I became a manager pretty early on in my career. While it began as player-coaching, it eventually evolved into at one point, having 5-6 direct reports all having a dotted line to me. I didn’t really think anything of it, as I always imagined at some point, I’d be in a management role and have management responsibilities. I was prepared and poised to lead, and based on feedback and performance reviews, it looked like I did pretty well as a manager. What I was not prepared for was having people report to me who not only were older than me and less experienced in this specific industry, but also being agist and sexist against me.

One of my direct reports (let’s call him Dave) repeatedly gave me a hard time not only because I was a few years younger than him, but because I was his female boss. He frequently made comments about how ridiculous it was that he reported to me despite having more overall work experience than me (I use to clarify and say that while he did, in fact, have more work experience, he did not have more experience in this realm, and thus if he had problems, he could speak to our team lead about this), how I was a feminist (always with a derogatory, negative tone), how he didn’t always have to follow everything I said. And when he didn’t follow what I said, he inevitably made mistakes. Some of them cost the company quite a bit of money, and for that, our team lead (Ogre) would then drag him into a room and verbally ream him. We had multiple layoffs at this company, and during one of them, Dave was actually on the chopping block; HR confirmed this with me. I nearly went hysterical at the idea of Dave getting laid off due to the timing; we were having a huge campaign launch next week, and if Dave got cut, I’d have to take care of this launch all by myself (read: many, many late nights into the wee hours of the morning being spent working on this to ensure success). I pleaded with HR to either hold off on laying him off until after the campaign launch or to choose someone else. Somehow, for once in my career, someone actually listened to me: they chose to lay off someone else and Dave was saved.

Three months later, Dave, constantly flustered by having a younger female boss, got a new job offer and tried to get a counter offer from our company. While the normal thing to do in a situation like this is to tell your direct manager, he instead went over my head and directly to our team lead, telling him that he had another offer, but would stay here if we doubled his salary (the balls to ask for that, really?). Both HR and our team lead declined, and Dave went on his merry way across the fence where the grass was greener. A few months after he left, we hired someone else who was likely four times as competent and quick on her feet. And she never questioned my authority or expertise.

Now, don’t get me wrong. I’m all for questioning authority and asking probing questions – in fact, I do this all the time (and have, at many times, paid for it). However, what I am not for is questioning authority merely on the basis of age, gender, or race. Discrimination, much?

Once upon a time, I worked at a tech startup that was headquartered in Silicon Valley. When I started my job, I had no manager. I didn’t know who would approve my paid time off (PTO). I had no onboarding schedule, no one set to train and mentor me given I had zero experience in this industry. I came in at my scheduled time on my first day in the satellite New York office, and they were NOT ready for me. I had no assigned seat and my computer was apparently not scheduled to arrive via Fed Ex for at least a few more hours from our headquarters. People awkwardly looked at me, a few introduced themselves, and that was really it. I asked a colleague what people typically did for lunch; he responded most people went out to buy lunch but would bring it back. After some hesitation, he offered to go out to lunch with me. And now, he’s actually my husband!!

Anyway, it was not a very welcome first day, and it gave me a taste of what I would expect in the coming months. A lot of the work had to be self-learned. A few tried to teach me and guide me in the right direction. The person who was supposed to sign off on my PTO barely even looked at my PTO requests and would just sign off on them. Though she was supposed to be my manager in name, I can count the number of times we actually had a conversation on one hand.

That’s the danger of working at startups that are truly “starting up,” especially if you are an entry-level worker. These types of places define “lack of structure” and “self-teaching,” and depending on your personality, this could be a good or a bad thing. But hey, when people talk about the glamour and glitz of working at a startup, somehow, they forget to mention situations like these.

I once had a team leader who I found to be charming as soon as I met her. She was charismatic, confident, articulate, and clearly came from a well-to-do family in India. She was self-deprecating at times, particularly about being Indian from India with her Indian-accented English, while at other times, she was extremely confident and would have staring contests with individuals she disagreed with. She was certainly a force to be reckoned with, and in many ways, I definitely did reckon with her. She was charming… and manipulative and controlling, and absolutely loved to instill fear in everyone around her.

