Side projects are great – they’re a low risk way of building new skills, trying unfamiliar things and discovering what sort of work makes you happy.

I am often approached by people to help them with their side project, and I get a lot of joy from that too.
Sometimes I can help with a solution or piece of advice.
More often, I can help by pointing them to a better set of questions, which in turn leads them to their “Aha!” moments.

Here are some of my favourite questions for interesting side projects:

What am I looking to gain?
I don’t know if you’ve played the game Settlers Of Catan, a board game based around acquiring and trading resources – a better version of Monopoly.
It’s a captivating game because you’re always actively involved, even during someone else’s turn.

There are five “currencies” (like bricks, timber and wheat) that you can earn, and then use various combinations of these to advance throughout the game.
As the game progresses, different currencies suddenly become more valuable, and you start looking to make win/win trades with the other players.

The frustrations and joys of trading in multiple currencies at once is the feeling you get from a side project.
You’re trading in currencies like time, energy, relationships, knowledge, cash and sleep – often swapping those which are plentiful for those that are scarce.

Maybe you’re calling in favours in order to build something quickly.
Maybe you’re giving out favours in exchange for money or experience.
Maybe you’re burning the candle at both ends in order to meet deadlines.

Either way, be clear about what you’re ultimately trading for.
Is it actually about money?
Or something bigger?

By filtering all your options through this lens, you remove a lot of the “nice to haves” and strip it back to what matters most.

What do people like most about my idea?
If you have an interesting side project, you’ll find people say nice things to you.
This can be fuel, but it can also be misleading.
When they say nice things, what part of the idea are they describing?

For example, many social enterprise startups attract fans, but not customers.
Maybe they love the concept of doing good and building a business, but they’re not buying anything themselves.
So what they really like is your story.
This is deceptive, because no social enterprise can live on well-wishes and “likes” alone.

Similarly, are they complimenting the idea, or are they complimenting you?
Both are lovely, but they tell you different things.
If it’s the idea, what parts really resonate with them?
If it’s you, what attributes do they notice? (and what don’t they like about the idea?)

This is really valuable, because it gives you clues about when to cut features, and when to double-down on the most interesting elements.

Gun to my head, could I compress the next 10 years into 6 months?
This question is from the book Tools of Titans, and makes people think in an uncomfortable way.
Our minds generally associate traditional timelines with activities – even if these are outdated and inaccurate.
Your development is not restricted to the “usual” way of growing an idea.

Sure, 6 months might seem unreasonable, but you get the point.
By switching to “Can If” thinking and identifying the real drivers of development, you can save a lot of time and energy, and focus more on the things that really matter.

Do we need to pivot or persevere?
There are two great components to this question.
Firstly, it’s good to be reminded that both options exist – you always have choices.
Secondly, people generally have a gut response to this question that they don’t like.
In fact, they came to me so I could help them with one, but in fact they really need to do the other.

Sometimes you need to stick with an idea to see it out, even when it’s tempting to make changes.
Just because progress feels slow doesn’t mean you’re going in the wrong direction.

Sometimes you need to change something fundamental with your idea in order for it to flourish, like pruning back a tree.
If your customers are telling you something vital, it’s better to listen than to try and drown out the bad news.

Generally speaking, the one that scares you more is the one you need to do, and there’s not a whole lot of benefit in lying to yourself.

Do I need to learn a skill or hire a professional?
When starting a new project, you get to do everything.
This is a mixed blessing – you’re exposed to lots of interesting fields, but you also don’t have the time or energy to master them all.

Most things can be outsourced, although not all of them should be outsourced.
This is partially due to cost, but mainly because the process of learning these skills gives you the ability to make your project successful.

These might include:
·      How to take/edit great photos
·      Website development
·      How to write captivating content
·      Creating and measuring social media campaigns
·      How to manage your accounts & taxes
·      Relevant parts of the law for your industry
·      How to find, recruit and onboard good people
·      How to talk to the media
·      Designing a logo and brand identity

All of these can are useful, but not all of them should be pursued straight away.
Do you need a quick result, or do you need to build a skill?

What will I never do?
My favourite AFL coach, Paul Roos, developed his philosophy through a 25-point manifesto he made at the end of his playing career.

He would observe the unhelpful and damaging things his coaches would do, and vowed to never do those himself.
e.g. blaming players for accidental mistakes, screaming at people after the game, keeping an air of mystery, and only rewarding the superstar players.

This list, made before his coaching career began, enabled him to avoid the common temptations and traps that would usually sour most other coaches’ relationships with their team.

For your project, I bet you’ve got things you’ve decided never to do.
By articulating them, you build these core principles into your culture, and help future team members avoid unhelpful “traditions” that plague your industry.
Which corners will you never cut?
How will you treat people?
What are your “lines in the sand”?

What is most important right now?
The two crucial words here are “most” and “now”

“Most” is critical – anyone can make a long list of good things to do, but prioritising that list is much more valuable.
“Now” is magical, because it turns vague statements into actionable plans.

It also gives the people you meet a practical way of contributing, by identifying what actions they can take in the next few days that will make a meaningful difference to you and your project.