The January 2026 cohort of Joyfully Managed Worklife is now open!

If you'd like to explore a private cohort for your organization or a group discount, please see FAQs below.
The proven 4-week group experience to supercharge your effectiveness and lower your stress in 2026.

Is this true for you (or someone on your team)?  

  • You’ve got too much on your plate. You might even be waking up in the early morning hours with work stress on your mind.

  • Tasks are coming at you from everywhere - email, texts, Slack, project plans, calendar, goals documents, and during meetings.

  • Your days often feel like an endless series of frantic tasks, and you’re not sure it’s even on the right things to move your priorities forward. You end the day feeling like you really needed to get way more done than you actually did.

  • A habit of sometimes falling victim to procrastination makes you feel guilty and embarrassed when you get that email that starts, "I just wanted to follow up..." 

  • You have tried so many tools, but things are sometimes still slipping through the cracks.

  • You have a sense that this all could be working better together - that finding practical strategies to put into place would help. 

  • Your responsibility has gone up at work, and your systems need to catch up.


Look, we all want to do an incredible job at work + do it in a way that doesn’t feel chaotic. Is that too much to ask?!? 


You’ve heard all of the typical advice - spend less time on screens. Ruthlessly prioritize. Get a morning routine. Meditate. Boss up. 


But even finding time to implement those things feels impossible. You can’t pause to improve things, or it feels like the whole thing might fall apart .


I get it. I had to get to the point of being fully burnt out before I decided there had to be a better way. And I’ve spent years tweaking strategies and coaching others to implement. I want to share what I found with you. 

Introducing the Joyfully Managed Worklife group program. 

I’m inviting you to join this cohort experience so that we can create that reality together for you. You deserve that.

So what’s the Joyfully Managed Worklife experience?

This is a 4-week small group cohort that includes the support you need to really create the calm and effective work life you desire: 


  • On-demand access to Jess for asking questions and getting support.

  • Live, proven-to-be-effective workshops created for real people who juggle the modern stress of leading teams, managing projects, raising families, and navigating the millions of other obligations nipping at our heels on any given day.

  • LIVE SESSION - Design Your Personal Weekly Planning System: Customized For Your Personal Style & Flexible For When Things Shift: This workshop will support you, whether you like to get organized on paper or digitally, to put in place a proven weekly and daily planning process that works for you in your specific role and organization, including how to prioritize spending your time on the highest-leverage tasks and what to do when you inevitably must adjust because something changes mid-week.

  • LIVE SESSION - Managing Up, Down & Sideways: Your Project Leadership Toolkit: You'll leave with clarity on where your project management practices are strong and where you can take them to the next level. We'll have work time built in to plan next steps for a project you're managing right now or about to kick off. We'll dive into practical and research-based strategies for managing a team at work, managing up to your boss, and managing laterally to external and internal colleagues to accomplish your most important work. We will dive into the best practices of decision-making for individuals and for groups, including frameworks you will be able to use right away at work and at home.

  • LIVE SESSION - Build Your Anti-Procrastination Toolkit & Tweak Your Work Systems to Make Every Day Easier: Taking time to get your work systems freshened up is critical to being able to get "in flow" at work. We'll discuss the most impactful things to get polished and create accountability and space together to ensure that they actually happen. We will talk about practical strategies for how to conquer procrastination and get out from under the guilt of putting things off.

  • LIVE SESSION - The Energy Optimization System: Perform at Your Best Without Burning Out. Taking time to replenish energy is key to performing at our best. You'll get a chance to assess their current energy levels in different aspects of life, create a plan for how to rejuvenate themselves regularly, and learn what the research says to help us take care of ourselves because we deserve it and because it helps us do more impactful work.

  • Weekly resources like printables, templates, and checklists for each of our 4 weeks.

  • Unlimited access to asking Jess questions via email and in our live sessions. In the past we've covered all sorts of topics that participants need like prioritization, procrastination, browser tabs organizing, running meetings, productivity apps, getting too much mail at your house, how to setup standard operating procedures for your team, the best books to read as a team culture leader, and more. If it's related to work, go ahead and ask it!

