Should I _____ ?
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Structured AI analysis for career, learning, and financial decisions. No fluff — just data-driven verdicts, weighted scorecards, and actionable next steps.
Explore Decisions ↓How It Works
Every decision page follows a rigorous analysis framework.
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Find your "Should I ___?" question across career, learning, money, and side hustle categories.
Analyze
Get a weighted scorecard, honest pros/cons, risk assessment, and three realistic scenarios.
Act
Follow specific next steps with vetted resources. Listen to a 3-minute audio briefing on the go.
Decision Categories
Choose your area or browse all decisions below.
Career Decisions
Navigate job changes, promotions, and career pivots with structured analysis.
3 decision guidesAI & Jobs
Understand how AI is reshaping your industry and what moves to make.
1 decision guidesLearning
Decide which skills, courses, and credentials are actually worth your time.
4 decision guidesMoney Decisions
Evaluate financial choices with frameworks, not feelings.
2 decision guidesSide Hustles
Assess side income opportunities with realistic timelines and tradeoffs.
2 decision guidesBuilt on Analysis, Not Opinions
Every page uses a weighted scoring framework, cites its sources, and clearly states assumptions. See how scoring works.
Recent Decision Guides
The latest questions analyzed by our AI decision engine.
Should I Learn AI in 2026?
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Yes · 88%Should I Switch Careers at 40?
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Depends · 72%Should I Start a Side Hustle While Employed?
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Yes · 82%Should I Learn Python in 2026?
Should you learn Python in 2026? Structured analysis with weighted scorecard, pros, cons, risks, and realistic scenarios…
Yes · 91%Should I Invest in Index Funds?
Should you invest in index funds? Structured analysis comparing index funds vs active management with weighted scorecard…
Yes · 90%Should I Start a YouTube Channel?
Should you start a YouTube channel in 2026? Honest analysis with revenue expectations, time investment, weighted scoreca…
Depends · 68%