I’ve served as a mentor for 10+ years now, paid and volunteer. It’s something I’m really passionate about because I’ve seen the changes that can happen when someone “shows up” in your life. Knowing your goals, knowing your dreams, knowing all the facts about your situation, and can help you craft a plan. Then they encourage, brainstorm, troubleshoot, and offer a bit of advice along your journey to keep you moving forward.

I wanted to create a new series to help you DIY your own money mentoring process with these Peer Mentoring Tools.

Beings I can only personally work with 5 people at a time (6 if I buckle down and hire someone to help with housecleaning! See inspiration from the first book in our Summer Reading Party!),

So find a friend, spouse, partner, sibling, or coworkers who you can work through these questions with with.

It all starts with good questions. Most great mentors are great because 1. They “show up” in a meaningful way (focused on your goals, your situation, to help encourage you to make progress). 2. They ask good questions that help you figure out your own answers.

I have a very specific process I use for creating actionable, trajectory changing plans…..but it all starts with finding the answers to the most important questions. Because how will we know which path to take if we aren’t clear on the destination we want to arrive at?

The goal of this series is to help with the good questions.

You find the person to “show up” and I’ll help with the questions.

This first question in my money mentoring series is one Mr. Montana and I first tested out 2 years ago.  We did a money-life reflection weekend  2 years ago and asked this question. 3 months later we decided to leave the 9-5! But our answers have stuck with us, and influenced our spending/saving habits since then.

Mentoring Question: What would make you “feel rich”?

We worked though about 7 questions during that retreat, but over the last 2 years we come back to this one over and over.

It’s very possible to be rich in net worth, and rich in income BUT not feel rich at all.

Instead of feeling rich you feel like your are scrapping by. And it’s also possible to have modest net worth, and modest income and feel filthy sinking rich! It takes a bit of thoughtfulness and intention to make sure you end up with a life that feels rich in substance and not just numbers.

There aren’t really right or wrong answers. But as an example here are a few things that Mr. Mt and I each put down 2 years ago, why we did, and how we used that conversation to help shape our life now. Sometimes I find in mentoring, if I go first on a question, it gives context and a framework for others to figure out their answers.

How we answered this question

Ms. Montana: Having time to take trips or do fun activities

Being able to take a week away or go out and do fun things on the weekends feels rich. I don’t care what my net worth is, or how much income I make: if I have to work 12-14 hours a day, it feels like poverty to me. Poor people need to work 12+ hours a day. Poor people can never afford to take a week off. Or do fun things on the weekend. No matter what the numbers say, that will make me feel poor. If I have a 3 million net worth and earn 300k a year, it won’t change that fact. Being able to take a week off just makes me “feel rich”.

Updated this year: Being able to take a week off each quarter to plan, think and read

This is ultimate luxury in my mind. Like reserved for the crazy rich and privileged folks of the world. In Essentialism (Part of our Summer Reading Party!) I read about how Bill Gates takes a “think week” twice a year to read and think. How many people get to do that!?! Even among the CEO millionaire crowd?! A lot of very wealthy, successful people have build a house of cards that will collapse without the glue that is them.

Well, after our year off, I’m sold on the value!

So much so that I have started taking a “think, read, plan” week each quarter. I can’t image anything making me feel more rich than that. For me, that feels like the ultimate luxury.

Today the weather was amazing. I was following up on some emails at the coffee shop. So you know what I did? I shut my laptop and went for a hike with my husband and baby. And it was AMAZING. After years of feeling like I was stuck inside on those rare extra beautiful spring days, I couldn’t have felt any richer if I had a million dollars in gold coins filling my bedroom closet.

If you don’t know what makes you feel rich, you might build a life that always feels like poverty.

Mr. Montana: Having the right tools for the job

Apparently expensive sunglasses, eating at nice restaurants, or a good cigar found no place on his list, but this did. He HATES trying to “make do” with the wrong tool. If he needs a certain tool, being able to go buy it feels like pure luxury to him. It makes the work easy and enjoyable.

This is easy enough to accommodate. After I found that out, I don’t bug him about buying a $20 wrench to get some strange sized bolt loose. We might spend an extra $200 a year on tools. And he feels rich. (Although I prefer he rents bigger tools just so we don’t have to store them.)

We took about an hour and each came up with about 5 things. 5 things that are high impact for us.

The Magic in this Question:

If we know what few things truly add richness to our lives, we can stop wasting money on the stuff that doesn’t. We channel our time/money to high impact things, which provide the most bang for our “feel rich” buck. Then we aren’t trying to fill a hole with low impact stuff. We will end up spending far less overall and feel like our life has a richness to it.

Road Block to watch out for:

With each good question, there is often a road block or challenge that trips us up. Here is one that I see happen this this question:

The thing that would make us “feel rich” is the thing that people most often avoid.

Because it just seems too good, or too self indulgent. We would rather “be more reasonable” and spend our money away on that smaller connivance. This sounds nuts. But I see it ALL. THE. TIME.

Here’s how to spot it:

(This a real conversation from my last 9-5 job)

Me: I am going to hire a house cleaner because between both the hubby and I working full time jobs, and constant renovations, we just don’t have the time. Plus it’s just SO nice to home to a clean house!

Them: Must be nice. (with a hint of jealousy and resentment) Yeah, I would love to do that. But I need to be responsible and clean my own house. You know, most of us have to clean our own homes.

Me (thinking): You buy take out lunch every day. And have a $150 cell phone bill.  I pay $100 a month for a house cleaner. If you wanted to skip just one of those or go with a cheaper option, you could have a house keeper too. Is your data plan and take out really making you “feel rich”?

But the lunch and data plans seem “reasonable and responsible” and living this “feel rich” life feels extravagant. And no joke some people will try to shame you for anything that seems to extravagant to them. It wasn’t the cost, but the self indulgent luxury of coming home to a house I didn’t clean that rubbed some people the wrong way.

Sometimes we will get that push back from others, and sometimes from that little voice in our own head. Either way, it’s something to watch out for. Because spending a little bit of money on high impact categories can greatly increase the quality of our life, while lowering our overall spending.


How to DIY this money mentoring question:

  1. Find a person to do each of these questions with (friend, sibling, spouse, coworker). Someone who is emotionally intelligent, supportive and encouraging. Someone who asks good follow up questions and makes you expound each idea. A great mentor isn’t often the “expert” that will talk at you for an hour. (If you want solid advice from experts, read their books.) A great mentor is 80%: curious, intuitive, a question asker, emotionally available, and invested in your progress THEN 20% “expert”.
  2. Brainstorm you initial list. Talk about why that would be. And how you could find small ways to start moving in that direction. Take at least an hour.
  3.  Write it down somewhere.

Often the things that make us feel rich aren’t so far out of reach. Some we can find a way to fit into our budget and schedule this year. And if we keep them in mind, over the next 5-10 years we can steer our life in a direction that more and more closely matches our list.

Follow up questions:

Often our truest answers are a few questions deep. We need mentors to help us dig and get at the core of the issue. So follow up questions are key. Here are a few

  1. What about that specific would cause you to “feel rich”.
  2. What would that provide or offer? Is there another way to replicate that with a smaller cost or scale?
  3. What would that mean to you? Or represent?


You can check out more of my mentoring process HERE.

Good luck as you DIY this with people in your life! And if you aren’t sold yet, check out my post on the benefits of mentoring and 3 qualities you should look for in a mentor.


For Conversation:

So what makes you “feel rich”?

Do you ever feel bad for those things that really feel like luxury, even if the actual price tag is reasonable?

How have you made small shift to things that give you the biggest bang for your “feel rich” buck?