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immediate negative effect it would have on the company and what could you do to prevent or minimize it?
2. Put yourself in your boss’s shoes. Based on your work history, would you trust yourself to work outside of the office?
If you wouldn’t, reread Elimination to improve production and consider the hourglass option.
3. Practice environment-free productivity.
Attempt to work for two to three hours in a café for two Saturdays prior to proposing a remote trial. If you exercise in a gym, attempt to exercise for those two weeks at home or otherwise outside of the gym environment. The purpose here is to separate your activities from a single environment and ensure that you have the discipline to work solo.
4. Quantify current productivity.
If you have applied the 80/20 Principle, set the rules of interrupting interruption, and completed related groundwork, your performance should be at an all-time high in quantifiable terms, whether customers served, revenue generated, pages produced, speed of accounts receivable, or otherwise. Document this.
5. Create an opportunity to demonstrate remote work productivity before asking for it as a policy.
This is to test your ability to work outside of an office environment and rack up some proof that you can kick ass without constant supervision.
6. Practice the art of getting past “no” before proposing.
Go to farmers’ markets to negotiate prices, ask for free first-class upgrades, ask for compensation if you encounter poor service in restaurants, and otherwise ask for the world and practice using the following magic questions when people refuse to give it to you.

“What would I need to do to [desired outcome]?”
“Under what circumstances would you [desired outcome]?”
“Have you ever made an exception?”
“I’m sure you’ve made an exception before, haven’t you?”
(If no for either of the last two, ask, “Why not?” If yes, ask, “Why?”)

7. Put your employer on remote training wheels—propose Monday or Friday at home.
Consider doing this, or the following step, during a period when it would be too disruptive to fire you, even if you were marginally less productive while remote.
If your employer refuses, it’s time to get a new boss or become an entrepreneur. The job will never give you the requisite time freedom. If you decide to jump ship, consider letting them make you walk the plank—quitting is often less appealing than tactfully getting fired and using severance or unemployment to take a long vacation.
8. Extend each successful trial period until you reach full-time or your desired level of mobility.
Don’t underestimate how much your company needs you. Perform well and ask for what you want. If you don’t get it over time, leave. It’s too big a world to spend most of life in a cubicle.

► LIFESTYLE DESIGN IN ACTION
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