Five large transactions this week, none under a plan. The honest read of that is in “What repeats” — these people keep the discretion because discretion is their edge. Yours is not. You have no inside information to shield yourself from, no blackout windows and no filing obligation, so the compliance half of Rule 10b5-1 has no Canadian analogue that matters to you. The behavioural half does.

What transfers is the structure of the decision: choosing the amount and the dates while you are calm, and writing them down, so that the version of you looking at a 41% drawdown is executing a decision rather than making one. In practice that is a one-page policy for whatever surplus sits in the holdco or in your personal accounts: how much goes in, on what dates, into what. Automatic contributions do most of the work.

Be honest about where it does not transfer. Your single largest position is the operating company, and you cannot dollar-cost-average out of it. A written policy for the liquid remainder does not address the concentration; it just stops you making the liquid part worse.