Freelancing and Lifestyle Design

A few weeks ago, I saw these huge billboard ads selling pension funds: An elderly couple doing skydiving, with the text “For retirement to look like what you’ve always planned for, use <company-name>”.

This really pissed me off. Most of us go on with our lives, working our ass off for 40 years so we could save enough for retirement, and only then do what we’ve always wanted. By then many of our dreams will become irrelevant. Frankly, we’re most likely to become institutionalized – not knowing what to do on a day-to-day basis during retirement. This is what Tim Ferris calls in his book (affiliate link) “Deferred life plan”.

Lifestyle design is about pursuing your dreams and passion right now. Not in 40 years. Not grinding away hoping that some day you might have enough time and money to do what you want.

“Easier said than done”, you might say. Indeed. Especially when you have so much obligations and not enough cash. When you can’t even free up a single day a week to do what you want, since you’d simply become jobless.

This is where freelancing comes in. Simply put, freelancing allows you to have a very flexible work schedule, a lot more free time, while generating more income than you did as an employee.

Sounds like a cheap sales pitch, I know. It’s not easy getting there. And not everything is as rosy as it sounds. But you can start your journey now. Not in a few years when you’ll be more “financially stable”.

First, you need to decide what your ideal life style looks like and only then will you need to adjust your way of freelancing to support your desired lifestyle:

  • Traveling the world while working two days a week;
  • Working on a startup while freelancing until it takes off;
  • Relocating to Thailand’s Ko-Phangan while exploiting geographical arbitrage to have much lower living expenses and needing to work a lot less

So don’t wait 40 years to do skydiving. Book a skydiving lesson tomorrow.

(Note: I’m a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to

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