It’s What You Do After Planning That Matters

If you executed all the plans you made in the last 5 years, what would your life look like?

Olabanji Stephen
15 min readMar 27, 2024
Image by Olabanji

One time, I sat and asked myself — what if I came through with all the plans I've made in the last 5 years?

Year in, year out…

I mean, what would my life look like today, if I kept all the promises I made to myself?

“Damn!” I thought.

Didn’t feel good.

That’s what this letter is about. I don’t want you to feel that way.

Planning can be delightful.

One of the reasons I like to plan is that my audacious goals start to look feasible. From a day’s to-do list to a 2-year goal.

Writing down what I will do now — and next — and next — and what should happen now and what should happen next makes me feel closer to achieving my goals, even without taking any action aside from jotting down my thoughts.

Growth plans, money plans, travel plans, business plans, fitness plans… all plans!

You know?

Books you planned to read, money you planned to make, the blog, YouTube channel, album, or side business you planned to start; or even how you’ll become president in 8 years. What if you came through? Picture it for a moment.

One of humanity’s greatest gifts is the ability to dream and charge towards a goal. Research shows that many people who say they have miserable lives actually do because they are not charging towards a meaningful goal or adventure.

The future is largely unknowable but not having a plan is like going somewhere you don’t know without a map. That’s a double tragedy.

And having a plan without coming through on it is like knowing where you’re going with the map in your hands and deciding to go nowhere or elsewhere.

I hate to be hard on you (if I seem to be) but there are hardly any fences in life, and being stagnant is not a thing.
If you’re not charging towards a goal, you’re not stagnant — you’re actually moving backward because everything around you is moving — the world, time, people.

One of the things I dreaded about not coming through with my plans was that I wasn’t keeping my promise to myself (even though I kept my promise to other people).

In this letter,

  1. I’ll explain the 3 reasons for the gap between planning and doing and how to close the gap.
  2. I’ll show you how to chart a course from where you are to where you want to be. I mean, REALLY make plans.
  3. And how to do what you plan.


Image by Olabanji


Why is it there?

The University of Scranton says that 92% of people who set New Year’s goals never actually achieve them.

On a smaller scale, there are 41% of to-do list items that never get done, and only 15% of “dones” started as “to-do” according to iDoneThis.

We don’t do much of what we plan, and we do a lot of things we don’t intend.

I’ll show you three reasons why this happens.

Projection bias (the first reason)

We tend to overestimate how similar our future selves are to our current selves.

Let’s say you are hungry and go to the grocery store to buy food. You may load up your cart with snacks and pastries along with the real food you plan to eat.

Upon getting home, you start to snack on the doughnut while your food cooks. When your food is finished, you realize that you’re no longer hungry. “But I was starving!” you ask yourself.
Now you have all this junk food you don’t even want anymore.

This is called projection bias.

In this example, you see that we predict how hungry we’ll be in the future from how hungry we are now, causing us to make decisions that do not consider our future selves.
Now, that’s a big deal because planning is largely about the future.

An even more contextual example:
You set a goal to start a side hustle and make your first million in one year. You’re pumped. Motivated. Excited. Rested.
So, what do you do next? You chart a course from where you are to your million — you plan.

In your plan, you have things like — reaching out to 100 leads every day, following up on leads twice a week, reading a chapter of any business book every day, creating (and posting) content thrice a week, reinvesting 100% of revenue for the first 6 months and on and on.

Remember you have a job already, a family, financial obligations, and things you might not be able to (or want to) run away from.

Is it possible to achieve your goal? Yes.
Is your plan feasible? Probably not.

You projected how pumped, excited, and ambitious you are feeling now on how you will feel in one week when you get back from work at 6 pm, likely tired, less pumped, and motivated.

And you have to read, create content, reach out to leads, follow up on some, work on financials, and so on, so you black out.

It’s why New Year’s (or any) resolutions hardly work.
The person making the resolution did not consider the person who would fulfill the resolution — You now. You later.

Don’t underestimate how much you will change, because you will… change.

