Expensive Lessons That Accelerated My Tech Career
How Expensive Mistakes Become Growth-defining Lessons
🔥📖 Last chance to join the FEARLESS book club in August. We kick off the first video Monday night. DM me FEARLESS if you want improve the psychological safety of your team’s work environment. You will improve your book-reading skills with the help of speed reading tips and an accountability group.
Today’s Crafting Tech Teams is about Denis—notably all the big mistakes, company-wide and personal ones that I was a part of and how they shaped my career. I resisted seeing positives in the painful experiences throughout my career. Especially the ones that become personal at the apex.
But over time life escalated messages I refused to learn, resulting in new paths. Each closed door opened three new ones. Here are my big moments of hardship, imposter syndrome, anxiety and hard lessons:
2008, ??€—Mobile Video Streaming Research as a student
I got tasked with what seemed an impossible challenge. I was 18, inexperienced and way over my head. It was a summer student job.
I had a strict, but benevolent supervisor. It was my first ever programming job that I was paid for. I felt very grateful, but also very proud. I struggled asking for help. I tried to grok everything and make a good impression by solving everything on my own but got 0/10 on human connection.
The organization was about 20 people, but I had no interactions with anyone. It was me alone at my desk with a weekly brief with my supervisor.
It was tough. I got to a point of building a prototype. It seemed promising. But then I hit a roadblock. And got stuck on that roadblock for 4 weeks. One afternoon, they asked me to leave my computer and project files unlocked and take an early leave.
I knew what that meant.
Lessons learned: I don’t work well in a solo environment, surrounded and distracted by an entire department working excitedly on something else. I constantly wanted to join their discussions, help them out. I saw they got value from that. But I didn’t speak up on this as I didn’t know how to navigate a the political, inter-department landscape of the workplace. Setting up communication channels and relationships with my manager became a top priority from that point onwards. It was possibly the most useful learning experience to bootstrap my career in tech.
2009, 35.000€—Unexpected Cloud Bill
I earned my stripes in the advertising space. Before AWS, before Azure and way before Google Cloud got traction in Europe there was Adobe’s Flash Media Server. It is archaic to today’s standard, and back then it wasn’t any better. This was my first experience with “serverless” before that term even became a thing.
The context here is a typical example lacking serverless and cloud know-how. We had a culture of on-premise hosting that we rented out as a service to our clients. This created a work ethic where we had a cheap dev server we owned locally that we could abuse and expensive hardware racks for our paying clients.
The typical process was test it on the cheap server. If there are performance issues, it may be because the cheap dev server can’t handle it, so to a test run on production and optimise if necessary. This was considered quite lean and gained a lot of praise from management.
My supervisor picked the tech stack. I had no experience with FMS but was quite excited to see what it’s like writing actionscript/javascript on the backend for a distributed product. Naturally, I applied the same performance-ethic.
What went wrong: What I didn’t realise is that our product couldn’t be tested locally. So we rented a second VPC for testing purposes. You can imagine where this is going. Make it work, test functionality, then improve performance if necessary. However, the various automated tests and data migration conducted to perform them acrued so much additional charges that we were surprised to learn that Adobe was billing us 35.000€. The project was worth 45k. I was 20 years old at the time and this was by far the biggest gut-wrench I’ve experienced professionally.
Lessons learned: Vet all new technology, especially the shiny ones you don’t understand. I assumed my manager would do it because it was out of my responsibility area, but this experience has helped me realise sometimes they get overwhelmed too and require support or just a nudge from their team.
Where we got lucky: I thought everyone was going to get fired. My heart sank as I learned of this on our company-wide briefing and felt personally responsible. I won’t forget what the CEO said to me personally after seeing me pale faced: “We all made mistakes here, it wasn’t just your fault. It’s a 35k lesson. Now let’s work on getting the project back on track.“ That conversation taught me more about leadership than a dozen books.
2011, 10.000€—The Cost of Not Speaking Up
My first tech lead and leadership role. I was being groomed to take over a team. There were some red flags early on in the project. I didn’t know how to communicate them and felt uncomfortable being the troublemaker.
We survived the recession by restructuring some teams. We lost a lot of good people and ended up understaffed on a few projects. Once that was dealt with, new clients started to trickle in but it wasn’t enough. The company was desperate for more business.
Two projects landed on my desk. Contract written, roadmap set, features listed in bullet points. The team wasn’t consulted. I wasn’t consulted. Budget seemed tight. So did the deadline. Obvious only in hindsight—a crucial, critical payment integration was hidden buried in fine print. I was about to say no.
“Denis, your team needs this project.”
I hesitated.
I said this doesn’t seem like a good setup. They claimed if there’s trouble they’d help. There was trouble. They did. I asked them to manage as I was out of my depth. They helped, but the mess ended up being my responsibility. I thought they’d handle the project since I was obviously out of my depth and overwhelmed.
It was a shit show.
Lessons learned: Trust your gut. There is no immunity for leader-in-training. I was in charge, it was my responsibility. I let my team down by not fighting for their best interests when my spider senses signalled red flags.
This kind of internal competition is surprisingly common in startups and agencies, which I only learned after a few years. I left and joined a more corporate environment.
2014, 40.000€—Unhealthy Environment, Fighting for Resources
The environment at work became increasingly toxic as we grew. I contributed to this as well by pursuing my career goals very aggressively. I found out what happens when you butt heads with senior management on product, architecture and end up having to fight over the roadmap budget.
