Southern Gentleman Wordsmith

What Happened to That Boy?


It’s been a long time. I shouldn’t have left you.

I’m referring to both you, dear reader, and this little area of the internet I’ve called my own since 2008 when I first registered the domain.

I’ve been sharing my thoughts online in some form (albeit intermittently) since the late-1990s. Some consider me a blogging pioneer. I was able to transition my experience into a few digital media roles off and on, as well.

But so much has happened since I first became active on the web.

I thought I had it all planned: my childhood dream was to become a lawyer when I grew up. I wrote a five-page essay on the subject in sixth grade.

J. Dakar's When I Grow Up Essay
Page 1 of my five-page essay on “When I Grow Up”

While I can’t recall where that aspiration derived, I remember watching Johnnie Cochran during the O.J. Simpson murder trial. I read an article about him where he said, “People think lawyers only do things for money. It’s not about being paid. It’s about doing the right thing.”

To this day, that quote has stuck with me.

I planned to study international relations at Georgetown University after high school. Then, I wanted to earn a J.D./M.B.A. and begin practicing law. But despite gaining admission to dozens of schools, Georgetown wasn’t one of them.

In retrospect, I know why I didn’t get into Georgetown. My mom told me later that she prayed Georgetown wouldn’t let me in because she didn’t want me going far away for college. As I’ve gotten older, I’ve come to understand that. But I admit it hurt to know the woman who brought me into this world prayed to God for something against my wishes. That wouldn’t be her last time doing such, but all the fantastic things I’ve done blow Georgetown out of the water for me. I don’t want to get ahead of myself, though.

Do you remember LiveJournal? That was my foray into blogging in 1999 before I created my first blog in May 2001 as an experiment in personal publishing using Greymatter, the original open-source blogging software. Greymatter relied upon customized HTML templates hosted on one’s webspace. With some coding knowledge, those templates would alter a site’s look, and I often redesigned my website on a whim.

Soon I found other young, gifted people who were doing the same. We were kids, so we could continuously change things whenever the urge to do so hit. We linked our websites, creating natural extensions of ourselves into the burgeoning blogosphere.

We blogged our musings on mundane minutiae. We reviewed books, films, and music we enjoyed (or didn’t). We expressed ourselves regarding whatever was going on in our lives.

Those blogs were digital journals that allowed us to share our words with the world. They also showcased our technical and design skills.

We created online communities for ourselves that helped find others who were like us. It was on one of these community sites, the forums, to be exact, where I met Angel Laws, who created Concrete Loop in 2005.

By the time I graduated high school in 2002, I still had dreams of pursuing law. I hadn’t yet decided where I’d attend college, though. I had applied to many, which was a good thing considering my top choice denied me. Most offered me scholarships to attend, but that didn’t make selecting a school any more straightforward. It should have, especially for those offering full-rides. Sometimes I wish I had taken one of them up on their offer rather than being introduced to Sallie Mae. I know everything happens for a reason, but if a school offers you money to attend, it should warrant strong consideration.

I spent much of the summer after my high school graduation trying to decide on a college. I even remember telling my grandmother that I would love to travel the world before going to college. She and I both had a good laugh at that idea, knowing my parents would have objected, but times have changed.

I decided to attend Birmingham-Southern College, which was an hour and a half away from home. It was also considered one of the nation’s best liberal arts colleges. I majored in political science and pursued a minor in business administration.

During my first semester of college, my grades were in stark contrast to those from my high school career:

  • D+ in The Public Policy Process
  • B- in Introduction to American Government and Politics
  • C+ in Literature and the Social Experience: Gender, Race & Class
  • B in Introduction to Writing

Unlike while in high school, I earned only five As during college. Talk about an eye-opening experience! I had to work hard to revive my GPA following that first term.

I withdrew from school in 2005 following frequent pancreatitis attacks, which involve an inflamed pancreas and severe pain. I’ve heard women say they’d prefer to go through labor than endure pancreatitis. I’ve never given birth, so I can neither confirm nor deny, but I will say I wouldn’t wish pancreatitis on anyone. Withdrawing from school was a blessing, though.

