Singing:

I used to take voice lessons from Warren Senders.

For each lesson, I'd bring in one song I was trying to improve.

First, I'd sing it for him as-is.

Then he'd say, “OK - now do it up an octave.”

“Uh... up an octave?”

“Yes! Go! 1.. 2.. 3.. 4..”

I'd sing the whole song again, in screeching squeaking falsetto, sounding like an undead cartoon mouse. But by the second half of the song, it was almost charming.

Then he'd say, “OK - now do it down an octave.”

“Down an octave? But I don't think I can!”

“Let's try! Go! 1.. 2.. 3.. 4..”

Have you ever tried to sing lower than your voice really goes? Mine sounded like a garbage disposal or lawn mower, but he kept saying, “Pitch!” - and the point was the control of the vocal chords down in that chaotic range and the intense focus it takes to hear the pitch in a creak.

Then he'd say, “OK. Back to normal pitch, but double-time! 1!2!3!4!”

I'd sing the whole song twice as fast, which brought out different rhythmic phrasing and articulation challenges.

Then he'd say, “OK. Relax. Now do it half-speed. 1 . . . 2 . . . 3 . . . 4 . . .”

Singing a song half-speed really brings a microscope to its details!

Now sing it like Bob Dylan. Go! Now Björk. Go! Tom Waits! Go!

Now sing it like I just woke you up at 4am. Now like it's a chant at a football game!

We'd end with me singing the song at its original speed in my normal voice, like I did the very first time. But of course it sounded different - like seeing your home town after being away for years.

If you care about a song, it's worth an hour of experimentation. Realizing the initial choices you made are just one of many brings all kinds of weathered wisdom and perspective to your song.

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Business:

I'm taking an entrepreneurship class now. I've never studied business before.

We analyzed a business plan for a mail-order pantyhose company.

After reading the whole thing, I felt like my old voice teacher:

• “OK - make a plan that only requires $1000. Go!”
• “Now make a plan for 10-times as many customers. Go!”
• “Now do it without a website. Go!”
• “Now make all your initial assumptions wrong, and have it work anyway. Go!”
• “Now show how you would franchise it. Go!”

You can't pretend there's only one way to do it! No business goes as planned, so make 10 radically different plans.

Realizing the initial choices you made are just one of many brings all kinds of weathered wisdom and insight into your business.

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Life:

• Now you're living in New York City, obsessed with success. Go!
• Now you're a free spirit, backpacking around Thailand. Go!
• Now you're a confident extrovert and everyone loves you. Go!
• Now you're married and your kids are your life. Go!
• Now you spend a few years in relative seclusion, reading and walking. Go!

... bringing all kinds of weathered wisdom and perspective into your life.