succession.

Succession is the domain that only applies if you own a business — and if you do, it's often the largest and most tangled part of the whole transition. The business has been identity, income, and structure all at once, frequently for decades. Leaving it is rarely a clean exit, and pretending it will be is how owners end up working five years longer than they meant to.

The questions are concrete and uncomfortable: who could actually run this without you, and have you prepared them? What's it really worth, as opposed to what you hope? When do you actually want to be out — a real date, not 'someday'? Family businesses add a further layer, where the succession plan and the family dynamics are the same conversation whether you want them to be or not.

Bearings asks whether you've put real planning behind the exit, or whether the business is quietly becoming the thing that keeps you from retiring at all.