Thoughts on Freelancing

Now that the holidays are over, I’m looking forward to rocking out on some new projects in 2011!

In April, I will have been freelancing as a web developer for four years.  Kinda scary to think that I didn’t have a stable paycheck every two weeks or employer-paid health insurance during this time.  And when times are slow, there’s that sinking feeling that creeps in: am I going to have to go back into the “real world” and get a “regular” job?

But, some of the things that I do love are:

  • flexible schedule and free time
  • working remotely from ANYWHERE (with an internet connection, of course)
  • sleeping in and working the hours when I’m most productive
  • not dealing with morning/evening rush hour commute
  • working in a T-shirt and sweats :)

Over the past few years, I’ve learned a ton… web/tech/geeky stuff, how to setup/run a business, dealing with difficult clients, but most importantly, being able to manage your time effectively to get sh*t done and still have some time to play.

I’d keep up with new job postings just cuz ya never know when work will dry up, but also to see what skills/technologies companies are hiring for.  If you’re looking for a tech job, make sure to post your resume on,, and  Setup weekly job alert emails on  Setup your professional network on LinkedIn.

People will probably doubt your decision to go freelance-style.  It’s definitely much easier if you do not have a family to support or maintain an extravagant lifestyle.  Not having a stable paycheck actually forces you to budget better and think about your expenses, knowing that you’ll need to cover mortgage/rent, food, and bills.

So, how did I get started?

I setup an LLC through to keep my business liability separate from personal assets.  Fill out some paperwork and they take care of all the documents and filings that you need to setup business in your state.

I bought health insurance through — when I resigned from my job in 2007, I had the option of purchasing COBRA for $400+/month.  At the time, I ended up purchasing a plan with Care First Blue Choice for  ~ $118/month.  Since then, it’s gone up about $100 extra per month, so I’ll probably be checking out other health plans soon…

I setup a self-employed 401k plan with Fidelity.

I setup my home office.  Painted the walls w/ Behr’s Eastern Amber for a sunny work environment :)

More later… go Ravens!

Filed under: Uncategorized | Posted on January 15th, 2011 by Jan

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