From 9 to 5 Grind to Living the Dream in 3 Months Flat

Have you ever desired freedom?

Freedom to support yourself while controlling what you do and when you do it?

Me too.

From the naïve young age of 13 that was my life goal and all I cared about achieving in life.

15 years later I found myself extremely nervously handing over my letter of resignation to pursue an uncertain and terrifying future where I no longer had a steady paycheck.

Did I have other income streams? Nope.

Did I manage to build up any assets of value in that 15 years of trying to forge this desired kind of lifestyle? Not really.

Was I going to be throwing myself into the most challenging and stressful situation of my life? Without a doubt.

All I had were a few connections and unbridled optimism that I could do better for myself… Do something that made me happy… Do something that didn’t involve a god-awful two hours of commuting daily and a once very enjoyable job that had rapidly deteriorated into a suffocating nightmare.

Two weeks later, shortly after my 28th birthday, my life would drastically change. Not for better. Not for worse. But for different.

I had just officially taken my Leap of Freedom.

I was entirely unprepared and it was nothing like the exciting day I had envisioned where I was secure enough to do something awesome like this:

Instead I was overcome with a depressing mixture of fear, regret and uncertainty.

Getting My Shit Together

The next two months were an emotional rollercoaster of stressful lows and optimistic highs while trying to figure out how I’d sustain myself financially.

During the highs I’d be reveling in my new found freedom and reaching out to my contacts to drum up consulting work. This is what I had dreamed of and I had finally made it.

During the lows I’d be trolling Craigslist and applying to every relevant job I could find in a sad attempt to jump right back into the rat race I had just escaped. Maybe I pulled the trigger a bit too quickly, let’s try to get paid a little more doing the same type of job and stick it out for another couple years.

I was a crazy mess swinging from one extreme to the other. Should I chose freedom and trust that I can make it work? Should I continue to build on my career and go back to getting a steady paycheck?

In those two months I had two very promising interviews that I was highly qualified for that came and went without job offers. I also managed to piece together two decent-paying clients and was in the process of landing a smaller third. Was the universe trying to tell me something?

It was at this point that I was contacted out of the blue by a recruiter and to both my excitement and disappointment, it was a job I was perfectly qualified for, offered an excellent salary and benefits package that far surpassed my previous job and sounded like a very fun and exciting place to work.

Excitement because, wow, what an opportunity for this to fall right into my lap at this very moment.

Disappointment because, I knew this could very quickly be the end of my freedom and I’d literally be making almost the exact same commute to and from the same city one hour from where I lived.

This was it. After two months of this emotional rollercoaster ride, I had to commit.

No longer could I continue to pursue both tracks, it was one or the other, I had to go all in and I knew this was the moment. Job and security or freedom and uncertainty.

I stood up from my computer, paced around for about five minutes and bam, the answer was clear. I hit reply and began my extended response to the recruiter.

This job sounds amazing and I would love to interview for the position… however, I unfortunately cannot pursue the job at this time.


It was done. In five minutes I had made one of the most important decisions of my life because deep down I knew. I knew that I wanted the freedom and knew that I’d never be happy going back to a 9 to 5 desk job and ultimately knew that this was my best chance at making this freedom thing work and that I had to try my hardest regardless of the cost.

So This is What Freedom Looks Like?

After a very unglamorous first two months of freedom I had finally chosen for certain my path in life. No going back now.

For the next month I buckled down and landed that third client while expanding my workload with the first two. I now had enough work to fully support myself relatively comfortably.

Was I making enough to replace my previous paycheck? Nope, not even close.

Was I going to have to pay substantially more in taxes because independent contractors get royally screwed over by the U.S. tax code? Absolutely.

But was I finally free to work remotely from anywhere in the world and support myself? Damn right.

So what in hell was I doing just sitting in a tiny room, grinding away day after day with very little human interaction?

Why was I not happy?

Why was this entirely unfulfilling?

I had worked my whole life to reach this moment, to achieve my childhood dream and, damn, it kinda sucked and was mildly depressing. This isn’t what freedom is supposed to look like.

I was very clearly doing the whole freedom thing completely wrong… I had to go somewhere, anywhere. Just needed to get away and actually take advantage of the amazing situation I had created for myself.

Fuck it, let’s go to India.

I love Indian food and my good college buddy currently lives in Delhi (his hometown). Let’s go live with him and work from there for a month and experience a whole new culture.

