I've always romanticized the burning ships metaphor and will embark on my journey in a few months. Graeme ... did you move to the US? I'm a canuck in the US (established, have a decent job) but moving up to Canada in the near future. I don't have any concrete ideas about what I'll be doing ... just want to do something independent like the blog author. You describe your first few months as being dismal. Any advice you care to share?
No, stayed in Canada. I do a lot of Skype tutoring now, and sell books to Americans. There would be some advantages to being in Manhattan, but also dramatically higher rent for an equivalent apartment.
I like Neil Gaiman's moving towards the mountain metaphor. I had two objectives: earn recurring revenue, and earn enough in the meantime not to need to take a job. I just kept looking for opportunities that would move me in the direction of those twin goals.
Almost everything good that happened to me in the early (and later) days came as the result of talking to people. I emailed a few of the leading blogs in my niche. I cold-called a small company that taught the LSAT, and offered to help them expand to Montreal.
There were about five people writing explanations for the author of the leading blog. I contacted all of them. One of them founded a startup in the niche. I worked with them for a while, and still have a good relationship with them. That wouldn't have happened if I hadn't said hi. Talk to people.
Always look for opportunities. I got into Reddit early last year. I thought, "too bad there's no LSAT subreddit, I could post my stuff there". Eventually reframed that thought as "why don't I start a subreddit for the LSAT?". That subreddit has now become very popular within the LSAT niche, and it's been very helpful being the moderator there.
Think about what skills would help you towards your goal. "If I could do this, what would I know how to do? How would I do it?". I've learned book publishing, enough html/CSS to run a website on Wordpress, and some basic programming which has really helped speed up web page creation.
Nothing needs to be permanent. Don't say no to an opportunity if it's not what you want to be doing in five years. Is it useful to you today? I also do SAT tutoring. It doesn't hold much interest for me long term, but the money helped me through several rough patches.
Hope that helps. Think about what you want to achieve, and what skills you have to offer that will help you reach those goals.
