Financial Planning Isn’t The Shallow End

Financial planning, now that is actually where it is interesting, and that is the actual move from the shallow end of the pool to the deep end. Yesterday, this conversation.


Mr X, Medicare eligible due to SSDI (which was not correctly processed by the SSA, yikes, even after the client had done everything right, following my guidance precisely). Wife is non-Medicare eligible with plans to retire this year. Retirement savings exist, but careful work is likely required.


  • Income sources (obviously)

  • Health insurance costs (husband now situated on Medicare, therefore minimized. The spouse is key here, because she has access to pre-Medicare retiree health benefits from her large employer. Nothing said that was most efficient, because the APTC is based on current income, not financial means. If she was Miss Perfect, her premium can be $0 a month, entirely changing the income/expense projections from the first bullet point.

  • Portfolio construction & account strategy will create a situation where capturing $0 premium health insurance is a tax matter. Simple portfolio construction, and yet generating cash for income, can lead to tax-related ripple effects on the health insurance premium, where the worst case can be that the full sticker price would be $1500 a month ($18,000 a year).

Issues most people face:

  • Stock broker may be broadly aware (that’s the nice version) of these interactions.

  • Health insurance agent may not know any of this.

  • The idea that the broker can make up the difference, in performance, by $18,000 by his/her marginal line-item selection on a properly-diversified portfolio? Not great, to put it mildly, and also subject to randomness.

  • Single spot for the combination of these? That is the point of the Comprehensive Planning Service, which is unlikely to continue in its existing form, at its existing price. Your specific combination cannot fit into a pre-ordained plan. It is why I find the free assessments of your financial status, snapshots of your current situation, to be deeply flawed when there are not careful, specific projections of the future.

Mr X asked: What services are included?
Answer: I showed the free quoting tool for health insurance, and how sensitive it was to different levels of taxable income. That changes when both are Medicare-eligible as well. We touched on the fact that a line-item look at financial holdings would be required to not upset the balance, and discussed possible paths.

Mr X suggested: In your emails, why don’t you describe this as you have done here?
Answer: Every person’s individual combination will be so wildly different, that a simple description will not work.

Answer: II really don’t find self-promotion interesting, and I am no good at it.

Maybe I am making up the entirety of this Substack, off the top of my head, unedited (explains typos and poor grammar, like in my awfully-produced videos I actually do know the rules)? Yeah, maybe.

Do It Yourself? It doesn’t have to me with me, but do it yourself? Nah, it’s a bad idea on a singular topic, it is many times worse for the combination.

Let’s take time to laugh at myself (there always has to be time for that).

Official Website for the book (link).
Official Website for GH2 Benefits (link).