How 25 Side Projects Led to Dream Careers

Yunzhe Zhou
Jun 19, 2018 · 22 min read

You’ve probably heard about the power of side projects: as a medium to explore different careers, gain new skills, test out business ideas, etc.

But how much difference can these projects really make?

I decided to try it out — and found that the difference is life-changing.

After doing 12 projects in 12 months, it brought me closer to my ideal life than ever before. In many ways, it’s the realization of many dreams in one year, from starting a blog to experimenting with alternative lifestyles. It all ties back to what I wished for more than anything: to blur the lines between work and play.

Not only the projects gave me the means to do that, but also the opportunity to get clear on what’s important to me. Every monthly challenge was a step closer to my ideal career. Every consistent action was an investment in my career capital. From Cal Newport’s So Good They Can’t Ignore You, career capital is known as “a set of skillsets that can be leveraged to define your career”. These can be anything from knowing how to learn effectively, to creating a kick-ass work portfolio, to building a tightly-woven network.

To start anything is also the hardest thing.

With that in mind, I curated a list of top side project doers in their respective fields so you can check out their ideas for inspiration. As a heads up, it’s a comprehensive post — to make sure you don’t miss any important takeaways, I created a recap of all the steps needed to create your own side project. You can get the recap here.

A brief note:

The below projects are categorized by 3 sections, with a common theme of “this is something I’ve always wanted to make” intertwined with “this project changed my life”:

  • Side projects that solidified expertise in current career
  • Side projects that catapulted the transition to a new career
  • Side projects that propelled the launch of a business

See yourself in one of these? :) Readers have gotten the most value from this post by going through the section that’s most relevant to them, and then using the step by step checklist on exactly how to create a side project to reach your career goals. Give me the free project checklist 🎁.

Also, the opinions and analysis accompanying the project summaries are my own — there’s no affiliation nor endorsement. I’ve included these projects because they are fascinating and would love to share them with you.

And in no particular order, off we go!


Side projects that solidified expertise in current career:

1. Daily Drop Cap

Project snapshot: This was Jessica Hische’s first personal project where she designed a letter a day until she created 12 alphabets. She attributes the Daily Drop Cap to jumpstarting her lettering career, and at one point, this project attracted up to 100,000 visitors per month.

Impact on career capital: Since then, Jessica has been featured under Forbes 30 Under 30 (twice!), spoken at more than 100 design events, and worked with clients ranging from Barack Obama to Nike to Mailchimp (here’s a behind the scenes lettering process, if you’re curious like I was). She’s also famous for her side projects, like the Should I Work for Free flowchart and Thousands Under 90 (a play off on 30 under 30 awards), sprinkled with warm-hearted humor throughout ;).

Her advice on 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.”

2. Four Minute Books

Project snapshot: Niklas Göke published a short 4 minute book summary of the world’s best books every day. He ended up creating over 400 summaries, attracting more than 20K readers, not mentioning getting featured in publications like Lifehacker and The Muse.

Impact on career capital: The discipline he gained from following through on daily goals gave him the foundation to pursue other intensive year-long projects like writing every day on Quora in 2017. Throughout the process, he discovered his love for writing and is now on the fast track to fulfilling his dream as a full-time writer. He is not only one of the most read authors on Medium but also an editor for numerous publications (all while being a grad student at the Technical University of Munich!). You can read his incredible advice on starting your own passion projects here.

His advice on side projects:Don’t even think about money before you’ve done something for 30 days in a row. Then, still don’t. When you work on a passion project for 30, 60, 90 days in a row, magic things start to happen, all on their own.”

3. Build an App in Two Months

Project snapshot: Mubashar Iqbal took on an experimental approach to his two month app — he crowdsourced the documentation method (people wanted to see the process instead of a recap), as well as the idea (a startup expense tracker), which gained a lot of traction among followers.

Impact on career capital: Mubashar became the to go person for taking side projects to market, especially with his nifty comprehensive timeline of steps from ideation to launch. This project also solidified his standing as one of internet’s most prolific makers (and earning around $10K month from projects). As a hobby, Mubashar runs the publication Making Side Project, where he curates all the best resources for side projects.

His advice on side projects: “I think the biggest mistake people make when they’re doing this thing for the first time is they start too large. They try and build a massive project that solves 100 different things, rather than something that specifically solves one thing.”

4. 52 Cups of Coffee

Project Snapshot: megan gebhart didn’t want to work in corporate after college, so during her senior year, she had coffee with a different person every week to learn about life and careers. Her adventures are nothing less than grande — she’s met people from all walks of life, from entrepreneurs like Apple co-founder Steve Wozniak, to a first grader from the Lakota Sioux tribe.

