The shape itself
Start with two parallel lines that lean down to the right, then connect each pair with two more lines that lean up to the right. The result is a flattened "Z" stacked on a "Z" — exactly the silhouette of a lawn chair. Get the lines exactly parallel in pairs (top with bottom, left with left, right with right) and the chair already looks right.
Axial vs equatorial
Six bonds point straight up or straight down — those are axial. The other six lean off at about a 19° angle from horizontal — those are equatorial. The rule that saves you on exams: every equatorial bond is parallel to one of the ring bonds two atoms away. If your equatorial bonds look like they're pointing the wrong way, check that parallel.
Ring flip in one move
A ring flip pushes the two "up" carbons down and the two "down" carbons up — the chair inverts. Every axial substituent becomes equatorial, and every equatorial becomes axial. The faces stay the same: top stays top. So a 1,2-cis disubstituted ring stays cis after the flip — one is axial up, the other is equatorial up before; one is equatorial up, the other is axial up after. Bulky groups prefer equatorial because there's less 1,3-diaxial strain.
Common drawing mistakes
The two most common errors are (1) drawing axial bonds at an angle (they must be vertical) and (2) putting equatorial bonds at the same angle as axial ones. If you can't tell which is which, the substituents will fight you when you try to assign cis/trans.
Draw this on the whiteboard
Open the OChem Board whiteboard — benzene rings, wedge/dash bonds, and a clickable periodic table built in. No account needed.