Having freelanced since the first dotcom crash, this reminds me a lot of my own financial anxieties early on. I responded by going super-risk averse in exchang

Having freelanced since the first dotcom crash, this reminds me a lot of my own financial anxieties early on. I responded by going super-risk averse in exchange for embracing the riskier income model. For those that are starting out freelancing, the best advice I can give: You're entitled to nothing! All you will have is what you earn, and you have to keep your sense of accountability. If you find yourself stretching your resources to buy something because you think you deserve it, remind yourself that (in the words of Clint Eastwood) "deserve's got nothing to do with it." Freelance cash is great, but it's a bit of a mirage, because security is far more valuable than a recurring fat check that might stop recurring. Random rough example: 3 years of guaranteed 5k/month is actually more valuable (on average) than a monthly 10k check that has a 5% chance of ceasing each month, assuming no further employment chances for the remainder of the three years. My order of priority was always: bare minimum of expenses, max out retirement, emergency fund, and then balancing my desire to increase standard of living with my desire to save. Also remember that buying luxuries has a nasty way of also increasing your ongoing expenses. I tried to aim for an emergency fund of a year, which meant keeping expenses low as much as it meant saving a pile of money. Volatile investments can make you richer faster, but they also have an increased probability of dropping you below zero, and that's why you must be conservative until you can afford to risk your capital. That applies even more to leveraged investments like taking out a mortgage for a rental property. Last priority should be purchases that don't make you any money - I'm currently making more than the OP topped out at in his article, but I still drive the same pickup truck I bought in the late 90's, because I personally don't need anything nicer-looking. I work from my laptop for clients that don't care what I drive. This isn't to lecture the OP - he had his own circumstances and one hell of a humbling experience - more power to him for making his way through it. But if you're a 20-something freelancer that thinks you're doing well just because you're on a 100k projected revenue... please think again. :)