Impact on career capital: Her conversations inspired her to travel, turning this local project into an international adventure spanning seven countries (you’ll see why this is important later). Megan has also published a book also called 52 Cups of Coffee with stories of people she’s met on her journey. In an interesting sequence of events, she also is currently working at a corporation as a program manager for recruiting — and it’s no other than Airbnb, a global travel and experiences platform.

Her advice on side projects: I know that if I can continue to figure out what I love to do, find the courage to do it, and do it well — life will work out — and have a lot of fun in the process.”

5. Daily Purchase Drawings

Project snapshot: kate bingaman burt drew something that she purchased every single day for eight years until 2014. The Kate started it back again in 2017 when she turned 40 (and the project is still going strong!). What started out as curiosity around the story behind buying habits transformed into a focus around Obsessive Consumption — a personal brand unique to Kate.

Impact on career capital: After a year of drawing these purchases, Kate’s Daily Drawings Project became the sole source for all her freelancing work. Since then, she was able to merge her love for creating art and teaching students as part of her career, as well as work with variety of clients including IDEO, Uniqlo and Oprah Magazine. Kate is also powerful educator and advocator in the design community.

Her advice on side projects: “Be sure you’re putting the work you truly like in your portfolio and not just the work you think you should be making — or else you’re going to get hired to do work that you don’t even want to do.”

6. 12 Passion Projects in 12 Months

Project snapshot: These two Melbourne developers, the Shooting Unicorns team, set out to implement one passion project every month to build skills so that they can turn any idea into reality or a potential business. With their first test project Octogram (text them a photo and they’ll mail it to your loved ones for $4), they were able to just do that with a product and paying customers!

Impact on career capital: So far, Samantha and Luannie have learned a new technology for the first time in each project, including React and CSS grid. They’ve also explored some cool ideas, from Hustle Club, a startup and accelerator connector platform, to ClearPath, a navigational system to make public spaces more accessible for the blind and visually impaired. Stay tuned for what new skills they learn.

Their advice on side projects: “Think of each small thing you learn as a building piece and you’ll be building apps in no time.”

If you’re feeling inspired to start your own project, below is a snippet of the full side project checklist that you can get here.

Side projects that catapulted the transition to a new career:

1. Nas Daily

Project snapshot: When 24-year-old Nas realized that ⅓ of his life expectancy was over, he quit his engineering job to create daily 1 minute videos around the world. He committed to making them for 1000 days — each video takes more than 10 hours to film and edit. About a year in, his video on Thailand went viral! Now known as the “Humans of New York” for videos, the rest is history 👑.

Impact on career capital: With most of his waking hours dedicated to the process, Nas has honed not only his technical videography skills, but also his storytelling skills. As a testament to the fans’ engagement, his videos regularly get millions of views. In his free time, Nas connects people around the world, whether it’s through making a video creation app for sharing stories, or hosting meetups in cities (thanks for coming to SF) or buying an apartment in Palestine so visitors can stay for free.

His advice on side projects: “Do your best work: your work and what you produce need to matter to you before anyone else can care about it.”

2. 180 websites in 180 days

Project snapshot: An art school graduate who wanted to learn how to code, Jennifer Dewalt made 180 websites in 180 days as a learning project to teach herself from ground zero. Her perseverance with experiential learning ultimately landed her a spot at startup accelerator Y Combinator as a fellowship founder!

Impact on career capital: Starting from scratch, Jennifer first used HTML and CSS to build basic websites. By the end of 6 months, Jennifer was able to code using Javascript, Ruby on Rails and Node.js as well as build a full stack web app. She then took her newly acquired coding skills a step further and learned about business to launch Zube, a project management platform. It was one of the first batch of companies admitted to Y Combinator, and now used by teams like Autodesk and Universal Music Group.

Her advice on 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.”

3. Fear Year

Project snapshot: Elin Lööw faced her creative fears around writing and making art for a whole year. She approached it with one month at a time, and documented her progress with monthly reports. Over the course of a year, Elin not only built strong habits but also continuously redefined what “success” and “a creative” meant to her.

Impact on career capital: By December, Elin has achieved her original intentions of starting a blog. At the same time, with her consistent writing, she also gained credibility and followers endearingly called Teacup Owls (of which I’m also proudly part of — hoot 🦉). In addition, Elin started to pursue other creative outlets, such as photography and book writing, as well as opened up an art shop (and made sales!). All while working full-time, which is truly inspiring, because how many of these pursuits that we dream for ourselves do we achieve?

Her advice on side projects: “Turning dreams into reality is a long term project; actually, this is more than a project. This is life.”

