Ask YC: Are you working on your startup/side-project strictly in your spare time?

6 and 5 are closely related. The way it worked for me was to

  (a) generate and *polish* the idea; 
    (1) make sure it is technically sound
    (2) not trivial, i.e. not easy to copy
    (3) maps well on business opportunities
    (4) does not have IP (patents, licenses, etc) problems

  (b) implement it about 80-90% through, prepare solid beta
  (c) release beta and see how it's does
  (d) if all goes well, evaluate the progress and estimate how long until the first revenue comes in

Steps (a.2) and (a.3) filter out A LOT of ideas. Step (b) also tends to screw things up as some ideas work out to be hard or even impossible to implement alone or on a modest budget. Steps (c) and (d) are pretty much the last mile before the full-time involvement. If the idea was thought through, the chances of failure on last two steps are not very high.

So I'd say 2+5+6 (+8) is the combination I had. Step (a) took about 2 years, (b) - under a year, (c) - 6 months. Your mileage may obviously vary :)

Just curious - was a.2 something you felt like you HAD to achieve? There's tons of examples of copycat apps out there; some are just better executed than others.

I like what you said about overall portfolio - while my main focus now is to continually improve my technical skills (I work with Rails and learn new things quite often), in the long run it is best to be well-rounded. I'm interested in learning more about business, stock and real-estate investing, and learning to speak new languages.

Of the options you offer, 2, 3 & 6, but I'm also finding the most important benefits of full-time contracting is it's a great way to meet like-minded people who could become collaborators or investors in my business.

I guess also, it's good way to stay in a positive frame of mind. In our first go at running a business, we had no idea what we were doing and after 2-3 years killing ourselves on the startup we ended up broke & depressed. If success breeds success equally failure can breed failure, and after enough time spent with that smell of 'loser' about you, you start to lose the respect of your peers and question your own worth.

It's taken me 2 years to get back on my feet to a point where life is going really well, and I'm enjoying success both in my day job and my startup. Whilst I'd love to quit full time work and focus on the startup (which I may be able to do soon with funding from some of the people I've worked for), having a day job has been great in getting the startup happening. By not relying on it for your living you have more freedom to do it right for the long term, and even if things are tough with the startup, your judgment isn't clouded by panic.

"Fear of failure" should be on the list. A lot of people don't know how to deal with failure. Some will let it ruin them, others will rebound as you did.

Those that rebound will have undoubtedly learned valuable lessons for their next try. For people in certain situations and certain stages in life, this is too big of a risk. Failure cannot be an option.