Money Mentoring DIY Question: What makes you “feel rich”?

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.

How to do money mentoring with a friend

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. (read my mentoring page to get a better idea of all the steps!)

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?



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19 thoughts on “Money Mentoring DIY Question: What makes you “feel rich”?

  1. Jillian, what a great question to kick things off in your mentoring series. “Rich” is an interesting word, and taking time to THINK about the concept ironically leads to the non-financial areas of our lives. I love that you’re targeting once/quarter for your “think days”, and agree with you that “having time” is a great measure of richness. Knowing our time on earth is limited only heightens the urgency on finding ways to make time for the things that really matter in life. It’s the primary reason I’m retiring early (June 2018). Thanks for the brain food today!

    • Most of the things that made our “rich” list were only vaguely related to income/net worth/spending. =) Usually even if it does seem money related, there is a deeper cause. Like one on our list was having a relaxing backyard to drink tea in during the summer mornings. Because what we really crave is that quite relaxing time to connect and enjoy nature.

      Having time is huge! But I notice that a lot of people who are actually very rich still lack the free, relaxed time. It would be really, really easy for me to book those weeks up with other “work” things. It takes a lot of discipline for me to create that margin, but if that is really what gives my life that sense of richness, I need to be intentional about it!

  2. I love the ‘What would make you feel rich question?’. It really makes you consider what you actually need to accomplish instead of setting a monetary goal. For me, it would be a time thing. Right now my finances feel comfortable but I don’t necessarily have the time to do all the things I want to go. That goes full circle though, because at this point, having more time would mean working less and not having enough money to do all those things anyways.
    I don’t have an official ‘retire early’ goal I’m going after but I would like to get to a place in my career where I have enough money coming in and the flexibility to cut back my hours. I enjoy working and don’t have the desire (at least no yet) to give that up but not having to come into the office 5 days a week would make life more enjoyable and make me feel richer.

    • I think that is right on the mark for most people! Just having an extra 20 hours a week of free time would add the “richness” in the other cool things they could be doing. Buying more stuff doesn’t often add that “rich” feeling if we are maxed out and tired. A 2 hour relaxed lunch break with good friends each day would add so much more richness for most people than a new dining room table. But a new table is easier. I think if we have our list of things that really add richness to our lives, we can be intentional to start making slow steady steps in that direction.

  3. 1. I love the concept of this series.
    2. I love this question.

    You are absolutely right that one of the biggest jobs of a mentor is asking the right questions. We all know what we want, we just need to be able to dig it out. A good mentor is someone that can help us dig within ourselves.

    Thanks for this! Looking forward to more!

    • Digging out the true answers is SO important! I spend a fair amount of time on questions before I launch into my mentoring plan with people. Partly because once I can get to the true core answer, when we face challenges or questions in the future, I go back to those. As in “remember when you said THIS was in your top 5 important things? This new choice doesn’t really fit into that bigger picture, does it?” When we get really clear on the big picture stuff, the little stuff gets easier.

  4. Hi Ms. Mont,

    I think that’s a great question, but thought the best part was in your observations about what trips people up with it. It’s very interesting how in some areas we feel almost a sort of need to deprive or almost torture ourselves, whereas we’re sometimes willing to splurge in areas that don’t really bring a whole lot of satisfaction.


  5. This is really great advice. I’ve been thinking of ways to help others with finding more balance, while making better money decisions. What a perfect question to start real conversations!

    My first response to the question is probably being able to take extended amounts of time off to go on adventures with the kids – pretty much the road trip we’re planning for 2022. If there was a way to move that up a couple of years, I would definitely feel rich.

    • Time for adventures is big for us too! Now that we have more freedom to set our scheudual, we have had to be very mindful to keep the margin for that to happen. We set aside time each weekend that we call “weekend adventure” and all the kids hold us to it. Especially with little kids, it can be easy to get caught in the never ending cycle of laundry, shopping, cleaning, errands and forget to make time for the things that really do add richness to our lives.

  6. Our weekday walks in the park make me feel rich. We go when we feel like it. Often it’s just us and the grounds crew, or sometimes a few young mothers are there with kids. On weekends it gets crowded with baseball activity. We still take our walks but we marvel at the fact that we used to have to cram our activities into weekends, too.

    It’s a great question to ask, Ms. M. Often people are looking to capture a state of mind in order to feel rich that has nothing to do with money.

    • You are spot on that it is often a state of mind. Often a sense of freedom or autonomy. Just the ability to decide something for themselves or set their own schedule. The funny thing is, unless people really dig to the root of the question, even if they do become their own boss they still don’t give themselves that thing they crave. It’s like the Walden Theory. Ask people how much income would make them feel rich and they say twice as much. Ask people who are making that amount if they feel rich and 95% will say “no”. People making 20k want to make 40k, people making 40k want to make 80k, people making 80k want to make 160k and this “feel rich” is elusive. I’ve seen people spend their entire life chasing down “more” and never finding “enough”.

  7. I love this question – though we’ve discussed it in a general way, I don’t think Alan and I have ever sat down and been intentional and specific about answering it. Now I know what we are doing this weekend! I believe when we’re living a life aligned with our priorities and values, that’s when we’re rich. But it’s so easy to get off track and forget how precious our limited time is. Thanks for the question and guidance! Can’t wait to tackle it this weekend!

    • Yeah! I think it’s so good to really dig into specific questions. One of the cool things is that after you go through 7-15 questions, the patterns get really clear. Life choices get easier because the vision for where we want to head is well defined by a host of good questions. We often circle back around to questions every few years, because life changes, and sometimes are answers have changed as well. Plus in marriage, the right question can frame the conversation is a positive productive light, where both people get heard. This is a funner question to start with than “what do we cut out of our budget.” =) I’m excited to hear how it goes!

  8. With the housekeeping discussion, you maybe save me a lot of discussion at home… thx for that! I will focus less on getting rid of this. We brown bag, we have no cell phone costs, we pay attention elsewhere.

    We did a similar exercise a year back in the plane: what would we do when money would not be an issue…! It helps to set priorities

    • There have been times the housekeeping made a lot of sense for us. Before when we both worked, it helped us do all the renos ourselves and build wealth that way. My coworkers thought the whole thing was crazy. Working late each night on rental properties, hiring someone to clean, just the whole situation. But now they are still working that same old job, and we have been able to walk away from that. =) Yeah, it just comes down to priorities and knowing your long term plan. =)

  9. For me, it’s money in the bank. I try not to overcomplicate things too much. 🙂
    Being able to splurge occasionally without screwing up our finance is a great thing too.

    • Having actual cash in the bank is a big one for me too! Like enough to cover almost any type of emergency. Although, a paid off house is also really comforting. I’m not sure that a big stock account would feel the same way. Especially during a recession. I think I would feel bad about selling stocks if they had dropped in value. I think it’s good to know what works for you. =)

  10. I love this post! What a wonderful question! I have a dear friend and I am going to ask her if she would like to join me in this exercise, maybe we could be each others mentors 🙂