One thing she loved to do was, well, telling people what to do. She prided herself on never, ever spending the company’s money on anything that did not absolutely have to be spent. So, when it came to things like taking teammates out to lunch, the rare times this did happen, she would spend this money out of pocket instead of expensing it. Her philosophy? “If you are offering to take someone out, you should be true to your word and take them out. Don’t say you will take them out to their face and then expense it. In that case, isn’t it [X company] taking your colleague out and not you?!”

When we had the occasional team outing (our team, depending on the time, ranged from 7-10 people), she or her manager (let’s call him X VP) would spend their own money for bowling or for food and drinks for us. Before and after the event, she would meet with us as a group and give us the same lecture. “You should be grateful that X VP is being so generous to take you all out. I hope you appreciate this gesture. Make sure to remember to thank him and be kind. And don’t do anything ridiculous at the event to embarrass me.” The day after the event, she would send a one-line email: “Please remember to send X VP a thank-you email acknowledging his generosity for taking you out, and let him know you had a good time.”

Well, thanks, Mom, for all the much-needed reminders on good manners and etiquette. We all really needed that, especially since we’re all babies, just between the ages of 22-35!

A former colleague of mine sent me a quick email asking to catch up over the phone sometime soon. He had left the company over a year ago, and he had developed quite the reputation for himself. He rarely came into the office. When we had to travel to San Francisco and Napa for team events or the annual company kick-off, he would make every excuse from “my mom is having a tumor removed” to “my basement flooded during the storm last week, and I need to take care of it.” He frequently stole office supplies when he’d be in the neighborhood on the weekends (our office manager told me this, as she saw the footage on our office cameras installed by both entrances). And when we finally caught up over the phone, he admitted to fake expensing on average about $3K/month for his last nine months at the company. “I milked them for every last cent that I could,” he said, gleefully. He made up business trips to see friends who lived in other states who happened to be located in the same cities where he had customers in his book of business. He wrote in work notes that he was doing “quarterly business reviews” with customers, when in reality, he never went onsite to see the customer for more than a “hi, how are you?” Instead, he took them to expensive, plush restaurants and wined and dined them. Well, those were his “business reviews.”

In the end, he got fired, but in a “nice way”: he was given a few days to say his goodbyes, tell his customers he was leaving. Management wanted to frame it as though it was voluntary to make him feel better. They gave him one month’s severance and even paid health insurance for him and his family for two additional months.

I’ve seen a lot of shady and unethical activity working as a “white-collar” professional, but I truly believe that this guy really took the cake.

A few weeks ago, I had a 1:1 Zoom meeting with our company’s CEO. It was a little strange. The request came out of the blue, as he normally asks my opinion about topics ranging from company morale, New York City office morale, how I think the customer success organization is performing and what could be improved, to where I think he should travel next for vacation. He wanted to ask my opinion on what he could be doing as the company’s leader to create a more diverse and inclusive environment that is ultimately anti-racist.

Our conversation was supposed to be only 30 minutes long, but it ended up going for about 45. We discussed what I’ve read in the How to be an Anti-Racist book, as well as the White Fragility book. He made a verbal commitment to me that he would at least download the White Fragility audio book and listen during his daily exercise. But the part that he seemed to miss the most is that he did not understand the inherent fact that I’ve mentioned a number of times on this blog: that it’s impossible to have a conversation about racism and have everyone in the room be comfortable or feel included. The whole idea of discussing “third rail” topics as he likes to call them is to be confronting, unsettling, to spur one into action. He disagreed. “The whole idea of diversity and inclusion is to be inclusive,” he insisted to me. “If we are not being inclusive, then this is not what we want.”

I paused. He still didn’t get it. How could I make him, a wealthy, privileged white man living in one of the most expensive suburbs of Northern California in a $12 million+ mansion, understand the crux of this issue? I elaborated on the background of Robin DiAngelo, the anti-racism educator and author of White Fragility. I told him that she has specialized in researching and educating on this area for nearly three decades. She has workshops every single day with people who seek to be more anti-racist, but fail miserably because they want to speak in generalizations as opposed to zeroing in on their own actions and what they can personally change in their day to day life. To ask someone to change their daily behavior, daily thoughts, is EXTREMELY challenging, if not impossible. And if she, as a 25+ year educator on this topic, still manages to “upset” and “exclude” people due to their white fragility and self implosion when confronting these issues, is the problem really her, the educator, the one prompting these questions, OR, is the issue the people who she’s attempting to reach who refuse to be reached due to their white fragility? When I said this, our CEO’s face suddenly changed. He appeared more contemplative, a bit more empathetic, a little closer to realizing that maybe, just maybe, it’s not the educator’s fault, the one posing the question’s fault, that maybe, the audience who is crying their white tears is actually at fault.

