Navigating Work Transitions

Are you ready for a change?

I help people navigate large life changes. Change is hard. But with a clear plan and accountability, you can accomplish it. 


Make more progress with your money

Become an entrepreneur or self employed doing the work you love and are good at!

Transition into early retirement, semi retirement or a mini-retirement

Which Coaching is Right for You? 

Money Coaching

Let’s create a clear financial plan! Understand your: Income, Budget, Debt Paydown, Investments, Saving Goals, and make progress towards Financial Independence.

Work Transitions

Transition to semi-retired, early retired or take a mini-retirement. Maybe you are ready for a break after facing burn out, fatigue, or boredom in your career. Let’s create a financial and career plan to make that happen.


Ready to start a new business you’re passionate about or create the systems to scale your brand online? Over the last five years, I’ve been in the online space, helping people build a brand and presence online or create digital offers, like email opt-ins and online courses, to help expand their brand, service, or revenue. 

 Is Mentoring Right For Me?

Who do you normally mentor?

People who are ready to make a change!

They have a few traits in common.

1. They are ready to do difficult and honest work.

They don’t just show up to chit chat. They want to see a lot of personal growth, create a clear fiancnail plan, navigate a transition into a new career or FIRE, or build a life they would never retire from.

2. They are open to feedback, clarity, and direction.

They are willing to try things, even if it’s uncomfortable.

3. They think the quality and impact of their life matters.

Their personal and professional growth matters. How aligned their lifestyle and work is to their purpose and values has merit. So while many are frugal, they aren’t cheap when it comes to living their best life.

Is this like Life Coaching? Business Coaching? Financial Coaching?

I’m a progress coach. We will look at your big life vision and then pick 1-2 areas to focus on making massive progress. 

The process looks like this:

1. Clarifying your goals and what you want your life to look like.

2. Figuring out the true motivations and challenges for those goals.

3. Looking at all your financial numbers that are applicable.

3. Creating a kick-butt plan to pull that off!

4. Finding the 5 things you have to do NOW from the 100 things you SHOULD be doing.

5. Problem-solving, accountability, encouragement, honest feedback, and expert advice.

I work in a loose framework but focus entirely on where you want to go in the next few years and what you need to do to make that happen.

The end result looks very different for each person depending on where they are going and what they need.

Some calls feel like straight business coaching, creative coaching, mentoring, life coaching, or a heartfelt and hard talk with your BFF. Sometimes I hold space (if you are close to figuring it out). Sometimes I give really clear, step by step, get this stuff done advice.

Is it a good value for me?

Does this sound like you?

 You’re ready to make a change.

1. With your money. You want to make more progress financially! Have a clear financial plan in place understanding your: Income, Budget, Debt Paydown, Investments, Saving Goals, and Financial Independence. I’ve spent 15+ years studying this, teaching it, and practicing it in my own life. Which is how I became financially independent at 32. I can help craft a simple and straightforward plan to help you make progress. 

2. Transition to semi-retired, early retired or take a mini-retirement. Maybe you are ready for a break after facing burn out, fatigue, or boredom in your career. I took four mini-retirements before retiring early at 32. They can be a powerful reset to help you refocus on the direction of your work and life and come back refreshed. 

3. Start a new business your passionate about or create the systems to scale your brand online. I started my career in small business and understood the struggles and overwhelm that can bring. Over the last five years, I’ve been in the online space, helping people build a brand and presence online and create digital offers, like email opt-ins and online courses, to help expand their brand, service, or revenue. 

If that sounds like you and you have felt a little stuck, overwhelmed, or frustrated, mentoring might be an excellent value for you!

Investing in mentoring is about 75% less of what the average financial adviser charges! Plus, I have experience helping nearly 100 people who have some financial freedom use that freedom to make significant and unique changes in their lives.

*If you are self-employed or a business owner, you might be able to claim the mentoring cost as a deduction. I provide invoices on request.

Who is mentoring NOT right for?

That’s actually a much longer list than who it IS right for.

While I think everyone could use a mentor, I DON’T think everyone should apply with me or right now.

