Getting Ahead

The 51 Coolest Side Projects We've Ever Seen


We talk a lot about inspiring careers here. But what often gets neglected as we’re talking about all the cool things people are doing during their day jobs is all the cool things they’re doing outside of the 9-to-5.

So today, we’re fixing that in a big way. Read on for 51 of the coolest side ventures we’ve ever seen. These projects really run the gamut—from blogs to small businesses, projects that are just getting off the ground to ones that have already been completed—but they all have one thing in common: They’re pretty inspiring.

If you’ve ever wondered about pursuing a passion project in your free time, check these out as proof of the amazing things that can be done outside of a full-time job. Then, sign up for our free email class to learn how to start your own!

Publications and Podcasts

Blogs are the original side project and what many people think of when they consider starting one—so we figured we’d start there, too. This section includes anything that is published at regular intervals—be it a blog, a print publication, a podcast, or a newsletter!

1. This Message is Medium Rare

What it Is: A blog about trying out different burgers and using them for design lessons and inspiration (really).

Why We Love It: Because it’s really the perfect example of a side project. It’s something that you’d actually want to do in your free time (eat burgers), but it also allows the designers who started it to hone their skills. And it’s led to impressive success: They were featured in Squarespace advertising since they use the platform, and they are looking to make a book or some sort of publication out of it.


What it Is: Content strategist Lindsay Mueller’s thoughts on living well, living simply, and living mindfully.

Why We Love It: Because it’s clean, it’s beautiful, and it clearly gives the author a change of pace from her day job. A side project that forces the author to think about living a more balanced life? Sign us up.


What it Is: A storytelling podcast produced and written by Jonathan Hirsch that tells documentary audio stories about moments in our lives when we experience unexpected change.

Why We Love It: If blogs are the original side project, then podcasts are the new frontier. Still, unless you’re Serial, it probably won’t pay the bills (at least not right away!). That’s why Hirsch does this on the side of restaurant and freelance jobs.

4. Sketchplanations

What it Is: A weekly newsletter sending you simple sketches that teach you things.

Why We Love It: This started out as a personal, analog project—UX designer Jonathan Hey received a journal with a page every day for a year of sketching, which he used to practice the skill. When he got to the end, he wanted another challenge, so he decided to start sketching one explanation a day and sharing it with the world. He has now cut back to once a week because life happens, and that’s okay.

5. asongaday

What it Is: Started by Shannon Byrne “kind of sort of out of demand, but mostly because a lot of people seem to be lacking resources for music discovery,” this service sends you a hand-curated song to your inbox every day, based on your preferences.

Why We Love It: Byrne’s side projects gives other people side projects, too—her curators are just regular humans who love music and want to share that on the side. You can even easily sign up to be one on the site! Or just be a happy listener like we are.

6. Graze Magazine

What it Is: A semi-annual print magazine that combines a literary magazine with a food publication, telling stories centered around food and sharing beautiful or funny art inspired by it.

Why We Love It: Because we love that in the age of digital media, a couple of magazine professionals decided to create a print outlet to express their more creative sides and explore passions they don’t get to in their day jobs.

7. Jim’s Pancakes

What it Is: A blog sharing pictures of the fancy pancakes founder of Shortstack, Jim Belosic, made for his daughter, along with instructions for how you can make them, too.

Why We Love It: Although it’s no longer active, this is a great example of how you can make a side project out of just about anything if you think creatively enough. He even got a book deal out of it!

8. Valerie & Valise

What it Is: A blog featuring the advice and adventures of a seasoned traveler.

Why We Love It: Started during a period of unemployment for Valerie, this project is a great reminder of the value of doing something you’re passionate about on the side of a job search, too. Not only did it become quite successful on its own, it’s led to multiple opportunities for Valerie: “It has helped me get a writing contract with Lonely Planet and commission for a piece with Yahoo Travel. It’s part portfolio piece, part my life’s work.”

9. Catalyst Wedding Co.

What it Is: A magazine and traveling workshop “building momentum away from the fantasy of The Perfect Wedding (TM) and towards celebrations of authentic love and community”—of all shapes, sizes, and styles.

Why We Love It: A group of friends decided to use their interest and expertise in the wedding industry (one is a wedding planner as one of her day jobs, another a wedding and engagement photographer) to add something a little different to the space. It’s great to see people using their talents in new ways outside of their 9-to-5.

Build a site like this using Squarespace’s Galapagos template!

10. Getting There

What it Is: A freelance writer and designer teamed up to do a weekly podcast about their daily lives as 20-somethings—and what you can learn from them in your own life.

Why We Love It: It’s a good reminder that you don’t always have to stray too far from the tree to find subject matter for a side project. Plus, it’s pretty cool that they were able to get picked up by an internet broadcasting network after doing just 15 episodes on their own.