I’m not sure if I really reached him. It may all have been an act on his part. It may have been his way of weaseling himself out of the conversation to seem like he could be bendable, amenable to tangible change. Or maybe, just maybe he actually wanted to see some real change, something really move within our predominantly White company. I will never know for sure. But what I do know for sure is that most CXO teams across organizations around the world now are facing the same issue: they all want to participate in this:

“We at [Brand] are committed to fighting injustice by posting images to Twitter that express our commitment to fighting injustice.

To that end, we offer this solemn white-on-black .jpeg that expresses vague solidarity with the Black community, but will quietly elide the specifics of what is wrong, what needs to change, or in what ways we will do anything about it. This is doubly true if [Brand] is particularly guilty of exacerbating these issues.

We hope this action encourages you to view [Brand] positively without, you know, expecting anything from us.

-[Brand] (credit to Chris Franklin via Twitter)

For us, specifically, our CEO added a blog post to the company website noting that “Black Lives Matter,” that the leadership team would be encouraging employees to donate to these organizations as well. No monetary donation on behalf of the company would be given. No real changes made internally would be communicated via the blog post. It was an empty blog post that, around the same time, was also launched with BLM messaging added as a banner (which links to donating to Color of Change) when customers login to their accounts). At the same time, this organization is also happily taking money from organizations that support the Trump administration (many people in our sector of tech were happy and quick to point out this hypocrisy on LinkedIn posts that went viral). How does this organization reconcile this hypocrisy, if at all? Or do we just continue the BLM messaging on our blog and user platform while at the same time oppressing the lives of people of color?

For the last 12-plus years I’ve been working full time, I’ve worked both in SaaS as well as at digital marketing agencies. Although I’ve had many ups and downs during the course of my full-time working career, I’ve never stopped feeling grateful for all the good fortunes I’ve been privileged to have. I know that I have it better than probably 80-90 percent of the full-time working population given the opportunities I’ve been given, the perks and flexibility I’ve enjoyed, and the travel I’ve been lucky to have done to various parts of this country, not to mention how I’ve been paid. But even within our moments of gratitude, we also need to acknowledge what is right and wrong within our bubbles and identify what needs progress and why. I think that’s something that a lot of people fail to do for various reasons: they are scared to deviate from the status quo and “stir up trouble,” as that may put their own jobs and positions in jeopardy, they don’t want to create controversy, particularly because that disturbs their own comforts they get to enjoy, and well, they’re just lazy and don’t want to do anything that will require any proactivity on their part. It could also be a combination of all the above.

During my time working in the agency world, I realized how easy it was to get too comfortable with everything from the status quo, mediocrity, substituting activity for achievement (oh, this one is a HUGE theme across work in general and is not just about the agency world, though given that agencies make their money based on a percentage of spend from brands, this plays quite prominently here), and just doing your day to day, literally paper pushing.

