Two-line summary

15 minute read

I often wish I could go back and warn my past self about the mistakes that shaped my professional character. Given the profound value of learning from failure, I sat down to organize an introspection on the ways I've failed forward (many of which I'm still guilty from time to time).

Table of contents

• Part I: Mindset
• I prioritized being perceived as productive above all else
• I optimized for volume of work instead of impact
• I was afraid to look stupid
• I mastered the complex before I mastered the simple
• I minimized myself to be more palatable
• Part II: Value
• I underestimated the value of a great manager
• I failed to recognize the relationship with my manager as bidirectional
• I dismissed the importance of securing professional advocates
• I was not intentional about positioning myself to serve my goals
• I focused on providing value far more than receiving it
• Part III: Boundaries
• I tolerated a toxic work environment
• I allowed others' lack of boundaries to shape my own
• I accepted others' unhealthy opinions as fact
• Closing thoughts

Part 1: Mindset

"I prioritized being perceived as productive above all else"

This lesson (and the one after it) I put first because I struggle with them to this day.

Years ago in therapy, a psychologist asked me whether I could recall the last time I felt proud of an accomplishment without being praised by someone else. I couldn't. I hadn't realized until that point how much of my self worth relied on external validation. I'd spent my childhood building my entire identity around being an overachiever - so much so that the adult version of me still has to work hard to see value in who I am and not what I do.

This carried over effortlessly into my career. I wanted to be known as the person who got shit done, the first person to respond, the last one to log off, the one everyone goes to for difficult questions. I craved a reputation as an overachiever more than anything else. Even now, the most common piece of positive feedback I get is "you're so productive" - but it comes with too high of a cost.

When performing at 150% becomes your normal, even showing up with 100% feels like a failure. I've spent too much of my career oscillating between hyper-productivity and burning out, and being perpetually stressed has taken the joy away from ambition.

This is one of those lessons that I've had to learn over and over again. It comes down to decoupling a deep-seated relationship between productivity and inherent value. I'm not there yet, but if you're interested this topic, I've found Rick Hanson's books to be useful.

"I optimized for volume of work instead of impact"

This lesson is a consequence of the last one. In the pursuit of being seen as productive, I found myself toiling over trivial tasks for the sake of marking them as 'done'. In the beginning, it was well-intended. I would 'front-load' trust with stakeholders by powering through an unsustainable workload. Sure, blowing them away with a first-impression would solidify my reputation as an invaluable team member, but volume didn't equal impact.

A manager pointed this out in one of my performance reviews, noting that I'd pumped out so much work and yet it was hard to find just one or two things that stood out as achievements. In retrospect, the projects that have lead me to promotions did so on the basis of impact; reputation is not enough.

I now try to frame work by asking, "is this something that I'd be proud of two years from now; would this stand out as distinctive on a performance review?"

A common issue I see with junior peers is that they lean toward volume to prove value because they're not trusted with opportunities that have impact. This is worth a candid conversation with your manager. Ask them, "what work do we have planned for me that allows me to learn the skills of the position above me?"

"I was afraid to look stupid"

There's a speech by Michelle Obama where she discusses having a seat at some of the most powerful tables in the world (corporate boards, G summits, United Nations). I fondly remember her saying, "here's a secret: they're not that smart."

Early on in my career, I was afraid to look stupid because many of the leaders around me were more occupied with looking good than doing good. My concern was that if I asked a question that revealed a gap in my knowledge, it would leave people with the impression that I have a lot to learn. I thought to myself, "if you want to be promoted to senior, don't ask questions that a senior person should know."

I had to learn the hard way that individual interactions don't define or tarnish your overall ability. Some of the smartest people I work with ask the most basic questions, and their lack of ego is actually a testament to their skills. Personally, this came with gaining confidence in my craft over the years. I got to a point where I didn't care if my questions sounded stupid because I don't believe anyone thinks I'm stupid.

I also realized that if the only thing standing between someone's opinion of me and being stupid is a simple question, then the issue is not me - the real issue is that the person values appearance more than merit.

"I mastered the complex before I mastered the simple"

In my final year of undergrad, I took an algorithms course that included daily stand-ups with our assigned teams. I was acing the class, but I was also late to stand-up... every day. I remember the professor giving me the most memorable piece of feedback I've received to date, "you've mastered the complex, but you struggle with the simple."

This lesson has taken on different forms to make periodic appearances in my life. In pair programming interviews, one of the biggest red flags is when a candidate jumps into a nuanced machine learning solution before defining a success metric. Or have you ever met someone that keeps name-dropping a concept that you suspect they don't truly comprehend?

It's understandable; data science offers so many incredible avenues that it can seem boring or menial to focus on the fundamentals. When I feel tempted by complexity, I always return to my professor's advice: have I mastered the simple?

"I minimized myself to be more palatable"

There are many aspects of my personality that I repressed in the interest of presenting as a professional. I find this to be most common with women in STEM.

