The Money Layer
Most financial planning content aimed at us assumes the next phase is winding down. The math is different when the next phase is 15 productive years at a different shape of income. The category that works is not retirement planning. It is bridge economics. The two are not the same.
The single piece of advice that matters most: understand your runway in months, not years, and plan around lumpy revenue rather than steady income. A consulting practice or fractional portfolio does not produce a paycheck. It produces a check in February, two checks in April, nothing in May, three checks in June. Operators who carry a paycheck mindset into this phase make two predictable mistakes. They overcommit fixed expenses in the first six months because the early checks feel like a salary. They then panic in the first dry quarter and accept work they should have refused. The operators who get this right build a 12 month cash buffer before the transition if they can, and 6 months at minimum, and treat every check that arrives as inventory rather than income until the buffer is rebuilt.
The other piece of advice that holds almost universally: advisory equity is more often a story than an asset. The grant looks meaningful at the time of signing. The dilution, the liquidation preferences sitting above it, the vesting cliff, and the probability that the company never produces a liquidity event at all combine to make most advisory equity worth a fraction of its headline number. Take it when the cash component is real on its own. Refuse it when the equity is being used to substitute for cash. Most senior operators get this exactly backwards in their first year because the equity flatters their sense of optionality.
The briefs in this category will cover the runway math that supports a practice rather than a paycheck, the actual ranges on advisory and fractional equity in 2026 and what they translate to after dilution, the entity and tax setup that determines how much of your gross becomes net, and the operational problems (health insurance, accounting, cash flow, contracts) that derail more pivots than any strategic mistake.