It&#x27;s better for a growth business to use profits to grow, not as compensation. Plans like you describe are what typical profit-sharing bonuses look like in more mature companies (or ones that aren&#x27;t planning to ever exit).<p>The easiest fix is to set the expiry after you leave the company to ~10 years rather than 90 days.  In that case, you have your entire tenure + 10 years for the company to have some kind of exit.<p>If that were the case, you could simply exercise at the point when the stock was liquid and you would never have to pay tax before then.  There would still be reasons to early-exercise (to get the clock ticking on capital gains), but that&#x27;s something that incurs risk -- you never need to do it if you don&#x27;t want to (and you don&#x27;t lose the options if you don&#x27;t)