The amazing Derek Sivers recently published an article about doing what you love and making good money. The article is outstanding, and I agree with it by the most part. The gist of his idea is that it is better to have a good paying job while pursuing your artistic career. If you choose one over the other, you’ll have too little money, or too little purpose.
Here I just wanted to write some observations of stuff that has worked for me:

• It is very helpful to know how much money you need to earn per month. The essential thing is to broadly track your expenses and make sure that you earn as much as you spend (ideally 10% more, so you save every month). But the essence here is to have an income that will let you sleep at night and finish the month without struggling.
• For your target salary, the ideal would be to find a job that:
  • Fulfills the target income.
  • Does it part-time, so you have half your day to spend in your art or true calling.
  • You don’t hate.
  • Within an organization whose purpose and effects in the world you don’t consider hateful.
• These kinds of jobs, in all likelihood:
  • Will have a market premium and be in high demand.
  • Will be freelance instead of a permanent contract.
  • They should be amenable to part-time and a flexible schedule (even remote working).
  • Directly add value to your customers or employers – this justifies why they pay you well and they let you work flexibly.
  • You are safe in this path in the measure that your skills are vaulable and properly deployed – but you’ll be eschewing the traditional security of a full-time contract. This will tickle positively the risk-loving part of your brain.
• Use a timer for tracking how much time you spend on both types of work:
  • Know how much you’re working for money, even if your employer/customer doesn’t care.
  • Know how much you’re working on your own stuff.
• Have limits:
  • I find that in a given day, 3-5 hours of focused work is all that I can ask from my brain.
  • You’ll probably spend close to 100% of your creative work in a state of focus; with paid work, it can be around 50% (there’s always emails and meetings and planning). The 3-5 hour limit has to accomodate both kinds of work.
  • Relax and recharge in the evenings.
• Embrace the double life:
  • There’s inspiration to be found in “non-creative” work. Your creative mind needs more than focus to thrive – inspiration can come from unusual sources too. Many of the best minds did their best work while leading double lives.
  • Even if your creative work starts to pay the bills and you can quit the other job, you’ll probably start seeing your creative work split in two, a part that’s more creative than the other.
  • Long-term progress is seeing your creative part of work divide into two parts, one of them overtaking the former “working” part. Think of it as a multi-year mitosis cycle.
  • Love your colleagues and your paid work. Be grateful for having enough money and not having to destroy your body, mind and soul in pursue of sustenance. In today’s world, this is not to be taken for granted. And gratefulness is good anyway.
• Alternatives to the double life:
  • Become a millionare and retire young – extreme focus on money, for a short amount of time.
  • Focus exclusively on my passion and try to make my living out of it – extreme focus on passion, until you “make it”.
  • Working mindlessly while dreaming about being an artist is not a real alternative. You can do better.
• There’s more to life than a double life:
  • Sleep.
  • Meditate.
  • Workout.
  • Learn a language.
  • Cultivate your family & friends.