I was in your shoes, and I know your pain. It's the awful pain of knowing that you live in a time where you could work from everywhere, and yet, YOU are the person who is still stuck in an office almost the entire daylight of your week and when you're not in the office, you're sitting in traffic. You're living a near industrial era life in a post tech world. You know in 100 years they will write in the history books about the tech generation that sat at desks in front of a screen typing 8+ hours a day with no windows. You feel you're literally watching your short life wither away while other people are sitting on the beach in Thailand with a Macbook Air under their umbrella.
Let me explain how I personally got out of this situation: I became a software consultant. For sure, it's not something you can become overnight, because you need clients, but it's a good way to get out quickly versus the ivory tower of starting your own profitable product offering. Heck, 37 signals and Fog Creek started out as consulting firms.
How do you get started as a consultant? It's easy to find articles that explain how to choose better clients and things like that, but how do you get started?
I started to give a vague answer, but I realized you asked specifically how I got started, so I'll answer that:
I took any random job that came up. First it was updating the website for my friend's art gallery getting paid $20 an hour in trade out when I was in college. Next it was helping out a friend who was doing a larger contracting project, then I did a project for someone who I randomly met at a friend's party. Before I knew it, I'd been doing little contracting projects on the side for 10 years.
That's when I decided to make the jump into full time. I didn't have the client base to do that, but I had the experience and confidence that I could present a professional front. I had business cards and invoice systems, time trackers, etc. I then did a similar thing to what rfnslyr described doing when starving: Find a product that companies need and you can build with your skills. Then it's just a matter of knocking on doors. Last year I cold called a company with a proposal on how I could augment their business. A month later they signed a $40,000 contract with me to implement stage one. Since then, they followed on with two additional contracts and now I have an open ended contract with them to work "As many hours as I have time for." The important question is to ask yourself what you can offer that will add value to a company. There are opportunities all around you for that. You just have to think a little bit outside the box. The really traditional and obvious ones are SEO type stuff and building websites, so those will in most cases have the least rewards and the most competition, but there are so many more out there.
I did the same things. Loads of reading and asking to find that "golden path" or secret to make it click. "How do I consult?"
Well, find a job somewhere, preferably a large corporation. Lots of people run their own consulting gigs on the side. Talk to them.
I found out a few people, just around my cubicles, run a consultancy on the side with a few people hired.
I started working part time for their consultancies as we're always in the office together, then once my contract at the company finished, I knew abut 5-10 people that consulted so I got a few gigs with them. Boom, now you're a consultant.
Best way is in person. The easiest gigs I ever had was when I was nearly starving and needed money. I went out, went to every business I could find that could possibly use a website with a proper backend (so I can take more time and bill more, don't want to do just frontend work). I got about 20 gigs that day, only completed a few over the course of the next year.
Two ways: talk to people you work with, or really go out there and STOP Googling and reading. There is no magic path, just do it.
OR, find an existing consultancy and either try taking out employees to lunch and talking about it, or work for a consultancy for awhile and take notes on how everything operates. How clients are landed, billed, how talent is acquired, etc.
I like the example you gave about offering websites with a back end by going door to door because it's different than what most people say when this question is asked. You made a product to sell: Website for the business; then you went out and found the client. Most people talk about showing love to your current contacts and working through your existing network by referral which just isn't feasible for everyone. Plus, doing that route, you're not really picking your clients. You're just hoping good ones fall on your lap through your limited network.
It's easier going door to door. When I was marketing a small app, I went door to door to over 200 houses. I met lawyers, coders, bankers, and cool people that invited me out for coffee just because they're curious about my ventures.
It's also better if there is a back end. Usually means they will want some specific feature that you can charge to build and cash in on maintenance costs. A proper backend takes way more time than frontend too, and people like to be in control of their data ;)
Most of the time I'm just writing a custom WYSIWYG editor for custom written blog software. Reinventing the wheel every time.
One more thing.. don't be afraid to ask pressing questions. It's not your job to take care of their insecurities. If they feel uncomfortable answering a question, it's their job to say so. I ask things like "how much did you make last year from this gig?", "how did you get started initially?", "how much did you pull in your first few months?". It's all just nature of the business, money.
I've working in consulting-type roles for a long time. The biggest problem for solo-operators (or even with a couple employees) is that most clients require you to be in their offices...
Let me explain how I personally got out of this situation: I became a software consultant. For sure, it's not something you can become overnight, because you need clients, but it's a good way to get out quickly versus the ivory tower of starting your own profitable product offering. Heck, 37 signals and Fog Creek started out as consulting firms.