Neither choice has to be forever. I would encourage you to take the CEO job. You will learn an enormous amount in that position that will benefit you later if

Neither choice has to be forever. I would encourage you to take the CEO job. You will learn an enormous amount in that position that will benefit you later if and when you become an entrepreneur. Live frugally. Earning $250k but living as if you made $25k (which is way more feasible in the Midwest than in the big coastal tech oriented cities) is an enormous opportunity. Doing that for 5-10 years will give you the sort of nest egg the vast majority of people can only dream of 10 years into the workforce. In the meantime, set the company up for success. Modernize it, and work on a succession plan for when you leave. Most people spend their entire lives working for money just to survive. You have the opportunity to do that for a handful of two of years to put yourself in a position where you can stop working for money for quite an extended period. Once you've done what you need to do to get the company into a place you're satisfied with, and you've put away some money to fund your dreams, you can pursue them with impunity. That said, it's unlikely that without you the company would be able to find a new CEO. People's livelihoods won't be jeopardized just because you decide the job isn't right for you or you're not right for it.