Happy New Year, Happy 10 Years

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The week after Christmas has always been my favorite week of the year, and New Year’s Day my favorite Day.  As a huge fan of fresh starts and clean slates…to me it just doesn’t get any better than January 1st.

Additionally- and I know I’m in the minority here, I’ve never been a big fan of the holiday season, and that’s somewhat of an understatement. I get horribly depressed come November each year (actually, October if I’m being honest) and it’s gotten much worse since my Mom passed away. It’s a tough time of year for me, and I always breathe a sigh of relief when it’s finally over and January 1st is within sight: I look forward to New Year’s Day like most people look forward to Christmas.

So anyway, this New Year’s Day was extra special to me because not only did I make it through yet another holiday season without having to check myself into the psychiatric ward, but more importantly- I celebrated my ten year anniversary of being my own boss..woohoo!

Ten freaking years, man- it’s hard to believe.

It was on January 1st of 2007 that I finally ended my illustrious career as a bartender (I chuckled as I typed that), and went into the house flipping/wholesaling business full time. Looking back now, I guess it was a pretty ballsy move considering the fact that I didn’t really know what the hell I was doing (I’d flipped three houses prior to jumping in full time and was still figuring things out) but I’d had all I could take of slinging drinks for a living, and could no longer stand being an employee.

For as long as I could remember, I knew that one day I’d go into business for myself, and once I realized that I could make money flipping houses- I couldn’t get my ass out from behind the bar quickly enough.

My journey as an entrepreneur has definitely not been an an easy one (you can read more about that later on in this post), and I’ve learned some very hard yet extremely valuable lessons along the way that I wanted to share with you guys today.

For anyone reading this who has aspirations of ditching your J-O-B and going into business for yourself, my hope is that you will find some motivation and inspiration from the lessons that I’ve learned over the last ten years, and that your path into self-employment will be at least a little bit easier than mine was as a result.

So here we go….

Lesson #1: Feel The Fear And Do It Anyway

Although there’s definitely been no shortage of obstacles to overcome since going into business for myself, none have been as challenging (by a long shot) as dealing with the constant self-doubt and fear that take up residence inside my head when I’m attempting something new and challenging.

And while it can seem almost paralyzing at times, I’ve learned that when those feelings of fear start creeping into my brain- I have to keep moving forward despite the fact that I’m scared out of my mind. It might be uncomfortable, and it might be intimidating, but I know that unless I venture outside of my comfort zone, I’ll never make progress and I’ll never get to where I really want to go.

Fear can be a real asshole, man, and it will smash your dreams into a thousand little pieces if you don’t learn how to deal with it, and more importantly: how to act in spite of it.

For example…

I remember going on my first real estate appointment where I was meeting up with a seller and attempting to negotiate my first deal. I arrived about thirty minutes early, parked a few blocks away from the seller’s house and sat there in my car on the side of the road trying to muster up enough courage to actually pull into their driveway and go knock on the door- I was scared shitless and all I wanted to do was go home.  My hands were shaking so badly and I remember thinking to myself that there was no way I could possibly pull this off.

So I sat there in my car as the minutes ticked by, and although I was literally shaking in my shoes and had to force myself to do it…I eventually got up enough nerve to drive down to the seller’s house, knock on the door, and go inside.

The appointment lasted about thirty minutes or so, and although I don’t remember much of what happened during the half hour that I was inside, I do remember (with shocking clarity), the feeling of exhilaration, confidence, and accomplishment that came over me as I left the house and walked back to my car: I felt like a total rock star and still remember doing a fist pump and yelling “Fuck yes, I did it!” after I shut the car door behind me.

I never made any money as a direct result of that first appointment, but the lesson I learned that day when I made the decision to be brave and take action despite the fact that I was scared out of mind, is a lesson that I can not put a price tag on and one that still guides my actions to this very day.

In fact, I have several projects lined up for 2017 that scare the living hell out of me- projects that take me so far outside my comfort zone that I literally feel sick to my stomach just thinking about them.  And while chickening out and remaining in the cozy confines of my comfort zone would be the easier and safer path to travel in the short term- I know that playing it easy and safe will never get me to where I want to go.  So I will feel the fear and I will act in spite of it, because I know that doing so will take me one step closer to achieving my goals.

