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Guide

How to join forces with a creative collaborator

A guide to bringing projects to life collaboratively by Shannon Byrne, with illustrations by Emily Haasch.
Prelude

As someone who spends almost all of my time working on creative projects—either for myself or for clients—collaboration has been a consistent cornerstone of my career. Despite all the practice I’ve had teaming up with others to bring new ideas to life, giving up creative control on projects has always been a struggle. It’s taken time and practice to truly discover the beauty of having a creative partner to lean on for support and accountability, to brainstorm with, and simply to get things done more efficiently. But over the years, I’ve learned that it’s way more fun to let a project unfold as the product of two (or more) brains, rather than just my own.

If you’re looking to bring a new idea to life, there are many reasons why it might make sense to team up with a collaborator. In this guide, I’ll share takeaways from my experience collaborating with my friend Hannah Spencer on The Process, a podcast exploring how to survive as a creative person. We’ll cover when a collaboration is most beneficial, finding the right person to work with, managing the collaboration for success, what to do if your partnership goes awry, and things to consider for the future.

Shannon Byrne

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Guide

Why collaborate?

Working with a collaborator can make an ambitious passion project more feasible, sustainable, and fun than it would be if you tackled it alone.

How to know when to collaborate

Of course, there’s nothing wrong with tackling a project solo. There are a bunch of reasons you might want to retain complete creative control over your project, and thus work on it by yourself. Some common examples are:

  • If your project is personal in nature
  • If it requires you to retain complete control for any reason
  • If you’re treating it as a hobby and it’s for you and no one else
  • If you want to pick it up and put it down whenever, without having to answer to anyone
  • If working on it gives you some necessary alone time

I first started working on The Process by myself. At the time, I had been managing 45 volunteers for another project and, to be quite honest, I was burnt out on working with other people. As I got started with The Process, I worked on it when I felt like it, and wasn’t necessarily concerned about consistency or how it’d all turn out. And, while I’m not a designer, I created all the initial branding myself (it was pretty terrible, but got the job done). This solo approach worked until I was ready to get more serious about it.

When I decided to take The Process to the next level, I knew I needed to find somebody to team up with to make the whole project more sustainable (and fun). This is an important thing to consider when working on a project: where are you hoping to take it? If you’re interested in growing a project beyond your personal network, if you have limited resources to reach your goals, or if you don’t have all the skills necessary to get a project off the ground, working with a collaborator could be the way to go.

Working collaboratively can help give a project structure

I’ve taken on big, audacious side projects by myself—even though I really could have benefitted from working with a collaborator. There were times when I was too stubborn or scared to ask for help, and times when I struggled to translate my idea into something others would be excited to get involved with. These situations often resulted in exhaustion, a lack of focus, and, worst of all, lost motivation.

I’ve since learned how to partner with people as a way to create the structure needed to bring ambitious projects to life. Having someone to talk things out with can be a saving grace for a project, especially when you don’t know exactly how it should develop. Plus, sharing responsibility for a project adds a layer of accountability in several ways. For one, collaborators keep each other in check, ensuring the other is moving things forward. They can and should also hold each other accountable to meet deadlines, manage their time well, take breaks, and (when needed) spend time away from the project.

Collaborating can nurture your creativity

When you have two people working together on a project, it can be a lot less draining. As Julia Cameron alludes to in The Artist’s Way, our creativity is a finite resource. Each time we do something that takes creative energy, we drain our creative well a little bit (or, in some cases, a lot), and need to find ways to fill it back up. Splitting up responsibilities means draining your well less, which leaves you more energy to pour into your day job or other projects. Plus, having someone to communicate with and bounce ideas off of will ensure you’re keeping your creative well filled up with new ideas, sparks of inspiration, and fun.

Most importantly, the happiest collaborators I’ve witnessed provide each other with emotional support. If a project becomes overwhelming, your collaborator is there to bring you back to earth. It’s also nice having someone to share success or pain with—when you’re in it together, the ups of a project become more pronounced, while the downs become more manageable.

