Chapter 7 - Communicating Your Optionality

Chapter 7 - Communicating Your Optionality

Freedom is only useful if you can use it effectively to live and work the way you wish.

Since our world is a social place, it’s essential to learn how to be free while continuing to happily collaborate with the people in your sphere, especially as you work.

In the previous two chapters, we talked about how you can RECOGNIZE the leverage your already have and how to BROADEN your options. The third key to practical, daily, tangible freedom is to evolve your working relationship with others. The first two keys are internal – they are about changing yourself. The third key is external – it’s about influencing the people and organizations around you.

Working with a truly free person is a much richer and more rewarding relationship than working with a good slave. Truly free people COLLABORATE. They EMPOWER each other. They CHALLENGE each other. They SHARPEN each other.

Your coworkers and your company will benefit more from you acting autonomously. You will have more value to offer. They will give you more trust and respect.

Evolution doesn’t happen overnight. Evolving your relationships will take time.

What are some practical ways to move towards a more freedom-oriented relationship?

The two key elements are:

1) SIGNAL appropriately 2) Use PERSUASION to get what you want

Your boss assigns you a new task when you are already overloaded

Slave Mentality: When assigned a task whether reasonable or unreasonable, they suck it up and find a way to try to do it.

Free Mentality: There is a limit to how many tasks can be performed. We have to prioritize and pick the best ones.

To change this dynamic, the first step is to realize that since you are free, your boss’s assignment is actually just a request. You can accept his request. You can reject his request. You can propose a new option. You can negotiate on the request. All options are open to you.

Realistically, there is an infinite amount of work and a finite amount of your time. You can decide for yourself whether you want to accept this new assignment.

Here are a number of ways you can, as a free person, react to this:


Boss: “I need you to create Report Z by the end of day tomorrow.” You: “I am currently working on X, T, and M, which are all urgent. There’s no way I get that to you tomorrow.”

Team Member Redirection

Boss: “I need you to create Report Z by the end of day tomorrow.” You: “I am currently working on X, T, and M, which are all urgent. I might not be able to get it done tomorrow, but I think Billy has capacity. If this is important to you, you could ask him.”

Present Explicit Trade-Off

Boss: “I need you to create Report Z by the end of day tomorrow.” You: “I am currently working on X, T, and M. I can do the report for you today if we’re willing to delay the completion of X until Monday. George is expecting X tomorrow, but it’s up to you, I can do whichever one of Z or X you want.”

Raise The Price

Boss: “I need you to create Report Z by the end of day tomorrow.” You: “Actually I was hoping to talk to you, I have an appointment to run tomorrow. If I can take off an hour early tomorrow, I can get that report before lunch tomorrow.”

Get Rid Of Unwanted Other Tasks

Boss: “I need you to create Report Z by the end of day tomorrow.” You: “Sounds great! I’ll get that one for you ASAP. If George asks about X, T, or M, tell him that I was working on other important projects for you.”

Create Alternative Solution

Boss: “I need you to create Report Z by the end of day tomorrow.” You: “We are just about finished setting up a new reporting feature on the website. If you can wait until Tuesday, then it will be auto-generated and available on-demand. It will make life EASIER and save countless hours.”

Eliminate Work

Boss: “I need you to create Report Z by the end of day tomorrow.” You: “Is this for Project Rhinoceros? You don’t want Report Z! It’s missing the core pieces of data. Instead, you should ask Tony for a copy of his Report B. It’s got what you really are looking for.”

There are a lot of genuine options! All of these options give you more freedom, elevate your interactions with your boss, give you a chance to offer more value, and build more trust.

There are pros and cons to each approach, and ultimately, you’ll evolve your own interaction style as you start to act freely. But ALL of these options will empower you and make you HAPPIER and more CAPABLE at work.

Each of these responses has a communication element when you signal that you are treating the assignment as a REQUEST and not a DEMAND and that you are CHOOSING some elements of how to solve a real business problem.

The way you respond will also influence what your boss is likely to choose. As you develop your persuasion skills, you will find more and more ways to frame things with the right context to make what you want to do the obvious option for another person. They will FEEL like they are choosing what happens even though YOU orchestrated it.


Another powerful technique is the use of experimentation. If you have something you want to try at work that presently isn’t culturally accepted, propose an experiment.

Create a compelling hypothesis. Present a proposition with your hypothesis, your proposal, and the test criteria.

Suppose you think that it will be more fun to work at a coffee shop all week instead of in the office. So, you go to your boss and say, “Working in the office makes it hard to get any work done. There are too many distractions. There are too many interruptions. It’s hard to focus. I think that our team would be able to get at least 10% more work done if we worked from somewhere else. I have an idea. If you’re okay with it, let’s try a two-week experiment. I’ll work away from the office for these two weeks. Everyone else on the team will work from the office as usual. Then, after two weeks, we can see how many tickets were closed. I’m certain that I will be able to close at least 10% more tickets than in previous periods. After two weeks, we can look at the actual numbers and then discuss, as a team, how we want to work going forward.”

Maybe you don’t actually care about productivity. But a proposal like this lets you do something that you want AND offers an incentive to the business. It’s a win-win. You can also try things even if you aren’t sure whether they will work.

Many of the best and most innovative companies have a culture that embraces experimentation.

Communicate Your Optionality

Your new inner freedom mentality will transform the way you interact with others at work. If you practice these two skills, you will eventually be completely liberated. People will trust you, rely on you, and give you space to work HOW, WHERE, and on WHAT you want to.

The two external keys are:

1) SIGNAL appropriately 2) Use PERSUASION to get what you want

Once you’ve put these into practice long enough, you won’t think of yourself as having a boss even if the company’s organization chart says that you report to someone. You KNOW the best ways to provide value to your company. You are more capable of EMPOWERING the people you report to than they realize.

Trust yourself to take bold steps and influence the people around you. Make your own choices. Realize that everything at work is two-sided. YOU are a key factor in your company.

Liberation Exercise:

Set aside 10 minutes to meditate and reflect.

  1. Write down the people at your company who make you feel restricted.
  2. Write down the specific ways in which you feel held back.
  3. Close your eyes and imagine how you wish you could relate to each of those people.
  4. Pick one of those people and write down the things you wish you could communicate to them.

In the next week

  1. Each time you are about to interact with that person, bring your vision to mind.

Continually CHOOSE interactions that communicate your optionality.