But what has also happened is that a friend of mine who has remained in the agency world (and is still at the same agency I left) has repeatedly told me how toxic and awful the tech industry is once I rejoined it in 2013 because of the rampant politics, sexism, and racism that has gotten the spotlight due to reports from major tech companies like Google, Facebook, Amazon, and the like. He’s insinuated to me that he doesn’t think I should work in tech anymore and that my desire and decision to leave was misguided. My general feeling about this is that it is true that the tech industry is not perfect; it is part of the working world, isn’t it, just a specific sector, so it will never be immune from the issues that our society or world faces. Yes, the tech industry wears a mask of being more progressive, promoting diversity and inclusion efforts internally, and taking care of its employees more than the average (read: crappy, cut-throat, bare-bones) American company through its offerings of attractive perks that range from “unlimited PTO” (I will deconstruct this myth/recruiter selling tactic in a later post), free snacks, daily lunches, reimbursement of all commuter costs, 100% employer-covered medical/dental/vision premiums, fitness/gym/massage reimbursements, to even fertility and egg freezing benefits, but because they do actually go above and beyond with these types of perks on average vs. other industries, that is enough to make someone want to jump over from another industry into tech. Why? Because the relationship you have with your employer is transactional, as I learned pretty much the very first time I got laid off in 2009. You offer your expertise and services to your employer in exchange for a salary and whatever benefits they are willing to offer. There is nothing more to this relationship, so you should not think anything more of it… because we know, for sure, they certainly will not. They will not hesitate to cut you when they no longer think they need you (whether that’s because you actually are under performing or, in most cases, because certain key people may not like you. Hello, politics). Because of this cold, blunt fact, why should we, as potential employees, not want to take advantage of every potential benefit and perk an employer is willing to give us and milk it for as much and as long as possible? We’re only maximizing our own gains, and if we do not think of ourselves first, it is guaranteed that no one else ever will — and certainly not your employer – past, current, or future. Therefore, with that said, this is why I strongly believe that unless you are working for yourself and can call all the shots, the best industry to be working in to maximize the “you” benefit is in tech. Just don’t work at one of those loser, backwards tech companies that offers zero of the attractive benefits noted above — otherwise, why are you even working in tech?! Do you think you are going to change the world? Don’t be that naive and take care of yourself — knowing that no one else will.

I had a call scheduled this morning to chat with Chris’s friend who works at a company that I’m interested in. He’s been friends with her for a few years, but I’d never met her before since he likes to keep separate parts of his life separate, and there was really no reason for me to meet this person, so I never really cared to ask. So I called her to get a sense of what the company was like and how she liked it, and it was clear from the beginning of the call that she really loved working there. She talked about the company leadership, the culture, the nature of her work, and she gushed endlessly about how great it was. It got to a point where the entire conversation just seemed like the type of conversation I’d have with the company’s HR or recruiting team; she said glowing, nearly-canned positive things about the company like “great work-life balance,” “everyone is so amazing here,” and “senior leadership is really accessible, their ‘door’ is always open for you; the only blocker to developing a relationship with them is yourself.” I nearly vomited in my mouth a little when she said that last part. How often have I heard that from recruiting teams in the past, or people who truly drink the kool-aid.

While I appreciated the time she spent to chat with me, I didn’t really appreciate the PR-spin on her perspective; it came off as too enthusiastic, a bit disingenuous, and well, not authentic. Luckily for me, I have other contacts I can speak with at the company through personal connections, so I can get a more well rounded perspective, but it just struck me as odd that she was technically supposed to be a personal connection through Chris, but she gave me a not-very-personal perspective of the company.

My mom always says that the older you get, the wiser you get. I actually don’t really agree with this. The older I have gotten, the more confused I have gotten about why and how people are so twisted and weird.

In 2009, when I got laid off, my dad cutely asked me, “Well, will they rehire you later?” When my dad used to work at a glass company, they would occasionally go through temporary layoffs due to lack of services requested. When the requests for glass installations decreased, team members would get let go, and when the requests increased, they’d get called back. So my dad thought that maybe this would how it would work in the white-collared world. Nope, that’s not how it works. Once you get laid off, you’re laid off. Though I have heard of some snafus where some individuals who were laid off were requested to come back months later, that is pretty rare to non-existent.

My mom tried to be comforting, but she was a total wreck. She thought she was thinking about how I was feeling and being sympathetic. But from what I could see, all she felt was shame for herself to have to say that she had an unemployed daughter. She sent me a hundred bucks to make me feel better. But that’s kind of where the comforting ended. She insisted many times, at varying volumes, that I move home (yeah, I would have rather dropped dead). She insisted that the recession was so bad “because of that Black man in the White House!” that I would not find another job in New York, so I should just give up. She also didn’t want me socializing with anyone, saying that everyone would look down on me for not having a job. She didn’t even want me to go to my cousin’s wedding the next month (I still went). She made me feel lesser than for not having a job. I obviously moved on, but I never forgot how she made me feel worse about myself based on no wrongdoing of my own.

