Sign in Sign up
Friends as side hustle clients? Here's how to prevent them from becoming foes

Friends as side hustle clients? Here's how to prevent them from becoming foes

What are friends if not the people you’ve been networking with the longest?

Just kidding. But the reality is that friends are a part of your network and can be invaluable resources to help grow your side hustle. Whether it’s introducing you to your next client or being your next client, friends are a freelancer’s greatest resource.

That doesn’t mean that making the transition from pals to, well, something more is easy. Like the other kind of something more, it can be awkward, emotional, and friendship ending. But it doesn’t have to be.

How to set up your new professional relationship for success

Here, we outline the four steps to ensuring that your new professional relationship doesn't tarnish your personal one.

Step 1: Get ahead of financial discussions

If I have some time and you are a friend, there are a slew of things I’ll do for free. Wedding websites, personal websites, speeches, resumes, proofreading, general editing – it’s all fair game. If you’re a really good friend, I’ll even help with branding your business for free. But my rule is that it’s one off and I will not be doing rounds of edits. Will I accept a round of drinks as payment? Sure, but I don’t expect it.

For anything else, I charge. And I charge my regular rate. I don’t play with discounts. You’re either hiring me or I’ll do it pro bono. Anything else gets too complicated and sets someone up to feel resentful.

While we’re here, if a friend is doing something for free that they usually get paid for, the polite thing to do is send a gift. I recently had a friend work on my website for me and she refused to let me pay her. So instead, I sent her a nice plant and donated my day rate to an animal shelter by her house (she’s a real dog lover).

Step 2: Expect a change in dynamics

Working with or for a friend will be different than just hanging out. It’s like when you hear someone’s telephone voice for the first time. You recognize them, but there’s something a little weird about it. You’re learning about a new facet of your friend’s personality and that might take some getting used to.

Also, the power dynamic in your relationship will inherently change. Getting critical feedback about my work from my friends can feel bizarre, but it’s part of the deal. That’s also the reason I charge my normal rate – I expect there to be normal feedback and a normal refining and editing process.

Navigating a difficult professional conversation | Polywork Blog
Here’s 4 tips for navigating a difficult professional conversation.

As with most things in life, communication is key here. I recommend establishing from the get-go that you expect feedback and your friend shouldn’t feel apprehensive about giving it. Like any client relationship, you have the same goal – doing what’s best for the business. Even more so because it’s your friend’s business!

Step 3: Set your boundaries

Your friend probably has your cell phone number. That doesn’t mean they should use it to talk about work. It’s important to be able to be clear about when you’re talking about work and when you’re talking about normal friendship things.

It might feel weird at first, but compartmentalizing friendship and work does become second nature.

For me, texting is personal and email is professional. If my friend-client uses text to talk to me, I’ll usually say something like “Hey, would you mind sending this to my email? I like to keep everything related to a project in one place so nothing gets lost.” Then I don’t have to explicitly say, “Stop texting me about work.” But if they kept doing it, I would. And then I’d say something completely unserious to set the precedent of what this channel is used for.

It might feel weird at first, but compartmentalizing friendship and work does become second nature. I have a friend who has been a client for five years. We can be having a very serious (even tense!) back and forth over email and then a completely different conversation about weekend plans or the latest shoe sale over text. At the same time. Being diligent about keeping modes of communication separate is what makes it work.

Step 4: Expect the best, but plan for the worst

The best way to prepare for the possibility of things going bad is to discuss a plan while things are still good. In that time when you both have the most grace and goodwill, I highly recommend giving each other emergency exit plans and instructions on how to use them.

I recently started working with a friend who is starting her own business. It’s really new, so it wasn’t clear how our partnership was going to work exactly, what she would need, or how our styles of working would mesh.

The best way to prepare for the possibility of things going bad is to discuss a plan while things are still good.

While I was so excited for her and happy to help (and earn that sweet side income), retaining our friendship was, and still is, important to me. So I gave her a script to use if she felt like she needed to end the working relationship. She is allowed to use it at any time and there will be no questions or hard feelings. This is the script:

Hey Lori, we have to have that awkward conversation. I love you, but I need someone with more capacity to really flesh out this business with me. Thanks for helping me get to this point.

She gave me a similar, equally euphemistic script. And while we haven’t had to use them, it’s comforting to know our outs exist.

Final thoughts: It's business, not personal

You followed all of the above steps and it still didn’t work out? That’s tough, but it happens. Breaking up with a freelance client is always difficult. Doing it when they’re your friend? Torture. But sometimes it has to be done. Just like some friends don’t make compatible roommates or travel companions, some friends just don’t make compatible professional partners. That’s ok. Even if it feels like it’s personal, it’s not. There was a reason you were friends in the first place. Nine times out of ten, it’s just about the way the two of you approach or prioritize work.

So how do you get out of the business relationship? My number one tip is (and if I could scream this, I would) do not do it in writing. Unless it’s gone really south and you’re worried you’ll get overly emotional or say things you’ll regret, you need to do this face to face. You’re trying to move this relationship from professional back to personal, so having this conversation in the most personal way is key.

After you have the tough conversation, give them time. But as the person who initiated the professional break up, it’s on you to set the tone for how you now relate to each other. I would wait a week or two and then text them to hang out. Relax, have fun, just maybe don’t talk about work. At least not yet.

Further reading

Here are more resources for navigating the friend/client dynamic:

Difficult Conversations by Douglas Stone, Bruce Patton and Sheila Heen

Thanks for the Feedback by Douglas Stone and Sheila Heen

Nonviolent Communication by Marshall Rosenberg

• Harvard Business Review’s “What To Do When You Become Your Friend’s Boss”

Showcase your freelance side hustle in Polywork – get started here.