Quit to Freelance? The Tax Nightmare No One Tells You About

Freelance Taxes

Core shift: Taxes stop being automatic, You must withhold for yourself or the first big invoice can turn into a shock bill. Big cost: Self-employment tax means you cover the full payroll-tax side, Not just income tax like a W-2 paycheck. Timing trap: Quarterly estimated payments may apply, Put deadlines on a calendar so you … Read more

Turning Your Old Boss into Your First Client: A Freelance Transition Playbook

Freelance Transition

Core move: Resign cleanly first, then show handover risks, then offer consulting as an optional stabilizer. Prep first: Build a private inventory of what you own, choose one “yes” outcome and one hard “no,” and keep your leaving story boring. Pitch angle: Frame it as risk reduction and continuity, with specific outcomes and limited availability, … Read more