I used that time to write more and figure out the rest of my college career. Grades in my political science courses were less than stellar (I earned a B when I later retook The Public Policy Process). I fared much better in my business courses. When I returned to school, I switched my major and minor. I also earned a Distinction in Leadership Studies before graduating in May 2008.

During my senior year, Angel emailed and asked me to join Concrete Loop. It had become one of the most popular entertainment blogs. By this time, I had decided I no longer wanted to pursue law.

But what would I do after graduation?

I considered going to law school since I knew it could be beneficial in whatever I chose. But why waste time, energy, and money on something that was no longer a dream of mine?

Pursuing an MBA was also an option.

I had spent a lot of time volunteering and working with kids that I considered earning a master’s degree in education. I thought I wanted to become a teacher. But after having spent six years in college, I wasn’t ready for more schooling.

Concrete Loop came along right on time. I had spent almost a decade writing online but never considered it as a career possibility. Imagine that: doing something I loved and someone paying me for it! Before I graduated from college, I was a professional blogger.

In January 2008, I became Concrete Loop’s political contributor. I wrote with particular emphasis on the historic 2008 presidential election, and my initial posts stuck to that theme. Time magazine listed Concrete Loop among the best websites of 2008, which helped me understand that more than the site’s audience was paying attention.

I began covering different topics in my work. I compiled the lauded history spotlight features and conducted album and book reviews. My greatest pleasure, though, came from introducing relevant news items that affected our audience.

I recall insisting to Angel that we create Facebook and Twitter accounts for Concrete Loop to connect with and expand the site’s audience. We would interact with and update followers on the latest content. We began utilizing social media to conduct exclusive contests, giveaways, and celebrity interviews. Concrete Loop was a trailblazer that provoked others to expand their coverage in terms of both content and delivery.

As the Concrete Loop brand expanded, that opened the door for new opportunities and possibilities.

Despite what many have assumed throughout my media career, I’ve never lived in Los Angeles or New York. But an investment in the brand by one of the nation’s largest digital publishers almost saw me relocate to New York in September 2012.

Lauryn called it: “It’s funny how money change a situation.”

Angel and I spent countless hours working on a growth plan for the brand, enabling the company to create multiple full-time positions with benefits. I had lived the 1099 life with Concrete Loop and started working another day job years ago since I was not an employee of the company. Angel negotiated the deal with the publisher, and this venture would allow me to leave my other day job. I’d go from being a freelance contributor who had become her right-hand man to Concrete Loop’s managing editor if my salary was right.

I was hoping for low six figures to maintain my standard of living; Alabama is MUCH cheaper than New York.

Following agreement on the arrangement’s budget, my listed salary was $70,000 plus a $10,000 relocation bonus.

My response?

“Yeah, that’s not gonna work for me.”

Those seven little words in an email to Angel at 4:37 a.m. on Tuesday, August 28, 2012, upended four years and seven months of my work with Concrete Loop. I effectively tendered my resignation.

Looking back now, I don’t think that was my intent. But Angel’s reply a few hours later pretty much sealed the deal (no pun intended):

“OK I’ll let everyone know. Sucks it didn’t work out.”

I published a blog post rather than communicate my feelings to her. Deep down, I was hoping I might be able to continue at least remotely working as I had done previously. But I wrote in the entry: “I admire and support those who are willing to break free from the bonds of boredom or complacency, having recently done so myself with my resignation from Concrete Loop.”

Nothing was boring or complacent about Concrete Loop; Concrete Loop led the urban blogging landscape.

I was hurt because I imagined the brand continuing to grow without me. It took a few weeks to resonate with me. I had a panic attack after realizing that I had missed a wild opportunity and walked away from one of the best jobs in the world. Not to mention, Angel and I had become great friends throughout the years; this completely altered our relationship. Plus, in one of our exchanges following my departure, Angel mentioned my salary would have exceeded hers, and that showed me how greedy and selfish I had been. Instead of the whole “take it or leave it” mentality, I should have been willing to discuss my concerns, and things might have gone much differently. She ended the exchange: “Like I said earlier, it’s a sad situation because we made a great team.”

