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Planning
Planning: Turn a Vision Into a Tree You Can Execute
June 12, 2026·4 min read
A vision is a claim. A tree is what makes it doable.
"Launch a profitable SaaS in 18 months" is a direction, and directions are great for deciding where to point yourself. But you can't sit down and do a direction. The reason big goals quietly die isn't laziness — it's that they stay big. They never get broken into anything your Tuesday self can pick up.
Planning mode is where you take that one big claim and keep splitting it until the bottom of the tree is made of things you could honestly start this afternoon.
DMYOR
☰Plan▶Execute↻Habits◆Library✦Journal
VISIONLaunch a profitable SaaS in 18 months
MILESTONES ON THE PATH 3
Milestone
Validate the problem with 20 founders
5/5
Milestone
Ship the MVP and get the first signup
3/6
Milestone
Reach the first 10 paying customers
0/4
Building the tree, step by step
It's the same four moves every time, whether you're planning a company or a comeback.
1
Write the vision
One sentence at the top. The destination, with a time horizon attached so it stays honest.
2
Add your milestones
The three to six checkpoints that would prove you're actually getting there. These are meaningful chunks, not chores — 'ship the MVP,' not 'reply to that email.'
3
Break each milestone into actions
Concrete things with an obvious finished state. If you can't picture the moment you'd call it done, it's still too big — keep splitting.
4
Go deeper only where it earns it
A few actions need sub-steps. Most don't. Dmyor never forces extra layers on you — depth is something you add where the work is genuinely tangled, and nowhere else.
A simple test
If looking at a node makes you think 'where would I even start?' — that's the node telling you it isn't small enough yet. Split it until starting feels obvious.
Status flows down the tree
Here's a small thing that saves a lot of annoyance: when you mark a milestone active or done, its children follow automatically.
Each state has its own color so you can read the whole plan in one glance — standby is blue, active is orange, done is green. Flip a milestone to done and you won't find its actions stranded in the wrong state underneath it. The tree always tells you the truth about where things stand.