Why I'm moving on from freelancing and getting a job.

Some valid points, I do freelancing in parallel to my regular job for the past 10 years and I can see that a lot of what he says are true.

But regarding: "You start wondering if your skills are deteriorating." I think he got that wrong. You can't imagine how much your skill-set deteriorates when you work at a company which has a specific set of tools you are allowed to use and everything is micromanaged by usually less than competent project management. If it wasn't for my freelancing projects I'd be stuck for the past 10 years with no new knowledge. What's worse is that sometimes you know that you can offer the client something better but for the good of the company its best that you don't - it makes you feel so bad in the end when a project finishes and you realize you didn't do the best you could because that choice was taken away from you.

I've been working for myself for almost a decade, so I feel this guy's pain. I have a few thoughts.

Marketing has to be treated like a software project: make it scalable. Drip campaigns, blog posts, and books all help with this. I once overheard a client say “People do business with people." These materials are to help you build trust with potential clients without investing in one-on-one time until you're fairly sure you'll have a sale.

One of the most effective things I've done in this area is to put a copywriter on retainer who "gets" our agency's voice. I can drink 3 coffees and bang out 4 paragraphs of technical jargon and she reworks it into pleasant, friendly copy, for a fraction of what my time as a founder/tech lead bills out for.

This isn't my idea by any means, Brennan Dunn covers it much more effectively in his book. [1]

NDAs suck. Agreed. I've never had a meeting that started with an NDA turn into work. Ever.

Guts are huge. I sometimes feel like Malcolm Reynolds in the pilot episode where he's double-crossed in the middle of the desert:

“I do the job. And then I get paid.”

One trick I stole from Million Dollar Consulting is offer a 10% discount for up-front payment. Maybe not the whole project, but, say, for each week or each month. I'm not saying 10% is chump change, but we're small enough that I'd rather have $9,000 today than $10,000.... 60 days from now (or never.) It eliminates a lot of risk.

On that note, retainers are awesome. I simply refuse to complete hourly maintenance without a pre-paid retainer anymore. No more "oh hey we need this 9 hours of work done by Monday" when I'm already scheduled for a full work week anymore. (Many thanks to patio11 for opening my eyes to this.)

"You do not get to grow with a team." This is the single biggest downside to working on my own, and one of the reasons I'm disinclined to leave Austin. I'm always the smartest technical guy in the room, and that is not a good thing (although it's certainly great for my ego.) To balance this, I try to be heavily involved in the Austin on Rails community. We meet up every Tuesday night and hack on stuff, and when I'm not sure about something, there are a lot of really, really smart guys who have been in software a really long time to talk through ideas with me. It's fantastic.

The other way I try to continually improve is teaching others. In between code reviews with my team or occasionally volunteering with MakerSquare [2] I'm forced to dive a lot deeper into the "whys" behind code. Having to explain concepts forces you to understand them really well.

Freelancing is definitely not all fun and games, but for whatever crazy reasons, I love it. The flexibility of scheduling and the ability to work directly with so many clients who are all doing great—and different!—things outweighs all the downsides.

[1] http://doubleyourfreelancingrate.com/ [2] http://themakersquare.com