SURVEY! SURVEY!
Looking forward to hearing from you about the new format of the newsletter. Tell me here! 👇🏻
We love to believe that treating our startup like a family means they will protect our careers when they finally scale.
That is the biggest lie we swallow in this industry.
If you are a Software Engineer and you are looking to navigate corporate growing pains without sacrificing your own growth, then this email is for you.
I want to tackle the brutal reality of the startup honeymoon phase in The A-Side. We will break down what happens when your company scales beyond a thousand people and why your career suddenly stops being their priority.
To complement that reality check:
The Read-Only Memory: Simon Sinek’s personal wake-up call about faking professional happiness.
The Open Thread Club: Rethinking your baseline loyalty to the company when AI anxiety creeps in.
The Rendezvous: Upcoming November engineering summits in Barcelona, Lisbon, and San Francisco.
Before you continue, if you enjoy my work and would like to support the newsletter, I’d really appreciate it if you shared it with a fellow engineer:
💚 On WhatsApp | 💙 On LinkedIn | 🩵 Bluesky
Or simply forward this email to someone who might find it useful.
The Read-Only Memory
Today, I bring you Simon Sinek. This person has a book I would like to recommend (I’m not getting paid for it)
— Simon Sinek
The story that I bring you today is very related to the topic you will read in The A-Side (down in this email).
When his first company seemed to be doing reasonably well, a friend was the first person to notice that something didn’t add up. Sinek admits that he had been pretending for some time to be happier and more successful than he actually felt. It was that conversation, not professional success, that enabled him to start changing his life.
Did this happen to you?
In this section, we will focus on biographies of computer pioneers, forgotten historical whitepapers that remain entirely relevant, and independent blog posts that question the status quo of our industry.
Would you like to suggest some? I hear you! 👇🏻
The Open Thread Club
Following up on the main topic of The A-Side today (read down in the mail), I don’t bring you a question from readers. Not because I don’t have any about this topic, but quite the opposite, including concerns about “I’m worried about the AI taking my job”.
Today, I bring you something I wrote some time ago, so:
Instead of worrying about “will the company fire me?”
Just think, “What should be my position in regard to the company I’m working for”
Read the full email here 👇🏻
In this space, we will address real dilemmas about architecture, technical friction, or leadership situations sent anonymously by you.
Instead of giving theoretical or dogmatic answers, I will respond with honesty, sharing my own past mistakes in similar situations and the lessons I took away when trying to solve them.
You can start participating RIGHT NOW! Click the button below and tell me your story so I can answer in the next issue 👇🏻
The Rendezvous
From now on, you should start targeting summits and conferences happening in November, so I can bring you 3 during that month.
The PyConES 2026 is happening in Barcelona (Spain) next November 6th to 8th.
In Lisbon (Portugal), the Web Summit 2026 starts November 9th and ends on the 12th.
If you are in the San Francisco area (USA), you will have the QCon San Francisco 2026 from November 16th to 20th.
If you attend some of those, tell me how it goes!
A radar of events about software engineering and technical leadership.
The priority here is not to be exclusively massive conferences, but to give visibility to smaller, local encounters or emerging initiatives. If you are organizing a conference or know of an event worth sharing, the channel is open for you to send it to me and share it with the community.
Do you own an event or summit? Drop me an email! 👇🏻
The A-Side
Every developer starts in the honeymoon phase.
When a startup is small, say under 500 people, it’s easy to feel that your work really matters. You know the people around you, you can see the impact of what you’re building, and you’re close enough to the company’s mission to feel part of it.
Motivation is high. Sometimes very high.
You might even find yourself going the extra mile, working late or taking on more than you probably should, because you genuinely care about what you’re building.
Then the company grows. 800 people. 1,000. 2,000.
More layers of management appear. Teams get reorganised. Processes multiply. Decisions take longer. And at some point, you hear someone say:
This isn’t what it used to be.
— You team mates, in the coffe break
It’s tempting to blame the company. But most of the time, it’s not that simple.
As a company grows, the way it operates has to change. The focus shifts towards products, revenue, efficiency, organisational goals and, increasingly, doing more with less. AI is only adding more pressure to that equation.
And somewhere along the way, your individual career can stop being a priority for the people at the top.
That doesn’t necessarily mean your manager doesn’t care. They might care a lot. They may simply have 15 other things competing for their attention and very little room to protect your interests.
👉🏼 So be careful about where you put your extra effort.
There’s nothing wrong with caring about your company. But your career is ultimately yours.
Put some of that extra mile into your own skills, your own projects, your network and your growth.
Because when the company changes, restructures, or moves on to its next priority, those are the things that stay with you.
👉🏼 Invest in yourself first.
If you want more honest thoughts on navigating engineering careers, Tech Lead roles, and the path towards Staff Engineer:
Read the full list here → https://newsletter.optimistengineer.com/t/tech-lead
Be safe,
Marcos