When health or caregiving is affecting your work, now what?

Health changes. Caregiving responsibilities change. Work keeps moving. And the rest of life does not politely wait its turn.

This work is for people figuring out how to live the life they want within the realities of their time, energy, work, health, caregiving responsibilities, and everything else that matters.

The goal is to develop practical ways to navigate changing circumstances and make choices about work and life that reflect what matters most to you and the realities of the life you’re actually living.

The life you’re trying to maintain may have been built around a different capacity than the one available to you now.

Chronic illness, caregiving, and life after caregiving rarely affect only one part of life. Work, health, relationships, responsibilities, finances, expectations, available support, and your own wants can all operate at the same time, often by different rules.

A demanding workday may collide with pain or fatigue. A change in someone’s care may arrive in the middle of a deadline. A caregiving role may shift or end while its effects on identity, relationships, routines, or capacity continue. Help may technically exist but require more time, energy, coordination, or money than you actually have available.

Our virtual experiences create room to look at what is happening where these realities meet, including what they are asking of you, what they cost, what you can influence, what support is genuinely available, and what matters to you now.

What happens when the realities of your life meet each other?

Sometimes the problem isn’t that you are failing to manage everything. The realities themselves may not fit together.

Why work with Jennifer?

Jennifer’s coaching is informed by more than 25 years of HR experience, including workplace leave, accommodations, benefits, and employee relations, as well as her own lived experience navigating health-related and family care challenges.

She understands both the workplace systems that may be part of the situation and the human reality of trying to make decisions when health or caregiving responsibilities are changing what is possible. Her role is to coach you as you examine your circumstances, gather information, consider your options, make decisions, and determine what works for you.

Ways to work together

Start with the level of support that fits what you need right now.

Choose a single coaching session when you need a starting point, three sessions when you want more time to develop, test, and adjust a plan, or join Deep Roots Circle for ongoing connection, focused learning, and resources as circumstances continue to change.

Deep Roots Circle: Caregiving Membership
$95.00
Every 3 months
$35.00
Every month

Ongoing Deep Roots Circle membership for working women navigating caregiving. Stay connected through monthly conversation, focused learning, useful resources, and support as caregiving, capacity, work, relationships, and life continue to change.


✓ Monthly 45-minute virtual Connection Circle
✓ Monthly 30-minute virtual Focus Session
✓ Access to Focus Session recordings
✓ 10% off one individual coaching session per month
✓ 10% off eligible Deep Roots Circle programs and experiences

Deep Roots Circle

Deep Roots Circle: Life After Caregiving Membership
$35.00
Every month
$95.00
Every 3 months

Ongoing Deep Roots Circle membership for working women navigating life after caregiving. Stay connected through monthly conversation, focused learning, useful resources, and support as roles, relationships, capacity, identity, work, and what comes next continue to change.


✓ Monthly 45-minute virtual Connection Circle
✓ Monthly 30-minute virtual Focus Session
✓ Access to Post-Caregiving Focus Session recordings
✓ 10% off one individual coaching session per month
✓ 10% off eligible Deep Roots Circle programs and experiences
Deep Roots Circle: Navigating Health Membership
$35.00
Every month
$95.00
Every 3 months

Ongoing Deep Roots Circle membership for people navigating health-related issues while working, considering reducing their hours or stepping away from work, or preparing to return to work. Stay connected through monthly conversation in the Connection Circle, focused learning through the Topic Spotlight, useful resources, and support as capacity, circumstances, work, and life continue to change.


✓ Monthly 45-minute live Connection Circle (virtual)
✓ Monthly 30-minute Topic Spotlight (recorded)
✓ Access to the Deep Roots Circle Member Resource Hub
✓ 10% off one individual coaching session per month
✓ 10% off eligible Deep Roots Circle programs and experiences
Individual Coaching Individual Coaching
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Individual Coaching
$125.00
Limit 1 per order

You don't have to have everything figured out before you make your next move.

A private coaching session of up to 75 minutes for people navigating health-related issues or caregiving responsibilities that are affecting work, creating questions about work, or requiring decisions about what comes next.

You may be continuing to work, considering reducing your hours or stepping away, preparing to return to work, or simply trying to understand what information you need before deciding what to do.

During coaching, we take time to understand the expectations, demands, and realities influencing what is possible for you right now. That may include your own needs and capacity, your workplace, health providers, family or community, and the person or people you may be caring for.

Together, we identify what you know, what you don't know, what information you still need, and which questions matter most right now. From there, we can identify where you may need more information, what deserves your attention, and what you want to do next.

You may be trying to determine where to get reliable information, how to approach your manager or HR, what options you want to explore, or what needs to change for your situation to become more sustainable.

You do not need to leave the session with every answer. The goal is for you to leave with a better understanding of your situation, what needs your attention, where you can go for more information, and a starting point for what comes next.

If you want continued support, additional coaching sessions can help you develop a plan, put it into action, determine whether it actually works for you, and decide what needs to adjust as your circumstances change. Over time, coaching can also help you rebuild trust in your own judgment and develop a more intentional relationship with the people and systems influencing your decisions.

After purchase, you’ll receive information to schedule your session with Jennifer.

Active Deep Roots Circle members receive 10% off one individual coaching session per calendar month. The membership discount does not apply to the three-session package because that package is already discounted.

Want more than one session? A three-session coaching series is available for $345.

Coaching is not legal, medical, HR, benefits, or financial advice. It is designed to support your thinking, decision-making, and next steps.

Individual Coaching

Individual Coaching:  3-Sessions Individual Coaching:  3-Sessions
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Individual Coaching: 3-Sessions
$345.00
Limit 1 per order

You don’t have to figure everything out in one conversation.

Three private coaching sessions of up to 75 minutes each give you time to work through health-related issues or caregiving responsibilities that are affecting work, requiring decisions, or changing what is realistic for you.

You may be continuing to work, considering reducing your hours or stepping away, preparing to return to work, or trying to determine what needs to change so your situation is more sustainable.

Across three sessions, we take the time to understand the expectations, demands, and realities influencing what is possible for you right now. That may include your own needs and capacity, your workplace, health providers, family or community, and the person or people you may be caring for.

Together, we identify what you know, what you don’t know, what information you still need, and which questions matter most right now. From there, coaching helps you develop a plan based on the information available to you, put that plan into action, and begin evaluating how well it works in real life.

Your circumstances may change. Other people may respond differently than you expected. A plan that looked workable may need to be adjusted. These sessions give us room to explore what is happening, what you are learning, and what may need to change along the way.

The goal is not to create a perfect plan or tell you what you should do. It is to help you make thoughtful decisions, take meaningful action, rebuild trust in your own judgment, and develop a more intentional relationship with the people and systems influencing your decisions.

After purchase, you’ll receive information to schedule your sessions with Jennifer.

This package is already discounted from the individual session rate of $125 per session. Deep Roots Circle membership discounts do not apply to the three-session package.

Coaching is not legal, medical, HR, benefits, or financial advice. It is designed to support your thinking, decision-making, and next steps.