This is a great thread, and I hope it stays going for a while. It’s always such a big question.
I’ve recently done both: Jump in whole hog with a string of products, as well as work on my side project/products along side a full time contracting gig.
The biggest problem I face is that I love programming and engineering challenges. I get paid more than I thought I ever would when I got into software development, and I get paid to do something I love. But at the same time, I quickly get tired of working on other people’s products.
At the end of 2011 I quit the best contracting gig I had ever had at that point to go full time on a product. The product didn’t work out, and my partner and I jumped through two more before running out of money in early 2013. Through a long series of unfortunate events, including two deaths in my family, and litigation from a past client (the only time that has ever happened to me), we just never got the momentum you’re supposed to get when you go full time on your project.
Now I have a great job, with an awesome team of people, but I’m so engrossed in it, that all my work on my own products has ground to a halt. I keep telling myself that I’ll get ahead and ease back my hours, but can’t seem to pull myself away from it. I need to set some limits on the time I spend working on other people’s products, so that I can spend time with my family and my own products.
I’ve decided, for a developer/entrepreneur, working on a product is like an investment. You have to discipline yourself to keep putting those dimes and nickles into the bank, and making good trading decisions for the stocks you own, admitting to yourself when you’re wrong, change course when need be, so that you have some sizable assets to work from in the future.
@patio11 does this better than just about anybody I’ve ever seen on the interwebs.