We certainly did.

When Angel posted “All Good Things Must Come to an End” in March 2014, I shared my thoughts on the topic and emailed her:

Hey Angel,
I know you’ll be getting a ton of emails over the next few days, and I don’t know whether you still use this address, but I just wanted to say thank you again for the amazing opportunity with Concrete Loop.

Thank you for seeing something in me that I didn’t see in myself, and thank you for helping me to see it and encouraging and inspiring me along the way.

Things didn’t go the way either of us planned, but everything happens for a reason. And I know your next endeavors will be dope, as well.

By the way, I hope “indefinitely” means that there is the possibility of a CL rebirth at some point.

But I applaud you for doing things on your terms, as you always have; that trait will undoubtedly serve you well.

I won’t turn this into an essay, but you and Concrete Loop played such a huge role in my life for four years and seven months, and I’ll never forget that. I am forever indebted to you and the site.

I wish you the best in all that you do, and I leave you with one of my favorite quotes: “Success in any endeavor depends on the degree to which it is an expression of your true self.” – Ralph Marston

Peace and blessings,

I’m blessed and honored to have been a part of Concrete Loop!

My work there helped raise awareness for various causes and concerns. I’ll never forget an email I received from the executive director of The Lambi Fund of Haiti. In “Haiti’s Poorest Forced to Eat Dirt,” I included a link to the organization. That post generated 15 times as many emails and donations the organization typically received.

I’ve had opportunities to meet and interview some of my favorite celebrities. One of my most memorable ones was with CeeLo Green. When I asked about a new album from the Southern rap group Goodie Mob, two other members jumped on the phone. I admit I had a fanboy moment, but it pales compared to the interaction with Beyoncé and Solange at Essence Fest that previous year. The only thing I’ll say about that is it left me tweeting: “Those Knowles sisters are trying to kill me tonight!” I’ve visited the White House by invitation, and I shook hands with former President Barack Obama, something I still have a hard time believing!

Angel and I have had some great email exchanges over the years to reflect on things. Still, as I mentioned, our relationship isn’t anything like it used to be. Given how much like a jerk I acted, it’s a miracle we’re even where we are. In one, I mentioned to Angel that I think my actions involved “a little bit of fear of actually having that dream of moving to New York come true. Looking back, I realize I wasn’t ready for that as much as I told myself, you and everyone else that I was.”

It also turns out that despite most of my family being supportive of the move, my mom highly opposed it. I’ve never heard her admit that she prayed something would halt the deal or my move to New York, but after what happened with Georgetown, I wouldn’t be surprised at all.

After Concrete Loop, I needed a change.

I couldn’t apply for a job at a competing outlet, so I figured I might finally be ready for more school. It didn’t hurt that my employer was willing to pay for it. I earned a graduate degree in organizational leadership with an emphasis on strategic planning in 2015.

It’s unreal how much I tried planning my life once upon a time, and nothing went as planned. I realized that my plans cannot and will not supersede what God has in store for me.

During the five years after I left Concrete Loop, I launched a music website that lasted less than three months. I never advanced further than the planning stages for a men’s online magazine. I had even begun writing two very different books but finished neither of them. I also started working on a television pilot.

I thought I was doing what I needed to be doing; writers write, you know? But it turns out that I was doing trying to do too much!

It also didn’t help matters when one of the nation’s largest PR firms reached out to me about representation.

All of this activity occurred before I began to gain clarity on what happened with Angel and Concrete Loop, so I still lacked focus. I felt entitled. I was concentrating on the wrong things. I had lost my way, and I had forgotten my sense of purpose.

For as long as I can remember, writing has been cathartic. I used to joke that instead of attending therapy sessions, I write.

But a few years ago, I considered giving up writing, and it turns out that’s what I needed to do.

In 2016, I reached out to Dana James Mwangi and Eso Tolson of Cheers Creative as I was looking to relaunch When I shared my story with them, they remarked that I make my case and educate others when I write, like I once wanted to do as a lawyer and teacher. I had never considered that, but it made sense. When I relaunched this site in April 2017, I thought I was finally on track with where I was supposed to be. It turns out, I was wrong.

