Tumbleweed Plan

Tumbleweed Plan Navigating Aging, Caregiving & Legacy Planning Find links to our SANDWICHED PODCAST series at linktr.ee/tumbleweedplan.

Tumbleweed is a purpose-driven B2B SaaS platform designed to support the Sandwich Generation — the 1 in 4 adults juggling careers, caregiving, and their own families. Founded by caregivers, for caregivers, we understand firsthand the emotional, logistical, and financial challenges families face.

Nearly half (43%) of full-time workers in the U.S. are managing caregiving responsibilities alongside their jobs — a num...
04/24/2026

Nearly half (43%) of full-time workers in the U.S. are managing caregiving responsibilities alongside their jobs — a number that has grown 13% since 2019, according to Guardian Life’s 2025 workforce report.

That means they’re coordinating care appointments between meetings. Managing medication schedules on lunch breaks. Lying awake at night worrying about a will that doesn’t exist or a sibling who won’t step in.

And most of them aren’t saying a word.

Not because it doesn’t affect their work — AARP research shows that 67% of working caregivers have difficulty balancing their jobs with caregiving responsibilities, and 27% have already reduced their hours. But because the workplace hasn’t historically been a space where caregiving is acknowledged, let alone supported.

Here’s what forward-thinking organizations are doing differently:
✅ Offering access to legacy planning and caregiving navigation tools
✅ Normalizing caregiving conversations — not just parental leave ones
✅ Providing benefits that meet employees where they actually are in life
✅ Creating flexibility before a crisis forces the issue

The companies retaining their best people right now aren’t waiting for burnout to show up in exit interviews. They’re building support in before it’s needed.

Tumbleweed partners with organizations to support caregiving employees with the tools, clarity, and guidance they need — before crisis hits. If you’re building or reviewing your benefits strategy, we’d love to connect. 💛

Did you know?According to Pew Research Center, nearly 1 in 4 U.S. adults (23%) is part of the “sandwich generation” — su...
04/21/2026

Did you know?

According to Pew Research Center, nearly 1 in 4 U.S. adults (23%) is part of the “sandwich generation” — supporting both a parent aged 65 or older and raising or financially supporting a child. Among adults in their 40s, that number jumps to more than half.

What makes it so exhausting isn’t just the volume of responsibilities. It’s the emotional labor of constantly switching roles: parent, caregiver, employee, partner — and somewhere in there, a person with their own needs that rarely make the list.

Pew’s research also found that sandwich generation caregivers are twice as likely to report financial difficulty and significantly more likely to experience emotional strain than those carrying only one caregiving role.

If that’s where you are: you’re not alone, and you’re not failing. You’re carrying an enormous amount, often with very little infrastructure to support it.

Planning ahead — even in small steps — is one of the most powerful ways to reduce the weight. Not by solving everything at once, but by making the path a little clearer for yourself and the people who depend on you. 💛

Myth: “Talking about death is bad luck — or at least bad for everyone at the table.”We understand why this feels true. T...
04/18/2026

Myth: “Talking about death is bad luck — or at least bad for everyone at the table.”

We understand why this feels true. These conversations carry weight. They bring up feelings most of us would rather not sit with. And in many families, the subject has simply never been part of the conversation at all.

Reality: The silence is often more painful than the conversation.

When families don’t discuss end-of-life wishes in advance, what fills that silence is conflict — about medical decisions, about what someone would have wanted, about who gets to decide. That conflict tends to land right in the middle of the hardest moments, when people are least equipped to handle it.

Research shows that families who do have these conversations experience less grief-related conflict, make medical decisions with more confidence, and tend to feel less guilt about the choices they made.

You don’t have to cover everything at once. You just have to start somewhere.

One question. One conversation. One person who knows what you’d want. That’s not morbid — that’s love with a plan. 💛

One of the hardest parts of caregiving isn’t the tasks themselves.It’s trying to explain what it’s actually like — to pe...
04/16/2026

One of the hardest parts of caregiving isn’t the tasks themselves.

It’s trying to explain what it’s actually like — to people who love you but can’t quite feel the weight of it — while being too exhausted to find the words.

This week, we’re sharing some language for a specific moment: when you need the people around you to understand what you’re carrying, not fix it.

For a partner or close family member:
“I know you want to help. Right now what I need most is for you to not try to solve it — just sit with me in it for a minute. I’m more tired than I have language for.”

For a friend who’s been distant:
“I haven’t been in touch because I’m running on empty. It’s not you. I just don’t have the bandwidth to reach out right now, and I’m still figuring out how to ask for what I need.”

For a manager or colleague:
“I’m managing some significant family caregiving responsibilities. I’m doing my best to stay present at work. I may need some flexibility in the coming weeks and wanted to be upfront about it.”

You don’t have to be articulate about your pain to communicate it. You just have to let someone in.

Save this for when you need it — or share it with someone who does. 💛

Did you know?The average person has more than 100 online accounts — and most families have no plan for what happens to t...
04/10/2026

Did you know?

The average person has more than 100 online accounts — and most families have no plan for what happens to them in an emergency or after a passing.

That means email archives, years of photos, banking platforms, active subscriptions, and social media accounts that may quietly remain online, get deleted, or become inaccessible forever — simply because no one knew the passwords.

Digital legacy planning isn't just for tech-savvy people. It's for anyone who uses a phone.

