Makers Gonna Make
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Makers Gonna Make

The experts guide to side projects

If you’re reading this then you need no introduction to the side project. They are proving to be the life-blood of many a modern creative. Side projects are the perfect way to express your style, engage your passions and reach out to the world. But it’s fast becoming a strategy of independent creatives and teams who are looking to grow their audience and create a business that resonates.

Beyond any other benefit, side projects provide hands-on education and experience. And for this reason, I’m really pleased that side-project grandmasters have agreed to share their knowledge and learning with me in this article. They share their experiences, their reason for doing side-projects, how they promote them, their biggest successes and their advice for others.

Side projects — the new blogging?

Before we jump into interviews with the experts it’s worth looking at some of the current discussions and perceptions of side-projects.

In a recent post on the Crew blog, Jory Mackay wrote about why side projects are the future of marketing and suggested that we should kill the blog in favour of them. This is perhaps taking it to the extreme as they compliment each other perfectly however, it is a statement based on the results side-projects have had for them as a startup. It wasn’t blogging that turned their business round, it was a side-project.

Paul Jarvis sees side projects as experiments, framing them like this has helped him overcome his fear of failure he’d originally associated with any project he undertook. In his article on 99u, Paul cites this change in mental perception, and the resultant side-projects, as being behind selling thousands of copies of a book he’s since written.

Although many side projects are for personal enjoyment, some come from a deep held desire. Jessica Hische’s not only found infamy as the ‘Drop Cap Girl’ after her Daily Drop Cap blog became a hit, it also ensured her continued success as a freelance illustrator and letterer and has landed her speaking slots at prestigious events like Creative Mornings and Smashing Conference. On her website Jessica states, “…my desire to do side projects became too much to bear. I ventured out on my own and embarked on a little project that would end up changing my career and earning me the moniker “That Drop Cap Girl”.”

Accidental success or notoriety is only one side of the coin, side projects can be commercial from the start, or have the intention of becoming commercial. David and Clare Hieatt have created a number of hugely successful side projects including Howies and the Do Lectures. But as David explains in “Why ‘Side Projects’ matter?”, these side projects took 6 years to mature to a point they put cash on the table. He explains how, for them, side projects are a labour of love.

Growth is only one measurement of success and not always the end of goal of a side-project, or any project for that matter. That’s one of the beauties about side-projects — you are not tied to commercial objectives, you can do them for whatever reason suits you — learning and education, experience, audience growth, personal satisfaction, networking, problem solving — you name it, it’s your call. My newsletter for creatives is a perfect example — I do this because I love sharing content. It will never make any money and I already have more subscribers than I’d originally hoped for. It is a passion project.

So, to find out how we can all get the most from our side-projects and to uncover what drives those who make them a part of their lives, I’ve spoken to people who’ve inspired me along the way and asked them to share their advice in this post. Rather than dissect their responses, I’ve left the answers in the authors’ own writing for you to gleam your own understanding and insights.

About the experts.

Stef Lewandowski (SL) — Stef is a self-proclaimed hacker. As a designer, software developer and startup founder, Stef is a craftsman for the digital age. He puts his skills to good use and up until recently, Stef was technical co-founder of Makeshift, a digital product company and is constantly working on creatively inspiring side-projects. He’s now working on something new that’s coming in January.

Violeta Nedkova (VN) — Through side projects and following her inner creative rebel, Violeta has carved out a strong reputation with clients looking for their unique marketing blueprint. As a prolific blogger and social media enthusiast, she is never short of collaborations and projects, which she undertakes with energy and passion.

Kevan Lee (KL) — As a content crafter at Buffer, Kevan has mastered the launch, test and repeat process for continual improvement and regularly shares findings and results on the Buffer blog. Kevan uses this mindset outside of his work at Buffer and often has a writing or creativity related side-project underway.

David Airey (DA) — David is a graphic designer who has turned a side-project into a globally renowned blog, Logo Design Love. This has lead to him authoring a book by the same name, “Logo Design Love: A Guide to Creating Iconic Brand Identities” now available in 10 languages. His commitment to his side project has seen him receive offers in excess of $90,000, which he turned down.

Fred Rivett (FR) — Fred is one half of We are Contrast, who in 2015 set the challenge of launching six projects in six months. Since completing the challenge Fred has continued to fill his spare time with side-projects and is currently co-authoring a book on the experience.

Spencer Fry (SF) — Spencer is a serial entrepreneur who has co-founded two multi-million dollar bootstrapped startups and is currently working on his new business, Coach. He’s in the process of writing a book but still finds time for side-projects including Sweat the Product, sharing the untold stories of entrepreneurs and people who build product.

Question 1: What is the main reason you do side projects?

