Keep Your Head

Most people that don’t know us personally, would never know we are a blended family by looking at us interact. Even visually, people assumed my dad just has the dominant genes because they can see a resemblance between him and my sister. We don’t typically waste time explaining to strangers, but it’s more of an undersized, Black, Brady Bunch sort of thing. Not without growing pains of course, but all the beautiful things are result of some pain, sacrifice, and growth. Our family is no different, but I can say with confidence we’re doing something right in these streets to make it look so effortless now.

brown wooden dock
Photo by James Wheeler on

I’m a very loyal person, sometimes to a fault. My ex girlfriend once told a friend of mine “Doug is super loyal, almost like a dog, if he ever loves you, he’ll love you forever” and that came months after we broke up. At the time, I hadn’t observed that trait in myself because we certainly cheated on each other. It took some maturing to realize the cheating on my part had nothing to do with my feelings for her or the people I was cheating with. I was just having an experience; I can’t really speak to her motivations or feelings. Even after all these years, despite the drama we endured and not speaking for 2 decades now, I still wish her the best and hope that she and her family are good. I have absolutely no reason to care, but I do. Not in a “I want to rekindle” sort of way, but in a” I genuinely loved this person” sort of way. I know, I’m wired differently, it’s weird to me too, but it’s just who I am.

The Fit

At 42, I understand these things about myself, however, at 14 I didn’t. When our families blended, I never switched from calling my stepmom by her first name to simply calling her mom. That’s not really crazy, but I felt awkward because my stepsister made the switch naturally. Hell, years before that, when I was 6 years old my brother and I went to Virginia to visit his father. We were there with him, and his wife, and they tried to force us to call her mommy and call him daddy…I never did, but my brother was able to do it with no problem. Granted, my stepmom is totally different and absolutely deserving of that title, she nor my dad tried to force me to use it. My brother came to Chicago a few months after they got married and he casually called her mom, and his ass didn’t even live there. All that to say, I felt pressure in the situation and didn’t know how to express that I felt it or why.

“If you can keep your head when all about you, are losing theirs and blaming it on you”.

Rudyard Kipling
close up photo of green leaf
Photo by Andre William on

My dad and my sister were the cerebral folks in the house, they bonded over debates and cerebral stuff. My stepmom and I were different, not sure what to call us, but we bonded over simply existing. I would go to her job at the Boys and Girls Club unannounced to hang out and then we’d ride home just talking in the evenings. My first summer job was at the club as a camp counselor. We got there early every day and left late every day because she was the director of the club, but she also was taking care of these day-to-day chores somehow in between meetings and making sure everything was going smoothly. She would do laundry in the laundromat across the street, go grocery shopping after work, and still cook dinner all while masterfully running this Boys and Girls Club and working on a master’s degree. She would even let me drive home in the evenings, a couple times she took a nap which is not something I can imagine being able to do with a 16-year-old behind the wheel of my car.

Growing Pains

It was mostly sunshine, but there was one time that I was simply being an asshole. My sister had already gone to college and more of these chores fell on me as a result. One obvious chore was taking the trash out. Our trash can was WAY too big though. It got filled and she took it out and placed the bag on the side of the can for me to take out. For no other reason besides teenage hormones, I took issue with this and left a passive aggressive note for her…which she got and didn’t appreciate at all. In the moment, I thought I was standing up for myself and my interests, but I never considered how much she was doing and sacrificing already when crafting my note. Needless to say, it pissed her all the way off. I got in trouble, still had to take the trash out and things were tense in the house for a little while. 

If you can wait and not be tired by waiting

Rudyard Kipling

What was unknown then was that I felt terrible about the note after the fact. My pride wouldn’t let me express this in words, and honestly, I had no idea how to express these ideas in any form at the time. So instead of making it right, I just waited for time to go by and hopefully fade from relevance. It’s kind of embarrassing to me now, but also a positive because the two main memories of me not doing what I’m supposed to do that she brings up are this incident and when she had to pick up my report card. She also heard that I was a bully from somebody, but that person missed the action that initiated me beating the brakes off the guy so it doesn’t count. 