Working collaboratively can help you do more, better

Most obviously, a collaboration should bring a complementary skill set to a project. Let’s say you want to build an app but can’t code. Or you want to publish a children’s book, but illustrating (or writing) isn’t your strong suit. Bringing on a collaborator with a complementary skill set allows you to create and launch a project without hiring someone right off the bat. Plus, having a partner who’s equally invested in the project’s vision means they’ll be creating work that’s aligned and consistent with the project’s overall goals, both at the project’s start, as well as into the future.

Note: Partnering with a collaborator means loosening your kung fu-grip on your vision. If it’s a true, authentic partnership, you’ll no longer be the only person calling the shots. Note that it will be important to sit down with your collaborator and talk through where you both see the project going. Outline your mission, vision, and goals together. Be open to feedback and ready for change until you find what works for both of you.

For The Process, I do the interviewing, editing, writing, production work, and distribution. Hannah manages the design, website development, branding, and creative direction. We both make timelines and editorial calendars, brainstorm messaging ideas, and generate guest suggestions for upcoming shows. It’s a great marriage of skill sets and approaches. As we’ve developed our own collaborative process, we’ve taken bits of what’s worked for us from past experiences and brought them together to create systems that flow smoothly for us. I’m also always happy to give up an old process up if Hannah comes up with a better way to do it—and I think this type of flexibility is key to making any type of collaboration work.

Thanks to our collaboration, The Process is no longer just the Shannon show. Because of this, it feels like one day it could be bigger than the both of us. Now, rather than thinking about what I like or want, we think together about what’s best for the audience we’re both passionate about serving. In my opinion, this melding of minds has helped us to improve the show and its messaging tenfold.

Working collaboratively is a great way to branch out

Without a doubt, working with a collaborator can instantly bring increased awareness and exposure to a project. Your partner doesn’t even need to be a celebrity or influencer to increase your reach; two small or large networks are better than one, and more diverse than one. Teaming up with someone will enable you to cast a wider net with your project, and will also help to bring new perspectives and feedback to the table.

Finally, working with a collaborator can make trying something new less scary. Even if you’re both beginners at whatever it is you’re doing, you’re in it together. So whether or not your project pans out in the end, you’ll still have worked on something with a friend (old or new), and that’s pretty fun to think about.

How to choose and vet a collaborator

Once you have the desire to team up with a collaborator, it’s time to think strategically about who you can bring to the table. I believe that the best collaborations happen naturally. More often than not, knowing who’ll be a great collaborator comes down to having “a gut feeling” about someone, to following your intuition, and to following clues from the universe.

Have you ever been in conversation with someone and felt that rush of excitement as you see them getting stoked about your new idea (or, you getting stoked on theirs)? Or, you might start riffing off of each other’s ideas until you have some brand-new idea on your hands—a product of your two brains working together. In as simple as a few magical moments, a new collaboration can be born!

Hold up for a second, though: don’t let things develop too fast. Once you feel like you’ve found the perfect project idea and collaborator, you now have some vetting to do. Even if someone has been your best friend since childhood, that doesn’t mean you’ll work well together, or that they’ll be able to hold up their end of the collaboration. Creative projects will ebb and flow, and it’s important to work with someone who can roll with the punches, and who will encourage you to do the same. On the flip side, it’s crucial to find someone who you can trust, and who will follow through on what they commit to doing.

Before jumping head-first into a project with a new collaborator, here are two key things I always recommend doing:

  1. Get to know them better by asking a lot of questions (directly and indirectly) about their working process, communication style, values, interests, and motivations.
  2. Kick off your collaboration with a small-scale “test” project. (You don’t have to tell your collaborator it’s a test—you can just frame it as a natural precursor to what might come next.)

In my experience, these two things can happen hand in hand. Working on an initial small-scale project will give you an opportunity to try working with your potential collaborator, and to get a sense for what your chemistry is like. Plus, it’ll give you time to ask them questions and suss out their working style, how much time they have to commit to a new project, and where they’d like to see a future collaboration going. Your pilot project could be a prototype, a meetup, a poster design, or something else that’s relatively quick to produce—it just needs to give you a chance to try working together before committing to a larger collaboration.

