Ask Yourself HOW a Thousand Times6 min read

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When we know exactly what to do and how to do it, it is much easier to take action. We are naturally more present, confident, and focused.

When we have a goal but not the clarity on how to achieve it, we don’t know what to do next. We default to not taking action, to just coasting. If we do take action, it is haphazard and ineffective—unlikely to take us very far.

You may want to lose weight, earn more, master the guitar, deepen your meditation, overcome anxiety, start a business, or achieve enlightenment—but until you have a clear and specific plan, all you have is a wish. You want something, but there is no clear way forward, no next step. Reality will then suffocate your aspirations, and you’ll find yourself lost in the thick of thin things, to use Covey’s expression.

Planning is the first step in manifesting your aspirations into your reality, and proof that you are not only a dreamer, but a committed creator. As one of the disciplines of the Higher Mind System, planning includes several different practices. In this article, we will focus on planning your path to your goals.

Planning Your Path

To plan your journey you need to get your aspiration and break it down into milestones or phases. This will give you the skeleton of a path—it shows you how you will achieve what you want to achieve. From here you can then figure out the specific actions you need to take, and habits you need to build, to make progress.

For example, suppose you have an aspiration to become a successful speaker. You are pretty driven, feel passionate about your topic, and believe that you have found your career aspiration. But you are not yet taking steps to make it concrete, and a sense of frustration begins to grow inside of you.

This is because you have not laid out the path, so it’s not clear what you should do next. You don’t have a plan, and so you don’t take action.

Now suppose that after some study and brainstorming, you break down your aspirations into the following milestones and goals.

  • Milestone 1: Foundation.

Goal #1: Take my public speaking skills from a 3/10 to a 7/10 within the next 6 months. Join Toastmasters and go through program XYZ for this purpose.

Goal #2: Read the 10 best books on my subject matter, highlighting powerful ideas and practice delivering them out loud with eloquence and spirit.

Goal #3: Write 10 speeches on my favorite topics, developing my own original ideas, and get expert feedback on the drafts.

  • Milestone 2: Proficiency.

Goal #1: Deliver 50 speeches within one year, even if all unpaid.

Goal #2: Get 10 hours of professional coaching to review and perfect my skills.

  • Milestone 3: Marketing.

Goal #1: Setup a website, podcast, and newsletter.

Goal #2: Do 12 outreaches per week to organizations that are in my target market.

Now you have a plan. It’s based on your incomplete knowledge of the topic and the path ahead, for sure, but it is good enough for a starting point. It tells you how you will move forward. Now you can simply focus on the first goal of the first milestone, and forget about the rest. Now you have a focal point for your energy and for your desire.

To implement this, book one or two hours in your calendar to brainstorm the path ahead for you, and write down the plan in relation to one of your aspirations. It doesn’t matter how basic and rudimentary this plan is. You can improve a bad plan, but you cannot make real progress without a plan.

Planning Your Actions

The next level of planning is to then break down your first goal into specific action steps and habits to be built—for example:

  • Action steps:

• Join a Toastmasters group near my home

• Find a great public speaking program/course

  • Habit: Spend an hour every day working on my speaking skills, following the exercises I’m learning

Whenever you are stuck about what to do next, just start from what you know, and ask yourself “How?” For example, if what you know you need to do is to “Join a Toastmasters group near my home”, you can ask yourself “How to do that?”

Then you begin to see the sub-steps of that task: going to the Toastmasters website, finding their directory of meetings, choosing one group in the list, booking the first meeting, adding to your calendar, then attending.

“How” is a powerful question that directs your mind to look for the action steps. Without it, you have only a vague mental image of what you need to do, and it is much easier to procrastinate on it, feel confused, or lose motivation.

The Power of HOW

You can use the power of how to make any goal or action step more specific. Keep asking “How am I going to do this?” until you have covered all the bases.

Building on the example above, your thinking could go like this.

  • I want to take my public speaking skills from a 3/10 to a 7/10 within the next 6 months.

• “Okay, but how will you do that?”

  • I will practice an hour of public speaking exercises every morning.

• “How will you make time for it and remember to do it?”

  • I will wake up half an hour earlier and not waste time on my phone. That should clear an hour of time every morning.

• “How will you wake up half an hour earlier and not waste time on your phone?”

  • I will go to bed half an hour earlier, put my phone in airplane mode before sleep, and not go online until I have finished my speaking exercises.

• “How will you go to bed half an hour earlier?”

  • I will set up an alarm on my phone.

• “How will you make sure that you follow the alarm when it rings?”

  • I will make a strong determination, right now, that when the alarm to go to bed rings, I will finish up my day and be in bed in 20 minutes, no matter what. I will remember that if I don’t do this, I won’t wake up early and won’t have time for working on my aspiration.

• (Nothing further to ask.)

Can you see how this brought you from a simple intention to follow a goal to a clear plan of how it will be followed? You could continue asking “how” about all the variables of your path, until everything is laid out with utmost specificity.

All of this gives a clear map for your brain. This way, the way you spend your time and energy is much more likely to be conducive to your goals, than if you just had a simple intention of “I’ll practice speaking every morning”. Why? Because you have mapped everything that can go wrong, and decided how you will make sure that things go the way you want them to go.

Imagine that you want to travel from New York to Austin, Texas. How likely are you to get to your destination if your only instruction is “Travel southwest”? That’s not enough, you’d want a step-by-step navigation and some clear road signs.

The road to our aspirations doesn’t naturally come with a step-by-step navigation system—so you will need to create your own. You do that by asking yourself HOW a thousand times until there is no more doubt or confusion left in your mind about what to do next.

Parting Thoughts

Much of my work in coaching is helping clients gain clarity and focus, so that they can take action. This often happens through asking simple how-based questions around their blindspots.

In the example above, most people would be satisfied with the thought “I will practice speaking for an hour every morning”. Yet that is rarely enough. There are a thousand variables that need to be illuminated and decided on. As the saying goes, the devil is in the details—get him out of there, by shinning the light of your awareness everywhere.

Once you have investigated the whole field of possibilities and affirmed your aspiration in all possible ways, then you’ve got it all covered. Then your plan is complete. You will need less willpower to stay on track. The road forward will be smoother, and have fewer surprises.

When people are not taking action toward their goals, it’s often because of lack of clarity. The first part of that clarity comes in the aspire step, as you ask yourself WHY a thousand times. The second part of that clarity—much neglected—comes in the plan step, by asking yourself HOW a thousand times.

What goal or area of your life do you need to ask HOW more thoroughly?

Do you know someone who needs a clearer plan toward their goals? Send them this article!


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