VN: Side projects give me the opportunity to work with fellow creatives. And for a person who gets easily bored and suffocated by routine sometimes, they offer both relief and novelty. Not to mention they ALWAYS grow your audience. Of course, if the project is under your brand umbrella, meaning related to what you do and helpful to the people who need it.

SL: I’m always trying out new ideas. I call it “sketching with code”. I find that what I do in my spare time often bleeds into the work that I do. It’s a safe, staging area for ideas where there isn’t any pressure to have a business objective. I do tiny “hacks” around something I’ve spotted and more often than not they don’t go much further, but that’s kind of the point. In karate there is the idea of “kata” that you practice constantly. I apply similar thinking to side projects — stretching my “make a new prototype” muscles means that I’m able to make prototypes faster and with more consideration. Getting better at going quickly. Overall, side projects are fun, and when they’re not fun, I stop them.

FR: Side projects for me are a labour of love. Ever since I first learnt to design & write code I’ve been dreaming up ideas and working on side projects, although it’s only recently that we’ve managed to ship consistently. So I’d say that the love of creating has been the initial spark, but these days we’re pretty focussed on achieving our goal of bootstrapping our startup, so that drives what we do.

DA: I started my Logo Design Love website because I enjoy learning about design and sharing work I admire. In addition, I know that websites with a decent amount of visitors can help a little when it comes to earning an income.

Question 2: How have side projects benefitted you?

VN: They have helped me test my boundaries and discover what I like and don’t like. For example, I’ve discovered that I LOVE working with fellow writers, but not so much with fellow marketers. It’s just one of those things. :D

SL: Often it’s the side projects that spark conversation and connection with people. If you’re always forcing your startup down people’s throats at networking events it can get pretty boring. Having a few interesting comment-worthy things to talk about means that conversations are much more interesting. “Oh I did a jewellery idea a while back — it’s called the Data Necklace”. I often think that side projects are a great way of doing marketing for your main thing too. I have and people love it, but it doesn’t make money for me — it’s just a nice thing that people know me for having created.

KL: I’ll mostly do side project promotion through my personal social media accounts and also from the email list I’ve built at my personal site. Sometimes the side projects will include a bit of built-in promotion. My email newsletter for instance is a side project and a promotion experiment at the same time. :)

Some other options:
Guest blogging
Slack communities / community sites (Inbound/Growth Hackers)

FR: They’ve taught me how to go from concept to launch, to take an idea, let it breathe, smooth off the rough edges, and ship it. It’s been absolutely vital, as without launching your idea is worthless. On top of finally shipping some of the ideas we’ve had for a long time, there’s been so many benefits. From getting involved in the community, to finally starting to write, to landing a great job at an exciting startup, launching side projects has had a massive impact on my life. In terms of my work life it’s changed pretty much everything.

DA: Peachpit Press — a publisher in the United States — approached me out of the blue after visiting the Logo Design Love site. I was asked if I’d write a book about logos. The first edition was published back in 2010, and I’ve attracted clients who found me through the book. So there’s the book royalties I receive each quarter, and there’s client payments, too.

Question 3: How have you promoted your side projects?

VN: I promote my side projects like I promote everything else — with my unique marketing system, which includes: giving value, focusing on the social channels I like, and building my tribes. I don’t really see the point in doing something if it’s just cool or interesting or funny. It would have to fit with my overall strategy.

SL: Usually via Twitter. That tends to be where I put things and then if people like them then they grow by word of mouth. I don’t pay for advertising on them.

FR: 90% has been through Product Hunt, 5% Hacker News, 5% building in public, blogging about our experiences on our website.

DA: Through Facebook, Twitter, and with links from my portfolio. Straightforward, really.

SF: I currently only have one side project going: Sweat the Product. Other than the occasional casual conversation, I don’t really promote it outside of when I publish a new interview with a product person. When I do publish a new interview, I email the mailing list, post it to Twitter, Facebook, and individually email people I think might find it interesting.

Question 4: Are there any dangers, risks or down sides of doing side projects?

VN: Yep, they can distract you from your goals. I mean, I’d love to be working on my novel right now, but maybe once I establish my business first. The first year is the hardest and now is not the time to write fiction. However, I am considering some fun challenges and collaborations for 2016, which will also help my business grow, so win win!

SL: It can be distracting to be doing side projects. If you have investors they might take a dim view unless you can show a benefit, say like the Crew folks have side projects that benefit the core business. And if you have too many, your time can get chopped up into pieces. If people are paying you for a side project then support issues kick in and it can get pretty depressing when you’re bug-fixing late at night.

FR: It depends on your goals. It’s an investment in the long term, for me. Some people will do it for fun only, and in that case there’s no risk at all. For me that’s part of it, but my goal is to start my own business, so in a sense if I don’t ever achieve that goal then my investment (time) could have been invested in another way.

DA: They can take up more time than first expected, so don’t let them detract from work that pays the bills. Side projects might eventually provide your income, but that’s not going to happen if money worries mean you need to ditch them mid-flow.

