https://www.spreaker.com/podcast/self-employment-success-let-s-make-sense-of-this-sh-t--7076289
Become a supporter of this podcast: https://www.spreaker.com/podcast/self-employment-success-let-s-make-sense-of-this-sh-t--7076289/support.]]>enBusiness© 2026 Let's Work This Sh*t Outhttps://d3wo5wojvuv7l.cloudfront.net/t_rss_itunes_square_1400/images.spreaker.com/original/e304d80d9a89ed63cb573c490f4e277e.jpghttps://www.spreaker.com/podcast/self-employment-success-let-s-make-sense-of-this-sh-t--7076289Tue, 14 Jul 2026 17:54:48 +0000CaseyLet's Work This Sh*t Outself@senseofthisshit.comThis 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,...
Become a supporter of this podcast: https://www.spreaker.com/podcast/self-employment-success-let-s-make-sense-of-this-sh-t--7076289/support.]]>falseepisodicSupport the podcast!https://www.spreaker.com/episode/understanding-invoicing-mistakes-net-30-vs-due-on-receipt--72970167
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. I'm Casey. Today we tackle a common invoicing mistake that slows down cash for one-person businesses. Many freelancers set net thirty terms because clients request them. However that choice often stretches payments out further than needed. Instead consider defaulting to due on receipt when your revenue sits under one hundred thousand dollars. This approach brings money in faster because it removes the built-in delay. You still confirm terms with your CPA for your specific setup. The reality is most solo operators lose weeks of float by defaulting to net thirty without checking. For example send a short email reply that says thanks for the project here is the invoice due on receipt to keep things moving. That simple line sets the expectation right away. Meanwhile if a larger client pushes back you can offer net fifteen as

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Become a supporter of this podcast: https://www.spreaker.com/podcast/self-employment-success-let-s-make-sense-of-this-sh-t--7076289/support.]]>45887339-5a9e-4532-9c51-d16bf03b302dTue, 14 Jul 2026 15:53:14 +0000CaseyIn this episode, we cover Invoicing. The conversation opens with: Welcome to Self-Employment Success : Let's Make Sense Of This Sht. I'm Casey. Today we tackle a common invoicing mistake that slows down cash for one-person businesses. Many freelancers...
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. I'm Casey. Today we tackle a common invoicing mistake that slows down cash for one-person businesses. Many freelancers set net thirty terms because clients request them. However that choice often stretches payments out further than needed. Instead consider defaulting to due on receipt when your revenue sits under one hundred thousand dollars. This approach brings money in faster because it removes the built-in delay. You still confirm terms with your CPA for your specific setup. The reality is most solo operators lose weeks of float by defaulting to net thirty without checking. For example send a short email reply that says thanks for the project here is the invoice due on receipt to keep things moving. That simple line sets the expectation right away. Meanwhile if a larger client pushes back you can offer net fifteen as

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

Become a supporter of this podcast: https://www.spreaker.com/podcast/self-employment-success-let-s-make-sense-of-this-sh-t--7076289/support.]]>4311099,business,business-structure,employment,entrepreneur,freelance,llc,podcast,pricing,proprietor,self,self-employment,show,sole,sole-proprietor,solo,solo-business,structure,taxes,tipsfalsefullhttps://www.spreaker.com/episode/understanding-s-corp-election-the-60k-profit-threshold--72970127
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. I'm Casey. If you run a one-person business and your profit is climbing, the S Corp election question shows up fast. Many freelancers and consultants reach a point where filing as an S Corp can cut self-employment taxes, yet the switch only pays off once profit clears a certain level. The sixty thousand dollar threshold acts as the practical default for most solo operators. Below that mark the added paperwork and payroll costs usually outweigh the savings, so sticking with sole proprietor status keeps things simple. Once profit crosses sixty thousand dollars however the math flips in many cases. You form an LLC then elect S Corp status to treat part of your income as distributions rather than wages. That said the choice process stays straightforward. Track your actual profit for the year first. Compare the tax reduction

