5 Questions to Uncover the “Why” That Will Drive You to Financial Freedom

by | BiggerPockets.com

I almost scrapped this article entirely. This has been a hard one for me to write. It makes me look like an ungrateful, spoiled-rotten Millennial. It is embarrassing, and I was afraid of how my family and friends might react.

Then I slapped some sense into myself. I would be doing a serious injustice to the BiggerPockets community if I wimped out and scrapped it.


Because the very reason I am embarrassed and ashamed is the very point of this article. It is my foundational “why.”

What is your foundational “why”? It is your gut wrenching, tear-jerking, knife-in-your-heart reason behind everything you do. It will likely be embarrassing, and it may even slightly offend some of those closest to you.

Once you can put a finger on your foundational “why.” You will feel like a new person. As Eminem so eloquently states, “you will have this newfound motivation to not give up and not be a quitter no matter how bad you want to just fall on your face and collapse.”

Let’s get to it.


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What is Your “Why”?

As in, “Why do you want to achieve financial freedom?”

You have heard this question a million times on BiggerPockets. The most common answers are to travel, to achieve financial freedom, to volunteer, to quit my job, etc.

For the longest time my answer was, “to travel and to spend unlimited time with my family and friends.”

While these reasons remain true, they are not powerful enough. It will be difficult for me to sustain this motivation for more than a couple of months with these reasons.

Seeking financial freedom is like climbing a mountain. There are going to be various points along the way where the view will be great and we are going to want to stop. With these reasons, it will be too tempting to stop at one of these plateaus where the “view” (or your life) will be good enough.

You will start saying, “I travel twice a year, that’s enough” or “I’ll be able to retire at 55 instead of 65; that’s better than a lot of Americans.” Don’t let yourself off the hook that easy. Dig deeper!

How do you find that motivation? That motivation to become this unstoppable force beelining it to the top of that mountain and achieving the ultimate goal of financial freedom?

Related: Why Following a Purposeful Schedule is VITAL to Happiness & Productivity

The answer is understanding your foundational “why”? Your foundational “why” is synonymous with your life’s purpose. It’s the real reason behind any sacrifice you make.

Keep reading so I can show you the 5-step process to finding your foundational “why.”

Getting to Your Foundational “Why”

The process of getting to your foundational “why” is simple. It involves having a conversation with your 3-year-old self. Please, do this in your head!

But this time, rather than ignore the silly questions your toddler self was notorious for asking, you will address them.

The only catch is that your 3-year-old self needs to start every sentence off with the same word. That word is “why.”

Always start this exercise with the 3-year-old you asking, “Why did you get out of bed this morning?” and respond to your 3-year-old self honestly. Your 3-year-old self will then respond with, “Why [insert your previous answer here]?” And you are to repeat this process five to eight times until you get to that gut wrenching, tear-jerking, knife-in-your-heart reason.

This is an important exercise. And I will warn you—you may feel ungrateful once you get down to the 5th, 6th, and 7th reasons. You may even feel as though you are offending some of those who are closest to you.

Don’t worry. The intention here is not to offend anyone, but it does mean you are getting closer to your foundational “why.”

Here is an example of the conversation I had with my 3-year-old self.

My Example

1. Why did you get out of bed this morning?

A: To go to work.

2. Why did you go to work?

A: So I can earn a paycheck and grow my career.

3. Why do you want to earn a paycheck and grow your career?

So I can increase savings and invest in assets that provide me passive income streams.

4. Why do you want to invest in assets that provide you passive income streams?

A: So I can be financially free, travel, spend times with family and friends, volunteer, donate, and not have to worry about a job.

Note: Most people stop here! While this can be powerful, it’s not powerful enough. It’s far too easy to say, “I travel enough” or “I love my job” or “insert excuse here” once your motivation wanes.

5. Why do you want to be financially free?

A: I was always told that the most basic form of success was to make the next generation’s life easier. I consider myself tremendously fortunate and am eternally grateful that each of the prior generations in my family worked hard to successfully create a better (and easier) life for the next generation to follow. That’s no easy feat, and I certainly do NOT want to end that streak.