4. Humans of New York

Project snapshot: Brandon Stanton wanted to make the jump from bond trader to photographer, so he practiced taking street photos of New Yorkers, every single day. After thousands of pictures, not only did he get really good at taking pictures, but also really great at listening and asking questions. Uncoincidentally, Humans of New York started getting traction and evolved to become the hallmark of what it is today: people sharing their most raw and vulnerable stories.

Impact on career capital: Though Brandon didn’t have any previous photography skills, only a camera he lugged around, he was able to make the transition from finance to arts through relentless practice. Averaging hundreds of pictures per day, Brandon quickly learned from the fast feedback he got. Now, not only is he able to capture poignant stories of humanity, but also use photography as a medium to generate awareness, and raise millions for charities and social causes.

His advice on side projects: “If I had sat around and waited until I had an idea to be a successful photographer, I would still be in finance.”

5. One Month Projects

Project snapshot: When Yunzhe Zhou moved cross-country for her job and felt lost in the new city, she did 12 projects in 12 months, a series of 30 day personal challenges to grow out of her comfort zone and experiment with blurring the lines between work and play. Two years later, when Yunzhe quit her job, she created a 2 month learning bootcamp based on the same monthly concept to quickly transition careers.

Impact on career capital: When Yunzhe first started her year-long project, she could not have even guessed the ways it would later transform her life. Not only did the learnings from the project quicken her career transition from marketer to writer and coach within two months, but also it became the muse for her new company. One Month Projects, an online accelerated learning and project implementation program, is Yunzhe’s dream career that merges work (empowering clients to take action) and play (traveling the world hosting workshops on habit design).

Her advice on side projects: “How we spend our days is how we spend our lives. What does your ideal day look like? Then center projects around that.”

6. 100 Days Without Fear

Project snapshot: Michelle Poler was tired of living her life in fear. To become a braver person, she created an online project where she documented her facing 100 fears, ranging from public speaking at TEDx to walking around NYC in a swimsuit to rappelling down a cliff. Michelle not only succeeded, but also sparked a movement called Hello Fears.

Impact on career capital: Fear is inextricably tied into our lives and careers. As Michelle faced her fears during lunch breaks at her day job as an Art Director and edited the videos at night after her masters classes, she became increasingly courageous. Midway through the project, Michelle mustered enough bravery to face her fear of the unknown, and quit her agency job to fully invest in the project, even though she had no idea where it would take her. Since then, Michelle has created a career for herself as a global speaker on fear and how to embrace life’s uncertainties.

Her advice on side projects: “Focus on the reward rather than the risk — I feel that when we want to achieve something and we have to take action, we immediately think about all the possible risks. If you focus on the reward, you are more likely to take that first step.”

7. The Decision Coach

Project snapshot: Originally a travel writer, Nell McShaneWulfhart would give advice to others for big decisions as a hobby since she was known to be analytical and decisive. Then, she started giving coaching to her friends and family, which grew into another career of its own.

Impact on career capital: Nell used her past informal coaching experiences to land a position as a writer for The Muse, an expert career advice site. She then took her advice-giving a step further, and founded The Decision Coach, where she offers action-focused guidance to help others achieve the lives they want. Nell has also expanded her career coaching offerings to encompass relationship and life advice.

Her advice on side projects: “The main reason we get stuck in this loop is fear. We’re simply afraid of making the wrong decision; so we delay, finding ever more creative ways to postpone making a choice.”

8. The Passion Co.

Project snapshot: An early operations employee at Airbnb, Jessica Semaan wanted to find a career that she was passionate about, so she started Passion Stories, a year-long project to interview 100 people who left their traditional jobs to do what they love. Inspired and with a clearer view of what she wanted, Jessica then set out to pursue her dream career.

Impact on career capital: Throughout the process, Jessica faced head on these stories around transition, fear, and mastery. Since realizing that she wanted to help others bring their dreams into life, Jessica co-founded The Passion Co., a 5 week program that helps and supports others to launch their own Passion Project or creative side projects. Past passion projects have included learning to play the violin, writing an app, prototyping an app, etc.

Her advice on side projects: “They say knowledge is power. I say knowing your fears is a super power — whether it’s we don’t think we are good enough, or we don’t trust uncertainty, or we do not know what to do next.”

Thanks for reading this far! If this resource has been useful for you, please share it on Facebook or Twitter so others can find it too :)

Side projects that propelled the launch of a business:

1. Nat Eliason

Project snapshot: Nat Eliason started a personal website as an outlet of self-expression and experimentation in content marketing on topics such as self-education, lifestyle business, etc. (he is also one of my favorite writers to follow!). Fast forward to now, Nat has applied his learnings from running a website that gets about half a million visitors per month to his new business.