Who shouldn’t apply:

1. You don’t really want to change….anything.

2. You don’t have the time or energy to invest in yourself. (Even a few hours a week.)

3. You’re cheap. You honestly don’t think improving your life and work has any value.

4. You are a grump. Mentoring is a very close working relationship. We will be spending HOURS together. If your a grumpy, negative, complain about everything kind of person, it won’t be fun for either of us.

5. You’re not ready. Some people simply aren’t ready to see growth. They are scared, angry, bitter, ambivalent, or hopeless. A little scared is fine. We are all a little scared. But you have to bring the hope, optimism, and motivation.

How It Works

Getting Started

Your first step is to apply for a spot. I only work with people who are a great fit. I’ll review your application and make a suggestion. If it’s not a great fit, I’ll suggest other options. 


Create Your Coaching Plan

We look at all your long-term goals and values then create a comprehensive step by step plan.

Clarity, helpful perspective and accountability combined with homework and action items.

Reach Your Goals

After we create a full plan, we will check in twice monthly to address challenges and find the next high leverage steps you need to take.

4 Month Mentoring Package

Amazing things can happen when we have accountability and a clear plan!

What our work will look like:

  • Two  55 minute 1-on-1 calls a month for 4 months
  • Custom videos and worksheets to make our calls even more productive
  • Email support
  • Full custom, actionable plan for your next 12 months

Optional supports (included in price)

  • Weekly review emails that I will give feedback on
  • Two-week daily accountability jump-start
  • Pairing with another coaching client as a “buddy” to go through the program

You’ll need about 1-2 hours a week between homework, calls and email communication.

While we look at things across your life, we will focus on one or two areas of focus.

  • Work Transition: going part-time, taking time off, retiring, switching roles, changing careers or making work more enjoyable.
  • Building your Business: getting started or growing into the next level by creating a stronger online presence or building digital assets.
  • Financial Plan: Have a clear financial plan in place, understanding your: Income, Budget, Debt Pay down, Investments, Saving Goals, and Financial Independence.

If you are ready for some change, I’d love to help you get there!



Kat’s Story:

I had been planning my escape from full-time bureaucratic work for more than eight years.  My dream had been to leave full time (meaningless, awful) government work and instead do jobs I loved; fun, meaningful and useful work that was also flexible and part-time. But despite paying off all debt and having money saved, I knew there was a very large chance I wouldn’t pull the trigger, out of fear of trading a known income for an unknown or much lesser one.

That first call, I remember feeling really afraid of failure… what if I left my good (but depressingly meaningless) job to try ‘fun jobs’ and found that they were awful too? Or that I couldn’t make a living?  What if I languished?
You (Jillian)said, “You clearly have always been a highly productive contributor, and you will continue to be.  You will be fine, you just have to step into it before you can see PAST the fear in front of you (blocking your view) into the benefits of the new life.”  I felt both ‘heard’, and yet reassured at the same time. I couldn’t believe in myself at that point, but I could believe that YOU might be right about things, and that was enough to take action at first.

As of this writing, I am leaving my job at the end of next week. I already have two part-time jobs (and one starting in September), all of which I LOVE! One professional work for a non-profit I had been volunteering with, the other two being fun flexible meaningful jobs on my ’50’s bucket list’.

I would never have gotten here on my own, certainly not for many years more.  I am excited and grateful and stunned and happy all at once!

It was the best money I have ever spent in my life. Mentorship was PERFECT for me, someone who is very fiscally responsible yet RISK averse.

Christine’s Story:

I had just committed to moving my family out of California and leaving my job. Jillian’s mentoring course seemed like the perfect opportunity to help me with this huge transition. I knew that having scheduled meetings and a coach giving me homework would help me carve out time to focus on myself. I wasn’t sure if I wanted to get another 9-5 job or start my own business and I was seeking clarity.
I also wanted to work with someone who truly understands what it means to be “Financially Independent” in order to continue on my path toward FI.
The mentoring process has included several one-hour calls with Jillian, doing homework in the form of watching video lessons and completing worksheets, and doing the action steps that Jillian has helped me to identify in order to clarify and reach my goals. Jillian’s comments and questions have been very effective to help me manage my own anxiety and discomfort about trying to start a new business.
The mentoring process is great for anyone who is willing to spend time thinking, planning, and most importantly, taking action steps to progress toward their life goals. Personally, I think it’s a great value to work with someone who is so smart, organized, empathic, kind and driven. Thank you Jillian!!!

