Do You Work for Friends?

I have a policy on working for family members and close friends. Only small projects, and only for free. I don't let close friends and family members pay me. That may be kind of a radical position to take, but for me it works.

The reason is that people expect different things from business associates than from friends. A good friend is supposed to always be supportive. When a friend doesn't pay you back, you're supposed to show some compassion and let it slide. That's not how business transactions work, however.

I've found that when money starts changing hands, friendships get weird--and there's all sorts of confusion in the business relationship that isn't there when there isn't a pre-existing friendship or family-member relationship. That's because you're taking a friendly relationship and putting it in a business context--but the friend still expects friend-like behavior from you. In some cases, the friend will use that expectation to take advantage of you--either deliberately or subconsciously. This is why working with friends in a business context makes me nervous.

I am usually not OK with doing any of these things when working with close friends and family members. But I think if you do work with them, you may have to be:

You have to be OK with giving up-front advice. I usually take advice and criticism more personally from close friends and family members (some exceptions, of course) than I do from people I'm less close to. And most people I know are the same way. I'm aware that as a friend, I'd have to be quite a bit more tactful about giving advice on existing writing and tactics I don't think are working well for someone--and that can get in the way of clear communication sometimes.

You have to be OK with nagging for payment. The absolute worst-case scenario is when a friend doesn't pay you. This kind of thing can wreck a friendship. We're supposed to be compassionate with our friends--and if I see a friend is really struggling to pay me something they owe, my instinct is to let it slide. Indeed, in a lot of situations, I'd look like a jerk for pushing for payment. But in business, you have to make sure you get paid--regardless of the other person's financial situation.

You have to be OK with using a contract. Using a contract does imply, at some level, a lack of trust. Not so much that it can ruin a business relationship--actually, using a contract often improves trust with both parties, signaling that both are on the same page and want to do things above-board. But with a friend, a contract can say "I don't think you'll do what you say you'll do, so I'm holding you to it." That can make things awkward.

You have to be OK with saying no. Does your friend need you to work all weekend to meet a demanding deadline? Switch the scope of the project without paying more? Do endless revisions past your usual mark? As a business owner, I have no problem saying no to these requests. As a friend, it makes me a bit uncomfortable. Especially when I'm working with someone who knows me really well--and knows I'm just saying no to that weekend work so I can chill out at home, not for any long-held plans.

When I work with close friends and family, I keep the transaction solidly within a friendship context. No money changes hands--although a trade might be OK. And I keep the project small so it doesn't become overwhelming--no regular work for free. How do you negotiate working for friends and family?