Based on books, Personal development, Self-awareness

How to Become a Good little Masochist – 3 Ways to Develop Willingness

Most of us assume our levels of willingness are higher than they are in actuality. Truly, much of the time levels are selective at best.

However, willingness is tremendously important to a life well lived. 

Or as Mark Manson puts it:

“Everything sucks, some of the time. If you want to be a professional artist, but you aren’t willing to see your work rejected hundreds, if not thousands, of times, then you’re done before you start. If you want to be a hotshot court lawyer, but can’t stand the eighty-hour workweeks, then I’ve got bad news for you.

Because if you love and want something enough—whatever it is—then you don’t really mind eating the shit sandwich that comes with it. So what’s your favorite flavor of shit sandwich?”

We all know that every single pursuit, no matter how fun or awesome it seems initially, comes with its own side serving of misery. 

When building a life, the question isn't what you want, it's what pain you are willing to sustain Click To Tweet

Opening a cafe or restaurant; becoming a parent; buying a house. Optimism bias leads us to focus excessively on the pleasure aspects of these things, when really our attention should be on the pain; specifically, the type of pain we will need to sustain to get there.

Because the truly important question isn’t what we want. It is what we are willing to do to go after the distant rewards. 

And like any self respecting masochist, ideally we want to enjoy, rather than simply endure the discomfort. When we learn to do that, daily life is sprinkled with intense moments of wellbeing. 

But exactly how does one learn to take pleasure in pain? 

Willingness is cultivable like all other personality traits. We get to decide!

This post, which is based on the advice of Dr Russ Harris in his book the Happiness Trap, is about how to cultivate willingness. 

There are at least three things to appreciate. 

it’s all or nothing 


According to Russ, when it comes to willingness, there aren’t any gray areas. You’re either in or you’re out. From the Happiness Trap

‘There’s no in between. This all-or-nothing property of willingness is expressed in the ancient Eastern saying: You can’t leap a chasm in two jumps.”

So how does this knowledge benefit us when we decide we want to do something hugely endurance-testing like, say, writing a book? 

Being honest with yourself at the outset about your willingness can save you a lot of frustration Click To Tweet

It helps because you can save yourself a lot of wasted time at the outset. When we are being honest with ourselves, we all know when we are half hearted about making a thing happen, as opposed to going all out.

And owning the category we fall into straight away means avoiding the dead time and heartache of a string of broken self promises. 

plan ahead for the dark moments


Say you do decide you are 100% willing (and we will talk about how you decide that in a minute). What practical advice is there for when the going gets tough? 

As with successfully changing habits, having a plan in advance is useful for those times.

Let’s use me as an example. If I have slept poorly on repeated nights, and working on my book is the mental equivalent of nails down a blackboard, I have a back up task. It is book related, this task of mine. And importantly, it gives me a sense of progress. I don’t use it often, but it’s there if I need it. Dr Russ used strategically-positioned encouraging quotes to placate his own resistance during the course of writing his book.

Having a go to workaround for those dark days is a smart exercise in willingness Click To Tweet

You could do this across all the life areas. For example, you can have a plan for those dark relationship days, when the mere sight of your other half makes you want to run from the room screaming; a code word or taking a walk. 

write it all down


Okay, here’s how you know whether you are really willing. 

You write yourself a Willingness and Action plan. Yes it’s nerdy. But it is an excellent exercise in realism. 

Trot out the answers to the following questions:

  1. My goal is to…
  2. The values underlying my goal are…
  3. The thoughts, feelings, sensations and urges I’m willing to have in order to achieve this goal are…
  4. It would be useful to remind myself that…
  5. I can break this goal down into smaller steps, such as…
  6. The smallest, easiest step I can begin with is…
  7. The time, day, and date that I will take that first step is…
Making an action plan is acknowledging upfront the demons you'll encounter Click To Tweet

Here’s an example of how this works:

  1. My goal is to write a book. 
  2. The values underlying my book are realizing years of dedication to personal growth, love, contribution, and creative self expression. 
  3. The thoughts etc that I am willing to have to achieve the goal are boredom, feeling like I’m wasting my time, tiredness, feeling trapped, hopelessness, loneliness, FOMO, uncertainty and insecurity. 
  4. It would be useful to remind myself that I’m not my thoughts or feelings – but it’s okay to feel those things. 
  5. I can break this goal into smaller steps, such as working on my book for half an hour each day.
  6. The smallest, easiest step I can begin with is writing a sentence. 
  7. The time, day and date is right here right now. 

Writing this all down is enormously useful, because it helps you to see what you are going to be up against. You are preparing for the demons you’ll face on the voyage.


overcoming-2127669_640 (2)

So the secret to becoming a good little masochist? It’s willingness.

Willingness is the only way to deal with life’s varied and prolific obstacles. Whenever one comes, you’re going to either say yes or no. If it’s a no, then life shrinks. If you say yes, and keep saying yes, you get to become an unstoppable MOFO instead. 

The secret about willingness is that it snowballs each time you say yes to something hard Click To Tweet

And the awesome thing is, saying yes gets easier. Because each one gives us a little more confidence, and helps to define us to the only person whose opinion is relevant. 


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About Rezzan Hussey

Hi, I'm Rez. This blog is dedicated to the practice and pursuit of self-awareness, which is a pretty massive subject. I hope you'll find something new and useful here. I post twice a week, so come back regularly.