Why long-term planning is not as good as you were taught

If you listen to my podcast or read my blog you know that I am a big advocate for short-term planning. I even developed a scrum-based personal productivity method called the Monthly Method that allows you to set and achieve your goals three weeks at a time. The question I often get from my readers and my clients is whether I ever use long-term planning and how to go about setting long-term goals. Today I want to answer the question of whether I ever use long-term planning.

long-term planning

The story behind embracing short-term planning

I was introduced to the concept of agile product development about five years ago when I was working for a fast-growing tech start-up. The product development team was using scrum to run their team. It was the first time I heard about Agile and Scrum. I studied economics during my undergrad. And it’s not a surprise that I was never introduced to such concepts before. I was amazed at how efficient and productive these guys were at shipping new products and features. I was inspired to try this method in my own life and in my personal productivity.

I applied the same scrum principles to finish my master’s a semester earlier. I later implemented these principles in a new job that I had. The scrum method worked really well despite the fact that I was using it in operations and supply chain, not product development. After few years of using this productivity method in my professional and personal life, I narrowed it down to the core principles of the Monthly Method. I have taught it to my clients and they have experienced incredible results from using it.

Why I generally don’t believe in long-term planning

So why doesn’t long-term planning work? In my experience and in the experience of thousands of companies who embrace agile product development, I can say that long-term plans rarely work. I would go as far as to say that they never work. You spend months developing this perfect plan that goes sideways the first month you start implementing it. All that time you spent creating the perfect plan is wasted. So why do it? I don’t believe in long-term plans because these plans rarely work. But does it mean that we should never look further than three weeks at a time? No. 

When long-term planning is helpful

I think having long-term goals is best when you have a lifestyle image, a lifestyle you want to have five or ten years from now. You have a picture of how your ideal day looks like.

  • What do you see outside your window?
  • What time do you wake up?
  • How many hours do you work?
  • Who lives with you in the house? Or is it an apartment?
  • Do you have kids? How much time do you spend with them?
  • What kind of things do you do on weekends?

Having a lifestyle image doesn’t require you to have everything figured out. You don’t need to know what job you’ll have. You don’t need to have the exact income you need to earn. As long as you can afford the lifestyle you dream about is all that matters.

Do I have long-term plans?

Yes, I have a picture of the lifestyle I want to have 5-10 years from now. I don’t know what I’ll be doing for work or what my business might look like. However, I know how many hours I want to work and how many hours I want to spend with my family. I don’t know which country it is going to be, as long as it matches the lifestyle that I want to have. And there are numerous countries that can provide me with this lifestyle at different price points.

I don’t need to know all the details right now. And that’s the beauty of it. The traditional goal-setting approach would tell me to be specific about the job I need to have, the income I need to be generating, the country I’ll need to be living in. I would have to have all these details figured out. And then I would have to create a five-year plan, a one-year plan, a one-quarter plan, a one-month plan. But the problem is that right now, in 2021, I don’t have enough knowledge to come up with all these details.

Imagine yourself 10 years ago being forced to come up with all the intricate details of your lifestyle right now. Would you know what career moves you would have to make? Would you know where you would have to travel? Would you know which books you would have to read? No. Most likely, you discovered all these nuggets of wisdom as you moved along. Answers reveal themselves during the journey. 

What long-term planning is good for

Long-term planning is ideal for the WHAT and the WHY. That’s when you can start journaling, reflecting on your life, unleashing your core values and getting to know the true you.

  • What do you really want?
  • What do you really value?
  • What are your core values?
  • Where are you the happiest?
  • What brings you calm?
  • What brings you the most negativity at the moment? What would your life look like without it?
  • Why do you want to show up to work every day?
  • What contribution do you want to make in this world?
  • What makes time fly?
  • What tasks in all your jobs did you enjoy the most? And why?
  • What do you want to do on the weekends?
  • What do you want to do in the evenings?

You need to know WHAT lifestyle you want and WHY. There is nothing worse than running enthusiastically in the wrong direction.

If you already have a long-term plan in place, ask yourself,

  • “Why do I want this job title?”
  • “What kind of lifestyle do I think I will get once I get this position?”
  • “Why do I want to make this much money?”
  • “How would my life change once I get to this income?”

Try to get to the lifestyle image you think this role or this income will give you. And why do you want to have this lifestyle?

The long-term plan answers the questions of WHY and WHAT.

Short-term planning answers the question of HOW

How do I get there? What do I need to do in order to achieve this lifestyle?

That’s where traditional long-term planning fails. If we start to think about the HOW and create a detailed 5-year plan with all the milestones and deadlines, it quickly becomes overwhelming. We need to know all the answers of HOW to get there right now when we are creating this plan.

