Part I

Here’s the story behind my social media handle @decafquest, which I don’t think I’ve written about before.

At some point, I was teaching up to six philosophy courses per semester spread across two different universities. That meant I was teaching around 18 hours of philosophy a week. It wasn’t that bad, really.

To keep up, and mainly because I enjoyed having coffee during class, I was having no fewer than three double espressos a day, in addition to the liter of mate tea (yerba mate) I would have in the morning before I left the house. Sometimes the number of espressos would go up to five.

Needless to say, there came a point where my nights were sleepless because of all the caffeine in my blood, and my heart was beating faster than the Red Bull F1 cars.

I had to stop. I quit coffee cold turkey for a few months but kept my mate tea routine in the morning. Then I slowly incorporated decaf but was only having one espresso a day, and some days I’d go without having any.

That’s only one side of the story.

The other side is that during that time, I was also getting more and more disillusioned with philosophy as a discipline, and more particularly the way academic philosophy worked.

The field is extremely competitive, and because of the way the system is built, many professors end up self-absorbed because they’re trying to stay in the race for as long as they can.

I was starting to realize all this wasn’t really my thing because I was more interested in a laidback approach to philosophy. One that didn’t require that I take things all too seriously and that gave me enough leeway to explore things in a more playful manner.

To many, this sounded exactly like a decaf attitude, devoid of ‘substance.’

During that time, my wife was trying to get me to join Twitter. I was not convinced at first because the entire experience was overwhelming. Eventually, I budged, and in hindsight, thankfully so, and decided I was going to create an account.

What nickname should I use? After giving it some thought on my 15-minute walk from the university back to my place, I decided to choose Decafquest because it captured the spirit of the laidback attitude I had while exploring and teaching philosophy.

The ‘quest’ element of Decafquest also accurately portrays the transformation of my mindset.

I wanted to explore new terrains and learn more about others without the pressing need to find a particular answer or concrete goal. I was simply curious, wandering around, and learning new things.

That’s why I love discovering more about other people’s journeys, whether through autobiographies, documentaries, podcasts, or YouTube videos. And that’s partly why I also love chatting with others on my Marketplace Discussions podcast.

Part II

What interests me about other people’s stories is the common element that underlies their experiences. The goal isn’t to mimic how to get from point A to point B by following the same path, but to find shared experiences, no matter how different, that might help us on our personal journey, our own quest.

In light of that, meet Jordan O’Connor, whom I recently had a chat with on the podcast. An engineer by trade, he graduated with over USD 200,000 in student loans. At his first job, he was making USD 80,000 a year, which was not enough to pay back the overwhelming debt and make ends meet.

Jordan reflects on the high tuition he paid in exchange for an electrical engineering degree. Was it worth it? To a certain extent, in his case, he affirms, it was.

Before joining college, he lived in a small town where there were more cows than people. In college, Jordan was exposed to a wide variety of subjects that he hadn’t seen before. He learned about AI, coding languages, and a great deal of other topics that would later prove to be helpful.

Jordan’s experience as a full-time employee at the multinational tech company Corning Inc. was not bad either. In fact, he gives two reasons why he enjoyed his 9–5 job:

• working at a high-tech firm gave him the chance to be exposed to state-of-the-art equipment and technology,
• his job required a lot of backstage tinkering, which meant that he didn’t have to deal with clients.

The only downside was that it would’ve taken him a lot of time and effort to secure a decent salary. So he knew that he needed to come up with a different plan if he were to pay back his loans.

Jordan embarked on a quest of his own, building a diverse set of skills to start a side hustle. These included marketing, SEO, Facebook ads, app development, database, and backend-frontend integration.

After dabbling with several projects, building and refining a wide range of transferable skills, Jordan stumbled on what would become his most successful endeavor to date.

In an attempt to help his wife save some time carrying out transactions on Poshmark, an online marketplace where users can buy and sell new or used clothing, shoes, etc., he ended up developing an application that solved the problem efficiently. The application was so good that his wife’s friends, and later on, other Poshmark users were inquiring about it.

Jordan never thought of this small project as a business because he was trying to solve his own problem. But the interest many Poshmark users displayed in his application made him realize that there might be a profitable business idea there. After a series of iterations and feedback, he launched Closet Tools as a paid subscription Poshmark automation tool.

The app gained traction, and at its high point, it was generating USD 45,000 … a month!

Now in hindsight, Jordan regrets that he didn’t double down on it when it was growing fast. He explains that he always thought of Closet Tools as a side project that might stop generating revenue at any moment. Jordan divided his attention and effort across a variety of projects that he was pursuing in addition to Closet Tools.

Could he have done things differently? I asked him. His response was affirmative. He could have spent all his effort on Closet Tools when the business was off and showing signs of more growth.

The idea would have been to grow the app to a point where he could have sold it for one or two million dollars. Such a hefty sum would have given him enough runway to dedicate time and effort to exploring new ventures.

Due to his aversion to high-risk, Jordan believed that he needed to constantly seek additional income streams. As a result, Closet Tools subscriptions plateaued for various reasons. At present, Jordan is enhancing the tool by incorporating more features in an attempt to rekindle its growth and sell it this time.

Over the past few months, Jordan has also been tinkering with a new project on the side. He has been offering SEO consultation services. After a period of trial and error, he had enough information to start offering a cohort SEO course which he began developing recently.

Final Reflections

I began this article by sharing the backstory of my social media handles. My intention was to emphasize the quest aspect of each of our personal journeys. This is what intrigues and captivates me in my conversations with people. We are all on a journey, seeking better opportunities, businesses, projects, lifestyles, and career paths. We are also searching for meaning in life, new and unforgettable experiences, and opportunities to form new connections.

Jordan’s story embodies one such quest. In one way or another, no matter how different our paths’ conditions and circumstances are, there is a high chance that something from the journeys of others might resonate with us, strike a chord, inspire us, and give us an idea or two that could help us in our own pursuits.

Tune in to the episode at the following links:

Audio format

• You can find me on Twitter @decafquest.
• Personal website.

Originally published at https://decafquest.substack.com.