Small Business

How To Get That Side Project Started

Most small business owners will be familiar with using Gmail, Adsense and Google News. What’s lesser known is that each of these digital tools came about as a side project, when employees at Google were offered the chance to use 20% of their time to come up with a new idea or company. Likewise, Groupon, Unsplash, WeWork, Craigslist and even Twitter were created initially as side projects.

The idea of the side project is nothing new, however in 2019, the opportunity to leverage community and technology to bring your creative project to life is unparalleled. So, what are the dos and don’ts of a successful side project, and how can we craft side projects that satisfy our creative spirits without adding overwhelm and stress?

This month Fiona Killackey of My Daily Business Coach shares tips for embracing your side project, and chats with Madeleine Dore, founder of Side Project Sessions.

Fiona Killackey

Madeleine Dore, founder of Side Project Sessions. Photo – Marie-Luise Skibbe.

A Side Project Sessions held in Melbourne. Photo – Marie-Luise Skibbe.

‘We Deal In Courage’. Photo – Marie-Luise Skibbe.

Photo – Marie-Luise.

Fiona Killackey
22nd of March 2019


 1. Know your Reason

In this era of the multi-passionate entrepreneur, everyone and anyone has a side project. What’s crucial to uncover is your reason behind embracing one. Are you simply fulfilling a creative urge that’s not being met in your current job? Are you aiming to build this out into a full-time gig? Are you working on something you know may not make enough money to support you, but that you’ll regret on your deathbed if you don’t give it a shot? Have you been sitting on an idea for years and realise it’s now or never? Or, are you doing this because you think you “should”? Taking the time to reflect on why you’re doing this is essential for driving long-term commitment and contentment.  

2. Start small

One of the biggest reasons people fail to start, or seriously commit to, their side project is the belief that they just don’t have the time. History is peppered with authors and artists who began, little by little, working on their craft. Publications we consume daily i.e. The Design Files (!) and Cool Hunting were both started “on the side” by creatives who wanted to document what was happening in their world at the time. Hal Elrod, author of The Miracle Morning, suggests taking just 10 minutes each morning to work on something you love such as creative writing. Isn’t starting small better than never starting at all? 

3. Focus On Yourself

In addition to time, the dreaded ‘comparisonitis’ can be one of the biggest obstacles for people to overcome when looking to embrace a side project. As Baz Luhrmann wrote in his lyrics for the infamous Sunscreen Song, ‘Don’t waste your time on jealousy; sometimes you’re ahead, sometimes you’re behind… the race is long, and in the end, it’s only with yourself’. When it comes to your side project, focus on your own goals and subgoals rather than getting caught up in what you perceive you “should” be doing. For those needing more help with this, check out The Crossroads of Should and Must by artist Ella Luna.  

4. Stay accountable

Like anything else we want to accomplish in life – good health, strong relationships – embracing the side project takes effort and time. Finding a way to stay accountable to your work (such as attending Side Project Sessions!) can be the difference between accomplishing your goals or simply dreaming about doing so.  

5. Share your wins

Chances are someone or something has inspired you to embrace your own side project. Enable others to be inspired by what you have achieved (and what they could potentially achieve themselves) by sharing your wins. This may be speaking about it with friends and family, writing about it on social networks, putting yourself forward to be on a panel around the subject of your side project or even submitting the story behind how you started and what you have accomplished with your side project to media. By being brave enough to do this, we can encourage others to pursue their own creative side projects.


Fiona Killackey is a business consultant, author, and mentor for My Daily Business Coach. You can sign up to her weekly email full of small biz insights and tips here or purchase her new ebook, all about having a great business year here.


There are few Australian creatives as well versed in the art of the side project as Madeleine Dore (aka founder of Extraordinary Routines). As an editor, writer, content strategist, interviewer, speaker and accountability coach she understands well the struggle and overwhelm that can come from juggling multiple creative pursuits. She also understands how to balance these projects to fuel creative fulfilment. In 2018 Madeleine launched Side Project Sessions – a regular event series designed to help you overcome various blocks to getting started on your project, big or small. We caught up with Madeleine to discuss her latest venture, as well as her tips for anyone looking to embrace their side project.  

What is Side Project Sessions and how does it help people create or sustain their side projects?

Through starting my own side project Extraordinary Routines five years ago, I’ve seen first hand how personal work can help you make traction in a profession or turn into an unexpected business or career path, or simply just create a sense of enjoyment in your daily life.  

 I also know all too well the pressures and challenges that came along with finding the time, motivation and confidence to get something started or keep up momentum. Through my interviews, I’ve also noticed that these blocks and distractions don’t necessarily become any easier to navigate – even some of the most experienced artists, designers and business owners have fear, doubt and procrastination tendencies! 

Side Project Sessions was born out of this observed – and also very personal! – frustration of seeing personal creative work continue to fall to the bottom of the to do list. I wanted to create a space where people could feel accountable and focused, build a regular routine, and be surrounded by a community of creative and inspired people. I like to think of it as peer-pressured productivity for your labour of love! 

The regular event series is not about the hustle, making money or even networking necessarily, but rather making time for whatever you’ve been putting off – people have worked anything from novels and illustration projects, to writing resignation letters or pruning a neglected houseplant! 

It’s amazing to see people dedicate every second Sunday to their ideas and projects, build some regularity and get momentum for something they might have been putting off for years. 

If you could give people three tips on how to get started on building up their side project (while also working another job), what would they be?

1. Redefine what success means to you: side projects are an opportunity to redefine traditional measures of success, such as fame or fortune, and explore what contributes to your own sense of satisfaction in daily life. It could be learning a new skill, adding to your portfolio, meeting a new person, or overcoming a fear of failure – success is unique to each individual and each project, and more to do with how you feel in yourself than how you think you look to others. 

2. Start Small: self-doubt, procrastination and perfectionism can be some of the biggest hurdles in starting or sustaining a project. Starting small helps to manage expectations and keep side projects accessible and achievable. Done is better than perfect!

3. Carve out time in your schedule: a common misstep is to think you need an entire day, week or month to get something off the ground, when really you need to use the moment that you have available. Through the events, I’ve learnt that one morning a fortnight actually doing the work is worth far more than a year spent just thinking about it. Pick a time and show up ­– momentum will often help do the rest.

 What’s the biggest block in your opinion, for people not pursuing a side project?

Behind self-doubt, procrastination, comparison, feeling behind, or overwhelmed is often fear – fear of failing, or being bad at something, or not quite measuring up to our own expectations.  

Often the only antidote to being afraid of the work is doing the work and reminding yourself again and again that you make your own rules for your own side projects. 

What’s next for you/Side Project Sessions?

The event series is expanding in unpredictable ways – new chapters are starting up across the globe from Adelaide to Akron, Ohio and I’m hoping to expand to more cities throughout 2019. 

There has also been interest in more one-on-one accountability, so for the first time, I’m offering private routine and side project accountability sessions for people who need that extra nudge or clarity to get something they’ve always dreamed of finally started. 

Both Side Project Sessions and Extraordinary Routines remain my side projects, so I’m continuing with freelance writing, interviewing, speaking and experimenting with my own routine! 

Sign up to the next Side Project Session online or connect with Madeleine on Instagram.

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