11. Smart Experiments

What it Is: A blog detailing the results of various experiments that the writer is doing on his life—such as trying to make money with passive income or do morning rituals to build habits—all in an effort to becoming a better, happier person.

Why We Love It: It’s kind of a side project showing people the value of side projects. We think his monthly reports sharing how much money he made through passive income are especially interesting.

12. Everything Changes

What it Is: A newsletter by digital strategist Laura Olin that changes in topic, format, and frequency every week.

Why We Love It: Because it’s a fun approach to newsletters. And it means Olin isn’t locked into doing anything forever (it changes every week). The newsletter has seen so much success that it was recently picked up by The Awl.

Small Businesses and Consulting

Another common thread of side projects is using your spare time to test out an idea for a business or to launch a consulting or freelance practice that you can do on the side. It sounds like a huge undertaking, but the below examples prove that real people can actually do it!

13. Think Clearly

What it Is: A handwritten newsletter with reflection exercises and a couple of classes helping people re-learn how to use pen and paper to flesh out ideas.

Why We Love It: The project is an interesting mix of a periodical project (the newsletter) and some “one and done” work (the classes). It shows the different ways you can approach an idea in a side project.

14. Scrum Your Wedding

What it Is: A couple of friends combine their expertise and experiences getting hitched to coach you through a different way of thinking about wedding planning—using the Scrum methodology typically used in software projects. They offer individual coaching and a guide.

Why We Love It: It’s a fun example of using your professional expertise in a different way. These gals weren’t wedding planners, but they did have a lot of combined expertise in event planning and management; writing, editing, and social media; Agile project management/Scrum methodology; and collaborating with designers to produce beautiful products. So they decided to use it to “help people save time, money, and, most importantly, their sanity.”

Build a site like this using Squarespace’s Bedford template!

15. The Decision Coach

What it Is: Coaching to help you tackle tough decisions in your life, whether they’re small or large, personal or professional.

Why We Love It: Started by a travel writer, this coaching is something she does that’s “fun (and refreshingly different)” on the side. Just goes to show that even people with the coolest jobs need outlets for something a little different.

16. Folk Rebellion

What it Is: A blog encouraging people to turn off from their digital lives more often, along with an ecommerce store selling paper goods and clothing.

Why We Love It: It came out of founder Jess Davis’ need to step back from her “fast paced, tech-based career”—and not only has it helped her take a break from her crazy digital day job, but it also gives other people the means to do the same.

17. Design Turnpike

What it Is: Goods made out of vintage recycled license plates, made by a guy who spends his days as a web designer in the automotive industry.

Why We Love It: Because it’s a very hands-on, artistic project with a beautiful digital presence. We’re sure it feels good after a long day sitting at a desk to come home and make things!

18. That Perfect Pair

What it Is: DJ services for weddings, including a vinyl-only music option.

Why We Love It: This music-loving pair got married—and then decided to combine their passions to start a side business. Having fun with one of your best friends while making a little extra dough? Sounds like a worthy side gig to us.

19. Alex Honeysett

What it Is: A consulting business that helps small businesses with the branding and marketing know-how they need to get off the ground.

Why We Love It: Honeysett has worked in corporate communications for 10 years, but a few years ago she started itching for something a little different—so she started sharing her expertise with startups on the side. It’s been so successful and enjoyable for her, she’s now getting ready to transition to it being her full-time gig.

20. Blue Moon Box

What it Is: A monthly subscription box of science experiments and projects for kids.

Why We Love It: As college students starting this venture while, you know, being students, it’s a great reminder that no one is too young to follow a passion on the side.

21. A Pocket Novel

What it Is: A store selling jewelry, textile, and paper goods.

Why We Love It: Having a small Etsy store on the side can be a great way to explore a passion or develop a new skill. Owner Jen Siomacco makes it all and sells it online and at festivals in her spare time from being a designer. (And, yes, she’s also involved with Catalyst Wedding Co. from above—because people with side projects tend to like to do a lot of side projects.)

22. All Glamping

What it Is: A site of glamping products and inspiration.

Why We Love It: As COO of a glamping truck rental company, founder Heidi Nicholl realized she knew more about the subject than she was able to share in her day job. So she bootstrapped this site from the ground up in her free time!

Social Good

Many people look to their side projects to have a little more meaning than their bring-home-the-bacon jobs. The next set of projects are pretty inspiring examples of how people are making a mark in their free time.

23. Max Love Project

What it Is: Started by Audra Dipadova Wilford when she discovered her four-year-old son had cancer, this site helps families who have children with cancer learn about and access lifestyle changes and innovative therapies to fight the disease.

Why We Love It: It’s an astounding example of taking a hardship and turning it into a positive and powerful side project. Plus, we’re impressed Wilford manages it all while working her full-time job and taking care of her family!