To understand the gap, you must understand the timeline

When you plan, there are three people in the process

These three people have different priorities and are most likely in different situations

The current you — the planner. Maker of promises
This person dreams, sees long term, has a goal, gets excited about making plans, gets ideas… usually less realistic.

The keeper you — the doer — the leader
This person carries out the plan, makes daily decisions, engages in daily activities, might have a job, deals with daily challenges, and meets unplanned situations. Faces Reality

The future you — the benefiter —
This person reaps the benefits or failure that comes from executing, poorly executing, or not executing the plan

You have to consider all three people when making plans

Image by Olabanji

The Planner

This version of you dreams and is ambitious. You’re excited about the idea of a future self that has something or everything your current self wants.

You promise yourself a dream and assign tasks to yourself to achieve it. “Why the hell won’t this work if things go as planned?” You think to yourself.

The Keeper

This version of you is in charge of getting the work done. This is the you that keeps the promise your other self makes.
This is you in the driver’s seat on the journey you have mapped out.
It’s the you that faces the blank page, starts the project, hits the street to get clients, sends 100 emails a day, says nice things to annoying clients, saves at the expense of your wants, and maintains a diet at the family dinner or on a date to stay fit.

It’s the you who carries out the tasks assigned by the planner.
The you that faces the reality of executing your plan.

This is you as a leader, leading yourself.

Planning is simply ‘the dreaming you’ assigning tasks to ‘the keeper you.’

The Benefiter

This is the you that benefits from the results of the work the planner and keeper did. Good, average, or bad.

This is the you that is bursting with pride, glad and grateful for how well you led yourself, even though it didn’t go exactly as planned. You did what you knew best to be your part.
Or the you in pain, regret, contempt, and less confidence from not getting the job done.

I’ll tie this up. Two more reasons. Stay with me.

You don’t want it (the second reason)

Deep down, you don’t want it.
You think you want it but you really don’t.

Charles Horton Cooley has a profound quote:

“I am not who you think I am; I am not who I think I am; I am who I think you think I am”

Our beliefs, thoughts, and ideas are how we make sense of the world. It’s impossible to exist without them — The Mind Programs.

Dan Koe once asked, “Who wrote the code in your head?” And that’s a great question!

Our idea of who we are is completely mental. It’s why beauty is in the eyes of the beholder!
It’s also why I can trust this letter to make you a better person.
I’m writing codes in your mind (and thanks for letting me!) but are you also letting the wrong people and ideas in — friends, family, colleagues…the internet?

The internet makes it possible and seamless for an unbelievable amount of ideas to penetrate your thoughts and shape who you are without your permission on a daily basis.

Success, happiness, work, marriage, etc. are painted to you in different ways. Now you want to be like this person and this person and this person, and you want this and that and that and that.
Not like you shouldn’t, but over-scrolling makes it increasingly harder to listen to yourself and access your source code — who you really are and what you want.

Don’t get me wrong, it’s not all terrible and stuff.
I’ve learned from the internet and I get motivation from there but I’m also quick to hit unfollow and unsubscribe to any idea, advice, or content without context.

Content minus Context = Disaster code.

It’s why books and long-form content like newsletters, podcasts, and lectures still win if you want to write good mind programs.

Otherwise, you may be acting on marriage advice from a 30-second clip of someone who failed in it and is looking for solace by pursuing activities that bring them the attention they were getting from their partner in likes and comments and you wouldn’t even know.
I don’t mean to be savage, but you get it, right?

Why are you doing what you’re doing? Most people don’t even know.

That’s a great way to be mindful — ask ‘why?’

Why am I doing this? Why do I think this? Why do I want this?

You will start to filter out the noise and access your source codes — what you really want and what you believe to be true.

Writing also helps so don’t stop at thinking.
Grab a pen and a sheet of paper. Ask yourself questions and answer them in there.

When you can’t answer a question, you’ve reached a point of needed clarity. That’s a critical point. It’s how you access source codes.

Look for a book, article, or video that’ll give you a better understanding of that part of yourself.

It’s how you gain clarity and become formidable!

