One thing we need to change in our Black community, Black culture is the older Black folks don’t want to share the painful life lessons with the younger generation. This is one of the things that frustrated me is older Black folks act like it’s too painful to bring up and get into that hushing bullcrap. Nah, I’m tired of us brothas and sistas repeating the same mistakes as our older generation, and we just recycling the same problems in our lives, generation after generation. This got to stop and we got to realize the biggest investment we give the future is not to let them repeat the mistakes we made.

I personally made a lot of mistakes but that’s not the real pain point in my life. My biggest pain points are the biggest regrets I have in my life. Regrets are worse because you were at a decision point in your life or had the ability to choose and you made the wrong decision. Here is the thing, especially with Black folks; you keep making poor decisions and choose the stupid option it will have a massive impact on the future quality of your life. The biggest regret in the Black community which I cannot choose due to being a man – a young Black woman getting pregnant by a bum-ass, broke-ass brotha is the #1 poorest choice and biggest regret in our community; nothing tops that. The #2 biggest regret is Black folks choosing to worship Jesus in the image of a White man – this will totally mess your life up and will have you end up lying to yourself and unfulfilled during your midday to sunset stage of life.

I cannot complain about my life – it’s been good and I enjoy every day today due to making a lot of decisive decisions and having little to regret. But there are some regrets that could have made me better, could have made my quality of life better and would have put me in a better position than where I am right now. And this is what I want to share with the younger brothas and sistas and hope they don’t repeat my mistakes.

This is not a made-up listicle, I really experienced life and this is my biggest regret that I feel to this day I hope young brothas and sistas can learn from:

Biggest Regret: Not Keeping a Bond with My Non-Black Friends from College Years

During my college years, I had my Black friends that were dogmatic because I was trying to live that “Black college experience” but when it came to studies, common interests and meeting and friendly people I had a lot of foreign students from Asia or Europe or Africa, a lot of biracial fine sistas who hung out with me while the sistas were acting like queen bees and fellow Army and military veterans who went to college after serving just like me. But I was drawn into Black folks telling me we all we got and it’s us versus them and other xenophobic stuff. When Black folks saw me hanging out with one of the non-Black foreign students like a cute Malaysian girl I still remember her, they look at me and her crazy.  

To this day, I hated and regret that I allowed myself to be drawn into an artificial “Black identity” community on the college campus. These same Black folks weren’t in the same classes I was, weren’t in the computer lab like I was, they were goofing around at the student common areas trying to appear popular and holding down the gathering spot. The reason why I regret this so much is because I could have had global friends right after college and could have visited the Taiwanese guys in Taiwan visited the Malay girl in Malaysia and Indian friends in Indian and that biracial chick we could have been camping at an EDM festival in Colorado. I had to build up a global collective after college but I had a lot of friends in these places and I wished I didn’t let my non-Black friends from college go like that where I went back to Chicago, back to the same stuff, different day negativity.

Biggest Regret: Not Moving Out on My Own After College

When I graduated from college, I went right back to my hometown Chicago and many of us did the same thing – move right back to our parents’ house. It was understandable, we didn’t have a job/career lined up for us and we need a place to stay and relied on our parents to support us. Going back to where you from after accomplishing a feat like graduating from college is a massive mistake. Because you going back to the place you should have progressed from.

I went back home and hooked up with people I grew up with who didn’t go to college. They treated me like my college years were just “being away” from them. They also treated me that way after I left the military and came back home as I went to some “cool camp” – nah, I was doing real stuff in the military and studied all night on final exams in college but they didn’t appreciate that. What I should have done is what eventually happened – I moved out of my home and moved with someone who I went to school with who was handling their business like me. We weren’t roommates because I found my own place really fast but I want to tell you something about this event.

This was 1996 and I had a wealthy entrepreneur family that wanted to learn about my dotcom skills and work with me. I didn’t have a car. None of the hood folks wanted to help me out – it was my college alumni who drove with me and we went to his mansion and he was there with me as we both talked to the wealthy entrepreneur with 11-figures who was my first angel investor in my Internet startup business.