Build a site like this using Squarespace’s Bedford template!

24. Catalyst Scrubs

What it Is: A company that works with people in developing countries to produce high-quality, handmade scrubs at fair, living wages—creating economic opportunity for at-risk women in communities around the world.

Why We Love It: As a rehabilitation manager in her day job, founder Holly Godfrey found it challenging to find great healthcare uniforms—and decided to solve the problem herself while adding some good to the world.

25. Good Call

What it Is: A search engine helping students discover the best scholarships to apply to using data—giving them access to over $25 million in funds to help with their education.

Why We Love It: While it began as a project on the side of founder Eppie Vojt’s day job as a VP at Red Ventures, he made enough progress and saw enough success early on that he was able to convince his employer to fund it and allocate resources toward it.

26. Forever We

What it Is: Started with the mission to teach kids about how they can help with issues in the world and grow their natural empathy, Forever We sells a doll and book that represents the experience of the child undergoing treatment for cancer—and donates money to the cause with every purchase—allowing children and parents to have conversations around tough issues.

Why We Love It: Started by a mom of four kids, this is a great example that side projects aren’t just for people with traditional office jobs—people with full-time jobs like being parents need outlets for other things as well!

27. Gramforacause

What it Is: A service connecting Instagrammers with nonprofits in need of photography services to help add a little meaning to their photo posting.

Why We Love It: Interestingly, the project started as a simple Instagram hashtag and has grown from there, so it’s a great example of how you can start pretty small and scale as you go. Plus, it’s a brilliant idea to turn a favorite social media pastime into something more.

28. Spur Projects

What it Is: A set of projects and campaigns to help reduce the suicide rate among Australian men and to lower the help-seeking barriers that many men having a tough time facing.

Why We Love It: It’s a niche topic, but one that the group of Australians who started it feel incredibly passionate about—and because they went for it, they’ve been able to make a difference! Even the most specific thing can be a side project if you care about it enough.

29. Sitting for a Cause

What it Is: A pet-sitting business that gives 50% of its profits to animal-related causes.

Why We Love It: Channeling her love of animals, the founder Ashley Jacobs started this by herself during her free time and was able to give over $4,600 to help homeless pets in her first two years. Now she is working on expanding it and creating a pet care booking website that continues to give back.

Events and Community Building

Organizing meetups, dinners, parties, networking drinks, conferences, or any other type of event can be a great side venture. Here is a variety of amazing examples of people really doing it.

30. The Tiniest Thai

What it Is: “The tiniest Thai restaurant in London,” a.k.a., a Thai food blog turned pop-up supper-club.

Why We Love It: Because we love Thai food. And also because founder Rachel Walder has let it grow and change naturally as time and interest changes, starting with the blog, then launching the supper club, and even offering “cook with me” days where she helps make cooking Thai food more accessible.

31. American Tripps

What it Is: Berlin-style ping-pong parties and a league. It’s kind of like musical chairs for ping-pong—check out the video to get a better feel for it.

Why We Love It: The founders had played this style of ping-pong during their travels and thought it was a great time—but didn’t find it anywhere in the States so decided it was an opportunity to do something themselves!

32. The Mr. Marina Competition

What it Is: An annual male pageant in San Francisco that raises money for the Leukemia & Lymphoma Society ($525K since its 2012 inception!).

Why We Love It: Because putting on an event like this is a pretty huge feat, so it’s pretty impressive and inspiring that founder and host Brianna Haag manages to do it in her spare time.

Build a site like this using Squarespace’s Bryant template!

33. Planned Outage

What it Is: A fully planned, three-day camping and kayaking trip to the Norwegian fjords.

Why We Love It: A couple of co-workers were planning a trip to unplug from the insanity of startup life—and decided to turn it into a little project and invite other people along. It’s a fun example of side projects in the most surprising of places.

34. Life Audit

What it Is: A system for evaluating your life and priorities—along with offerings for one-on-one sessions and parties to guide you through the process.

Why We Love It: What started simply as a personal exercise and article to share her experience turned into a full-blown project when queen of side projects Ximena Vengochea started getting feedback on the article and saw an opportunity.

35. Women Who Brunch

What it Is: A speaker series and networking group for women that happens over many people’s favorite meal of the week.

Why We Love It: A couple New Yorkers felt there weren’t enough good ways to learn from and connect with other inspiring women—so they decided to make it themselves. Plus, with one event a month for 12 women, it’s totally manageable on the side.

36. NomadTogether

What it Is: A community for location-independent couples and families.

Why We Love It: After selling their house and possessions and living on the road since early 2014, this six-person family realized a) they had a lot of knowledge to share, and b) they wanted to create a community of other families like them. It’s a great example of creating for the world exactly what you’re looking for yourself.

