Progress Hacking: How to Create that ‘Winning Feeling’ Every Single Day

I’m a professional procrastinator when it comes to writing. 

It’s the thing I most want to do, yet I seem to never run out of ideas or inventions to distract myself from it. 

Whether it’s making myself excessively busy with work, enrolling in a degree, or coming up with ideas for new ventures I could start – all are forms of procrastination. 

Sophisticated forms, maybe – but procrastination, nonetheless. 

It seems that the more I put it off, the harder it is to get started again. It becomes this big, unapproachable thing that I don’t want to think about.

However, once I have momentum and I’m ‘in the flow’ of doing it every day, it becomes almost effortless. It seems that the hard thing is not the act of writing itself, but rather the act of sitting down to write.

It’s putting myself in the chair that’s the problem. 

This post will explore some of the most effective methods and mindsets I’ve found for overcoming procrastination. If there’s a project you’re wanting to get moving on, but have been putting off, they might be useful for you too.

Why this matters – The Progress Principle

In recent years, researchers have discovered the progress principle.

Simply put, the progress principle suggests that making progress in meaningful work is the single most important thing you can do to increase motivation, boost mood, and improve emotional wellbeing on any given day.

Over a period of four months, researchers studied the diary entries of 238 individuals involved in creative working projects – nearly 12,000 entries in total. Their aim was to discover what inner states of working life and external events correlated with the highest levels of creative output. 

When they compared the best and worst days of the workers, they found that the most common events that triggered ‘best’ days were those in which the person made progress towards a meaningful goal. 

Conversely, the ‘worst’ days (as measured by motivation, mood, and emotions) occurred when the workers experienced setbacks.

The practical takeaway from this study is clear: 

If you want to have a great day (or at least feel like you have), your best strategy is to make progress towards a goal that is meaningful to you.

The rest of this post will explore how you can most effectively do that. 

The Natural Planning Model

‘If something feels impossible, just keep breaking it down into smaller pieces, until it feels possible.’ Mark Manson

In Getting Things Done, David Allen introduces “The Natural Planning Model”. 

This is a simple process that allows you to take any kind of project (big or small) and break it down into smaller, more manageable chunks. 

I discovered Allen’s method in my early 20s, and I’ve used a variation of it to plan, and organise almost every project I’ve been involved in since. 

Here’s a brief overview of how it works: 

1.) Specify the purpose of the project. 

When we are clear on why we need to do a certain task, it provides clarity, focus and flexibility in our approach towards achieving it. 

2.) Identify the guiding principles and values you want to keep in mind as you are completing it. 

For example, if you’re writing a blog post, your guiding principles and values could be: 

  • Simplicity
  • Clarity
  • Creativity
  • Focus
  • Patience
  • Having a deadline and publishing on time
  • Quality


3.) Write a failure statement. 

What would your project look like if it were a complete disaster? 

At this stage, the aim is to write in as much detail as possible about all of the things that could go wrong. This information can then be used in the fifth stage of the planning process – which we’ll come to in a second.

4.) Create a vivid description of the desired outcome. 

What will your project look like when it’s complete? The aim here is to get clear and specific on what “success” looks like.

The more detailed you can be, the better. Your brain is a focusing machine. When you provide it with a clear goal, you create a gap between where you are now (reality) and where you’d like to be (your desired outcome). 

5.) Create a list of next actions that will take you from your current reality to where you’d like to be.

Once the desired outcome has been specified, your brain won’t be able to help but to come up with a list of next actions to fill in the gap you’ve created. It will do this automatically – hence Allen’s name: “The Natural Planning Model”. 

To accelerate this process, it can help to highlight all of the actionable sentences in your failure statement and desired outcome. Each highlighted sentence can then be turned into a concrete next action step. (To illustrate this, you can can see a simple example of how this might work for planning a barbeque with your neighbours here.)

6.) Rank your actions – Find the 20%

“What stands in the way becomes the way.” – Marcus Aurelius

The 80 / 20 principle suggests that in any project, 20% of the inputs will lead to 80% of the outputs.

In other words, 20% of the things that you do will generate 80% of the results. 

Therefore, it’s vital to identify what this 20% is before you begin – so you can rank your actions in order of importance, and begin making meaningful progress towards your desired outcome.

Otherwise, it’s very easy to get bogged down in ‘busy work’ – without actually getting very far.

If you’re not sure what your 20% is, Gary Keller’s “Focusing Question” can really help:

“What’s the ONE thing I can do, such that by doing it, will make everything else EASIER or UNNECESSARY?”

You’re looking for the “lead domino”. 

The task that, if you complete, will make everything else on your list easier or unnecessary

It’s usually the one that you feel the greatest level of discomfort and uncertainty about when you review your list.

Hence Ryan Holiday’s mantra: 

“The Obstacle is the Way.”

Generate Momentum with the Seinfeld Strategy

“Every action we take is a vote for the kind of person we want to become.” ― James Clear

Psychological research has proven that momentum plays a critical role in goal achievement and high performance. 

But how can you best create it? 

And how can you maintain it once you’ve got the ball rolling?

When asked by a young aspiring comedian for advice on how to write consistently, Jerry Seinfeld recommended that he purchase a large calendar and place it prominently on his wall. 

