The Diary of a CPO - Chapter 9
What I thought was a curse became a blessing.
When I was a little girl, my most favorite pastime was riding my bike.
I absolutely loved riding my bike, racing down the streets, finding any hill that I could speed down and often scraping my knees, shins and elbows as I hit the pavement. Sure, I cried and tried to wash off the bright red blood as I stared horrified at the raw mess of my skin. But there’s nothing like a great bandaid to patch up the mess and get right back out there again.
I also collected toads, tadpoles, bugs and snails. Most of my friends were boys and they often let me lead the pack because I always had the best ideas. We built forts, got lost in bike trails, snuck a rowboat out to the lake during camping, and we hung out at the comic book store back before it became cool for teens.
When I got older and became a teenager, I started to hang out with more girls. Some girls I met were really spontaneous and didn’t let anything get in their way. Other girls were more insecure and carried a heavy weight of emotions, always worried about what others would think. I tended to gravitate towards the former group and felt like I could be myself without having the burden of my insecurities drag me down. Teenage years aren’t easy for anyone, especially when your hormones are invading your mind for the first time and you’re trying to balance growing into an adult while still wanting to be a kid. I was caught up with wanting to grow up and be a responsible adult while still enjoying the freedom of being that girl that can feel the wind in her hair while riding her bike down a hill.
When I finished school and started working in the real world for the first time, I was excited about building my career. I daydreamed about what I would become in the future and threw myself into my first real office jobs. The jobs were relatively boring and I soon realized that being a cog in the wheel seemed to be just a normal part of work life…gross. I worked in corporate jobs back then, like large public companies that everyone has heard of. The ones that have matrix environments and a company directory of thousands of people that you’ll never meet in real life. I would occasionally see the actual CEO or an executive walk by in the morning but never really get the opportunity to talk to them or spend time with them. If they happened to stop by my cubicle or I happened to be in the elevator with them, I made some awkward exchange and blubbered something dumb that I regretted immediately after walking away and that was the extent of my interaction with a “top leader” at the organization. I also noticed a lot of the executive leaders were men. They were pretty nice and often chatted with good humor. There were also a few women. They weren’t so nice and didn’t bother to say anything when they walked by. It was strange to me considering there were so many women (us) supporting the work for the business.
Regardless, I assumed if I worked really hard and exceeded performance expectations compared to my peers (who didn’t really care if they were working hard or hardly working), I would get an opportunity to move up. The thing about corporate life that people who have never worked in it don’t understand is that things move incredibly slow. The pace of work, the pace of getting things done, the pace of planning, scheduling, discussing, meeting, deliberating, contemplating, de-risking, reviewing, re-reviewing, re-discussing can be incredibly soul crushing for people who just want to get shit done. So with all that time you have, in-between an idea and execution, a lot of corporate life is spent talking to peers and psychologically destroying your confidence. I encountered a lot of “advice” from peers who were mostly women. A lot of the advice I was given sounded like complaints and it was also the first time I heard of the term “glass ceiling.” I had to look it up and learned that it meant women would never fully have the opportunities in their career to move up compared to men. This also applied to “minorities.” So essentially, I ticked the box twice.
In those early career years, I started to lose my confidence for the first time. The influence around me was stifling and I started to believe that I will probably never be good enough because this is how the world works. So I did my job as best as I could and I tried to block out all the negative energy and gossip that was surrounding me daily. I wasn’t sure if I was depressed because of corporate life or because I was a woman working in a system that would apparently never give me an opportunity to succeed. It was also unfortunate that I never had a mentor, an advisor or someone in a more senior position that could give me some good advice. I mean, I was twenty-something and it wasn’t common to have a mentor back in those days so I was just blind to what I didn’t know.
I started to feel like I was cursed for being born a woman. Why couldn’t I have been born a man? Life would be so much easier, and guys seemed so much more easy going (at least compared to the women I worked with). I saw men going out to have a drink after work, watching sports together in the lunch room and playing golf together at company events. They all seemed to support each other and provide advice, guidance and networking opportunities. I didn’t see that with the women. They all complained that they had to go home and take care of their kids, cook dinner and clean the house. I asked them why didn’t they split up their chores with their husband and the response was always between 2 answers:
They complained that if they didn’t do it, their husbands wouldn’t do it. It just wouldn’t get done.
