New York City: Keep Working at It

I haven’t written in a lengthy time yet again. It’s been now three months since I moved to New York City, and well. It has been all but anything less than mixed bag of challenges. Some small victories. And generally a constant barrages of me asking myself if I made the right decision. The original plan was to blog my journey so far in the city. And frankly, I suck at the “daily diary” type blogging and it made me feel unmotivated at best. And that to me was a sign. We’re going to what I know. And that’s me. Sure it’s going to be a little more anecdotical but I’ll still sprinkle in a few special items.

But where do I begin on this hiatus I took? What is the point I start at and what is the point I stop? Let’s begin with the story thus far. I made the first mistake moving into Washington Heights. While the initial cost savings were a blessing. The emotional and personal cost was quite high. I can quite figure out people today and I won’t pretend to. But to put it in perspective. Let me explain it this way. As a Black man I have seen my share of injustices. But now to the be the unwilling victim of more because I am a man is wrong.  Plus to do it in a way to keep me powerless is far worse. I mean seriously, I read about what fellow black people went through with Jim Crow laws and becoming truly free. And if you’ve heard about my stop in Virginia you know I’ve experienced it too. We were powerless and to be the victim of someone with a vendetta against men was not in my program. So I can say I was charged more for rent merely because of a penis. That was the welcome for me in the city. I had no allies and no support. It was me versus the world it felt.

Then there was all the problems with the housing situation. Which related back to the whole I had a penis so I’m paying more in rent with no protection legally (in a way.) Black mold, leaking ceilings, mice, cockroaches, and a superintendent who intentionally would enter without notice.  It’s not the living situation I even anticipated.  I mean, the people I lived with argued the problem was because of me. That had I never came none of this would’ve happened. Or it is due to the fact that I am unclean male. If you ask my mother she’d be hard-pressed to hear that I am a dirty slob. That I live in filth and expect a woman to clean up after myself. Yet, this is the state of where I am. The gaslighting by the other roommates to tell the landlord that it  was mere exaggerating is more than enough to sour anyone’s experience.
And now comes the point where you ask me is it still worth it? Is it still worth moving a place that rent cost 4x times that of Montgomery County Pennsylvania. A place that is so densely packed with people an average trip to the grocery store can take over an hour just to pick up bread and milk. Eggs are $4.99 at the local grocery store. If you’re a smoker quit now cigarettes are $12 (I don’t smoke.) And now I’m just trailing off because the question I asked and get asked still sits perfectly perched on my keyboard. Was it worth it?

Yes. Okay. That was weird. Expecting anything different? No. I truly mean that. New York has made me hungry for more. I love my job. Being surround by startups and this young vibrant culture of people needing to make it themselves. Makes me want to do more. I’m also black and I know quite well about that. Being in NYC reminded me of an article from FastCompany by Lydia Dishman titled How These Black Founders Are Building Startups without Investors. In it she talks about how Black founders are under-represented and not to mention women too.  As the system shows minorities have to fight hard to be anything more. And that is what I am talking about. New York City is the mecca for startups this is where Uber, Warby-Parker, Amazon, Casper, and some of the other big names you know came from here. If you’re hungry it’s either here or California. And being part of it is what I wanted for a very long time.  So you get your foot in the door with something you enjoy. A job that makes you want more and you start there. For me being a minority I just want to take every chance I can get.

It’s crazy to think in a place where cash is king, that I’m sitting here talking about opportunities. But isn’t that the truth of it all? You take every one you get. You know where you want to be and you know what you want to do next. You have to start and keep running every chance you get and I can’t stop. I look at it and I want to ask what have I done. But that’s not the way to think about this. It should be about what I am going to do next.  And you can ask the question hat have you done because that’s the experience part of it. But it shouldn’t be a feeling of regret or of self-doubt. It should be really what it does to create the next opportunity.  In Star Wars: Rogue One Jyn Erso has a line that sums this all up so nicely. She says:

They’ve no idea we’re coming. No reason to expect us. If we can make it to the ground, we’ll take the next chance… and the next, on and on, until we win… or the chances are spent.

That’s exactly how I feel about being here in NYC. Maybe it is just me I truly believe we have to keep going until all our chances run out. Because how do we know if we’ve failed unless we keep going. Either we give up now or keep going until we’ve tasted failure. And even then failure isn’t the end. Just the question we have to ask ourselves of “what can I learn to improve myself next.” So yeah, sure this has been a challenge 3 months. But I’m going to keep taking my chances. Because that’s all I have and I’ll keep working at it.



