Decision Guides
Answers to the questions
that keep you up.
Framework-backed guides for the choices that shape a life. Career, money, relationships, direction. No fluff.
Life direction
What should I do with my life?
Stop trying to find one answer. Run three-month experiments toward the intersection of what you're good at, what pays, and what you keep coming back to when nobody is watching.
WRAP →
Should I move to another city?
Move if the new city aligns with your work, your relationships, and your 5-year self. Don't move to escape — the problems travel with you.
10-10-10 →
What should I do in my 20s?
Compound one hard skill, build a small group of high-agency friends, get financially literate, and take reversible risks aggressively. Optimize for optionality, not prestige.
Second-Order Thinking →
Should I have kids?
There is no 'ready.' Decide by values, not by fear or FOMO — and only if both of you actively want it. Ambivalence in one partner usually becomes resentment in the other.
Regret Minimization →
Should I get a pet?
Get a pet only if your next 10 years — travel, work hours, housing, budget, partner — can absorb one bad year of vet bills, behavior issues, or moves. It's a decade-long decision, not a mood.
Second-Order Thinking →
Should I adopt a dog or a cat?
Dog if you want a companion tied to daily routine, exercise, and social life — and you're home. Cat if you travel, work long hours, or live small. Match the animal to your calendar, not your aesthetic.
Pros and Cons →
Career
Should I quit my job?
Quit if the job is damaging your health, your integrity, or your future earning power — and you have 6+ months of runway or a next role lined up. Otherwise engineer an exit over 90 days.
10-10-10 →
Should I quit my job or stay?
Stay if the job is fixable and you haven't asked for what you need. Quit if you've asked twice and nothing changed, or if staying means becoming someone you don't respect.
Pre-Mortem →
What should I do when I hate my job?
Separate the fixable from the structural. Ask for the fixable in writing this week. Start interviewing for the structural. Never do both from the same emotional place.
Eisenhower Matrix →
Should I take the new job offer?
Take it if it beats your current role on two of three: total comp, growth trajectory, and manager. One-of-three is usually a lateral trap.
Cost-Benefit Analysis →
Should I start a business or get a job?
Get a job that pays you to learn the exact skills your future business needs. Start the business on nights and weekends until it can pay you a salary.
OODA Loop →
What should I do after being laid off?
In the first week: negotiate severance, file for unemployment, and take 3 real days off. In weeks 2-4: audit finances, refresh materials, activate network. Job-search from a rested position, not a panicked one.
OODA Loop →
Remote work vs office: which is better?
Remote wins for focus, autonomy, and life design. Office wins for early-career learning, weak-tie networking, and roles built on tacit knowledge. Pick based on where you are, not what's trendy.
Cost-Benefit Analysis →
Freelance vs full-time: which is better?
Freelance wins on autonomy, upside, and skill-sharpening. Full-time wins on income stability, benefits, and building institutional knowledge. Choose based on runway and risk tolerance, not the story you like.
Cost-Benefit Analysis →
Cofounder vs solo founder: which is better?
Solo if the business is a stable, cash-flow lifestyle or content company. Cofounder if it's venture-scale, capital-intensive, or requires two full-time skill sets you don't both have.
Pre-Mortem →
Should I go to grad school?
Go only if the degree is the licensing gate for the job you want — medicine, law, clinical psychology, academia. For everything else, the ROI rarely beats two years of focused work.
Cost-Benefit Analysis →
Should I learn to code?
Yes, at a working level — enough to automate, script, and read code. Full career switches are harder than they were in 2015; augment your current work first.
Second-Order Thinking →
Should I take the promotion?
Take it if the new work is what you want to spend the next 3 years doing — not for the title or bump. Managing people is a career change, not a reward.
10-10-10 Rule →
Should I negotiate my salary?
Always. The worst case is the same offer. Ask once, professionally, with a number backed by market data — companies expect it and rarely rescind for asking.
Pre-Mortem →
Should I take a sabbatical?
Take one if you have 12+ months of runway, a clear reason (rest, project, transition), and a return plan. A sabbatical without structure becomes anxious drift by month three.
WRAP Framework →
Education
Should I go back to school?
Go back only if the degree is a required credential for a specific role you've already talked to people in. Skip it for signaling, prestige, or 'to figure things out'.
Cost-Benefit Analysis →
What should I major in?