Before you start working on the pilot project, think of some questions you might want to explore with your collaborator. That way, you’re more likely to pay attention to small nuances in your working chemistry that could play a larger role down the road.

When working on a pilot project with a new collaborator, some of my favorite questions to think about are:

  • How do they organize their work?
  • How do they manage deadlines?
  • What tools do they use?
  • What have their collaboration experiences been like in the past?
  • How much time do they have to commit?
  • Does the work they’re producing feel like a match for the project?
  • Are they open communicators?

These are just my personal examples. What matters to you? How important are someone’s personal values, taste, or working habits? What’s relevant to the project at hand? Ask and observe these casually and quietly over time. Note that if you drill your new collaborator, you may scare them away.

Starting with a small-scale project: A personal story

Last winter, I took part in a program called Art of Freelance to explore turning The Process into a magazine—which I was excited to jump in on, but wary of tackling without first finding a designer to collaborate with. At the same time, I happened to be getting drinks with my (then internet) friend, Hannah. As I was telling her about this “crazy idea” for a magazine version of The Process, her face lit up. She responded with “let’s do it” before I could even ask her if she wanted to help out. An immediate wave of relief came over me.

As part of the Art of Freelance program, we had the opportunity to have a booth at a showcase and to present the project to about 100 people—which turned out to be the perfect small-scale project to work with Hannah on. We had a few weeks to come up with a website, presentation, and an interactive piece—and boy, did we pull it together quickly. During this trial project, we worked together so seamlessly that there was no doubt in my mind about making the collaboration more official and long-term.

Where to find your collaborator

If you don’t already have someone in mind—say, a friend, a colleague, or a former coworker—ask your creative friends if they know anyone who they think would align with what you’re looking for. If that doesn’t work or feel like an option, try talking to people at meetups, relevant events or conferences, parties, or even in coffee shops. Talking with lots of new people about your project idea is the best way to put out feelers and find other people who are as excited about it as you are.

If IRL networking gives you anxiety, you’re not alone. Instead of talking your idea up with strangers at events, you could seek out relevant Facebook groups or other online communities with active participants, and look for people there. This might sound like a longshot, but it’s not—my friend Sarah just wrote a nonfiction book with someone she met in the Creative Ladies Collective Facebook group.

You can also look for potential collaborators on Twitter or Instagram, by searching for and following people whose work seems like it might align nicely with yours. If, after following them for a while, you feel like their projects and approaches are in line with what you’re hoping to do, you can reach out to them to see if they’d like to meet in person for a coffee to hear more about your idea, or just to get to know each other.

Keep an open mind as you meet new people. Pay attention to who lights up when you talk about your ideas, or whose ideas or style gets you excited. Try not to put too much pressure on finding someone right away. Forcing a collaboration is a recipe for disaster. Practice patience, and aim to build new relationships (or, ideally, friendships) slowly—then, if a collaboration starts to make sense, you can bring it up as a friend rather than as a stranger.

Set your collaboration up for success

Get on the same page

While formalizing a collaboration or project with a rigid structure or set of expectations could make it feel like a job-job, setting up lightweight processes and expectations can go a long way.

Work with your collaborator to define what the project looks like through both of your eyes. Specifically, you can collaborate to answer the following:

  • Define the project’s scope (How big will this be? How much time will we each be able to spend every week or month?)
  • Articulate your goals (Why are we doing this? What are we trying to accomplish?)
  • Lay out roles and responsibilities (even if these are vague or broad to start, it’s a good idea to articulate who’s doing what)
  • Share what resources you have access to (whether you have extra time, tools, funds, other talent, or a network—lay out what you can each chip in)

Essentially, use the above questions to make sure you’re on the same page. It’s fine if one person has more ambitious expectations for the project—it’s just important for you both to be aware. This will help prevent potential resentment or guilt if one partner puts in more work than the other.

Lay out a work plan and set some boundaries

As you get to work, keep each other in the loop on when you’ll be working on the project and when you’re available to talk about it. Loosely determine what tools you’ll use to collaborate (email, chat, Google Docs, a project management software like Trello or Asana, etc.), and when you’ll collaborate (nights, weekends, early mornings, or…?).