The regret is I wished I had done a roommate arrangement with folks I went to college with who had the same ambitions as I had. I wished I could have kept in touch with them and we got a flat in New York or Los Angeles and most of them had flats in New York or Los Angeles and if I would have moved with them, hustled hard in those markets, I would have been better off in my 20s as a young man versus being back in Chicago around the same folks I grew up with from high school trying to relive that high school stuff.

Biggest Regret: Not Paying Myself First After Getting a Paycheck

When I moved out on my own and got my first job, I don’t know what was happening with my paychecks where I had only $40 after paying for anything and some cases, just got $10 after paying everything and it’s Saturday morning after payday Friday and I got to work another two weeks. I would literally have just an 8 pack of hot dogs, a bag of rice, and a can of green beans and mix all that up as food for a week and swap the rice for a macaroni and cheese box. Not going to bring up the box of Tuna Helper either.

What I should have done when I got paid was first take of my well-being first. I should have a better diet because today, I know it is cheaper to cut up and freeze chicken breasts and sirloin steaks and fish steaks the the butcher at the shop would done the cutting for free at the grocery store if I ask them to. That’s meat prepping is not even $20 in today money and would have last two weeks. Getting bananas is cheap about 20 cents per banana, one or two potatoes to cut up and boil, lettuce, carrots, one cucumber that can be used to diffuse in water for cucumber water – all of this is cheap to create and healthy to eat for two weeks. But I was raised ghetto and corner stores and only knew hot dogs and rice and a can of green beans.

Second thing is I should have planned more mini-trips for myself such as save up to visit the Art Museum or dress up and go to North Michigan Avenue and catch a movie or a play at the Chicago theatre and took a girl I went to college with. And once a quarter, pay to see a concert like Maxwell or Kem and bring a sista I went to school with as well or from work. I have eventually done these things years after college but I regret I did not live this lifestyle early on because I would have engaged in a better self-rewarding quality of life.

Regret: Not Visiting Tokyo or London in My Twenties

This is a major regret I don’t want any young brotha or sista to repeat – I would like all young brothas and sistas do real international travel and not some group travel on a cruise ship or island festival. I mean a true solo journey to an international urban spot like Shanghai or Paris and do it by yourself and plan the trip. Had I done this in my twenties, my quality of life and scale of progress would have been greater than where I’m at now.

What I quickly discovered in Latin America, Europe and Asia is the number of sexy Black/Brown/Asian women of different quality and caliber than the ghetto crap I was putting up within America. I did not realize the brothas were more supportive and more willing to share high-caliber knowledge overseas. I would have moved and worked in Singapore, did a stint in Paris or in London as a young Black person just for the global exposure but I will be honest with you – if I went to Bogota or Panama City as a young Black person I would have come back with a wife because those women and that life down there and setting up a house with land, these are the things we not realizing as options for a young brotha or sista.

You young brothas and sistas I meet a lot of you at the International Wing at the airports while other brothas and sistas be at the Spirit Airlines and Southwest Airlines terminals traveling domestically. And you brothas and sistas do not realize the joy and happiness these international brothas and sistas in their 20s are enjoying their life and seeing things fresh and new and away from toxic racism and toxic Black identity dogma – especially sistas who don’t have to deal with ghetto Black masculinity.

Had I visited Tokyo and London in my twenties and lived there even for a month or teaching a class for a year, I would have learned a lot at a young age. I did not get involved in international travel until I was in my mid-30s but I wished I did this earlier and hope you young brothas and sistas learn from my regret.

Regret: I Wished I Didn’t Hold On to That One Girl and Just Stay Forward

Here is something that I made sure my own son does not repeat my mistake. I had a girl from Chicago I had known for nearly 35 years. We first met as teenagers on the State Street bus as I got on at 76th and she got on at 47th headed to downtown and she sat in front of me. I got in touch with her and was chasing and pursuing her and she let me call her and let me talked to her – that’s the important part you need to understand.

