Have you ever worked hard on something that did not pay off?

Sure. Ten of the Twelve SaaS products that I have built over the years didn’t get any traction and died away. That’s only counting ones I spent at least a month or so head down building and marketing.

And that’s fine. Because the other two pay the bills.

That’s the cool thing about software businesses. You only need to get it all right once. People like to call this “survivorship bias” and other silly things in order to convince themselves that it’s pointless to try. But all it really means is that you get to keep trying until it works.

As the lone IT guy, I built a new database to upgrade/replace the production system, it would have saved hundreds of hours of labor, but couldn't get buy in from management.

I had conversion scripts that worked, a reasonable plan for recovery if it didn't work.

I tried a few other projects, but eventually settled in to just showing up and waiting for things to break. It broke my spirit.

I lived off my savings for 3 years and put 120% of my income in the company, nailed $7m deal (and other big ones were to come) when my partner scammed and screwed everything and everyone. needles to say he got sued for not nearly enough. the deal dropped and "luckily" we didn't get the money yet, otherwise I'd be in bigger trouble.

My search engine and aggregator locserendipity.com has not gotten much traction despite many hours of work. Even so, I have learned a lot from working on it, including a working familiarity with multiple languages. I have also learned that others are not as interested in history, puns, classic radio, and other resources.

In my experience a better question would have been. "Have you worked hard on something that DID pay off???" Most of the things that we work hard on never pay off except in terms of learned lessons.

Quite frequently in enterprise software I've built something that has either been replaced soon after or a 3rd party has been brought in with a product or our product has been discontinued. Usually this is nothing to do with the technical side of the project and is down to finances/support arrangements/strategy. I still got the same experience building it whether it was successful or not and I still got paid so not too bad. Conversely some things I've built/worked on have still been in use 20 years later...

My masters degree was a waste of time.

I worked on a diet/fitness gamification startup for 2 years. Built an iPhone app and a website with a fleshed out back-end. Spent around $50k of my own money for design, and coding help. Even built a list of 5000 users before launching, but it still didn’t work out at the end.

Prior to that, I hacked on a site that helped you outsource your shopping. Toiled for a few years, spent close to $25k of my own money, and made maybe $1 in total income.

I spent 12 years playing football as a kid almost daily and didn‘t make one $, does that count?

I probably poured a little more effort into programming than I should have

yes most/all of my side projects :D

but i dont mind as much.

In my professional lifetime, I have developed several technologies. Most of them as a hobby, and about 90% become fully functional and production ready.

Some of them got sold; some others went nowhere. Overall, those projects have not made me much direct income - I can develop technology but I am terrible at selling stuff (actually, I am not so sure if I am bad at selling because I have zero interest, and the effort that I made to sell is quite proportional to the interest that I have).

However, all those projects allowed me to have a better understanding of many different facets of software development, and my actual area of expertise is quite deeper and broader compared with other professionals of similar background and years of experience.

It has also allowed me to get to know a lot of people, become a technology speaker, and perform many risky experiments - which I wouldn't dare to do when I am hired in another businesses - which provides me a unique insight on how to actually develop technology (for example, all those experiments confirms that if you are not using data driven approach to make decisions you are being massively inefficient).

Eventually, I decided to go full on with one project related to infrastructure automation (this topic is really cool!!!!). This project evolved to consulting services. The interesting part is that this project is quite interesting and well put together (although sometimes a bit hard to get started) but once you have set it up it is amazing, as I have confirmed with many consulting clients. But when I think about actually selling it, the excitement collapses quickly. I just tell people about this solution when I am requested to solve the problem by the client. (if anybody is interested the project is manageacloud.com, although there is a price structure I am actually not charging anyone).

Did I waste time with this project ? Well, it provided me with a direct income. Allowed me to show expertise to speak in several big technology conferences, and I got around 15 (yes, unfortunately not kidding) interviews with Google where somebody internally got the position(s) Google suggested to me until those interviews were becoming routine. I have managed to work from home for 6 years with consulting services, in very interesting projects, in huge business and well funded start-ups.

Working from home has allowed me to do some crazy stuff such as become black belt and fight in full contact international competitions. This would have been much harder with a 9 to 5 job, without the freedom to work whenever I can.

Are you thinking of making a project ? Throw it all away and go full on for it? Just do it. Why not ?

What will you think of yourself 10 years from now, knowing you had the opportunity and didn’t do it ? Asking yourself what would have happen? I cannot live with this thought.

What is the worst that can happen? Well, I am going to rephrase: How hard would it be for you to find a position similar to the one that you have right now?

Go for it. Well, actually, if you don’t have debt go for it. If you have debt … then it depends.