I’m more or less obsessed with the idea of writing for a living. Waking up every morning and building something on your own terms, from your own laptop, from anywhere in the world.

To honor this obsession I’ve created a list of over 10 posts (which represent hours of reading and listening) on the topic of making money with your writing. You can find them at the end of this post.

I sure wish I knew about this stuff when I was 22. I’m not saying it’s right for everyone, but how cool is it that you can grab a laptop, run to an exotic beach somewhere, and quite literarily write yourself into an FU lifestyle.

If I was 22 again, what might I advise myself to do with my love of reading and writing?

Hey 22 year old Dan,

This is 32 year old Dan. We are still alive!  If the plan below doesn’t work out, know that the Spurs took the Heat in 5 in the 2014 NBA finals. You’re welcome! 

Ok. Buy a ticket to Ho Chi Minh City in Vietnam. You’ll like it there. It’s cheap and fun and exciting and there’s lots of entrepreneurial types running around sharing ideas.

Save up $5,000 before you go. That’ll give you 6 months of time to work. 6 months! I know you won’t be able to wait that long, so go ahead and open up an Odesk account and get a few clients to cash flow your monthly expenses.

Now, on to business.

Register “SnappyDomain.com,” something alliterative if you can. Try the tagline “Making Book Keeping Easy for Internet Entrepreneurs.” Accounting sucks for internet entrepreneurs, they have unique needs and many would like to keep their books up to speed but it’s complicated. I know you think it’s boring, but don’t worry– money is pretty fun, your customers will be cool people who will open up opportunities for you, and because “SnappyDomain” doesn’t have the words “book keeping” in it, you can always move your services and products towards whatever is working or interesting you.

You can also occasionally post personal and travel stuff at your website too. Many of the entrepreneurs who might be your customers probably share your interests, and that will get their attention and put eyeballs on your offer.

That reminds me. Don’t post any writing until you’ve finished an offer page. How about $350 bucks a month (billed quarterly) for basic book keeping services? The more you can charge up front the better. You’ll have to do all the work at the beginning, just make sure you’re also writing the precise process required to serve the clients you get. That’s your intellectual property, buddy. The very stuff your business is made of!

Aim for 10 clients as soon as you can. Don’t worry about pigeonholing yourself– your tagline, approach, and product can all change. Maybe you’ll end up just helping people use a popular piece of software and earning a bit off the affiliate commissions? Who knows!?

Do I know if this will work out? No. But you’ll be doing things on your own terms. And your writing, which you love to do, will lead you to profitable places, assuming you focus on creating (let’s say) 250 publishable words a day. Do it every day!

Keep working directly with people and solving problems through those words. The offers will change. The margins will adjust. Your clients will spit at your stupidity! But as long as you are willing to write to solve problems everyday, you’ll be alright…

*  *  *

I was recently asked on Twitter why I don’t write about topics that resonate with me on more of a personal level. I very much appreciate the request, but my first thought was “that’s what I am doing!” But I can see why people would be suspicious. Articles like “The Retirement Hypothetical“ might look like a dry piece of lead generation, but for me, they represent the type of expression I’m aiming for. Something hopefully useful and inspiring.

Maybe it’s because I make a living from my writing. That’s a responsibility I enjoy. That’s something I want to keep up. That’s why I subscribe (more or less) to a heuristic I call voracious input, focused output. That means I can go off and be a dilettante on my content consumption– watching Youtubes, listening to audio books, reading blogs– but when it’s time to create I try keep it (for the most part) focused.

And sure, from time to time, write about something that is personal. You’d be surprised how stuff like that can bring in customers.

I remember a few years ago I went back to the states to attend a parking industry conference. I was having trouble making connections with the big clients. You know what broke the ice? Was it our new lifetime guarantee on our products? (something Ian and I obsessed about for weeks). Nope. It was, predictably in retrospect, my love for Bali that got the conversational ball rolling.

But back to writing. Here’s a few things I think are important:

You only have so much creative energy, consider creating a ‘main creative event’ that efficiently captures it.

I certainly squander tons of my creative energy. But rather that cultivate a bunch of side projects to satisfy an expressive craving, or building something less focused and more eclectic, my approach has been to focus on a main creative event that efficiently harnesses my creative energy. For me that’s this website.

