The Journey Begins

Welcome to, a blog about goal setting, personal finance and my pursuit of financial freedom. My name is Connor and I am a twentysomething, self-taught software engineer, and now, real estate investor living in Boulder, Colorado.

I moved from Florida to Colorado in 2015 with dreams of transitioning out of the Design and Marketing industry into Enterprise and Consumer Software. Eight months after moving to Colorado and after two years of constant studying, practice and determination to enter a new industry, in 2016, I got my big break and I landed my first software engineering job. I was very fortunate to work with some of the smartest and most driven people that I’ve ever met.

Over the 2.5 years I was at this company, my engineering skills exploded. I quickly leveled up, but I was still struggling to keep up with my car loan, credit card debt, and student loans. Somehow, even with 10% annual raises and performance bonuses, I was unable to develop any significant cash in my savings account.

In November 2018 the company was acquired and myself and thousands of other employees lost our jobs.

With almost no savings, a small severance package and proceeds from the stock in the company that I had been awarded over the years, I still couldn’t afford to enjoy the “fun-employment” many of my teammates were excited about. You might be thinking, “what could be fun about losing your job?” My thoughts exactly.

For the first time, I realized the actual severity of my situation. I had been earning a cushy salary for almost three years and had nothing to show for it. After many conversations with several of my closest co-workers, I found that many of them were a lot more prepared for this kind of situation. Some of them even had $50,000 or more in savings and planned on taking advantage of the winter layoffs for a couple of months of skiing.

I was nearly broke and likely couldn’t make December rent if I didn’t immediately get a new job.

Before the end of November, I started a new job with a 55% increase from my previous salary and over $100,000 worth of restricted stock. A month after my first paycheck, I realized I was now in a very different situation— I had more money than I knew what to do with and I was able to start stashing away $2000 per month. As the weeks went by I found that I wasn’t happy. Not even close. I was miserable.

I had lucked out and narrowly avoided unemployment, eliminated all of my debt besides my student loans repayment and landed a job at a top tech company with excellent benefits, unlimited PTO and a fully stocked kitchen. How could I not be happy?

I was on track to spend the best years of my life, trading the most valuable and productive hours of my days making someone else rich.

The more I thought about it, the more I realized it wasn’t money that would make me happy, but the most valuable thing I had— my time, and I was getting robbed. Until I read Rich Dad Poor Dad, I didn’t know there was any other way. That book changed my life, it opened my eyes to the “rat race” that 90% of American’s participate in every day, but really, it made me restless.

So, this is where my journey to financial freedom really begins. I invite you to follow along with me as I learn to take back my time, my happiness and my future and I will try to inspire you to do the same.