It's hard to confront problems. Whether you need to honestly evaluate the status of a project, understand where someone has difficulty working with you, or just reflect on ways things could be better, it's hard to call out something as bad.

My favorite technique for working around this is to ask "if you had to change one thing, what would you change?" This makes it feel somehow more theoretical: you're under this hypothetical compulsion to call something out, without having to judge whether it's actually bad or just not quite as great. That is important in and of itself, because you want to think in terms of what alternatives and improvements may be available to you, not in absolute terms of good or bad.

So next time you want honest criticism, try asking this question. I'm especially fond of using it in job interviews and other judgment-focused situations to defuse the worry that honesty will offend.

Feel free to comment: if you could change one thing about yourself or your company, what would you change?

One thing I like about building software is that failure is normal. You have to try so many different approaches, and so many of them don't work. Some approaches fail at the idea stage; a few fail after you've spent days or weeks seemingly close to making them work. Each failure is painful.

If you were building a bridge or a putting out a fire, failure would be a total loss: materials wasted, property destroyed. But in making software, failure is actually a form of progress. When you're exploring the boundaries of what's possible, you're often going to set your sights beyond those boundaries. In making software, you're constantly reminded of this. As a result, you either get disparaged and start doing less risky, less creative work—or you learn to treat failure as an experimental result that confirms the value of the endeavor.

People who really care about making software know this. It's spread throughout the culture: good programmers, managers, execs, and even venture capitalists know the value of failure. For all the shortcomings of techie culture, it is this courage that redeems us. And because technology is an ever-increasing part of the world economy, the world is on a cultural path toward valuing failure and away from denigrating it. The effects ripple far beyond technology, making now a better time than ever to be creative.

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I just stood there, staring into the red plastic shopping basket with its mesh of holes showing the very clean linoleum and my navy blue sneakers down there below the two pints of ice cream. I could hear the fluorescent lights hum. I could feel my pulse on the crown of my head. It was 3AM in the supermarket and I was breathing air. I know this seems strange, but I never bought more than one pint of ice cream, ever, not even if I had the money; not even if there was a Buy One, Get One Free sale. Two pints of ice cream? Un-thinkable. Verboten. No. Fucking. Way.

I wanna be smart like Lisa. I wanna live with abandon like her friend Meg.

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Lisa Williams: My father reared me on the saying, "An unchanged mind is like unchanged underwear."

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"Nietzche was the one who did the job for me. At a certain moment in his life, the idea came to him of what he called "the love of your fate." Whatever your fate is, whatever the hell happens, you say, "This is what I need." It may look like a wreck, but go at it as though it were an opportunity, a challenge. If you bring love to that moment — not discouragement — you will find the strength is there. Any disaster you can survive is an improvement in your character, your stature, and your life. What a privilege! This is when the spontaneity of your own nature will have a chance to flow.

Then when looking back at your life, you will see that the moments which seemed to be great failures followed by wreckage were the incidents that shaped the life you have now."

— Joseph Campbell