Finding the Courage to Pursue my Dreams
I was terrified, so I jumped
I’ve always done what I thought I should do whenever I didn’t know what I actually wanted to do. Digest that for a moment, I’ll wait. Does it make sense to you? Let me explain. Most people I’d venture to say don’t truly give their life thought, plan their steps or if they have made a true attempt at reaching their dreams. As kids we’re taught go to school, get good grades and get a good job — the end. The primary goal being attaining a salary by which we can live the lifestyle that we want to live. But is that enough to make us happy & fulfilled on a daily basis?
I followed the blueprint to the letter because what else would I do? With the exception of good grades I managed to earn a Bachelor’s and a Master’s and lockdown a salary which would support my lifestyle and eventually my family. I bought a house in 2009 and had what some would call a dream car at 27. I’ve been fortunate enough to travel the world and have a (legendary) destination wedding that my wife and I were able to save and pay for with cash. I say this not to brag, but to illustrate that my life isn’t bad at all. In fact, my personal life is perfect. However, professionally I had this itch that I just couldn’t seem to scratch.
I work in the IT industry in the DC metro area — in other words job opportunities are in abundance. I spent a large portion of my career with one company, almost 7 years, before deciding I needed a change. Staying with one company for 7 years for my generation is basically an eternity. I’ve always felt a pull to do more for my community in some way, shape or form. Years ago I started an LLC with a group of friends with the goal of offering IT consulting services. It quickly fizzled, never earning any real money. We’re all still friends to this day, but it wasn’t our time or we weren’t passionate enough or knowledgeable enough. Whatever the reason we didn’t find any success. In 2013 I registered my own LLC, Oliver Technology Group, with the hopes of doing the same type of business — IT consulting to state & local governments.

Before I continue let me be honest in saying I’m a procrastinator. If a paper is due at midnight and I’ve estimated its going to take me 3 hours to write I’m starting at 8:50pm. If I have to catch a 6am flight I don’t even start washing clothes until 12am. Yes, I know it’s a terrible habit, but I think most of us can relate to a degree. Even though I’m an admitted procrastinator I’ve always excelled at work. From one of my first jobs at Target to my current roles as a Business Analyst or Project Manager I’m very good at my job. While I may procrastinate at times I also take pride in my work or anything I’m responsible for producing. If my name is on it’s going to be top notch work. Also, while corporate America was a culture shock for me (that’s a totally separate post for another day) I got along well with my co-workers. When in lead positions I had developed good relationships with my colleagues so that working together was stress free and effective. But still something tugged at me — constantly seeing the same people promoted while it felt like we did the grunt work didn’t help either. I wanted more, I wanted to be more. How could I effect change and make a difference in my community spinning the hamster wheel that is corporate America?
Fast forward to fall ’17. I had secured what many would call a “dream job”. I worked ONE HUNDRED PERCENT remote (my couch, my bed, my kitchen table, my backyard patio, my office) while earning a six figure salary doing a job I had earned degrees for and tailored my professional experience specifically to do. Another added bonus was the company was based in LA which meant trips “on scholarship” as one co-worker put it to a place I absolutely love. I’d agree, it is in fact a dream job. The company culture itself was fantastic and my team lead was simply put amazing. She trained me on the specifics and it felt like she knew the answer to every question I asked. To sum it up, this was a job someone could work for 30 years and retire happily. That someone just wasn’t me.
When my 30th birthday approached I felt old as crazy as it sounds, but I also started to give serious thought to how I wanted to spend the NEXT 30 years. I just couldn’t envision myself working in corporate America for someone else. Also, the company I spent the majority of my career with was purchased by another company for billions of dollars making the owners and shareholders even richer. My salary stayed the same. To be clear, that is not a complaint — that’s how things work. If you own and build something someone is willing to pay for you will receive the lions share of the profit. For me, it was an eye opener — I needed to refocus on building something I owned. I left my comfortable job of almost 7 years, but instead of pursuing my dreams I made the mistake of chasing money. Judge me all you want, but when someone offers you a 30k raise and you’re already making over six figures let me know how easy it is to turn it down! I lasted at that company 6 months before leaving and joining the LA based company.

I decided to leave the ONE HUNDRED PERCENT REMOTE six figure salary position while vacationing in Grenada with my wife to celebrate our one year wedding anniversary. All my life I’ve been comfortable. Growing up I didn’t want for anything — I had the latest clothes, sneakers, toys and video games. By my senior year of high school I had access to a vehicle 99% of the time to come and go as I pleased. My parents paid for my entire college tuition. When it took me a year to find a job after a college they didn’t charge me any rent. And when I went from making 7.25/hr at Shoe City to 60k/yr with IBM I never looked back. With that monetary success I think I got complacent in chasing my dreams. The last couple months of working for the LA company I started to feel for the first time in my life depression & anxiety. I felt trapped by my salary as crazy as that may sound. I was in a job getting paid, but with every passing day my dreams were fading away. A tipping point came and I asked my wife two questions — are you OK with me quitting my job and do you believe in me? She initially didn’t believe me as it was Sunday night and we were in bed. But once she realized I was serious she said yes and absolutely. I was terrified of submitting my resignation without having another job locked down, but what was more terrifying was not pursuing my dreams. It was deeply effecting me and causing mood swings day-to-day hour-to-hour. I felt like I needed to put the pressure on myself and leave my comfort zone behind.
My wife took me skydiving for fathers day a month before our wedding. The entire experience is awesome. I’d highly recommend it to anyone especially those who say they’d never do it. I wasn’t nervous about jumping out of plane a mile high in the sky whatsoever. The craziest part of the experience was seeing the other divers jump ahead of me. One second they’d be sitting on the edge of the open door of the plane. The next they’d disappear. Will Smith has this awesome Instagram video where he compares skydiving to pursuing your dreams, goals & passion. He discusses how looking down from the plane at death is terrifying and realizing one second later the free fall and descent down is one of the most blissful things you will ever experience. Specifically, he says “God placed the best things in life on the other side of fear”. I jumped.

Did I mention I live in the DC metro area where IT job opportunities are in abundance? I landed a sub-contracting opportunity for Oliver Technology Group a week after submitting my resignation. It’s a step towards making my dreams a reality. And while there’s no guarantee I will accomplish what I set out to do. The amount of joy and fulfillment I have already just being on the path where MY dreams and not someone else’s is at the end of the road is good enough. I’ve never been happier. Also, I plan on framing the first paycheck I pay myself from Oliver Technology Group, LLC.
