Got a burning desire for a freelance side hustle? You’re not alone. A lot of freelancers use side hustle projects as a way to add extra fun, income and challenge to freelancing.

To get a freelance side hustle happening, fellow freelancers often consider collaborating. In a lot of ways, it can make sense to collaborate. It doubles your audience reach and gives you the ability to strengthen your business offering.

A man holds up a card that reads take a walk on the wild side with impossible underneath. Could this be your call to action for a freelance side hustle or collaboration?

Photo via Unsplash by Markus Spiske

Choosing to collaborate on a freelance side hustle means looking at what you both bring to the table. You may share complimentary skills. Or it could be that you want to share an audience to bring a new side of your existing businesses to light. Such situations might be two copywriters teaming up to teach workshops and courses on SEO and content.

It could be a case of working together on marketing like podcasts or social media Q & A. It helps to strengthen your position of authority and increase your brand awareness for your respective businesses.

And sometimes, it’s a case of two freelancers brainstorming ideas or looking to solve issues within the industry or for our clients. You see is a hole in the market with a product or service and come together to launch something new. This is common when freelancers reach a certain level of maturity in their business. When you’re looking for less face-to-face client work, these kinds of partnerships and freelance side hustle projects can help you move into having product based offerings.

Whatever the case, collaboration can be great for your business. And it can also be a big sink of wasted time wrapped in a lot of argument.

That’s why it’s important to think it through. You have to have boundaries for the project and the relationship. And understand the impact of the partnership will have on your freelancing day-to-day. After all, money still has to come in while the freelance side hustle grows.

Let’s focus on the growing of your freelance side hustle and how to move it from idea to reality.

Plan to have a plan

As boring as planning may sound, it’s essential to making sure a good idea doesn’t end up being a disaster in the making. Whether it’s about making money or working together on a passion project, a plan helps create the structure and the chance of success.

You need to vet the opportunity and set the ground rules.

Collaborating on a freelance side hustle only works if you:

1.      Have a clear vision for the undertaking. Do you both agree on where you want this to end up? If not, how different is the vision? Partnerships only get through tough times if your vision is compatible. If you don’t have that in the definition or development stage, step away from the idea and come back when you do. A vision of where this project is going will be the beacon that pulls you forward. Without it, it’s two people in the dark!

2.      Play to strengths. Coming together as parts to create a whole is about increasing your strength. But a common mistake in partnerships is having too similar a skill-set and treading on each other’s toes. Or attempting stuff where you aren’t using your best talents on a regular basis. Collaboration mean increased workload and more things to do. Play to your strengths and choose to work with people who expand your range of skills, not muddy them

3.      Develop a structure that allows for equality and/or proper recognition. Better outcomes come from individuals who feel free to take ownership of their stake in the freelance side hustle. Forget the committee of compromise. It only dilutes what you’re trying to do. Find a way to build alongside each other. If you can’t do that at the beginning, it will only get tougher to do as the project progresses

4.      Set goals you agree on. Small and large goals mark a successful project. So be clear about the milestones you want to reach in 3, 6- and 12-months’ time. Also be careful that you are the only person setting goals and the other person isn’t. It may mean you’re directing too much or that the person isn’t as interested as they seem

5.      Define success carefully. Outcomes give you something to aim for. What are you producing? What does a sell-out look like? What is success in your eyes? Be clear about how many social media followers you may want. Or what strategic partnerships and media opportunities you think suit the product. Understand your audience and how you want them to respond in detail

6.       Make it your business to have a strong focus on pricing and revenue. Money is the worst argument a partnership can have. And it can ruin a good partnership and take the friendship with it. We all want to make money out of our projects. Pricing should be based on research, not guesswork. And it should be a reflection of the market, not your egos.  Knowing when and why and how and who gets paid is essential

7.      Invent a methodology that supports both your aims. Think about product delivery. Define your role within that delivery process. How you are going to work together matters as it forms the core focus of your products. Make sure you define the division of labour to ensure work gets done in a fair manner

8.      Define your launch aims. Generating cash means your freelance side hustle a sustainable idea. That won’t happen straight away and will need to have a timeline that indicates what growth looks like. Some freelancers will want to establish a product and test the market to see potential. Others will want the project to price to pay for itself straight away. Others still will be prepared to wait years for pay-off. These are not compatible scenarios and will need to be agreed on before you launch

9.      No love and passion fluff. While you establish a new partnership or product, it will take you away from your core business. This has a time and financial cost associated with it. Many a friendship hits the rocks because it’s built on the love of a person without understanding the idea in full. You can’t believe “I would love to work with you” is enough. Love, passion and fluff are fleeting

10.   Personality helps, too.  We work differently. Complementary styles work. Complete differences in approach do not. Tread wisely. Respect each other’s working style and use it to enhance your performance. If it’s a battle of wills, it will lose it’s appeal pretty darn quick!

Setting up the process of collaboration

There are a couple of collaborative processes you need to have agreed and in writing before going forward:

§  Profit share– how is the money divided and paid, what is sunk back into the freelance side hustle as opposed to paid to the individuals involved etc

§  Setup costs– for example- websites, hosting, business registration, social media scheduling tools etc. If someone foots the bill and you dissolve the partnership later, you may have a lot less claim on the work than you think

§  Intellectual property– you need to register trademarks and associated IP and assign rights

§  Division of labour- many a well-intended partnership has come unstuck with one or more parties doing the majority of the work. This is why having defined roles is clear

§  Non-compete clauses– if the partnership dissolves, can you legally work in that space again? Where is the line in the sand?

§  A basic marketing plan– this, together with your strategy plans should form the basis of the engagement

§  Success measurements– have in writing the goals you want to kick. That way you’ll know when things are and aren’t going to plan

§  Project timelines– stage the work and stick to it. There’s no easier way to lose faith in a partner than the whoosh of deadlines. Or when one person is ready to launch and the other person is still fussing over the business documentation

§  Contracts – are a great idea as it gives you both structure and comfort. I would strongly advise against entering any kind of partnership without one. You need to outline the roles and responsibilities within the project. As well as goals, models and revenue generation model.

Yes, it sounds like I am sucking the fun out of collaboration. But the smarter way to think of it is starting it on the right foundation so you can get to the fun stuff without worries later.

Be wary of anyone who uses phrases like:

“We can work that out later”

“Planning makes me cross-eyed”

“Can’t this just be fun?”

“Let’s just see what happens”

These are the chosen phrases of someone who hasn’t thought it through properly. And they will turn into a nightmare; a rather expensive, stressful and unproductive nightmare.

Always check with your chosen partner before you start by asking this simple question:

What do you want to get out of this project?

If they can’t answer you or the answers don’t match what you want, don’t do it. Find someone else who does. Or work on the outline until you both agree on what is happening.

Also, don’t fall for the myth that you can take a load off your current work schedule by collaborating. It’s not going to play that way. Sorry!


Knowing how you work is the key to success

Want to know if collaborating on a freelance side hustle or creative project is for you?

§  Write down the elements of your work you enjoy the most

§  Write down what generates the best revenue

§  Write down the opportunities you have available

§  Run them through the pros and cons in the previous lesson

§  Ask the questions you need to work out if you are on the same page re: the 10 points of collaboration I introduced you to before

§  Ask yourself if what you like to do and what makes you money would benefit from teaming up

§  Sanity check the idea. Tell a few people what you are thinking of launching. What’s their reaction?


Got a successful freelance side project on the hunt to find someone to work with? Feel free to share it in the comments below.


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