GREG ISENBERG

everything good in life sits on the other side of questions you've been quietly avoiding for months copy my 50+ questions to your notes app, set a quarterly reminder, and answer with brutal honesty 1. money lies: - what expense do i defend that's really just status purchase? - where am i calling it "investing" when it's just spending? - which customer segment costs more to keep than to lose? - what price am i keeping low because of my own money issues? - where are we "saving money" but losing opportunity? 2. founder delusions: - which metrics am i celebrating that don't matter? - what founder podcast advice am i using to justify bad decisions? - where am i calling it "community building" when it's just procrastination? - what vanity metric makes me feel good but pays zero bills? - what would my revenue look like if twitter disappeared tomorrow? 3. survival blindness: - what existential threat am i ignoring because it's inconvenient? - which cost center would i cut if revenue dropped 50%? - what part of my business dies if apple/google changes one rule? - where am i one client away from trouble? - what assumption about my market keeps me up at 3am? 4. personal growth: - what am i avoiding by staying busy? - what relationship am i neglecting because of "startup life"? - what would i do differently if i had $100M in the bank? - what advice am i giving others but not following myself? - what am i pretending not to know? 5. business truths: - who's copying us and doing it better? - what's the real reason customers choose us? - which competitor keeps me up at night and why? - what feature do customers love that i hate building? - what do users actually pay for vs what we market? - which customer complaints am i ignoring because they're right? - what would this look like if it was easy? - what metric am i not measuring because i'm scared to know? 6. ego check: - what am i too proud to copy from competitors? - which introduction am i too "important" to make? - what task am i "too senior" to do that's killing growth? - where am i picking prestige over profit? - what's the last time i admitted "i don't know how"? 7. relationship debt: - which relationship am i burning for short-term gain? - what conversation am i avoiding that could 10x the business? - who do i need to thank but my ego won't let me? - what bridge am i burning that i'll need next year? - which mentor am i ignoring because they're right? 8. uncomfortable truths: - what medieval torture would i prefer to looking at my metrics right now? - which team member am i keeping despite knowing better? - what part of my business is actually just expensive therapy? - where am i copying others instead of thinking for myself? - what would my 18-year-old self think of my current excuses? 9. real costs: - what's my actual hourly rate if i count all the "quick calls"? - which relationship will my current work schedule cost me next year? - what health issue am i ignoring by calling it "hustle"? - where am i trading sleep for tasks a $20/hr va could do? - which hobby did i kill by turning it into a "side project"? 10. money & meaning: - what am i charging too little for? - which revenue stream feels most like cheating? - what could i charge 10x for and still sleep well? - what am i doing for free that others charge for? - where am i trading time for money unnecessarily? these questions sting. but that's how real change starts. how to use these: block 2 hours alone turn off notifications write first answers that come to mind once completed, go through list and ask yourself if you were really honest review in 90 days watch your life change shared these questions in case they are helpful to someone who needs new year's 2025 resolutions when you've got these 50+ questions every 90 days?