They complained that they were not the breadwinners and so they had to ensure their husbands managed their own careers and brought home the bacon and they will add to it as a supplementary career, but they really wanted to be a stay at home mom.
I wasn’t married at the time, but I thought both reasons weren’t good reasons for a woman to do double duty compared to the men. In my twenty-something single, unmarried and childless brain, I thought, I’m either never going to get married if this is the price of entry, or I will only marry if I can find an equal to myself. I also witnessed so many older women who were getting divorced and had no income or job experience to make a proper living. I saw divorced men who had young new wives beside them driving around in luxurious cars and dressed in dapper suits. And when I talked about this with women in their twenties and thirties, they always assured me that their husbands would never leave them and that the sacrifices they put into their marriage would keep them bonded for life. I’ll bet these 50-year old ex-wives probably thought the same thing when they were 20-year olds.
My plan was to never marry, build up an incredible career, travel the world and be fabulously glamorous. I often dated men who were a few years older than myself, who had seen and done more than I had and I could learn from them. That was the plan, until I met this younger guy (6 years younger than myself) who started off as a buddy of mine that I could punch in the arm and hang out with and totally be myself. My girlfriend was coaching a hockey team at the time and he was one of the players. She would ask me to come watch the game so I did and that’s how I met him. He had a “crush” on me at first, which I didn’t take seriously but after a few hangouts, I realized something about him that was different from the other guys I dated. He genuinely respected everything that was important to me. He didn’t impose his ways of thinking on me like some guys did and he didn’t act like he knew it all. There was a genuine curiosity in him about all things me, and he was actually a lot of fun (if you can make a girl laugh, you will likely win her heart). I told him I never wanted to get married or have kids, and he said no problem. Then one day I woke up and had a change of heart. I told him, I do want to marry and maybe have a kid or two. And he said ok.
We got engaged, then married, and then had our first kid. After 3 years, we had another. And while I doted on my girls and spent an enormous amount of time as a new mom, loving every minute of it, after a few years, I decided I wanted to go hard into finding a career that I was going to love. That’s when I transitioned from corporate to startup. It was at this time that my eyes fully opened up and I felt like I could see things in color for the first time in my life (at least when it comes to my career which is a huge part of my life). The next 10 years of my life goes deep into startup life and anyone who has ever worked in startups (especially early stage) knows how damned hard it is every day. I couldn’t have done what I’ve done in my career without my husband who dedicated the last 10 years picking up the girls, making lunch and dinner for the family, getting groceries on weekends, filling the gas for weekdays, cleaning the house and never complaining about it because he worked in steady corporate which allowed me to work unconventional hours in risky startups. If you want to have an equal partnership with someone who respects you and won’t make excuses, focus on finding the right partner. Your marriage, your career and your kids will thank you for it. Remember, not all men are the same and we don’t have to accept the status quo (at least I won’t).
That first year in startup, I did everything wrong. I worked with a founder who was incredibly dysfunctional, highly emotional and could be elated one minute and then pounding his fist on the table the next. I remember we were on a call once where he didn’t like what I said and a few minutes later, he hung up on me. Like, when was the last time an adult hung up on you? I can’t even remember because it’s so immature and petty but that’s how he was. There were so many more incidents that occurred after that that made me want to roll my eyes into my head each time something came up. Do you remember when we heard that Travis Kalanick, the founder of Uber who was rolling on the floor after video came out of him yelling at the Uber driver? And his executive team was cringed out and so disappointed in him that they just couldn’t work with him anymore? That’s how I felt most days working with this founder. He was eventually removed by the board but I worked with him for almost 2 years. On better days, I surprisingly learned a lot from him as well. He taught me to eat the frog first and get the hard things out of the way. He also shared an incredible amount of feedback with me, which I really appreciated because we never get enough feedback, ever. My ability to grow so quickly in this role was in huge part due to his belief that I could do anything. He gave me my first executive opportunity and I will always be grateful for his belief in me. I also experienced severe burnout for the first time in my life and had to go to the hospital for surgery before I quit my job and recuperated. Upon reflection and hindsight, I know that burnout can occur because you are the most relied upon and highest performing employee on the team. I know now that you can die by being loved to death.
