Work Your Dream Job and Become Financially Independent

The other day I was wondering what my life would have looked like now had I taken a different path right out of college.  At the time, I thought about postponing my job search for a year to travel the world with nothing but my backpack and sandals.

Don't let this happen to you.
Don’t let this happen to you.

I had visions of being like Leonardo DiCaprio’s character in the movie The Beach (the first half anyway) and wandering around Southeast Asia and beyond*.  I probably would have ended up as one of those guys with blonde dreadlocks working odd jobs in farmer’s fields and cleaning hostels to try and scrape together enough money to fund my travels.  This sounds pretty horrible to me now, but at the time this was my idea of a dream job.

See, the problem with “dream jobs” for most of us is is that they either have ultra-low pay, are highly unobtainable, or are some degree of both.  Unless you have a world-class talent that can carry you to riches doing something you absolutely love to do, I suspect most of us are just average people doing rather ordinary things for a paycheck (not that there’s anything wrong with that).

I’ve had a couple friends who pursued their dream job and said “to heck with the money”.  One essentially became a ski bum and would travel between resorts in North and South America as an instructor so he could ski every month of the year.  Another dropped out of college and moved to Washington State to guide tours and climb mountains.

When I travel, I meet these types all over place.  They are the ones with smiles that never seem to leave their faces.  These folks earn enough to live on but I suspect not enough to be able to fuel a goal of financial independence.

A New Perspective

Mark Twain has been incorrectly credited with saying:

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did to.”

This quote haunts me and I do everything I can to limit its truth in my life.  Instead of lamenting all the things I wished I had done, why not turn this whole idea on its ear?  Because my dream job list likely wouldn’t lead me to being financially independent, I first plan on accomplishing this in under 20 years which will leave me the remainder of my life to do as I please.

I used to believe “dream jobs” were reserved for the young (and usually monetarily challenged), lucky, extremely talented, or overly adventurous.  And that working a dream job was a temporary thing until you eventually had to find a “real” job.  But by changing up the order in which these are completed, it opens up all kinds of options – there is virtually no limit **.

I’ve found that when I start dreaming a little bit, it helps me keep on track and gives me the kick in the pants I need when I’m about to spend frivolously.  It gives me that little inertia to keep me headed toward my goals and things that keep me fulfilled.

Just within the last couple of weeks, I’ve come up with the following dreams, some of which aren’t even jobs.

  • Bike the Pacific Coast Highway
  • Become a Peace Corp volunteer
  • Be an apprentice luthier in the creation of guitars and ukuleles
  • Teach elementary school children

Let’s face it, if you are driven enough to gain financial freedom before you need regular colonoscopy exams (recommended to start in your 50’s, by the way), you probably aren’t going to retire on a beach doing nothing but sipping Mai Tai’s.

Your Perspective

Since you are reading this blog, I’m going to assume you have some inkling to retire “early” so let me ask…

When money is no longer a consideration, what is your dream job or activity?


* Not being one to let a dream go without passing, I ended up compromising.  I got a “real” job but made sure it didn’t start for several months after graduation.  This allowed me to travel to SE Asia where I spent time in Singapore, Malaysia, and Thailand (including Koh Phi Phi island where The Beach was filmed a few years later).

** Yes, one could argue that not all dream jobs are available to early retirees in their late 30’s, 40’s, or 50’s.  The only exceptions I can think of are:

  • a professional athlete of a sport that requires perspiration
  • a superhero (for the main reason that most of us wouldn’t look good in superhero spandex tights at our age)

9 thoughts on “Work Your Dream Job and Become Financially Independent”

  1. Hi Buck. I was weird…never went to college to get a degree; I was more interested in earning money. The problem was that I sucked at managing it for the first half of my life. I’ve been fortunate that I had jobs I loved working for great people.

    Now, post colonoscopy (more info than you wanted, I’m sure), I’m pursuing my dream job and that was only possible because I got focused on eliminating debt and building wealth in my early 30s. I don’t see myself ever distilling my life down to sitting on a beach sipping a Mia Tia (not that I don’t like doing that). It’s just too much fun to figure out how to be of value to other people while generating income. Unless you get Alzheimers you can do that at any age!

    Ree ~ I blog at

    1. “more info than you wanted, I’m sure” – Naw, we’re all friends and here to share! Sounds like you’ve got most of it figured out, Ree. Good stuff and thanks for taking the time to comment.

  2. Great post!

    My dream job would be to help individuals and families with their budgets, so I guess a personal finance adviser. I’ve been looking into getting my CFP. But I don’t want to work for a firm, I’d want to work for myself. That way, I can dance on the side!

    1. Nice, Lisa. In another life, I think I would have been a CFP as well. I’ve worked with a couple of them over the years and have always thought “I could see myself doing that” and thought it’d be a pretty cool job. Thanks for commenting.

  3. Honestly Buck I had my dream jobs per se. I have done digital marketing and SEO for over 7 years and would say this is my dream career. Only problem is that i have hated working either for certain people or the companies. For that reason I decided to go out on my own and start my own firm. If I didn’t need money I would still do marketing and SEO but spend more time volunteering with children and help orphans. It is not always possible to become financially independent in my opinion doing your dream job unless you are making of important decisions. May be you want to be a dancer and maybe they dont make a lot of money but you are happy doing it. You love it but at the end of the day you will never be a millionaire. You have to adjust your living to do what you love. Or you can make money first then be financially independent then dance for the rest of your life. Just depends on what you want.

    Your tag line seems like my plans as well. I am loving to retire by 40 and move the family to Marbella Spain! Good luck achieving FI by 42 and moving.

    1. I like your style, Thomas. Good for you in identifying the issue and taking matters into your own hands. I agree with you, too. People do adjust based on their income and I’m plenty envious of those who have found their passion and are able to do what they love. I don’t hate what I do, but I certainly can’t see myself doing it until my 60’s.

      I’m interested in learning more and about your future plans. Will you be addressing your Marbella goal in your blog? Thanks for taking the time to comment.

  4. Damn, this one hits home. What you and I and what many others are doing are just tweaking our lives. Specifically, I really like this sentence:

    “But by changing up the order in which these are completed, it opens up all kinds of options – there is virtually no limit **”

    For me. this is the only way I could have ever done it. If I would have taken the “20 year old ski bum” path, I would have always been concerned about the future (What happens when I turn 40 or 60 and have no money?). By changing the order a bit and making smart decisions, we are still taking the ski bum path, but doing just a little later (our bodies are still in great condition) with no worries about the future.

    1. Yep, this is exactly what I was trying to convey…well said. With a few exceptions, you can work your dream job *and* reach financial independence , it just may not be in the order that you expect. It’s amazing how a little dreaming has refined our focus on our goals.

  5. “It’s amazing how a little dreaming has refined our focus on our goals.”

    Yep. Early retirees flip life on it’s head. I think of it as one of the best things we can do to hack our lives.

    The other thing I think about is that I almost missed the boat entirely. I didn’t even really think of early retirement as an option. My mind just never wandered there. Luckily, I was a saver so when I did see others doing it, I already had most of the finances lined up. Just a little bit longer…

Your Thoughts?