This is also a great time to schedule a cadence for check-in meetings, so you can update each other on progress (or lack thereof) and continue to plan into the future. This may feel like overkill, but I suggest creating these sorts of minor organizational systems up front. Side projects and new endeavors can get out of control quickly—or, just as quickly, they can be forgotten about. Decide how often it makes sense to check in with each other, and plan how you’ll organize your documents, to-do lists, timelines, emails, passwords, etc.

I recommend treating the project management side of your collaboration how you would a paid job. It will make things easier for both parties, allowing you to focus on the fun part of creating when you’re together (in real life or digitally).

The idea with setting up these structures isn’t to make your collaborator feel watched or managed—rather, it’s to build transparency and accountability. When you both know how much you have to give to the project, you can keep the collaboration flowing without getting bogged down wondering what the other person is thinking, feeling, or stewing over.

With any new collaboration, setting boundaries is also crucial. This step often requires some trial and error. For example, if your collaborator is texting you all day when you’re working at your day job, it’s up to you to set boundaries, and vice versa. Just remember to always be kind, considerate, and open when giving constructive feedback or laying down some ground rules.

How to manage and sustain your collaboration

It’s worth repeating: going slow with a new collaboration will help you navigate unfamiliar waters. Setting goals and a plan for how you’ll accomplish them is great—just be sure to keep them realistic in order to keep the project feeling enjoyable.

Check in on emotions

As you move forward with your project, remember to check in on the happiness levels of yourself and your collaborator once in a while. Use your intuition. If you start to feel less into it, or if they suddenly seem to lose steam, approach it with them directly and kindly. I often ask my collaborators, “How are you feeling?” This question is broad enough to give them space to air any concerns or express how satisfied they’re feeling, either with a specific thing they’re working on, or with the project as a whole.

Do the same for yourself. Pay attention to how you feel about the project and the collaboration. If it’s draining your energy rather than adding to it, something is off and it’s time to reassess and make a change. Try keeping a journal to track the highs and lows—this will come in handy in tuning in to what’s working, and what needs to be adjusted.

Evaluate progress and adjust accordingly

Use your scheduled check-ins to look back at your goals and what type of progress you’ve made. Did you try to tackle too much? Do you always feel “behind?” Does your vision still align with your shared interests and values? There’s no shame in adjusting your goals or overall plan to be more realistic and better aligned with you and your collaborator’s lifestyles and other things going on.

Have fun!

If you and/or your collaborator are feeling drained, reassess your workload and plan some fun time for the two of you. Go on an outing to a museum or the beach or a lake. If you live in different places and can afford it, visit one another and be sure to have at least one non-work afternoon or morning.

Side note: I visit Hannah in LA as often as I can, and it always results in an epiphany or getting a ton of work done in a short period of time (and sometimes dancing, too).

What to do if your collaboration isn’t working

Pinpoint the issue

Ah, the hard part. If it feels like your collaboration isn’t working, try pinpointing where the issue lies and why. I typically start by coming up with my own hypothesis, then having an open conversation with my collaborator to see if they’re feeling the same.

First, I ask myself questions like: What can be changed or tweaked for the better? Is it a communication issue? A time issue? A commitment issue? I find journaling these out with a pen and paper particularly enlightening. Then I ask for a casual meeting to explore these questions together.

Brainstorm solutions to test

After pinpointing the underlying issue(s) together, I suggest brainstorming solutions to test out. For example, if one of you is having trouble with your workload, an option might be to scale back that person’s role or set of responsibilities. Another solution might be to bring on an additional collaborator to help with the workload, or to scale back the project so it becomes more manageable. It all depends on the issue at hand.

If those changes don’t work, or if the partnership seems beyond repair, it’s time to have a tough conversation. Don’t fret, it won’t be nearly as bad as you think it will be.

How to have a constructive conversation

If you need to have a hard conversation with your collaborator, approach the topic softly but directly and honestly. As with any tough conversation, stick to “I” statements and avoid using any accusatory language that might cause the collaborator to get defensive. Focus on what’s best for you, them, and the project as a whole. Make sure they understand it’s not personal, but something just isn’t working for you. Be open to exploring their feelings about the issue, and be sure not to cast blame (as hard as it is to resist sometimes).

