The 4-Hour Workweek: Escape 9–5, Live Anywhere, and Join the New Rich - Expanded and Updated

First, he speaks with his boss on July 12 about additional training that might be available to employees. He proposes having the company pay for a four-week industrial design class to help him better interface with clients, being sure to mention the benefit to the boss and business (i.e., he’ll decrease intradepartmental back-and-forth and increase both client results and billable time). Sherwood wants the company to invest as much as possible in him so that the loss is greater if he quits.

Step 2: Prove Increased Output Offsite

Second, he calls in sick the next Tuesday and Wednesday, July 18 and 19, to showcase his remote working productivity.⁶⁰ He decides to call in sick between Tuesday and Thursday for two reasons: It looks less like a lie for a three-day weekend and it also enables him to see how well he functions in social isolation without the imminent reprieve of the weekend. He ensures that he doubles his work output on both days, leaves an e-mail trail of some sort for his boss to notice, and keeps quantifiable records of what he accomplished for reference during later negotiations. Since he uses expensive CAD software that is only licensed on his office desktop, Sherwood installs a free trial of GoToMyPC remote access software so that he can pilot his office computer from home.

Step 3: Prepare the Quantifiable Business Benefit

Third, Sherwood creates a bullet-point list of how much more he achieved outside the office with explanations. He realizes that he needs to present remote working as a good business decision and not a personal perk. The quantifiable end result was three more designs per day than his usual average and three total hours of additional billable client time. For explanations, he identifies removal of commute and fewer distractions from office noise.

Step 4: Propose a Revocable Trial Period

Fourth, fresh off completing the comfort challenges from previous chapters, Sherwood confidently proposes an innocent one-day-per-week remote work trial period for two weeks. He plans a script in advance but does not make it a PowerPoint presentation or otherwise give it the appearance of something serious or irreversible.⁶¹

Sherwood knocks on his boss’s office door around 3 P.M. on a relatively relaxed Thursday, July 27, the week after his absence, and his script looks like the following. Stock phrases are underlined and footnotes explain negotiating points.

Sherwood: Hi, Bill. Do you have a quick second?

Bill: Sure. What’s up?

Sherwood: I just wanted to bounce an idea off of you that’s been on my mind. Two minutes should be plenty.

Bill: OK. Shoot.

Sherwood: Last week, as you know, I was sick. Long story short, I decided to work at home despite feeling terrible. So here’s the funny part. I thought I would get nothing done, but ended up finishing three more designs than usual on both days. Plus, I put in three more billable hours than usual without the commute, office noise, distractions, etc. OK, so here’s where I’m going. Just as a trial, I’d like to propose working from home Mondays and Tuesdays for just two weeks. You can veto it whenever you want, and I’ll come in if we need to do meetings, but I’d like to try it for just two weeks and review the results. I’m 100% confident that I’ll get twice as much done. Does that seem reasonable?

Bill: Hmm … What if we need to share client designs?

Sherwood: There’s a program called GoToMyPC that I used to access the office computer when I was sick. I can view everything remotely, and I’ll have my cell phone on me 24/7. Sooooo … What do you think? Test it out starting next Monday and see how much more I get done?⁶²

Bill: Ummm … OK, fine. But it’s just a test. I have a meeting in five and have to run, but let’s talk soon.

Sherwood: Great. Thanks for the time. I’ll keep you posted on it all. I’m sure you’ll be pleasantly surprised.

  Sherwood didn’t expect to get two days per week approved. He asked for two so that, in the case his boss refused, he could ask for just one as a fallback position (bracketing). Why didn’t Sherwood go for five days remote per week? Two reasons. First, it’s a lot for management to accept off the bat. We need to ask for an inch and turn it into a foot without setting off panic alarms. Second, it is a good idea to hone your remote-working abilities— rehearse a bit—before shooting for the big time, as it decreases the likelihood of crises and screwups that will get remote rights revoked.

Step 5: Expand Remote Time

Sherwood ensures that his days outside of the office are his most productive to date, even minimally dropping in-office production to heighten the contrast. He sets a meeting to discuss the results with his boss on August 15 and prepares a bullet-point page detailing increased results and items completed compared to in-office time. He suggests upping the ante to four days per week remote for a two-week trial, fully prepared to concede to three days if need be.

Sherwood: It really turned out even better than I expected. If you look at the numbers, it makes a lot of business sense, and I’m enjoying work a lot more now. So, here we are. I’d like to suggest, if you think it makes sense, that I try four days a week for another two-week trial. I was thinking that coming in Friday⁶³would make sense to prepare for the coming week, but we could do whichever day you prefer.

Bill: Sherwood, I’m really not sure we can do that.

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