That’s the thing, though. That type of thinking is not necessarily unique to my mom; as Americans, it’s nearly ingrained in us that our jobs define us. That’s why most of us are assholes, and when we in America meet people for the first time, we immediately ask after exchanging names, “What do you do (for a living)?” Why? Because our (paid) work defines us. Because our paid work makes us valuable to society. Our paid work contributes to our national GDP, our sense of self-worth, our sense of being. Our salaries say to us, “this is the dollar amount you are worth as a human being.” But… isn’t that sad… and just… wrong? How can your kindness be measured? How does your generosity factor in? What happens to all the good deeds you’ve done so selflessly? Do they just get completed and then taken for granted and forgotten?

I would love to exist in a society that did not measure people based on their salaries and net worths, to be viewed as a contributor of society based on my passions and strengths as a person. But that is a utopia and so far from what the United States would ever be — a country that devalues so much that is important about human beings.

When I first started full time work after graduating from college, I graduated into a recession. Just four months after starting at my new job at a SaaS company, the company had a layoff, which resulted in a number of my colleagues getting let go. Given my connections to the HQ, I knew a second layoff would also happen soon after. All signs pointed to it — employees not getting their bonuses, being forced to take X number of days off before the end of the year. The writing was on the wall. I started applying for new jobs because I knew I’d get laid off — last ones in are usually the first ones out. I even packed up the belongings on my desk a few weeks before the second layoff happened. That made it easier for me to make a quick escape when I finally did get laid off; no need for a big show of packing up my desk. I spent three months being unemployed, which ended in two full-time job offers and one full-time contractor offer. It was not a fun time at all, but in the end, I learned to never be that loyal to any company because at the end of the day, every single one of us would always be discardable. Very little protects you when you get fired or laid off; you’re powerless as an individual.

So when I realized the second recession of my adult life was coming, I imagined getting laid off again. I’m in a very different place in my life now and am way more comfortable then I was in 2009, but you know what? No one wants to involuntarily leave their job. No one ever wakes up in the morning and says, “I’d love to get laid off today!’ It’s demoralizing. It’s a huge ego hit. It is especially hurtful when you know that you’ve been the top performer on your team, but even that does not make you immune from a layoff. But it’s a further reminder that the working world is full of politics, gossip, backstabbing, and the game of favorites. And if you are not a favorite, your employment is always at risk.

People like me don’t fare so well in that schema because I don’t like to suck up, and no one would ever, ever label me a kiss-ass. I just want to be who I am and I will stand for what I believe in, and I won’t kowtow to people because of their positions and their standings as “favorites” among the CXO team.

If you aren’t going to be true to yourself, then who are you going to be true to?

Like many other tech companies who are attempting to be seen as “woke” and progressive during this period of heightened awareness of racial injustice, my company granted today, June 19th, or “Juneteenth” off as a holiday to allow employees to take time for themselves to educate themselves about this day in history. Juneteenth, rarely taught in schools, is the oldest nationally celebrated commemoration of the ending of slavery in the United States. On June 19, 1865, Union soldiers landed at Galveston, Texas, with news that the Civil War had ended and that the enslaved were now free. However, the issue here is that this news came to Texas 2.5 years AFTER then President Lincoln announced the Emancipation Proclamation, which had become official on January 1, 1963 (funnily enough, this is basically like how the country is run today; just because something becomes national “law” does not mean individual states instantly start enforcing these laws).

We had a series of programming lead by our Diversity and Inclusion Group (DIG) team along with our Optimizely.org rep. I joined one of the early sessions on the history of Juneteenth and also spent the day exploring the much quieter Manhattan Chinatown, buying different foods I’ve missed out on over these last few months, exploring bakeries and noodle/tofu shops that I’ve been wanting to buy from, and just wandering the streets to get a sense of what life is like now given so many businesses are either still temporarily closed, or have even permanently closed during this COVID-19 shelter-in-place period.

Throughout the day, I continued listening to the White Fragility book and lamented the fact that this book, like so many books, movies, articles that are so informative and enlightening, will likely never be received and consumed by those who need this information the most. It’s sad to think that even when people have willingly participated in anti-racism training with the author herself, Robin DiAngelo, that they will get angry when their own racism is called out in incidents they themselves chose to willingly share, and that they would then be a live example of white fragility in a classroom led by the White Fragility author. I am sure that similarly, many of my colleagues who so severely suffer from white fragility refused or declined to participate in our company’s Juneteenth events, likely because they are so consumed by their own feelings of *potentially* getting hurt in a situation where their hurt doesn’t even matter.