Playbook

Oct 21, 2026

The Forfeit Line

Roughly half of all FSA accounts forfeit money every year, and for most of you the deadline is December 31. Here's the one-evening playbook for pulling back every dollar of benefits you already earned before the plan year resets.

Oct 14, 2026

The Budget Close

Your 2027 raise is being decided right now, in a spreadsheet you'll never see, by people who mostly haven't talked to you. Here's the playbook for getting your case into that spreadsheet before it locks.

Oct 7, 2026

The Sandwich Audit

Social Security announces next year's raise on October 14th, and Medicare's enrollment window opens the very next morning. If your parents are on Medicare, these 54 days decide what their 2027 costs, and most families never look.

Sep 30, 2026

The Seed Deposit

The government will drop 1,000 dollars into your kid's name, your employer might add 2,500 more, and most parents still haven't filed the one-page form. Here's the full playbook, plus where this account ranks against the ones you already use.

Sep 23, 2026

The Lock Desk

Thirty year money just hit a nineteen month high. The five levers that actually move your mortgage rate have almost nothing to do with shopping three lenders.

Sep 16, 2026

The Escrow Correction

A letter from your mortgage servicer is about to raise your housing payment by a few hundred dollars a month. You have roughly forty-five days to do something about it, and almost every lever is on your side of the table.

Sep 9, 2026

The Earnings Record

Your Social Security benefit is computed from a ledger the government has been keeping on you since your first paycheck. Almost nobody checks it. Here is the audit.

Sep 2, 2026

The Enrollment Dossier

Open enrollment opens in about six weeks and the average person will spend eleven minutes on it, most of which is clicking confirm on last year's elections. Here is the file to assemble now, in September, so that when the window opens you are choosing instead of agreeing.

Aug 26, 2026

The Credit Access Window

Home equity lines just hit their lowest rate of 2026. The move is not to borrow. It is to get approved for money you have no intention of touching.

Aug 19, 2026

The Receipt Vault

One account in the tax code is untaxed going in, untaxed while it grows, and untaxed coming out. Most people use it as a debit card at the pharmacy. Ninety minutes fixes that.

Aug 12, 2026

The Beneficiary Sweep

There is a document that outranks your will, quietly controls most of your money, and you probably filled it out in four minutes from memory during a new hire orientation. Here is the ninety minute playbook that finds every one of them and fixes the six ways they fail.

Aug 5, 2026

The Drawdown Drill

The Nasdaq just fell more than 10 percent from its high and August and September are historically the two worst months of the year. This is the rehearsal you run while nothing is on fire, so that when it is, you are executing a plan instead of inventing one.

Jul 29, 2026

The AI Research Desk

It is Fed day and Q2 earnings are flooding in at the same time. Here is the exact system I use to turn a firehose of information into a twenty minute morning routine, without becoming a full time news junkie.

Jul 22, 2026

The Higher for Longer Playbook

The Fed meets next week and almost nobody expects a cut. Rates have sat in the same spot all year and inflation refuses to quit. Here is exactly how to position your cash, your debt, and your fixed income while everyone else keeps waiting for a rescue that is not coming.