The only big problem is that you don't seem to have much of a plan to make this sustainable in any way dan. I think you should try and do some contracting since that is the easiest way to transition away from the 9-5 full time job trap. While you do that you should also be making your own stuff that you think could generate some revenue and also plan a kickstarter for a separate larger initiative. Basically do not put your eggs in any single basket but have a larger portfolio to mitigate risk. The only thing is that you should've been doing these smaller projects on the side for the last year to give you more of a cushion.

This is basically exactly what I did in the past year and all of these strategies succeeded for me so I have gotten into a pretty good position. I now have a thriving contracting business with 2 other employees, a successful kickstarter(we raised around 150k) with 3 other main partners in a separate company, and between $500-1000/mo of passive revenue from some of my smaller projects(to be fair though I have been working on those projects on the side for the last 2 years, originally they made significantly more than 500-1k/mo, they have just slowed down a lot). I spend my days mostly on the kickstarter.

The most important part of this is that any one of them can fail at any time and I will not freak out. Some of what you do will fail, even if you feel in your gut 100% sure it will succeed there is still a very real chance it will fail. Some of my smaller projects failed spectacularly. You need to be prepared for this and have a plan to mitigate these failures.

It is not easy to escape from full time work in a sustainable way. You have to work at it and you have to have a plan. You also need some luck.

Also if you live in san francisco, new york, dc or london you need to seriously consider moving away. The problem with selling products on the internet is that your earnings in no way reflect your geographical location, and it is much harder to succeed when you are spending way too much on everything.

Edit: Apparently you live in London. Trying to bootstrap in the most expensive place in the world is very hard, I would advise trying to contract locally where companies will be more willing to spend above average for developers.

I am especially glad that we are agreed about "It's better to take part-time work that pays the bills than it is to take full-time work that gives you lots of disposable income. Your time is far more valuable than anything any employer will be willing to give you."

As for failing: yeah, you're probably right. There is a high chance that I will not be able to keep this up forever. Part-time work and freelancing may sustain me for a while, possibly even extend my 6 month runway - but I need to find something more stable and/or large in terms of amount-of-money-to-live-on.

But I'm glad you also agree that even if I do go back to a 9-5 job, I will find a lot in this lifestyle which I enjoy and can learn from. And maybe if/when that happens, I will be excited about returning to that lifestyle I formerly had. After all, there are many enjoyable lifestyles and the "9-5" can be one of them.

I promise I won't rely on credit cards, and I promise I will stay open to opportunities. The man who I mentioned in the post, Mike Rugnetta [1] told me "Say yes to everything you can at first. Then, eventually, you will be able to say no." - I hope he is right.

Finally I love your suggestion about alternative sleep/work patterns. Personally I think I'm likely to adopt an early-riser thing. I'm very into bouldering, and the best time to go to the climbing wall is in the morning at 6:30am. I would love to get to a point where I regularly get up at 5am, but I'm not quite there yet. I guess we shall see where this takes me.

Thank you, moron4hire - I appreciate your honesty and your well-wishing :)

[1]: http://twitter.com/mikerugnetta

That's my plan at least: replace my day job with a freelancing gig, which should afford me enough time to build out the ideas I have. I actually wrote a blog post about it recently [1] and I have high hopes for it! Hopefully I can be like you some time next year and take the plunge!

[1] http://blog.mcdougle.net/creating-acquiring-software-assets/

The successful diet--and the successful non-traditional career path--rests on accepting the new lifestyle as the norm, as natural, as default. That which was the old way must become the exceptional case.

The journey through the wilderness requires many skills. You can't be thinking about the river you crossed to get to the desert, and you can't be thinking about the mountain you'll climb once through the desert. Be present in your work.

I still have family members who think "this freelancing thing" is just a temporary stop-gap until I find "a real job". They have no concept that the freelancing could be an end unto itself. I don't want to be a freelancer for the rest of my life. At some point, I'd prefer to get out of services and into products. It might not even be software, I have been receiving more interest in my artwork this year than I have ever in all previous years.

But that's down the road. Right now, I'm a freelancer.

Okay, flowery language aside: unfortunately, it's really easy to take on too much freelancing. It's really easy to rationalize, "oh, the client needs the extra effort right now, and at least they're paying, but we'll go back to normal after this, because they're paying." Well, clients are as adverse to change as everyone else is. It's easier for them to keep paying that extra rate than to accept the lesser productivity.

Plus, as far as your body and your mental willpower is concerned, the work is indistinguishable from your project you hope to pull off. You'll be working hours for your clients be right back in the situation you're in working for The Man: not enough energy to work on your side projects, beholden to someone else's schedule.

That's why I suggested completely unrelated work for temporary sustenance. Bartending, cooking, dog walking, what have you. They usually lack the ability for you to decide to work more. The very nature of the work prevents you from sabotaging yourself.

Incidentally, that's why I'm pouring more effort into the freelancing. I'll turn the freelancing into B2B consulting. I've got a couple of subcontractors working for me. I manage their work directly. My clients don't even talk to them. They know about them, they know that they are paying me and I'm paying someone else to do some of the work. But they also know that it's the only way they're going to get more done on the project in less time. Right now, I personally am the biggest chunk of what the client receives. If I can build this large enough, then taking myself out of the coding, at least, shouldn't have that big of an impact to the overall workflow.

So for now, I'm a freelancer.

I don't think I plan to do freelancing simply as a "stop-gap." We'll see how my mindset changes as time goes on, but I do hope to actually build a business out of it -- make a good living myself for a while, then hire teams, work on bigger projects, etc. Like I say in my blog post, I will be just creating another job, but it will hopefully be a job on my own terms, essentially. There are the issues you mention -- easy to pick up more work, etc -- but I can do it at my own pace and on my own time.

Building software products are, to me, like investing -- building a separate source of income. I'd love to have many different sources of income, one of them being freelancing. I assume once my "investments" can sustain me -- and, as time goes on, I end up with more responsibilities (like a family) I may cut back on the freelancing thing. But for now it sounds great.

My point for the OP was that I do think he can sustain himself indefinitely on things like freelancing or part-time jobs that allow him more time to focus on his projects. You do have a point though -- it might not be a bad idea for someone in his position to pick up an unrelated job like bartending.

Even if everything every naysayer says is 100% true, it's still worth the experience. It's still worth testing yourself.

I personally found that I work hardest for myself. I work best when I understand the rationale for doing what I'm asked, and when I ask myself to do the thing, then I completely and fully understand the rationale. The surest way to get me to not do something is to tell me "because I said so." When asked why I won't, I'll most likely reply, "because fuck you." To me, the two are equally legitimate and reasoned arguments and are completely deserving of each other.

I also was not personally able to do the "side project" thing. "Just work 10 to 15 hours on top of the 70 you're already working for The Man and the 10 you're commuting and why don't you spend any more time with your friends and what is wrong with you and your health, why can't you take care of yourself and get enough sleep and eat properly and exercise and setup time to talk to this financial planner I've been telling you about for the last 3 days, you just seem like you're drifting." (can you tell I lived at home too long?) If something is worth doing, I believe in spending my entire effort on it.

Mistakes are meant for making, because most of the time they aren't mistakes.

My best friend just started this journey for himself as well. He is married, they are upside-down on their mortgage, and they just had a kid. He quit his job in finance to become a photographer. It sounds like the absolute worst mistake he could possibly make. He got his first sale inside of a month. He's received a few accolades for his work. He would have never gotten there while still working for The Man. Even if he has to get a job in a couple of months, he knows his metal now. He knows it's just a matter of time before he gets to do it again.

And that's called hope.

^^^ that