Advice for starting a new side gig

After discovering the joys of walk-and-talk phone meetings I had been walking around my neighbourhood and now stood atop a hill, sun in my face, listening to my friend AA through my headphones. Like many of us she'd been feeling down for some time, giving herself to the daily grind that was survival, not really thinking about creative pursuits outside what was necessary. This had now changed.

"I have an idea of what I want to do, but how should I go about it?", she wanted to know.

It is a tough question. A big question. Creativity is laden with all kinds of emotions and its pursuit comes with many challenges, distractions, and risks. I do not hold all the answers (far from it!), but I sense that - as with many human problems - a degree of pause and reflection certainly doesn't go amiss.

Asking these sorts of questions seemed like a great way to start, and I was honoured to be the one she'd asked. After some consideration of my previous pet projects and side hustles, I shared the following few pieces of advice (which just so happen to be ten):

1. Check your motivation
   One of the most useful questions (maybe the most useful one) to ask yourself (or others) is why. If you have some energy and muse to throw at a new pursuit, why should it be this one you've come up with? The answer to this will be multifaceted, but I believe that one element it should encompass is passion. Do you really love what you are intending to begin? Are you excited by it? Do your motivations come from the inside? Or do you instead feel some sort of external motivation or pressure, like you just ought to do it, or because 'everyone else is'?
   There are many ways to describe side-projects, and some of them give away what it takes for them to succeed: We call them pet projects or passion projects, not because this is the only use we derive from them, but because that's what is required to keep them up, to succeed. An 'amateur' isn't someone who does a job badly - as many might assume - but, literally, someone who loves an activity (coming from the French 'lover of...'). Every side-project still is a project and, as such, takes work. Not all of it will be enjoyable all the time. To take it places, you must love it. Not unlike an actual pet that occasionally litters the carpet, but that we can't really be mad at.

2. Write down your objective
   Now that you're clear on what drives you, you might find it useful to actually put into words what it is you are trying to achieve. What's the purpose of your pursuit? It's fine for this to be purely self-motivated like having a creative outlet or developing a craft. Or it might be focused on others, such as building a community, helping others through what you're creating, or having a self-made gift ready for grandma each time you need one.
   At this stage, this doesn't have to be extremely refined or structured, but pen a sentence that feels right. Write a few drafts of this. It is less about the statement you end up with, and more about the process of getting there through iteration until you no longer feel like you could change it.

3. Consider alternatives
   If you've identified an area of activities you have the energy for and that you love, you may have a specific idea in your mind of what exactly it is you'd like produce. If this is the case it may be worth thinking a little longer and harder. Ask yourself if this really is the thing you need to do, or just your first-best idea. I'm all for using your momentum and getting started, but it is often worth taking another moment to come up with alternative ideas. Just to be safe.

4. Set milestones
   You've thought about the larger purpose of your project already. Now it is time to get a little more specific. There are many frameworks you can use: I like OKRs, others prefer SMART goals. You don't need to be a scientist about it, but it may help to set objectively quantifiable targets you can measure yourself against

5. Gauge the commitment
   You have energy, and passion, and an objective. But what about your time-commitment? Is this something you'd like to have a go at just once, or a longer-term pursuit? Either is fine, but be honest to yourself about how long you think you can keep something up for. Some initiatives require you to stick with them for an extended period. If you're not truly prepared, dedicated, and able to do so, you may need to go back to the drawing board. There's no point starting a garden when you have only one free Summer ahead of you. Some things only flourish with time.

6. Get unstuck and begin
   Two of the main reasons I see for projects to never really take off properly are too much procrastination - giving attention and time to seemingly related tasks you could actually do without - and an excess of planning - really just another type of procrastination, come to think of it. Too many good ideas died in a meeting room or a notebook. To let an idea develop and grow, there often is little use in trying to plan and anticipate future scenarios from a certain point on (with a few obvious exceptions where you have to get things right the first time around). While some basic thinking around goals and motivations is helpful, I often recommend against worrying about a plan too much. Just get started, do what you can do today. Get more excitement from it, and see what you learn. Then let those lessons grow into a plan or even strategy along the way.

7. Tell others
   Even with pet projects, things won't always be 100 per cent enjoyable. To save yourself from quitting at the first sign of adversity, you'll need to hold yourself accountable through goals, but what's even more powerful is making others hold you accountable for reaching them too. You don't even need a creative personal trainer. Just telling others about what you are intending to do, and the fear of embarrassment when having to admit you didn't follow through, will help keep you on track. And it will bring you encouragement when celebrating successes.

8. Do the work and maximise pay-off
   With many creative activities, part of what keeps you busy is working on your thing, another part may be about what that thing can do for you once it exists. If you write, paint, make music, knit, or develop a side business, many (if not most) projects may start as being created solely for their own sake, but ultimately target others. Whether we want to become known for something, or just want to get our work in front of as many people as possible, there will be work involved in getting there.
   If you make things for the internet, distribute it across platforms. If you want to share it with your friends, take photos and email them. If you want to sell things, you may want to advertise them. If you hold a group event like a Meetup, take recordings and share some relevant content.
   Examples are endless. The point is that often, for a project to fulfil its purpose, you'll need to balance working on it with those other jobs that will grow its impact.

9. Find collaborators
   If you're an introvert like me, you may have a tendency to tinker away on your own and keep your work to yourself. Don't forget tough, that no person is an island. Quite often, there are others around us who may share your passion, or hold a complimentary one. Maybe there are people who simply dig what you are doing and don't mind helping you out on some front. Take a look around. You may find that even your personal pet project is better together.

10. Give it time
    Most things don't pay off right away, but take prolonged commitment, dedication, and patience. This is true especially in the web.
    One friend of mine started a jobs board, laboriously gathering roles she could find and sending them to her subscribers. At the start, this was a mere dozen of former colleagues. For an entire year, her project experienced minimal growth staying in the double digits of subscribers. Then, suddenly, things took off. The magical and mysterious multiplying network effects of the internet kicked in and within a few weeks, her board gained thousands of subscribers. Today, another six months later, it is the worlds largest jobs distribution board in her industry.
    It is this story that made me set most goals with a minimum horizon of one year. Patience and determination are often more valuable than any other attribute - even talent.