Notice I never said she called me, she talked to me and I listened, she came and visited me – noticed I never said any of that. See, it was all me being fascinated with her and filling my head up with this romantic novel story of me working hard to be a good, stable brotha to be with her. And I spent 35 years still hoping to make something out of this woman.

Long story short – the year 2021, she contacts me and want to visit me and I decided to accommodate her. She came down and what I saw was the truth and reality – a ragged ass aged woman who came to me all broken and torn up and this is when she finally felt like she wanted to see me, not when we were younger. But think about something – the 35 years.

She wasn’t as bad as that Malay girl I met while in college, she wasn’t as bad as that Indian Army chick who stayed in the barracks across the yard on base. She wasn’t as bad as the female cousin of a friend at college who I had a one-night stand with, she wasn’t as bad as the women here in Atlanta I took off the strip pole or the college girls I dated while married going to see the Atlanta Hawks and a co-worker noticed I’m not with my wife – she definitely not bad as the Japanese and Afro-European women I been dating recently either. But there is one more thing.

When I took a break (ok, I was on academic suspension for below 2.0 GPA) from college between sophomore and junior year and went back to Chicago. As I was looking for a job, I ran into this Puerto Rican woman who looked like one of Prince girlfriends several times on the train and me and she just clicked and she had a small waist and big hips and beautiful face and glow – her name was Gloria and she was my age. We had so much fun together that summer. I met another lady during Freaknik 1994 in Atlanta and we still in touch to this day and she is another beauty that we clicked at Piedmont Park, I even met two women from Howard University at that same Freaknik 1994 I later on actually visited.  

Here is what I want you to understand – I met all those fine beautiful women throughout my life but I allowed only one woman to rent too much space in my head, the one that didn’t call, didn’t come through because of that fantasy long-term love I held on too. This is a major regret in my life.

You want to know what happened because it was several weeks ago. She came here, but she couldn’t compete with the Atlanta and New York and Virginia and Louisiana sistas all around us as we went out, not even close. She never offered anything and I treated her like royalty. Well, guess what happened? After all that, my birthday came up. On my birthday, the Brooklyn lady I dated for years in the 1990s called me and wished me a happy birthday. My chick from Japan reached out to me via Line and wished me a happy birthday. I had Indian women, women from college, even Latino women on Buford Highway called up and wished Papi a happy Birthday. But I have not heard from that one lady from Chicago I held on to inside my head for 30+ years. I dumped that ungrateful non-calling woman immediately and blocked her and will never see or speak to her again in my life.

My regret is holding onto some past when I was meeting so many fine sistas each day a brotha woke up and went out on that hunt. Always face forward and focus on that next person ahead of you, if you ran into someone and they don’t show up again, just keep looking forward and moving forward – screw that high school chick or dude you brothas and sistas still got fond thoughts of and keep moving to the always new and fresh ones you haven’t met yet.

Last But Not Least Regret: Not Cutting Off People Quick Enough

This is one of the biggest mistakes we going to learn as we progress to new levels as a Black person. You going to find out that you should have been cut people out of your life once you saw they were one some non-value worthless BS. What you going to be blinded by, is a false sense of loyalty.

There is a piece of wise sage advice on Wall Street when it comes to investors – don’t try to pick winners, pick the obvious losers, and get rid of them out of your portfolio. The winners already know how to win and take care of themselves, all you need to do is recognize the losers and cut them out fast to prevent them from offsetting your gains.

I had fraternity members still around while I’m in my 40s and 50s talking up who is doing better, not realizing I’m richer than who they bragging about and my friends from the same school now doing stuff in Hollywood and I got ex-girlfriends, two of them with a couple of franchises in a whole USA region who went to school and these jokers I have of a fraternity d*ckriding one Black dude from another fraternity not realizing I’m doing better – actually they probably do know but don’t want to support me or that fact about me. I don’t got time for this crap anymore and too old to entertain this and cut them off.

