Questions to focus on enjoying the journey to Financial Independence

One of the main reasons I maintain this blog is to make sure I explore and document all my attempts to continue enjoying the journey on our path towards financial independence. I do not want to dedicate those years to solely focus on finding happiness once we would be able to quit our jobs, I want to make these years matter.  

That’s probably why this question posted on Twitter by Leftover Dollar stayed with me:

I love this question. It makes you think about the present and what you may be forgetting to focus on while you keep your eyes on that prize which we believe financial independence will allow us to attain. Ironically, while that goal of achieving FIRE is greatly dependent on income generation and thinking about how we spend our money, one of its very sought out gift is to move away from focusing on money. 

It’s important to reflect on this in order to try to incorporate some of the freedom FI will allow us to obtain even while we have yet to reach it. After reading this question by Leftover Dollars, I couldn’t help but think about other questions we can ask ourselves to generate similar reflections.

Sunny road

Incorporate our financially independent self in this journey

Along the line of thought of Leftover Dollars’ question, here are some various questions to try to see who we want to be once we are financially independent. These can also help us reflect on how we can incorporate our financially independent self along this journey.

  1. What are the activities I want to be doing once I reach financial independence?
  2. Which of these activities can I already explore in some form along the journey?
  3. Are there things I can be reading or viewing or listening to that can allow me to gain knowledge on those activities
  4. Do I know anyone that participates in some of these activities? 
    • What can I learn from them or how can I follow their own experience? 
    • If I don’t know anyone pursuing these, is there someone online or an online community which I can join or follow to find out more about these?
  5. How does my job prevent me from pursuing some of the things I wish to pursue once FI
    • Are there ways I can overcome these obstacles?
  6. Are there skills or knowledge that could be helpful with these activities that I could be acquiring through my current work?
  7. What would I do now if I could never retire
    • Would I choose a different line of work?
    • Would I explore a bunch of different activities to generate income?
    • Would I stay in my current job but make drastic changes?
  8. What am I thankful of having or being able to do right now?

One particular book that has amazing exercises around these lines of questioning, is Work Optional which I thoroughly enjoyed. 

Reflections on the Darker Side

The possibility and inevitability of death is always in the back of my mind – the thought that I or the people I love could die at any moment drives me to examine my life and strive for what I want now instead of later.” Why Retire Early? Because Death is Coming. By A Purple Life

I’m a huge fan of turning to dark thoughts to remind myself that the future is uncertain. Although I am a huge planner and always attempt to move towards a future that brings me happiness, it doesn’t matter how many times I visualize a potential perfect future, the only thing that is certain is the time I have right now. 

So along that line of questioning:

  1. If my time was to come to an end in a short time frame, would I be happy with my current life?
  2. If my loved ones were taken away too soon, would I have regrets on how I behaved with them or for not spending more time together?
  3. What are some experiences that I really want to have with my parents, children or other loved ones? 
    • Can I make these happen sooner than later without necessarily compromising our path to FI?
  4. For the experiences that depend on FI, what lies behind these, as in what am I hoping to obtain out of them?
    • Are there other activities I can do now with those loved ones while still managing to meet those sought after values and the essence of these experiences?
  5. Are there ways to reorganize our path to allow more time for these people now? 
  6. Am I spending the limited time I have with my loved ones in a way that feels fulfilling?
  7. What can I learn from people who have a set amount of time left on this earth?
    • What do they regret? 
    • What do they remember the most from their lives? 
    • Are there ways I can incorporate their lessons in my own life?

Our Children can be our Greatest Teachers

“Our children can be our greatest teachers if we are humble enough to receive their lessons.” — Bryant McGill

For the parents out there, the traditional “the days are long but the years are short” or “time flies” sayings sure have a lot of truth to them  As a mom, I feel like there is constantly more I can be doing and the need for patience is immense throughout these busy days. Still, every second of every day I’m filled with immense love for these little beings that I see grow and change way too fast. 

While they are young, we’re often the center of their universe and bombarded with their million questions about this world we live in. Despite the exhaustion, I’m also fully aware that the time with these kids that just keep growing and changing is limited. In a second they’ll be teenagers with a lot of attitude and little time to spend with me

So along the lines of questioning that can help me make the most of this time with our kids:

  1. What matters the most to my children? Getting sweet toys or getting to spend time with me? (Let the record show that my answer to this is that their favorite is getting sweet toys and then having me play with said sweet toys with them. I do like to tell myself that they prefer spending time with me than playing with a toy alone 😆 ). 
  2. Am I giving my children my undivided attention when I spend time with them?
  3. Are we experiencing unique activities and opportunity to connect on a regular basis?
  4. What does my daily routine look like from their perspective?
  5. What do I remember the most from my childhood?
  6. Am I allowing my kids plenty of time and opportunity to create some unique memories?
    • Will my presence and actions during those moments be an important part of those memories?
  7. When was the last time they had a deep belly laugh with me and how can I make those happen on a frequent basis?
  8. How long until I can no longer lift them or have them cuddle up on my lap?
  9. Will my kiddoes allow me pinch their cheeks like this while calling them adorable when they are a grown adult?
  10. What lessons do I want to teach them most about this life?
    • What am I doing to show those lessons to them?


These questions help me reflect on things I might want to do differently to make the most of the years on the journey towards financial independence. I truly enjoy having these types of reflections, since I believe it is so important to be happy along this journey.

It’s also why I thoroughly enjoy TheFioneers Slow FI interview series which demonstrate how others have chosen a more balanced approach to FI which makes them happier along the journey. 

What keeps you grounded on enjoying the journey towards financial independence? Or what if you answer Leftover Dollars question: What kind of person would you want to be if money was not the driver of your activities?

6 thoughts on “Questions to focus on enjoying the journey to Financial Independence

    1. Thank you :). Really enjoyed Work Optional and am actually getting it as a present for a couple of people for Christmas 🎁! The exercises in the book touch on some of those questions and goes deeper into aligning your trajectory towards a work optional life. Looking forward to knowing your thoughts on it :)!

    1. Yas! It is so good :). I frequently go back to my answers and look at that chart. Even had Mr.Mod answer all of these on a roadtrip and he also got a lot out of it!

  1. Some great questions. For me the ones about how you spend your time with people which resonated. Next year I have decided to save less and spend more on my holiday budget in order to be able to go away with my mum. She hasn’t explored the world much and wants to do so now. I have decided that’s more important than saving as she won’t be around forever.

    I haven’t read ‘Work Optional’, but may consider it now if it is as thought-provoking as you say.

    Thanks for the interesting post.


  2. I still want to go through those questions in Work Optional and now it looks like I have some more questions to add to the list. I used to spend a lot of reflecting but the habit has gotten away from me lately.

    Thanks for a post that reminds me to get that journal back out. 🙂

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