Office Hours with Ilana Jacqueline

A private, one-on-one strategy session for advocates, creators, and people building a sustainable life and career around chronic illness. (Looking to consult on a business or startup? That’s this page. Office Hours are for individuals only.)


What Are Office Hours?

A focused 60-minute strategy session for individuals who want clarity and direction—on a project, an advocacy path, a career pivot, or how to navigate your own healthcare more effectively.

These sessions are NOT medical advice, patient advocacy casework, or therapy. I’m not your doctor and I won’t advocate FOR you—but I’ll teach you how to advocate FOR YOURSELF, and point you toward strategies and resources most people never know exist.

After a decade as an author, advocate, patient influencer, and consultant across the healthcare ecosystem, I’ve learned that most people don’t need a full consulting engagement. They need one powerful hour with someone who’s already traveled the road.


What Can I Help You With?

Career strategy for people with chronic illness (my favorite hour to spend). Taking the job you have now and engineering a transition into work that won’t break you—long-term planning when your energy fluctuates, building a parallel path before you’re forced to jump, turning expertise into consulting or remote work, and designing a career around energy, not just ambition.

Navigating your own healthcare—resources, not advice. I can’t be your doctor or give you the names of my own clinicians, but I can hand you the map and teach you to read it: options you may not have considered, how to advocate for yourself in appointments and denials, and how to build a real strategy for better care within a broken system.

Plus: creative direction and idea development, influencer and creator strategy, monetization and getting paid, books and thought leadership, PR and personal branding, and networking and opportunity creation.

Can Anyone Schedule a Session?

No—and that’s intentional. This is a working session built to produce the plan you’ve been struggling to finish on your own. Come with an idea, a milestone, or a decision and leave with concrete next steps. It is not a venting session or a therapy substitute. I screen every applicant and turn down sessions where I can’t genuinely move you forward—or where one of my free resources would serve you better.


What Past Clients Say

As a patient advocate, it’s difficult to find someone ahead of you willing to share their experience and help craft useful, actionable next steps. Ilana’s office hours were so helpful for me and I highly recommend working with her.

A patient advocate

Ilana was honest, supportive, and genuine during our office hour together. And…she encouraged me to reach out with any other questions through messaging. Now it feels like I am reaching out to a friend.

Melanie Lee, Patient Influencer

It was so ENERGETIC and POWERFUL! I left with hope for my dream and new ideas that I never had even thought about were a possibility for me. Forever thankful!

Bre Crisp, LCSW

Ilana has an exceptional ability to see the real problem underneath the problem you think you are bringing her. She quickly identified where Connective Truth’s message was getting diluted by too many ideas, too much explanation, and an instinct to defend the work before simply defining it. Her feedback changed not just the language on my pages and comms, but the way I was thinking about the organization itself. I left with a much clearer sense of what mattered, what could wait, and how to make the work stronger without making it bigger. That kind of clarity is rare.

Wendy Moore

How Much Does It Cost?

A 60-minute session is $475 (plus tax) and includes the full hour, handouts, and—where appropriate—introductions from my network. Before you book, please read these six things:

1. This is not a casual call. Come ready to make a plan—we’ll use every minute.

2. This is a small slice of what I do. These sessions are about 10% of my working hours; I turn down many requests when I can’t genuinely help or a free resource is the better fit.

3. Complete the intake form at least 72 hours before our call so I have time to review your responses. Incomplete forms may be rescheduled.

4. I do not offer free sessions. They’re first come, first served, and the price reflects my experience, time, and energy. I do not take insurance and these are not HSA-approved.

5. Follow-up sessions are $180.

For ongoing business consulting, separate retainer packages are available on request.


What Are the Next Steps?

1. Complete the intake form at least 72 hours before your session.

2. Schedule a time via my Calendly link.

3. Once approved, you’ll get a confirmation email and secure payment link. Your session is confirmed when payment is complete.

4. We meet via Zoom. Please arrive on time in a quiet space with your full attention.

Questions? Email me at ilanawrites@gmail.com.