Money Mentoring Question: What is your “Ideal Day”?

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

How to do money mentoring with a friend

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?


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12 thoughts on “Money Mentoring Question: What is your “Ideal Day”?

  1. My ideal day would be one where I live in South America free of my 9-5 job. I’d have a kid of two without the need to worry about money because my passive income would cover my needs in a lower cost area. I’d be free to be extra involved with my kids life and teach them all the lessons I wish I would have been taught.

    Of course, it would be great to be close to a beach and free to explore as well!

    Thanks for the stimulating post!

    • I haven’t spent any time in South or Central America yet, but am really interested in the area. Especially with the cold Montana winters, I think I wouldn’t mind escaping down there for a month in February. It’s also great to think about it as in weeks in a year or hours in a day. Once you figure out the hours in the day, you can start making small steps right now to line your current life and ideal life up a bit more. Having that written down provides a bit of motivation boost for me. Even in things like planning BBQ’s with friends. It’s on my list!

  2. I’m really looking forward to working through this question. Last week was a game-changer for me: a call went out on our community group that a small child needed CPR. Long story short, she had fallen into a swimming pool, no one knows how long she had been in the water before she was found. After 30 minutes of CPR (medics arrived quite quickly to take over), she was pronounced dead. To watch a little girl die; to watch a mother watch her little girl die….. I can honesty say it changed my life. A harsh but healthy dose of perspective about time and the fragility of life. Thank you for helping so many of of us by sharing your story and leading us to think hard and take action.

    • Oh my gosh, that is horrifying! I can’t imagine to even witness that shakes you to your core. There is such fragility to life, and we just don’t know how much time we have. I try to keep a “no regrets” mentality. If something happens at least I know that I didn’t waste any time, any moments, or put things off any longer than absolutely necessary. Trying to live my best, fullest life every day. Not letting business, commercialism, or status quo steal away the things and moments most precious.

      Good luck with the question! After you spend some time on it, you might have some inspiration how to get there sooner rather than later. =) Shoot me an email with the image or text if you like. I would love to see what you came up with!

  3. Thank you so much for this series, and especially this article.

    It reminds me I wrote a post on this some 18 months ago. I need to revisit this and apply a few of your learnings.

    I am convinced as well that small changes no can bring us closer to where we want to be later.

    • I’m so glad you are liking the series! =) It’s a question that SHOULD be constantly adjusted. Because life changes, we learn new things about ourselves, we get new information, situations change, kids change. Small changes not only compound, but they also give us new information. Like if we want to get in better shape, we might start running 3x a week. In making that change, we might realize we hate running. So instead we try rowing, or yoga classes or cycling. And we find something new we love. And it changes our path. Now we want to spend a month cycling through Croatia. (Um, YES! But I’ll do it on the back of a motorcycle =) Then when you need to pick a vacation destination, you KNOW the perfect one. Good luck on the exercise! Let me know how it goes.

  4. I am at a point of living life simply – trying to define simple is just that, a little complicated process for the reason I still want to do many things:-)

    As our ideal life and reality sometimes interdigitate one way or another, I started by having a small list of things I want to complete. For one, I have tried to change my living room color and it has taken me more than 4 weeks trying to finish this task, as of today, I am 3/4 done. The difference between now and me 10 years ago, I would have gone into this unreasonable blaming for not getting things done – I know I have to finish the painting, but not much of blaming game and everything has to be on a strict time table. I consider that a good day.

    Of course there are other things that need my immediate attention and I am not a fan of procrastination. I think knowing what you can let go and be ok with it and focus on what’s important makes a tremendous difference for mental health.

    • It is such a process to learn how to be gracious with ourselves! Getting things done, but being flexible to the realities of life. With 5 little kids, that is 90% of my life. Having a plan that is in constant flux. =) It’s great to hear that you are making process! I’ve had a slow journey of learning kindness to myself. It’s easy for me to be kind to others. But to my physical body I can be a jerk. Not enough sleep, water, real food, exercise, rest… My recent mantra is “show kindness” which gets me to bed, gets me to the gym, gets me to take a long bath at night. =)

  5. Very interesting exercise. It makes a lot of sense to figure out what you want life to look like and see both how you might incorporate that now, and how that could motivate saving for retirement. I think what my ideal day would look like will change with different seasons of life. Right now while staying home with my kids it looks one way, but when they are at school, or one day out of the house, it’ll look differently.

    • Oh the ideal day totally shifts season to season. I tend to think of our life in seasons, (small kids season, big kids season, college kids season, grandbabies!) Our ideal day or year will shift each time. We are already starting to make our long term life plans around those seasons. What we REALLY want to do know when our kids are small. What will fit better when they are in high school. What we could do as they start to move out. The really cool thing is that we can lay the foundation for each upcoming season. I’m already prepping for the future seasons. It’s easy to lay a good foundation if you have 5-15 years to slowly gain the skills or information needed. =)

  6. Today is almost an ideal day for me.
    I’m working on my blog just a little today.
    Then I’ll take my kid to the playground and go grocery shopping.
    Go to town to get lunch from a food cart and hang out a bit.
    Go to the pool then make burgers for dinner. Maybe vacuum if I have a few minutes. Listen to the Blues Festival.

    It’s a full day, but not too busy. I’d like to exercise more today, but no time when the kid is around. I’ll just exercise a little at the playground.

    • That’s awesome! And sounds like a great day. =) Thinking about our ideal year has also been awesome. How many weeks of travel, how many weeks of renovations, how many weeks of rest or celebration. It helps me stay focused and not over commit to cool or fun ideas. =) There are SO many fun things we would like to do, but would kill our ideal year.