Becoming a Freelancer Again
sparklewise.com
sparklewise.com
My $.02: differentiating yourself as a Python thought leader immediately limits your target client base to "people who know what Python is", which is a base with particularly high standards and relatively low budgets.
I think you'll find that becoming known for creative applications of code (e.g. Python) against certain niches will far outweigh trying to become a "Python thought leader."
Since you mentioned an interest in Internet marketing, you could quite literally write the book on, say, how law firms can attract new clients through their websites, and use that as lead generation for lawyers who want to understand the terrain (this Internet thing and how it can make the firm more money) but understandably don't have the time between lawyer-y things to actually do it themselves.
One things I'm REALLY big on is providing free educational seminars for a particular niche. You could call up a handful of local law firms, let them know you're an author who just wrote a book on how law firms like theirs can get more clients automagically through their website, and invite them to an in-person seminar where you'll dive further into the subject. You just might sell a few copies of your e-book this way, but more importantly, you'll be able to sell at scale and in a way that's not as intimidating (to the lawyer who realizes you're trying to close a deal) as a one-on-one meeting.
I have literally millions of qualified contacts that span over several dozen verticals.
Why do you think it makes a difference?
It's risky for a business to hire someone to "write code", which is how the average freelancer positions themselves. The act of writing code doesn't necessarily translate to the hiring business being better off than they were before they hired you.
Consultants positions themselves to align with the underlying business problem and recognize themselves as an investment vessel, not an expense. "Ah, so your employees are wasting dozens of hours a week on dealing with this crazy Excel spreadsheet that runs your business? Let's find out how we can put together a solution together that will dramatically lower the time spent fiddling around in cells. A quick back of the napkin calculation... your employees dump about 30 hours into this spreadsheet a week. If you're paying $50 an hour to keep these people on payroll, that's close to $100k a year in spreadsheet overhead. Here's what I'm thinking..."
If this is a new product project, a firm is simply positioned better than a sole freelancer. Business value stability, and a firm provides the perception of stability.
An example: Programmer: I'm a freelancer. I will make this website for you. My rate is $X/hr. We can expect to have it done within a month.
Firm: A partnership with us will provide you with a vehicle to double sales and reduce costs by 10% due to employee labor time.
You could also say: This contract service will output a service which will save your sale's reps 100 hours in time per week.
All of these "outputs" are typically a website. A client doesn't care what you pick to do it. They care more about how you produce value and what you do for them.
One is positioned as a cost. Another as a value add. Not only will you be able to charge in proportion to the value add, but you won't limit your amount of revenues you can make with a client due to trading time for money rather than value.
As a freelancer, I was seen as disposable. Akin to a construction worker standing in front of Home Depot waiting to get some work. As a firm, people see it as a place that provides solutions to their problems. If they need some software written, they can come to the firm, and it will be done dependably. As a freelancer, they would call me, and hope I was available.
The only downside to the firm is that people believe it is more expensive to employ it, than to hire a freelancer. I still work for the same rates as before (lower than in the Valley). If another developer has to be sub-contracted, then I start to negotiate from the developer's rate. I only charge a bit more to cover risk (insurance, mostly). But all of the people in the my network have proved to be reliable and hard workers. Once (we) programmers find a good source of work, we treat it with love and respect.
I will take the opportunity to invite anyone who might be interested in getting to know the firm to contact us through our website(in my profile).
We have clients come to matchist (http://matchist.com/talent) often looking for a solid developer with other areas of knowledge like marketing.
In my own past experience as a freelance web developer, clients always liked when I had additional knowledge and skills to add to their needs beyond just plain coding.
People who position themselves as something more than a person who writes code do better in the long run. I think developers forget that anyone outside of our bubble have no clue what the technologies are or what they do. They just want their problem solved.
I hear you for your roadblock - I also find it hard to come up with a strategy that uses your skills, with things you love, and that meets a market.