What does an outstanding career look like to you?

no real work, 500k

What do you mean by that exactly? What does it look like when someone is doing an outstanding job at work? Or the job itself is outstanding?

Become President at 88. Push country into recession

Monetary success: Get to FI so that I can take career risks. Maybe a "good enough" side business. Work success: Try smaller companies with a mission where my work matters to someone more than my manager. This will make me feel like I've lived a life with meaning. Don't care about titles and corporate ladder BS. Legacy success: Lead enough engineers along the way so they become independently strong and compassionate instead of jerks. Hopefully, they pass it forward themselves too. Happy to spend the rest of my time focusing on my family and then dying.