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Starting Your Side Hustle
Starting Your Side Hustle
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This period is being called the 'Great Resignation' as more people question how they've been earning a living and seek out alternative ways to 'get their life back'. Maybe you're not in the position to quit, or it's not a clear cut decision for you. If that's the case, maybe consider launching a side hustle.  

It seems counterintuitive to commit to extra work when your job is demanding, life is busy, and you're still navigating a Covid world. Then again, perhaps it's the perfect time to try something new, without quitting your day job.

Side hustles provide you with opportunities to pursue your passion, experiment with an idea, express yourself, learn new skills, make new connections, and make some extra money. They're effortful, will eat into your free time, and if you choose right they might help to energise you and build your capacity in other areas of your life. Plus, you never know when a side hustle might just become your new business and career. In the meantime, progressive employers will see the benefit of you stretching yourself and developing new skills in your own time. 

It won't be easy. In fact, at different points — many points — you'll think you're just wasting your time. At those moments, be sure to come back to this Playbook.

This Playbook includes the following sections, select a heading to jump to that section.
Your business idea is only half the story, ensure that you're prepared for the journey ahead.
Jealousy as a Map
It's a weird place to start but the fact is your jealousy will help to shine a light on your unmet needs. Are you jealous of creative people? People who can afford great holidays? People who have built up broad respect? Identify your feelings and use them as a map to inform the goals of your side hustle.
Buffett's Two Lists
A side hustle is appealing but there are only so many hours in a day and you will only have so much headspace. The question isn't just what will you do, it's what are you saying 'no' to. Use this tip from Warren Buffet to get clear.
Stockdale Paradox
It will be tough, so what attitude will help you to stay resilient and maintain momentum? Time to explore the Stockdale Paradox.
You've already got a job so ensure that this side hustle speaks to your passions and drive. Use this model to help.
Regret Minimisation Framework

Still not quite ready to make the commitment? Use this model that helped Jeff Bezos start Amazon.
You know it's the hardest bit of your journey, so here's how to get started.
Idea Sex
You've already got expertise in something, though you probably take it for granted. How can you combine that expertise with another area or idea from a different domain to create something unique?
Architects vs Gardeners

Before you get to deep into your side hustle planning, consider this model from George R.R. Martin. It challenges you to consider whether to do a lot of planning upfront or start planting seeds and being more open to where they might lead.
Lean Startup

Leverage this model from startups to work with iterative feedback loops and building on your offer over time, with feedback from your customers.
Value Proposition
A lot of these models have focused on you, but to be commercial you're going to have to get clear on who you're delivering value for. Who is your customer and what problem are you solving for them?
1,000 True Fans
You don't need millions of fans — this model is a reminder for a more strategic approach to building a smaller community for a viable business.
Surface Area of Luck
As you start doing the work, ensure that you maximise your Surface Area of Luck by promoting and telling people about it. Getting the balance right will extend your opportunities.
You've got some momentum, here's how to keep it going.
4Ps of Marketing
You might have the best product or service, but if nobody hears about it, your side hustle will fail. Use this classic marketing model to get your offer out to the world.
Systems vs Goals
It's a side hustle and you've got other pressures on your life, so you're going to have to be disciplined about how you build it. Rather than focusing on goals, consider your systems and habits — perhaps you spend 2 hours on it every Saturday morning and switch out two of your streaming shows during the week to work on it instead?
Return On Failure
If you're not failing you're not doing anything. The question isn't 'will you fail', it's how will you boost your insights and learning from each failure and use it to pivot or inform your next attempt. Use this model to help.

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