OK, maybe failure is not an option

A week ago, I posted Failure is an option - more about Bob and Lisa. This follow-up to my WinExtra Kapost about Microsoft Bob made the following assertion:

NASA, then and now, engages in extremely complex tasks, and the outcome of those tasks can sometimes be deadly - something that prompted [Gene] Kranz's famous phrase, "Failure is not an option." Kranz's words certainly ring true when addressing life and death situations, but as many within both Apple and Microsoft know, failure can be the best thing that can happen to you, since it can sometimes spur you on to great success.

So failure IS an option.

Or is it?

Rob Diana recently shared some thoughts about how to report a problem to a superior. Diana's advice, which is echoed elsewhere, suggested that one should be prepared not only to report the problem, but to present some possible solutions to the problem. But then Diana went on to cite a Dave Winer post which linked to another Dave Winer post (from early August) which included the following:

I've been hearing all this happy talk about how great it is for Google that Wave failed. The theory being that if you fail that means you took a chance, and taking chances is good therefore failing is good.

This is really convoluted and it's really wrong.

The only way to succeed in my opinion is if you cannot visualize failure.

Winer's views are heavily shaped by his experience at Living Videotext in 1986. In this 1991 interview, he described the financial difficulties that the company faced in 1986:

DW: By early '86, the Mac Plus came out and the Mac market was just incredible. The run rate on ThinkTank 512 was incredible, but the problem was that ThinkTank 512 didn't run on the Mac Plus. The machine was selling in great quantity, but we were out of money, had a head count of over 50, had support problems [with ThinkTank 512] -- we were in desperate shape. While I was out playing in PC land, Peter and Doug had produced all these neat little add-ons to ThinkTank. The question was, can we take all that stuff and put it together and come out with a new product in '86? We put everything the company had on that, financially, in terms of personnel, in terms of our morale. Guy Kawasaki showed us where the market opportunity was with that thing. In June of '86, we came out with More for the Macintosh, and we never had cash problems again.

In 2010, Winer was a little more blunt:

In 1986 my company was in very deep shit. One night I was leaving the office and I knew the next morning I was going to lay off a quarter of the company and cut the salaries of everyone else in half. Even after doing that I still didn't think we could make it. My board had told me to shut the company down and I told them to STFU.

As I locked the front door I stopped and thought, how would it work if we did fail? Would I lock the front door one last time and then walk away? I literally couldn't visualize it. As I drove home I resolved that I would never do that. Somehow we'd get through this crisis and we'd make it work.

Later, when it did work, I realized that moment, while locking the front door that night, was when the company turned around. When we went from being in crisis mode to being a winner, for one very simple reason. I tried to visualize failure, and couldn't do it.

So is Winer right and Microsoft/Apple/Google wrong? Or are Microsoft/Apple/Google right and Winer wrong?

There's one important difference between Living Videotext and, say, Microsoft Bob. Dave Winer was heavily dependent upon the success of Living Videotext. Bill Gates was not heavily dependent upon the success of Microsoft Bob. Now perhaps there were some Bobs (and Lisas) who were dependent upon the success of Microsoft Bob, but I don't know how many got fired when Microsoft Bob locked his door, and how many found new jobs with Microsoft.

Clearly there are two different approaches to new projects - an incubator in which you aim for a certain percentage of projects to succeed, or a single-project focus in which you want (or, using Winer's words, "require") the one project to succeed.

Which is better?