Impact on career capital: When he started his site, Nat learned two things — that writing about a variety of topics can actually set him apart (instead of focusing on a niche), and that process is more important than the goal (prioritizing writing great posts over getting email subscribers). Over the years, Nat has been consistently publishing weekly posts and Monday Medley newsletters (this week is #110 and counting 🎉). Now an expert in learning and marketing, Nat created Growth Machine, a content marketing agency that focuses on generating free traffic from google with quality posts. As a fun side project, he also just opened a tea e-commerce store in 3 weeks called Cup & Leaf, using similar strategies.

His advice on 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. Scrum Your Wedding

Project snapshot: When they were getting married to their respective partners, close friends Hannah Kane and Julia Smith decided to play with their existing knowledge of Scrum, a project management process, to plan their wedding adventures. And it turned out to be super fun, both personally and professionally!

Impact on career capital: Taking a learning-by-doing mindset, they applied the Scrum methodology to fit every step of the wedding planning. By using visioning exercises, roles (‘Scrum Master” and “Product Owner”), rituals as meetings, and artifacts for progress, they worked with their husbands and pulled off two incredible weddings. Because Hannah and Julia had such a great time with their Scrum project, they turned it into a company called Scrum Your Wedding. It’s a full out wedding planning business, complete with a comprehensive guide and individual coaching sessions for a wedding that could be “the most creative and enjoyable project of your life.”

Her advice on side projects: Projects are iterative. Rather than planning out every detail in advance, you’ll work in small chunks, stopping frequently to re-evaluate, learn, and change course if needed.”

3. Month to Master

Project snapshot: Max Deutsch wanted to see how much he could push the limits of what is possible to achieve in a month, so he committed to pursuing an expert level skill each month for a year. With a couple of focused practice hours every day each month, Max was able to learn how to land a backflip, build a self-driving car, and hold a 30 minute conversation on future of tech in Hebrew!

Impact on career capital: With such intensive and fast feedback loops, Max was not only able to acquire specific skills, but also become an expert at the meta-skill of learning how to learn. Drawing upon lessons he learned from these mastery challenges as well as the enormous amount of interest others expressed in learning, Max created an education company called Openmind. At Openmind, he helps students invest in their skills to create the future they want by pairing them up 1:1 with a mentor in a specific area of expertise.

His advice on side projects: “I try to optimize for small daily doses of consistent progress. Consistent work, even if it’s small, compounds and builds momentum quickly.”

4. PassionBlueprint

Project snapshot: Derrick Kwa has been approaching his life as a project — ever since leaving school at 16, he’s been experimenting with living on his own terms and forging his own path. This has led to adventures he wouldn’t have experienced otherwise, like landing an impressive internship with the awesome Seth Godin as well as completing his AltMBA program (4 week project-based accelerator).

Impact on career capital: Determinedly going after his interests has led Derrick to pursue his passions one by one, whether it’s traveling around the world, playing in professional poker tournaments or starting a marketing business called Thousand True Fans. Tying all these experiences together, Derrick now interviews someone each month who has taken steps towards following their passions, so that others can be inspired to do the same. His podcast has covered a variety of people in art, business and nonprofits.

His advice on side projects: The question now is: what are you passionate enough about, that you’ll 1) push yourself to become great at, and 2) connect with the people who need it.”

5. 100 Days of Rejection

Project snapshot: Jia Jiang had a fear of getting rejected. In order to overcome it, he began a personal challenge of getting rejected every day for 100 days straight. His challenges ranged from borrowing $100 from a stranger, to making an announcement on a Southwest flight, to asking for olympic symbol donuts at Krispy Kreme 🍩.

Impact on career capital: Over time, Jia overcame his fears of rejection and learned to embrace the discomfort with these 100 days of rejections (you can see the full list here). After inspiring thousands on the internet with his journey and speaking at TEDx, Jia took what he learned, and founded Wuju Learning, a company that incorporates the science of rejection to train organizations to become fearless. He’s also building a mobile app to help even more people overcome their fears and achieve their dreams (if you’re interested, you can sign up for beta testing here).

His advice on side projects: “Is your dream bigger than your rejections? If it is, maybe it’s time to keep going, instead of giving up.”

6. Scott Young

Project snapshot: Scott Young started his blog as a project answering the question “What’s the best way to learn?”. Since then, it’s led to multiple year-long experiments in learning; one of the most famous is The MIT Challenge, where he learned MIT’s 4 year computer science curriculum at 4x the speed — in one year, without any classes or instructors 😲

Impact on career capital: With these projects, Scott has built disciplined habits as well as frameworks around learning and implementation. From his takeaways, Scott has created various courses around self-mastery and career development including Rapid Learner and Top Performer. He’s built a successful business doing what he loves, and has also partnered with other incredible educators like Cal Newport to bring accelerated learning into people’s’ lives.