Despite the time, money, and energy that went into the relaunch, I published only three entries before the site sat dormant. I posted an “under construction” message. Little did I know at that time, those words applied to both my website and me.

I stepped away from the web again, took some time to get to know me, and deepened my relationship with God.

Although I have over two decades of experience writing online, it took almost ten years to recognize writing as a career. I still can’t say I’ve fully embraced it as one since I’ve maintained a day job outside the industry with increasing responsibilities. I thought maybe it was time to give it up for good. Something happened in January 2018 when I read Blavity editor-in-chief Lilly Workneh’s letter to the community. In it, she mentioned, “Taking ownership of our narrative is imperative. Independent black media companies like Blavity, Inc. are important.” Those words moved me, and when I saw a job opening for a news editor, I jumped at the opportunity. By then, I had realized my mission, and I wanted to contribute my skills and experience in helping tell our stories as I had done with Concrete Loop.

Lilly brought me on as a copy editor for Blavity News. After five months, I was promoted to senior copy editor of Blavity and its political counterpart, Blavity Politics. I also began editing the brand’s entertainment news and media site Shadow & Act.

With the way things ended between Concrete Loop and me always in mind, I accepted and performed my role at Blavity with gratitude and humility. That only occurred after I was able to kill my ego and find inner peace. I loved working with and helping to develop young writers. So it pained me when my roles and obligations at my other day job expanded, and I had to resign in May 2019.

I shared a farewell message with the Slack channel:

I’m honored to have been a part of Blavity News and Shadow & Act, and I have enjoyed working with such a strong editorial team each day to help tell our stories. The commitment and dedication that you all have will carry you far, and I look forward to watching you grow as writers and editors as well as seeing the brand expand.

I will always cherish my time at Blavity and this amazing opportunity to do what we do; please don’t take it for granted. I also hope you know that every comment and edit I ever made was never an attempt to call you out or embarrass but was in service of helping you become a better journalist. ✊🏼

I may not have spent as much time at Blavity as I did with Concrete Loop. But it will always have special significance, and ending my tenure with Blavity and Shadow & Act was quite positive. I had started to become overwhelmed with managing my workloads at all of my jobs; it was best for everyone.

Little did I know I would soon need that time away from work.

Earlier that year, I had visited a doctor who was filling in for Dr. Krothapalli, my normal nephrologist (kidney doctor), while he recovered from kidney cancer. Isn’t that ironic? He reviewed my lab report and told me I had diabetes, just like that. His bedside manner was horrible, but so was my A1c at 12.5 percent. For reference, someone who doesn’t have diabetes would have a level below 5.7 percent. He prescribed Metformin, and I thought if I took the medication and changed my eating habits, I could get rid of diabetes. After being diagnosed with polycystic kidney disease (PKD) at 14, one chronic condition was enough. I wasn’t exactly shocked I was diabetic as I had been extremely thirsty for a while; it seemed like I could never get enough water to drink. But I was determined to do what I needed to do to cure myself of it.

When Dr. K began meeting with patients again in June 2019, his office asked whether I’d like to see him. Of course, I did! He had doctored my grandmother before her kidney transplant, and he treated my mom and me, who both inherited PKD from her. He had also served as a general physician to my dad and younger brother, so I considered him more of a family friend than a doctor.

It was strange to see him in a wheelchair, but I’m glad I did. Following the fill-in doctor’s diagnosis, Dr. K asked me whether I would mind if he referred me to a diabetes specialist. That wasn’t his specialty, after all. I didn’t and was grateful he offered. Unfortunately, getting on the endocrinologist’s calendar would take months before there would be an opening. However, the nurse practitioner could see me in a few days.

