Straight answers on work, money, and the decisions behind a career.

Written from inside financial services and the businesses around it. The same questions come up every week: what a role really pays, what the first year is like, whether the thing someone read online is true. These articles answer them the way they would be said across a table, with the numbers and the sources attached.

No. 06

Is that insurance agency a pyramid scheme? How to tell

The Federal Trade Commission’s own test, what a legitimate commission hierarchy looks like next to an illegal one, and five questions to ask before the coffee meeting.

27 October 202614 minute readCareersStraight answers

Explained, simply

One confusing idea at a time, explained with something you already understand.

Four-minute reads. Each one belongs to a long read and links to it.

Explained, simply · No. 14

What are estimated taxes? Explained like four rent days a year

An employee’s taxes come out before the paycheck lands; a contractor is a tenant with four rent days a year and nobody collecting in between.

27 October 20266 minute readExplainedMoney

Explained, simply · No. 13

Median or average? Explained like a pickup basketball game

Ten players, one seven-footer, and why the midpoint of insurance agent pay tells you more than any average an agency chooses to show you.

27 October 20266 minute readExplainedMoney

Explained, simply · No. 12

1099 or W-2? Explained like running a food truck instead of working the grill

The difference between a paycheck and a commission check is the difference between a shift at a restaurant and owning the truck: who buys the propane, who pays both halves of the payroll tax, and who keeps the regulars.

27 October 20266 minute readExplainedMoney

Explained, simply · No. 11

What is an override? Explained like a referral bonus that never stops

The person who recruited you is paid a slice of every policy you sell, for as long as you sell; here is why that is legal, how the slice is sized, and the one place the comparison breaks.

27 October 20266 minute readExplainedMoney

Explained, simply · No. 10

What is a chargeback? Explained like a store return

You sold it, you were paid your cut, the customer brought it back, and the store wants the cut out of your next check: that is a chargeback, with the real dollars.

27 October 20264 minute readExplainedMoney

Explained, simply · No. 09

What is an advanced commission? Explained like getting paid early

An advance is nine months of a bonus handed over on day one, on the understanding that you give back whatever you do not end up earning.

27 October 20264 minute readExplainedMoney

Explained, simply · No. 08

What are renewals? Explained like a subscription you sold once

Being paid a small cut every month a subscription you sold stays active is a renewal, and stacking hundreds of them is the whole case for staying past year two.

27 October 20266 minute readExplainedMoney

Explained, simply · No. 07

What is commission? Explained like a server’s tips

A server’s tips and an insurance agent’s commission work the same way, with one twist: part of the tip can arrive before the table has finished eating.

27 October 20266 minute readExplainedMoney