The truth is, the greatest architectural failure was not in code, but in my career path.
I carried the title of CTO (Chief Technology Officer) at 21. It sounds great, because you're able to select the technologies a company uses, you're an executive and you manage client relationships.
But internally, my CPU was at 100%. I was the solo founding engineer sustaining the product. I had to be a generalist in every single domain:
- Frontend
- Database Optimization
- DevOps
- Backend
- Client PM
The context-switching, multi-tasking and lack of proper management experience or a technical team turned the position into a bottleneck. The problem was never the position. The problem were the conditions and responsibilities that came with it and I was not prepared for.
I'm still coding and delivering results, but I'm no longer the former CTO I used to be.
Let me share with you the 5 most important lessons I could've learned during this journey of almost 1 year.
1. Map your capabilities to your aspirations
Before you can build anything great, you must survey the land. I failed to do this.
I was too focused on the business results and outputs (features, deadlines, metrics, etc) that I was neglecting my own skills. I didn't know IaC (Infrastructure as Code), proper Networking or scalable Systems Design. The "CTO" role was nothing but a mask to hide those gaps from others, and more dangerously, for myself.
Your career is a system that needs maintainance. Audit it regularly. Be honest about the gap between your current skills and your future goals.
Think of it like climbing a mountain. The title is the summit.
Most people believe you have two choices:
Bare Hands: The brutal and manual grind. You fight for every inch of ground through sheer force and overtime.
The Helicopter: The smart, strategic path using the right tools and skills.
This is a lie.
The truth is, you use your bare hands to build the helicopter. I was so exhausted from the manual labor of firefighting and solo-coding that I never stopped to actually build the vehicle that could lift us to new heights. I was stuck in permanent manual mode, confusing hard work for smart progress.
Don't just climb with your hands. Build the damn helicopter.
2. Specialize to scale
Before we talk about specialization, let me ask you something more revealing than what programming languages you know: What are your hobbies?
Mine is music composition. I'm obsessed with it. In music, you don't just throw notes together. You use music theory, a structured system of rules and patterns. You make changes through careful voice leading, ensuring each note moves smoothly to the next. You work within constraints like scales and tempo to create something beautiful and coherent.
I realized I don't just love music; I love the architecture of music. (I'm a music theory nerd, too. 🤣)
And that's why I'm specializing in backend and cloud engineering. The backend is the music theory of software. It's the hidden structure that makes everything else possible. Cloud engineering is the orchestration, ensuring every service is in tune and in time.
This doesn't mean I can't do frontend. I can. Just like a composer can learn to paint, it's a different skill. But I'd rather be the one writing the symphony than designing the concert poster.
I want to build systems that scale and grow without me.
Specialization isn't about closing doors; it's about mastering the architecture you're truly passionate about building. It’s the difference between playing every instrument and becoming a virtuoso of the one that speaks to your soul.
For me, that’s the symphony of systems.
3. Growth over titles
Let's be honest. You're a 21-year-old CTO at a startup. It sounds impressive.
Now imagine you have to sit down and negotiate with other CTOs. They're discussing microservices, Kubernetes, CEO negotiations, hiring strategies, scaling to millions, and complex systems design on AWS.
And it all sounds like buzzwords to you.
This exact scenario is why I quit.
Not because I was scared, but because I was strategic. I saw two paths:
The Ego Path: Stay in the room, fake it, and slowly be exposed as inexperienced while my actual technical skills rust.
The Growth Path: Leave the room, admit what I didn't know, and go build the skills to earn my way back in authentically.
When you're starting out, you must prioritize your growth, not your title. It's great to learn from other CTOs, but not at the expense of your technical foundation.
You're better off monetizing a SaaS, being a freelancer, or excelling as an engineer at a company where you can learn new tech.
Specialize. Grow. Learn.
Don't try to be a pro F1 driver when you're still learning to drive a kart. Get proper training first.
4. Find a team and mentors
I'm done being the solo engineer.
I'm done guessing. Done sending pull requests into a void, with no one to question my decisions or suggest a better way. Done being unaware of the teamwork and best practices that transform good code into great systems. This isolation probably even stunted my Git skills. When you only answer to yourself, you never learn the true power of collaboration.
