Making 2019 the year for Side Project success


Photo by Frederick Medina on Unsplash

Happy New Year!

Let’s try and start 2019 as I mean to go on; with a few more regular side project blogs! Developing good habits kicks the arse of goal-setting, so this is me trying to start a habit for the new year.

Here’s my pitch: I increasingly believe that a having a side-project is good for your sanity, your health, your career, your relationships, and life in general. Below are 10 key tips and tactics for finding and developing a great side project in 2019.

#1 Sanity and Self-Belief

In an increasingly on-demand world in which we’re constantly holding ourselves to or being held against the benchmarks set by the rest of humanity it’s easy to feel like we’re struggling to live up to expectation. Finding a thing that you just care about, that is just interesting and fulfilling can be both a balm and a wellspring of motivation when everything else can be going to hell.

Lavishing time and attention on something that you can get better at and that provides regular ‘slow success’ and personal development can give you a powerful sense that something is within your control and that you can ‘own’ it. This can be a great psychological anchor, a thing to retreat into, or be proud of, when you need to remember who you are beyond job titles and social bench-marking.

Imagine for a moment that your sense of who you are and what you do is propped up by a series of pillars; these might be your job, your family, and your friends. Inevitably one or more of these will fall from time to time. Why not build another pillar to help prop you up, why not have another dimension to how you frame your well-being? One that is less susceptible to the whims of others? Maybe that’s a side project (thanks to Kathy Freeman for sparking the visual metaphor for this).

#2 Creative Expression

I’ve discussed this before. However, the essence is that a lot of people get a lot of satisfaction from making/writing/playing/building/painting/doing things. Even those of us without the specific skill or talent can have fun creating. What we create might not be objectively any good, but it was probably fun and satisfying to do it – and that’s enough. However, we can also get better through practice – and whilst that has frustrations it also has rewards; approaching mastery and attracting praise are great rewards. Even for the talented people the act of creating for your own pleasure can be something of a rarity. If we’re normally using our talents to get paid by supplying products or services for others then being able to create for ourselves can be a wonderfully rewarding thing that reinforces our sense of self identity, our self-efficacy, and ultimately our well-being.

#3 Career Progression

Building on that last point, side projects are a great place to develop new and extend existing skills and interests that just don’t get done on the day job. However, if you’re trying to move up or on from an existing role how do you find the time to learn what it is you need to get progression or make yourself credible in a career-shift? Side projects again provide a vehicle for exploring interests, developing skills, and showcasing ability that can evidence your capabilities. My previous blogs featuring Gav Strange and Sam Fry are great examples of people using side projects as stepping stones.

#4 Don’t do it for the money

As Gav Strange told me: “Money is not important at all, although that’s because I’ve never really had any money! When people start paying me it’s a job, not a project, so I don’t like people paying me. I already have a job! I also don’t like having that emotional responsibility to someone else; I can let my own expectations down – but not other people’s.”

Yes, you can turn a profit from a side-project; almost all start-ups start as some kind of side project in fact. But that’s not the point; in fact, as Gav suggests the process of finding and servicing customers can actually rob you of the opportunities for fun, development, and purpose that a side project can provide. Obviously if you can make it all align that’s amazing (that’s Ikigai) but don’t initially get hung up on turning a profit.

#5 Find something that fascinates you

So, what should your side project be? The chances are you’re already thinking or doing something about it; what articles do you find yourself reading online that might be a surprise to work colleagues or even your friends and family? What shops, activities, sports, performances, products always attract a little fascination when you see them?

However, sometimes it takes a little lateral thinking too – your ‘wish-list’ projects might be initially too expensive in resources or time, or unapproachable in some way – but maybe there are more accessible or less demanding alternatives that hit the same buttons? My 4-year old wants to learn to play the tuba, which is probably bigger than she is, but we can prototype the experience of playing music on a recorder or a trumpet to see if she enjoys the process.


Photo by Annie Spratt on Unsplash

#6 Diet and exercise

Thinking about creative strategies I’ve talked about this before too; but the core premise is that you need to feed your brain some inspiring content and ideas and you need to regularly flex your creative muscles to make the most of all that good content you’re now consuming. “Garbage in equals garbage out” as they say; so, start reading content about people, places, activities, and things that interest you and provoke you, stop reading the things in your comfort zone, and experiment a little until you find something that works.

#7 Do (or continue) something/anything

Stop thinking about and start acting on it; assume that it may not be perfect or even work at all, be ready to sustain failure on route to somewhere interesting. I heard the writer David Sedaris say (something like) “everyone has thousands of crap words to write before they write anything good, but unless you get the crap ones out on a page you won’t get to the good ones” so get started and clear out all the crap writing/making/doing/trying and you will get to the satisfying and rewarding ones – but it will require some perseverance.

On a related note, and I used this anecdote in my TEDxCorsham talk, an entrepreneur I met once suggested that the psychological step of ‘starting something’ always felt really intimidating even when he’d started many projects before. That moment you commit to a new thing was always scary when you built it up in your mind. Instead he suggested that new ventures start the first time you thought about them, the very first inkling of an idea. i.e. that the first step was practically accidental, it happened so easily you barely noticed. So, you’re never making the big step, you’ve already started, now you’re just exploring and developing something you’re already committed to. Using that logic, you have actually already begun dozens of ventures – you just haven’t finished them yet…

#8 Share

Again, a theme I’ve discussed elsewhere, but sharing your thinking/doing about a side project is always catalytic. It might be created a ‘verbal contract’ with someone else that helps you commit to a project, it might be getting permission from a key stakeholder to spend some time on it (i.e. your family), it might be someone else going “that’s amazing – I’d love to be able to do/see/hear that!” which validates you a little, it might also be finding a collaborator/network/supporter who enables you to really move forward. Dare to share and it’ll pay off.

#9 Be ready to start at the beginning

I’ve mentioned failure already. I don’t think you can start a side project and expect to master it rapidly, in fact that wouldn’t even be very satisfying. The best side projects use a measure of existing skill and talent and a measure of learning new things and developing new skills. My case studies Holly Pearson and Duncan McKean would be good examples here; they had some of the skills but absolutely learnt new ones too.

The mix is important though; you’ll need a lot of passion/interest to keep going through steep learning curves, you might benefit from confidence acquired through existing skills or early successes to get you through more challenging or demanding periods when it isn’t as easy. These parameters are very personal and hard to quantify for each person and each project; trial and error is a level of failure you’ll need to sustain. Maybe that’s another reason for not making it about the money.

#10 “Goals are for losers, systems are for winners”.

So says Dilbert creator Scott Adams; his point being that goals are temporary and fleeting, whereas developing successful systems (that allow you to meet goals) are more enduring and more useful. I’d explicitly connect this to developing good habits that just help get stuff done (regardless of what the stuff is). Habits also allow you to stay agile to new and changing opportunities when a goal’s purpose might have become redundant. So don’t set goals for side projects, just set aside productive time to explore and do and see what feels satisfying and productive.

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