1. Quality people will always be able to outshine gaps in their resume. The bigger question is really what do you do with your free time? For startups especi

1. Quality people will always be able to outshine gaps in their resume. The bigger question is really what do you do with your free time? For startups especially, they care about what you do during your gaps. It demonstrates initiative and ability to work in a startup environment, rather than just be an employee. 2. If it's in the contract, it will likely be enforced. It's a legal matter if it's in the contract, and the company will do what the contract says. 3. Most important is to first know what you bring to the table. In a PM/marketing role, you will need to have more flexibility than technical roles in terms of the things you're willing to do. As someone else here said, hustle like a madman. I can tell you from my own experience of quitting after working my first job out of university for 2 years, if you don't have a plan in place and an opportunity lined up, it's really easy to lose your focus and discipline. It's then really easy to lose all your savings. So preferably, hustle at night to network and find opportunities, work the 9-5 from 9-5. Most meetups and networking events are at night anyway. For day-long events, you can easily take vacation days. Now if you've gotten to the point where you absolutely hate everything you do, and you can't even bring yourself to wake up in the morning anymore to go to work, then you'll quit no matter what. Just beware that it's easy to lose your focus on the first time out.