My Thoughts on Career Development

Transitioning From A Low Paying Hourly Job to IT Roles (Part One)

Heads up…This is not a story about getting rich quick and there were a lot of sacrifices made and rejections along the way.

It was only about 10 years ago when I was working at the front desk of a hotel in Fairfax County, VA and making $11 an hour ($12 overnight). I was taking the long route to get my 4 year degree and was barely making ends meet. I moved up to Northern Virginia from Virginia Beach and was still in shock at how high the cost of living is up here. It was a constant struggle to make sure that I had enough to pay the rent each month as well as keep up with the utilities. I counted every dollar I had when trying to make a decision on which groceries to purchase for the week. It was tough having to choose work over partying in my early twenties but I had no other option. I knew I was smart enough to live comfortably up here but I was so far behind and it felt like I could never catch up. I went to school during the day and worked in between classes or overnight.

During the quiet, late nights at the hotel, I would read tons of business articles in hopes of finding a way out of my current situation. I would look on Craigslist for higher paying jobs and anything that seemed more like a true career opportunity for me. The hospitality industry can be fun and you can learn a lot but it was not going to be my final stop in this journey. I saw a relatively low ceiling for what I could make if I stayed and it would be a long grind to make maybe 50 grand a year. In an area known for its wealth, I knew I could make more. I eventually left my hotel job after a couple of years and transitioned to working as a STEM instructor. I was able to make about the same amount of money but I was working less hours. I made between $50- $135/class depending on the amount of kids enrolled and a few other factors. That went well for awhile until I could no longer tolerate the toxic small business owner who began to constantly mistreat the people that worked for her. I quit that job without a plan (I don’t recommend that approach) and eventually worked at a bar for a bit before finding a job my next salaried job.

I finally got an opportunity as a technical trainer after searching job boards day and night. Keep in mind that this opportunity did not fall into my lap and I faced a lot of rejection from other companies beforehand. I had an Excel spreadsheet of all of the jobs I applied to and the rejections just kept up piling up. I didn’t give up and my persistence finally paid off. I started with a salary of $40,000/year and I’m not going to lie. It felt great at that point in time.

picture with Tymon and Will

Lunch break with Tymon and Will in D.C. Will and I were both technical trainers at the time.

Working as a technical trainer can be tough and very exhausting. You are talking nonstop for 7 of the 8 working hours of the day and sometimes you would have to commute to client sites that are far away and sit in hours of traffic. Don’t get me wrong…there were some great benefits as well and I made sure to take advantage of them. For one, I was becoming an expert in the Microsoft Office and Adobe suite as well as working on my soft skills as I taught these classes. The most important benefit of being a technical trainer is that they allowed you to take certification exams for the classes you taught for FREE! I’m not sure if all training companies do this but I recognized the immediate value in free certification exams. I knew I could boost my resume and open the door to future opportunities if I could pass as many exams as possible while working there. So that became my goal. I took every Microsoft Office certification that I could within a 9 month time span. I would say that I passed 6 or 7 exams during my tenure. Once I could no longer take the wear and tear of being a technical trainer, I landed a role that was a mix of technical trainer and business analyst. The best part about this new role was that I received a pay bump from the 40k I started at as a technical trainer and began making $50,000/year without having to do the extra traveling to client sites all across the DC/Maryland/Virginia area. What truly helped me get my foot in the door was a friendly recruiter and the fact that I had a certification in one of Microsoft’s most popular tools, SharePoint. The non-profit that I was working for was rolling out Microsoft 365 and they needed some assistance getting the rest of the staff up to speed on the new Office suite.

Stay tuned to see how I was able to branch off from training to project management.

Financial Freedom and Information Technology

Let me start by saying you should definitely listen to the podcast episode I linked in the newsletter. Not only is it posted on the web but you can find it on Apple Podcasts and Google Play as well. That makes even more convenient if you’re on the go.

Before I made the switch to IT, I was working part time hours while trying to finish up college. I was averaging around $30,000/year, which doesn’t get you far in Northern Virginia. I knew it was smart enough to make a lot more than that but I had to prove it to myself and everyone else. In five years I was able to go from a technical trainer making $42,000/year to a project manager making $140,000+/year. I’m telling you all of this because if I can do it, then you can do it too. More money isn’t always the goal but it does allow you the freedom to do what you truly love.

Kyle Hollis