Pick a major that keeps three career doors open, not one. Combine a rigorous skill (CS, math, statistics, engineering) with something that trains your judgment (economics, philosophy, history).
WRAP →
Should I go to college or not?
Go if you know why you're going, can graduate without crushing debt, and want work that requires a degree. Skip or delay if none of those are true — a gap year plus a trade or apprenticeship often outperforms.
Cost-Benefit Analysis →
MBA vs work experience: which is better?
MBA is worth it for career switchers into consulting, banking, or big-brand product roles — schools ranked M7 or top-15. For most other paths, 2 years of focused work experience compounds faster.
Cost-Benefit Analysis →
Relationships
Should I break up or stay in the relationship?
Stay if the relationship is fixable, both people are trying, and the underlying compatibility is real. Leave if you've named the same issue three times and nothing changes.
Pre-Mortem →
Should I get married?
Marry only if you already act married — shared money, shared decisions, shared hard conversations — and the answer to 'would I choose them again today?' is a clean yes.
10-10-10 Rule →
Should we move in together?
Move in when you're solving a shared question — not to test the relationship. Testing by cohabitation almost always accelerates a mediocre relationship into a stuck one.
Pre-Mortem →
Should I cut off a family member?
Estrangement is a valid last step after boundaries fail — not the first move. Try structured distance and clear terms for 6-12 months before deciding the relationship is over.
10-10-10 Rule →
Should I relocate for love?
Move if the relationship is serious, the destination has a viable version of your career, and you both agree what happens if it ends. Don't move for a maybe.
WRAP Framework →
Money
Should I buy or rent a house?
Rent if you'll move within 5 years, if buying takes more than 30% of income, or if the local price-to-rent ratio is above 20. Buy for stability, not as an investment.
Cost-Benefit Analysis →
What should I do with my savings?
In this order: emergency fund (3-6 months expenses), high-interest debt, tax-advantaged retirement match, index funds. Skip stock picking, skip crypto until you've done the first four.
Cost-Benefit Analysis →
Buy vs lease a car: which is better?
Buy a 2-3 year old reliable car with cash or a short loan, and drive it 8+ years. Lease only if you need a specific new car for business, or write it off, and you drive under 12k miles/year.
Cost-Benefit Analysis →
Invest vs pay off debt: which is better?
Pay off any debt above 7% interest before investing anywhere except an employer retirement match. Below 5%, invest and let the debt sit. Between 5-7% is personal — psychology often matters more than the math.
Cost-Benefit Analysis →
Save vs invest: which is better?
Save what you'll need inside 3 years — emergency fund, near-term goals — in a high-yield savings account. Invest what you won't need for 5+ years in low-cost, diversified index funds. Anything between is judgment.
Cost-Benefit Analysis →
Should I buy a house now?
Buy if you'll stay 7+ years, have 20% down plus 6 months reserves after closing, and the total monthly cost is under 30% of take-home. Otherwise rent and invest the difference.
Cost-Benefit Analysis →
Should I refinance my mortgage?
Refinance if the new rate is at least 0.75% lower, you'll stay in the home past the break-even point (closing costs / monthly savings), and you're not restarting a 30-year clock late in life.
Cost-Benefit Analysis →
Should I lease or buy a car?
Buy used and hold 7+ years for the lowest lifetime cost. Lease only if you need the car for business write-offs, want a new car every 3 years anyway, or drive under the mileage cap.
Cost-Benefit Analysis →
Should I take out a loan?
Borrow only for assets that produce income or appreciate — education with clear ROI, a home you'll hold, a business with a plan. Never borrow for lifestyle or to preserve appearances.
Second-Order Thinking →
Health
Wellbeing
What should I do when I'm overwhelmed?
Stop deciding. Stabilize physiology first — sleep, food, movement, one walk outside. Then triage: what breaks in 48 hours if untouched? Do only that today. Everything else can wait a week.
Eisenhower Matrix →
Should I see a therapist?
Yes, if the same problem keeps returning, if a relationship or job is stuck on the same fight, or if you've been meaning to for a year. Therapy is maintenance, not emergency-only care.
10-10-10 Rule →
Morning or night workouts — which is better?
The one you'll actually do 4 days a week. Morning wins for consistency and mood; evening wins for peak strength and social gyms. Consistency beats optimal timing every time.
Pros and Cons →