A simple digital plan should cover:
📧 Email and communication accounts
📸 Photo and cloud storage
💳 Subscriptions and auto-payments
🏦 Banking and financial platforms
📱 Instructions for your social media profiles

You don't have to organize everything at once. But writing down three accounts your family would need access to in a crisis? That's a 10-minute step that could save them weeks of frustration.

A complete legacy plan includes your digital life. Start there. 💛

Myth: "Estate planning is only for people with a lot of money."This belief stops more families from planning than almost...
04/07/2026

Myth: "Estate planning is only for people with a lot of money."

This belief stops more families from planning than almost anything else — and it's simply not true.

Reality: Estate planning isn't about what you own. It's about who gets to make decisions when you can't.

Without even a basic plan, here's what can happen: your family may have no legal authority to manage your accounts, no clarity on your medical wishes, and no roadmap for what you'd want. That creates confusion and conflict during an already overwhelming time — regardless of your net worth.

A basic plan doesn't have to be complicated. It covers things like:
• Who speaks for you if you become incapacitated (a healthcare proxy or power of attorney)
• Where your documents and accounts are stored
• What you'd want for your care
• Who takes care of your children, pets, or dependents

You don't need to be wealthy to have people who love you. And those people deserve clarity.

Start with one question: if something happened to you tomorrow, would the people in your life know what to do? That's where planning begins. 💛

Did you know?According to AARP's 2025 Caregiving in the U.S. report, 59 million Americans provide care to another adult ...
04/04/2026

Did you know?

According to AARP's 2025 Caregiving in the U.S. report, 59 million Americans provide care to another adult family member — more than a 40% increase over just a decade ago.

And a 2025 Guardian Life report found that nearly half (43%) of full-time workers are juggling caregiving responsibilities alongside their jobs — a 13% jump since 2019.

Caregiver burnout isn't a personal failing. It's the natural result of carrying something enormous without enough infrastructure to support it.

For many people, the challenge isn't the caregiving itself — it's doing it in isolation, without a plan, without the right resources, and without anyone asking how you're holding up.

If that's where you are right now: you're not alone, and you don't have to figure it out by yourself.

Clarity around care planning, the right tools, and a little support can make a real difference — not just for the person you're caring for, but for you. 💛

Myth: "You should be over it by now."This is one of the loneliest things a grieving person can hear — even when they're ...
04/02/2026

Myth: "You should be over it by now."

This is one of the loneliest things a grieving person can hear — even when they're saying it to themselves.

Grief doesn't move on a schedule. It doesn't follow neat stages, and it doesn't mean something is wrong with you if you're still feeling it months or years later.

Reality: There is no timeline for grief. There's only your timeline.

Grief can look like exhaustion, not tears. It can show up as anger that comes out sideways. It can feel like relief — and then guilt about the relief. It can disappear for weeks and return in an instant when a song plays in a grocery store.

That's not a setback. That's grief doing what grief does.

If someone in your life — or a voice in your own head — is telling you that you should be over it by now: you don't have to agree.

You're not behind. You're just human. 💛

What does it really mean to be "sandwiched beyond the traditional definition"?Denise Brown — founder of Caring Our Way a...
03/30/2026

What does it really mean to be "sandwiched beyond the traditional definition"?

Denise Brown — founder of Caring Our Way and creator of Caregiving.com — knows firsthand. She cared for both parents while running a business, navigating decision fatigue, and managing her family's emotional needs alongside her own.

In this episode, Denise and host Paul H. Richardson Jr. explore:
💬 Why finding support is far more complicated than people assume
💬 How caregiving left little room for self-care — until it was gone
💬 The power of community and the courage to begin again

🎧 Listen now: https://sandwiched.podbean.com/e/denise-brown_sandwiched/

In this episode of Sandwiched, host Paul H. Richardson Jr. talks with Denise Brown, founder of Caring Our Way and creator of Caregiving.com, about what it truly means to be “sandwiched beyond the traditional definition.” Denise shares her experience caring for both parents while running a busine...

Wayne Freeman Chong's caregiving journey started at just 21 — helping his grandmother. What followed was a lifetime of l...
03/20/2026

Wayne Freeman Chong's caregiving journey started at just 21 — helping his grandmother. What followed was a lifetime of lessons in empathy, guilt, forgiveness, and grace.

In this episode of Sandwiched, Wayne opens up about:
💬 A heated moment that changed his life forever
💬 Feeling torn between duty, love, and impossible decisions
💬 How guilt and love can coexist — and how grace transforms both

From his grandmother's quiet forgiveness to his mother's cancer battle, Wayne's story is a raw, honest look at what it means to be sandwiched between generations.

🎧 Listen now: https://sandwiched.podbean.com/e/wayne-freeman-chong/

In this deeply reflective episode of Sandwiched, host Paul H. Richardson Jr. talks with Wayne Freeman Chong, whose caregiving journey began when he was just twenty-one. What started as helping his grandmother soon became a lifelong lesson in empathy, forgiveness, and emotional strength. Wayne shares...

Myth: “I have to be strong all the time.”Reality: Strength includes pausing, resting, and letting someone else hold part...
03/18/2026

Myth: “I have to be strong all the time.”

Reality: Strength includes pausing, resting, and letting someone else hold part of the load.

If you need a tiny reset:
- Put one hand on your chest
- Take 5 slow breaths
- Text one person: “Today is a lot.”

You’re allowed to be human.

If your family is navigating serious illness, knowing these terms can reduce fear and confusion.Save this carousel for l...
03/14/2026

If your family is navigating serious illness, knowing these terms can reduce fear and confusion.

Save this carousel for later.

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