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Sherwood: What’s your main concern?64

Bill: It seems like you’re on your way out. I mean, are you going to quit on us? Second, what if everyone wants to do the same?

Sherwood: Fair enough. Good points.65 First, to be honest, I was close to quitting before, with all the interruptions and commute and whatnot, but I’m actually feeling great now with the change in routine.66 I’m doing more and feel relaxed for a change. Second, no one should be allowed to work remotely unless they can show increased productivity, and I’m the perfect experiment. If they can show it, however, why not let them do it on a trial basis? It lowers costs for the office, increases productivity, and makes employees happier. So, what do you say? Can I test it out for two weeks and come in Fridays to take care of the office stuff? I’ll still document everything, and you, of course, have the right to change your mind at any point.

Bill: Man, you are an insistent one. OK, we’ll give it a shot, but don’t go blabbing about it.

Sherwood: Of course. Thanks, Bill. I appreciate the trust. Talk to you soon.

Sherwood continues to be productive at home and maintains his lower in-office performance. He reviews the results with his boss after two weeks and continues with four remote days per week for an additional two weeks until Tuesday, September 19, when he requests a full-time remote trial of two weeks while he is visiting relatives out of state.67 Sherwood’s team is in the middle of a project that requires his expertise, and he is prepared to quit if his boss refuses. He realizes that, just as you want to negotiate ad pricing close to deadlines, getting what you want often depends more on when you ask for it than how you ask for it. Though he would prefer not to quit, his income from shirts is more than enough to fund his dream-lines of Oktoberfest and beyond.

His boss acquiesces and Sherwood doesn’t have to use his threat of quitting. He goes home that evening and buys a $524 round-trip ticket, less than one week’s shirt sales, to Munich for Oktoberfest.

Now he can implement all the time-savers possible and hack out the inessentials. Somewhere between drinking wheat beer and dancing in lederhosen, Sherwood will get his work done in fine form, leaving his company better off than prior to 80/20 and leaving himself all the time in the world.

But hold on a second ... What if your boss still refuses? Hmm ... Then they force your hand. If upper management won’t see the light, you’ll just have to use the next chapter to fire their asses.

An Alternative: The Hourglass Approach

It can be effective to take a longer period of absence up front in what some NR have termed the “hourglass” approach, so named because you use a long proof-of-concept up front to get a short remote agreement and then negotiate back up to full-time out of the office. Here’s what it looks like.

1. Use a preplanned project or emergency (family issue, personal issue, relocation, home repairs, whatever) that requires you to take one or two weeks out of the office.

2. Say that you recognize you can’t just stop working and that you would prefer to work instead of taking vacation days.

3. Propose how you can work remotely and offer, if necessary, to take a pay cut for that period (and that period only) if performance isn’t up to par upon returning.

4. Allow the boss to collaborate on how to do it so that he or she is invested in the process.

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