Inventions and Products

Some people in their spare time like to be a little more hands on—so they invent a new product and sell it. Check out these fun ideas that have become realities during the nights and weekends of driven professionals.

37. Nipyata

What it Is: Piñatas full of small bottles of liquor, delivered to your door.

Why We Love It: Um, piñatas full of booze. ’Nuff said.

Build a site like this using Squarespace’s Shift template!

38. Throne Watches

What it Is: Vintage watch faces upgraded with modern leather bands.

Why We Love It: Six “tinkering friends” started this project to get out of the creative slump of their day-to-day jobs. Most of them had no leather experience or watch-making experience at all, so figuring it out has been very rewarding.

39. Bharat Babies

What it Is: Age-appropriate books that tell the stories of India’s heritage to children of the Asian-Indian diaspora.

Why We Love It: Founder Sailaja Joshi noticed a gap in the market when she was pregnant and searching for books to read to her child. So she decided to create them herself to give all children of Asian-Indian access to books that resonate with their heritage.

40. Pivotte

What it Is: Classic clothing items made in high-tech fabrics to work for women on the go.

Why We Love It: Two jet-setting, on-the-go best friends had a shared love of fashion and using clothing as a method of expression but couldn’t find pieces that could keep up with their lifestyles. So they joined forces to make something better.


What it Is: A collapsable, reusable water bottle.

Why We Love It: Because we always forget to bring a water bottle because it doesn’t fit in our bag. But also because this is a great example of a side project at an early stage—founder Niki Singlaub has made the bottle and just successfully finished a Kickstarter to get it funded.

42. The Adventurous Mailbox

What it Is: Packages of adventure books plus access to an online community where kids can learn more about the world.

Why We Love It: After living abroad for 10 years, creator Andrew Bliss wanted to mentor kids from afar to instill the same sense of adventure in them and encourage them to embrace world cultures, learn new languages, and lead “well-examined lives.”

43. Read Between the Wines

What it Is: A fun, totally non-pretentious wine tasting board game.

Why We Love It: With day jobs in the finance industry, the duo who created this game wanted something totally different and totally fun to do in their free time. And they continue to have fun with it; they’re now developing a craft beer version (Brew Ha Ha!) and whiskey version (Whiskey Business).

44. Sweet-Seed

What is Is: Micro-batch seed blends and hummingbird nectar.

Why We Love It: Okay, it’s a little niche, but bear with us. This product is a great example of jumping ship on one passion and pursuing another. As one of the co-founders quipped, “Well the three of us were once in a band together. Then our attempt at a top 40 hit didn’t make it to the charts so we decided to do something else. The only logical thing; start a wild bird feed company!” Maybe not so logical, but it worked!

Just for Fun

Sometimes, side projects don’t have a great purpose or an end goal of being a big-time business—sometimes they’re just an outlet for doing something fun and different and seeing what happens. These next projects are all about that.


What it Is: A blog full of pictures of hot dogs in random situations, plus a store of prints and posters.

Why We Love It: It’s proof positive that side projects don’t have to—and in many cases shouldn’t!—be too serious. A photographer by profession, Laura Thompson uses the blog as a way to be a little more creative and to de-stress. In other words, the perfect goals for a side project.

46. Will Letter for Lunch

What it Is: An offering to hand-letter signs for local restaurants—in exchange for the food she writes out.

Why We Love It: Graphic designer Lauren Hom gets to practice her craft, without going through complicated payment systems or dealing with huge client expectations. She just gets a free snack out of it!

47. Design Pickup Lines

What it Is: A simple generator for punny pickup lines for designers.

Why We Love It: For someone with tech experience, this probably would’t take more than a day to set up. For someone who wants to learn tech, something like this could be a great early project.

48. Unseen Monsters

What it Is: Photos of cities with monsters drawn on top, who all have full back stories.

Why We Love It: This collaborative side project shows how two people can combine their skills and passions to create something awesome.

49. Thousands Under 90

What is It: Poking fun at all the “X under X” lists, this simple site allows anyone to create an award certificate for themselves. “Because you know you deserve it.”

Why We Love It: This side project makes people feel better about themselves. And we like that.

50. Story Jar

What is Is: A simple little web app that gives parents prompts to inspire bed time stories for their kids.

Why We Love It: Technologist and artist Stef Lewandowski has a physical story jar in his home, and decided to hack a quick web app that other people can use, too. A great example of turning a favorite thing into a quick side project.

51. 180 Websites in 180 Days

What it Is: A website about learning to build websites. Jennifer Dewalt wanted to learn to code, so she challenged herself to build one website a day for 180 days.

Why We Love It: It’s proof positive that a side project doesn’t have to be perfect to share it with the world. The process can be part of the project!