Deep down, you might not want what you’re pursuing and that diminishes the sense of mission you should have.

A lack of a sense of mission will affect your pursuit negatively.

The journey will be less fulfilling. It’s harder altogether.

Defensive failure (the third reason)

I’m not talking about procrastination here.
Procrastination is reviewing a plan you’ve not implemented for the 10th time.

I’m saying…
You believe that at the core of success is talent or something you don’t have and that some people are wired to do it better than you. And your failure is in fact a sign that this is not for you.
This is defensive failure.

Coined by Amanda Crowell (Cognitive Psychologist), Defensive Failure is what happens when we want to achieve something, and we constantly think about it, but we don’t do it.

We believe we will fail if we try. And our brains — our identities, prefer the smaller failure of not trying.

Of course, you’ll do it badly on your first attempt and perhaps many attempts after that!

The fact that it’s difficult does not mean it’s not for you.

Now let’s tie this up and turn you into a badass achiever with these 5steps

  • Understand yourself
  • Understand the world around you
  • Eliminate projection bias
  • Make plans like this (I’ll show you)
  • Seek support and accountability


Understand yourself

You have to be mindful and self-aware to understand yourself.

Mindfulness is paying attention to what you’re paying attention to

- Dr. Ellen Langer

Effects (your outcomes) have causes. To control your outcomes, you must understand the part of yourself that is producing that outcome. This is why you have to be mindful and self-aware.

Why did I do that?
Why did I say that?
Why do I want that?
Why do I like this?
Why am I always late to work?
Why did this just happen?
Why is this stressing me?
Or why am I calm in this situation?
Why am I attracted to these kinds of people?
Or why do they find me attractive?

Self-awareness is the ability to look inward, think, and understand your own feelings, emotions, stressors, and personality. These understandings play a critical role in influencing our judgments, decisions, and interactions.

The more mindful you are, the more self-aware you can become.

The drill is — to pay attention, ask ‘why’

Pay attention to your thoughts, actions, and reactions

Ask yourself ‘why’ and don’t be afraid to go deeper

Self-awareness is key to understanding yourself. Our goal is to close the gap but we can’t fix what we are not aware of.

You can learn from others but you don’t have to do things like them.
What you do has to be what is best suited for you. There are no two people exactly like you. No one has your parents, childhood, influences growing up, memories, and experiences.

You are different. And you can change (in fact, you should — it’s called growth) but first, understand yourself.

Walking helps me decompress and channel more creative energy. Horse riding too, so I live close to a stable.

Running might work better for you. Or hitting X on a PS5 pad as you shoot the enemies in Call of Duty. Or a cup of tea and sitting in silence. You’ve gotta know you. And be confident in ‘you’.

Meditation and journaling will help you as well. Don’t just think.
Write about yourself without judgment (we are the harshest judges of ourselves).

What you want is a progressive understanding of yourself.
Who you are. What makes you tick? Your actual beliefs and values

Understanding yourself will help you plan more honestly.

You know how much you can really do.
What you really want.
You’d be able to capitalize on your strengths.
You’ll also learn more constructively because you can tell which part of you is working against your goals.

I’ve met people who make plans as though someone else will be executing it!

Bonus: Take a personality test here

Understand the world around you

Be honest about your situation.

Allocate the time, energy, and resources that you can honestly afford when you plan.

If you go back to the plans you’ve made in the past (and you should), the things you didn’t achieve are likely the ones you worked the least on and the reason is likely because you allocated wrongly.

Your situation will not stop you if you properly factor it in, even if you consider your situation terrible.

This doesn’t mean you should not stretch yourself but be progressive about it.
Going from 0 to 100 will likely not work or be sustainable, apart from the first few days. You have to progressively build capacity.

If you want to start a side business, for example, plan with your situation in mind. You’ve got work, school, a family, and things that you can’t abracadabra away. If one an hour is all you can afford to work on that side gig, then let’s make a damn good use of the hour.

Doing more than what you plan to do will give you more boost. Doing less will likely demoralize you. So it’s better to go from less to more than more to less

Eliminate projection bias

Use the timeline to plan. Bring the three versions of yourself to the planning table — the planner, the keeper, and the benefiter.

