Holidays Mean Cigars (Of Course), Family, and ... Tough Conversations (Free Holiday Gift!) - Cigar Life Guy

Holidays Mean Cigars (Of Course), Family, and … Tough Conversations (Free Holiday Gift!)

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

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

This holiday season will certainly 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 very positive thing.  Quality time with loved ones.  When people are around their loved ones, often it causes them to become reflective.  It also presents a great time to finally have conversations that have been put off for years and start implementing plans.  Afterall, there’s no better environment to start a difficult conversation than over a great stick!

Have You Had a Tough Conversation with Close Family Recently?

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

If You Don’t Have a Plan Consider Starting to Think About It

If something was to happen 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 to be cared for?  Do your loved ones know how you’d like your final arrangements (burial, cremation, type of service, etc.) to be handled?  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 to talk to (lawyer, financial professional, insurance agent, accountant) to help settle your affairs?

Each of the questions above could be an article or two in and of themselves to address, and depending on their complexity, maybe require the assistance of professional advice.  I’m not trying to solve all your issues here, just encourage you to start the conversation.

You Said You’re Good.  All Set.  Here Are Three Things Maybe You Didn’t Address:

So you’re all set: Got a will and executor lined up.  Clarified your wishes for final arrangements. Had a conversation with your spouse/adult children.  They have a decent idea what to expect financially.  You’ve given some thought to estate planning issues if your assets are sufficient to warrant it.  That’s great — Here are three items that may be overlooked in many plans:

Digital Footprint/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 beyond us. Have you written down all of your major online accounts (email, social media, banking/financial) and instructions on how to access?  Do you own websites or domain names?  At a minimum someone should be able to access them.

Medical Power Of Attorney/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 to be taken to try to save you even if you’re facing no hope of recovery? If you haven’t codified your wishes appropriately 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 require long term care in their lifetime (I know! That is a frigging crazy stat…and also very sobering…) and the median cost for a semi-private room in a nursing room is over $90,000/year.  Long term care insurance is an option for potentially addressing those costs.  Whether you decide to use long term care insurance to plan for these expenses or not it’s important to think though how you’d like to deal with the possibility of being unable to care for yourself (or a loved on not being able to care from themselves)

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” 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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