I made this exact same move about 5 years ago and it was a total fucking disaster. All the things you count as accomplishments as an entrepreneur just look like

I made this exact same move about 5 years ago and it was a total fucking disaster. All the things you count as accomplishments as an entrepreneur just look like arrogant showboating during an interview. People hiring for fulltime jobs don't like to hear about how much creative freedom you had in the past, it means you'll be a rogue / pain in the ass. Product management sounds like the perfect setting for a creative yet technical cross-discipline entrepreneur, right? Nope. Most PMs have zero authority in an organization. They're far below engineers in some cases. Remember how you had a staff of 15 people? The people working for you are collaborators, not reports. The job is entirely about internal politics, compromising between business teams. It has been described to me as "holding an umbrella to keep management BS from distracting the engineers so they can work". You're literally holding a shit umbrella. It's completely thankless and unrewarding, if not somewhat degrading. In my case I used my sales skills to manipulate a freelance client into hiring me onto their product team without doing any due diligence. It was a disappointing, frustrating ordeal that lasted exactly 6 months before they pushed me back to consulting. Not worth it. Be an engineer. You get paid much more, have surprisingly much more respect in an org, and less frustration at work. But word of advice, do yourself a favor and shrug off that ego and accept your fate. If you were successful as a self-employed person you wouldn't be looking for a job, right? Allow yourself to say goodbye to who you were. If you keep that chip on your shoulder and sell yourself the way you're used to, you set unreasonable expectations for yourself and everyone around you. When you fail, the failure stings that much more. Taking a job makes you a part of that world. You'll be waking up every morning slogging your way to the office with everyone else, trying to impress your boss, climb the corporate ladder. If you were expecting a "retirement" you're in for unpleasant surprises. It's not that simple or easy. Your brain is hardwired for a different lifestyle, a different workflow. You've never been leashed before. You're not of that world. The only way to win is to let the self-employed ego die and rise again, a new citizen of planet cubicle