Posted On: Thursday, 23 October 2008 by Rajiv Popat

I've often been accused of being a pessimist. My pessimism comes back from the school days where I would announce, almost ceremoniously, how bad I had written my exam papers and how I might barely pass only to hit a 80+ or a A+ when the final results were announced.

My biggest strength at pessimism was that I was convincing at it. I could carry my pessimism tugged along with my depression using a very glum face; and I genuinely believed it too. If you were to put me on a lie detector and asked me how much I would score in that exam I probably would pass the lie detection test comfortably when I said I would just about scrap through or just about pass the exam. I would say that with a very serious and glum face.


Then I would go ahead and score a 80+ or an A+ when the results came out and you'd be wondering what just happened.

Acquaintances, teachers and most people who knew me considered pessimism to be one of my biggest weakness. They thought I was underestimating myself when all I was effectively doing with them was simple: I was lowering expectations.

When I entered the world of software development as a young an budding programmer and then a young and budding team lead, I realized that a little bit of optimism can make you your manager's pet and take you way ahead in your path to countless promotions and so-called-successful projects. I tried optimism and it sort of worked. I was successful but the success wasn't quite nearly as satisfying as I had expected.

I was frustrated; only to revert back to my true nature of a thick skinned pessimist who hopelessly under-promises, sells you the deal and then works his ass off to over deliver because he is freaking scared of failing in the end.

At work, I've been accused of being a pessimist by many. In past, I've been approached by Finance and Marketing people telling me that the organization had a long-pipeline of projects only to get my response that we should think about those projects only when the pipe line materializes and becomes real.

When it comes to recruitment and retention I'm continuously worried about my entire team quitting and on my feet to keep them happy; even when everything is perfectly fine. When it comes to projects I am constantly looking out for details which will cause the project to fail even when it's running comfortably well and three weeks ahead of time.

In an earlier post, I've already discussed my frustrations over being 90% done and have gone ahead and said that 90% done is as good as not done.

Pessimism is something that was always a deep rooted part of my character. However, I no longer consider it a weakens or something I need to work on changing.

If you're a programmer or connected to software development, Optimism and Wishful thinking are probably the two biggest vices you can be cursed with. Frederick P. Brooks in the classical legendary book, The Mythical Man-Month Essays on Software Engineering, explains:

All programmers are optimists. Perhaps this modern sorcery especially attracts  those who believe in happy endings and fairy god-mothers. Perhaps the hundreds of nitty frustrations drive away all but those who habitually focus on the end  goal.  Perhaps it is merely that computers are young, programmers are younger, and the young are always optimists. But however the selection process works, the result is indisputable: "This time it will surely run," or "I just found the last bug."

So the first false assumption that underlies the scheduling of systems programming is that all will go well, i.e.,  that each task will hike only as long as it  "ought" to take.

Steve McConnell in his book Rapid Application Development - Taming Wild Software Schedules believes that optimism taken at the next level of wishful thinking may be at the root of more software problems than all other causes combined:

I am amazed at how many problems in  software development boil down to wishful thinking. How many times have you heard statements like these from different people:

"None of the team members really believed  that they could complete the project according to the schedule they were given, but they thought that maybe if everyone worked hard, and nothing went wrong, and they got a few lucky breaks, they just might be able to pull it off."

"Our team  hasn't  done very much work to coordinate the  interfaces among the different parts of the product, but we've all been in good communication about  other  things, and the  interfaces are  relatively simple, so it'll probably take only a day or two to shake out the bugs."

"We know that we went with  the low-ball contractor on the database subsystem, and it was hard to see how they were going to  complete the work with the staffing levels they specified in their proposal. They didn't have as much experience as  some of the other contractors,  but maybe they can make up in energy what they lack in experience. They'll probably deliver on time."

"We don't need to show the final round of changes to the prototype to the customer. I'm sure we know what they want by now."

"The team is saying that it will take an extraordinary effort to meet the deadline, and they missed their first milestone by a few days, but I think they can bring this one in on time."

Wishful thinking isn't just optimism. It's closing your eyes and hoping something works when you have no reasonable basis for thinking it will. Wishful thinking at the beginning of a project leads to big blowups at the end of a project. It undermines meaningful planning and may be at the root of more software problems than all other causes combined.

Even after people with reputations as high as Steve and Frederick describe optimism and wishful thinking as one of the biggest problems of our industry I continue to be surprised by just how wishful people still exist in our industry.

I've seen companies continue on projects where the entire teams knew months in advance that the project would fail without doubt. I've seen teams continuing work on the project without uttering a word even when they were completely aware of the ultimate destiny of the project.

The decision to continue silently was clearly taken under the hope that something magical will happen whisking the project away on the path of heroic success.

I've worked at multiple client places. During my work at some of the clients, I've witnessed business deals being struck, companies being acquired and projects been extended all under the curse of wishful thinking when every single individual directly involved with the deal, the companies or the projects that I talk about, would have told you hands down that there was no way things could have "worked out".

Yet, the teams decided to continue; closing their eyes to the hardcore realities of failure. What they were doing was ignoring the possibilities of disaster outright blatantly.

Optimism and Wishful thinking are by far the Biggest Curse of Software Development and to a large extent and if you're working on a project where nothing seems to be going right and yet you find yourself continuing without uttering a word you're probably cursed too with these vices. Your only glimmer of hope is a touch of pessimism and every once in a while a splash of a cold water on your face to wake you up and show you the reality.

Remember, optimism and wishful thinking are the biggest curses in our industry. The next time you tell yourself that things will 'work out' ask yourself if you've genuinely evaluated the situation or are you just turning a blind eye to the inevitable?

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