I recall being advised by my campus career centre not to wear makeup to engineering interviews because it could convey that I'm not serious enough to do the job. A friend at an esteemed tech company recently shared with me that her manager's only feedback on an important presentation was that she should practice lowering the pitch of her voice because it came off as unintelligent.

The lived experience that femininity is mutually exclusive to intelligence caused me to change even the subtlest of preferences. I thought, "what if my hoop earrings and acrylic nails make people forget I got a master's degree in computational math?" As petty as it is, I really believed that it would.

All of this to say that I've grown to refuse to allow work to define my character. There are still many work environments that operate with biased and discriminatory undertones, so I'll preface this by saying that this lesson is applied from a place of privilege: we all deserve to work in an environment that doesn't require you to hide who you are in order to succeed.

Part 2: Value

"I underestimated the value of a great manager"

You might have heard the phrase, "people don't leave companies, they leave managers." This puzzled me until I experienced it firsthand. While I did just fine with most managers, I didn't realize what I was missing until I had a great one. 

Several years ago in the craze of the holiday season, I made a multiplication error that caused a data point to be communicated incorrectly to a senior leader. He tweeted it, and a random commenter found the error. As I sit here typing this, I vividly remember the panic I felt reading the tweet over and over again. Five minutes later my team was being ushered into a war room where before I could speak, my manager interjected to take ownership for overlooking the error.

In this moment, my manager created a powerful precedent for our relationship: psychological safety. I felt empowered by the freedom to fail knowing that someone with influence was in my corner. This was just one of the many things a great manager did to gain my trust, in addition to:

• Asking me what he could improve twice as often as he critiqued me
• Trusting me with 10% more than I deserved so that I could accelerate my growth
• Taking ownership for my failures and boasting about my successes
• Pushing me to the forefront of conversations with leadership to add credibility to my name
• Advocating for promotions and opportunities unprompted

And I'm sure you have experienced the opposite as well. I've had managers that took credit for others' accomplishments, managers who hired carelessly and left their team to deal with the consequences, managers who used one-on-ones exclusively to complain about other team members, and so on. Most people know the struggle of a bad manager all too well; you deserve a great one.

"I failed to recognize the relationship with my manager as bidirectional"

Especially early on in my career, my main focus for weekly checkins with my manager was to demonstrate how much value I'd created for the company. I would rattle off a list of completed tasks and ask for guidance on prioritizing the remainder, never considering that the conversations goes both ways.

As I moved up in the company, I started to recognize that my work was part of a value exchange that isn't limited to just compensation. Ask yourself this: "I'm meeting your expectations, but are you meeting mine?"

If you expect to grow into a higher position with a certain timeframe, ask your manager to communicate a clear growth plan for you. If you are working on projects that help the company but leave you unchallenged, push your lead to design their roadmap around your interests. In your day-to-day, your manager should help eliminate blockers, resolve difficult workplace relationships, push back on stakeholders, navigate stress, etc.

Your manager is not only there to evaluate your efforts, but to help you realize your greatest potential. For more on this, Julie Zhuo's The Making of a Manager gives some great pointers on how to structure one-on-ones to optimize bidirectional communication. 

"I dismissed the importance of securing professional advocates"

I'm an extreme introvert (an engineer who's an introvert, how original). Besides having a very limited social battery, the idea of networking has always felt exhausting and disingenuous to me. However, when I look back on the last few years I recognize that many of the career opportunities I've had have been made possible because of a connection.

My first encounter with a professional advocate was a coworker (several levels above my pay grade) that offhandedly mentioned one day that she would vouch for me if I ever needed it. I asked if she'd be willing to write a few paragraphs on the impact I'd had on her team and when it came time for my performance review, I attached it to my report with a request to be made senior. 

On the flip side, I've mentored people that randomly approached me in the lobby of hotel conferences, offered internships to students that messaged me on Twitter and had dozens of coffee chats with strangers who reached out on LinkedIn. Building a network of advocates has opened up so many doors. I still hate it - but for my fellow introverts - I tell myself that all it takes is twenty seconds of courage to ask for someone's time.

"I was not intentional about positioning myself to serve my goals"

There's a certain cognitive dissonance around goal-setting that arises when your day-to-day gets hectic. It can start to feel like you're sprinting and going nowhere all at once; how am I busy all the time and getting nothing done? If you relate to this feeling, chances are that you're missing intentionality.

As an example, I was excited about an upcoming effort to architect a new data model. I'm an engineer at heart, so being involved in designing systems that serve a large audience gives me instant fulfillment - but I took a pause. My goal for the year is to gain management experience, and doing engineering work makes me additive, not multiplicative. Against my initial desire, I stepped down from this project to pursue avenues that better serve my ultimate vision.

The tricky part is that we're often asked to do what we're good at, even if it isn't fulfilling or challenging. It's taken a lot of discipline on my end, but I try to take a conscious approach to picking what I work on. If I get asked to lead a time-consuming project, my first thought is usually whether it serves one of my goals for the year. The idea is to reverse-engineer the accomplishment by considering whether single tasks roll up to a greater target.

