Custom Mentoring Program

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You have an idea of how you want your life to look, but the vision isn’t crystal clear and you don’t really have a plan to get there. It’s more of a “maybe” or a hope for “someday.”  “Someday I hope to see Paris.” “Someday I hope we can to take a big trip with my family.” “Maybe, someday,  I’ll write a book or start a business.” But without a plan, “someday,” “hopes” and “maybe’s” rarely become reality.

Perhaps you have made a lot of progress in the last 10 years. But there are still big things you want to do. Scaling your life to achieve those big dreams seems intimidating. The status quo is ok. Maybe you should just stop here? Why dig deep to achieve those dreams that others might see as crazy? 

what to look for in a money mentor

It’s possible to come to the end of our journey on earth, and realize life has just passed us by. We kept our head above water. We made it through. But we didn’t really LIVE. We went with the flow and slowly let go of all those crazy things we thought about as kids. Seeing the world. Traveling. Building a company. Writing a book. Amazing experiences with family and friends.

But it’s crazy hard to do it alone. To make your vision become reality, you need someone who sees the bigger picture and will help you create a roadmap to get there.

That is what I offer as a mentor. I look at your big, long-term goals and dreams. We confront the challenges that have held you back and find solutions. I examine all the details of your current situation. Then we work together to plot out a plan, breaking big goals into small actionable steps and habits.

Each month we review progress and find the next step… so you stay on track. Small victories lead to bigger goals. And the bigger goals pave the path towards the life that fits your passions and purpose.

financial and blog mentors


I help you narrow down the next step you need to take out of a 100 good options.

My mentoring process incorporates 4 simple steps

1. I ask questions.

In our 1st call, we will go over your long-term goals and get an idea of the big picture. I will give you a few exercises to work on, uniquely engineered to match your specific situation. These exercises provide the framework for the first calls.

These exercises will uncover:

  • Your true values
  • Passion/calling
  • Potential challenges you could face
  • Limiting thought patterns
  • Ideal lifestyle
  • Type of impact you want to make
  • Most important long-term goals

2. We examine your current situation.

I believe your direction (trajectory) is far more significant than your current location. But we all start right where we are. So where are you right now? In our 2nd call, we will look at all of the metrics that matter to your long-term goals and gather any needed information:

  • Your financial situation (income, debt, monthly expenses, savings, passive income, etc.).
  • Your current skill set–and skills you want to expand
  • A project or side hustle you have begun that isn’t making the progress you want to see

During the 3rd call, we go over any challenges that you see to the goals you have. Without understanding the true challenges, they continue to create sticking points that hold you back. Once we understand the actual challenges we can find specific and extremely effective solutions. Then we dive into your motivations behind those goals. The more clearly we can describe the motivation, the more resilience you will have when new challenges arise (and they always do!)

3. We create Your Road Map.

So far we’ve looked at where you want to go, your current situation, then challenges/solutions/motivation. In our 4th call, we create your roadmap. This comprehensive plan outlines how you will get to your goals and dreams. We look at the big picture and find the benchmarks you need to hit each quarter. We identify what action steps and habits are needed to set your trajectory.

4. I provide ongoing monthly support.

Each month we will have a 90-minute call to find the action step and habit needed THIS month to hit your quarterly benchmarks.

  • What action items are needed THIS month?
  • What habit should you focus on next?
  • What new question do you need to consider?
  • What underlying challenges need to be brought into the light?


The magic of a mentor.

Magic happens when a mentor shows up in your life for the things that are most important to you. A mentor provides clarity, direction and encouragement.

In the last 15 years, I have paid off $50,000 of debt, traveled around the world, taken three career breaks/mini retirements, adopted 4 kids, paid cash for our first house, bought/renovated/managed  2 rental properties, failed and succeeded in businesses, grown our net worth to $650,000 and left the 9-5 at thirty-three years old. My successes have given me a lot of insight–but so have my failures.

I’m not an expert in everything. I am very good at seeing where people want to go, what exactly is holding them back and how to create more effective plans that will give true progress. I have an endless supply of pep talks and ass-kicking encouragement.

Each of our monthly mentoring calls will contain these 4 action points:

1. Reflect:

Are you progressing on your monthly action steps and monthly habit? What new things did you learn? What went well? What challenges arose?

2. Refocus:

Each week, month, and quarter we need to refocus based on the reflection we have done. Just like sailing on the open ocean, you must constantly refocus and adjust your direction. This is where we apply all the things gleaned from our reflection.

3. Brainstorm:

I ask questions. We test ideas. And occasionally I will throw an idea or a suggestion out there. Just enough guidance to smooth over a tricky spot in your journey.

4. Identify the Next Right Step:

We can be paralyzed by one hundred good options and tasks that all seem to need to happen RIGHT NOW. A good mentor will help narrow down the 100 things you COULD do to 3 things you really NEED to do. And let you pick which 1 comes next.


There is ENCOURAGEMENT and ACCOUNTABILITY when someone like that shows up to help you make progress on your biggest dreams and goals. 

Who is mentoring right for?

The people I mentor all start in very different places and want to go very different places. But they all have two things in common.

  • They believe that life can be different and better than it currently is.
  • They have the courage to take the first step.

Everything else I can help you with, but you have to bring those first two things.