  • Recordings of all live sessions to revisit if helpful, or review if you cannot join a live session.

  • An always-popular end-of-cohort Resource Roundup of all resources, links, advice, and session recordings for easy access when you need something in the future.

What do alumni of Joyfully Managed Worklife say?
This experience will support you to make the following true in your work life:

  • People start complimenting your impressive level of organization and productivity.

  • You’ll feel that lovely sense of “togetherness” that comes when you feel on top of what’s happening

  • Your team at work will notice how your systems and structures improve your ability to lead 

  • You will be able to actually clock out at 5pm while still getting the important work done

  • Your email inbox, no longer a nightmare, with just 7 (or 27) emails that need your attention instead of hundreds or thousands

Hi, I’m Jess. I’ve been a classroom teacher, middle-manager, and a nonprofit Executive Director. I’m a mom of two. I’ve gotten to the point of being fully burnt out at work and needing to find a better way. I’ve coached hundreds of senior leaders and new leaders with different styles and approaches on how to get more organized at work. The feedback I’ve gotten is that their stress levels and effectiveness have significantly improved by using the strategies we have worked together to implement in their work lives.

Frequently Asked Questions

What are the dates? When are the live sessions? 

  •  The cohort will happen in January 2026.

  • The live sessions will be on Wednesday at 11 am PT/12 pm ET for 90 minutes each, which includes about 60-70 minutes of live teaching with mini-work blocks included, followed by optional Q&A time and "get things done" at the end of the session to begin implementing your learning (a new addition based on past cohort feedback!). In case a complete list is easier to check your calendar for them (it is for me!), here you go:

    • Wednesday, January 7th at 11am PT/2pm ET/7pm GMT
    • Wednesday, January 14th at 11am PT/2pm ET/7pm GMT
    • Wednesday, January 21st at 11am PT/2pm ET/7pm GMT
    • Wednesday, January 28th at 11am PT/2pm ET/7pm GMT

    • The sessions will be recorded for anyone unable to join live, so there's no stress if you're unable to attend a few of the sessions live or if you like to review the material again in the future. The recordings include audio and video options, allowing you to listen in a podcast-style format.

I don’t have time to participate in this - I’m already too busy!

  • I hear you. I know the Catch-22 well of wanting to find ways to make things less stressful and chaotic while not feeling capable of finding the energy and time to actually make those changes. In my experience, the support and accountability of joining a live experience is the one way that I’ve found to make changes in my life when I was struggling to prioritize those changes. 

 I've tried other organizational programs before, and they didn't work for me.

  • I’m not going to prescribe that you work in a particular way. I don’t think it’s effective to tell folks they should be using this particular task management system or notebook or planner or anything specific. Our brains all work differently. What is true is that there are some high-level frameworks, best practices, and approaches that have worked for hundreds of people who I’ve coached or supported in workshops. And I believe that they can work for you too. We’ll have lots of space for you to ask questions and design approaches that fit your role, your context, and your style.


I prefer to figure things out on my own rather than relying on a structured program.

  • I get it. I’m often in the same camp. And can I lovingly ask – how’s that going for you? I think the support of a group of others who are working on the same things - who GET it - is likely to feel really helpful for you and ensure you get much better results than going it on your own.


I can find plenty of free resources and tips online. Why should I pay for a live group experience?

  • You certainly can google some of these topics, and I bet you’ll get some tips! The magic is in the accountability to put them to work, tweak them to make them work for you, and do it in a strategic order that makes the most sense for how our brains work. I’ve worked with hundreds of folks and have learned a lot about what helps these practices actually stick, and I’d love to get you out of the search engine rabbit hole and into a better use of your time that actually works. 


I have a question that's not answered here, or I'd just like to chat with you first before deciding about whether to join!

 Who is this Jessica person running the course?

