share my story, my words. In the past I have wanted to start a blog because I wanted to make money off it. I wanted to be an influencer and have the life of the bloggers I followed. Now I find the call of starting a blog just to get out in the world and connect with others who share similar ideas of what life really means.

But I have the old thinking creeping in of ‘I have started this before and didn’t see it through so why start again?’

Why start again? Because I have the fire to connect with and support those who go against mainstream thought of life has to be lived a certain way. I desire this connection and I desire for my story to be known and shared.

Anyways, I was wondering if you have any advice on where to start? Just a free wordpress site and start commenting on other bloggers sites who have similar views as mine?

Thank you for always being here and for sharing your story and giving hope to others,


Hey Amanda-

First of all: congratulations on making those changes in your life, which sound to be working out splendidly. Change can be difficult, but you made it through and ended up with something more you-shaped, which is wonderful.

Second, kudos for continuing to question the status quo and for asking yourself how things might be even better. This can be particularly difficult for those of us who aren’t keen to adopt common metrics of success, as it means we’re more perceptually on the hook for any missteps or failures—whereas pursuing well-worn paths allows us to curse those who carved those paths, those who sold us on them, and the society that adopted them as normal.

Ultimately, this means you’ll almost certainly end up with something even more you-shaped, but it also means you’ll have to do more hands-on work to get there, and as you continue to reassess and recalibrate things, across all facets of your life, in the future.

That said, your desire to blog, or more broadly to document and share what you’re going through and learning along the way, could aid you in your efforts to find work that’s more fulfilling according to the standards you care about.

As someone who’s been blogging for a decade, though, I want to start with a caveat: most blogs will never earn a cent for their creators, and the tried-and-true methods of earning some kind of living via blogging from previous years—namely, advertising—is a dying species of business model in 2020, and has been for a while now.

That’s not to say that online advertising isn’t still a sprawling beast: it still underpins the majority of the online media ecosystem, from newspapers to YouTube.

But there are indications we’ve reached peak-ad, and that it’s a revenue model with plenty of holes in vital places. Browsers that block ads by default are increasingly common, plugins cover the rest of the browser world, and a lot of the most lucrative advertising has either moved to the app ecosystem, onto platforms like Amazon, or adopted a fee-structure that’s pretty much only useful to massive media entities that receive bajillions of clicks a day.

As a consequence, most bloggers—myself included—typically use their blog as a jumping-off point for other things they do; a method of what Seth Godin calls Permission Marketing: a contrast to Interruption Marketing, which involves interrupting something the viewer/reader/listener is trying to enjoy with an ad, you instead gain their permission to engage with them by giving them something valuable.

In the case of blogging, this typically means creating something of value (a blog post) and giving it away to people who will find it useful, and that serves as an entry point to your other work: things people might be willing to pay for, and which you don’t have to market aggressively because they already know you and your work via that blog (or whatever else you’re giving away).

This more broadly beneficial model has grown in prominence in recent years with the emergence of entities like Patreon and other services that allow creators to earn money in the form of donations, micro-sponsorships, and patronage: consistent donations over time.

As a result, the most successful bloggers—in terms of becoming financially sustainable and in terms of being able to create work they care about, rather than work that is optimized for page views and clicks—tend to bring people in and then either gently nudge them toward something else the blogger has created, or toward becoming a sustaining member via direct contribution.

The latent, non-monetary benefit of blogging, though, is that it helps you connect with other people, and can get your name and work out beyond your existing professional and friend group.

Write about a particular topic in a way that others find valuable and you create a type of gravity that pulls in folks who are interested in the same sorts of things. Over time, this can grow to the point where you attract new opportunities, both of the social variety—meeting new people from around the world—and of the professional variety—freelance writing gigs, consulting, speaking opportunities, book deals, etc.

The specifics will vary from person to person, of course, and vital to mention here is that the audience and monetary success rate on anything put online is still abysmally small. The publishing tools we have available today have added an abundance of new voices to the mix, including those that were often left out of previous conversations, which is wonderful. But those same tools, in making publishing of all kinds more accessible, have also triggered a deluge of content that can subsume even the best work produced by the most thoughtful and engaging person.

Put more bluntly: the chances of failure are far, far higher than success. And that’s true whether you’re aiming to make some money from your blog, or whether you’re simply hoping to get a few hundred people to read what you write.

When you publish something online, you’re competing not just with the ~600 million blogs that are publishing ~2 billion blog posts a year, you’re also competing with Netflix, Facebook/Instagram/Twitter, YouTube, Fortnite, and, taking a broader view, all other possible pieces of media, entertainment, or activities (including sleeping and eating and sex) in which a person might engage.

And that’s…a lot. We’re up against a lot of really amazing stuff, and a functionally infinite amount of really mediocre-but-noisy stuff, any time we want to claim a set of eyeballs for even a few seconds.

I say all of this not to dissuade you, but to set the expectation bar as low as possible.

If you attract even one steady reader, that’s already a shocking amount of success in the world we live in, today. Even that level of readership is something to be proud of, both because you’ve created and shared something that is valuable to someone else, and because you’ve beat the internet odds.

