How to Choose the Right Side Projects

Jake Jorgovanby Jake Jorgovan

As creative professionals, we are approached with opportunities for side projects all the time. Often, these side projects have very little or zero budget, yet they still draw our interest.

Side projects could be:

  • A startup with an interesting idea.
  • A friend’s business that you know you could help.
  • A non-profit with a cause you believe in.
  • Or even an idea you come up with on your own.

Side projects take many forms and fashions, and despite how interesting they may all seem to be, we just can’t take them all on.

If we take on the wrong side projects, it can be disastrous. Getting involved in the wrong projects can ruin our friendships, waste our time, and prevent us from taking better opportunities that could have come along. How many times have you taken on a side project to later think to yourself, “Why did I agree to this?”

Choosing the proper side projects is more than a small choice. It will make or break your career.

Discover your motivations

Before taking on any side project, first evaluate your motivations for the project.

  • Why is it that you are even considering this project in the first place?
  • If you aren’t going to be paid up front, what are you expecting to get out of this project?

These are hard questions to answer, so below I have outlined a handful of motivations that may align with your side project.

Portfolio – Is this project going to become an incredible portfolio piece that you can showcase in the future? Will this be something you can use to win future freelance clients or your next job?

Skills – Will this project allow you to develop new skills or practice the ones you already have?

Control – How much control do you have over this project? Are you in charge or are you going to be answering to someone else’s final say?

Collaboration – Is this project giving you a chance to collaborate with someone new or meet new people?

Growth – Is this project going to push you out of your comfort zone or force you to utilize new skills?

Impact – Will this project make an impact in the world? Do you believe in it? Does it support a cause or make a small change that you want to see?

Passion – Are you passionate about this project and the industry that this project is in?

Scale – Does this project have the ability to scale into something bigger? Or, is it purely a one-off project?

Profit – Does this project have the ability to provide an income or financial success down the line?

It’s not always about the money

Notice that profit is last on this list. It’s last on the list because profit is the WORST motivation.

One of the biggest mistakes freelancers make when choosing their side projects is being motivated solely by money.

They hop on a startup with dreams of someday selling their shares and getting rich. This is the completely wrong way to approach an unpaid. When you are in it for the money, it’s easy to lose motivation when things get hard.

Instead of being motivated only by profit, identify your other motivations up front.

  • Do you want to work on this project because it is going to allow you to step into a new role?
  • Will this project become an incredible portfolio piece?
  • Will this project give you the ability to practice new skills?
  • Before taking on any side project, ask yourself, “What motivated me to work on this?”

When your motivations aren’t monetary, you can’t fail. Even if a project never makes a profit, you will have gained something for your portfolio, sharpened your skills, and pushed yourself. This makes your next project even better.

How to evaluate your next side project

Before taking on your next side project, step back and outline your motivations for getting involved. Take some time to go through the list in this post and see what is really driving you to want to hop in on this project.

Never take side projects purely on the basis of potential income. Instead, figure out what your motivations are for the project.

When you know your motivations, your projects will begin to align with your values.

Need some inspiration? Here are a few examples of successful side projects:


Michele Howley Boudreaux to first made a batch of lollipops for a design school assignment. Today, her handcrafted lollipops are a bona fide business through her Etsy shop, Lollipops by Mihow, where you’ll find inventive, gourmet flavors like “Grandma” (lavendar and lemon) or “Rise and Shine” (maple syrup and bacon). Read more about this project.


Throughout this year, Cibo is releasing its 365 Series, a collection of posters for each month of the year. Read more about Cibo.


Tina Roth Eisenberg started Tattly, a website that sells “designy temporary tattoos” as a side project. Read more about Eisenberg.


Washington, DC–area designer Jill Tanenbaum has turned her hobby of creating fused glass into a side business. Read more about Jill’s business.


Graphic designer Sumayya Alsenan is the jam-maker behind the beautifully packaged Cat Lady Preserves. Read more about Alsenan and see more great packaging design.

Jake Jorgovan is a writer, marketer and creative professional. He is VP of Growth at and recently published a Skillshare course called GO+DO: Start a creative project that matters.

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