Chapter 5 - Removing Obstacles

Chapter 5 - Removing Obstacles

The key technique to freedom is to broaden your options. If you have more options, you can pick things you like. You can choose NOT to do things you don’t like.

There are two fundamental ways to increase your options.

  1. Remove the OBSTACLES that are preventing you from picking certain options you already have.
  2. Discover and attract NEW OPPORTUNITIES.

Both of these will give you more effective options.


This is a big one, and it should be part of your long-term strategy towards freedom.

How can you remove an obstacle?

This one primarily requires a problem-solving conversation with yourself.

  • Statement: “I wish I didn’t HAVE to be at the office on Friday.”
  • Question: “Why do you HAVE to be at the office on Friday?”
  • Statement: “Two reasons. We have a weekly team meeting on Friday, and my boss wants me to work from the office.”
  • Question: “Why do you have to be at the weekly team meeting on Friday?”
  • Statement: “Because I’m part of the team. It’s expected.”
  • Question: “Can’t you be part of the meeting without being physically at the office? Join remotely?”
  • Statement: “Jorgen, our Estonia contractor, does that. But I’m not allowed to.”
  • Question: “Why aren’t you allowed to if Jorgen is allowed to remotely join the meeting?”
  • Statement: “Because I don’t live in Estonia.”
  • Question: “That’s not actually a reason for why you can’t attend remotely. Why can’t you attend remotely?”
  • Statement: “Well, I don’t actually know. Maybe I could talk to my boss about it.”
  • Question: “That could solve the first problem. The second problem, why does your boss want you to work from the office?”
  • Statement: “It’s expected of all team members.”
  • Question: “Except Jorgen?”
  • Statement: “Yes, Jorgen is the exception.”
  • Question: “Why is it expected of all team members?”
  • Statement: “Because management is worried that we won’t work hard if we’re not in the office.”
  • Question: “Would YOU work less hard if you didn’t have to be in the office on Friday?”
  • Statement: “Well, no. I’m a hard worker. I would still work hard.”
  • Question: “Then is management’s concern really applicable to YOU?”
  • Statement: “No, it isn’t.”
  • Question: “Does your boss trust you enough to know that it’s a non-issue?”
  • Statement: “Yes, he knows how hard I work.”
  • Question: “Then wouldn’t it be reasonable to ask him if YOU can work remote on Fridays?”
  • Statement: “Yes, I suppose I could do that.”

Often diving deep into the practical reasons for a prevention can lead to a simple path forward that gives you an option you previously didn’t let yourself choose.

This works for simple comfort things like choosing WHERE you work or WHEN you work. It also works for bigger obstacles like:

  • I want to start raising a family, but I don’t have a spouse.
  • I want to land my dream job, but I don’t have a college degree.
  • I want to work on my side project, but I don’t have enough time.
  • etc.

Slow down and think through effective ways to clear away obstacles so that you can choose the things you KNOW YOU WANT.

That’s a good strategy. But there’s another approach, too.

Sometimes there are shortcuts to choosing the things you want.

Removing Obstacles the FAST WAY

Rather than creating deep solutions to complex problems, sometimes there are simple HACKS that can shortcut your path to something you want.

Often you just need a plausible reason to do something that you want to do, which makes it seem reasonable to someone else.

There is a principle that the most effective way to have a thing done is:

Tell, Don’t Ask

To solve a problem this way, create a SITUATION that lets you do the thing you REALLY WANT.

If you don’t want to be at the office on Friday, there are lots of ways you could make it impossible or impractical to be at the office.

For example:

  1. SCHEDULE a doctor’s appointment for Friday on the opposite side of town.
  2. INFORM your team that you’ll be remote on Friday for a doctor’s appointment.

Problem solved.

There are hundreds of FAST PATH answers to obstacles if you are willing to think outside the box and choose from your real range of choices.

The option that you think ISN’T a realistic option actually might be your BEST PATH.

Common Obstacles

What are the most common obstacles that you believe prevent you from choosing the things you want?

  • The thing I want is too big.
  • I need someone’s permission.
  • There’s too little time.
  • I don’t know how to do it
  • People won’t join me.
  • Not enough money to afford it
  • It doesn’t match my personality
  • They won’t approve of it

How can these obstacles be tackled?

Look at BOTH ASPECTS of the equation. Sometimes a small change can make the impossible possible. Sometimes a minor tweak is the key that opens a previously closed door.

  • Can you get a PART of what you want now?
  • What would happen if you DIDN’T have permission?
  • How can you FREE UP some time?
  • What would you need to LEARN to do it?
  • What kind of people WOULD join you?
  • How much money do you ACTUALLY need?
  • Could you change your PERSONALITY a little bit so that it fits you?
  • Does it matter if they approve of it if it’s what you REALLY WANT?

Liberation Exercise:

Set aside 10 minutes to meditate and reflect.

  1. Pick 1 thing that you desire right now that you can’t pick.
  2. Converse with yourself and discover the real reasons that prevent you from having what you desire.
  3. Consider if there are any clever shortcuts to getting what you desire with minimal effort.
  4. Look at those insights and pick 1 action plan for going after what you desire.

In the next week

  1. Take 1 step each day to bring yourself closer to getting what you desire.

Cultivate the HABIT of taking a realistic and practical look at the obstacles between you and what you DESIRE