If I Dated My Hustles: Why Entrepreneurship, Writing, and AI Automation Feel Like the Ultimate Situationship

E ver wondered what it would feel like to date your side hustles? From writing situationships to high-maintenance personal branding, here’s a fun and relatable take on entrepreneurship, online business, AI, automation, and the messy love stories we call hustles. Forget flowers, chocolates, and dinner dates — the real love stories in my life aren’t found on dating apps. They’re in my hustles. Yep, the side hustles, main hustles, and “on-again-off-again” projects that have me up at 2 a.m. thinking about my future. If I actually dated them, some would be clingy, some would be heartbreakers, and others… total red flags I keep running back to anyway. Because let’s be honest: hustles and relationships? Same energy. Both come with drama, late nights, ghosting, toxic habits, and that confusing mix of “this is stressing me out” and “I can’t live without it.” So today, in the spirit of Couple Day, let me introduce you to the lineup of lovers in my entrepreneurial life. Writing – The Situationshi...