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Become a supporter of this podcast: https://www.spreaker.com/podcast/self-employment-success-let-s-make-sense-of-this-sh-t--7076289/support.]]>e9cba678-862a-42ad-aeb6-b6efdd1b1cb2Tue, 14 Jul 2026 15:47:22 +0000CaseyIn this episode, we cover S Corp. The conversation opens with: Welcome to Self-Employment Success : Let's Make Sense Of This Sht. I'm Casey. If you run a one-person business and your profit is climbing, the S Corp election question shows up fast. Many...
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. I'm Casey. If you run a one-person business and your profit is climbing, the S Corp election question shows up fast. Many freelancers and consultants reach a point where filing as an S Corp can cut self-employment taxes, yet the switch only pays off once profit clears a certain level. The sixty thousand dollar threshold acts as the practical default for most solo operators. Below that mark the added paperwork and payroll costs usually outweigh the savings, so sticking with sole proprietor status keeps things simple. Once profit crosses sixty thousand dollars however the math flips in many cases. You form an LLC then elect S Corp status to treat part of your income as distributions rather than wages. That said the choice process stays straightforward. Track your actual profit for the year first. Compare the tax reduction

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

Become a supporter of this podcast: https://www.spreaker.com/podcast/self-employment-success-let-s-make-sense-of-this-sh-t--7076289/support.]]>4231099,business,business-structure,employment,entrepreneur,freelance,llc,podcast,pricing,proprietor,self,self-employment,show,sole,sole-proprietor,solo,solo-business,structure,taxes,tipsfalsefullhttps://www.spreaker.com/episode/understanding-liability-insurance-e-o-vs-general-what-solo--72751148
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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 whether errors and omissions coverage or general liability fits our situation. For example, if you deliver advice or deliverables under fifty thousand dollars in revenue, one policy usually covers the main risks while the other adds little. Therefore, we need a simple way to compare them without extra cost. In fact, scope creep or a missed deadline can trigger claims that hit your personal assets. Meanwhile, choosing the wrong coverage leaves you exposed. Basically, this episode lays out the decision points so you can pick the default that matches your client work

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📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>7942c687-c70a-47bb-9c99-1cc1ca7be417Tue, 30 Jun 2026 03:24:19 +0000CaseyIn 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...
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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 whether errors and omissions coverage or general liability fits our situation. For example, if you deliver advice or deliverables under fifty thousand dollars in revenue, one policy usually covers the main risks while the other adds little. Therefore, we need a simple way to compare them without extra cost. In fact, scope creep or a missed deadline can trigger claims that hit your personal assets. Meanwhile, choosing the wrong coverage leaves you exposed. Basically, this episode lays out the decision points so you can pick the default that matches your client work

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>4771099,about,business-structure,context,definition,english,entrepreneur,freelance,grammar,language,llc,meaning,preposition,pricing,self-employment,sole-proprietor,solo-business,taxes,usage,wordfalsefullhttps://www.spreaker.com/episode/understanding-business-bank-account-when-to-split-finances--72744229
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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. Today we focus on the business bank account decision. The thing is, most banks treat a one-person operation differently than a larger company, so the paperwork and timing matter. If you are still under fifty thousand dollars in revenue, you can usually keep things combined for a while. Yet once you cross that line or land a bigger client, separating the accounts makes tax tracking much easier. The reality is that the IRS expects clear records, and a dedicated account helps you meet that standard without extra spreadsheets. Here is the thing though. You do not need a formal LLC to open one in many

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📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>a00f0c39-0a0b-4e46-a96f-2a667671c826Mon, 29 Jun 2026 17:17:42 +0000CaseyIn 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...
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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. Today we focus on the business bank account decision. The thing is, most banks treat a one-person operation differently than a larger company, so the paperwork and timing matter. If you are still under fifty thousand dollars in revenue, you can usually keep things combined for a while. Yet once you cross that line or land a bigger client, separating the accounts makes tax tracking much easier. The reality is that the IRS expects clear records, and a dedicated account helps you meet that standard without extra spreadsheets. Here is the thing though. You do not need a formal LLC to open one in many

