If you are driving any time it's a bit cold (even a bit, if the heater could be used at all basically) the built-in trip planner will be too optimistic to trust. If you do trust it, it may strand you. If it strands you, you
need a tow truck. Turn everything off because you need to preserve the 12V battery to be able to put it in tow mode. Familiarize yourself with the tow procedures (mostly how to jump the 12V battery if needed, and how to put it in tow mode) because the tow truck driver may not know these things.
As others have mentioned, use abetterrouteplanner.com (most folks call it ABRP). You can expand the settings to account for the temperature and road conditions. Doing so on a recent trip, ABRP was +-1% for almost all legs, whereas the built-in planner was off by 20-40% consistently (sometimes even when not using heat to try to make it to the next stop, and going slower than the speed limit).
ABRP
does optimize the route for lowered overall duration. This means it keeps you working the bottom end of the charge capacity, because it can charge faster at a lower state of charge. It also means more frequent stops. If you use ABRP, add a few extra percent on each charge and plan for it to be slower than it calculates (I lost one or two hours every day compared to its estimate). If you use ABRP in the car's browser, be prepared for a lot of lag when loading it, but it has a neat feature where you can adjust your actual state of charge compared to its prediction and replan the route if necessary. You can even get it to look up Level 2 charger in a real pinch.
You will not run out of charge if you follow directions and charge when told to.
While this might work well somewhere warmer or during summer, it is bad general advice with the current implementation. The built-in trip planner is great at giving you a estimate accounting for speed and elevation (which is fantastic), but that seems to be about it. When it comes to cold (and I really mean anything below 10C or 50F), it is dangerously optimistic. Even following its warnings of "oh shoot you're gonna have to go X mph to make it" will leave you stranded miles before the Supercharger in the cold. And it has you skip chargers that would otherwise be beneficial to your sanity, because it seems to optimize for lowest number of stops.
(Yes, I'm mildly bitter after my recent 2000+km trip that the built-in trip planner was completely hopeless for)