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Decision Guides

Honest, balanced breakdowns of the choices people lose sleep over — the case for each side, the questions that actually decide it, and how different advisors would weigh in. When you're ready, put your own specifics to a live debate.

Debate any decision — free

Business

Should I hire an employee or a contractor?Should we build or buy the software?Should I form an LLC or an S-corp?

Career

Should I quit my job to start a startup?Should I take the counteroffer or leave?Should I take the startup offer or the big tech offer?Should I switch careers into tech?Should I ask for a raise or find a new job?Should I take the remote job or the in-office job?Should I accept the promotion into management?

Education

Should I go to grad school?Should I do a coding bootcamp or a CS degree?Is an MBA worth it?

Life

Should I move to a new city?Should I go back to school in my 30s?Should I start a side business while employed?Should I relocate for a relationship?

Money

Should I buy or rent a home?Should I pay off debt or invest?Should I lease or buy a car?

Startup

Should I raise venture capital or bootstrap?Should my startup pivot or persevere?Should I sell my startup or keep going?Should I find a cofounder or go solo?