Fail to Plan, Plan to Fail

January 11, 2025

Having spent over 7,000 hours coaching individuals from all walks of life and speaking to thousands of people seeking change, one thing that continually amazes me is how often people want more from life but lack any form of clarity and direction.

There’s been one consistent challenge that I’ve come across:

The (un)conscious struggle to close the knowing-doing gap.

People come to me with burning ambitions — to actualise their potential, live on their own terms, achieve financial freedom, or build deeper relationships. Their desires are crystal clear, and their motivation is strong. Yet, despite their best intentions, they often remain stuck, unable to make real progress.

Some start, but as soon as motivation wanes, unexpected challenges arise, or they confront parts of their life (or themselves!) they’re not ready to face, they retreat into their old and familiar patterns.

This cycle of desire without direction is one of the biggest hurdles people face daily.

The inconvenient truth is: it’s impossible to execute a plan you don’t have.

Saying, “I want to change [insert desire]” is an idea, not a plan.

Change doesn’t happen by wishing or talking about it.

It happens by defining the steps, committing to them, and doing the work — day in, day out.

This week, I’m giving you my exact prioritisation and planning process — something that, if you learn to master it, can unlock tens, if not hundreds, of thousands of dollars in value. But more than that, it will give you more headspace, time, freedom, and a greater sense of control over your days.

Let that sink in for a moment.

Because this realisation is the key to understanding why so many of us struggle to do what we say we want to do or experience. It’s not just that change is hard (though it often is!) — it’s that we lack the clarity and direction needed to make that change real.

Think about it.

When we try to break free from our deep-rooted patterns — the way we’ve done things for most of our lives — to do something new and move towards something better, we’re up against 30–40 years of conditioning.

We’re fighting against beliefs, habits and behaviours that have become second nature. And if we don’t provide ourselves with radical clarity on what we’re going to do differently and when we’re going to do it, we can pretty much guarantee that we’ll fall back into what we’ve always done — and, by extension, get what we’ve always gotten.

But as this cycle continues, and a clear plan remains elusive, we don’t just fail to make progress — we destroy our self-trust. Each time we break our word to ourselves, we vote against the person we want to become. Over time, this deepens the spiral of inner conflict, frustration, and doubt, making it even harder to believe we can achieve the change we desire and deserve.

These internal struggles make everything more difficult. They push us into a passive and often reactive state rather than a proactive one, spending our days on autopilot, being tossed around by the demands of life, rather than steering it ourselves.

We skip the gym because we didn’t clearly plan how to fit it into our schedule.

We cancel plans with loved ones because work ran late.

We never “find the time” to invest in that side business we swore would take off this year.

This pattern repeats endlessly. And that’s the key difference between desire and direction.

When you desire something, you know what you want.

When you have direction, you know how you’ll get there.

Direction requires clarity. And clarity only comes through intentional effort.

So, this week, I want to offer something different — something I’ve been asked to share for a while. I’m going to walk you through my exact prioritisation and planning process, the weekly ritual I use to ensure my time, energy, and focus are directed towards the tasks, activities, and relationships that matter most.

To ensure I’m not just wishing and talking, but directing my life towards those desires.

For this section, I’ve included screenshots of my notes — complete with examples — along with a description of how this section is designed to work. There’s also a blank template at the bottom of the newsletter if you want to give it a try yourself.

To give you some context, every Sunday before a new month begins, I identify my three priority areas and set clear, specific, and (just!) manageable goals for each — these are my guiding North stars for the month.

I base these goals on three main factors:

  • My big-picture priorities and goals for 2024.
  • What ‘life’ is currently demanding of me.
  • The capacity and resources I have available at that moment.

Finding the balance between these priorities and aligning them with your available capacity is key. It can be tempting to focus only on where you want to go, but true progress sometimes requires fully showing up where you are — dedicating your time, energy, and attention to the key responsibilities in your life, business, or relationships.

I call this capacity-based multi-focus planning.

Which looks like this:

Once I’m clear on my goals for the month, I break them down into weekly tasks and activities using two key criteria:

  1. What is important and urgent.
  2. What is important but not urgent.

This approach is based on the Eisenhower Matrix, which helps me focus on the tasks and activities that have the biggest impact on my progress, growth and success(or happiness).

However, it’s equally important for me also to list (and separate!) the tasks and activities that are important but not urgent. This prevents me from distracting myself with what can be done, instead of focusing on what must be done — what I like to call procrastination 2.0. By identifying the tasks and activities that feels pressing but aren’t critical, I create a sense of clarity, order, and ease.

Most importantly, I ensure that the tasks in the ‘important and urgent’ box never exceed 70% of my total capacity. Instead of stretching myself too thin, I leave room to deal with unexpected twists and turns — whether it’s urgent work demands, personal emergencies, or sudden opportunities.

