If you listen to my podcast or read my blog, you know I’m a big advocate for short-term planning. I even developed an agile-based personal productivity system called the Monthly Method, which helps people set and achieve their goals three weeks at a time.
One question I often get from readers and clients is: Do you ever use long-term planning? And if so, how do you approach setting long-term goals?
Today, I want to answer this question — and explain when long-term planning is useful, when it isn’t, and how short-term planning can help you reach your long-term vision faster.
The story behind embracing short-term planning
About five years ago, I was introduced to agile product development while working at a fast-growing tech startup, later to become one of the few Canadian ‘unicorns’. The product team used Scrum, and it was the first time I had ever seen such a highly organized yet flexible approach to work.
At the time, I had a background in economics, not tech. But I was amazed by how efficient and productive these teams were at shipping new features. I decided to apply the same Agile principles to my personal productivity — and it completely changed how I work.
Using Scrum, I finished my master’s degree a semester early and later started 2 businesses. After a few years of refining these methods, I narrowed them down to the core principles that now make up the Monthly Method — a system I’ve since taught to clients who’ve achieved incredible results.
Why I generally don’t believe in long-term planning
So, why doesn’t long-term planning work for most people? In my experience — and in the experience of thousands of companies that have adopted Agile development — long-term plans rarely go as expected.
You can spend months developing the perfect five-year plan, only to have it go sideways within the first month of implementation. All that time spent building a flawless plan becomes wasted effort.
That’s why I generally don’t believe in traditional long-term planning. Instead, I prefer short-term, sprint-based planning, which keeps you focused, adaptable, and engaged with reality.
When long-term planning is helpful
Long-term planning is most useful when it’s about defining your vision — not your to-do list.
I recommend having a lifestyle image — a clear picture of what you want your life to look like five or ten years from now. Think of it as designing your ideal day:
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What do you see when you look out your window?
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What time do you wake up?
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How many hours do you work?
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Who shares your home — a partner, children, pets?
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What do your weekends look like?
Long-term planning is about picking a direction. Are we walking towards a legendary corporate career or towards building a lovely homestead in a rural part of your country?
This kind of long-term goal doesn’t require you to have every detail figured out. You don’t need to know your exact job title or income level. As long as you can afford the lifestyle you imagine, that’s all that matters.
Do I have long-term plans?
Yes — I have an approximate vision of the lifestyle I want 5–10 years from now.
I may not know exactly what kind of work I’ll be doing or what my business will look like, but I know how many hours I want to work and how much time I want to spend with my family. I don’t even know which country I’ll be in — and that’s the beauty of it.
Traditional goal-setting would tell me to define my dream job, income, and location in detail and then map out a five-year plan. But here’s the problem: I simply don’t have enough information today to make those decisions wisely.
Think about yourself 10 years ago — could you have predicted your current lifestyle, career, or relationships with perfect accuracy? Probably not. Answers reveal themselves along the journey.
What long-term planning is actually good for
Long-term planning is ideal for the WHAT and the WHY — not the HOW.
It’s great for journaling, reflecting, and discovering your core values. Ask yourself:
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What do I truly want?
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What do I value most?
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Where and when am I the happiest?
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What brings me calm — and what drains me?
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What contribution do I want to make in the world?
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Why do I want this specific job, income, or lifestyle?
There’s nothing worse than running enthusiastically in the wrong direction. Defining what lifestyle you want and why you want it ensures that your energy is spent wisely.
If you already have a long-term plan, dig deeper:
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Why do I want this job title?
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What kind of lifestyle do I think it will give me?
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Why do I want to make this amount of money?
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How will my life change once I reach that income?
Your long-term plan should answer the questions of WHY and WHAT.
Short-term planning answers the HOW
How do I get there? What do I need to do in order to achieve this lifestyle?
The “how” is where most long-term planning collapses.