Growing Up

I settled down after my junior year. I was far more respectful kid than teenage asshole…not completely so, but significantly less. She encouraged me to apply to this mentor protégé pilot program that Allstate was doing for “disadvantaged youth” at the time. I didn’t think I was deserving but she said that I should apply anyway. I applied, narrowly missed, but as fate would have it, one of the people selected ahead of me dropped out of the program. I used the opportunity to really focus in on learning what it takes to be successful. They placed me in an environment with several Ivy League graduates, high earning financial analysts and C-Suite executives. Surprisingly to me, but not to my stepmom, they liked me a lot and as a result requested that I come back whenever I was on a break. The Chief Investment Officer at the time was grooming me to become a force in Allstate, as long as I kept my head in the books of course. That seemed like an easy task, but I wasn’t mentally concerned with school at the time.

When all of this was happening, I seemed destined to ruin my life and be one of those people that squanders all their gifts on nonsense. It may not have been readily apparent to that many people, but luckily it became apparent to me. My stepmom put me on her cellphone plan, even though I probably wasn’t deserving, and I surely didn’t use it the right way. I was staying out, running the streets, getting into a bunch of things I had no business being in, camouflaging my outside antics with sweater vests and a college ID. There were several moments that made me think “I should be doing better” and the combination of people being shot and/or murdered around me definitely nudged me in that direction. One Saturday morning she stopped me to talk about the cellphone charges I racked up…a conversation I knew would be coming. I told her I would pay, and I did, but it was in that moment that I felt more guilt than anything because I didn’t have a job at the time.

Coming Around


retro cellphone with buttons placed on table
Photo by Masood Aslami on
three birds flying under blue sky at daytime
Photo by Jess Bailey Designs on

My stepmom once told my dad “one day he’ll come around” because I was notorious for bad report cards. Interestingly enough, I NEVER had that much faith in my abilities when I was living it. I can’t even imagine how frustrating it was for them to watch me constantly missing the mark, yet having all this faith that I would or at least should eventually start living up to my potential. I like to think that my decision to not squander my life was sparked by a single event, but it wasn’t. Shortly after I paid my portion of the cell phone bill, maybe a week or two, my cousin was shot on his way home. I was filled with emotion, anger mostly, but also looking for a sign regarding my next step. My thought process at the time kind of scared me because I was ready to throw it all away for revenge. That realization made me think “I don’t ever want my parents going through what my aunt is going through”. 

I can understand how good kids get caught up in bad situations. There were several days and evenings that I could have been one of them. One of the advantages that I had was my parents gave me a lot of tools to reason with. When I decided to finally drop out of school and go to the Air Force, I felt like I was letting my parents down. This wasn’t the path they envisioned for their child they believed to be so talented. It was a moment of self-prescription though; I needed a new environment to use whatever gifts they believed I had. I needed to not feel like I was letting people down every day. It’s not like my parents were doubting me, quite the opposite, they had all this confidence that I was intelligent and capable of doing great things. I didn’t see it, but they made me believe it. So, since I believed them, I left home to find out for myself if I was truly as sharp as they thought.

Coming of Age

I remember sending my parents the invite to my college graduation. It felt good to finally prove them right for sure. I made the dean’s list every time and ultimately graduated with honors and a 3.9 GPA. Oddly enough, I didn’t really think anything of that part, I tried to downplay it actually. My stepmom is the same way, except she has many more successes that she downplays. I find it interesting that influence can be passive, yet so impactful. Though we don’t share DNA, my stepmom is every bit my mom and I’ve benefited greatly from her ability to keep her head when everyone else is losing theirs. She understood how to reach me better than I did, and it worked eventually. I didn’t make it easy, and that will always haunt me, but I’m glad that I got the opportunity to make it right. 

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