After dedicating two decades to the information technology industry, I decided to resign from my position as a Software Architect four months ago to pursue my creative aspirations. Self-employment, and to pursue my art was the goal. I now engage professionally in photography, filmmaking, and writing, utilizing these media to share compelling stories. Clarity of goals and aspirations is essential to such a leap of faith and acts as a guiding beacon.
Newfound Freedom, and Responsibility
In a previous article, I discussed my transition from employment to self-employment and explained that I did not come from a privileged background. My achievements are the result of diligent effort and perseverance. It is imperative that I maintain accountability for this reinvestment of my accumulated savings of the past sixteen years, both to myself and to my loved ones, as I embark on this significant shift. Similar to the initial period of euphoria experienced by newly married couples, the novelty of newfound freedom has begun to settle, along with the initial excitement generated by my inaugural YouTube video discussing my decision to resign from my job, which inadvertently placed me in the public eye.

Analysis and Progress
In my previous life as an employee, my team and I conducted regular retrospectives every two weeks to assess our performance by identifying what went well, what did not go well, and how we could improve and realign with our business objectives and vision. It is vital to continually challenge the positive and negative aspects of one’s performance to maintain clarity and accountability.
Before presenting the findings from my retrospective analysis, I must note that I have yet to actively pursue opportunities within the local market for commercial video, film, and photography. My primary focus has been developing my YouTube channel, engaging in writing, and designing a photography course I plan to offer soon. I have done only one paid photoshoot. My objective has been to cultivate an online community on and off social media platforms while adding value through disseminating knowledge. Additionally, I have taken proactive steps to venture beyond my comfort zone by attending events tailored for creators and independent filmmakers. These experiences have allowed me to contribute, learn, and expand my professional network. At this stage, I am resolute in my desire to operate independently. I am not currently seeking to engage in commercial client work.
Of my total living expenses, 13.34% were spent on my creative work, including Adobe subscription, music, travel fuel, camping and nature park fees, and food while traveling.

What Went Well
I posted a YouTube video about my decision to resign from my job, which brought my subscribers from 300 to 4,000 and helped my stagnant Instagram account surpass 2,000 followers. This uptick also led to nearly 400 newsletter sign-ups and boosted my confidence, motivating me to seek more growth opportunities.
Adorama and other magazines in South Africa approached me to contribute written content, which provided an unexpected income boost. Additionally, they allowed me to develop as a writer.
Joining the filmmaker community, Cinemate allowed me to connect with local creators, present my story, and screen my short film on the big screen. Engaging with others and cultivating a sphere of influence is an important aspect of my work.
I also collaborated with a renowned cyclist and photographer who ended his cycling journey down the length of Africa here in Cape Town. This collaboration created a meaningful friendship and unexpectedly led to paid writing opportunities.
I’m completing a photography course for beginners with nearly sixty episodes and am developing a market strategy for its launch.
My creative income makes up about 12% of my total expenses. Combined with revenue from various investments, these sources cover nearly 66% of my overall costs, which is more than I expected.
I’ve stayed focused and organized, regularly reflecting with my partner and close friends to keep my goals in sight.
Despite working long hours, I feel fulfilled and content.

What Did Not Go Well
The initial excitement and expectations surrounding my first “I Quit” YouTube video diminished after reaching nearly 64,000 views, the reasons for which remain unclear to me. Subsequently, I produced several additional videos on YouTube, which received a maximum of a few hundred views each. While the initial decline was disconcerting, I have tried to liberate myself from the impetus of catering to the YouTube algorithm. Moving forward, I intend to create more content that addresses searchability and aligns with my passion projects. Importantly, I aim to remain undeterred by viewership numbers. To date, I have responded to each comment and addressed every email from my subscribers. I aim to cultivate a community founded on trust, wherein I share my knowledge while learning from others.
Many Roles to Fill
As a Software Engineer who led projects, I was accustomed to working with a team where everyone had specific roles and responsibilities. However, in my new endeavor, I quickly realized I had to take on all those roles myself. I became the business’s writer, narrator, planner, videographer, actor, marketing specialist, video editor, administrator, accountant, and more. After the excitement faded from my video, I understood I was on my own and needed to remain fully invested in this endeavor with my eye on my goals. I need to turn everything I used to say I would do into actionable steps. It is time to make it happen.
I feel a constant urgency to align my income with my expenses. The animated discussions with my wife about seeking commercial work opportunities that I am resisting recur every few weeks. I appreciate her holding me accountable; she is my strongest pillar of support. However, I remind her I have committed to giving myself two years of self-employment to establish my business, and thus far, this has stayed the same in my thinking.

What I have Learned
I use my whiteboard to once again refer to my objectives, seek clarity, and prioritize my goals. This helps me focus on working in a priority order. Because tackling everything simultaneously leads to confusion, burnout, and chaos.
I keep my plan in mind: If I fail in YouTube, writing, or building a community for my photography courses, I will reevaluate and pivot. Self-employment as a creator can take on many forms.
Although I have been going to the gym and hiking regularly, I still eat comfort food too often. I must strive to maintain healthy eating habits.
In the past four months, I have reduced my coffee expenses by half – a real sacrifice! However, homemade coffee has reached new skill levels.
Final Thoughts, For Now
While I receive support and encouragement from those around me, I recognize that this road of self-employment is ultimately my own. I must continually remind myself of the reasons I have embarked on this path, as there are moments of uncertainty. Money is a tool that is secondary to the vision one holds. When genuinely committed to a purpose, financial success will naturally follow, opportunities will arise, and growth will happen.
Creative initiatives are a combination of the heart plus skills. Every effort made with a goal in mind pays back in its own way. Although success is subjective and not easily measured, I need to be market-smart and lay the foundation now to make my journey sustainable and enjoyable. For now, I keep this quote from the great Rumi close to me, “Your heart knows the way. Run in that direction”.