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>3541099,business,business-structure,employment,entrepreneur,freelance,llc,podcast,pricing,proprietor,self,self-employment,show,sole,sole-proprietor,solo,solo-business,structure,taxes,tipsfalsefullhttps://www.spreaker.com/episode/understanding-client-boundaries-scripts-for-scope-creep-without--72379976
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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 and consultants especially hard when revenue stays under fifty thousand dollars a year. The thing is, most of us start out saying yes to everything because we want to keep the client happy. However, that habit eats into your time and your bottom line. Instead of guessing how to push back, we need clear scripts that protect your agreement without drama. Today we build a decision tree for handling these requests. If the extra ask falls outside your original contract, you have options that keep the relationship intact while you get paid for the added effort. We co

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📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>171c8ddf-6fe0-47d0-923b-cf1276991fbbSat, 06 Jun 2026 02:32:05 +0000CaseyIn 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...
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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 and consultants especially hard when revenue stays under fifty thousand dollars a year. The thing is, most of us start out saying yes to everything because we want to keep the client happy. However, that habit eats into your time and your bottom line. Instead of guessing how to push back, we need clear scripts that protect your agreement without drama. Today we build a decision tree for handling these requests. If the extra ask falls outside your original contract, you have options that keep the relationship intact while you get paid for the added effort. We co

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>3941099,business,business-structure,employment,entrepreneur,freelance,llc,podcast,pricing,proprietor,self,self-employment,show,sole,sole-proprietor,solo,solo-business,structure,taxes,tipsfalsefullhttps://www.spreaker.com/episode/understanding-pricing-freelance-work-the-rate-formula-that--72379783
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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 the business actually needs. That approach leaves gaps every time. Here is the default I give one-person operations. If your revenue sits under fifty thousand dollars, build the rate from your total costs first. Add the taxes you will owe, then divide by the billable hours you can realistically protect. The formula accounts for slow periods without forcing you to chase every lead. Once you see the number on paper, sending the invoice gets easier because the math already protects your cash flow.

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>2fdd834d-23fe-4be7-b42f-6bc5ff503939Sat, 06 Jun 2026 02:25:40 +0000CaseyIn 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...
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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 the business actually needs. That approach leaves gaps every time. Here is the default I give one-person operations. If your revenue sits under fifty thousand dollars, build the rate from your total costs first. Add the taxes you will owe, then divide by the billable hours you can realistically protect. The formula accounts for slow periods without forcing you to chase every lead. Once you see the number on paper, sending the invoice gets easier because the math already protects your cash flow.

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>3051099,business,business-structure,employment,entrepreneur,freelance,llc,podcast,pricing,proprietor,self,self-employment,show,sole,sole-proprietor,solo,solo-business,structure,taxes,tipsfalsefullhttps://www.spreaker.com/episode/understanding-self-employment-101-llc-vs-sole-prop-what-you--72379721
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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 personal liability for every contract and every bill. The reality is the right structure depends on your revenue and risk level. For example, if you stay under fifty thousand dollars and work with low-risk clients, a sole proprietorship often works fine at the start. That said, once revenue climbs or you sign larger agreements, an LLC adds a layer of protection that can save headaches later. We'll break down the tax differences, filing steps, and a simple decision point you can use right away. Plus you'll hear a short script you can adapt when you explain your struc

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>a83e323a-a9d6-4ffa-90b5-0e738411b554Sat, 06 Jun 2026 02:20:51 +0000CaseyIn 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....
Welcome to Self-Employment Success : Let's Make Sense Of This Shit. 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 personal liability for every contract and every bill. The reality is the right structure depends on your revenue and risk level. For example, if you stay under fifty thousand dollars and work with low-risk clients, a sole proprietorship often works fine at the start. That said, once revenue climbs or you sign larger agreements, an LLC adds a layer of protection that can save headaches later. We'll break down the tax differences, filing steps, and a simple decision point you can use right away. Plus you'll hear a short script you can adapt when you explain your struc

Subscribe for weekly explainers — no guru fluff, just tactics you can apply this week.

📩 Have questions or want to share your experience? Reach out at self@senseofthisshit.com.
💛 Join Our Supporters Club ($3 a month) 💛 Ad-free listening + early episodes — help keep independent media alive. Click Here: https://www.spreaker.com/podca...]]>4421099,business,business-structure,employment,entrepreneur,freelance,llc,podcast,pricing,proprietor,self,self-employment,show,sole,sole-proprietor,solo,solo-business,structure,taxes,tipsfalsefull