Melinda Gates says screwing up a Microsoft project in 1995 taught her a lesson she'll never forget

Overcome your greatest fears by using Tim Ferriss' fear setting exercise

Today, many recognize businesswoman and philanthropist Melinda Gates for her tireless efforts to make positive change in the world. When she started working at Microsoft in 1987, a year after the company went public, Gates was brought on as a product manager.

Though she would find much success at Microsoft in years following, the flop of a major project in 1995 — considered one of the world's worst inventions by Time Magazine — taught her a lesson she says she will never forget: Failure provides the opportunity to stop what you're doing, rethink and revitalize.

"Anytime that you're dreaming big, you're also going to have spectacular failures," Gates said at this year's Grace Hopper Celebration of Women in Computing.


In the time that Gates eventually worked her way up to general manager of information products at Microsoft, she led a team on a project called Microsoft Bob, as she recalled in a recent LinkedIn article.

According to Gates, only about a third of households had personal computers in the mid-1990s and people were still getting accustomed to them.

Anytime that you're dreaming big, you're also going to have spectacular failures.
Melinda Gates
Co-founder of the Bill & Melinda Gates Foundation

"You know all those things that are instinctual to us today — like looking for a menu of options at the top of the screen? Most people didn't have those instincts yet," Gates said.

To make using the computer easier, Gates and her team built Microsoft Bob, a software program that turned your desktop into a virtual home. For example, to write, you clicked on a pen and paper and to check the date, you clicked the calendar on the wall, she explained.

Unfortunately, Microsoft Bob wasn't the hit Gates anticipated it would be.

"The program needed a more powerful computer than most people had back then and a lot of critics found the visuals too cute," Gates said.

Still, Gates needed to get on stage and present the software demo, noting that "flops like this were part of the process."

The chance to take big risks is exactly what I love about tech.
Melinda Gates
Co-founder of the Bill & Melinda Gates Foundation

"Walking into that public demo was the hardest thing I have ever done," Gates said.

But more importantly, she added, it was a reminder that she chose to put herself in that position.

"The chance to take big risks is exactly what I love about tech," she said.

Until that point Gates said she had made most of her mistakes on expense reports, but as the face of the project, "failing so hard—and so publicly—was a new experience entirely."

When Gates finished her demo, she said she finally understood "why the old joke about failures leading to promotions existed in the first place."

Failures provide "a chance to pause, learn something and choose a new and better direction," she said.

Although Gates left Microsoft to focus on her philanthropic work and family a year later, her former boss at Microsoft and former CEO of the Gates Foundation Patty Stonesifer told Fortune Magazine in 2008 that, "No question, if she had stayed, she would have been on the executive team at Microsoft."

As for Microsoft Bob, the project was discontinued the following year. Part of its "cute" visuals, however, still exists as the notable font Comic Sans.

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