But what about my clients? Would they be upset if I wasn’t working locally? Would they be angry that I wouldn’t be available during regular business hours? What if I lost one or all of my precious clients due to this trip? What if this happened, what if that occurred?

What about the travel itself? I had never been outside of North America in my entire life nor on an international trip by myself. Could I handle being in a country half way around the world? Would I be able to manage the travel plans and get to where I needed to be without getting stuck or lost? What if this happened, what if that occurred?

Here I was again, in an internal struggle with myself over what to do.

This time however, I had one big factor going for me. I had trusted myself up to this point and everything had worked out surprisingly well. It was clear, I knew I now had to trust myself again in taking the next logical step in a freedom based life.

Within a week from the ‘fuck it’ moment, I had sorted everything with my buddy and booked my tickets to India. I’d arrive in four short weeks. No turning back now.

Flying Around the Globe… Twice

Here I was… boarding the plane that would take me halfway around the world. The start of an exhilarating and unexpectedly peaceful journey.

Ultimately, I was able to utilize my freedom to go have an amazing and completely surreal month long adventure in India all while keeping up on my work and maintaining rapport with my clients. Yet again, everything had worked out surprisingly well.

Within two weeks of being back in the U.S., I was on another plane across the ocean to Manila for a week to cover an MMA fight for one of my small hobby sites. This time all expenses were paid, all I had to do was show up and play reporter. I never would have been able to take up this amazing, out of the blue offer if I was instead back working at a 9 to 5.

Ah crap, a 23 hour layover in Tokyo on my way back to the U.S., how ridiculously lame is that? Wait a minute! I have another good college buddy who lives in Japan.

Now I also got to spend an entire day (and entirely too much money) partying it up with a buddy I hadn’t seen in five years in a country I never even planned to visit. It’s crazy how some things just work out.

Then within two days of being back from that trip I was off to my hometown to hang out with the family for a few weeks for the holidays. I hadn’t been home in nearly six years because I was too busy working and had too little vacation and hadn’t even seen my extended family in eight years. Such a refreshing opportunity to reconnect with my roots.

All these trips and amazing experiences I could never have imagined crammed into such a short period of time had suddenly become possible. All stemming from a series of seemingly risky bets on myself. All because I had chosen freedom over being comfortable.
Was I broke as shit? You betcha.

Was it difficult and challenging to figure out how to make everything work? Undoubtedly.

Was I loving life for the first time in god knows how long? Yes and it was a truly empowering feeling and well worth the risk and financial sacrifice.

Ok, so now it really started to sink in. How amazing this freedom lifestyle can really be. And how much I would have missed out on if just four months prior, I had taken the other path at the fork in my life journey.

Living the Dream?

The truth is, all this traveling while maintaining the discipline to successfully complete work and keep clients happy is hard.

While I was having amazing life experiences, I was broke and far off from the financial goals I had set for myself and been focusing on my entire adult life. And I still was at continual risk of losing the decent amount of monthly income I had managed to piece together.

When presenting this dilemma, both sides of the coin of a burgeoning freedom lifestyle, to my various friends, one common phrase was repeated over and over… “But dude, you’re living the dream”.

Well, I suppose I am. To some extent anyway.

The dream of not being tied down to a 9 to 5 job and being able to travel.

Would it be better if I had a larger income? Definitely.

Would I be happier if I didn’t have to rely on clients and the stresses that entails to survive? Oh yea.

But have I managed to experience a small taste of this “dream” and set myself and solid path to being able to fully realize it? Unequivocally, yes.

Maybe that dream never will quite be fully attainable, always 10 steps ahead of me, no matter how many steps I take. Maybe this is just what everyone thinks they want but it’s really not all it’s cracked up to be in the long run. Maybe I’ll end up ultimately choosing to go back to a 9 to 5 after hitting an obstacle too difficult to overcome.

Regardless, what’s important is that I made some serious progress in life, traveled the globe, had unique and crazy experiences, challenged myself in ways I had never challenged myself before and ultimately grew a ton as a human being in a very short period of time.

It’s a period of my life I wouldn’t trade for anything and something I would recommend everyone take a shot at at least once while they are relatively young. It really gives you some perspective on life and knowledge about yourself that you can’t gain in any other way.

So get out there, say “fuck it” and take your own Leap of Freedom. You won’t know what you’re missing out on until you try.

As for me? You can bet I’m still going to keep building on this as much as I possibly can.

Next stop… Bali.

Maybe I’ll see you there!