Cover Photo by Jamie McInall from Pexels

Still Here. NYC Life

NYC Life…I have to confess I haven’t been that good about blogging since getting to nyc. To be honest first few weeks and first days at the job. In a new city. I am not going to lie was overwhelming. But once you find your pace things get better. Easier in fact. And I have a lot to say about that.


However I have given a lot of thought to my blog. What the hell do people want to hear? I kept asking myself that. Two things happened during this soul searching of what a blogger is supposed to be doing. The writer in me fought off being cliché. Being the county boy in the city. And I realised I am just going to keep the ideas flowing that I already had. Talking about what it is actually like. My perspective is unique (all of ours are.)


And that includes all that is taking to make it here. Startups and insurtech are now part of my life for good. Thoughts on what it means to be a New Yorker for better or worse. I know I will definitely offend people at times. But others hopefully will find some value in it. That I am being honest and not hiding things. My heart on my digital pages as I see it. And those of you who do read. Don’t be afraid to tell me what you wanna know about. Or how you actually feel.


I will leave you with one thing though I learned. Living here changes the way you view everything. What seems exotic or out of the ordinary starts to become routine. Like it is something you do everyday like breathing. But oddly enough I don’t find that sad. What you exchange for the allure or mystique is diversity. You begin to see what the city offers those who brave it. You get the good, the bad, and the ugly.  And the appreciation of all those things runs deep. Everyday you’re reminded about it. The city is alive and we all interact with it.


Time to Change Part 2

For my second post originally planned on talking about the NYPD impounding my car. How hard of a fight it was (and still is) to get it back. And how two governments in two different states treated me like I was scum or a criminal but seriously…That’s another post for another day. Maybe when I talk about how expensive it really was to move here. But soon I will be switching to a bi-weekly format. More on that later.


However, I wanted to talk more about jumping ship. I was probably one of the more fortunate millennials as my parents were a large part of why I finally took the plunge. For my most of my life they encouraged creativity and individual identity. That we need to be who we are and not let anyone else make that choice for us.


I remember one time I had a drawing class where the professor told me to be someone else. Cause the other student drew better than me. My mother noticed it didn’t sit well and after we talked it out I quit. My father was the same way and he always taught and showed us all sorts of things too. I have him  to thank for how technical I am in all things electronic.


For me that was what helped me to understand why Corporate America was so unsettling. For some people it is fine. It makes sense. It is their world. And frankly it was never mine. One thing I feel that never gets mentioned is that you can be born into a world and society can tell you to live a certain  way. However, there are mechanisms that give us an out. My parents were the first reminder of how I never had to stay in a broken system. Being taught the importance of creativity, individualism, and self reliance. While I will be honest and say they didn’t always stick the first time but they were there.


So it is no surprise when I say that I was never yes man. I suck at brown nosing. I despise nepotism. And I think too much structure and hierarchy is trash. While I am not against organizational I think there is a distinction between it and overbearing control. In all the jobs I had it reminded me constantly that this wasn’t for me. I think part of my anxiety was even due to this. I had conversation with my Mom recently and she said something was 100% right.. When I was kid they saw me living in Japan or Russia. And honestly, to me that would’ve been worlds better.


But to my dismay I fell into a line where you see other people your age. You want to be successful? Don’t chase the dreams. Chase the corporate culture. And yet, I wasn’t raised or born this way. Instead a system of college and career choices. That is what forces you into the mold. And that isn’t right. If you don’t want it why should you be part of it?


Joining the startup industry was the smartest decision I made for me. But what are you stuck in? Or afraid of? What keeps you up at night because there’s something not right in your career. More importantly, how do you do it? Take the risk. If you ask me it begins with recognizing where you came from and what makes you…. Well you. Because what matters in this life is who you are supposed to be. And how that fits into a career. You’re not a number. And you never will be.


I mean life is too short to keep chasing things that leave you wondering is there more. Make a plan, take action, question something. But do it for your life.

Time to Change

I remember sitting at my job thinking about where my life was going. Like many millennials I saw a system where you believed two things. You needed to go to college and you needed a safe and comfortable job. Preferable at one of the best companies, you know one you’d find on Forbes, Fortune, or some other business magazine.  One that was in the top 100. One that had unlimited potential. And your degree was the gateway the job was the road. But none of that felt right to me it never did. As I was just turning 30 years old I couldn’t help but wonder something was gravely wrong. In the 7 years of graduating college….nothing felt like what it was supposed to.