We were setup as a well-oiled feature factory. Large, transnational corporation with a centralised, off-shore software shop. 💩 Technical debt was the biggest stink in the back of everyone’s mind. Leadership was very hustle-oriented and reminiscent of work cultures you’d expect at JP Morgan or Apple in the 2010’s.
There was an irksome culture of The Emperor's New Clothes where we were required to present everything in an idealised, fabricated manner to hide any imperfections. Especially when our investors were on site handling a high stakes project.
The downstream consequence of this behavior was a repetitive cycle of optimistic roadmaps and extremely late delivery (sometimes years late!). This was then handled by overtime, mobbing and pressure. This caused a lot of turnover.
Equipped with my newfound wisdom, I set out to change this situation by being very liberal and transparent with my team’s performance. I was quite strict on enforcing the deadlines were realistic and honest. I urged the the plan to be constantly addressing the surprises we know oh so well to avoid overtime, especially since it was unpaid.
However, I was still too young and naïve to realise that this culture was part of company values and my manager had full support from senior management to run a tight ship with an iron fist.
I reached out for advice and was suggested doing a skip-level with my boss’ manager. I didn’t handle that very candidly and it backfired, resulting in more harassment.
Lessons learned: Have all formal requests and disagreements in writing. If on-call or doing overtime, have clear expectations. Empower the team to handle on-call with a “will it work at 3am” mentality. Leave a company if there’s a clash of culture and values. Don’t fight an uphill battle trying to change such an environment.
Despite all the emotional turmoil, I was glad to have this experience. It exposed how ill-equipped I was to manage office politics and intra-department relationships, which set me up on a path of self-discovery and introspection.
I also took the lessons from the previous job to heart and stood up for my team. This created a strong bond of trust and respect, building a strong culture of loyalty and belonging. This was a blessing in disguise as many of my reports and other team members in the department joined forces with me later at other jobs and we ended up creating a strong high-performance culture that carried over to many companies and products.
2015, 15.000€—Prioritising Complex Problems over Customer Value
I entered the startup scene. The sheer chaos was quite overwhelming at first. I comforted myself in the structure of long-term, complex problems. Unfortunately, being busy also masked more pressing customer concerns that ultimately required an expensive pivot.
I hindsight, I now realise this was a typical case of divorced product and engineering departments. Likely only one person understood the value of the business’ core product to our users. Everyone else, including my department, was solving seemingly adjacent, complex issues from a never-ending backlog.
The CEO was quite transparent about our financial issues after the recession, yet no one in my department thought that the engineering team could do anything about. Oh how the tables turn!
We were constantly chasing our tails creating overfitted MVPs while the product owner tried to extract product market fit from our tech sprints as if it were a never-ending hackathon.
Lessons learned: I discovered and ignored a new kind of red flag: We had more managers and departments than ICs. There were VPs of this and VPs of that in a 40-man company and a bunch of 2-people departments. This seemed romantic at first, promising a future of hyper-growth—but it made everyone miserable as it never occurred.
Faux-process and fake agile only get you so far when discussing the reality of the product’s market-fit is an uncomfortable topic that is avoided. Seek product-related discussions as a priority, especially during onboarding—rather than jumping straight into cost-optimisation.
2018, 47.000€—Pivot, Company Turmoil After Forced Leadership Change
Everything seemed to go well except for certain blind spots. We had the problem of deadly silence—a sign of lack of psychological safety. The company was scaling fast and it fell under the radar, until everything imploded seemingly overnight. This left a couple high-stakes projects unmaintained and understaffed, requiring company restructuring and expensive pivots.
We had one thing working for us: the initial team was one of the best cultural fits I’ve ever seen. Unfortunately, the company also had two separate offices that worked asynchronously and didn’t collaborate all too well. This created a schism between the employed vs. off-shore/contractor groups that ultimately spiralled out of control.
The big benefit of having an independent, autonomous and very experienced group of professional contractors also created the main problem: lack of oversight in salaried leadership positions as the company grew 5x. Add to it the ICO turmoil from the crypto economy at the time and you have another nice cooking pot of lessons for Denis.
Lessons learned: When the official organizational structure is loose, err on the side of taking confused members under your wing to provide them with support. The mantra of fast paced, repetitive deadline-chasing that erodes relationships is a sign of confusion and panic, not industriousness and meticulous execution.
Good cross-department relationships and earnest onboarding provide much more business outcomes than one well-performing project. Humans first.
2020-2022, 37.000€—The Cost of Overcoming Imposter Syndrome
After going solo I struggled a lot with getting out of my comfort zone. I had to let go of relying of the safety of long-term employment. I required the calm and focus necessary to focus on building a business, not working in one.
The numbers you see above are the total I’ve invested into training, coaching and business acceleration. It’s not that they weren’t useful. But the order and intensity of them had me applying less than 2% of what I learned. I needed to let go of doing and focus more on creating.
Lessons learned: Ironically, becoming a father of two blessed twins was the call-to-action that really got all of my distractions off of my schedule. It was the extra bit of act-of-service and family focus necessary to get me inspired to better myself and pursue a bigger cause.
I spoke about my journey in depth in my conversations with Jonathan Stark (part one below, part two here).
