Secrets to Successful Side Projects

Fall is here and Winter is soon to follow! I’m gearing up for cozy nights indoors with matchy-matchy pajama sets, hot chocolate, and an incredibly intimidating list of side projects to pursue. This list includes starting a new cross-stitch, continuing to fix up a dollhouse I bought with Facebook Marketplace porch pickup during the pre-vaccine portion of the COVID-19 pandemic, utilizing coloring books for adults, restoring antique furniture, picking painting back up, making Halloween and Christmas decorations, and maybe subscribing to a craft box service.

When my Fall itinerary becomes a distant memory and mountains of snow get dumped on my doorstep, I tend to feel trapped in a simple work-life routine. A great way that I’ve found to free myself from that cycle is by taking on a side project (or two, or three, or six). It makes the housebound Winter (and any other time of year, really) feel fulfilling. When I have a side project, I no longer feel stuck inside due to the weather. Rather, I feel cozied up in my home, doing something productive that brings me incredible joy and satisfaction.


Does my side project have to be super ambitious? No!

So many marvelous behemoths started out as side projects: Classified ads wonderland Craigslist began as a “what’s happening in San Francisco” email newsletter that Craig Newmark sent to a dozen people. The holiday music miracle that is Trans-Siberian Orchestra started out as producer Paul O’Neill’s side-project. Home fragrance frontrunner Yankee Candle began its operations in the garage of sixteen-year-old Michael Kittredge’s family home. The first Apple computer ever built was made with Atari parts in Steve Jobs and Steve Wozniak’s spare time. However, a side project doesn’t have to be nearly as extensive as the examples listed. The point of a side project is to deepen your passions and to continue developing your skills. So, what are the secrets to a successful side project?


Set a goal for yourself

Define what you want to get out of doing a side project. Do you want to discover a new skill? Build upon a skill you already have? Try a new idea? Experiment with something out of your comfort zone? Do you simply want a creative outlet? Setting a goal will help guide you on your artistic journey. Whatever the answer is, side projects are a great stress reliever, can improve your mood, and build on your talents.


Establish a schedule and adhere to it

Assuming that you’ll somehow find the time for your side project is wishful thinking. Side projects can take up a tremendous amount of time, depending on their size. You need to be proactive and set aside time beforehand to continue making progress. However, make sure the amount of time that you’re dedicating is reasonable. It should be something that you are confident you can stick to. If you have a long list of chores to tackle, have kids to feed and bathe and get ready for bed each night, or you’re just tired after the workday, an every-day-for-four-hours schedule probably isn’t feasible. It’s completely acceptable to dedicate 30 minutes a day, 30 minutes a week, even 30 minutes a month to your side project. It’s all about what fits in well with your life.


Know when it’s time to abandon ship

Committing to something for a specified amount of time can be hard. It’s even harder when becomes something that no longer appeals or has value. Your side project should be something fun that will give you genuine satisfaction. It can be satisfaction from the process, the result, or both, so long as you feel good about what you are doing or creating! Setting check-in points is a great way of evaluating your progress.

Ask yourself these questions:

  1. Am I still finding this side project from the time and effort I’m putting in?
  2. Am I still looking forward to continuing this side project, or am I beginning to dread each scheduled work session?

Make an honest assessment of your project. If it’s no longer providing value, it’s perfectly fine to quit and find a more rewarding side project. Now, need some ideas?


Sign up for a subscription box

Kiwi Co offers 9 different lines of projects, suited to every age and interest. Boxes are delivered monthly. If you’d rather forgo a subscription, individual projects are also available for purchase. This option is particularly great if you have kids that you want to craft with as your side project.

Cloth & Paper sends unique writing tools monthly, perfect for those who are interested in journaling or planning.

The Crafter’s Box provides all the tools and materials needed to develop a new crafting skill each month. It’s on the pricier side, but what sets this subscription box apart is the artisan-led videos that explain each technique in detail. One-off workshops are also available for purchase.


Learn calligraphy and create your own greeting cards

How to Hand Letter on YouTube offers tips and tutorials for beginners.

I Try DIY’s tutorial is great if you’re not in the market for a bunch of calligraphy tools and simply want to learn how to mimic calligraphy with pen and paper.


Upcycle old clothes

We all have a closet full of things we no longer wear. Why not try your hand at reinventing what you already own? Upcycling can be a great way of rediscovering the love you once had for a particular garment. There is no need to be handy with a sewing machine. Hemming tape and hand-sewn embellishments are great ways to play. If you need some inspiration, coolirpa on YouTube is one of my favorite DIY fashion channels to binge-watch.


Participate in a daily challenge

Art challenges are great for the following reasons: you avoid decision-making fatigue since prompts for each day are provided. Consistency can help make creating art a regular habit and grow your skills.

Inktober is a month-long daily ink drawing challenge. If a daily challenge seems too daunting, Inktober 52 might be for you. A take on Inktober Classic, Inktober 52 is a year-long weekly ink drawing challenge.

36 Days of Type is a yearly challenge to design a letter or number each day for 36 days.

Footprint and Fancy Free’s Photo Challenge is a month-long photography challenge. It’s a great challenge for anyone interested in picking up a camera, or for photographers just looking for some inspiration.

Be creative in whatever you’d like with #The100DayProject. Simply pick a creative project you want to focus on and commit to working on it each day for 100 days.


In conclusion: side projects should be fun. Happy creating!

Josey Driscoll

Junior Graphic Designer

Josey is a graphic designer from the Philadelphia area, with a B.S. degree from Drexel University and minors in marketing, fine arts, and art history. She brings a unique mix of skills to Sweeney that stem from her experience in independent printing, corporate, city agency, and non-profit creative environments. Her goal is to support clients by creating meaningful, memorable design solutions and experiences. Josey is hardworking, detail-oriented and continually fascinated by the power of design.