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Switching from full time programming to 1099 contractor?

Hello all,

I wanted to get other software developers' thoughts on what I was thinking about doing. Just a little bit of background ... I'm 29, have a B.S. in Computer Science, have around 7 years total experience in software development (primarily C++ programming but comfortable with C, Perl, and C# as well). I work in the finance industry in Chicago. I am single and have several months of emergency savings in the bank (which I know is a must for contract work).

Based on what I have read (and it's hard to find topics about this), it seems like I would be a good candidate for contracting work. I have actually done some side contract work in the past for various clients and they were all happy with my work. The problem was that I didn't feel like I could make enough money to maintain the lifestyle I have right now with my permanent job. I was getting work through sites like ODesk.com or Craigslist. I found out that it was hard to compete with people who were willing to do the same work for much less money in other countries, but I still managed to find a few decent gigs and probably could've developed a good client base given time.

Ideally, I would like to do that sort of thing full time except not necessarily though ODesk.com but through contacts I develop over time. I also recognize it's quite risky and for sure I wouldn't be making enough money for the first several months if not longer. I know what it was like to deal with clients who don't pay you on time or ever pay you period. Based on what I have read, working on an IT contract for a 6 month - 2 year period at some company basically feels like you're at a permanent job, but at least you'll have some flexibility and move on to another contract if you don't like the current one. My plan is to initially take on these 6 month - 2 year type of contracts for a while until I develop a good client base and then after that I can become more of an actual "independent" contractor that does whatever work I want to do whenever I want. I understand that I have to develop a good client base first though.

My first question is: Does it make sense to do what I am thinking about doing? Secondly, how do I get there? Should I just search for a contract job on a site like Dice.com and go from there? I found my current permanent job on Dice.com. Am I completely nuts to even think about this? What are your thoughts?

Caldus Send private email
Saturday, June 28, 2014
You might want to checkout the site/ebook by Brennen Dunn, "Double Your Freelancing Rate". Might give you some ideas.
M.B. Dude Send private email
Monday, June 30, 2014
@ Caldus: "move on to another contract if you don't like the current one. "

Unless you have a *very* good reason, don't ever do this. Think of your next interview/potential assignment: "Why did you leave XXX? early?", 'Didn't like it there', "OK. Can we get a reference", 'Erm.... no.'

If you want to be a serious contractor you need to keep the clients happy and, more importantly, keep colleagues happy. People have a habit of moving around and walking out of a contract will mark you down when they move to YYY corp and remember your name/company when a cracking job comes up.
Ewan McNab Send private email
Monday, June 30, 2014

That's definitely true. I didn't mean to say that I would walk out of a contract early like that. I meant to say that I would have more flexibility with things in the sense that once the contract was over, I could move on to something new if I wanted to.

I was searching around on different job sites and the best rate I've found in my area for a C++ contract is $90 an hour (they claimed it started at that rate). I'm not sure if it was a W2 or 1099 contract though, so that could make a difference. Of course, most jobs just say the rate is "Competitive". It was crazy to see a lot of contract jobs in my area paying $45 an hour or something like that. I guess this is why it's important to develop a good client base.

It's just difficult to really measure the risk in this sort of career change. I guess it's because I'm so used to the stability of a full time job. It also seems like C++ is becoming a lot less prevalent out there these days, so I may have to adjust to new technologies.
Caldus Send private email
Wednesday, July 02, 2014
I did exactly this at the end of last year. 

I had been doing side contract work for several years, and had wanted to do it full time, but the risk was too high - I'm the sole breadwinner for my family, and due to some health issues in the family it's very expensive (or impossible) to get good medical coverage without a group policy.

However, I got laid off from my F/T gig last year, at the same time I had a P/T contract project spin up.  I decided that I would focus on that for a few months, trying to pick up some additional side projects, and see how that worked out.  The ACA went into effect in January, meaning that I could afford to buy decent medical insurance.  Since then I've managed to pick up enough work to make it feasible to continue.  Due to what I assume is dumb luck, I've had enough substantial multi-month contracts to keep me busy without having to go the odesk/elance route (although I do keep my eye on those just in case). 

Right now my goal is to go a full 12 months, evaluate where I'm at, and decide if I want to continue.

My biggest concern is keeping the pipeline full so that I don't have a substantial break between projects.  Beyond that, it's the usual stuff

  - raise my rate
  - spend more time building the business/brand
  - develop some product ideas as another revenue stream
  - re-evaluate my tax/legal setup

Feel free to PM me if you want to discuss anything in more detail.
Jason Send private email
Thursday, July 03, 2014

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