This way, I stay adaptable, resilient, and ready for whatever comes my way. And if my capacity is lower — say at 40% because of fatigue or competing priorities in another domain — I plan at 70% of that reduced capacity, which is just 28%. This ensures things remain manageable and gives me space to recover and restore my capacity to 80%, and eventually 100%.

Again, clarifying your most important tasks and activities and learning to work within your capacity not only provides direction and improves productivity, but allows you to keep giving your best, week in and week out.

Which looks like this:

From here, I now have a clear view of the tasks and activities I need to complete in a given week to ensure that I can continue moving in the right direction. But something I want to make clear is that knowing what you are going to do is only half the battle.

To truly take the driver’s seat, I also clarify what I won’t do or engage in.

Therefore I create a third list: my ‘not to-do list.’ This list serves as a proactive safeguard for my time, energy, and focus by identifying the tasks, activities, or meetings I will say no to.

To build this list, I focus on three key criteria:

  • What tasks or activities aren’t aligned with my highest priorities.
  • What previously agreed-upon commitments need to be cancelled or postponed.
  • What habits or behaviours tend to distract me from my goals.

By identifying these distractions, I can take proactive steps to avoid them. Whether it’s mindless scrolling on social media, unnecessary meetings, or even overcommitting to social obligations, recognising these habits helps me reclaim my focus.

The biggest benefit of a ‘not to-do list’ is the freedom it provides. By eliminating distractions and unnecessary commitments, you protect your capacity and reserve your best energy for pursuits and people that matter most.

Which looks like this:

The following two steps of my planning process are more personal and can vary from person to person based on their priorities, goals, and interests. Personally, I focus these steps on my vitality and relationships.

As you may know, I consider vitality to be the keel of my ship; it provides the necessary balance to navigate life’s ups and downs, and counterbalance the force of the wind. It allows me to approach my personal and professional priorities with energy, resilience, and optimism while countering the demands of my ultra-running career.

Every week, I clearly outline the routines, practices, and activities that support my physical, menta,l and emotional well-being. This includes foundational elements like maintaining a consistent sleep schedule, staying hydrated, and following my training schedule, as well as additional activities (or corrections!), such as limiting screen time or sugar intake.

By plotting these activities into my weekly schedule, I create a roadmap and choose to make them an integral part of my week.

Which looks like this:

And in a similar way, I do the same with my relationships with those who mean the most to me. Every week, I take a moment to identify who I wish to spend time with, who I want to send a message of encouragement, support, or gratitude to, and — most importantly :) — what I want to do with and how I can surprise my partner.

This allows me to put the most important people at the forefront of my life. It helps me ensure that I make time for them, no matter how busy I am — whether it’s planning a special date, sending a heartfelt message to a close friend, or taking a moment to call my parents, these small, intentional acts keep me connected to the people who make my life worth living.

Which looks like this:

From here, now that you know what you need to do, the next step is to clarify when to do it. It’s crucial to take this level of clarity and plot your tasks into your day-to-day planning and eventually, your calendar.

This is where intention turns into plans. Knowing your priorities is essential, but without scheduling when you’ll work on them, they can easily slip through the cracks.

You’re no longer just hoping to find time — you’re intentionally making time.

So, as you start your week, take the clarity you’ve gained around what matters most, and lock in when you’ll focus on it. And that’s it, you’ll find a blank version at the very bottom of this email for you to use if you’d like.

I hope you found this useful.

PS. Here’s the blank version of my planner below:

MONTHLY GOALS | MONTH …

PRIORITY AREA 1 — …

PRIORITY AREA 2 — …

PRIORITY AREA 3 — …

WEEKLY PRIORITIES & TO DO’S | WEEK …

TO DO THIS WEEK | IMPORTANT & URGENT:

TO DO THIS WEEK | IMPORTANT & NOT URGENT:

NOT TO DO THIS WEEK:

TO SUPPORT MY VITALITY | WEEK …

ROUTINE:

  • ..
  • ..

ADDITIONAL:

RUNNING:

TO NURTURE MY RELATIONSHIPS | WEEK …

WHO DO I WANT TO SEE THIS WEEK:

WHO DO I WANT TO REACH OUT TO (OVERSEAS):

TO DO WITH / SURPRISE MY PARTNER:

DAILY TO DO’s

TO DO MONDAY:

TO DO TUESDAY:

TO DO WEDNESDAY:

TO DO THURSDAY:

TO DO FRIDAY:

TO DO SATURDAY:

TO DO SUNDAY:

  • Prioritise & plan my week.

Enjoy the article?

Consider joining the community of high-impact individuals getting valuable, actionable self-led insights delivered directly to their inboxes through my bi-weekly newsletter, The Unbound Leader.

JOIN THE COMMUNITY

Latest Articles

Clarity

to know what to do.

Strength

to give what it takes.

Freedom

to live how you want.

Join 10K readers of The Unbound Leader for actionable ideas and practical tool(s) to help you own your potential, work and life. And get immediate access to one of my highly requested guides.

I will never spam you or sell your info. Ever.

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

© 2024 Jord Cuiper.