Question 5: What is your favourite side project you have worked on?

VN: Grim5next. It was an anthology of science fiction stories (mostly dystopia & postapocalyptic) written by 36 authors, edited and illustrated by a bunch of other creatives. It was fun until I realized it was too much and I crumpled under the pressure. This was before I became a marketer and learned to delegate. Still regret leaving it.

SL: Oh gosh, I have so many. Right now it’s — I help my wife on this in my spare time, but it’s quickly becoming a full-on startup.

FR: Probably our first, HowsItGoin. It’s quite simple but took a lot of hard work, and being our first proper project will always hold fond memories.

DA: I have other side projects on the go, but Logo Design Love is probably the favourite because I always smile when people send positive feedback. Working on my own is sometimes isolating, so it’s really nice to know that what I publish is of use to others.

Question 6: What is the biggest side project success you’ve had?

VN: Can’t think of a success right now. It sounds lame, but it’s always either been projects just for fun or work for money. I’d say my current business is a budding success, but I don’t want to jinx it, and besides, it’s not a project. It’s my life now.

SL: — I was building this up in my spare time with a friend, doing prototypes and sketches, then we raised money and turned it into a 40+ person business.

FR: Probably launching FoundersKit, partnering with over 60 great companies to put together a sweet package of discounts. It went down really well on Product Hunt, with just under 1200 votes, the third highest that month, and has made some good money too.

DA: Some of the designers I featured in my book have gained clients on the back on their inclusion. That makes me particularly happy, because the contributors gave up a lot of their time to help me finish the content.

Question 7: What one bit of advice would you give fellow creative on side projects?

VN: When you get an inspired idea, grab it. Run with it. Learn from it. Don’t ever despair if it doesn’t work out and definitely don’t start with the idea of making money. Side projects should be fun first. If you’re not having fun, nobody else will.

SL: Let yourself quit.

KL: Go for it! I’ve noticed for myself this hesitancy toward side projects because of time or energy, which I’d imagine is true for most folks. Interesting, I’ve found that the time spent on side projects can bring about more energy, more excitement, and lead to some really great benefits for the day job, too. Seems that starting small can sometimes be the impetus to get going, too. Breaking down a big project into little bits and treating the little bits as side projects of their own (side projects of side projects?) can work wonders.

FR: Start small, set a deadline, nail your scope, tell someone and most of all, ship it. Move past your fears and hit the big shiny launch button.

DA: Do it.

SF: I think the best advice I can give is to not over think your side project. It’s a side project — not a business venture — so you shouldn’t treat it the same way. Go with the flow, trust your gut and just have fun with it.


One of the most interesting outcomes of researching side projects and speaking to experts has been the polar opposite approaches. Some see these as purely for fun, others have a commercial expectation for all projects and cull those that don’t show promise. This obviously has a big impact on the advice provided for getting the most from your side projects. It also changes where people see the benefits.

Side projects that are just for fun need to be that. They should always be enjoyable and you should have an interest in them. They shouldn’t be overthought and, as there are no commercial objectives it’s down to you how far you go with these projects. Don’t be afraid to quit or stop these side projects and be wary of them eating in to the work that puts cash on the table. But don’t be surprised if one of these becomes something bigger as has happened for David Airey and Jessica Hirsche. It might be the project that ends up defining you!

Commercial side projects need to be treated very differently. These can vary from a side project you vehemently believe in, to the side project you are just testing to see if it resonates with an audience. For the latter you want to ship early, learn quickly and fail fast, repeating this cycle until you find a project that gains traction. This is the approach taken by Stef Lewandowski and Fred Rivett. For the first option, this should be your passion — you are going to have to put time into this that will hopefully pay off in the future. This is the approach David and Clare Hieatt took with Howies and the Do Lectures. They are big commitments. One other thing is that side projects can quickly take up time, particularly if you get a reasonable user base. If you are doing things for a commercial reason make sure you keep focused on this and not get side tracked by the numbers.

Above all, the key is to go for it. Get started, learn as you go, whatever your objectives, and get your project shipped. The idea that sits in your head or stays around the coffee table is no use to anyone. If you are clear about why you’re doing side projects and keep this in mind they can be hugely rewarding. They will help you spark new connections, give you interesting things to talk about, keep you interested in what you are doing and help you develop your skills.

Read about our latest side-project along with the 4 key elements of success we learnt along the way.

About the author — James Qualtrough is co founder of Slidecraft, online presentation software that adds context and conversation to presentations. His side projects include Little Walden, a weekly newsletter for creatives and, beacon-based timing solutions for events.

Images on this post come from the awesome Unsplash.

Great links for side-project inspiration:




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James Qualtrough

James Qualtrough

Husband, Dad of 3 and Founder at

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