[chasing]

I've been freelancing since 1997. It has its perks, for sure, but it's not simply "become a freelancer, work two hours a day, fulfill all your dreams!" That's as much of a stereotype as "become a freelancer, work in your underwear, never take a shower!"

Making a good income as a freelancer requires work. And clients. And paying attention to clients' needs. And spending much more time organizing your financial and business life. And dealing with work/life boundary issues. It's something I like to refer as a "job."

And he's certainly not "retired," as he seems to claim, if he's paying the bills freelancing. It kind of sounds like he's decided to take a major income hit in order to have more lifestyle freedom (aided by living in a place with lower costs of living). Which is totally fine! Especially when you're young. But that's a major trade-off, and not one that should be taken lightly.

[orangethirty]

Spot on. I will add that freelancing is a business. Thus it survives or thrives on the marketing. If you suck at marketing or hate to do it, you won't do as well. That's why I sell a marketing system for freelancers. Most are simply lost when it comes to it.

[budowski]

I have actually written about the pros and cons of freelancing in a previous post, showing that it's not all rosy: bucketlistjournal.com/post/46601822485/pros-and-cons-of-freelancing

(and P.S. - I personally did not relocate, so my living expenses are still high)

[chasing]

You seem like a good guy and I agree that balancing work and lifestyle is crucially important -- especially in an industry like ours that tends to like to grind people into the ground with mirages of fame and fortune. [Edit: Mixed metaphor. Sorry.]

But. You come off as someone who has just barely started thinking about these issues. You're being wildly overly simplistic about how freelancing works in real life. And using the skydiving billboard as a trigger makes it sound like "living your dreams" means doing extreme sports and hanging out on the beach. Which is fine, but kind of shallow and definitely not the end-all be-all of a well-lived life.

[pbreit]

I didn't get that sense at all. What I took away from the post was a) in sad of packing your days with work now so you can do the things you want in 20-40 years, structure your life so you can do those things now and b) freelancing could be an option (but its not easy).

[rhizome]

It makes sense if you take a step back and see this as a play for the ol' "blog to book deal" business model. Jumble up your thoughts and experiences, slice and dice them into a couple hundred posts and maybe it'll look like sales-in-waiting to some acquisitions editor.