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One of the most surprisingly popular newsletters of the past year was the one on how acting as someone’s executor just might be the worst job ever. As we head into the holiday season, it seems a perfect time to continue the conversation about wills, estates, executors and the end of life.

Seriously. David Edey, the certified executor adviser (CEA) who described the terribleness of being an executor, believes a family chat during the holidays about estate planning could be a big stress reducer over the long term. Seniors, start a conversation with your kids about your wishes after you pass away. Adult children, start the conversation yourself if your aged parents don’t take the lead.

Here are some thoughts from Mr. Edey about families discussing estate planning over the holidays:

  • Not at Christmas dinner: Wait one or two days after the big family celebration. “It’s a delicate conversation,” Mr. Edey said. “You don’t want to say something like, “Can someone pass the turkey and, oh by the way, mom, what are you going to be doing about your will?”
  • Talk about the executor: Parents, tell your family who you chose for this position, and why you chose them. “You also have to make sure the executor is comfortable and understands what the responsibility is,” Mr. Edey said. “It will take up to up to 100 hours to settle out an estate and anywhere between 18 to 24 months. With the pandemic, it could take even longer.”
  • Locate pertinent financial information: Help the executor know where to find a copy of the will, documentation of financial accounts and digital assets like social media accounts. “There are digital platforms you can use, or you might want to keep it in a big red folder.”
  • Make sure the will is up to date: Many people don’t have a will at all, or they have one that is out of date and doesn’t reflect their current situation.
  • Keep your expectations modest: “Just open the door,” Mr. Edey said. “You’re not going to accomplish everything in just one meeting.”
  • Persist: Delaying increases the risk of never having a family conversation about a parent’s wishes. “You can’t have a meaningful conversation with somebody when they’re on a respirator,” Mr. Edey said.

For more on how to be an executor, check out Mr. Edey’s book. It’s called Executor Help: How to Settle an Estate Pick an Executor and Avoid Family Fights.

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Rob’s personal finance reading list

The cost of buying homes without an inspection

In a hot housing market, you put yourself at a big disadvantage if you make an offer conditional upon a home inspection. The cost of foregoing an inspection is covered in a report on an Ottawa lawyer who has seen a rise in the number of clients seeking legal recourse for problems that became apparent after they bought. Now for a first-hand account from a U.S. homeowner who has paid a fortune in plumbing bills since moving into a home that was not inspected.

Not enough risk

An interesting article in a publication for investment advisers about the risk of being sued by clients who feel that they lost out on gains because their portfolios were too conservative. Remember to take a long-term view in evaluating returns. One-year results are just a snapshot.

Sick of inflation?

These shopping apps help you find deals that will help keep your grocery spending under control.

Flood insurance is drying up

A CBC Marketplace investigation on how property insurance companies are reacting to the growing problem of flooding. A guest makes an alarming point: climate change may turn insurance into something only the wealthy can afford.

Ask Rob

Q: “We established a registered education savings plan for our son (now 30-ish) years ago. He has mental health issues that will prevent him from ever using it for higher education. He now has a registered disability savings plan. What options exist for dealing with the RESP money (about $30,000)?

A: It may be possible to transfer money from the RESP to your son’s RDSP on a tax-deferred basis. Canada Education Savings Grant and Canada Learning Bond money received in the account must be repaid to the federal government. Further options include transferring the RESP money to your registered retirement savings plan, or to another beneficiary. There’s some urgency to this decision because RESPs can only remain open for 35 years.

Do you have a question for me? Send it my way. Sorry I can't answer every one personally. Questions and answers are edited for length and clarity.

Today’s financial tool

I get asked a lot by parents for the name of books or blogs to help teach their teens about money. May I suggest Rajat Soni’s Instagram page? Lots of common sense thinking on investing, spending, housing and more from this financial professional.

The Money-Free Zone

The British folk artist Richard Dawson is an acquired taste that took me a while to acquire. Take a short cut by listening to Lily, from his new album Henke. It’s a collaboration with a Finnish band called Circle in which songs are named after plants. The guitar solo late in the song Lily is killer good.

What I’ve been writing about
  • The TFSA contribution limit is tied to inflation – so why are we not getting more room next year?
  • The millennial and Gen Z dream of home ownership is being exploited in ways that just make houses more expensive
  • It’s go-time for finding a job with better pay and benefits: Here’s a checklist of what to ask for

More Rob Carrick and money coverage

Subscribe to Stress Test on Apple podcasts or Spotify. For more money stories, follow me on Instagram and Twitter, and join the discussion on my Facebook page. Millennial readers, join our Gen Y Money Facebook group.

Even more coverage from Rob Carrick:

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