To help answer this question, I performed an exercise where I reflected on my childhood to see what could have been improved. My parents, grandparents, and great-grandparents made this a very difficult exercise for me. I had everything a kid could ask for: a wonderful family who selflessly worked (and still do work) to give my sister and I unconditional love, support, and guidance.

But after digging real deep, I figured it out!

Because my parents were working so hard, their time with us was limited. By limited, I do not mean that they spent n0 time with us. The time we received was plentiful, but it certainly was not “unlimited.”

We could never take vacations longer than a week. They always had to get back to work. The profane “we can’t afford it” catch phrase littered our lives and restricted us from living to our fullest potential.

My purpose, my foundational “why,” is to completely free up my time while never having to utter those “we can’t afford it” words again. That way, I can pursue my true passions. I can spend time with my parents as they grow old, my (future) wife as we grow old, and my (future) kids as they grow up and have kids of their own.

That is why I wake up, to go to work, to earn a paycheck, to invest in cash flowing assets, to create financial freedom.

Related: Working With Purpose: How I’ve Found Focus By Developing My “Why”

To be able to provide my family with what they want—which I believe more than anything will be my time.

How do I make my time spent with them invaluable and unlimited so I will rarely need to worry about leaving precious moments to “going to work”?

I need to create a passive income streams that sustain life’s expenditures. To simplify, with $10,000 of monthly passive cash flow and zero hours worked, I will be able to sufficiently support my family while making my time invaluable. Ten thousand dollars divided by zero hours worked is infinity.


Once I figured out my foundational “why,” my life went from average to spectacular. Knowing that I get a step closer to achieving my life’s purpose every day has sparked an unrelenting fire inside of me.

It is what gets me to wake up at 4:30 a.m. excited for work every day. It is why I own a duplex, but sleep in the corner of the living room. It is the reason I own a car that I don’t drive.

Most of all, it is the reason why I enjoy doing these things and will be able to sustain doing them for a couple of years, until my goal is reached.

So now, I need to ask: What’s your foundational “why”—that gut-wrenching, tear-jerking, knife-in-your-heart reason you wake up every morning?

Be honest with yourself and share below!

About Author

Craig Curelop

After developing a huge love for real estate investing and personal finance, Craig decided to join the BiggerPockets team as a financial analyst. Over the past few years, he has looked at hundreds of financial models of startup companies. His experience will help BiggerPockets reach the next level as a startup company. Craig has a passion for helping others get out of their "comfort zones" to get what they want and achieve the "impossible." In his spare time, Craig enjoys traveling, hiking, exercising, and sports of all kinds.


  1. Kim Horn

    I found this article to be interesting. I never thought of having a conversation with my 3 year old self. For myself, I want to look back on a life of no regrets and not allowing fear to rule my thoughts. I feel that I am always second guessing myself. I want that to stop! I want to trust that I know deep in my heart that I am making the right choices. Craig, thank you for not scrapping this article!!

  2. karen rittenhouse

    Absolutely right, Craig, you’re “why” has to be big enough to get you over the tough hurdles and keep you going when you’re knocked down again and again.

    My “why” is and always was about my kids. I never want to be a financial burden to them in my old age. My goal was first trying to take care of my own needs, then not to be a burden to them. I never dreamed, starting out, that the results of real estate investing could grow into the amazing lifestyle it has created and the ability to give and do for others that we have. I will not only never be a financial burden to my family, but am actually creating a financial blessing!

    Thanks for your post.

  3. Nathan G.

    I don’t mean to sound judgmental but what’s wrong with only taking a week of vacation? What’s wrong with telling your kids you don’t have the money to buy something? When children grow up without limits, they become Paris Hiltons: spoiled, demanding, entitled, ungrateful, and with a low work ethic. They’ve never gone without or learned to sacrifice. It’s not true in every case but it’s certainly more likely than not.

    I could take a month off and spend it on the beach with my kids but a week is enough. I could buy my son a brand new dirt bike but the $600 one is already more than he deserves. And when my kids want a $15,000 side-by-side like their cousins have, I’m OK telling them we can’t afford it even though we can.

    I’m selfishly setting limits so I have more money to invest. My kids will have nice clothes, an above-average home, plenty of food, and far more experiences than I ever had. They will inherit something from me whereas my only inheritance will be debt.