His advice on side projects: “I’m a big believer in the power of side projects — this blog and business was once one. Nearly every professional milestone I’ve made was from something that happened in my spare time, and I don’t think that’s an accident.”

7. TiltMaps

Project snapshot: Mark Johnson dedicated 2017 to shipping a project each month. He ended up building 6 projects in total: one each month for the first half of the year, and spent the rest of the year turning one into a product that people would pay for (and learn about marketing in the process).

Impact on career capital: While juggling his other responsibilities (full time job, teaching as an adjunct professor, and consulting on the side), Mark still regularly shipped cool projects, ranging from a personality website analyzer to an AI driven witty chatbot. Perhaps the most notable was his project TiltMaps, where you can create unique map posters for your favorite places and memories, that Mark has turned into a side business. This project was the first side project he’s ever made a sale from , and requests are still coming in! As an extra benefit, Mark also sees TiltMaps as a great testing ground for trying out different sales strategies at his day job.

His advice on side projects: “You have enough time, what you need is motivation.”

8. 100 Days of Real Food

Project snapshot: Lisa Leake wanted a healthier lifestyle for her and her family so she decided to test the waters with a 10 Days of Real Food pledge. This challenge then expanded to 100 days of eating only real food with her family (no processed or refined food), and now a whole new lifestyle and business revolving around it 🌱.

Impact on career capital: Her first time blogging, Lisa wrote weekly updates on the experience of seeking out real food and recipes she experimented with for daily meals. Not only did she learn how to write for an audience, but also became an expert on how to navigate food challenges and eat healthy. Now, Lisa has a flourishing blog as well as a business around Real Foods, ranging from meal-plans to cookbooks to food programs. And perhaps most importantly, she’s changed her family’s life as well as countless other families on adopting real food as their “new normal”.

Her advice on side projects: Stop planning and start doing — you will be amazed at how experience, results, and happiness will build upon themselves.”

9. Fluent in 3 Months

Project snapshot: Benny Lewis was tired of not progressing past average level in languages (raise your hand if you also took 5 years of Spanish in school and still can’t understand it ✋), so he tried a different approach by making a 3 month project around learning each language, starting with the Czech Project. And he became fluent! Benny then continued with other languages (you can see how many he’s fluent in below).

Impact on career capital: With his projects, Benny opened documented them: in his monthly updates, he detailed the resources he found useful, the language hacking tips he discovered, and the mindset he acquired (that whatever he’s learning isn’t a difficult language). Now Benny, who calls himself the Irish Polyglot, is known as a language learning expert. He speaks 7 language fluently, not to include conversationally fluent in four others. He also has his own courses of Fluent in 3 months based on his system for learning, and acts as a language consultation coach for organizations.

His advice on side projects: “The difference between a stumbling block and a stepping stone is how high you raise your foot.”

10. 10 Principles Project

Project snapshot: Inspired by Burning Man’s 10 cultural principles, Maria Lambert Bridge wanted to see how it would be like to live radically in 2017. To explore “How do the beliefs we live our life by affect our interpretation of reality?”, she created a small daily practice related to each principle, and then implemented a different practice each month. Maria calls 2017 as “the happiest year she’s ever had”.

Impact on career capital: Maria consistently followed her monthly practice in principled living for a whole year, with one small daily action and 1–2 bigger actions to do for each month. For example, in May for the principle of Radical Self-Expression, she spend 10 minutes doodling each morning, and gave a talk at Stanford Business School on vulnerability. As she experienced the value of living into her ideals as well as mindfulness, Maria gained the insight and inspiration to found Topo Group, a consultancy that helps teams and executives be in flow at work, as well as Mind Matters Most, an initiative to support busy people in building a mindfulness practice. For 2018, she’s also continuing with her yearly themes with “Just Relaxing” to be truly present in life.

Her advice on side projects: To build a habit, set uncomfortably small goals.”


The power of side projects is that it can led to the realization of pre-planned goals. The beauty is that it can also led careers that are unexpected — ones that may not have been discovered without taking that first step.

To start anything is also the hardest thing.

If you want to take that first step, click here to get the starter guide you can use to create your own side project now 🎉

Yunzhe Zhou

Written by

Designing life through monthly action plans. For how you you can get started on a side project, get the toolkit here: bit.ly/12sideprojects ✨

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade