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Ask HN: Seeking ways to improve my planning skills and follow-through
I’m good at routines and habits, so my baseline productivity is solid, but I often struggle to break down larger, abstract goals into clear, actionable steps. For example, goals like "get a higher-paying job with more interesting coworkers" can feel overwhelming unless I outline specific tasks like researching the job market, learning relevant skills, or setting clear milestones.

I’d like to get better at this planning skill, turning broad goals into manageable steps, and am looking for recommendations:

Practical books or articles on planning and goal-setting.

Useful frameworks or techniques you've personally tried.

Courses, coaching, or communities that focus on this skill.

I don't know any books or course about the subject. I can only share my personal approach. This is something I've learned in the context of breaking down potential client projects into early plans and estimatable chunks.

What I do for projects in early stages and personal goals is the following.

1. Take a big piece of paper (A2/A3)

2. Write the goal on the right-hand side of the paper

3. Try to visualize what the goal looks like

4. Then I try to visualize the step right before the goal would look like

5. Write that down and draw a line to the parent goal

6. Move leftward and repeat

In my experience, the further you move to the left side of the paper, the more concrete and actionable the goals are. This will lead to a lot of sub goals and tasks that can be prioritized, revisited and continuously refined. Within the context of software projects, I find it important to work on the definition of done for the goals. I redraw the breakdown many times during the early stages of projects, until it can be put into a project management tool or similar. For personal stuff, I always just stick to the paper method and keep the latest iteration.

It is harder with more abstract goals (become an tech lead for my team; become a trusted advisor for management; be able to read and comprehend new ML research on arXiv etc.). If you are in software, breaking down semi-large projects is a good exercise. For other areas, I recommend starting with a goal that is abstract, but also attainable within months.

I like washing dishes.

Every time I start with forks and spoons, then I wash cups, next plates and the big pans and pots last.

Every time I get to do anything I try to get small wins and increase difficulty over time.

Just ask what is the easiest task that can be done, and when you finish, next easiest task will be more difficult because you selecting tasks from a finite list of tasks.

The analogy still holds if ones technique is to star with the cleanest things (keeps the clean water clean) until you throw the nastiest pans into the already dirty water. We should be building systems that make everything the optimal level of difficulty for us.
speaking as a former professional pearl diver, you soak your big stuff (or anything burnt or covered in melted cheese) while you wash the small stuff. then you can almost just rinse the big stuff unless it's really burnt on.

other good tips for home dishwashing: https://www.goodreads.com/book/show/48594284-how-to-wash-the...

The best method that worked for me:

Change your location. Notice how your brain begins to change as you distance yourself from your daily distractions.

Practical:

- Book a flight to Europe (if you're in the US) for two weeks. Or book a flight to the US (if you're in Europe) for two weeks.

- Bring your laptop.

- Set a deadline for your project on the tenth day of your trip.

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That's because long term goals like that are probabilistic rather than deterministic.

You can follow the steps and still fail.

Where as washing the dishes pretty much has a guaranteed outcome.

You probably don't like taking the risk, or losing your investment of time and effort. So your brain doesn't like it.

big goals are always fuzzy and overwhelming. what works for me is breaking them down backwards, start with what success looks like, then ask what step comes right before that, keep moving step by step till you reach today. it turns the giant scary goal into small clear actions. also, keep revisiting and adjusting as you learn more. simple, effective, and helps avoid paralysis by analysis.

frameworks like GTD or PARA help but none beats clear incremental steps you trust.

Try David Allen’s Getting Things Done (GTD), part of which is the Natural Planning Model.
1. I found PARA (Tiago Forte) method to be helpful for self.

2. PMP Cert also talks of Work BreakDown charts but thats too official.

Its more like finding your own routine/pace which allows for some serendipity and pays your bills and keeps you interesting

I'm also terrible at long-term planning. What I've found helps a bit is a whiteboard on which I write down goals and break them down into smaller tasks.