Lesson #2: It Ain’t Easy, But It’s Damn Sure Worth It

My decision to go into business for myself was never about the money or about wanting a bunch of unnecessary material crap- I could honestly care less about that stuff.  For me, it has always been about freedom: freedom to come and go as I please; freedom to go to the beach on a Monday and drink a beer at noon just because I can; freedom to go wherever I want to, whenever I want to and not have to answer to anyone but myself. 

I’m sitting in a coffee shop as I type these words, drinking an iced vanilla latte on a weekday morning. When I’m finished here I’ll probably head to the beach, take some pictures, and say hello to the ocean.  I ain’t gonna lie- it’s pretty fucking awesome to have this type of freedom in my life, but I would be lying if I told you I hadn’t paid a high price to get it.

The truth of the matter is that nothing has come easy to me as far as my business is concerned- nothing has ever just been handed to me that I didn’t have to first work my ass off forI’ve paid my dues, man, and then some.  But despite the many obstacles I’ve had to overcome, the struggles I’ve had to work through, and the hard work that has been (and is still) required of me…As I sit here sipping my delicious vanilla latte (Thank you, Intermezzo Coffee!), I can tell you that all of the hard work and all of the struggle has been without a doubt 100% worth it.

Knowing this, I will continue to bust my ass and chase down the lofty goals I’ve set for myself for 2017 and beyond- and while I know it will definitely not be easy, I also know that in the end it will damn sure be worth it.

Lesson #3: If You Want Something Badly Enough, Don’t Give Up Until You Get It…Period.

When I made the decision to pursue real estate full time and quit my job at the bar effective January 1st, 2007, I was 100% all-in and 100% committed to succeeding. There was no half-assedness about my decision…it was a “do-it-or-die-trying” type of undertaking.

I made a promise to myself back then that no matter how many times I got knocked down, I would get right back up and keep fighting; No matter how many setbacks I faced, I would keep on hustling toward my goals until they were achieved; and most importantly…under no circumstances would I ever work for someone else again.  My days of being an employee were over, and even if I ended up living under a bridge for a little while…I promised myself that I would never go back to working a J-O-B (tending bar or otherwise).

As it turned out, the universe was listening when I made those promises, and being the sadistic bastard that it is…it decided to put me to the test and see just how committed I really was.

(Good times ahead…woo!)

Over the course of the next six months I worked harder than I’d ever worked in my entire life.  I pushed myself so far outside of my comfort zone time and time again, all the while keeping my eyes on the prize and a laser-like focus on my goals. But no matter how hard I tried or how fiercely I hustled- every deal that I tried putting together ended up blowing up in my face due to factors beyond my control.  I just couldn’t seem to catch a break no matter what I did or how hard I worked.

Frustrated beyond belief, and after nearly six months of busting my ass with nothing to show for it except for mounting self-doubt and a rapidly dwindling bank account…I was at my wit’s end. I literally had a couple of dollars left to my name at that point, had just borrowed eighty bucks to cover my electric bill (sad but true), and was headed towards a serious financial shit storm if I didn’t bring in some cash before the month was over.

The good news was, I had a deal scheduled to close the following week where I’d be making a quick four grand by flipping a contract to an investor. That 4k payday was basically gonna save my ass, but if the deal didn’t close, well…I was pretty much screwed.

Perhaps you can see where this story is headed…

It was a couple of days before the closing when my phone rang while I was out walking in the woods behind my crappy little apartment trying to clear my head so I could get through the day without having a nervous breakdown. When I looked down at my phone and saw that it was my title company calling, I was immediately filled with dread: I knew something was wrong before I even said “Hello”.

Sure enough it was bad news, and in the space of that three minute phone call, the wind was sucked right out of my sails and I could feel my ship beginning to sink. Turns out there was a (very large) IRS lien against the property that the seller had “forgotten” to tell me about which essentially blew the entire deal to smithereens and along with it…my four thousand dollar payday.

Son. Of. A. Bitch.

When the phone call was over, I sat down on a dirt path in the middle of those woods and started sobbing uncontrollably in a crumpled heap of misery. I’ve never been one to wallow in self-pity, no matter the circumstance- but at that point I felt hopeless and defeated, and for the first time in six months…I felt like giving up.

I don’t remember how long I sat there crying on that path, but I do remember that when my tears finally subsided and the sting of yet another lost payday had faded just a teensy bit…my feelings of self-pity, hopelessness, and defeat soon gave way to those of anger, resolve, and determination. I was pissed off, is what I was, and although it sucked beyond belief that the four thousand dollar paycheck I so desperately needed had just gone up in smoke right before my very eyes, I refused to let it stop me: I’d come this far and worked this hard and I’d be damned if I was gonna quit now.

