What you want to check of your spec is that there is a behavior satisfying Spec in which the formula
Q == /\ (state = START) ~> (state = RIGHT)
/\ (state = START) ~> (state = LEFT).
is true. Let's call that condition Possibly(Spec, Q). A condition of the form Possibly(Spec, Q) is not expressible in a linear-time temporal logic like TLA. However, given a TLA+ spec Spec such as the one you wrote and a formula Q, it is possible to find a formula F such that Possibly(Spec, Q) is true if and only if the formula Spec /\ F satisfies Q. The formula F is the conjunction of conditions of the form WF_vars(A) and/or SF_vars(A) where A is a subaction of the next-state action, meaning that A implies Next. For your example, you can let
F == SF_state(state=START /\ state'=LEFT) /\ SF_state(state=START /\ state'=RIGHT)
To understand what's going on, you should read the paper called "Proving Possibility Properties"; here's a link to the paper:
The paper is quite mathematical and not easy reading, but it's only 8 pages long (excluding the proof in the appendix that you needn't read).
Leslie