But guess what. If you are at Point B and you want to go to Point C, you only know how to get to Point B because you’ve already done it. You can only create the perfect plan with deadlines and milestones for how to get from Point A to Point B. But you are not interested in repeating the same result. You want something new, something you’ve never had before. How on earth, are you supposed to know the HOW if you’ve never done it before?

We are taught to set a five-year goal, sit down and create a perfect plan, put it on our wall and execute on it religiously every single day for the next five years. It’s overwhelming. We don’t know where to start. What milestones should we put on our plan? How long will it take?

So what happens as a result? People either procrastinate on creating a plan or they simply give up because they realize that there is no way they can know all the answers and can create this perfect plan. And the fear of failing on ‘the perfect plan’ stops them from even trying.

And that’s the beauty of the Agile approach to goal setting:

  1. You don’t need to know all the answers right now.
  2. You can run experiments.
  3. You can test hypotheses.
  4. The truth reveals itself along the journey.
  5. You only need to have enough information to run the next sprint.

Sprint Planning in Action

First, you set a long-term goal that looks like a lifestyle image. And you ask yourself, “What can I do with the information and resources I have right now to get closer to that goal?”

“Yes, I don’t know all the answers right now. But let me test some hypotheses and see what works and what doesn’t. Let me engage with the real world, produce something, ship it and see how the world reacts to it.”

That’s what agile teams do in product development.

They would create a feature or a product that is far, far, far from perfect in a short span of time called a sprint. They would ship it. And the goal is to ship as fast and as often as possible and see how the world reacts to it. Based on the real feedback from real customers, they adjust the product and ship it again.

Clarity comes from action

How often we don’t start something because we are confused?

We’re overwhelmed because we don’t know all the steps we need to take in order to get to our goal.

I don’t know where to start. I don’t know what to do. I don’t know if this approach will work. There is no guarantee. No one had done it before. I have no one to ask. There is no book on this topic. How do I know what the first step is? 

There is a major lack of clarity when you set a goal. The bigger the goal is, the less clarity you have on how to achieve it. That’s the law of goal setting. And it’s one of the major reasons why people don’t start pursuing their goals.

Here’s the thing. Clarity comes from action. And the sooner you start pursuing your goal, the more clarity you’ll get.

You never get clarity from just sitting there and thinking about it. Yes. You can read an article or a book. But once you have the basic information, you need to start acting on your goal. More research will not give you clarity. More likely, it will result in even more confusion. The deeper you go into any topic, the more controversy you discover. The deeper you study any question, the quicker you realize that the answer is “It depends.” It depends on your situation, your environment, your country. And it’s up to you to go try things and discover what works for your particular case. No book, no article, no video can answer this question for you.

You are never stuck under short-term planning

And the other beauty of short-term planning is that you can never be stuck. If you’re only planning your actions for three weeks at a time, there are no huge decisions to make. You are testing small hypotheses. You are revealing the truth one sprint at a time.

When you are in the experimental state of mind, you are not stuck because there is no pressure to know everything. You are experimenting. Some experiments succeed. Some fail. But you succeed no matter what because you acquire knowledge.

The pressure of needing to know all the answers for the next five years is counter-productive. It paralyzes you. You are so afraid to take the next step because it might be the wrong step and all your plans will fall down like a house of cards.

Just a few weeks ago, one of the Monthly Method clients was able to get unstuck using the experimental mindset approach. He had a major business decision to make. He didn’t know all the answers. And he felt stuck. The traditional method tells him to make the right decision at the very beginning. The stakes are high. He would’ve spent months agonizing over which direction to take his business to. And once he made the decision, he would’ve spent the rest of the year questioning whether he had made the right decision. Such a waste of mental energy. So much worrying. He got unstuck after he embraced the experimental mindset and asked the right questions.

You don’t need to know all the answers when you start. Embrace an experimental mindset and wear an imaginary scientist’s hat.

This is a good video from Matt D’Avello that reminds us to start before we are ready.

More reflecting under short-term planning vs. long-term planning

You get to reflect on your life and your actions much more frequently under short-term planning. Under the Monthly Method, we do sprint retrospectives every month. I ask my clients questions that make them reflect on the previous three weeks. These questions make them learn so much about themselves, their productivity style, which actions have the highest ROI and which tasks can be ignored or delegated in the future. You’ll be surprised, how much you can learn about yourself by just reflecting over the past three weeks of your life.

Regular reflections on your life are what bring continuous improvement. It is incomparable to any other activity. Yes, you can read books and watch inspirational videos but reflecting on your own life and your own actions and results will be much more impactful.

This is when you analyze your hypotheses and experiments. Did they work? What did I learn? What can I do better in the next sprint? How do I get closer to my lifestyle image with the new knowledge I had gained over the past 3 weeks?

