Tough Conversations Over Holiday Cigars - Cigar Life Guy

Tough Conversations Over Holiday Cigars

 In General, Joy of Cigars, Leadership, Legal, Life Insurance

This holiday season will be full of lots of cigars and for most of us also a great deal of family time. Unless you’re related to cousin Eddie, family time is usually a positive thing. It means quality time with loved ones. It’s a great time to finally have those tough conversations you’ve been putting off for years and start implementing new plans. When people are around their loved ones, it also causes them to be reflective. So, there’s no better environment to start a difficult conversation than over a great stick!

Don’t miss my completely free holiday gift to you at the bottom of this article!


Tough Conversations and Holiday Cigars

Estate or end-of-life planning starts with internalizing that we all die. It’s unpleasant to think about and natural to put off. Some families are in great shape. They have had conversations about what happens if Mom, Dad, their spouse, or etc. were to pass unexpectedly. They’ve also implemented a plan to carry out final wishes. If that’s you, great! Cut another piece of pumpkin pie, pour a good beverage, and light an Opus X.


Have a Plan or Starting Thinking About One

If the unexpected happened to you, would your family be taken care of, financially and otherwise?  If you have minor children, have you formalized how you’d like them cared for? Do your loved ones know what your final arrangement preferences are for burial, cremation, service or etc? They should include instructions beyond the vague, “something appropriate.” 
On a basic level do you have a plan to pay for your funeral? Do your loved ones know about your financial affairs? Who should they talk to (lawyer, financial professional, insurance agent, accountant) to settle your affairs?
Each of these questions could be an article or two to address. Depending on their complexity, they might require professional advice. I’m not trying to solve all your issues here, just to encourage you to start the conversation.

Three Tough Conversations to Consider

So you’re all set. You’ve got a will and executor lined up. You clarified your wishes for final arrangements. You’ve had some tough conversations with your spouse or adult children. They have a decent idea of what to expect with your finances. And, you’ve given some thought to estate planning issues if your assets are enough to warrant it. That’s great! Now, here are three things that you might have overlooked.


Digital Footprint or Assets

Years ago you didn’t have to worry about digital assets. Now, we all have them, even if they aren’t valuable to anyone else. Have you written down all your major online accounts (email, social media, banking, or financial) and instructions on how to access them? Do you own websites or domain names? Someone should be able to access them.

Medical Power of Attorney or Living Will

Have you addressed how you’d like to have medical decisions for you if you are unable to do so for yourself? Have you codified this in writing? Would you like heroic measures taken to try to save you even if you’re facing no hope of recovery? If you haven’t codified your wishes, someone else might make a decision for you that is contrary to what you want.


Long-term Care

It isn’t just death that causes us problems. According to the 2019 Genworth Cost of Care Study, 70% of adults will need long-term care in their lifetime. I know! That is a frigging crazy stat…and also very sobering. The median cost for a semi-private room in a nursing home is over $90,000 per year.

Long-term care insurance is an option for addressing some of those costs. It’s important to consider how you’d like to deal with the possibility of being unable to care for yourself. Having a plan is important even if you decide not to use long-term care insurance to help offset these expenses.


My Holiday Gift to You (No, It’s Not a Box of Cigars)

My friends at Tarkenton Financial have put together a great 24-page “Family Guidebook.” It’s great for dealing with some of these estate issues and starting conversations. 
Written by a respected estate planning attorney, it also includes a workbook you can use to organize your important information (names, contact info, accounts, logins, instructions, etc.). I’d be happy to email you a complimentary copy as my holiday gift to you. Send an email to or message me on social media @cigarlifeguy with your email address and a note that says “send me the family guide.”
Of course, if life insurance or long-term care insurance would help with your plans, Cigar Life Guy gets you non-smoker rates regardless of how many cigars you smoke so #PSSITA!


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John F. Kennedy reading while smoking a cigar.Leaves of the tobacco plant