When my energy changes, I suspect so will this brand.

The skill of writing is more powerful than ever. 

Cash flowing your education by writing about book keeping for a few years might not be such a bad long term investment. Especially given that marketing products is becoming more expensive than building them. It’s harder to get attention, and it’s easier to get prototypes.

This is why people (generally speaking) don’t stay marketing consultants, content writers, or PPC consultants for long– if their work is actually effective, they are often providing their clients with something more valuable than the product the are promoting– attention and trust.

That’s also why good writing trumps good ‘copy.’

Anybody can play around with existing sales pages to get them to convert better– tweak guarantees, split test headlines, toss up some testimonials.

But who can write sales pages that work in the first place? Writers. I’ve seen endless sales pages over the years with copywriting tactic and trick and “surefire method’ strung together that just fell flat on their faces. The problem? The offer had conceptual holes. Failures of logic and imagination that prevented the reader from trusting or even understanding the offer long enough to take an action.

The reason “copywriters” don’t last long in entrepreneurial circles is that often when they find out that the “copy” part wasn’t nearly as important as the “writing” part (and so they start becoming effective), they put it to work for themselves and not their clients.

The practicing preacher.

One of my favorite trends online are practitioners taking the time to record, more or less in real time, what they are learning and doing. Some examples would be Benny, Kelly, Rob and Mike, Dan and Alex, and Patrick.

An effective practicing preacher might spend 70% of their energy tossing themselves at difficult problems in their space, and 30% of the time documenting, analyzing, and attempting to make their practice legible to others.

What I love about this trend is that these bloggers create more nuanced and accessible scripts than were available to me before bloggers and podcasters found ways to make a few bucks off of their work. (The preaching part isn’t cheap).

You could say practicing preachers are a sort of gonzo blogger (WIKI), or a journo-preneuer (ask yourself if your favorite bloggers has a Lawyer Mind or a Judge Mind). I certainly felt gonzo-ish when I started my outsourcing blog (the full story in the links below), and am seeing many writerly types around me have success by throwing themselves into interesting situations and writing their faces of off. I suppose there is nothing new here. Doing something interesting has long been a staple of good writing, it’s just that now you don’t need an editor to send you there.

Speaking of traveling… don’t get me started on travel blogs (and please don’t start one).

The failure of travel blogging.

The monetization strategies in the travel blogging community are, from what I’ve seen, a complete disaster. It’s a shame because if travel bloggers took a more entrepreneurial approach to their writing, they might find that they are uniquely suited to create content that has commercial potential. Instead of a “watch me travel” blog, start a “watch me open bank accounts” blog. Again: be a dilettante when it comes to traveling (input), but not when it comes to your work (output).

Enough! Here’s everything else I’ve written about this so far. Much more to come, I’m sure, as I see the opportunities for micro-publishing and writers expanding.

So, is blogging still a viable way to start a business?

The opportunity, in my view, has never been bigger. “RSS is dead” and “Twitter is taking over” is tech talk. The world still needs more great blogs, written from experience and with care, solving problems and providing inspiration.

Now who’s going to start the book keeping blog!? How much more effective would all of these entrepreneurial interview blogs be if they asked about finance and accounting (as part of their questioning) and had an offer page for financial services?

The complete series:

1. Dear Entrepreneur, Don’t Start a Blog
2. 100 Online Marketing, Entrepreneurship, and Personal Development Blog Posts Later…
3. How I Built and Sold a Blog Valued at Over $200 a Post
4. 100 True Customers
5. Teaching Beginners is Good Business and Other Internet Marketing Dogmas
6. Making a Living By Writing Blogs
7. Prevent Your Blog From Dead on Arrival Status : Consider “Buy Now” Blogging? [Also see: Pay-Now Podcasting]
8. 101 Monetizable Blog Topics
9. Is Starting a Blog Hazardous to Your Entrepreneurial Health?
10. Simple Blogs, Written From Experience, Can Change People’s Lives
11. [Podcast] Should You Be Blogging?

Thanks for reading! As always, would love your thoughts.

Cheers,Dan