For over 10 years I’ve made my living by: creating things, offering them to the world, and gratefully receiving any support given in return.  It’s been amazing, it’s been hard, and it’s been pretty much everywhere in between.

I operate quite a bit differently now than I did when starting out.  I’ve had some successes, I’ve had some failures and, along the way I’ve learned some things that would’ve been helpful to know on that fateful day I walked out the door of my regular job for the very last time.

So I thought I’d share them with you.

These are the 7 things I’d say to you if you told me you were thinking about quitting your job to strike out on your own.  Some are things you should already be doing, some are character traits you’ll need to cultivate.

(If you’re missing any, you may want to reconsider giving your boss the finger until you have patched those holes in your rowboat.)

Once all 7 are neatly shored up you’ll be fully ready to row your little heart out toward the questionable paradise of Independent island.

Sound good?  Awesome, let’s get to it.

The most important thing you must already be doing, is you must…

Sounds obvious?  That’s because it is. But make no bones about it.  This principle is the primary foundation upon which you will build your empire.

The most important bits are the last two.  You must be finishing things, and they must be good.

Everyone has ideas but (and I’m sorry to break this to you) ideas are worth nothing.  Likewise with things that are only started.  Starting is easy, starting is the fun, everyone starts stuff.

Remember: The two things that will set you apart are: the finishing and, the quality.

If you are doing this already, then good for you.  You’re already ahead of the pack.

But it doesn’t stop there.  Even if you’re prolifically finishing things of quality, you must then…

Business is not complicated.  At its root, business is simply the means of facilitating an exchange of value.  But even though the core concept is simple, there are still several skillsets you need to follow through on it.

Business is knowing how to find the people who can benefit from what you are offering.

Business is knowing how to present your offering in the right way, at the right time, in the right places.

Business is building a bridge between you and your audience which you can use to exchange value.

Most importantly, business is understanding how to best serve others.

If you have no interest in business and just want to make your art in a garret flat in Paris then you have a hobby not a career.  If you want to make your living doing something unusual you (or someone you employ) must be able to exchange what you offer for money and other resources. This is non-negotiable.

These two things are a fine base, but they are not enough.  Once you have them both down, you need to….

Working for yourself is pretty cool.  Making art for a living is pretty cool.  But if you want to do anything with it, you have to work very, very hard.  And, joyeous or not, hard work is still hard work.

(Plus, now you have this business thing to take care of which is basically another full time job so… you quit one job and now you have two?  Mazel tov!)

The unvarnished truth is: doing what I do for a living is harder than any regular job I’ve ever held and comes with more challenges.  I still finish my days feeling spent.  There is no delineation between work time and home time, so I have to take care of that myself.  There is more stress because everything depends on me.

The difference that makes a difference is: in regular jobs I always felt that I’d given, but hadn’t got anything back; whereas now, at the end of each day I feel I’ve made something I get to keep.  My day no longer goes down in debt.

For me, this is worth the hard work.  Whether it is for you is a question only you can answer.

It’s a lot, right?

But don’t worry, I have some *great* news for you.

While you making and finishing things, being a consumate master of business, and working harder than you ever have before you’re also going have to….

One of the best pieces of advice I got when I was starting out is also the least sexy but here it is:

Want to be successful?  Minimise your outgoings.

Said differently: If you want to do the thing you love for a living you’re going to have to give some stuff up.

And the truth is: while giving up things to sacrifice for your art sounds romantic and beautiful and all that, when the rubber meets the road and you want that / latte / book / record / holiday / new set of clothes, it actually kind of sucks.

What’s that?  You want a thing? Tough noogies little artist monkey, money equals time and you need all the time you can lay your grimy creative paws on.

You must learn to be ruthless. With everything. Pare away the inessential.  Time is your most precious resource and Lean is the way.

The only thing this doesn’t apply to is good people.  You should not make of yourself a hermit.  In fact, you should consciously…

No-one can exist in a vacuum.  And if the greatest piece of art falls in a forest with no-one to hear it then it is worth precisely: Fuck All.

