Ok, there are likely more than 5 ways, but here are some really time-tested methods for screwing up as a freelancer.
1. Be disorganized.
Ever lose a timesheet with 50 billable hours on it? Lose notes from a customer phone call or a design session? Clients want you to be more organized than they are. Don’t let your inner slob out.
2. Annoy the customer.
Customers can be completely infuriating sometimes with unreasonable requirements, curt e-mails, idiotic support requests, and such. You feel completely justified yelling at them. Don’t. You’re getting yourself caught up in your personal feelings instead of focusing on being helpful to the customer. Want to keep customers for a long time? Learn to play on the same team all the time.
3. Be invisible.
What’s worse than being a pain in the ass? Being completely invisible! If customers don’t know where to find you, don’t know that you exist, don’t know whether the project is on time or late, have no idea what services you offer, don’t remember that you’re there to help them when they consider their next business expansion… you might as well hang it up. Stay in touch with clients during and check in once in a while after the project ends. Work on your client marketing every day until you have a backlog… and then work on it some more until you can hire a subcontractor for some of the work you don’t want to do. Then work on it some more.
4. Play politics.
Two managers at your client’s office are in a political scuffle and you think one of them is right and the other is a jerk. Here’s a really great recipe for failure: pick sides. No matter who wins, you’re guaranteed a one-way ticket out of there. Never ever ever ever get involved in customer politics. Keep your opinions about employees at your customer site to yourself unless the boss asks you about an underling and even then hesitate until you feel your arm being twisted out of its socket.
5. Act like it’s not your problem, even if it’s not your problem.
One of the underlings at your client screws up the project and you want to just throw up your hands and let him fix it. Bad choice. The client isn’t paying you to let failure happen. The more helpful you are to the person paying the bills, the more bills they’re likely to want to pay. Be proactive about problems, warn the customer of risks before undertaking a path, basically look out for the customer’s interests and the customer will make sure your invoices keep getting paid.
Got other ways to screw up? Add a comment and let everyone know.