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

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). And 2. They ask good questions that enable you to dig 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.

This second question in my money mentoring series is one I asked myself about 4 years ago and then forgot about. I wrote the answers down… somewhere, mentioned it to Mr. Montana and didn’t really think about it again. But as choices presented themselves over the years, I made choices that brought me closer to the ideas I had sketched out. Now we are almost 100% spot on with what I had spent time figuring out 4 years ago!

Mentoring Question:

What would be your Ideal Day/Week/Year?

If you had enough passive income to cover all your basic expenses, how would you structure your day? What would the schedule for your week look like? Or more broadly, what might a year contain?

It’s very possible to create financial freedom but not know how to use your freedom to create purpose, happiness and meaning in your daily life.

Would you exercise every day? Eat a relaxed dinner each night with your family? Volunteer for 8 hours a week? Work on meaningful, challenging and exciting projects for 3-4 hours a day? Spend an hour outside every day? Surf or ski once a week? Travel for 4 weeks a year?

There aren’t right or wrong answers. But as an example, here is what I have been working on lately with this question. It’s something I have given serious thought to in the last 2 months. 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

how to write out an ideal day plan



The Magic in this Question:

Better choices NOW

There are things that we can do TODAY, and THIS week to move our day closer to our ideal. Maybe that means going the gym instead of staying up late watching Netflix. Maybe that is calling an old friend on the phone for 30 minutes instead of scrolling Facebook. We can practice by taking steps in the small areas.

When bigger choices present themselves, and we have carefully thought through our big picture ideal, then we can make the choice that more closely lines up with the things we have written down.

Does this purchase bring me closer or further away? Would this new job offer bring me closer to my ideal day or year?

I come back to this over and over in the mentoring. Once we figure out the answers to 4 or 5 good questions, all other choices are filtered through these. All other choices become much more clear.

It’s not me telling people the “right” thing they should do.

Instead we hold the new options up against their long term goals, ideal day, 5 most important areas, what makes them feel rich, etc., and see if the choice lines up. By doing this work upfront, you will have a reliable filter not overly influenced by the details of an current situation.

Do we really want what we thought we wanted?

Often, after careful thought, we can break down large vague statements like, “I would love to retire early!” or “I just want to travel!” Maybe you would actually enjoy working on a big project 1 or 2 months a year. Or working 3 hours a day. Or traveling for a year straight, then 6 months a year.

This radically changes the dynamics of your plan! You might be able to leave a 9-5 job YEARS earlier. IF you do the mental work now to figure out what you really want your schedule to look like, and start taking the needed steps now to move in that direction.

Road Blocks to watch out for:

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

Burn Out

We can be extremely burned out from our jobs or even our life. There are 3 main kinds of burn out that will skew your answers.

1. You are burned out from you job. So anything NOT your job sounds amazing. And the idea that any work could be meaningful or enjoyable seems a total farce.

2. You are so far BEHIND on everything. Your to-do list is crazy long, like a year’s worth of stuff long. Just getting back-to-even on sleep, chores, repairs, yard work, decluttering…whatever you didn’t fit into the weekend yet again.

3. You’ve missed out on too much. You have missed dinners with your family, dates with your spouse, family get together’s, BBQ’s with friends, vacations, adventures, gym time, reading time, time in your hobbies, travel and long walks on a relaxed Sunday afternoon. This can skew your Ideal Day/Week or Year because it’s just full on all the stuff you want to catch up on, not realizing at some point, you will feel caught up.

Sign up here to get the full Ideal Day, Week, Year Conversation Starter outline plus two more bonus money mentoring outlines.

I can’t have it, so why think about it.

This is another stumbling block we can face. Our Ideal Day seems so out of reach that we don’t even want to imagine it. BUT. Life will present us with choices, some small and some significant. If you have a clear idea of where you want to go it will dramatically effect the choices you make. The small ones and the significant ones. Your time off and weekends will start creeping closer to that Ideal Day or Week.

Plus it’s a great way to have this conversation with the people you share life with. Partners and kids also have an Ideal Day wanting to come out. Our kids Ideal Day is adventure, outings and board games or craft projects. Just because we can’t make that every day, all day, doesn’t mean we didn’t have the conversation or try to add a slice of that into our life. We came up with “Family Fun Night” that is just games, art and family fun kind of stuff. No cell phones, computers or chores.  We also do “Weekend Adventure” where we get out every week and do a fun event, outing, or adventure of some sort. And the trip to Costco doesn’t count…even if there are samples.

If I win the lottery day

This isn’t “What would I do if I had 50 million dollars?” Think about it if all your basic expenses were covered, maybe plus 20%. Just stay in the realm of reality. That way if you earn extra money in your ideal day, it will give you some extra cushion. Because that is how most people do end up feeling in retirement. Any extra money they earn buys fun extras.

Here’s how to spot Road Blocks:

If your list is just naps, short term projects, or hobbies that might be burn-out talking.

Honestly, it takes time to overcome burnout, depending how crazy your life is, maybe 12-36 months. That’s ok. It’s why we have to come back to this question over and over. Life changes, and we change. After 12 months of travel, you might be satisfied with that area. Maybe instead of traveling full time, you would then be happy traveling for 2 or 3 months a year. It might take a few months just to get caught up on sleep! And if you have kids at home, things change quickly! They change, and our Ideal Day changes right along with it.


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. Give yourself 30-60 minutes.
  3.  Write it down somewhere.

You can find a way to make a few adjustments to bring this year a few inches closer to your ideal. And if we keep our ideal day/week/year 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. Is there anyway to test this on a small scale?
  2. Do these Ideals make space for all the things truly important to me? Or are they tilted to the one area I feel I’m missing most right now? AKA There is LOTS of travel but little space for health or relationships.
  3. What steps could I start taking NOW that would make it possible to move towards this Ideal Day in the next 5 years?
  4. Is this the schedule I would want long term or just for a year or two till I feel caught up? How would this “ideal day” change in 5 or 10 years?


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:

Have you been able to move closer to your ideal day/week/year?

What might one of those look like for you?

Anything that is really missing from life now that you would add into your ideal?