Insights

Twice a Year

Jeremy Showalter4 min read
A couple holding coffee mugs on a balcony at sunset, looking out over rolling hills.

There is a moment most families know well. You are standing in the kitchen the night before a long trip, running the list in your head. Passports, the house, the dog. And somewhere underneath it, quieter, a second list you never quite finish. If something happened while we were gone, would the other one know what to do?

That second list is the reason we built Vigil Protocol. And it is the reason we built the check-in.

A living picture of your financial life is only worth something if it stays true. Accounts get opened and closed. A policy renews, or lapses. A trustee moves. A child has a birthday that triggers a change in their role in the estate plan. None of these are emergencies on the day they happen. They become emergencies later, on the worst possible day, when the picture you had in your head turns out to be years stale and nobody noticed.

That is why Vigil Protocol has a rhythm, a heartbeat. Twice a year, the two of you sit down together and walk through everything, on purpose. We call it the check-in, and it takes about the time of a long coffee.

What the semi-annual check-in covers

The semi-annual check-in is a guided pass through the household, one category at a time. Twice a year you confirm the whole financial picture is still true, area by area:

  • You confirm the account inventory is still complete.
  • You look at value drift, what grew, what shrank, what moved.
  • You check the access path on each account, the real answer to “could the other person actually get to this.”
  • You look at insurance and what is about to expire.
  • You look at the estate documents and whether the people named in them still match the people in your life.
  • You review the contacts, the professionals, the human beings someone would actually call.

And you walk away with a fresh runbook, current as of that morning.

Three moments to make the check-in a habit

Before a trip

This is the one people feel most. You are about to be unreachable, together, for a week or two. The check-in is how you leave knowing that if the call came, the other one is not starting from zero. You both walked the same picture before you got on the plane.

After a significant financial event

You sold the business, or part of it. You took the rollover. You bought the second home, signed the trust, made the large gift. These are the moments the picture changes the most and the moments people are least likely to write anything down, because they are busy living the event. The check-in catches the change while it is still fresh, before it quietly drifts out of sync with everything around it.

And just because it has been six months

Not every check-in needs a reason. Half the value is the habit between a couple, the standing agreement that twice a year you both look at the whole thing in the open, together.

What makes the check-in work

You are not doing it alone, and you are not doing it from memory. Vigil Protocol already holds the map. It already knows what it flagged since last time, what went stale, what changed. The check-in is where its observations become your decisions, where a drift it noticed in March becomes a question you take to a professional, or where a review triggers the memory of an account or asset you forgot to add to the Map. Never advice. Always the picture, surfaced for the two of you and the professionals you already trust.

When you are done, the Continuity Runbook is current again. The proof is refreshed. Whatever you were carrying in the back of your mind the night before that trip has an answer, and you both know it.

That is the whole idea. A living thing you keep true with a small ritual, twice a year. Your house in order and kept in order.

Nothing breaks if you are gone tomorrow. That’s the promise to each other.

Jeremy Showalter
Jeremy Showalter

Co-Founder, Vigil Protocol. Chief Business Officer of Swan. Former CEO of Pique AI, acquired in 2021. Thirteen years at Microsoft across marketing, sales, and operations. MBA, University of Chicago; MA Science and Technology Policy, George Washington University; BS Engineering, Rose-Hulman Institute of Technology.

Vigil Protocol does not provide any investment, financial, tax, legal or other professional advice. We recommend that you consult with financial, legal, and tax advisors regarding your specific circumstances.

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