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.