Don’t Forget To Dream Big And Often

Dreaming Of A Ferris WheelPersonal finance is wonderful because it allows us the opportunity to dream of possibilities. When I was a freshman battling for a spot on the varsity team, I fantasized about being a professional tennis player signing balls after sliding on the red clay of Roland Garros. Every time I attend a tournament now, I feel like a kid again.

As a poor college student, I dreamed of making big bucks on Wall Street every time I passed the overly diligent business school students huddled around a TV showing CNBC. I imagined whipping around hundred million dollar positions on the prop desk as traders on the other side wondered what the hell I was up to. After a profitable day's work, it would be off to Peter Luger's Steak House in a black car with some clients, some friends and a corporate card of course.

After a couple years of marathon workdays in New York City, I dreamed of being free to set my own schedule. My health was fading and I didn't know how much longer I could last getting in before sunrise and leaving after sunset. As a poker fan, I always imagined winning the WSOP multi-million dollar first prize. Some would hand in their resignation the next day while giving their boss the bird. I would continue working because work becomes incredibly more fun when you don't need the money. Besides, I'm the WSOP champ, baby!

Now that I've retired from the corporate world, I continue to dream about all the possibilities. A dream within a dream if you will as I never imagined the ability to break free so soon. Why not run different financial scenarios and imagine what type of opportunities might arise in 25 years?

A reader commented in the 2013 Goals post how surprised they were to find “Live Free” as a goal. Paradoxically, it's hard to live free when you've got to make all your own choices. But, I'd rather have choices than have no choice at all.

I dream of progress. I dream of adventure. The best part of dreaming? Anybody can do it because it's free.

What do you dream about?

23 thoughts on “Don’t Forget To Dream Big And Often”

  1. Great post. I am a big dreamer, and I always dream big. If I can write fiction and my blog (yes, both types of writing are equally important to me) for a living, my biggest dream would be fulfilled. But I am okay with accepting a thought that this might never happen, so I just squeeze in my writing whenever I can. It is part of working on my dream. :)

  2. Without dreams, the world would be a cold, dark place indeed. Dreams, faith, and hope are among the most powerful forces of the human spirit, and sometimes we just need to believe in a dream strongly enough to make it into a reality.

  3. Having the freedom to not worry about needing to go to work to pay the bills and being able to call my shots on my own schedule….all on the back of my dividend income …. but i believe more and more with each day that that dream will become reality in the near future.

  4. Kim@Eyesonthedollar

    I dream about working when I want because I enjoy it, not because I have to. I also dream of not having to do housework or ironing!

  5. The First Million is the Hardest

    I dream all the time. It’s what motivates me to get up and work my a** off everyday. Possibly more important than having dreams is being willing to try and chase them down, making them reality.

  6. Andrew @ Listen Money Matters

    I dream of a time in the not too distant future where my wife (now fiancĂ©) and I live in our condo with enough money that we both only do what we want. I wouldn’t stop working because I honestly love it only I would work on my projects and hire people when necessary to help me achieve my goals. I dream of a simple life not much different from my current one only money is no longer a concern. No mansion or fancy cars, just security and unlimited options.

    1. Congrats on your impending marriage. I’ll be curious to hear your thoughts on work 5-10 years from now. I thought I wanted to work for 18 years straight in the same field until 40, but I only lasted for 13 years b/c I found something else that tugged my soul.

  7. I dream of getting out of the main stream corporate world in 2-3 years, seeing every continent in the world, and getting one of my photographs featured in a major photography publication.

    I’m looking forward to a happy and productive 2013 and going on adventures myself. I’m hoping to take at least one international vacation this year. I’ll be on top of the world if I can squeeze in 2!

    1. That would be very cool to get one of your photographs featured in a major photo publication! Might simply be a game of numbers… take more, submit more, increase your chances!

  8. I dream all the time! It is good to dream something impossible and find that you can get closer to that dream, even by a little bit. I dream of a life where money would be no object. Not millions, just enough to cover basic needs and a little fun. I dream of a big house always open to friends and family, with a big garden, growing fruits, vegetable, raising animals… So far I am happy with the small version of that dream!

  9. If you truly don’t need the money and have a job you love it would make it much more enjoyable if you make the decision to go to work rather than being forced. If you don’t like your job though I don’t see it getting any better.

    Dreams are awesome for sure. Goals are for the more realistic stuff.

  10. I think I achieved many of my dreams, however I am finding new ones. For me, the next step is turning those dreams into goals. I think you need to dream to put together a group of ideas where you can pick out the dreams you want to achieve. I always found it interesting how a road to a goal never goes straight to it. You pick up experience that helps you toward your goal.

    At one time, I thought being a writer was just a dream! I love the independence of a writer and having people interested in what I say.

  11. Dreaming is something I have done all my life, however, I have never thought about how much dreaming I could really do when it comes to finances. I definitely have some reevaluating to do. Thanks for sharing this!

  12. I think there are two kinds of dreams. One heavily based on imagination, and those are typically the ones we all like to share. You know winning the 500 million dollar lottery right. The second are the dreams that are within your reach in time. Here are a few of mine.
    Retirement, financial independence from a good paying job if I had to walk away, putting my child through college so they dont inherit a mountain of debt, a second vacation home, cruising different areas of the world, and travelling around the world for business.
    One dream I have met is paying off my home, it is a great feeling. Another dream I have almost completed is fulling funding my childs college fund. I have done some cruising and I have travelled to a few places around the world I wanted to see while on business.
    Still have a ways to go on the others.

    1. I like the ones based on imagination. A lot of imagination comes true, and that is the point where you start saying, “I can’t believe in my wildest dreams this his happening!”

  13. Thanks for the reminder Sam. I dream of paying off my house in the next 2 years, and then it’s time to invest heavily in my future (along with having some fun along the way of course). Good luck to you and your dreams! Keep in touch!

    1. Thanks Derek. That will be great to be mortgage free in 2 years so young. For tax optimization purposes, I’m keeping mine for as long as comfortably possible. To each their own!

  14. “work becomes incredibly more fun when you don’t need the money.” I dream about this often while working my day job. How cool would it be to be a trucker just for fun because I make more than enough with my side hustle income? That is what I dream about. I would feel like a total bad-ass around the other truckers!

    1. It’s fun to dream isn’t it? Like being a secret billionaire at work. Boss yells at you, and you’re like, “Yep! Should I buy the company and hire a boss to be his boss?” :)

Leave a Comment

Your email address will not be published. Required fields are marked *