Rachel’s Story:

I wanted to design a life where income was passion and passive based and where I could work as a solopreneur in my business doing what I love. I wanted someone to give guidance where I needed it, and to provide accountability.

I’m excited about this new phase of my business. I have made far more progress than I could have on my own, and the next 5 years are far different to what I imagined when we began mentoring.

This is for highly motivated people who are ready to put in the time and effort required to make progress.

Monty’s Story:

I run Sportivecyclist.com a site about road bikes. When I read Jillian was going to be opening up a limited number of spots, I jumped at the chance. I’ve had the blog for 5 years but between working full time and three kids, I’ve been struggling to find the time and focus.

I signed on with Jillian to try to build and launch a product and really bring that focus. And really try something new. I’d heard about coaching in the buisness and sporting sense. I was interested to see how it would work in the context of me and my blog.

Over the course of 12 weeks, we came up with an idea (via market research, surveys, and reader feedback), developed a product and launched it. It brought in $1500 and showed that I could get tangible results and income from something I built.

I definitely recommend you sign on with Jillian if you get a chance. Working with a coach who is so attuned to building audiences and focused on getting results to move the process forward.

When you have a limited amount of time, you really need someone to hold your hand to the fire and make sure you are delivering.

Brice’s Story:

I knew I was in a good spot to make a lot of progress on in my personal finances, but even after a few years with a great paying job I still had $60,000 in debt. I knew I didn’t want to stay stuck in debt with no form of traction to get out of the mess I had created. I just needed a better plan, some accountability and encouragement.

After the first 3 months of mentoring, I paid off $18,000 in student loans! I will be debt free by the end of the year! (Brice Update: He paid off $60,000 in debt and is aggressively saving now!)

I’m on an entirely different path now and am really excited to see what the next few years bring. Working with Jillian, I was able to get really clear on where I want to go and what steps I need to take to get there. (Brice Update: We are now working on building Passion Income to transition careers!) 

Jenny’s Story:

I signed up because I’d really been struggling with work. I wasn’t sure if it was time for a new job, or if I just needed to be doing (or thinking through) things differently at my current job. I’d been trying different strategies both at work and with the rest of my life to create more balance but I still felt very stuck.

Jillian’s exercises helped me clarify my goals, motivations, and challenges, and I think the most helpful part has been talking through the exercises with her. Some things are clearer to an outsider, and I really don’t think I would have gotten to certain breakthroughs if Jillian hadn’t pointed me there. What’s really surprised me is that I decided to work with Jillian specifically to work on my career, but I’ve actually made progress in several other areas of my life too!

I was inspired by Jillian’s post about ‘becoming your best boss ever‘ to set aside money to invest in my professional development, and I think this was the best possible way I could have allocated those funds!
I honestly can’t believe how much progress I’ve made in these past three months. Working through the exercises gave me clarity on where I want to be and what I want to achieve, and then talking with Jillian and learning about different tools and how to use them has helped me move forward even when I hit a barrier. 

Ann’s Story:

Since the beginning of 2017 I’ve been trying to create a side business and have been considering a career change. I found myself getting stressed out and overwhelmed trying to become more productive in my life which was slowing down my forward progress.

I’ve always been into DIY (Do It Yourself) everything. Although DIY is a good strategy, most of the time, if you are trying to make a significant/meaningful change in your life, it can be so beneficial to get outside help.

Jillian is such an encouraging and supportive mentor. She really has a knack for breaking down huge goals into manageable tasks and brainstorming ways to overcome challenges. Her insight and long-term focus have helped me to see that I was suffering from some self-limiting beliefs and that I was operating only in my comfort zone.