– Fast-rising executive at a “MAMAA” company.
– Compensated well, but likely below her true market value.
– Wants to take a sabbatical, and travel.
– Contemplating an offer (i.e. a lower salary, but more stock (ISOs, RSUs) – asking her what kind of package she prefers) from a start-up with her former boss, and torn whether to slow down, or take the job.
– Active in the community, and supports causes important to her.
“Can I afford to take the sabbatical, and what impact does this have on my career track?”
“Can I afford to take a lower salary with this start-up? How should I negotiate my package?”
“How can I give back to the charities in a more meaningful way?”
+ Determined that even with a sabbatical, she can still retire early at 56. More importantly, realized that time is her most precious commodity, and obtained the courage to take the sabbatical.
+ Evaluated the start-up offer, and quantified the stock package that she’d be leaving behind. Determined that she can likely negotiate more stock with the trade-off of a lower salary, and gain the potential benefits of an 83(b) election with the start-up stock.
+ Established a Donor Advised Fund, and created a funding strategy with highly appreciated stock, that not only reduced her taxes but allowed her to support her community.
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