"I focused on providing value far more than receiving it"

When you put in the work to become a valuable asset to your team, you gain a level of confidence that comes with being recognized for that value. There was a turning point when this clicked for me: I noticed that my team's roadmap relied heavily on deliverables that were very specific to my unique skillset, and I saw this as an opportunity.

During this time, I was feeling under-appreciated because my manager would allude to my career growth but never put forth an actual plan. This wasn't my manager's fault - I had never explicitly expressed my frustration to him, and you can't hold people hostage to expectations that you haven't communicated.

It resulted in a discussion where we amicably debated whether I was ready to take on more responsibility. We disagreed, and I took a firm stance that staying in the same role was falling short of the expectations of value that I had from the company. It was a risk, but it forced us into a discussion about why our perceptions on value were misaligned.

Now, I'm not saying go tell your boss to promote you or you'll quit. I made the mistake of allowing our relationship to get to that point by withholding my needs. To avoid this, I should have had more frequent touch points with my manager where we evaluated whether the company's reality was meeting my personal expectations.

Part 3: Boundaries

"I tolerated a toxic work environment"

We've all been there; as the saying goes, "when you know better, you do better". Well, I didn't know any better.

I've been blessed to work with kind and positive people for a large majority of my career. Toxicity has definitely been a rare interruption to an otherwise smooth ride, but it's given me a lot of wisdom nonetheless.

My first experience with a toxic work environment was an unfamiliar feeling of humiliation. I was part of a team that had a product manager, whose ambition I still have great respect for, though we ultimately could not function together in a healthy way. This product manager (let's call him Paul) decided that everyone working on this product should provide anonymous feedback on one another outside of the formal performance review process set out by HR. I found this odd because Paul was not the manager of anyone working on the product, nor had he spoken to any of our managers about doing this. However, I was a junior member at that time and wasn't sure if my discomfort was valid.

The day after submitting our feedback forms, I arrived at the office a few minutes early and found that Paul was reading my feedback forms aloud at a table with two other members of the team. Neither of these people were my superiors; they had been chosen because Paul trusted their opinion.

This experience was incredibly demoralizing. I felt embarrassed that my coworkers had appointed themselves to a position of superiority by handling something as delicate as feedback in a group setting, and that they had imposed a power dynamic to which I had not consented. This is just one example, but I spent six more months on this team with incident after incident until I eventually pleaded with my manager to move me to a different team (which he did).

Looking back on this time period, I have many regrets. Not only did I not speak up for myself or others, but I allowed it to escalate to the point where my husband was required to endlessly support stress-fuelled meltdowns at home. If I could go back and tell myself one thing, it would be: there are a finite number of hours in the day where the best version of you can exist, don't let work have all of those hours.

"I allowed others' lack of boundaries to shape my own"

I've been on both ends of this lesson. It's human nature to default to reasoning that other people should think and feel exactly as you would. Meaning, if I reply to work emails after hours, I may unreasonably expect my coworkers to do the same.

The reality is that there is no single right answer. For some, career is the number one priority and they are able to find great success with this approach. For others, work comes second to family or personal pursuits. The problem only arises when we expect everyone to have the same boundaries.

I once had a coworker ping me about a (relatively unimportant) product update during his wedding rehearsal on a Friday evening. On Monday morning, he posted to a public channel that the project had been delayed because I had not responded in time. He may disagree, but I have a boundary that others' lack of planning does not translate to my sense of urgency. I shared the situation with my lead, who was able to deescalate and distance me from this person.

I view boundaries like a muscle; you have to flex every so often or you'll lose your ability to exercise them. My recommendation is to develop a strong personal philosophy on the role that work plays in your life, and set boundaries that foster these ideals.

"I accepted others' unhealthy opinions as fact"

Toxic environments are difficult to navigate because you're essentially required to come up with a solution for a problem you did not create. What's wilder is that these teams often pride themselves as being 'resilient' simply for enduring their own culture.

There was a woman I used to work with that constantly shocked me with her unreasonable behaviour. I felt that she intentionally misrepresented my analyses in order to shine a more favourable light on her work, and this caused our interactions to become tense and awkward. I'm glad that this blog post is coming a few years after this experience because in hindsight, I'm able to recognize that she was under immense pressure to generate positive results. I empathize that she was thrust onto a team that had been operating under unachievable standards for years before she even stepped into the picture.

With this understanding, I was able to:

1. Recognize that I don't have to entertain unhealthy behaviour simply because someone else is generating a venue for it
2. Free myself from the stress of making sense of nonsense 
3. Disengage from the face value of the conversation and take a step back to tackle the root of the problem

I had to grow out of the habit of accepting unhealthy opinions just because they were delivered with conviction, and I've learned the hard way that empathy goes a long way. People don't adopt their perspective for the sake of it; there is some reason that they have chosen it. It doesn't make their actions justified or fair, but gaining some understanding gives you a path forward instead of just something to vent about.

Closing thoughts

Curious to hear what you think. What are the most important career lessons you've learned the hard way? As always, would love to hear your thoughts and feedback in the comments below.