I cried three times at work in my career.
Feeling Like an Imposter
The first time was a few weeks after moving from Italy to Hamburg.
I already had eight years of experience, but it was my first role in mobile development, on an international team, surrounded by younger colleagues who all had computer science degrees, and had apparently been coding since they were teenagers.
I had switched careers late, was a self-taught programmer, and I constantly felt like I was behind.
Every daily/stand-up felt like a reminder that I was slower, less confident, less technical. All these agile ceremonies were new to me, coming from an enterprise with strict waterfall processes, and having to speak English in front of such a big team, ~15 people at that time, was torture.
One afternoon, I stepped out onto the terrace, called my wife, and broke down.
I told her everyone would soon realize I was an imposter, that I wouldn’t pass probation, that moving our family 1,200 km had been a mistake. We would have to move back, facing the disappointment of relatives and friends, and losing money with rents, relocation and schools.
Of course, none of that happened.
After a shaky start, I found my rhythm. I learned, adapted, and eventually became one of the top performers in the team. But I never forgot how that fear felt, how real it was in the moment.
The weight of expectations
The second time I cried was after a round of layoffs.
Many roles disappeared overnight, and those of us who remained had to fill the gaps. I joined a new team, arguably the smartest engineers I’ve ever worked with, working on backend and cloud systems.
And once again, I felt completely out of my depth.
I didn’t understand servers, routing, or half of what they were building. I could barely follow their conversations about monitoring or infrastructure. I was proficient in ActionScript ( remember, Adobe Flash? ) but that team was building tools and services in/for Unity, Java and HTML5 and everyone was so confident in jumping from one language to the other in a matter of minutes.
So one day, sitting in the office bathroom, I called my wife again and cried. I felt useless and guilty - guilty for keeping my job while others, perhaps more capable, had lost theirs.
But this time too, I didn’t run away from discomfort.
I stayed late. I studied. I asked questions that made me feel dumb. I endured harsh code reviews.
And slowly, eventually, I became one of the company’s go-to people for TypeScript and Serverless.
Facing my own leadership blind spots
The last time I cried was soon after becoming a Technical Lead/Engineering Manager.
I had a team I genuinely cared about, and I believed I was doing well. I’m driven, fast, curious, and direct. I value clarity and high standards, and I’ve always tried to lead with honesty and enthusiasm.
Then, during a 1:1, I received feedback that my energy and speed were intimidating people, that my drive was actually demotivating some team members.
I froze. How could my best intentions land so wrong?
I thanked the person for the feedback, ended the call, closed my laptop, and cried. Out of confusion and sadness.
I became a leader to inspire and empower others, to be the leader I once wished I had. And here I was, learning that my approach, while well-meaning, was having the opposite effect on some.
That feedback taught me something profound:
intent does not equal impact. And as leaders, we are responsible for both.
Discomfort vs. Danger
That hard conversation pushed me to start reading about Nonviolent Communication, Psychological Safety, Accidental Diminishers, Radical Candor, and many other frameworks. Once again, leaning into discomfort taught me a lot.
But over the years, I’ve started to notice some patterns that still confuse me. I’m not sure if they’re generational or just individual differences, but it often feels like our collective understanding of safety has become blurred with comfort.
When someone challenges us, holds us accountable, or pushes us to grow, we sometimes label them as “toxic” or “psychologically unsafe.”
But there’s an important distinction we often forget: discomfort is not danger.
Danger means harm, disrespect, humiliation, exclusion, abuse of power.
Discomfort, on the other hand, is that tension we experience when we’re stretched beyond what’s familiar.
Not every disagreement is abusive, not every negative feedback is disrespectful.
And while I often hear people talk about courage in these situations, I’ve never really felt courageous. For me, it’s less about bravery and more about acceptance — learning to face hard truths, to sit with uncomfortable feedback, and to take responsibility for my own growth, even when it stings.
Real growth doesn’t come from ease. It happens when we choose to stay present through discomfort, when we listen to feedback that hurts, when we admit we’re wrong, when we hold each other accountable even when it’s tense.
Every time I cried, I didn’t break. I grew.
Not because things got easier, but because I decided to face what felt impossible.
Vulnerability and Trust
That’s also why I chose to share such a personal story. Because trust and vulnerability go hand in hand.
When we allow ourselves to be seen - imperfect, uncertain, emotional - we make it safer for others to do the same.
When we’re transparent and honest about our shortcomings, we create space for empathy and trust. We show that it’s okay to struggle, to not have all the answers, to need help.
When leaders, or senior engineers, show vulnerability, it gives everyone permission to breathe, to be human, and to keep growing. We’re all learning, at every level, in every role.
Imposter syndrome doesn’t vanish with seniority; if anything, it often grows stronger. The more experienced we become, the greater the fear of being exposed as a fraud, the harder it becomes to ask for help, or to admit we don’t know something.
This kind of openness builds stronger teams.
It transforms discomfort into connection, and accountability into shared growth.
That’s why I’m writing this.
Not to glorify hardship, and not to say that everyone should “toughen up", and not to say that crying at work is a rite of passage.
It’s to remind anyone struggling that you’re not alone.
A final thought
I’m incredibly grateful that, each of those three times, I had someone to talk to: my wife.
Having someone who listens, supports, and reminds you of your worth (or shakes you off of all the self-pity) makes all the difference.
So if you’re going through something similar, please talk to someone, a partner, a friend, a mentor.
And if you need to, reach out for professional help.
Because the goal isn’t to avoid discomfort, it’s to face it with courage, self-awareness, and the right support.
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