Ask HN: Will self-employment sink my resume?
I'm currently at a job that, like many posters plumbing the well of Ask HN for wisdom, I'm less than excited about. I exist in a limbo between developer and marketer, but usually write more than I code, and about subjects that don't interest me at that. I like my coworkers alright, but have been thinking more and more of going my own way. Although I'm a junior dev, there's really no one to learn from as no one in our IT department can code (all great people, just not much for me there) and the rest of our work (that I don't do) is contracted out to remote workers.
Right now I'm blessed to have insanely low expenses - a product of sharing an apartment in one of the cheaper neighborhoods of Austin and driving a beater. That, combined with some savings and what I know I can reliably pull freelancing, mean I'm more than confident I could cover all my expenses for the next 6+ months (if not indefinitely). I have tons of ideas, both for development and more writing/journalistic projects and have already started to draw a small monthly income for some of my work.
My question, for all the HR people and tech recruiters out there: Will this sink my employability long-term? Although I think it's bullshit, I could see some future recruiter looking at my resume and thinking I'm too much of a bleeding-heart, anti-establishment type (which wouldn't be far off) and not worth the risk. Truthfully, the greater autonomy is why it appeals to me so much.
And if I do get dinged, is there anything I could do to lessen the pain? I'm active on Github and plan to OS some of my projects. What else can I do? I blog and try to do all that jazz when I can.