    I’m not investing to give them everything they want. I’m investing for me and to help those truly in need. The oak grows strongest when exposed to the storm, not when it’s sheltered. The best gift I can give my children is not unlimited time or a big inheritance; it’s my example of working hard to provide for my family and then caring for others out of my abundance.

    • Craig Curelop

      Nathan – thanks for sharing! You make a valid point and honestly, I think we are in agreement.

      I am not saying you should spoil your kid in any way. Saying you “can’t afford” it and meaning it are two totally different things. You should be able to give time to your kids the time they deserve while also teaching them how to work hard.

      It’s all about optionality. Doesn’t it make sense to have the option of taking a summer off to spend with your kids than having to send them to camp?

      Also HAVING to work makes you run the risk of missing some of the most valuable moments. First steps, school plays, little league homeruns, etc. I would want to make sure I am there for those moments rather than working so someone else can watch their kids.

      • Amber Porter

        Giving kids things doesn’t make them spoiled. If they learn to be thankful, grateful, and generous, they are not spoiled. Also, teach that we should trust in our wealth. It can vanish in a flash and you can’t take it with you.

    • Colin Reid

      I’m with you on the spoiling part. I wasn’t spoiled, and I know my folks had the money to do things they said we couldn’t afford, but those sacrifices taught me how to work for what I wanted.
      My son lives with his mother, and going forward, I’ll have to spend a lot of money to travel to see him, take him places, have experiences with him, and just be a dad. That’s my why right now.
      The sooner I can reach FI, and stop trading time for money, the more time and money I’ll have to spend with him. I won’t spoil him, but I will show him what a life is like when you’ve front-loaded your work in the right ways and can reap the rewards from that hard work without having to spend the time.
      I have short and long-term goals for my why. Short term, I want to get rid of a job. Any job. Just be done with having to be somewhere at a certain time in order to support myself. I will fill my time as a flight instructor, getting paid relatively little, and only per-hour of flying. But I love teaching people how to fly, so that’s what I’ll “retire to,” rather than “retire from.”
      Long term, I’d love my REI business to grow enough to justify my own plane. That would make seeing my son easier, and fulfill a lifelong dream.

  4. Moriah Lee

    I’m a Peace Corps volunteer in West Africa living in and among what we in the USA would call extreme poverty. We’re now incorporating lessons learned from a study in Togo conducted by a German university wherein control groups of small business owners were given psych/motivational training or technical business training. The groups who received the accounting and business training increased incomes by 0-5%. Not bad. Until, you hear that…. wait for it… motivational training increased incomes by 30% or more. Trite to some. For me, and other people who don’t have natural communities of wealth creators around them, these posts are vital for success. Thanks!

    • Craig Curelop

      Thanks, Moriah!

      I’m glad that you thought this was valuable! Also, thank you for volunteering in the Peace Corps. That’s definitely something a lot of us could not do. You’re doing your duties in helping make the world a better place!

  5. Another great “secret” beyond the “Why Exercise”, make sure your motivation, your reason, your “why” has a face, other than your own.

    If you are only pushing for you, you’ll very likely quit or give up when something smacks you in the face.

    Another GREAT exercise, take 3 minutes and write out your eulogy – you’ll find no one ever says at their funeral: “_________ had a really great car or a really big house”

    it’s always “________ was a great father, a great husband, a great leader”…..it’s what REALLY matters!!!

    More great stuff coming out in my next book – “Get Off The Couch, Learning To Swim, Bike, and Run After Your Dreams”!!!!

  6. Craig Curelop

    Hey Chris – I am sorry you feel that way. I commend you if you feel that these articles are unnecessary and you are already self-motivated. However, there are many people who are not. That’s who articles like this are for.

    I hope you continue to read and pull some value out of these articles.

  7. John Murray

    All the whys can be answered without a great deal of thought, you nailed all the essential reasons to find financial independence. I never thought of my career as a passion, my vocation was my passion. People that bank all their success on their job are delusional. Now comes the hard part finding “how” to become financially independent. The answer is your vocation, skill level and passion. Without these three components you will never find out “how”.

  8. Terri Dyer

    Love this article with your 3 year old self and really getting to the root of why you want financial freedom. Good insight and an easy activity to do to figure out your why. So then you can figure out what you truly need to do to accomplish it and start living your why.

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