Career Break

Group Coaching

Next Session Starts May 20th!




Are you Ready for a Career Break?


This group coaching is for people who are looking to step away from their 9-5 for a month or longer, maybe even forever. If you are considering taking a career break this year, group coaching will help you navigate that transition more effectively and make the most of your time off.

3 Components of Group Coaching


With a proven framework, deep dive coaching and a mastermind, your mini-retirement will be more meaningful and impactful.

#1 Workbook

 You’ll receive a digital and printed 90 page workbook to guide you through the logistical framework, big ideas, and best practices of taking a mini-retirement. It contains every worksheet you need to master the 4 steps to a career break. 


#2 Live Coaching

Jillian leads recorded coaching calls and a Facebook group that will deep dive into the groups’ specific concerns. This is where we take the ideas from the workbook and go deeper, making sure you master the concepts in the workbook. Live Q&As, and group discussions will help address any concerns. 

#3 Cohort

You will be a part of a Master Mind Cohort. During cohort calls and in your private chat you can share your individual goals, offer feedback, and help brainstorm as a small group. Each Cohort of 5-10 people will be paired based on goals and challenges. Finally you will have a group that understands why you’re doing this and can support you. 

Is Group Coaching Right for me?

Group Coaching


While a career break is nice, some people get 50% of the benefit they could, but with some planning and guidance, you could take full advantage of your sabbatical. Giving up income for a month or a year is an enormous cost; it’s worth the time, effort, and investment to get the most from your career break.

Is now the right time?

Knowing the perfect time to take a mini-retirement can be challenging. In group coaching, you’ll figure out when the right time is and what you need to do to get ready for your career break. 

THinking about switching Careers?

Many people wonder if there is a better career option out there for them. Maybe you can’t imagine doing the same work, the same way for the next 30 years? Group coaching will give you a frame work for how to explore other professional options.

Stuck in One More Year Syndrome

There is always a logical reason to postpone leaving your job. Group coaching will help you problem solve challenges and feel more confidant to make the leap.

Sign up starts May 1st 

Get Started

Retire Often Group Coaching

Introductory Pricing



10 Week Program

Digital and Print Workbook

Video Course

Live Coaching

5 Group Teaching Calls

Ask Questions In 10 Facebook Live Sessions

1-on-1 plan review with Jillian *As an add-on for $150

Mastermind Cohort

5 Cohort Mastermind Sessions + What’s App Chat

Sign up for a 15 introductory call to join the May 20th Retire Often Group Coaching Cohort


Frequently Asked Questions

What times will the calls be?

Scheduling is always the most challenging part!

Our 6 group teaching times will vary a bit, but mostly weeknight evenings. Each of the group teaching calls will be recorded.

The 12 Facebook 10 questions and answers calls will be on weekday mornings. One each week.

Your 6 cohort mastermind calls will be at a time that works best for everyone in your group. The cohort and teaching calls will alternate weeks.

Can my partner join me?

Yes! You can join as individuals or you can join as a couple. As a couple, you will share a spot in your cohort. This means both of you will share your mastermind time. If you want more individual feedback and participation, you can join as individuals. 

Getting Started 

is as Easy as 1, 2, 3…

Book A 15 miniute Assesment Call

Book a time to chat with me and see if the group coaching is the right fit for you.



Access the workbook

You will be receive access to the workbook immediately to start when it’s convenient for you. 

Get ready to Start

We start the 12-week group coaching. You can then join the Facebook group and will be assigned to your cohort.