Each day after finishing a writing session, Seinfeld advised the young comedian to mark the day with a large red X. 

Over time, a chain of red X’s starts to develop, and the goal simply becomes to never break the chain

The more X’s that build up, the greater your sense of momentum – and the less likely you are to stop. 

Why might this work? 

In psychology, ‘self-signaling’ refers to one of the processes by which human beings form an identity. 

When we perform a certain action repeatedly, we are essentially telling ourselves: “I’m the sort of person who does ‘X’.” 

In other words, we learn about who we are by observing what we do.

And over time, an identity begins to form.

So, if you write every day for a year, you’ll begin to think of yourself as a writer. And because we have a very basic need for our behaviour to align with our identity (the commitment and consistency bias), this means that if you’re not writing, you won’t feel right about yourself. 

Your habit becomes linked to your emotional state – and this motivates you to keep writing.

Overcome Procrastination with The Pomodoro Method

“Action may not always bring happiness; but there is no happiness without action.” ―  Benjamin Disraeli

Neuroscientists have discovered that the amygdala becomes active during procrastination.

The amygdala is an almond shaped structure which evolved as a survival mechanism to keep us safe from danger in our evolutionary past. It’s function was to scan the environment for threats, and then release hormones which would get us to flee the situation or avoid the attack. 

Unfortunately, this mechanism also becomes active when we encounter a task we find unappealing, difficult or anxiety provoking in modern life.

In other words, your brain can’t tell the difference between a task you’ve been procrastinating on (e.g. beginning an essay), and being attacked by a bear. In both situations, your emotional limbic system is hijacked by the amygdala to get you to avoid the source of threat – and this causes procrastination.

The pomodoro technique, developed by Francesco Cirillo in the 1980s, is one of the most effective ways to overcome this. It involves setting a 25 minute timer for a task, and focusing single-mindedly on it for that period – with no distractions, e.g. checking social media, emails, or texts. 

Then you take a 5 minute break, and begin another 25 minute period, repeating this for four “pomodoros”, at which point you take a more restorative 15-30 minute break. 

I’m speculating, but I believe this might help to overcome procrastination because it may ‘tone down’ the amygdala’s response to the situation.

Now, when your emotional limbic system focuses on the project, it no longer feels like this huge, uncertain blob of difficulty. 

Instead, it knows it only has to work for the next 25 minutes – then it’ll get a break. 

So you can begin making progess towards your goal.

Celebrating small wins

“Desire is a contract you have with yourself to be unhappy until you get the thing that you want.” ―  Naval Ravikant

When you embark on a project, there are two approaches you can take. 

The first is to tell yourself that you’ll be happy when you reach your goal, and postpone your enjoyment of life until then. 

The second is to celebrate each small win on the way towards achieving your goal. Not only does this provide a sense of momentum, and boost happiness, researchers have discovered that celebrating small wins actually makes you more motivated – which in turn, makes you more likely to achieve your ultimate objective.

“If you don’t celebrate the small wins, you’re not going to be very good at celebrating the big things either.” ―  Tim Ferriss

Ferriss’s quote highlights an important truth: 

We are what we repeatedly do.

So, if you gloss over our small wins, and don’t take the time to appreciate them when they occur, then you’ll not be able to celebrate the big wins either. 

Or, as philosopher Alan Watts puts it, there’s no point in planning for the future, if you’re not going to be able to enjoy it when you get there. 

Celebrating small wins is more of an art than a science, and each person will have their own approach for doing it, but here are two ideas to get the ball rolling:

#1 – Keep a ‘jar of awesome’

The idea here, (also recommended by Ferriss) is to write down each ‘mini win’ you experience throughout your day on a tiny piece of paper, fold it up, and then place it in a jar. 

Over time, you’ll begin to build up a collection. 

Then, in the months that follow, anytime you’re feeling in a rut, you can open your “jar of awesome”, and you’ll immediately be brought back to all of those magic moments and little achievements that have been sprinkled throughout your days. 

#2 – Measure the gain. 

Ambitious people have a tendency to measure their self worth against an ideal they’ve envisioned for themselves in the future. 

This creates a gap between where they are now, and where they’d like to be.

As a result, many go through life feeling like they are constantly falling short – no matter how outwardly successful they might appear. 

An alternative approach, recommended by Dan Sullivan, is to measure the gain. 

This involves regularly checking in with yourself (e.g. every 90 days), and asking: 

“Where am I now compared to where I was 6 months ago, 1 year ago, 3 years ago?” 

“What would my former self think about what I have accomplished?”

If you’re giving your best, it’s likely they’d be proud of what you’ve been able to do.

When we regularly measure ‘the gain’, it gives us confidence and a springboard from which to courageously pursue our future goals. Better still, it enables us to feel good as we go about working towards them – rather than constantly experiencing a sense of lack about what we have yet to do.


After more than a year of procrastination, I’m finally back in the habit of writing every day – and I feel a lot better for it. 

Each day that I wake up and write, I feel like I’m making progress towards a goal that is meaningful to me, and this seems to make the rest of the day go a little bit better too. 

What about you?

Is there anything you’ve been procrastinating on, that you’d like to start making progress towards? 

Niall McKeever

Niall McKeever

Writer and Founder of The Weekend University. Passionate about making great ideas more accessible.

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