I had family members who want to play sibling rivalry and I’m not even thinking about them as I have my own son to raise and raising these kids from single mothers I’m dating here in Atlanta – yall know I love raising some other dude baby, right?  I go back to Chicago and they talking mad stuff about me and I haven’t seen them in over a decade and wonder where is this BS coming from? I immediately cut them off and realize some of my own family never ever supported me, even as a kid.

I had a lot of fake friends trying to be cool with me but they not contributing anything of value and want me to spend my money to hang out with the crew or whatever. Trust me, I learn to cut them off because they were just probing my money and my hustle to talk to someone else about me. Then I saw co-workers this way, trying to figure out how I’m handling my money because I have programming skills – you know what they would do trying to be slick? They would contact me the Thursday before payday Friday and ask me to go out to an expensive place to dine to see if I always had extra scratches and not living paycheck to paycheck – I read them fast and cut them off quick as well.

I learned to cut off stuck-up chicks real fast because I don’t play that mess. No chick better not come in my range thinking I’m in her world to be ranked by her as worthy or non-worthy. I work hard for mines and I got access to the chicks I like and don’t have dating problems. So the minute a woman even present herself as some conceited snob, I’m cutting her ass off real fast out of my life even if it was a 5-second encounter.

I regret not having this attitude as a younger person. Had I got rid of the losers quicker, I would have appreciated the winners in my life more. What happened is I let the losers take over the winners in my life and I found myself tolerating the presence of losers – from family, from the fraternity, from fake friends, and so on. Life was not happy during that period these people have taken up space in my life. It was COVID-19 that hit me so this was recent. I seriously asked myself, why I’m putting up with this?

I straight cut all of them off in 2020 after seeing how fake and true colors people got during COVID-19. Trust me, after every one of them after I cut off, I felt better. What really hurt was cutting off some fine sistas I was pursuing but they went ghost during the lockdown. Even though cutting them off was healthy for me to forget and move forward, cutting off that many fine women was a shock to me and I felt that one. But it needed to be done and all it did was open up the door for 2nd-gen Latino chicks on Buford Highway here in Atlanta.

Did You See a Common Theme with My Regrets?

All of my regrets have a common bond and theme that I want you brothas and sistas to understand and realize. There is a major theme that I spoke over and over on Dream and Hustle and can you guess what is truly my big picture regret?

I regret that I did not claim my own story and own journey in life in my 20s. I allowed Black identity dogma to take over my life. I allowed wasteful and worthless people to be part of my narrative in my 20s. I let a lot of good people go or overlooked them in my 20s by chasing a narrative or belonging to a narrative that did not take into account all the people from all over the world in my life because that was my real life when I was in my 20s.

I was taught to starve and struggle and not reward myself. I had to eat hot dogs and Vienna sausage out of a can. No one told a vegetarian lifestyle was extremely cheaper than processed foods because no one wanted to see me take care of myself. If I told folks around me I’m running to Tokyo with a backpack and camera to check things out, those Chicago characters would have looked at me weird with silence to make me feel bad about pursuing discovery for my story and journey. I didn’t let them go and as a result, I did not free myself and allowed my life to hijack by the Black identity narrative instead of my personal spirit and calling. That’s the theme of what I regret most.

I need you brothas and sistas to realize at your young age while you working with non-Black brothas and sistas from other countries to bring them in your circle and stay friends. Visit them in Seoul, Korea or travel with them to Bali and don’t let them go to make your Black-identity friends happy, okay? Don’t stay stuck on that person you had a crush on when you were younger, live life in a fluid forward manner where that next hot person shows up randomly in your life and you discovering something new or experience a new destination. Leave the hood behind you, focus on what’s ahead of you. Don’t repeat the mistakes of a mid-life crisis Black man like me.