When undertaking a venture as crazy as mine, it’s very important to define success. Failure is a little more easy, it’s not success. I’ve put some time into thinking through this, and here’s what I’ve come up with.
I want to be able to work where I want, geographically. Of all the things I’ve discussed with my wife, this seems to be the most important bit. Of course I want to make enough money to pay the bills and put a bit by, but I’m not looking specifically to get rich. Working when I want is nice, but that only goes so far. I still have to work enough every day to get the job done, or else… failure.
Working on what I want only goes so far as well. On the one hand, I love web development, and I’m doing that, ergo, I’m working on what I want. On the other hand, there are elements of my career I don’t like (very long forms aren’t fun), but need to be done, so I do them. I’m very much looking forward to getting into new stuff too though.
Lastly, I really think this is God’s will for my life right now. If I do this, and in 2 years we’re bankrupt and lose the house and I get a day job for half the pay, will it be a failure? No, because I did what He wants me to do right now, and I’m happy to go down whatever road He wants me on.
In that light, I can’t fail, success is guaranteed. That’s a happy way to be.