My trainer at the time one day did a presentation. He drew a chart and was talking about our personal health. He said that, life is path. We get on it spend years and hours doing things like working. And we allow ourselves to be chained or caught up in it. And we sometimes we never do anything about it and never start living.  To me, those words hit me like a goddamn freight train. Every job I held up unto the current one. It feel like I wasn’t living it felt like I was existing taking a paycheck paying down student loans and scraping by trying to find some meaning in the madness.


I’ve worked for 4 of the best companies to work for and I still felt something was missing. Like something wasn’t right. For one I felt there was a lack of opportunity…I mean I wanted to more but every time I found a door it would get slammed in my face. I would rock the boat I would want to try new things and try and innovate. But the system is old and archaic however, it was working so why would they want to change? I started in Property and Casualty Insurance which I loved. But I wasn’t getting anywhere. I remember my first raise conversation.  It wasn’t a big one it was small. 2.5%? Maybe 3%? I don’t know. I was told it’s not the amount that mattered it was the fact I was getting one. I was doing good work.


But to me I didn’t want to just be doing good work, I wanted to be doing more. I wanted to be changing things. But people in my industry didn’t want to change. I eventually would leave it and take a stab at an industry that claimed it wanted to change and make a future….darn it. I was fooled again. The healthcare industry is concerned with the bottomline and dollar signs. Talk loud and sound important. That what it felt like. I wasn’t paid to change anything I was paid to make sure the system flowed. And there I was again. Miserable. Bring to figure out where my place was.


So then, I started thinking. I wanted to be part of a startup. And honestly, I had the thought before and people scared me away. Startups fail, startups don’t offer the comforts, they don’t pay enough, you’re taking a great risk the number of things I was told when I vetted idea when I graduated was astounding. And so I did what anyone who’s dreams were dashed. I tucked it away in a vault to never look at it again. Except, I opened that vault and took out that dream. Brushed it off. And made a plan. I was going to quit my job and move to New York City. Start courting startups and get into the industry.


To me the question wasn’t the risk. I always was taught to be risk averse. Comfort and stability. Over taking the chance. Which for some is the way you want to live.  But I didn’t care anymore. I wasn’t happy. I hated everything about corporate America. The suits and ties. Constant meetings. Feeling like everyday was just an hour going by attributing to a system. A system I didn’t fit into. And I remember sitting there on so many days watching the death of my individualism and creativity. I’m 30 years old but I feel like I was at the end of my life. It got bad.


However, when you tell someone you took a pay cut and moved to the most expensive city in the US. Having maybe $200 in your checking account. Dragging a lead weight of student loan debt with you. Let me tell you the looks and conversations are not encouraging.  If you leave all that out, it is all celebrations. But that isn’t reality. Reality is many people my age and in my generation are drown in debt. We’re told to make the safe bets. Because you’re likely to drown. But what do you get if you spend a lifetime slowly drowning versus taking a chance to find meaning and purpose and trying to make it work.


In January, I told myself I was going to save up enough money and in 6 months move to NYC. Job or no job. That was the original plan. And life is a little funny when you make plans. It tends to set you up thinking it’s going to come straight and slow over the plate. And for me it didn’t. I got a hard curveball. A startup in the P&C insurance industry reached out to me. It was only January. I hadn’t had time to save or formulate a plan. So I declined. It was legitimately my dream job. But I kept thinking “I have to be safe about this” or things like “I’m going to be homeless if I take it “ Anxiety and self doubt.


But then a  month went by. And I was uneasy. Not sleeping. Googling the company reading the posting. Looking at other jobs. Interviewing and declining because it wasn’t a fit. And one day, I just decided. You know what….I’ve always avoided risks. I’ve always taken jobs that I wasn’t certain about but thought okay maybe it’ll be okay. I typed an email and I said “I can’t stop thinking about this job and the company. Is the position available?” The wonderful Head of People Operations, must’ve known she had gotten the line in good. Because months  of interviews. And a few trips later I had an offer in my inbox. And everything was becoming real…..


