Blogging about blogging is pretty meta, but it’s how Ryan has built and sustained a successful blog for almost 10 years.
He’s gone from documenting what was and wasn’t working in his day job to writing about freelancing and building digital products for other writers like templates and courses.
What was once his side gig has turned into a full-time career. On this episode of The Long Game, Ryan talked to us about his work process, how he creates and promotes content, and how sometimes you have to turn down high paying work to reach your goals.
- Build a blog with struggles and success
- Let disengaged subscribers go
- Build your email list with targeted offerings
- Turn down work that no longer fits
- Balance creating, updating, and promoting your blog content
- Use reader questions to inspire posts
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17:43 – Build a blog with struggles and success
Ryan built his blog by documenting his mistakes and triumphs in both his day job and freelance work. Eventually readers started asking for specific content, and he was able to monetize it.
“I think even to today is just documenting my process, what works, what doesn’t, everything in between. But it became largely about freelancing when I was freelancing full-time. So sharing things like templates and tips, tutorials, resources, getting a little bit into the monetization at that point in time. It was really service based. I was just selling my freelance services and eventually enough people were downloading my free stuff that I asked a few of them, what kinds of problems do you have? And eventually did a proposal writing course and some contract writing courses and just little mini digital products that I could begin to monetize in a more scalable way. And that just naturally took me to getting a couple of hundred thousand readers a month, I would say. And then more and more people began asking me, how do you get traffic? How do you monetize an audience? And so today, if you look at my site, it’s essentially blogging about blogging. Pretty fucking meta. And courses, affiliate revenue.”
22:14 – Let things happen organically
Don’t force yourself to do things on a schedule if they don’t have to be done that way.
“I’ve been such a strict adherent to calendars and to the inbox zero life too. And I think one really unfortunate by-product for someone who’s working on being less rigid and less structured, for me, is that I can like sometimes feel like I’m failing if my inbox is piling up in a way that feels out of my control. Or if my schedule has too many things on it, I’ll feel overwhelmed at times. Learning to not need to have blocks of everything on my calendar, making time for something like just writing. I like to now approach that much more organically. If it’s a day that I wake up and I feel like writing, then I write. And some of this speaks to the specific position I’m able to be in right now with working for myself.”
32:37 – Use the morning for good habits, not work
Ryan said how he spends his morning impacts his thoughts, feelings, and actions. He chooses to use that time for exercise and meditation instead of work.
“During weekdays I try and always start my day with a morning walk when it’s still really crisp and fresh out. And there’s just a really good feeling that I resonate a lot with being in nature early in the morning. And then some physical activity doesn’t matter necessarily what it is, whether it’s a morning run or lifting some weights, doing a yoga class. It doesn’t really matter so much as long as I’m moving my body, stretching even. And then meditating and journaling. Those four things have been a complete turnaround from what my life was even just a year ago. I would a year ago dive straight into work first thing in the morning and I had this holy view of the morning hours are your most creative and productive time of day. So it’s got to go towards work. And as a result of doing things like therapy and thinking much more about who I am, who I want to be, I realized that I don’t want to any longer give my most sacred morning hours to my work.”
40:47 – Let disengaged subscribers go
Ryan very recently went from 150,000 to 105,000 subscribers by removing a large chunk from his list. It’s an example of how he’s trying not to romanticize things.
“I think a business example of that for me, today actually, was that with my partner I decided to remove 45,000-ish subscribers from my list. And I realized that I felt some friction towards doing that. And once I spent enough time thinking about it, journaling on it, I just came to this crystal clear place of, that’s my ego that wants to retain these people that haven’t opened an email in nine or 12 months. And the reality is that 99% of those people will never open an email again because they’ve moved on. They’ve gotten what they needed, decided it’s not for them, whatever. And it was really my ego that wanted to hold on to having this larger email list, even though those people weren’t really there. So that’s another thing, decoupling ego from my business as another great example of not romanticizing.”
42:50 – Build your email list with targeted offerings
Pair well-researched keywords with free templates and courses that will pull people into your site from Google and lead them to subscribe.
“It’s been I’d say four to five years of very consciously list building. And that includes things like pursuing exact keyword phrases that I know would be paired perfectly with a free course or a free template or some sort of downloadable. And one example of that is blog business plans. So I wrote an article about how to create a blog business plan, the five things I think that you should focus on in the early days and tracking your trajectory, how you’re doing towards your goals. And that was perfect for a template. And that’s just become something that, as I do all these things, we’ve been talking about guest posting, strategic partnerships, ways to get more high quality links to my content. I rise up in the search rankings and people click on the article, people that want the template grab it. They joined my email list and eventually I monetized more and more starting probably two years ago in a more thoughtful way with digital products.”
