What would you do if you knew it would work?

I had an old boss back in my corporate venture days who anchored a lot of the way I think about startups and life.

There were a handful of newbies, and this boss would hold informal meetings with us in the hall or at lunch or while we waited for a bigger meeting to start. He’d pepper us with questions, but there was one he’d ask more than the rest:

What would you do today if you knew it’d work?

It’s actually a really hard question to answer.

We’d rack our brains for something big and ambitious that would impress him, but we could rarely do it. We’d try something like “we could cold email all the top universities to create relationships with PhDs working on interesting new tech?”, but, he’d shake his head. “Not ambitious enough. Try again.”

We’d try to think bigger, but “thinking big” is deceptively hard. We don’t do it often and it feels unnatural. To help, he’d suggest we think of stuff we’re pretty sure wouldn’t work - this was a way to trick your brain.

When we finally landed on something he deemed ambitious enough, he’d say “ok, great. How can we do it this week?”

We knew the follow-up was coming, but still hit like a burst of cold water. You want me to do that?

But once we got over the initial shock, it became, in his words, “a simple question of logistics.” How can we break this thing down into manageable parts?

I remember a specific time when he pushed a co-worker over and over, repeating “not ambitious enough, try again,” until finally the kid broke and shouted: “I’d propose to my girlfriend!”

My boss smiled and said “that works. Got a ring?” And they started working on logistics.

“Remember, you are always the bottleneck,” he’d say. “You say ‘no’ to things before the world tells you no. Don’t do the world any favors. Force it to tell you ‘no.’”

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So…

What would you do this week if you knew it would work?