That was my first role at a “crazy” startup and then I followed up by joining 5 more over a decade. My next few startup experiences all varied from early stage to later stage, from small to large, from male founders to female founders, from VC backed to M&As and everything in between. I learned so much about growth, resilience, frustration, depression, loneliness, betrayal, coups and winning against all the odds. They say fact is stranger than fiction and startups can be a strange place. It’s not for the faint of heart and sadly, a lot of women say it’s not made for them. But what if you could learn something great about an environment that is vastly different from what you know or expected? Nobody said startups were easy. Nobody. It’s the exact opposite of that. And most days, everyone finds it difficult, not just women but men alike. For me, the ambiguous environment and the raw lack of processes was refreshing to me and I felt like I could work faster and execute more quickly due to the lack of red tape. But I also had to balance that risk with things that might break and cause issues in the future. Startups are high risk and I’m not sure if some women find that too scary or too risky but I got a thrill from it.
So this is where I’m going to go full circle back to the beginning of my story. When I was young, I thought being born a girl was a curse. I believe that the world was made for boys and men and we were just here to fill the spaces in between. I believed maybe we were just the supporting cast members but never the main actors. I mostly believe this because the women told me I should. I worked with women that often made me feel small and created an insecurity that I had never felt as a child. And when I grew up, most women didn’t lift me up or give me opportunities to develop and gain confidence. Most of my managers were women HR leaders and they were pretty difficult to work for and with. They had very low self esteem and they protected themselves by making other women feel vulnerable by stripping away their confidence. I started to feel less confident in each role, until I broke out of corporate, joined risky startups (which happened to have less women) and worked within a more male-dominated workforce that just sort of accepted me as one of the guys. The startups were also tech startups, so success was factored on KPIs, OKRs and target outcomes (numbers don’t lie). There was less emotion and more logic and objectivity. Logic and objectivity to make decisions, how beautiful is that?
That’s not to say every day was sunshine and rainbows (remember that first founder that I worked with)? But at least I could be myself and nobody really judged me. Being around guys who were confident made me feel more confident. Being around guys that didn’t talk about insecurities and emotions made me think less about those things. Being around guys that were direct and honest gave me confidence to do the same. So I guess my point is that sometimes, women create the kind of deep seated insecurities that we are trying to avoid by instilling it in others and making us acutely aware of it. The “groupthink” that occurs can discourage our ability to do things we’ve never done before and hinder our ability to succeed. You know that saying when doubt creeps in? The same goes for our deepest insecurities - are we manifesting the stereotypes of women that we are trying to destroy? Men get bashed so much for not supporting women, but in my experience, women have bashed women far more than the men in my lives. I’ve had more women troll me online, bash me behind my back and turn my words around to weaponize them against me. I’ve also had to delete more hateful comments and block more LinkedIn users that were women than men. Twitter (or X) has always been extolled as the most obscene online platform outside of Reddit, but I see more and more women indulging in grotesque and rude comments on other women’s posts versus just scrolling by. It’s disturbing to me and I’m worried about the future of women if this is how we are going to treat one another. Behind all the virtue signaling of women supposedly supporting other women out there, I’ve not seen that to be true.
So going back to my childhood, what I realized coming full circle is that being a woman is amazing. I get to still do all the incredible things that I’ve always enjoyed as a little girl and I get to surround myself with the supporters that will allow me to be me. My supporters have predominantly been men in my life and career, and as a result, I won’t bash them the way women sometimes want me to. The male allies I’ve had in my life and career should be celebrated and they deserve the credit due. Not all men are perfect, far from it, but the majority of them have been my ally. Being a woman is not a curse - it’s a blessing. It’s only a curse if you are the woman that creates discourse for other women while pretending to be their greatest supporter. So to women I say, maybe it’s time we change how we operate so that we could support other women and also find some wins for ourselves. Your daughters and your sisters will thank you for it.
Note, I’m certain there are some women who will be “offended” by my diary entry here but it’s a diary after all - you just happened to read it.