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5 Wildly Successful Career Transitions Launched through a Side Project


If you’re looking for a career switch in 2019, side projects could be your secret superpower. Though the secret part won’t be for much longer, especially as companies have made it increasingly clear that they’re preferring skills over academic credentials in job applicants. And everyone seems to be doing (or at least thinking about) doing a side project.

The popularity of side projects attests to its superpower – not only does it allow you to showcase your skills, but also effectively learn new ones for a career switch. Through side projects you’ll not only get the experience you need, but also create connections with people or mentors in that new field, both of which are crucial to you getting your foot in the door.

There’s also really no risks nor downsides…and everything to gain. (Hey you there, here’s a quick guide to starting side projects, especially if you’re on the fence about your job :)) 

I also came across the power of side projects serendipitously when I did 12 side projects in 12 months. That led to an incredible journey of exploring my countless interests, skills I wanted to pick up, and eventually me switching into the BEST career I could ever dream of (coaching and writing). Compare this to before doing monthly projects – I had no idea what I wanted, in spite of years of brainstorming in my head.

Busy making lists, but not actually taking action to test it against reality.

But hey, don’t just take it from me.

Here are five behind-the-scenes stories of how these career changers successfully created a new career for themselves, as well as the exact side project they used as the springboard. This list is also carefully curated so that it includes the five most popular career transitions, including turning a creative hobby into a full-time business, and switching careers into a completely different field.

If this sounds like you, look no further. Click here to get all the resources you need to switch jobs via a side project.

The goal of this post is to make it easy for you to follow in the footsteps of one of these inspirational role models, or map out a similar transition for yourself. Ready to see how you can land your dream career?



1. Turn hobby into a full-time business

Nat Eliason is the perfect example of this with his side project (and one of my favorite writers!). He first started a personal website to write about self-education and experiment with content marketing. Every week, he would consistently publish in-depth articles and Monday Medley newsletters (this week is #137, which is equivalent to 2.5 years of writing).

Now, his website gets about an impressive half a million visitors per month. Nat took what he learned from his writing experience and applied it to the business world to create Growth Machine, a content marketing agency that focuses on generating free traffic from Google with high quality posts.

Nat’s tip for side projects: “Self-education can free you from a job you hate, from a college major you aren’t excited about, and it will be a core skill for the 21st century.” 

2. Turn (down) a 9-5 job to travel the world

When Nuseir Yassin, also known as Nas, felt like he was wasting his life away at his cushy engineering job, he decided to quit and travel the world. His side project was to create a 1 minute video every day to inspire others. Each Nas Daily video takes more than 10 hours to film and edit, and spans a variety of topics from “Albania’s Tattoo King” to “Singapore in 1 minute”. And back then, he didn’t have any videography experience, just a new camera and one way plane ticket.

Now, dozens of countries and hours of practice later, Nas has made traveling as his main job. He regularly partners up with destinations, brands and people around the world to showcase their uniqueness. Dubbed as “Humans of New York” for videos, Nas also spends time connecting with people around the world with awesome local meetups in cities.

Nas’s tip for side projects: “Do your best work: your work and what you produce need to matter to you before anyone else can care about it.”


3. Turn non-tech background into software engineering skills 

Jennifer Dewalt, an art school graduate who wanted to learn how to code, made it a learning project to create 180 websites in 180 days. In the beginning, Jennifer first taught herself HTML and CSS in order to build the most basic websites. Fast forward to 6 months and hundreds of sites later, Jennifer learned from the iterations and build upon it using other languages like Javascript, Ruby on Rails and Node.js.

Now, she is the founder and developer for Zube, a project management platform. Her perseverance with learning through experience also led to Zube being one of the first batch of companies admitted to the top startup accelerator Y Combinator!

Jennifer’s tip for side projects: “My biggest takeaway was letting go of my fear of making mistakes. Being ok with that is the only way not to be paralyzed by fear and keep making progress.”    


4. Turn hobby into a thriving creative career

Jessica Hische’s first personal project was where she designed a letter a day until she created 12 alphabets. She credits her Daily Drop Cap project to jumpstarting her lettering career and at one point, this project attracted up to 100K visitors per month.

Now, Jessica has worked with top clients ranging from The New York Times to Nike to Mailchimp. She’s also been featured under Forbes 30 Under 30 (twice!). Jessica is also famous for the other side projects she’s created since then, like the Should I Work for Free flowchart, a great resource if you’re just getting to the creative space.

Jessica’s tip for side projects: “Half of my side projects started because there was a skill I wanted to practice or something that I was excited to make but no one was hiring me to make it.”    


5. Turn being stuck at a job into loving a job

Kristie Moy, a social butterfly who felt stuck in her marketing job and wanted to transition into recruiting, created a project that gave her the the experience she needed without getting the recruiting job first. To do that, she matched fellow friends and acquaintances to companies with open roles as if she was a recruiting agency herself. Throughout the project, she was able to get hands-on experience in editing resumes, targeting specific positions, etc.

Now, she has switched into her dream company after working on the side project for less than three months. So far after 7 months on the job, she’s already hired 25 new people ranging from interns to senior roles at the growing startup, and loving her work.

Kristie’s tip for side projects: “You can use side projects in a variety of ways as a way to overcome the barriers to entry for new jobs. For example, you can use a project to learn skills, conduct informational interviews, apply your learnings like I did…the possibilities are really endless!”



These are creatives, students, and corporate professionals like you. And what’s so incredible about working on side projects is how the process levels the playing field. You can get the experience you need, regardless of where you worked before, or what you studied, or where you came from (which is great news if you also grew up in a small town in Virginia like me).

If you found yourself in one of the stories above, or see yourself in a similar career transition, here is a step by step toolkit you can use to start an unforgettable side project of your own!

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