The First 48: The Hardest Conversation You’ll Ever Have as a Business Owner
As a business owner, you're a planner, a problem-solver, and a leader. You carry a huge weight—for your clients, your team, and your family. But there's one plan almost all of us avoid, and it's the most important one: What happens in the first 48 hours if you're suddenly gone?
It's a heavy topic. It feels morbid to even talk about. But creating this plan is not about death; it's about the greatest act of love and leadership you can offer the people who depend on you.
As a sounding board for my clients, I am often the first stop for questions but also the last person with FULL access to be of help in times of crisis. This list is curated from the experiences I have had and the horror stories I have heard from other bookkeepers during some of their hardest times.
1. Create Your Family's 'Access Key'
If something happened to you tomorrow, could your spouse or business partner immediately find the financial information they need?The truth is, most of this crucial information lives only in your head. That makes it completely inaccessible when your family needs it most.
Your emergency list should include:
All personal and business bank account numbers
Investment and retirement account logins
Life insurance policy details
401(k)/IRA beneficiary information
Safe-deposit box location
Password manager master password (or instructions for access)
Store this in two places:
A digital version in a secure password manager.
A physical copy stored in a fire-proof safe.
And most importantly: Make sure your spouse or trusted person knows exactly where to find the 'Access Key' document.
2. Lock Down the Legal Paperwork
Most families don’t have these basic documents in place. Without them, the state—not you—gets to make critical decisions for your family.
Every business owner should have:
A Will (including guardianship for minor children)
Durable Power of Attorney (for financial decisions)
Healthcare Power of Attorney
A Living Will / Healthcare Directive
You can set these up online for about $500, or around $1,500 with an attorney. This isn’t just a legal task; it’s an emotional gift to your family so they aren’t forced to make impossible decisions during a crisis.
3. Build a Financial Buffer for Grief
Grief is paralyzing. Your partner and kids will need time to process, and they cannot afford to face financial chaos on top of emotional trauma. Your company will need access to maintain operational costs during any transition, and often banking gets locked so help your bookkeeper maintain until further notice by having funds set aside for 30-90 days of runway.
Make sure you're personally protected with:
Term life insurance (10x annual income is the industry standard)
Emergency fund (6–12 months of expenses in a high-yield savings account)
Retirement accounts with spouse access (correctly set up with beneficiaries)
If these things aren't set up, your family could face sudden financial strain during an already overwhelming time.
4. Write the 'First 48' Cheat Sheet
This instruction sheet is arguably the most powerful tool in the entire system. Your family won’t know what to do first—or what not to do. Write out simple, clear instructions, including:
Attorney to call: [Name / Number]
CPA to call: [Name / Number]
How to file your life insurance claim
Instructions NOT to touch investments for six months
What bills are on autopay and from which account
This simple sheet removes panic, confusion, and rash, costly decisions, ensuring your family feels supported while they are still processing their grief.
5. Protect Your Business, Not Just Your Job
If your business is you, then without a plan, it dies the moment you do. Every business owner needs to put in place:
Buy–sell agreements (so your partners aren’t stuck)
Key person insurance (to cover revenue loss if you’re gone)
A formal business succession plan
An LLC held by your trust (for clean legal transfer)
If your company can't survive without you, you don't own a true business—you own a very demanding job with extra paperwork. This planning turns your business into a true asset that can support your family even after you’re gone.
6. A Trust Done Right: Avoid Major Mistakes
A well-structured trust can save your family literally hundreds of thousands of dollars in probate costs and months of agonizing legal headaches. But most trusts fail because:
Assets never get transferred (funded) into the trust
Beneficiaries aren't updated
There's no pour-over will to catch missed assets
A truly effective system includes:
Revocable Living Trust
Avoids probate
Keeps finances private
Protects your kids' inheritance
Pour-Over Will
Captures any assets you forgot to title into the trust
Guardian Designation
Determines who raises your children
Specifies how guardians receive financial support
As entrepreneurs, we are often guilty of thinking we’re invincible. We put ourselves last. We assume we’ll “get to it someday.”
But the truth is, your family, your team, and your clients depend on your leadership. Creating these systems is not about preparing for death—it’s about responsibility. It’s about protecting the people who trust you the most.
You can't take away their grief, but you can take away their confusion, their fear, and their financial stress. This plan is the most important system you will ever put in place.