Personal chemistry is key, but even more important is clear expectations and intentions going in, though; once my first group ended, I tried with another, and it flopped miserably. It seemed that we had very different ideas for what it was all about, and it crumbled quickly.

If I ever go for it again, I’d be sure to get really, really clear on our purpose, responsibilities, and focus before getting committed. When it’s working, it’s fantastic.. but when it sucks, it sucks.

Great article. Really gets one motivated to get out there.

“not just telling your spouse”
Yeah, I sound like the biggest nerd on the planet when I talk about work.

“missing-link is to start a sparring circle of freelancers”
It’s not the same. Freelancers are always too “busy” and never want to leave the computer face. It’s not like hanging out in the bathroom stalls together talking about an annoying phone call or going to lunch and sneaking a cocktail.

[#4 is missing its boldness.]

I don’t think this would work for me when it comes to freelancing, though I do like and encourage small work groups for creative writing; it keeps writers on track and allows important feedback in a safe environment. Freelancing… I don’t know. It’s still solitary for me, it’s a different beast.

The only thing I could think of is for a bunch of freelancers to rent an office space together, then you could get that bathroom / kitchen / copier chatty environment that we oddly miss, while still being your own boss.

@Martha: Good points there. Of course you have to do what works best for you. For our group, the sparring has been crucial in developing fool proof marketing strategies for each of us, as there’s been a critical viewing point on every idea. And your right about the commiserating While a little wenting is ok, that’s exactly the reason I encourage people to make an agenda and set an exact time frame for the meetings.

1. It takes time away from more important things like contacting potential clients and staying in touch with the best of my existing clients. While it’s nice to have a a caring circle of other freelancers, they’re not going to keep me in business the way paying clients will.

2. They can turn into commiseration sessions in a hurry. While it’s nice to let off steam once in a while, it’s better that this doesn’t turn into a major life activity.

@sean – nice work spotting the missing header tags. I had to take a second peek after seeing your comment before noticing. You’re a quick one!