My wife Jen and I started our company, R. Maestas, at the peak of our career unhappiness in 2018. It was four months before Jen began working part-time with our first client and seven months before we both took the leap in making the company our household’s sole source of income. We knew that working traditional jobs in our respective fields meant we’d each spend 40+ hours a week behind our desks, broken up by brief stints of PTO, for the rest of our working days. It was disheartening for us to realize we wouldn’t be able to get out and explore the world until we were almost done living in it. Our true ambitions were simply to do the work we loved, all while living the lives we wanted to live. While our work focuses are vastly different, Jen being a graphic designer and I being an IT consultant, we discovered significant overlaps in terms of everything required to support our respective practices. We are both providing professional services, and we bill hourly or by the project. Makes sense to take the leap together, right? So we did. A key difference was evident in the early days as Jen was performing work for clients across the country from our home, and I was spending full days commuting and working in clients’ offices. Fast forward to 2020 and we still had mostly the same routines. That all changed on March 16th, when I stopped going into offices, and on June 10th, when I forfeited my last in-office desk. I clearly remember sharing the news with Jen, along with the outpouring of emotions that followed. A wide smile, shaken by a quivering bottom lip, tears in the corners of her eyes, and the eruption of a joyful chuckle conveyed what words could not.; pure bliss. The possibility was now real for us to do the work we wanted to do and be unrestrained by a requirement to go into an office.
Wow!
That portion of this introduction was actually written two years ago (almost to the day). It was never posted to this blog because, at the time, starting a blog was at the bottom of an awfully long “to do” list. Our company was experiencing paradoxical growth. Between increasing engagement with existing clients and responding to a steady influx of referral business, we were at our limits serving those clients, and we had almost no capacity to pursue or take on new work. Both 2021 and 2022 were excellent years on paper, and we were operating at a breakneck (probably unsustainable) pace. Normal activities for a burgeoning company were neglected in that period, like scaling the business to meet growth, marketing, contributing back to the community, and pausing for reflection.
Learning, and returning to fundamentals
While our company’s story may have begun in October 2018, it has a prologue: This is my half; perhaps Jen will guest-contribute hers in the future. I was raised in a traditional, supportive household. I experienced discipline, rigor, and love from parents, who are owed a great deal of credit for any success I experience the rest of my career. My mother stayed at home and sought the best for my brother and me. We were provided charter school primary educations, summer camp experiences, and had swim team careers that culminated in state qualifications. As kids we learned to ski, fly fish, fix cars, and help relatives do general maintenance around the house. My dad gets the credit for most of that last sentence, along with blazing a career path that was the Northern Star for my own early career. During my senior year at Arapahoe High School, mom guided me into Littleton Public School’s concurrent enrollment program at Arapahoe Community College. Thanks to the generous taxpayers in my home city, I was able to begin accumulating college credit without paying tuition costs while I was still in high school. It was hard work balancing a part-time job, two-a-day swim practices, and finishing the high school courses I needed to graduate. College expenses lay ahead, but at least I didn’t have to write any checks to the bursar’s office during that time. All too soon, this was going to change. It was mutually understood that after graduating high school, my parents would still provide a roof while I was in college, but continuing my education meant I was on the hook to pay for it on my own dime. I did my best to maintain a can-do attitude. After all I had worked hard to finish high school strong. Still, having grown up in suburban Denver among mostly upper-middle class families, this felt harsh at the time.
Paying for college was one of the most formative accomplishments of my young adulthood.
Based on everything I knew as a class of ‘09 high school graduate, who wanted a management job in IT, going to college was mandatory. Since I did not qualify financially for a federal grant (more on this in a future post), and ideologically wanted to avoid taking out any type of loan, student or otherwise, I needed to find a non-traditional way to make college affordable. Enrolling at a traditional public or private four-year school would have been cost prohibitive. Since I had taken community college classes in high school, I only needed to spend four semesters with a light course load to finish a two-year degree. Enrolling at a community college helped with minimizing costs, but I still didn’t have enough savings to afford tuition. No-need work study funding was a possible option and I applied. This allowed me to work part-time on campus, focus on my studies, excel scholastically, and earn academic merit scholarships. Spending two years working hard at the community college led to a windfall in the form of a full-ride scholarship, enabling me to finish my degree at the University of Colorado Denver Business School. Studying Information Systems at the business school, and eventually graduating cum laude, cemented my career direction. I had taken the first steps in achieving my career goal of one day becoming an IT manager. Finding a solid internship my senior year eventually led to a full-time IT job, which involved supporting a 20 site/300 seat enterprise as part of a three person team. The job challenged me to learn and adapt quickly, and my employer generously paid for several professional certifications. After taking a year off of school and making learning on-the-job my focus, I decided also to enroll full-time in online graduate school. The University of Alaska Fairbanks School of Management conferred my master's degree in business administration during the Spring 2016 commencement ceremony, and during the next year I was married, bought a townhouse, and accepted my first IT management position.
Starting the business
That first management job was, in a word, humbling. It might even be a stretch to call it a management job, as I had only two direct reports and a handful of vendors to manage. The list of responsibilities was extensive, as were the growing IT needs at that mature organization. Training junior staff was equal parts rewarding and time consuming, but at all times it was necessary. I sought to strike a balance between investing energy in developing my team and finding creative ways to stretch an inadequate budget to cover an unsustainable mountain of technical debt. Working in management was a career goal, but even with a graduate level education and professional certifications, I had so few years of experience I was unqualified on paper for many management positions. My pivotal point was switching to consulting. The change fast-tracked me into a pseudo-management role where I would be working with real IT managers, helping them guide and execute strategic plans. It was a process set in motion about five years ago, and now working as a consultant is what I see myself doing for the rest of my career. Starting and running a consulting company is a topic I will cover in future posts. In addition, my blog will provide insights to the ways of thinking and processes based on experiences from my forever job, including the forthcoming experience of growing our company. This blog is also a symbolic reminder to balance marketing and promotion efforts with operating a business, to take time to pause for reflection, and to contribute back to my professional community.
