“What-if” Planning Blog

Learning from Those Who’ve Been There: How Real Stories Can Help You Prepare
When it comes to preparing for the unexpected, learning from those who’ve been there can make all the difference. That’s why we’re launching a new YouTube series featuring real conversations with widows, widowers, and experts about the impact of preparation—or the lack of it—on grief, finances, and moving forward. Our first interview with Lori LoCicero, co-founder of The Death Deck, dives into her personal journey through loss and the lessons she wishes more families knew. Watch now and start the conversation before ‘what-if’ becomes ‘oh, crap!’

Set It and Forget It: 3 Steps to Organizing Your Documents for a Stress-Free Future
Spring cleaning isn’t just for closets—your end-of-life documents need a refresh, too! If your important paperwork is scattered in drawers, on old hard drives, or (gulp) lost in the abyss of your email inbox, it’s time to get organized. In just three easy steps, you can ensure your loved ones have everything they need when they need it most—no scavenger hunt required. Let’s break it down and get your affairs in order!

When Thinking About the 'Unthinkable' Feels Too Hard — 5 Ways to Start Planning Anyway
Thinking about what would happen to your family if something happened to you or your partner can feel overwhelming. Your mind might race with questions: Who would pick up the kids from school? How would they get to the doctor? Who would be there for the everyday moments—like helping with homework or comforting them after a bad day? These thoughts can be paralyzing, making it easy to put off planning altogether. But instead of letting these emotions stop you, you can use them as a guide. This post will show you how to move past the fear and start making the 'what-if' plans your family needs—without the overwhelm.

A Valentine’s Day Special: The Ultimate Gift of True Unconditional Love
True love isn’t just about the present—it’s about ensuring your partner can live a secure and fulfilling life, even if you’re no longer there. This Valentine’s Day, give the ultimate gift: a plan that protects your loved one’s future, offering them stability, guidance, and peace of mind when they need it most.

Top Questions About What-If Planning: Part 2
End-of-life planning comes with a lot of questions, and we're here to help answer them. In Part Two of our common questions series, we tackle topics like how to introduce the conversation with family, cultural and personal factors to consider, and what to do if loved ones disagree with your choices. Get the guidance you need to create a plan that truly reflects your values and wishes.

Top Questions About What-If Planning: Part 1
End-of-life planning doesn’t have to feel overwhelming. In this blog, we’re answering five of the most common questions we hear about what-if planning—from convincing loved ones to start planning, to choosing the right executor, to making the process manageable. Whether you’re just starting or revisiting your plans, this guide will help you take practical steps toward peace of mind.

Your ‘What-If’ Checklist: Creating an Inventory of What Matters Most
Creating a personal inventory of your assets is a crucial step in preparing your “what-if” plan. This simple but powerful tool not only ensures your loved ones have clear guidance but also helps you make informed decisions about your future.

Christmas Special – Five Gifts to Wrap Your Legacy with Love
Give your family the ultimate gift this holiday season: peace of mind. Discover five essential ways to protect your loved ones with thoughtful end-of-life planning, from life insurance to heartfelt letters. These lasting gifts will be cherished far beyond the holidays.

No Memory Left Behind: How to Save Your Stories for Future Generations
Preserve your legacy with heartfelt strategies to keep your memories alive for generations. From writing letters and organizing photos to creating memory boxes and capturing traditions, discover practical and meaningful ways to ensure your story endures. Start today and give your loved ones the gift of your lasting impact.

De-Bunking the Top 10 Myths about Planning for an Unexpected Death (Because Guess Who’ll Be Picking Up the Pieces?)
Planning for an unexpected death isn’t just practical—it’s empowering. This post tackles 10 common myths about preparation, helping you create a ‘what-if plan’ that protects your family, secures your future, and ensures your loved ones are supported no matter what life brings.

Thankful for Today, Prepared for Tomorrow: Simple Steps to Plan for the Unexpected
This holiday season, take small steps to protect your family's future with simple, actionable end-of-life planning tips. From inventorying assets to creating "what-if" plans, our guide helps stay-at-home parents ensure their loved ones are cared for, no matter what. Start planning today to secure peace of mind for tomorrow.

Spooky Consequences of Not Having an End-of-Life Plan
While Halloween is all about ghosts and ghouls, the real scares often come from things left undone—like end-of-life planning. Without a plan, you risk leaving your family with unanswered questions, costly delays, and lifelong uncertainty. From “Lost Control from Beyond” to “Family Hauntings,” the consequences can be chilling. Now is the time to consider not only your own end-of-life needs but also how to support your spouse or partner in the event of the unexpected.
Don’t leave loved ones with a haunting legacy. Discover simple steps to start planning today.