When you try to create a detailed five-year plan with milestones and deadlines, you’re forced to come up with answers you simply don’t have yet. If you’re aiming for something new — something you’ve never achieved before — how could you possibly know the perfect steps to get there?
That’s why people often procrastinate on long-term planning or abandon it altogether. The perfectionism and fear of failure stop them before they even start.
The Agile approach: Focus on short-term sprints
Here’s the beauty of the Agile approach to goal-setting:
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You don’t need to know all the answers right now.
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You can run small experiments.
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You can test hypotheses and learn from real feedback.
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The truth reveals itself one sprint at a time.
In Agile teams, this is how product development works. A team ships a minimal version of a product — far from perfect — to see how the world reacts. Then they improve it based on real customer feedback.
You can do the same with your goals: set a long-term vision, then focus on the next three-week sprint. Ask yourself, What can I do right now, with the resources I have, to get a little closer to my vision?
Clarity comes from action
Most people don’t start because they feel confused or overwhelmed:
“I don’t know where to start.”
“I don’t know if this approach will work.”
“No one’s done this before — what if I fail?”
But here’s the truth: clarity comes from action, not overthinking.
You’ll never gain clarity by endlessly researching or planning. The deeper you go into theory, the more contradictions you’ll find. The answer to most questions is “It depends.” At some point, you must engage with the real world, try something, and learn from what happens.
Books and advice can guide you, but only experience can teach you what works for your unique situation.
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.
You are never stuck under short-term planning
Another reason I love short-term planning is that it keeps you moving. When you plan just three weeks ahead, every decision is small and manageable.
You’re not stuck trying to make life-altering choices — you’re running experiments. Some succeed, some fail, but all generate valuable knowledge.
Long-term planning, on the other hand, often paralyzes people. The pressure to make the right decision for the next five years can stop you from taking any action at all.
When you embrace experimentation, failure becomes data — not a reflection of your worth.
Reflecting more often: Short-term vs. long-term planning
Short-term planning allows you to reflect more frequently and learn faster.
In the Monthly Method, we hold sprint retrospectives after every sprint. Clients look back at what they’ve learned, what worked, and what didn’t. This process creates rapid personal growth and continuous improvement.
You learn from your own life instead of abstract theories — and that kind of feedback is far more powerful than any book or video.
Regular reflection also helps you avoid midlife or quarter-life crises. Those crises often happen because people run enthusiastically toward goals society told them to chase — without stopping to reflect. Frequent reflection keeps you aligned and adaptable.
The problem with long-term planning: constant failure mode
Traditional long-term planning sets you up to feel like a failure until you reach your 10-year goal.
Because it demands a “perfect plan” from day one, you’re bound to fall behind once reality changes — and it always does. Then, instead of learning and adapting, you feel like you’ve failed.
But no one — truly no one — follows a five-year plan without changes. The world moves too fast. That’s why short-term planning is more honest, humane, and effective.
Short-term planning helps you handle failure better
Many perfectionists and high achievers have an unhealthy relationship with failure. They see it as personal weakness rather than a source of insight.
Under short-term, sprint-based planning, failure becomes just another data point. Like a scientist, you gather information, test hypotheses, and adjust based on what you learn.
This approach feels liberating. My clients often tell me they’ve never been this productive and relaxed at the same time. No drama, just data — and real results.
Final thoughts on long-term planning
So, is long-term planning always bad? Not at all. It’s helpful for defining your WHAT and WHY — your values, your ideal lifestyle, your vision for the future.
But when it comes to HOW to get there, short-term planning wins. Planning in agile, three-week sprints allows you to adapt quickly, learn faster, and make meaningful progress without the overwhelm.
If you’re ready to apply an agile-based productivity method to your own life, try the Monthly Method. You’ll be amazed at how much progress you can make in just three weeks.
Read next:
- The one question that stops my procrastination
- How to be consistent. Normalize, then optimize. The Rule of 10.
- Unconventional Productivity Tips from Reddit [April 2021 edition]
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