I’m based in the SF Bay Area (Brentwood to be specific), and I moved here in 2023 after living in Oakland, CA the last 20 years. I have two kids (ages 9 and 11). I started my career as a classroom teacher, began leading teacher professional development, and then was a co-founder to a nonprofit education advocacy organization where I led for 10+ years. Since 2021, I lead workshops and retreats for teams and create online resources to help folks get organized at work and home. 

Want to bring your team? Let's make it happen.

Small Team Discount (3-4 colleagues): When colleagues learn together, magic happens. You'll have built-in accountability partners, shared language for your new systems, and the ability to support each other's implementation back at work. If you're bringing 3-4 team members to the public cohort, you'll each receive a 25% discount (bringing the cost down to $745 per person). You'll benefit from diverse perspectives from other organizations while still having your own mini-support squad. 

Email support@jessicaeastmanstewart.com for your team's private discount code or to arrange invoicing.

Private Custom Cohort (5+ team members): Ready to transform how your entire team works? A private cohort might be your best investment.


With a custom experience, I'll: 
  • Teach with your actual tools and systems (Asana? Monday? OneNote? Slack? Notion? We'll work with what you use.) 
  • Address your specific pain points through customized scenarios and examples 
  • Create a shared team language around productivity and systems 
  • Schedule sessions around your team's calendar and key deadlines 
  • Include your organization's actual projects as workshop examples 
  • Provide team-specific templates that match your workflows

    This isn't just training—it's a team transformation experience that creates lasting change in how you collaborate.

    Private Cohort Investment: 
  • 5 team members: $4,985 base rate ($997 per person)
  • Additional participants 6-15: +$797 each
  • Additional participants 16-25: +$697 each
  • Additional participants 26+: +$597 each

    Example: A team of 12 would invest $10,564 total (significantly less than most single-day corporate training programs, with 4 weeks of transformation).

    Interested? Let's talk about your team's specific needs. Email jessica@jessicaeastmanstewart.com or grab time on my calendar now to explore if this is the right fit at https://calendly.com/jessicaeastmanstewart/discuss-working-together.

This powerful program is just $1,497  $997! 

I know that money is tight for individuals and organizations, so I've used the feedback from my first handful of cohorts and dozens of participants to prioritize the most important content and aspects of the program, making it even more affordable for participants—just $997 for this 4-week program.


To put that in perspective, a typical 2-3 day conference can easily run you $2,500 once you factor in registration, flights, hotel, and food. And all you leave with is a tote bag (you don't need another tote bag, my friend) and some notes you will not have time to review when you come back to your post-travel to-do list.


This program is actionable and designed to create momentum from the very first session.

*Bonus Gifts*

All Joyfully Managed Worklife students will immediately get 3 of my most popular courses for FREE (normally $37 each)! No need to wait until January to get the transformation going and the stress reduced.

Complete Gmail Cleanup Toolkit Course (including Outlook modules!)

 Polish Week Course 

 Plan Your Week Course

Payment Options:

  • You can pay online here on this page in full.
  • You can pay in installments using Klarna, Affirm, or Afterpay. 
  • Jessica can submit an invoice to your company or organization.

Add-on Offer: add 2 individual coaching sessions for an additional $497. 


Jess no longer offers 1:1 coaching, so this add-on to the Joyfully Managed Worklife experience is the only way to accept this support.

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    Joyfully Managed Worklife January 2026 Cohort (Pay Now)$997.00
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    Joyfully Managed Worklife January 2026 Cohort + Private Coaching (Send Me an Invoice)$0.00

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Add on 2 private coaching sessions with Jess for $497.

Jess no longer offers 1:1 private coaching except for as an add-on to the Joyfully Managed Worklife program cohort.


During your 2 one-hour sessions (that can be scheduled anytime during the 2026 year, so use them when you need them!), we can discuss any individual or team challenge that would support you and Jess will ask questions, share practical tips and resources. Sometimes we even screen share to really get into the nitty-gritty to get you unstuck. 


You can even bring a colleague or two if talking as a group would be helpful for you!

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  • 1xJoyfully Managed Worklife$0
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All prices in USD