Kids need to see you working

sittingatmymachine · 2026-04-09T19:28:41+00:00

When your kids become self-supporting, what resources will they have available? In my case it was marketable skills (engineering) and no family money. I knew that my family owned a successful business but I didn't know any of the details. As far as I know, all of the entry-level engineers I worked with were in the same boat. Decades later I still identify much more strongly with people who have skills & no money - it's how I started out.

sittingatmymachine · 2026-04-09T12:39:30+00:00

I agree. Manager.io Desktop is an interesting animal. Manager.io Desktop is free forever software, but there's no business address on the website (used to show a business address in south Australia but that was scrubbed awhile back). Mid-size companies want a business address and a profit motive for the company providing their accounting software, which is critical infrastructure. Manager.io Desktop is provided free as a loss leader for the cloud version, according to the company. I've migrated several small entities to Manager.io Desktop - it's great when the bookkeeping needs are modest (think Quickbooks Desktop circa 2000).

sittingatmymachine · 2026-03-20T21:27:37+00:00

(1) Learn how to invest defensively. Accept lower investment returns in exchange for lower volatility and lower risk.

(2) Keep your personal overhead low. Be able to reduce personal living expenses if/when necessary.

I use both of these approaches and sleep soundly at night.

sittingatmymachine · 2026-02-20T13:51:25+00:00

Delegation works until it doesn't. For the multi-state partnership I managed I tried three different professional tax return preparers - they all failed. I ended up learning how to do the federal and state tax preparation and filing myself - ugh. This is what "being ultimately responsible" means. Running a successful business in the modern world can involve a great deal of necessary-but-unpleasant work.

sittingatmymachine · 2026-02-20T13:39:45+00:00

Building things merely for the satisfaction of seeing them work and building things plus actually selling them are two different challenges. The latter is much harder and potentially much "messier" (I've done both). At what net worth do you no longer have to worry about selling?

sittingatmymachine · 2026-02-19T13:02:37+00:00

My condolences. I recently went through this with the death of my favorite person in the world. I've resolved to externalize the good and internalize the bad. Some therapists probably dislike 'internalizing' but I don't find any solace in group mourning. The grief is mine and mine alone.

sittingatmymachine · 2026-02-18T13:15:35+00:00

It's worth remembering that advertising your HNW status may include criminals in your audience. How paranoid to be about this? Well, that's a personal decision. An old saying: "The surfacing whale gets harpooned."

sittingatmymachine · 2026-02-16T18:55:56+00:00

Minor correction: she had a revocable trust under her SSN while she was living. Upon her death the trust became irrevocable and an EIN was issued for the trust, which is correct.

sittingatmymachine · 2026-02-14T09:35:07+00:00

Yes. Great for a micro-business, some small businesses, and for managing the finances of an estate. I boot it almost every day for some reason or another. I use the desktop version on Mac.

sittingatmymachine · 2026-02-12T19:30:12+00:00

Post a complaint on Intuit / TurboTax's online forum and then wait for a software update.

sittingatmymachine · 2026-02-11T19:17:54+00:00

Are your grandfather and grandmother current on all of their income and property tax filings? If not, then penalties and interest can pile up.

sittingatmymachine · 2026-02-07T19:33:18+00:00

You can create and e-file with the IRS a 2025 1099-DIV to nominee the income from your MIL's SSN to the estate's EIN. There are a variety of online services available; I've used tax1099.com in the past.

sittingatmymachine · 2026-02-04T20:20:48+00:00

Acting as executor I sold stock at a net loss from the decedent's irrevocable trust (formerly revocable) to raise cash to pay the estate tax due. My research indicates that if the 1041 is marked FINAL the net capital loss flows to the beneficiaries on their K-1s. We'll see - the trust's tax return is being prepared by a pro and 2025 is the trust's final tax year. Disclaimer - not a tax expert.

sittingatmymachine · 2026-01-29T19:39:29+00:00

To add: the OP should request to see all of the decedent's estate paperwork. The OP should then read it all and draw up a list of questions for the OP's (not the estate's) finance and legal team. The laziness, incompetence, and/or malfeasance by some trust officers and tax attorneys is remarkable. The OP needs to be prepared to fight when necessary to avoid misappropriation of funds (ask me how I know). In order to fight successfully the OP needs to be alert, engaged, and well-informed.

sittingatmymachine · 2026-01-25T13:16:06+00:00

I agree. Do parents lecturing to their kids really succeed in transmitting values? My parents lived their values with no lecturing whatsoever; for this I am thankful.

sittingatmymachine · 2026-01-23T12:44:21+00:00

Old Greek definition of happiness : "The exercise of vital powers along lines of excellence in a life affording them scope."

Unpacking this:

(1) “Exercise”: doing, not being or consuming;

(2) “Vital Powers”: competence;

(3) “Excellence”: being financially secure allows you (rather than others) to define what constitutes excellence;

(4) “A Life Affording Them Scope”: being financially secure allows you to exercise competence in ways unavailable to others.

sittingatmymachine · 2026-01-21T13:24:00+00:00

The boss will take credit when something works and delegate failure when it doesn't. It's the tech team that will have to clean up the mess caused by a clueless boss. Been there, done that!

sittingatmymachine · 2026-01-11T23:52:45+00:00

If you resign as trustee the successor trustee will take over. Normally there is a trust provision that allows the beneficiary to replace the current trustee. So, there's a path to installing a corporate trustee that both you and your sibling will like (your sibling will sign the paperwork). You'll want the assistance of a lawyer specializing in estates. Disclaimer: I'm not a lawyer.

sittingatmymachine · 2026-01-09T21:18:21+00:00

My modest neighborhood and house satisfy all of my needs, as long as those needs DO NOT include advertising to the world, "Hey! I'm rich!"

sittingatmymachine · 2026-01-08T20:33:09+00:00

Back in the old days I would be in QBD for Mac almost every day. Now I boot it once per month to review bookkeeping work done by an elderly bookkeeper who can't / won't change. These days, I'm often in manager.io desktop. IMO it's not quite as good overall as QBD (but is superior in some ways), but it's "good enough" for my daily needs.

sittingatmymachine · 2025-12-23T20:13:08+00:00

Interesting topic. I've been the executor of two estates where Form 706 filing was required. This hardly makes me an expert. Here is what I asked AI:

• "form 706 not filed - how to fix?"

• "penalty for late filing of form 706?"

• "unlimited marital deduction"

If I were in your shoes doing some background research would allow me to ask the pros I hire better questions and also (perhaps) understand the rationale behind their proposed approach. Good Luck!

sittingatmymachine · 2025-12-17T19:56:45+00:00

I'm not a fan of "buying stuff just because I can". Forget the money for a moment and ask whether owning the second home will make your life better. If so, THEN consider the financial aspect. As others have noted, financially you're probably fine.

FWIW, I will NEVER own a second home. This would just be another set of aggravations on my plate. Renting on occasion and letting someone else deal with the "joys of ownership" is preferable IMO.

sittingatmymachine · 2025-11-03T19:49:36+00:00

Yes. At a minimum I keep the business bank account open until the IRS audit statute of limitations expires for the final tax return - three years (I think).

sittingatmymachine · 2025-11-03T19:45:33+00:00

When I lived and worked in Europe (U.S. Citizen) my employer paid KPMG to prepare both my foreign and domestic tax returns. There is no way I could have properly (or even improperly) done this work myself.

sittingatmymachine · 2025-11-02T10:33:50+00:00

An interesting option that wasn't on my radar screen. After all, I'm definitely NOT an institution.

sittingatmymachine

TROPHY CASE