You get to learn a lot more about yourself, your preferences, what you like and what you don’t like, what works and what doesn’t. Once you consciously realize these things, you become a much more productive, happy, and balanced individual.

I think regular reflections on your life prevent you from having middle-life/quarter-life crises. Why do these crises happen? Because you run enthusiastically in the wrong direction. Society tells you that you need to have A, B, and C by a certain age. You don’t question these beliefs, you don’t reflect on whether it makes you happy along the process. You just run as fast as you can towards the wrong goal. Once you get there you FINALLY do your first reflection and realize “Oh crap, it’s not something I actually enjoy… Why did I spend the last 10/20/30 years pursuing it?”.

Monthly reflections allow you to catch yourself when you go off track, when you are off-balance. You see any signs of the wrong things in your life much earlier. And you can pivot, you can adjust, you can talk with the right people, you can set better boundaries, whatever you need to do that will make you happier in the long-term.

Short-term planning is better at building new habits

I talked more about it in the Sprint Planning article. It is much easier to convince your brain to do something difficult when you have a time limit.

I only need to wake up at 6 am for the next 3 weeks


I need to wake up at 6 am for the rest of my life.

After 3 weeks, the thought of waking up at 6 am is not that scary anymore. And you can do it for another 3 weeks. And then for another. And then it’s a solid habit that you’ve to build in just 3-12 weeks that will serve you for the rest of your life.

This approach also serves as a filter. We are told there are so many habits we can adopt that will change our life. A good example of such a myth is that reading 50, 100, 200 books a year will make you successful. I debunked this myth in this article.  In reality, most of these habits won’t change your life. And if you do them for 3 weeks and see no impact on your life, you just ditch them. No hard feelings. And you don’t get to feel like a failure for not doing them ‘for the rest of your life.’

Plan – Do – Reflect – Adapt

You feel like a failure most of the time under long-term planning

You feel like a failure every single second until you hit your 10-year goal. Seriously. And since it requires you to create a “perfect” plan on Day 1, you quickly run into an issue of failing to execute on that “perfect” plan. You might meet your first deadline but then things go south. Actually, they don’t go south, it’s just the world releases a new set of knowledge for you to process, but that’s not how we are taught to look at this. We are taught to look at this as a failure because we haven’t reached the next milestone on time.

Think about it… Have you ever met a person who created a 5-year plan and met all the milestones and deadlines? I think if he exists, he lives in the unicorn land.

Long-term planning doesn’t teach you to celebrate progress and the new knowledge you acquire along the way. It doesn’t encourage you to be curious and open-minded. Because, God forbid, you learn something that will total revamp that perfect excel spreadsheet you created for the next 5 years.

Short-term planning makes you better at handling failure

This is a huge one. Many of us, the perfectionists, the Type A people, the A+ students have a broken relationship with failure. We think it’s the end of the world. We think failure means there is something wrong with us.

When you embrace short-term planning and an experimental mindset, you take failure as a data point. Again, think about the scientists. They don’t cry over data. They don’t look at the results of their experiments as a personal failure. They look at it as a data point. No matter what result they got.

You can do the same in your life and in your business.

Hmm… I thought this workout program would work really well for my fitness goals. But I don’t see any changes in my body composition. Ok, let me try another fitness program (more weight lifting, less cardio, maybe?) during the next three weeks and collect a new set of data.

Not seeing results from an activity says nothing about your worthiness as an individual. It is a data point that you need to collect and analyze. This data point will better inform your future actions.

This is the common feedback I hear from my students. They say this approach feels very liberating and easy. Yet, they are the most productive they’ve been in a very long time. It seems almost counter-intuitive. No drama AND results..?

How do you combine a high level of productivity with ease? By embracing an experimental mindset, short-term planning, and a better relationship with failure. And this what we do at the Monthly Method.

The feeling of ease allows you to take action towards your goals daily. The ease and calm allow you to show up for your goal. There is less drama in short-term planning because it gets rid of all the BS excuses, resistance, fears that your brain has when pursuing a big goal.


So… Is long-term planning always bad? No. It’s great to think 5-10 years ahead and imagine the lifestyle you want to have. However, embracing sprint-based short-term planning is what allows you to get there in a much quicker and drama-free way. Long-term planning is great for the WHAT and the WHY. Short-term planning is great for the HOW.

If you want to apply the agile-based productivity method to your life, let’s do this! I guarantee you’ll be amazed by the results you get in just three weeks.

Read next:
  1. The one question that stops my procrastination
  2. How to be consistent. Normalize, then optimize. The Rule of 10.
  3. Unconventional Productivity Tips from Reddit [April 2021 edition]

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