AMA: What’re the Opportunities in Writing?

D. checks in with:

I met you briefly at Summit this year (I know you meet a lot of people so I don’t expect you to remember) and I was wondering if you could offer some advice.
Like many in the PS community I work full-time in IT, but I also do a lot of freelance writing for a few different sites. I started writing about a year ago primarily for some side income but also obviously because I love what I write about and wanted to become active in our community. In addition I am also active on Twitter and I am looking to increase my public speaking opportunities.
I guess for the time being I am trying to walk in the foot steps of yourself and others who have done the same sort of work. I am hoping you could provide some insight into what future opportunities would be possible based on writing, speaking, etc. I see certain people become tech advocates, authors for example. For me, understanding what is possible would probably help me decide what direction I would like to take in the future. Being you are prominent in our field, I think you probably have a good idea of what avenues are possible.

I hope you’ll ask a question, too! Visit here for info. And here’s the list of everything asked so far.

So, I’ll tell you what I did; I know this is largely echoed by guys like Greg Shields and Jeff Hicks, although it’s by no means the only path.
Writing tech articles for outlets like TechTarget, 4SysOps, 1105 Media, Penton Media, and so on is great. You’re usually writing short-short stuff (~800 words), but you’re also getting small-small pay (think the $100-$200 range). You do that stuff to build audience. 
Conferences are about the same thing. You’re looking at $0 to $450 a session in most instances, and some will cover travel while others won’t. Again, you do it to build audience. Start looking at the conferences that cover what you like to speak about, and then dig for their Call for Topic (Speakers, Papers, whatever) email lists, so you can get a notification when they’re open. Have a solid bio ready to go at all times, and do as much as you can to create a public “presence.” Conferences hire speakers mainly for their attendee-drawing power; expertise is kind of assumed.
So once you have the audience from all that, what good is it?
Greg and I made most of our Concentrated Tech money doing webinars and white papers for ISVs, often through media companies like 1105 Media, Penton, Realtimepublishers, and so on. We’d basically get on a call with the vendor sponsoring the piece, and get them to brain-dump whatever it was about their product they were trying to promote.
“Dude! You sold out!” I can hear some folks thinking. Actually quite the opposite. Greg and I felt – and still feel – that IT pros are deeply under-informed about what tools are available on the market. Our people don’t research much, which means they can’t personally be a “part of the solution” when their business needs something. I see people hand-coding stuff in PowerShell or whatever that would be cheaper to buy once you account for all their time. So we took it as our mission to take the vendor’s “ulterior motive” sales pitch, and then distill that into meaningful, factual information that an IT pro could consume in ~30 minutes. The vendor was happy because someone was speaking to the audience they wanted to reach; readers/viewers were happy because, while we were covering what a solution alleged to solve, we weren’t selling it. We’d talk about the business-level challenges, talk about a lot of the details of those challenges, and then talk about what a solution would look like. It was up to the vendor, still, to prove that their solution met the need; that’s sales. Our job was to help people understand the space, and give them the knowledge that would let them evaluate all the solutions in that space for suitability. That kind of thing pays a lot better. Getting “in” can be difficult; for us it was a matter of making connections at conferences. There’s nothing like face time in today’s world.
Books are obviously an opportunity, and sites like Leanpub have made it easier than ever to self-publish something, even if you finish it and take it on to Amazon or whomever. Think concise: if you’re like, “I could never write one o these 800-page tech compendiums,” good. Don’t. People don’t like reading them. Pick a problem and write 100 pages on how to solve it. The joy of ebooks is that there’s no economy of scale, so writing small is completely possible. I have to admit that I’ve gotten jaded about traditional publishers. You have some who are really good, like Manning, although they’re hampered by the nature of the business. You have some who are just exploitative, especially for new authors. But in all, making $1 a book or less when you’re the one who wrote it isn’t very fulfilling.
People both over- and under-estimate blogging. Blogs are great for posts like this one, but they’re a terrible way to learn long-form topics. Blogs aren’t organized, and they don’t provide a “path” for learners; they’re a journal; the word started as “web log.” I wish more bloggers would take a hot minute to organize their material into an ebook and create a true learning experience. Instructional design is a thing.
Hope that helps!

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