If you feel that you truly do need to hit pause on the collaboration, you could say something like this:

“Perhaps it’d be best if we hit pause on the collaboration for now. I’d love to keep you in the loop. Maybe we can explore how you can get involved again in the future?”

Another option is to ask them how they think it’s going. This allows them to start the conversation so it doesn’t feel like an attack. In all likelihood, they’ve known something isn’t working, and haven’t known how to approach it either.

“Hey, I don’t know if you feel it too, but something seems off with this project. It doesn’t feel like it’s working as well as it was. What have you been feeling? What do you think it is?”

When it’s not about the collaboration

If the issue is less about the collaboration and more about the project itself, then have a conversation about what to do with it. If it feels like there’s no way to save the project, then explore a fun way to end it—go out with a bang. Make it a celebration! Or maybe the best route is a slow dwindle. Agree on something, make a plan, light a candle, and reflect on everything you’ve learned and accomplished. Then go buy yourselves a brownie or a beer or something.

These are hard conversations to have, but they’re also incredible growth opportunities. By facing issues up front, everyone will benefit in the long run. Remember: it’s critical to listen to your intuition when it’s telling you to run for the hills. Don’t try to make something work just because you like someone’s style, or because you really thought it would work out in the beginning. When you can tell something isn’t working, you’ll feel it in your body, and that’s when it’s time to take action.

Considerations for the future

Sometimes, projects we’re passionate about turn into something bigger. How fantastic! If you feel that happening, consider taking your collaboration to the next level by building some formality around the partnership.

What happens when you start making money?

If your project starts to develop some legs and income becomes a possibility, it’s important to have a conversation about managing revenue. When your project earns money, will you split it? Or put it all back into the project? Maybe you’d both like to pay for an assistant, or invest it in marketing? Try to lay these desires out on the table so that when you suddenly have someone writing you a check, it doesn’t create a point of tension.

Another thing to consider is who owns the copyright to the work you’re both producing for the project, and how that work should be treated. For example, if you’re creating something with intellectual property (hint: you probably are), who can reproduce it? What happens if you sell it? What if one of you wants to take everything you’ve built and turn it into something else? While you probably don’t need to hire a lawyer while you’re in the early stages of thinking these things through, having a lightweight strategy in place for the more business-y sides of your project will help ensure that you and your collaborator are both on the same page.

Using contracts can protect all parties

If your collaboration starts to feel more like a co-owned business, you’re definitely going to want to create a contract outlining all of the above details, plus what happens if someone leaves the partnership, etc. Talk to an attorney to ensure everything is on the up and up, and that you’re protected. Other things to consider if things are getting serious are brand standards and guidelines, who you may want to hire to help out as you scale up, and how to set yourself up as an LLC or other type of formalized business.

Don’t put the cart before the horse

One final thought: Take things one step at a time. I’ve made the mistake of spending time and money talking to attorneys, worrying about contracts, establishing an LLC, and more—all before I was ready. While I was worrying about all these administrative hurdles, I wasn’t sure if I was working on a side project or a business. Getting nitty-gritty obsessed over business-related details was ultimately a distraction from our core challenges as project collaborators. So: don’t put the cart before the horse, and stay tuned into your priorities. As long as your lines of communication are open, the rest will follow.

In summary…

Working collaboratively is an excellent way to bring a creative idea to life. Collaborators can bolster a project with new perspectives, skills, and audiences. But like anything, partnerships take thoughtful nurturing to develop and grow. So do your research, start small, communicate often, keep checking in with yourself and your partner about how you’re both feeling, and go with the flow. Good luck!

About the Author

Shannon Byrne

Writer, Producer, Strategist

Shannon Byrne is a writer, editor, producer, strategist, and podcaster. She works with small businesses, creative entrepreneurs, startups, and activists to help them get their projects off the ground and discovered by the right people. She created The Process, a podcast exploring how to survive as a creative person, which she now runs with her friend Hannah. Shannon also founded A Song A Day, which curates song recommendations from humans, not robots. She has produced concerts benefiting Planned Parenthood, ACLU, and Arts for LA.