Mistakes I’ve Made (that got me to where I am)Featured

I’m the Security Engineering Lead at HubSpot in Cambridge, Massachusetts. I have a son and a daughter — ages 10 and 8 — and a husband, who all (more or less willingly) accompany me as I run, hike, climb, bike, and eat my way through the world. I’m so excited to be part of the Elpha community and read the stories of so many great women!I fell into tech by accident, and I lasted by being a little bit oblivious. When I was 16 years old, a friend got me a job working in the network operations center of our local Internet Service Provider (think dialup modems) and taught me everything I needed to start in about three hours. It paid better than the Hallmark store I was working in and led to jobs that let me work weekends, second shifts, and summers all through college. I graduated with a degree in Electrical Engineering and Computer Science from MIT, but after graduation, I stuck with what I knew and spent 20 years working in operations for hosted and, eventually, SaaS services. Today I’m the Security Engineering Lead at HubSpot, working with an amazing team to protect our customers (and their customers) and keep their businesses growing. There’s something so different about working at a company with a critical mass of women surrounding you. It relieves the constant pressure of being the sole representative, giving you a chance to be yourself instead of acting on behalf of your whole gender. While it’s a very recent change, I finally feel like I can make the shift from fighting to be a role model for other women to actually being one. But in getting there, I’ve made more than my fair share of mistakes and I feel obligated to warn other women about them. So, without further ado, here are the Mistakes I’ve Made (that got me where I am), or the things not to do (and the reasons you might you want do them anyway). Plus: the ways I intend to change.1. Trying to be invisible. There’s a lot written these days about women taking up space and looking back, I’d say I’ve spent 20 years trying to take up as little space as possible. To me, that meant making things as convenient as possible for others at all times and never making waves or hurting feelings. I assume I’ve been promoted over the years because I do my job competently, but also because I make it easy to work with me. I will plan around your schedule, come to your office, pick up the slack on projects to get them in on deadline, handle the parts that no one else wants to do. My boundaries have been lacking. I’ve made, to my knowledge, zero enemies.When you’re trying to be invisible, no one’s going to pick you first for their team. Maybe third or fourth, when they realize they need that solid utility infielder. Someone who can be counted on to play their position and fill in where there are holes. Being dependable and making your boss’s life easy is surely good advice, as is being considerate of your coworkers. But by playing it safe and trying to disappear, I lost out on many chances to shine. Making yourself visible by taking risks and offering up new and different ideas opens you up to criticism, yes, but it’s also the only way to truly be seen. 2. Trying to do too much. I have a really hard time letting things drop on the floor. If I know something is going to fall through the cracks, I am going to try to save it. When you try to continue juggling as someone throws you new pins, eventually you will reach your limit. If you don’t choose to drop something, you’ll eventually drop something without being able to choose. For me, that has often meant prioritizing things other people expect of me, rather than the things I think are truly important. It is really easy to fall victim to the pressure of other people’s priorities and deadlines and lose sight of your own. But by trying to ensure I did everything that was expected of me, I’ve lost the chance to distinguish myself by doing something unexpected and truly great. I recently had the pleasure of working with a woman who was a great role model for me in this area. When you asked her for something, she would immediately ask when it was needed by. She transparently outlined what she had already committed to, how long she had, and where it fell in her list of priorities. She was always helpful when she could be, but also very upfront about things she just couldn’t take on without letting something else drop. Because of this, she delivered well and on time, and you could always trust her word. Whenever I’m starting to feel overwhelmed, I now try to consider how I can make use of some of her techniques. I have not even begun to master this area, but I’m starting to see just how necessary it is.3. Ignoring bad behavior. There is a principle in computer science that applies to interactions with other systems. It is known as Postel’s law, and reads, “Be conservative in what you do, be liberal in what you accept from others.” When I first heard it, as a freshman Computer Science major, it struck a chord with me as something that wasn’t just useful in protocol design, but also as a rule of etiquette governing interactions with other people. Anyone who knows me has heard this story already, but when I’m driving, if someone cuts me off or otherwise drives like a jerk, I generally assume they have to poop and just have to get home really fast. This is my own personal version of assuming positive intent. There is enough bad behavior out there that assuming otherwise would leave me angry all the time. I have likely ignored countless microaggressions, macroaggressions, slights, evil looks, mansplains, patronizing comments, and other bad behavior over the course of my career. In many cases, I probably didn’t even notice. In some cases, I noticed and assumed the aggressor had to poop. This has kept me sane and focused over the years, but doing the same is not advice I can give in good conscience. It was armor that was necessary back when having even one woman in the room was a rarity. With more than one of us, we can back each other up. We can ensure that everyone in the room is treated with respect (and most especially women of color, LGBTQ folks, and all of those for whom it’s still way too common to be the only one). 