Audience of One #044 - Jack Raines on Writing, Finances, Satire, & Regrets
Nov 29, 2023
Jack Raines, a writer and Columbia MBA student, discusses alternative life paths, the importance of travel and writing, financial priorities, satire, getting an MBA, and the value of fun. He reflects on regrets, publishing a book, developing writing skills, and the changing creator space.
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Create Work By Reaching Out
- Reach out directly to people doing adjacent work and offer to help or do a free project to prove value.
- Use DMs, email, or introductions to create roles rather than relying on one-click job applications.
Experiment With Side Hustles Safely
- Keep a full-time job while experimenting with side projects so you have salary safety.
- Aim to replace 60–70% of salary with side income before going all in.
Mix Large Firms, Startups, Travel, And Writing
- Work at both large and small organizations to learn different systems and cultures.
- Travel for at least two months when young and publish some writing online as proof of thought.