Author missed option 3:<p>Do contract work at $250 an hour or equivalent compensation in shares at &gt;= series B funded startups.  Choose the level of risk you&#x27;re willing to accept in cash vs equity.  (Nearly) completely avoid politics and other office related BS.  Take vacation between gigs if you like.  Get a very broad variety of experiences at different companies and get a good feeling for what companies are willing to pay for should you decide to start your own.