I met with her on the morning of July 3, 2019. We chatted a bit, and then came the tests requiring multiple blood and urine samples. I figured I wouldn’t hear anything until the following Monday with the upcoming holiday. That afternoon, she called and diagnosed me with type 1 diabetes. It’s the less common form caused by an autoimmune reaction in which the body attacks itself and mistakenly destroys pancreas cells that produce insulin. My bouts with pancreatitis in college may have contributed to my diagnosis. We also believe my vegetarian (sometimes vegan) diet and healthy lifestyle possibly held it off as long as it did. This diagnosis changed everything; there would be no getting rid of type 1 diabetes as there is currently no cure. Type 1 diabetes would require constant management of balancing eating, exercise, and all other activities. The Metformin Dr. Fill-In prescribed did absolutely nothing for type 1 diabetes, which would now require me to inject insulin daily.

I soon had frequent appointments with diabetes educators, the endocrinologist nurse practitioner, and nutritionists to get a better understanding of type 1 diabetes. My family attended most of these meetings with me, and I’m so grateful for them taking that time to show their support. The first few weeks after my diagnosis were filled with a range of emotions. I recall one particular instance where I broke down in a session with one of the diabetes educators who trained us on how to give insulin injections. I don’t mind needles, but she mentioned eating a meal before working out along with my blood sugar levels, and it hit me that this disease would forever impact my life. I didn’t eat breakfast before working out since I was used to waking up around 4:30 to do so, which meant I’d have to adjust my entire schedule. It sounds so silly now; who wouldn’t want to sleep in when they had a valid excuse for it? But that hurt because it made me wonder what else would now need to be adjusted. I remember apologizing that I was “being human” as I hadn’t shown any emotion with anyone about all this previously.

I admit I briefly thought it would have been better if I had gone through with my plans for suicide as a teenager following the diagnosis. But I quickly thought about all the extraordinary things I’ve been able to do, not to mention my amazing family and people I’ve met through the years. It just seemed like it would have been easier than having to deal with type 1 diabetes. I mentioned to my nurse practitioner that I’d learned an increased risk of depression exists in diabetics. She responded that the fact that I was aware of it meant I’d manage things just fine. I was somewhat comforted by that, but it also seemed a bit minimizing. She was right, though. Once I accepted my diagnosis and began managing my disease, it no longer seemed like an insurmountable obstacle.

That’s not to say, a year later, that I’ve figured out everything, but all I’ve learned I’m willing to share.

This time last year, I was in a much different frame of mind, but gaining perspective can do that. I don’t view me having type 1 diabetes as a hindrance or a challenge to overcome. It’s merely a medical condition I have, and I’ve made adjustments in my life to handle it as best I can.

Oh, and my latest A1c was 6.7 percent.

I prayed for this. Of course, it wasn’t to be diagnosed with an autoimmune disease; it was to get in the best shape of my life. While I haven’t yet reached my body goals, I am making progress. That goes to show you should be careful what you ask for because you might get it; just ask my mom. Ha!

In all seriousness, though, I had to humble myself and allow God to work. So often, we try to act as if we have control over a situation, but we have none; we’re not God. There’s so much power in recognizing that. I’m sure you’ve heard the saying that “God doesn’t give us more than we can bear,” but sometimes we’re given more than we can handle, but there’s nothing God can’t.

I can do all things through Christ which strengtheneth me.

— Philippians 4:13

So much of our carefully curated online existences and personas focus primarily on the achievements we accomplish. There’s absolutely nothing wrong with celebrating our wins. There’s also no harm but perhaps great benefit in sharing our challenges or professing the lessons learned from losses and setbacks. To do so requires a certain level of openness and vulnerability that we have to be willing to admit to ourselves and others.

I needed to learn humility to return to the web and share all of this, and I hope my doing so helps you in some way. Whatever you’re going through, keep going. Even when it seems like all hope is lost, you can’t give up.

My hiatuses allowed me to get my mind right and focus, and they’ve been such blessings. The internet helped me figure out who I was a long time ago, but it required me to step away and discover who I wanted to become.

I don’t intend on this becoming a diabetes blog. I’m sure some entries will involve it along with any and everything else that impacts my life in some way, though.

I hope you’ll come along for the ride; it ain’t where I been, but where I’m ’bout to go.


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Southern Gentleman Wordsmith