I also say this because it sounds like you have the right attitude to give blogging another go, having moved beyond the desire to influence, in the newly mainstream sense of the word, but I don’t want you to get caught up on unfair metrics of success in this space, having done so well in changing your metrics in other aspects of your life.

It’s not obvious that blogging is complex and that a part of what determines who gets popular online is the result of luck and the Matthew Effect, which says, essentially, that those who are already popular will get more popular, while those without existing audiences will often struggle to even get noticed.

If the practice of writing and sharing can itself be rewarding, though, you’ve already succeeded from day one. You’ll be able to focus on the right things—doing good work that speaks to the right people—and success beyond that will be almost incidental.

All that said, you have a large number of options in terms of where you publish your work, all of them better and worse in different ways, most of them pretty overall decent.

Something like 30% of the entire web is build using WordPress, and their simplest setup is similar to joining a social network like Facebook: you go to and sign up, choose a blog design, and start writing.

That approach is great if you want to just get cracking and focus on the specifics of your structure later, but it can get pricey later if you want to use a custom domain (a web address without “” in it), or if you want to add other pro-level options; that’s how they earn their money, so they charge for those conveniences.

A better option, if you plan on building something for the long-term and don’t mind spending a few bucks, is opting for WordPress’ Open Source version, which can be found at

The downside of this option is that it requires you have a hosting plan through a hosting company, which can cost anywhere from a few bucks to thirty or forty bucks a month, depending on your plan. It also sometimes requires that you do a little fiddling with databases—thought most hosts these days have one-click setups for WordPress pages once you buy a plan, so that’s less of a concern in 2020 than it was a handful of years ago. (I personally use and love Hostgator, which has a one-click WordPress install, but there are a lot of solid options out there, these days.)

I’ve used the Open Source WordPress option for all of my sites since I started blogging back in 2009, and as a versatile, generally safe and intuitive option, it’s wonderful. There’s a reason it’s the most popular content management system in the world.

That said, Ghost is very similar to WordPress (in that it has paid and free, Open Source versions) that purports to be a little more focused on blogging (whereas WordPress has become the everything-CMS, used for websites of all shapes and sizes), and they seem to be doing some interesting things, if you’re keen to check out a blog-world underdog.

Another option is perching your writing on a platform that also serves as a publishing-focused social network.

Medium, which was started by one of the founders of Twitter, is the most popular entity of this kind, allowing you to start your own blog and to have that blog connected to a preexisting ecosystem, with “claps” (likes) and shares, follower counts, and other trappings of traditional social networks.

There are pros and cons to that setup, of course: you might stand a better chance of getting in front of people when there are algorithms helping folks find each other, and understood methods of demonstrating credibility and enjoyment; most isolated blogs lack these tools. Being on such a network can also incentivize certain types of not-great behavior and writing, though, which could be antagonistic to the type of writing you want to do, and the sorts of relationships you want to build.

There’s also the latent issue of ownership over you work when you build it on a site you don’t control. If Medium disappeared tomorrow, where would your work go? Who benefits most from you publishing it?

This is true, too, of networks like Substack, which allow for publishing within an ecosystem. There are benefits, but it is also ultimately owned by someone else—a corporate entity that may not share your priorities and goals, or which may currently share them, but someday be sold to another company that doesn’t. It may never be an issue, but it also very well could be.

I prefer to own most of my work, personally, for a variety of reasons, but in some cases, I find value in publishing on preexisting networks (this project is based on Substack, for instance). It’ll be up to you to balance the pros and cons for yourself, for each project you create.

Many people find that a free option (like WordPress’ .com platform) is a good place to start, as it allows you to find your feet, work on your voice, and try your hand at the habit of blogging without investing a cent upfront. You can then, when you’re ready or hit some kind of milestone, transition over to a paid option based on what you’re willing to invest, knowing what you’ve come to know.

You may also decide to stick with that free option forever, though; many people do.

Many people also start investing from the beginning, however, believing (and there is some research that backs this up) that making some kind of monetary investment, even a small one, makes us more likely to commit to new habits; we spent the money on the domain name and hosting, so we’d better make use of what we bought, right?

My overall suggestion, in addition to all the expectations-focused caveats I listed above, would be to try a lot of things out, focus on your craft and your habits, figure out what you offer that no one else can offer in the same way, and over time adjust how you publish based on what you want to say and who you want to say it to.

View each of the tools you have at your disposal as tools, rather than identities—you’re a creator who publishes on WordPress, or who shares things on Instagram, not just a blogger or just an Instagrammer—so that you can continue to evolve your craft and thinking as the tools available evolve. You can be vehicle-agnostic, rather than locked into one particular medium or platform.

And hold on to that fire in your belly that’s making you want to share what you’re learning and experiencing with the world. There are a lot of valid reasons to create, but that one tends to amplify all of the others in very positive and empowering ways.

Recent Posts

  • Staggeringly Valuable
  • Scattered Thoughts About Random Things
  • Envisioning
  • On Having Agency
  • I Can Take It