Allow the planner to be ambitious, but make sure the planner allocates what the keeper can afford regardless of how high or low their (or your) energy is.
I’m saying — the version of yourself making the plans should consider the version of yourself that will execute the plans.
You’d have to decide whether to be more committed or less ambitious at some point. Both are fine!
If you’re just starting, I recommend the latter! Find your rhythm and move from there.

Plans are not cast in stone. You can change your plans as you learn more about yourself and your capacity.

Keep the keeper on course and motivated to carry out the plans by bringing the benefiter into the picture.
Pitch your future to yourself. Consider who you are going to become and it’ll carry more weight than the pain or discipline of executing your plan.

My alarm carries a note of the reason I’m waking up early. My phone and computer background carry reminders too. Damn it, I even have a cheque on my desk that carries an amount I want to be able to cash at the end of the year.

Try an anti-vision too — who you’re going to become if you don’t execute your plan. An anti-vision is the opposite of your vision. It keeps me up when I feel like going back to bed when my alarm hits at 4 a.m. Gosh! I don’t want to be unsuccessful.

At every point of executing your plan, you are choosing your future self over your current self.

You have to choose between what you want now and what you want tomorrow. Because even though it feels good to sleep, party, be mindless, not work out or read now, it won’t be what you want tomorrow.

Tomorrow you’d want to be sound, intelligent, fit, wealthier, or speak and leave people in awe!
You have to choose tomorrow, today.

I published an article every day consistently on Medium until I hit 500 articles. It got me gigs, helped me find my voice, got me into rooms but it wasn’t easy. I wanted to give up many times.
Moreover, how do I write a letter to you on consistency if can’t get my own stuff together? It wasn’t just about me. I pictured you too, and myself writing to you and it kept me going. I haven’t stopped writing every day.

Make plans like this

With everything you’ve read so far in mind…

Start by setting a goal (for the benefiter)

Then set a timeline for achieving the goal (for the keeper)

Set milestones.

Milestones are significant points of progress in your journey. If you want to read 20 books, for example, every 5 books read could be a milestone, a win. The benefiter gets to show up 4 times in the journey to celebrate.

  • Assign tasks to the keeper. And break down these tasks into monthly, weekly, and daily tasks. Optimize your tasks for your milestones.
    So — you don’t have to read 20 books in one year, you just have to read 5 in 3 months and then head for the next milestone.
    If you don’t do this, what you have is a wish, not a plan.
  • Track your progress and recalibrate if you have to.
    Don’t be afraid to modify your plan. Do it as many times until fully optimal. And even then, modify.
  • I use Evernote and Google Calendar but the tools don’t matter. Use what you’re comfortable with.
  • Reach out to me here, if you need some help

Seek support and accountability.

You’re good on your own but you’re better with people.
Communities are one of the most effective ways of learning consistency and accountability

Before I could keep up with writing every day till today, I wrote for 100 days straight with a community of other writers and creatives, shipping their work every day! Join here

When I was late to ship my work, someone texted or called me. “Hey, I haven’t read your post today. Is everything okay? Do you need some help?” I did the same when my accountability partners were late to ship.

I may not be podcasting today if I wasn’t a part of The Carbon Almanac Community. And now we have published over a hundred episodes.
Jennifer and Leekei never let me doubt myself. We didn’t have it all figured out but it was easier moving together.

Even when our podcast was new we had hundreds of people in the community listen to it, cheer us on, and give us feedback.

There are so many communities online. Find a tribe of people like you. Join and be ready to contribute. Here’s one

It’s the third month of the year and maybe you’re falling behind with your plans already. But not anymore

Now, you know what to do.

Thank you for reading this letter.

See you in the next one.


P.S. If you’d like to read my letter every Saturday morning,
I mean… grab a cup of coffee (or whatever you take) while you download genius ideas that set you up for success, hit subscribe.



Olabanji Stephen

I see the world differently and attempt to interpret it in ways that inspire genius