So I got up off the ground, dusted myself off (both literally and figuratively), and then proceeded to shake my fist in the air in dramatic fashion while yelling “Bring it on, motherfucker!” to no one in particular. Probably it was a bit on the crazy side, and if anyone was watching me I’m sure they got a good laugh (or scare) out of it,  but I didn’t care. I was pissed off and determined, and ready to take on the world again.

Bring it on…

There’s a curious thing that happens when you reach your breaking point and resolve to keep on going anyway.  I’ve talked to others who have experienced it, and I’ve also read about it in many a motivational book.

Following is a quote from Napoleon Hill’s motivational classic, Think and Grow Rich (a book that changed my life, btw), that sums it up quite nicely…

“Before success comes in anyone’s life, he is sure to meet with much temporary defeat, and perhaps, some failure.  When defeat overtakes a man, the easiest and most logical thing to do is to QUIT.  That is what the majority of people do.

More than five hundred of the most successful men and women this country has ever known, told the author of this book that their greatest success came just one step beyond the point at which defeat had overtaken them.  Failure is a trickster with a keen sense of irony and cunning.  It takes great delight in tripping one when success is almost within reach.”

I was at my breaking point that day in the woods, and although 99% of people probably would have given up right then and there, I refused to give in and instead made the decision to keep on going no matter what.

It wasn’t too long after I made that decision that my hard work and perseverance finally started to pay off- and in a big way.  Of course there were still plenty of challenges and struggles that followed, but I’d made it over the hump and I knew that I would be OK.

Looking back on that time period, I can easily say that those were some of the toughest, loneliest, and scariest days of my life, but I wouldn’t change any of it for the world.  The lessons I learned by persevering when it felt like the entire universe was conspiring against me, made a huge impact on my life by showing me that anything is possible if I set my mind to it and refuse to give up.

Looking Forward…

I spent the last few weeks of 2016 making plans for the coming year, and as I sit here looking at my list of goals for 2017, I’d be lying if I said I wasn’t scared out of my mind.  Despite my fears, however, I will continue to chase after my dreams with relentless determination because I know that all of the hard work will be 100% worth it once those dreams have turned into my reality.  Life is way too short to settle for mediocrity. I want much more and I’m willing to do whatever it takes to get it.

Cheers to 2017, everybody…Happy New Year! ❤

-Steph 🙂

I’ll leave you with some pics I took on New Year’s Eve and New Year’s Day.  The first was taken on St. Pete Beach on New Year’s Eve,  and the last three at Alexander Springs where Rudy and I celebrated the first day of 2017. Couldn’t have asked for a better way to say goodbye to 2016 and hello the new year!

St. Pete Beach




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8 Responses

  1. Mermaid Girl
    | Reply

    One of my goals for 2017 is to finally make the jump from full time employee to being my own boss (I do graphic design and am ready to go out on my own). I can’t tell you how motivating and inspiring this post was for me right now. I am also very scared to leave behind my steady paycheck but I am miserable at my job and know I’ll never be happy unless I quit. It’s very encouraging to hear your story- congratulations!

    I’ve missed your posts and hope that you continue your writing this year.

    Happy New Year Steph!

    • Steph
      | Reply

      So glad you found some inspiration from the post- I was hoping that at least one person would! 🙂

      It’s definitely scary when you’re making the jump from employee to being your own boss, but like I wrote above- it’s definitely worth it.

      Wishing you all the best in 2017- I hope your transition is a smooth and successful one!


  2. Allison Reyes
    | Reply

    So you actually work! I follow you on Instagram and figured you we’re on a permanent vacation LOL!

    Congrats on ten years and Happy 2017 to you Steph! 🙂

    • Steph
      | Reply

      Haha- thank you, Allison! Happy 2017 to you as well! 🙂

  3. Maria
    | Reply

    I love it!!! You are just awesome and so motivating! Thank you for sharing Steph! Xoxox

    • Steph
      | Reply

      Awww, thanks for reading, Maria! I hope your 2017 is amazing! 🙂

  4. Mel
    | Reply

    You go girl! Congratulations on your ten year bossiversary!

    Glad to see you posting here again. I missed your stories and pics.

    Happy 2017!

    • Steph
      | Reply

      Thank you so much, Mel! I hope your 2017 is off to a great start!

      Steph 🙂

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