To spoil the story a little, I did accept it. And then I decided to start blogging about it. So here you’ll see the full story in as much detail as I can. Everything from daily struggles. To what it is like to be in the startup industry and more specifically the InsurTech industry. I honestly, can tell I don’t know what to expect. What to think or what happens next. Just that this is going to be a wild ride for me too.



I Hated 2017….

I haven’t done my year-end recap. And I’ve been hesitant about it. The question is why? And my answer was how much emotional baggage for 2017 I carried with me. A lot has happened. A lot has challenged me. And a lot has made me wonder about the future and my present tense. My best-friend broke my heart. Ending a relationship with me I thought was good. But that’s the thing about other people. You may never completely understand them. In 2017, I had some serious health implications that made me wonder what was the point to turning 30? I fought depression and anxiety and it was not always a winning fight. I struggled with my career and where I felt like I was going. I questioned my identity.  And those are just a few of the things that 2017 threw at me.

But I know I’m not the only one. We’ve all struggled. And it is so easy to look at the worst of what 2017 has thrown at us. I remember going on many dates and feeling like it was all hopelessly meaningless. That my faith in humanity and maintaining a relationship was as hopeless as our government. I have seen the bottom of the well that is our last year. And I got close to wondering what was next. And questioning why we plugged on.  Honestly, not to keep touching on it. But losing my best-friend. That relationship that meant so much to me over what I believe is one of the gut wrenching reasons isn’t easy. I mean, it wasn’t just an ending; it was a betrayal. Years and years of a relationship just flushed down a drain and one person left to pick up the pieces and make sense of it. You truly believe that someone understands you and knows who you are. And in the blink of an eye with one word they show you they’re wrong. They didn’t know you. That all those years were just some illusion where you poured everything into it. And the only question left was it real or not? Was any of it real. And last year, I worked a lot on proving that it was…. but honestly; it feels now as if being used and worn out. That all year long I sat there trying to make things work when there was no intention of it ever working.

And that could similar for a lot of things for last year. This whole idea of dating in your late twenties, for example. I have never known so many people to ghost you and just stop communicating in my entire life. And it is damaging to your ego. Or I think about all the cruelty I’ve witnessed too that others suffered. It paints a big mark on the entire year……

I hated 2017.

Well, at least that’s what I kept telling myself repeatedly. That this stupid year has done nothing for me. It has brought me such pain and sorrow that ….well. Made me hate turning 30. And hate everything about it. But a wise person whom she has always done everything to remind me of the best there is despite life getting messy and screwing with me said “Everything has a lesson and a purpose.” Or something along those lines. That even those relationships that leave us ravaged and broken inside they’re more than just wasted time or the betrayals we feel. That really hit me hard. As I was feeling so bitter about things. And I realised I had to let it go. I had to take another look at 2017 and see that maybe I was wrong. And focusing on the points that weren’t important and not seeing the lessons I learned. The progress I made.

She was right. This previous year I started on a journey to better myself and live my life and be happy. I have never blogged this much in my life (despite being on a three-month hiatus…) I started going to a gym and working out. My PR for my deadlifts is the highest it has ever been. I’m racing to hit 400lbs and I’m almost there at 345lbs.  I made new friends and showed that even at my age you are always learning something new. That getting older isn’t something to be fear but embraced as we’re learning more and gaining experiences that help develop who we are. I’ve made strides to better my mental health, where I did not have to continue with medication anymore. It’s not a question of what drug do I get to go on next. It’s a question of how do my skills and support system help me cope and live a life that I want.

I learned relationships are never easy, and it was a painful lesson ended with me saying I won’t give up on them yet. We’re not meant to be solitary people. We crave people around us. And when they hurt us it is on us to assume responsibility when we know who we are. People like me are diplomats and we sacrifice to make things work. But I learned I don’t have to fix everything. I don’t control the world or what people do or think. I control myself and my reaction and how I want to proceed. It was such an odd lesson to learn this late in life, but it is the truth. The more we stop trying to fix everything; the clearer things are. We enable ourselves to have space and see what is really going on. And let me tell you, for anyone that suffers from anxiety this is a lesson we all need. It can be a brief reprise in a life that sometimes is overwhelming.

