On Collaborating The Smart + Kind Way

Now that Be Free, Lance (a workshop for freelancing that I co-founded) is coming to a close, I thought it would be a perfect opportunity to talk about collaboration. Because over the last three years, that's exactly what Jen and myself have been figuring out and perfecting in order to run our online community as smooth as possible. We've picked up quite a few tips, tricks, and resources along the way, all of which I'll share below. These will work well for any sort of collaboration between humans, and I'm going to dig deep, so here we go:


If you're partnering up with a good friend of yours on something big (a new business, project, etc.), you may not think that a contract is necessary because of your existing relationship. And honestly, this is the most common mistake, or oversight, that's made at the beginning of any collaboration. The excuse "but we're friends, nothing will happen" comes up a lot here, which is sweet, but not smart. And even though most people enter into a collaboration with the best of intentions, it's still a good idea to sign off on some sort of agreement.

Because even though you already have a good relationship, the last thing you want to do is come into an argument or misunderstanding down the road, and watch your beautiful collaboration suffer, just because you didn't have a contract to protect or guide instances like these. I'm being semi-dramatic here, but also not really. Working closely with another person is an intimate experience, one that's much different than the friendship you're currently used to. So please, get a contract. ;)

Now, this doesn't have to be a scary or worrisome endeavor. Simply express to your partner (or partners) why you think it would be a good idea, in a kind + light hearted way. Something like this will do: "Hey (Name), I'm so excited about our collaboration and think that we have a really good idea in the making. And even though neither of us intend for something bad to happen, I think it would be smart to write up a short and sweet agreement that keeps both of our best interest's at heart. What do you say?" Boom, easy does it.

When Jen and myself first started talking about Be Free, Lance, we didn't develop a contract or do anything official right away. But once things began to get serious, we purchased an LLC and attached a contract to it that basically outlined how our profits would be split, as well as who would do what. This is a pretty simplistic approach, which worked out fine for us. But looking back, we should have created something with a little more weight. For example, the following questions are ones that you should answer within your own collaboration contracts, at the very least:

— Who owns what (or is it joint)? — Who does what? — How will you split profits and get paid? — How will you handle disagreements? — What happens if one person wants out?

Now, if this isn't a simple collaboration, or if you'd rather be safe than sorry (!!), I would highly suggest hiring a lawyer to help. But in the meantime, you can hear more creatives jam on this topic over on the Being Boss podcast. They have an episode that covers contracts (and partnering up) in an honest way, making it a must listen for sure.


Whenever you start a new collaboration, it’s extremely important to talk about who does what so that everyone is on the same page. Assess each of your individual skills and assign different tasks so that the work is split up evenly. Or if you don't split things up evenly (which happens and is okay if agreed upon), make sure that each person is compensated appropriately for their time and efforts.

For example, I have more of a background in website development, so I handle a lot of the “tech” stuff that's related to the Be Free, Lance website. And since that takes time, Jen has stepped in to be the main designer for our website and marketing materials, which helps even things up. Beyond that, Jen also manages Instagram, while I focus on Twitter and email, since Twitter is less of a hassle than Instagram.

If you're looking to define roles within your own collaboration, try writing out a list of common tasks in order to analyze how much time they'll take. Then, you'll be able to easily assign things more appropriately between all parties. But even when you get specific like this, remember that roles can (and will) change.

To explain, let's take a look at another example. Let's say that you're in charge of managing Instagram, but discover it's taking you more time than originally planned. It's your job to then have an honest conversation with your partner to see how they can pick up the slack elsewhere. Or maybe you have a busy week and need help tackling some of your project to do's. If your partner helps, perhaps you take over some of their tasks during the next week. Long story short ... role splitting is fluid, and should be revisited often in order to keep things fair and everyone happy.


This is my favorite part, because systems are amazing and everyone should use them. SERIOUSLY though. At Be Free, Lance, we chose to keep things simple. But effective. Here's what helped us the most:

GOOGLE DRIVE One of the first things we did at the start of our collaboration was to create a shared Google Drive folder specifically for our project that we could both access. We then created new documents for each course topic, and began drafting content within. This was an amazingly easy way for us to simultaneously create content, simply because we could update documents at the same time and collaboratively edit through their commenting system. But most importantly, it meant that we didn't have to send Word docs back and forth through email, which was a major time saver. Ten out of ten would recommend.

* Google Drive also automatically saves past versions of all of your documents, so you can easily go back in time if something was accidentally erased or written over. Just another huge perk.

DROPBOX Jen and I were already synched up with DropBox for our own businesses, so it was an easy decision to use it for Be Free, Lance as well. We came up with a simple file structure ("Be Free, Lance" main folder with general sub-folders like branding, photography, website, legal, taxes, etc.) and haven't had to change anything since. So whenever I edit a file, Jen automatically has the updated version. Or if Jen creates a new folder and fills it with important files, I'll be able to see it as well. It's like magic and I can't tell you how valuable it's been. Even if you aren't looking to collaborate, try it out for your own business. It's THAT GOOD.

TODOIST So far, I've covered how to split tasks and seamlessly share files. But how do you create a plan and system so that all parties are aware of what’s happening at any given time? This is where ToDoist comes into play for us. Inside ToDoist, we have a specific folder for Be Free, Lance where we can list tasks, assign them to a certain person, and set due dates. We started off sharing timelines through email, which promptly got buried or lost, so this has become a serious lifeline! Now, we know exactly who needs to do what and when they need to do it by. And when a task is complete, we simply check it off and move on!

* There are a ton of other task management systems out there, so this will depend on what you need. ToDoist is great for it's simplicity, but if you're looking for something a little more in-depth, try out Asana. I'll have to share a whole post about this one in the future, since we use it for project management here at Rowan Made.


I've saved the most important topic for last, but it's actually really simple (and obvious). Always always always talk to one another. That's what collaboration is all about, after all ... working together to create something BETTER than what you could have done on your own. So if you're feeling like there's too much on your plate, speak up! Or if you don't think that somebody is carrying their weight, (kindly) SAY something. Open and honest communication is the backbone of a successful collaboration. And if you have that, you'll be ten steps ahead. ;)

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PS. Shameless plug time, but today marks the LAST TIME that we'll be opening up Be Free, Lance for registration. Ever. It's definitely bittersweet, but we're both ready to put focus on our own individual businesses and lives. So if you're interested in joining us for one last go around, head on over to our website for more details! Open enrollment ends on November 15th at 12:00am CST.