Whatever you make, be it a song, a table, a poem, a painting, or an electric car, that thing isn’t complete until you give it to someone else. Fact.

We’re all connected and making things is only half the circle. Giving that thing and receiving the support that flows back is the other half.  One feeds the other in a beautiful mutual dependency.

(It’s the Circle of Life…)

Your friends, your partner, your social group, the people who dig what you do, they’re all a part of the network in which you are a node.  You must become: skilled at finding those who will help, good at pruning those who subtract, and humble enough to accept the heartfelt support of those who wish to feed the thing you do.

But even if you follow all my previous suggestions to the letter, it’ll still not always be smooth sailing.  You must also learn to…

When he was asked about the most important qualities for a writer, George RR Martin (author of the Game of Thrones series) thought for a while, then replied:

“This is not a career for anyone who needs or values security.  It’s a career for gamblers.  There are many ups and downs.”

There are different kinds of gambling of course.  You can bet on games of pure chance (otherwise known as dumbfuckery) or you can place your bets in situations where you have some, but not all the information, like poker.

Making things and offering them to the world is much more like the latter than the former but nothing is guaranteed.  The most important thing you can do is strive to make the best decisions with the information you have.

After that it’s up to the Gods of chance.

No-one has 100% hit rate.  Each thing you do should be your best shot but no-one wins them all.  You need to be OK with that.

The last 6 are all things that will help you push on and push through, but this is not always the way.  Which is why lastly you need to…

Newsflash:  In your life there will be hard times.

No-matter what you do this will be true, but especially if you want to tread the path less travelled. Sometimes the work will be hard.  Sometimes, despite all of your efforts, all bets will fail.

Sometimes you will be dashed upon the rocks; hideously and unfairly beset by the storms and vicissitudes of capricious fate.

There is something to be said for the never-giving-up attitude but, along with this iron resolve, you must also nurture a sensitivity to tell you when you’ve strayed from your journey.

There is no glory in bullheadedly continuing down a path that leads nowhere. But there is also deserved shame in quitting something worthy solely because it seems too hard in the moment.

How to unravel this dichotomy?  You must learn to be as brutally honest with yourself as you can, whilst always listening to the counsel of your heart.

No-one can tell you when you should carry on or when you should quit, you can only make these decisions as consciously as you can, with the full measure of the gravity they deserve.

Always remember: your path is your path, meaning no-one can (or will) walk it but you.  So, in the words of Carlos Castenada:

โ€œMake sure it is path with heart.โ€

I cannot guarantee that if you follow these seven pieces of advice you’ll be successful, but I can tell you that each one will improve your odds dramatically.  I hope they help.

Be well,


Now Let’s Chat

What did you think of this post?  Was there anything you particularly liked?  Anything you’d add?

Make your thoughts know in the comments section (just below).

And Lastly:

If you’d like to stay in touch and join my little online community please sign up to the mailing list.  I send real letters, when I have meaningful things to share. There is no spam, just genuine connection, and mutual respect.

38 thoughts on “ Read This Before Quitting Your Day Job (or: 7 Things I’ve Learned Making Art For A Living) ”

  1. I have just found you and agree…..artist, hobbyist, business, isolation….determination, knowing when to stop…all such such good advice. One thing I have learned from my art….that my failures…the ones that just can’t find their way are not failures and no shame in them….but they are my teachers for the next work. My failures help me move to better work. Nice to meet you……..

    Liked by 1 person

    1. Really nice to meet you too.
      This is a crucial evolution. When you understand that ‘failures’ are just learnings, things can start to get very interesting… ;-)
      Have a great day.


  2. “Tough noogies little artist monkey” — this is the line I will carry forward in the torch of my existence. ๐Ÿ”ฅ๐Ÿ˜„๐Ÿ’๐Ÿ˜†๐Ÿ’ƒ๐Ÿผ

    Liked by 2 people

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