Casey

Self-Employment Success : Let's Make Sense Of This Sh*t

Business EN ↓ 5 episodes

This show serves freelancers, consultants, and solo creators (28–50) who left or are leaving W-2 work and need plain-language business operations — not MBA theory or manifestation framing. We own the one-person business lifecycle: entity structure, 1099 taxes, pricing, client boundaries, insurance, and lightweight systems. We never overlap with therapy shows (`anxiety`, `cptsd`, `grief`) on burnout/healing narratives, or with `e-commerce-innovations-lets-make-sense-of-this-sht` on storefront mechanics. Every episode is a decision tree with a default recommendation ("if you're under $50K revenu...

Author

Casey

Episodes

Understanding Liability Insurance: E&O vs General — What Solo 30.06.2026 7:57

In this episode, we cover Insurance. The conversation opens with: Welcome to Self-Employment Success : Let's Make Sense Of This Sh*t. I'm Casey. If you are a solo consultant, liability insurance often sits at the bottom of your priority list until a client raises an issue. However, that gap can cost you real money when something goes wrong with your work. The thing is, most of us do not know wheth...

Understanding Business Bank Account: When to Split Finances 29.06.2026 5:54

In this episode, we cover Banking. The conversation opens with: Welcome to Self-Employment Success : Let's Make Sense Of This Sh*t. I'm Casey. A lot of solo operators run their first year or two of payments straight through a personal checking account because it feels simpler at the start. However, that choice often creates extra work once the numbers grow. Listen for the key context, practical ta...

Understanding Client Boundaries: Scripts for Scope Creep Without 06.06.2026 6:34

In this episode, we cover Scope creep. The conversation opens with: Welcome to Self-Employment Success : Let's Make Sense Of This Sh*t. If you run a one-person business, you know how quickly a simple project can turn into something much bigger. A client asks for one extra revision, then another, and suddenly you're doing work you never agreed to handle. That is scope creep, and it hits freelancers...

Understanding Pricing Freelance Work: The Rate Formula That 06.06.2026 5:05

In this episode, we cover Pricing. The conversation opens with: Welcome to Self-Employment Success : Let's Make Sense Of This Sh*t. I'm Casey. If pricing your freelance work feels like a constant guess, you already know the problem. You pick a number that covers your time, yet taxes and quiet months still eat the profit. The thing is, most people start with what a client might pay instead of what...

Understanding Self-Employment 101: LLC vs Sole Prop — What You 06.06.2026 7:22

In this episode, we cover Entity structure. The conversation opens with: Welcome to Self-Employment Success : Let's Make Sense Of This Sh*t. I'm Casey. If you just left a W-2 job or you're about to send your first invoice, one question shows up fast. Do you operate as a sole proprietor or set up an LLC? Most people start as sole props because the paperwork stays light. However, that choice carries...