Worked examples
25 households and the questions they came in with. Every number on these pages comes from the same projection the planner runs, and an automated test re-checks them on every build.
A dot marks the 17 examples where the projection found something the person hadn't asked about.
A pension that rises by a fixed dollar amount
“My pension increase is a fixed dollar amount, not a COLA. Every calculator I find only offers a percentage. What does mine actually do, and should I be converting to Roth before RMDs start?”
A Roth window in early retirement•
“What if I convert $50k a year to Roth for the next five years, and what does $80k a year look like instead?”
The exit that went the other way•
“I put $1,200,000 into that stock and $250,000 came back. What is a loss like that actually worth, should I convert to Roth against it, or sell the shares I still hold in the company before this one?”
The backdoor Roth, and what pro-rata does to it•
“Everyone says converting a non-deductible contribution is free. Is it? And what would emptying the whole IRA cost instead?”
Traditional or Roth, and the match you shouldn’t leave•
“Should I be doing traditional or Roth in my 401(k)? And what is this mega backdoor everybody mentions?”
What “fill the low bracket” actually costs•
“A common rule of thumb is to convert enough to fill the 12% bracket in my low-income years. What does that do compared with a smaller conversion?”
Seeing the RMD years before they arrive•
“What do our tax brackets look like once required minimum distributions start stacking on Social Security, and how does converting $80k a year before then change the picture?”
A two-year income gap•
“What if I'm out of work for two years starting next year? And what does converting $40k a year during that gap look like?”
The leap to self-employment
“If I quit next year and the business nets $60k growing 20%, how long do my savings carry the household, and what do my taxes look like?”
Runway on a raise
“When does the business run out of cash on this plan, and what does adding a $180k fully-loaded hire do to that date?”
Buying a business on a seller note•
“If I pay myself $150k, does this beat the job I left, and what does the note cost me along the way?”
The structure the business is taxed under•
“What would electing S-corp change, and if I incorporate to a C-corp before an exit, does it matter whether I do it now or in three years?”
The years before Medicare•
“How much can I convert to Roth in these low-income years without wrecking my health-insurance subsidy?”
Ninety days to decide on the options
“What does exercising actually cost me, and would it be different if they were non-qualified?”
Thirty days on the 83(b)
“Does filing the 83(b) actually matter, and what if the company doesn't take off?”
What the salary you pay yourself decides
“How much can I actually put away, and what does the salary I choose do to it?”
An exit, inside the rest of the plan•
“What does selling actually leave me, and does it change when we could stop working?”
Claim Social Security at 62, or wait for 70?
“What if we claim at 62 and take the $28,000, versus holding out for the $49,600 at 70?”
What the tax code does to whoever is left•
“If one of us outlives the other by a decade, what does that do to the taxes on the same money?”
House rich, and out of money at 77•
“We keep being told we're fine because of the house. Are we?”
The sale, and where you are living when it happens•
“My federal tax on this sale is zero because of QSBS. What does California do to that, and what if I establish residency in Nevada first?”
The giving you were doing anyway
“We give anyway. Does it matter whether the money comes out of the IRA first or goes to the charity directly?”
The state tax no rate table shows•
“I want the whole pre-tax balance in a Roth before RMDs start. New York's top rate is nowhere near California's. How much does the state actually take?”
The losses that outlived the income•
“The business is over and the losses were bigger than anything I earned. Is there anything left to do with them, or did they die with it?”
Maxing the plan, and what ends up funding it•
“My plan allows the mega backdoor. Is there any reason not to max it every single year?”
Reading an exit before signing
“If we take this round and later sell for $20M or $60M, what lands in my pocket after preferences and taxes?”