Ask HN: What would you do if you could start over?
Faced with the hypothetical chance to “start over,” many technologists say they would prioritize health, relationships, and time over chasing every career or startup opportunity. Common themes include exercising and fixing sleep earlier, changing bad jobs faster, investing and saving sooner, having children younger (or more decisively), and being less driven by others’ expectations. Alongside concrete regrets about missed crypto, FAANG offers, or grad school timing, several voices push back against obsessing over past choices, arguing that learning from mistakes and focusing on present opportunities matters more than replaying the past.
Career Choices & Timing
- Many would change industries or roles earlier: e.g., move into SV/FAANG/finance/startups in their 20s or 2010–2014 era, or leave tech/games/abusive startups much sooner.
- Several regret staying too long at “comfortable” or low-growth jobs; others regret joining hyped or “ethical compromise” companies and would prioritize fit, learning, and psychological safety.
- Some wish they’d focused earlier on high-prestige companies for signaling, others on smaller, more meaningful work or the arts instead of tech.
- A recurring theme: move on quickly when a job, manager, or team is toxic or stagnant.
Health, Sleep & Self-Care
- Fixing sleep (often via CBT-I, sleep hygiene, hormone checks, and lifting weights) is described as life-changing; multiple people wish they’d tackled insomnia earlier.
- Many would start serious exercise, martial arts, or strength training in their teens/20s, and drop alcohol or junk habits much sooner.
- Some regret internalizing “tough it out” masculinity and neglecting mental and physical health.
Money, Investing & Risk
- Common do-overs: buy Bitcoin/crypto early, load up index funds/Roth IRA/401(k), choose stocks over real estate, or join equity-heavy startups in 20s/30s.
- Others emphasize slow, steady saving over chasing unicorns and warn about the personal cost of “eat shit for equity” startup culture.
- Mixed views on risk: several wish they’d taken bolder bets when young; others would work less, avoid debt or grad school timing, and value stability.
Relationships, Family & Kids
- Strong but conflicting views:
- Some wish they’d had kids earlier or had more children.
- Others explicitly regret marriage/kids and would choose freedom.
- Several would prioritize building friendships, networking, and being a better partner; a few stress boundary-setting to preserve important relationships.
Learning, Education & Skills
- Regrets include wrong majors, delayed or mistimed grad school, switching from technical fields out of fear, and not specializing in a domain earlier.
- Others would worry less about “the perfect major,” focus on learning how to learn, and pursue degrees later purely for intellectual interest.
Location & Mobility
- Some would move to tech hubs or work abroad earlier; others found international moves and visa dependence limiting or isolating and would avoid or time them carefully.
Attitudes Toward Regret & Philosophy
- Several argue against obsessing over missed chances, emphasizing self-forgiveness, present-focused action, and the idea that painful detours often enabled current happiness.