47:33 – Let go of perfectionism in course building
Your first time creating a course can be a way to validate that there’s an audience before you create an even better one. Don’t let perfectionism hold you back.
“Unrolling the perfectionism a bit here. I think you can do courses that are designed around validating what your more perfect course could look like in the future. And maybe even that validation course still takes you a month to put together and you’re just doing Loom videos and recording stuff with your iPhone on a tripod with a ring light or something. I think there’s something to be said for just shipping a basic course that ideally if you’ve done your homework and you’ve validated that people on your email list or people who come to your blog have this real problem that you’re working to help them solve for the course. I think that’s great. Now I feel much more I guess confident in the support I have to get something like a script a day from my team and know what to talk about for doing a couple of videos. And being able to just knock out a course in a few weeks versus something that I would sometimes agonize over for months. Be like, oh God, is this even good at the end of it?”
52:58 – Turn down work that no longer fits
Think of the opportunity cost, not just the money you’d make from work that isn’t what you want to be spending most of your time on. Ryan recently turned down a big project that would have taken time away from what he wants to focus on.
“I’ve got this team now with my business partners who can probably help with writing the content and help with marketing it. This would be really easy, right. Free money. We all love that. But I allowed myself to sit with that for 24 hours, think about how I want to allocate my time and my energy. And I realized my heart wouldn’t be in that at all. And me as the person, the brand that they reached out to, they would expect me to be involved or they would want me to be involved. And maybe there’s a conversation to be had about like, Hey, here’s my agency, work with them if you want. But I think even just having something like that on my mind would be an opportunity cost distraction away from all these other things I want to do. Like growing the affiliate revenue, growing traffic and building more digital products.”
57:08 – Balance creating, updating, and promoting your blog content
Ryan keeps working on building his blog traffic by splitting his time between writing new content, updating old content, and promoting everything.
“It’s essentially, always, I think for me, going to be a combination of publishing new content and updating existing and promoting just everything site-wide. But if I’m being honest, there’s kind of a top five or 10% of articles that drive the most traffic and thus get the most promotional attention from me. But looking at my upcoming log of content, there’s almost 40 articles in there, virtually all of it about blogging, writing, podcasting, driving traffic, monetizing a website, all the topics that I’ve kind of decided to go all in on at least for the foreseeable future. And we’ll see. As I change, what I want to publish about changes too. Finding that balance, it’s never in perfect harmony of I’m killing it on all fronts. I think it’s a matter of course correction too. Being the creator, doing some outreach or managing the inbound partnership opportunities that come my way too, and doing things like advising, guest post writing.”
58:55 – Promote your content in ways you enjoy
Ryan tries to stick to the rule of promote 80% of the time, create 20%. That’s much easier if you stick to channels where your audience is and that you enjoy spending time.
“The vast majority of the time for me that means guest blogging. There are other things that fit into the wheelhouse. Answering questions on Quora. That’s been a really fun one. I want to get back to that, but it takes so much time for me to write really thoughtful answers on Quora that won’t get downvoted if you link to your blog at the end or something. So you have to really overcome a value threshold. That probably applies to every platform you’re publishing on. Social media a little bit, although I haven’t been as present and I think my intention with social media these days is to just be present on just one channel where I know my audience spends time, rather than trying to mechanically send out 10 pins a week and five scheduled tweets and a clickbait-ass LinkedIn status update. So I think to each his own, but focusing on just a couple of things has always proven to be the best for me.”
1:01:42 – Use reader questions to inspire posts
Ryan thinks his best posts are the ones where a reader question inspires him. He also writes some SEO-targeted posts.
“My most favorite at least is when I get a reader question that inspires something and that’s when the article really comes from within. And I try and seize those moments to just very quickly write an outline as a reply to the email, maybe. So here’s my quick answer and ooh, you really inspired me. I’m going to write an article about this soon, so stay tuned for that. But those are the ones that I often write myself and I don’t want to give to another writer because I’m like, ooh, this is gonna be so fun. This is going to be really authentically me. But there’s some that is definitely much more strategic, keyword focused. Taking a look at the landscape of what competitors are writing about sometimes too is fair game. But I spend a lot of time in Ahrefs just looking at different keyword ideas that either come to me or I find from content I see out there on competitor websites.”
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