4. Not owning where I wanted to go. When there is no one that looks like you, it can be hard to picture your future. Maybe I lack imagination, but for years, I felt like I couldn’t quite see what the next step was until it appeared in front of me. I don’t know what happened to the female engineers at 40, 50, or 60, but I rarely saw them. I assumed, at least subconsciously, that whatever happened to them would happen to me as well. For me, that manifested as being interested in whatever job someone else wanted me to do. In some cases, I felt flattered that they thought of me. In others, it sounded like something cool and new that I might like to learn. I honestly don’t know if there are people out there who have a five or ten year plan and stick to it, career-wise. I imagine there are; the people who make VP by the time they are 35 must have planned ahead, right? If those folks looked at my resume they would notice it does not look like any sort of straight line towards an ultimate goal. I sought positions that moved me back to being an individual contributor no less than five times, only to wind up a manager again within a year. I accepted less money for a new job more times than I should admit. I tried new companies, new industries, new technologies.I can’t say that this has been all bad. Because of my crazy path, I am the ultimate generalist, able to understand enough about all aspects of a technical problem to connect the dots in a project. I can speak the language of software developers, ops people, network engineers, security analysts, auditors. I have friends and former coworkers across many industries and locations that I could call on if I were looking to (once again) change things up. I could probably just keep zigging and zagging my way along for the next 25 years and then retire happily. But it feels like it’s time to pick a direction, find the right skills to improve, and go deep rather than wide. To speak up and say ‘this is what I want to do’ rather than ‘whatever you need me to do’. I imagine it gets easier with practice? It’s a cliche, but the great thing about middle age is how much less you care about what others think. 20 years later, I’m still failing at all of these things on a weekly basis. But I only recognized recently that playing it safe was a failure. Those that know me in real life, please keep me on the straight and narrow. 2020 will be the year to be visible, to prioritize ruthlessly and to own where I’m going. It’s possible that it’ll also be the year I piss lots of people off, make lots of mistakes, and get fired. But my mindset has shifted enough that I’d be much prouder of that than I would be if I kept up with being the girl in the corner who keeps the plates spinning and waits politely for her turn to be picked first.
Thank you for venting your raw experiences to us. You are a role model! Keep us posted on your 2020 vision for tenacious ownership.
I love your post, and I can identify with a number of points that you have made. Thank you for sharing.Oh, and as someone who is looking for the next best role currently unemployed, my advice is, don't get fired! Instead, decide what you want and go after it, while you have your current job!
Thanks, I'll try to take that advice!
Oh my gosh @lysser6 this is an amazing post. I work as a career coach for women and some of the key themes we work on is:-Finding a North Star for where *you* want to go... I love when we realized you dont have to do XY or Z, even though the conventional wisdom says you should because it wont actually get you on your path.-Making visibility a habit. "When you’re trying to be invisible, no one’s going to pick you first for their team." So true. And when you are proactive about what you stand for, you get picked for the things that align.-Trying to do too much. I have some of my clients go on a 'no diet' to get them to practice saying no on a regular basis ;-) and sometimes I put myself back on one myself ;-)Love that you shared this incredible reflection.
Thank you @MayaPapaya for adding some greater perspective to one person's story!
Thank you so much for your transparency. This was like a dose of good medicine.
Thank you for your post! I am wondering though, how did you get yourself to come out of that corner? What are the actionable goals did you work towards to pull yourself out of that state of pleasing others, owning and being present?
Super curious to hear this too @jenniferjain. One of the assignments I'll give my coaching students is to create a habit of inviting out someone in their company (senior leaders included) for lunch either weekly or monthly. It makes it so you start to build allyship with others who might influence your career and who have a sense of the 'unwritten rules' to advancement (and to opportunities that you would love to get access too.)
What is the best way to start this on a team that is pretty secluded from the rest of the teams.
I am not the OP, but I can tell you what I did. 1) Start hanging out with (happy hours and lunches) the sales team. They are naturally more "out" than I am (as a scientist). I went with them intentionally to learn; check their demeanor, their outlook, their advice. 2) join some professional organizations - they taught me how to be comfortable in a room of strangers. And, I even became a Board Member at one, because I did so well there. That has also helped get me out publicly- I have to make an address at our events and post on social, etc.3) attend conferences or trade shows - get comfortable being out and shmoozing.4) take on new projects at work.
I wish you would do a whole post about this!
This is so good and I relate with each point. Thanks so much for writing it.
Thank you for sharing these lessons! Definitely going to start framing things more positively haha.
Thank you for sharing this!!! This is such a wonderful read!!
This is a powerful statement: To speak up and say ‘this is what I want to do’ rather than ‘whatever you need me to do’. Absolutely love it! I also really resonate with the part about 'doing too much'. I just went through my inbox/Slack messages/WhatsApp/etc. and cleared items that have been sitting there for a while because they fell off the priority list. I got back to each person to ask them when they need this by and let them know it's honestly fell off my priority list. Thank you for sharing.
"If you don’t choose to drop something, you’ll eventually drop something without being able to choose."Ugh, this resonates with me so much. Thank you for sharing this great post!
"When there is no one that looks like you, it can be hard to picture your future." - that's why it is so important to talk about our careers, our successes and why we should try not to be invisible (referring to your 1st statement 😊), you never know who you might inspire... 'You can't be what you can't see' 😊So, thanks for sharing your valuable experience with the community!
Fellow MIT alum here!Thanks for being so open about the lessons you have learned! A lot of our learnings come with a lot of pain, and it takes a lot of strength to share it broadly.