Hello! I have a jade plant which for the most part seems happy and healthy. At one point during the winter I over-watered it, and it started leaning. It's been leaning ever since. I think it may be getting too top-heavy, but I think the leaves look nice so I'm kind of reluctant to trim it. How can I go about strengthening the stem (and possibly straightening it)? Would staking it help? Should I re-pot it?

Leaning view:

Alternate view:

Do not repot. The plant needs strong light for a strong stem and compact growth habit. Do you have a brighter location you can use? A southerly facing window without blinds in the way would be ideal (assuming you're in the northern hemisphere). To deal with the lean, point it away from the sun and it will self-correct. Once it's growing straight up, try rotating the pot every time you water so that a new lean does not develop.

Thank you! I'll try to get it more sunlight and I'll point it away from the sun

As your jade plant continues to grow, pruning helps it develop a stronger trunk. I always avoided pruning my jade plants and then the branches would get too long and start to bend/curl. This video shows how to prune a jade plant and how you can easily propagate the trimmings and leaves. https://youtu.be/qucVW9eUNuY

Also try watering from bottom to develop more roots to anchor it.

Really, the only way to develop a strong trunk is proper light. Watering and pruning have nothing to do with it.