If you don’t think things can ever change, I won’t be able to convince you. If you don’t have the courage to even fill out this form and do a free thirty-minute meet and greet, I won’t ever know you even read this far.

If we start working together, I can help sharpen your vision for what life could be. If we start working together, I can encourage and cheer you on as you take the journey step-by-step.

But the first step is all up to you. If you are ready to take that next step and start taking ground on your biggest dreams, I’m ready too! I would love to partner with you and help you customize your roadmap and provide monthly support. There is no need to waste any more years just treading water. Progress and change are possible!


The first month we will have four 90-minute calls and develop your custom road map. We will look at your long-term goals, current situation, challenges, and create an actionable plan to get you where you want to go!

The next 5 months we have a monthly 90-minute call to reflect on the progress, refocus, brainstorm and plan out your next steps.

You get 6 months to make significant progress on your goals for $995. Plus, I will give you access to any of my online materials and courses that you need at no additional cost. (Currently $269 value plus a new course coming soon!)

If you think mentoring might be the step you need to make the changes you want to see, fill out the form below. I’ll be in touch to set up a thirty-minute free Skype call to see if it’s a good fit.

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Here are a few things people I have worked with have had to say about the experience–and the RESULTS  they have seen!


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! I’m on an entirely different path now, and am really excited to see what the next few years brings. 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 B.


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, from snaking my own drains to learning how to invest my retirement accounts for myself.  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.

Ms. Montana 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 has helped me to see that I was suffering from some self-limiting beliefs and that I was operating only in my comfort zone.

Having a proper mentor is not the same as mentioning a few goals to a family member or friend. Ms. Montana goes into depth and thoroughly analyzes all of your life goals and money goals to come up with a holistic approach that is customized to you.

The last 3 months have been amazing!

-I’ve been more productive with my free time than I’ve ever been before.

-I’ve read more books and become so much more knowledgeable about finance and productivity.

-My food budget is the lowest it has ever been thanks to strategies from Ms. Montana.

-And I’ve been making progress on conquering fears and insecurities.

If you are looking for changes like those in your life than I highly recommend that you sign up for this program! I am so glad that I did!

-Anne E.


I’ve been a reader and a fellow blogger friend of Jillian’s. When I mentioned to her I was struggling with focus and have been feeling overwhelmed, she knew the content in her mentoring program could help. She sent me the types of exercises she was including in her program, compete with examples of how she uses them. Now, let me say this, I read a LOT of personal finance blogs. I write a personal finance blog! But this was a game changer!

While I’ve thought about the future, I have never actually plotted out 10 and 20 year goals. But with her encouragement and excitement, I got it done. This helped me set my 4 year goals and create my one year plan. My eyes were opened to the possibilities! Now I know exactly where I need to focus my energy and I am on track to reach my financial goals 3 years sooner than expected!

Knowing Jillian personally, she is passionate, encouraging, and loves helping people! After just the little bit of work I’ve done so far from her program, I got really excited about the future. It gave me the vision I needed and lowered my stress. THANK YOU!!! If you are able to have her walk you through each step, coach, encourage, and provide accountability throughout this process, it will change the trajectory of your personal finances.


You catch a vision for what your life can be. You make a plan. You set benchmarks. And day after day you make a step in that direction with habits that compound upon each other.

If you’re still not sure whether mentoring will be a good value, consider this question:

Where might you be if you had this kind of mentoring five to ten years ago?

Where would you be if someone “showed up” for you each month, someone who understood what your current situation was and what your biggest goals for the future were?

Where would you be if you had a mentor who offered clarity, direction, and encouragement to smooth the path and cheer you on?

Now, five or ten years later, how much more progress would you have made by now?

Is the difference between where you would have been with mentoring and where you are right now more significant than the cost of six months in this program? ($995)

If the answer is yes, fill out the form and let’s not waste any more time.

The next five to ten years is coming … either way. With or without the progress you are hoping for.

What will you choose?

If you want to see radical growth, all you need is 5-15 years, a plan and some encouragement as you learn this process. Often your results end up being even bigger than you imagined. Things start slow, but build momentum. 

I never would have been so bold to say at age 19 and $50k in debt, that “By 32 I want to be financially independent.” That would have been insane. But it happened. As I created this program for my own life, I saw more and more growth. And that growth compounded. Then all those good habits opened up even more doors.

I’ve come a long way. But you know what? The next 20 years are going to be even more impressive! I have so much more momentum. I have more experience in this process. I’ve lived the program.

All you might be missing is a mentor to come along side of you to get started. A trail guide. A money friend. An encourager. I’ll help you find the path that is right for you. I’ll teach you how to set up the benchmarks and create the habits of success.

With enough time and intention, your life can be radically different.




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2 thoughts on “Custom Mentoring Program

  1. Nice! We need more mentors out there. I think there’s a severe shortage. I mentor quite a bit myself, and am currently maxed out. It’s really fulfilling to help people; for me personally, especially the high school kids who are ambitious but unsure about their future.

    • I mentored high school kids for years! Loved it! Now it’s fun because most of them are in their 20’s, getting married, and starting families. It’s neat to watch how it all unfolds. =) I can only take about 5 people at a time, 10 tops. Partly because of time, but part is being very investing in their lives and progress. I only have so much bandwidth. =)