Today I made the plunge, and I ended my last day under normal employment, to pursue my career as an independant contractor and eventually to form a startup. My journey from here will hopefully be a good one, though I am sure it will not be without its hiccups. I'll post how things are going, and write about what I learn for anyone else who is thinking of going this route. I need to look into things like taxes and incorporation and all of that, and I'm sure there are other people out there, reading this, who will one day need to know the same things. I'll let you know. Give you a little walkthrough on how things go. Maybe you'll find my journey to be a nice map for yours.
I’ve been spending a good deal of the last two days preparing mentally for starting a whole new challenge as a developer. New things aren’t new to me, but this is different and big enough really call for some Deep Thoughts ™. For one thing, I’ve made a big move from the world of Python web development to totally other Python work and while web development has never been the only thing I do, it has been the only work that paid the bills. That transition isn’t one that bothers me or daunts me, though. Instead, I’m thinking about transitioning to the scope of the work I’m getting into. For a long time, I juggled multiple clients and client projects every day, so no single project usually took up most of my time. Every developer juggles time through the day, but exactly how that works in each company and on each project varies a lot. I was looking for a place that I could really focus in a way that I haven’t for a long time. I think I found that, but now I have to deal with the consequen...
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Be copious about this stuff. Figure out a system. Pretend like you're writing a manual for a chain of franchises - how does the work get done, how often do you bill, who does the billing, how do the records get kept...etc, et al, ie...
And finally (I should write a book), don't ever EVER EVERRRRR get more than $5000 behind in billing with a client. You can still take him to Small Claims court for $5K.
Good luck, but it's only 1% luck. It's more about staying fastidious and aware. People work for themselves because they think they'll be able to do MORE of what they love, but the opposite happens because you're busy running a business.
1) Build your system
a) Income - Outgo
b) Receipt and record storage
c) Quarterly tax $$$ awareness
d) Figure out insurance, etc.
e) Open a business bank acct
2) Meet with a few bookeepers. Try and avoid getting "Quickbooked". That program will break your spirit. Just find a bookeeper who will do it ALL for you. You'll be happier. I promise.
3) Realize that the new career path might destroy your marriage and/or relationships. It's scary trusting clients to pay you in a timely manner, when you have a family who relies on you to bring in the dough, it gets to be hard on the psyche.