Planning ahead
The documents, decisions and conversations that help families prepare for a parent’s changing needs.
Get to know Fifty And
Life gets complicated.
We make it clearer.
Real stories and practical help for families caring for parents and other loved ones.
01 / Our focus
The conversation
we want to start.
A parent needs more help. Siblings have different expectations. An important document cannot be found. Suddenly, families face decisions they do not feel prepared to make.
Fifty And brings stories, practical answers and resources to people caring for parents and other loved ones. Through honest stories, expert perspectives and practical tools, we help families ask better questions, have difficult conversations and find a useful next step.
What do you wish your family had talked about sooner? What did you learn the hard way? What could another caregiver do differently because you are willing to share it?
We want people to leave thinking, “I did not know that,” or “We need to talk about this.”
Caring right now
Daily care, safety, changing roles, sibling coordination and support for the person doing the caring.
Managing an estate
The practical, financial and family responsibilities that follow a parent’s death.
02 / Ask Fifty · In development
A way through
“What do we
do now?”
400+ topics
Personalized checklists.
Manageable next steps.
Ask Fifty is an AI tool in development that will provide personalized checklists to walk families through more than 400 topics involving aging parents, caregiving, planning and estate responsibilities—including situations and decisions many people do not even realize are coming.
We are connecting those situations with the information families need: which documents matter, who can make decisions, what needs to happen first, where disagreements may arise and when to involve a qualified professional.
A family might begin with, “Mom needs more help—where do we start?” Ask Fifty is being designed to ask follow-up questions and offer manageable next steps, with supporting sources and clear direction on when professional advice is needed.
Our website is the place to explore the project as it develops, including our plans for practical resources, a Family Care Binder and Ask Fifty.
03 / The podcast
Fifty and
Squeezed.
Fifty and Squeezed explores the experience of supporting aging parents while managing the rest of life, navigating changing family roles and taking responsibility after a loss.
Through candid conversations, personal stories and informed perspectives, the podcast opens up the questions families often struggle to discuss: Who is doing the caring? What have we overlooked? How do we talk about money, safety or the next stage of care?
Each conversation is designed to leave listeners with something useful: a question to ask, a conversation to start or a practical step to take. We are preparing the show and inviting contributors to help shape its early conversations.
Practical help, with a clear focus
More clarity. More confidence.
A next step families can actually take.
The resources, products and partnerships we explore should serve a real need for aging parents or help the people supporting them. Our focus is caregiving and family responsibilities, rather than general lifestyle content for everyone over 50.
04 / The voices behind Fifty and Squeezed
Curiosity meets
lived experience.
Host
Megan Taylor Harvey
Megan brings podcasting experience and a voice-acting career spanning video-game characters and commercial work. Watching her parents navigate their own parents’ care and loss has made her think about what she and her sister need to understand and plan for now. She brings curiosity, personality and the questions many of us are only beginning to ask.
Founder
Emily Deere
Emily has cared for parents, navigated caregiver challenges and carried the responsibility of an executor. She brings hard-earned lessons and a determination to make those experiences useful to others. Her goal is to help families recognize pitfalls sooner, ask better questions and avoid preventable confusion and conflict.
Together, they connect “What should we be asking?” with “Here is what I wish I had known.”
05 / Your experience can help another family
And this is where
you come in.
We are inviting people with lived experience, thoughtful experts, content creators and relevant partners to help shape this work. Your story, expertise or community could help shape what comes next. We would love to explore a contribution that fits your experience and interests.
We will agree on the scope, timing, content permissions and any promotional or commercial terms before making commitments.
Let’s talk
Let’s find the right
place for you.
Email Emily with the story, topic or collaboration that interests you, plus two times you could meet for a 20-minute conversation in the next two weeks. Please include your time zone.
hello@fiftyand.com ↗Our goal: one concrete next step and a realistic timeframe. If the timing is not right, a candid “later” is welcome too.
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