Picture the room. Your spouse is in a plastic chair under fluorescent light. A doctor they met ten minutes ago is asking whether you would want a breathing machine to continue if the next 48 hours go badly. Your spouse's phone is buzzing with a customer whose checkout is down. Neither of those problems is the real one. The real one is that nobody has ever told them what you would say.

This is the part of founder planning that gets skipped even by people who have a will, a trust, and a spreadsheet of every login they own. We plan for the death of the business and the death of the person. We rarely plan for the long, ambiguous middle, where you are alive, unable to speak, and everyone is guessing.

Two documents that sound like one

People use "living will" and "healthcare proxy" as if they were synonyms. They do different jobs, and you need both.

A living will (often called an advance directive or advance care plan) records your preferences about treatment: resuscitation, ventilators, feeding tubes, comfort-focused care. It speaks for you in situations you can foresee.

A healthcare proxy (also called a health care power of attorney or healthcare agent) names a person who can make medical decisions for you when you can't. It speaks for you in the situations you couldn't foresee, which is most of them.

The proxy matters more than the living will, because no document anticipates every fork. A form can say "no life support if there is no reasonable hope of recovery." It cannot tell a worried clinician what "reasonable" means for you. Only a person can, and only if they know you well enough to answer in your voice.

This is also a different instrument from the durable power of attorney that handles your money and business affairs. Many states keep the two separate, and the person you'd trust with your bank accounts is not automatically the person who should be deciding about your body. Check how your state words it, since the names and forms vary.

Why this isn't a hypothetical

It is easy to file this under "old people's problem." The data on end-of-life decisions says the decision-maker question arrives for almost everyone. In a widely cited study of older adults in the U.S. Health and Retirement Study (Silveira and colleagues, New England Journal of Medicine, 2010), a large majority of those who needed a treatment decision near the end of life could no longer make it themselves. Someone else spoke for them.

You are younger, so your odds are different, but the failure mode is the same. Accidents, strokes, and sudden illness don't check your age. And a solo founder has an extra complication: no business partner, no HR department, and often no one else who even knows what you do all day.

The burden the document is really for

Here is the part that changes how people write these forms. We tend to treat an advance directive as instructions to doctors. Its deeper function is to take weight off the people who love you.

Research on surrogate decision-makers shows that deciding for someone else is heavy. A systematic review by Wendler and Rid (Annals of Internal Medicine, 2011) found that a substantial share of surrogates report lasting emotional strain, including guilt, doubt, and symptoms of stress and depression, especially when they didn't know the patient's wishes. Many second-guess the choice for years.

There is good evidence that planning helps. In a randomized trial in Australia (Detering and colleagues, BMJ, 2010), older patients who received structured advance care planning were more likely to have their wishes known and followed, and their family members showed less stress, anxiety, and depression afterward.

Read that plainly: the conversation you're avoiding isn't morbid. It's the kindest thing in the file.

How to choose the person

Most people name their spouse without thinking, and for many that's right. But "closest to me" and "best at this job" are different tests. Ask a few harder questions:

  • Can they say no to a doctor? The role sometimes means disagreeing with confident professionals in a frightening moment.
  • Can they carry out your wishes when they'd choose differently? A proxy's job is substituted judgment: what you would want, not what they want for you.
  • Will they be reachable? Someone on a flight, in another time zone, or asleep with their phone off is a poor first choice. Name a backup too.
  • Is the load too much on one person? If your spouse would also be running to understand your business, consider splitting roles: one person for medical decisions, another for the business.

Then do the one thing most people skip: ask them. A person who learns they've been named while standing in a hospital corridor is making the hardest decision of their life with no preparation.

What to put in the directive

A good directive isn't a legal template with the boxes ticked. It carries your reasoning. Doctors and families respond to "what matters to me" far better than to a bare checklist.

Think about what a good day looks like for you. Is it being conscious and talking with the people you love? Being independent? Being out of pain? Where is the line past which you'd rather prioritize comfort? Write it in your own words and attach it to the formal form. When the situation doesn't match the form, those sentences are what your proxy will lean on.

Your next moves

  • Pick your proxy and a backup today. Write down two names with a sentence on why each fits. Check that neither is the person least able to be reached on a normal Tuesday.
  • Have the conversation this week. Ask each person directly: "Would you be willing to speak for me if I couldn't?" Then spend twenty minutes telling them what you'd want. Say it out loud once, even if it's awkward.
  • Get the state-specific forms. Your state's bar association, health department, or a hospital social work office usually offers free advance directive and healthcare proxy forms. Fill them in, sign them with the required witnesses or notary, and don't rely on an unsigned draft.
  • Write a half-page "what matters to me" note. Describe what a life worth continuing looks like to you and what would change your mind. Attach it to the directive.
  • Put copies where they'll actually be found, fast. Give one to your proxy, your backup, and your primary care doctor, and make sure the proxy can open the other copy from a phone at 3 a.m. A document locked in a safe deposit box is no use during a crisis that happens on a Sunday.

Where the business fits

The hospital doesn't care about your Stripe dashboard, but your proxy will. In those first days, the person making medical decisions is often the same person fielding calls from customers, and every minute spent hunting for a login is a minute not spent at the bedside. Keeping the medical documents and the business handoff in one findable place, with clear roles for who does what, is how you protect their attention for the thing that matters.

That's the idea behind Heirloom, a binder for solo founders that keeps your vault, your handoff, and your designated people together, so the person beside the bed isn't also the person hunting for the key. If you'd like to see how that looks, you can take a look at Heirloom. But the most important step needs no app at all: go ask someone to speak for you.