Now I could go on for days or hours about this ;however, I’ll be brief. I genuinely hated everything about 2017, I wanted 2018 to come so fast because I wanted to forget and move on. But I was wrong. We need to embrace the journey and the lessons we pick up along the way. They’re not always pleasant and they’re not always gentle. Life and its lessons hurts as much as it redeems us.  And that’s the important point about it that there is duality for everything, where there is pain there is also hope. Where there tragedy, there is also hope. So I take that back I don’t hate 2017 I embrace it and the things that made me who I am right now writing this blog post. Am I scared about 2018? You bet I am. Am I excited? Without a question. I can’t pick what happens next, nor do I know what’ll come. But if I know one thing about it is, I’ll take everyday I’m given and I will make the most of it. Because at the end of it all it’s about our head-space. And that’s all each year is, where we’re at. And what we can do next.

So 2018, no matter what happened last year for you or for me. Don’t look at it and hate everything about it. Embrace it. The life lessons, the ideas, the stories, the experiences, its highs, and its lows. Because life is short. And the only way we grow is if we accept the past and keep pressing on.

(Repost) A Hard Topic for Men: Vulnerability

I remember the last time I had a good cry for a beautiful reason. It was my brother’s wedding, after doing my toast…. The sight of him on his special day. I had written a speech and did away with it. I spoke from my heart. The whole time I kept thinking. I’m going to cry. I’m going to sob my freaking eyes out. And I did. The tears couldn’t stop coming and even now I can feel them sitting behind my eyes. I cried because it overwhelmed me with good emotions. Things that felt good. I had opened up my heart in front of a room of friends, family, and loved ones.

Since then I am sure I’ve cried other times from the emotions I was feeling. And as a male, especially a young male. I don’t think that’s a bad thing. I was on Reddit the other day and I saw this question from one the users posed to women of the site asking “How do women feel about vulnerable men?” The responses were many responses to me were eye opening to read. However, it really got me thinking. Are men like me in fear of appearing vulnerable in front of women? In front of the ones we love? Or in front of anyone? Are we hard-wired to shy away? If you do reading on it there is a plethora of information. One of my favourite sites to read Psychology Today, they posted it about it and had some interesting revelations. Dr. Emma Seppala wrote ,

Although we may try to run from vulnerability, it is an inevitable part of social relationships. Even outside of romance, vulnerability is something we encounter frequently: calling someone who has just lost a child, asking a friend for help, taking responsibility for something that went wrong at work, confronting a family member about their behavior, or sitting by the bedside of a friend with a terminal illness. Opportunities for vulnerability present themselves to us every day, the question is whether we will take them.

She goes further to cite examples about how we as men try to find pragmatic solutions or try to fix problems in our relationships. That we do avoid vulnerability. And I kept thinking about the “why?” And the depth of what this really is. Being vulnerable in front of someone who you really care about is daunting. I am sure men and women go through it. However, part of me leans towards the fact that as men we learn to face it and try to skate around. But why? Why avoid something that enables us to feel. That enables us to relay emotions and share a social connection at a deeper level.

I am not ashamed to admit I cry, have these feelings I want to share with that special someone. My family, my closest friends, my girlfriend. I am also not ashamed to say I am scared as hell to open up for the fear of getting hurt. However, life is about the risks. It is about the chance that it will hurt us. If you look at it from the position of a romantic relationship, it is important that we look at our vulnerability. That the very moment you’re feeling scared to say what you’re feeling. Or cry in front of this person or anyone in fact. Admit when we’ve done wrong. Raise our hand and say that we’re drowning and need help. Say when something doesn’t make us feel good. Or even grieve in the presence of another soul.

Intimacy is only successful when we are open and honest. Being open and honest allows us to be vulnerable, and that seems scary. Frightening is the idea that I will show my heart and have no assurances of what happens next. And no one likes the hurt or the unknown, sure we can act tough pretend that we don’t care. Yet, the key point is we’re only human. We have feelings; we have hopes; we have dreams; we have these things that everyone experiences. We feel things. And here I am questioning why avoid vulnerability?

The people closest to you, those who love you…. they love you for you. Vulnerability isn’t this evil lurking to destroy you. Eleanor Roosevelt once said, “[d]o one thing every day that scares you.” I am not too afraid to even admit sometimes I’m scared myself. Allowing myself to be vulnerable. How do we know we’ll get hurt if we don’t take the chance? How do we know that vulnerability is bad if we’re never vulnerable?  I think it is something we as men (and women too) need to remember isn’t out to kill us. That moment where we are at the edge... that we’re vulnerable.  Why not take the chance and see what happens? Life is too short to hide.