Don't be the only technical person in the room unless it's your own venture. Even then, it's a temporary state, not a sustainable strategy. Solitude is a career liability that only limits your knowledge.
That's why I'm joining a team at work. To immerse myself in code reviews, architectural debates, and shared ownership. I'm also studying Web Scalability for Startup Engineers. This is the book I wish I'd read before writing a single line of professional code.
It's the book that would have taught me that scaling isn't a feature you add later; it's a property you design for from the beginning.
It's never too late to stop being a one-man band and learn how to play in an orchestra.
5. Burnout and mental health
Protect your mental health, relationships, and happiness at all costs. No equity or title can buy your freedom.
I'm focused on growing and learning now, not managing. Rest. Accept that it's okay to not know everything.
The moment your heart stops choosing something, even though your mind has rational excuses, it's no longer for you.
Whether it causes trauma, breaks you, or holds you back; let it go. Your most important system is the life you build.
Conclusion
A lot of people say I need therapy.
They misunderstand. My choice to leave wasn't a cry for help, but a declaration of independence.
Look:
Therapy doesn't build resilient systems at 3 AM.
Therapy doesn't master cloud infrastructure or elegant code.
Therapy doesn't deliver the profound satisfaction of creation.
I found my therapy in building. In the logic of systems, the flow of music, and the confidence that comes from genuine mastery.
They see a former CTO. I see a builder who finally learned that the ultimate scale is a life of freedom, surrounded by family and friends, doing work that matters; on my own terms.
The title was a cage. The freedom is the system I'm building now.
(In case you're wondering, I didn't quit. I'm a Backend and DevOps Engineer at the company now.)
So, what do you actually want?
Not what your resume wants. Not what your ego wants. Not what other people think you should want.
I know what I want. I want to build apps. I want to be with my people. I want to deepen my backend and cloud engineering skills. I want to contribute my knowledge, mentor others, educate myself and own my time.
I want that more than a place on a cap table. More than chasing investors. More than a fancy title that costs me my freedom.
The title was a lesson. The building is the reward.
Now it's your turn. What do you actually want? Share your "Path" in the comments.
Top comments (12)
I’m so glad that I didn’t skip a sentence.
The clarity of your narration is incredible. I admire how you express different opinions about your evaluation of your role as CTO and how you felt (or realised) your skills weren’t really flourishing as you’d expected it would with the role.
And I did take my time to go through the comments too. Trust me, I picked a few lessons from your writing and the comments too. 👏
Now, I have to go back to myself and ask myself WHAT I really hope to achieve with the skill that I’m learning, and the kind of environments/roles that I want to put myself (and the skills) in.
Astonishing decision Francisco, people like you remember me that progress stall when we decide others take decisions for use and we only are obedient for the rest of our lifes becuase the initial deal was shiny for our young minds.
You're right, Klinker! Sometimes our young minds are attracted to things it's not prepared for. This taught me I need to keep improving my technical skills and soft skills before trying to get into a similar role in the future.
We want to build from a foundation, not in a reactive way.
Super-honest read. The idea of racing to the title without building the foundations really resonates, thanks for sharing this.
Thanks Joseph! We need to build a strong foundation to keep growing in our careers! Glad to see you learned something new from this blog post :)
While I think you come of as a person who has a good head on your shoulders. The main thing I was thinking is were you really a CTO?
From the post I get that most of the time you were a single developer. In the beginning you listed four technical skills and one business skill. I think the skill list of a CTO is more evenly split between technical and business.
I think a freelancer is more a CTO than you were.
One of the things I think are crucial to be a CTO is leading. Because you were a single developer, you only lead yourself. It can be difficult, but it doesn't compare to people who lead tens or hundreds of people.
I think they lured you with the title to make you work harder than you should. But you were smart enough to take away things from that experience to do the work you love.
The hardest critique is self critique, and it is how you advance as a person.
Thanks for the comment, David! Legally, I was a CTO. By role, as the company is still new, I wasn't executing CTO functions as a whole such as hiring, leading teams or handling budgets. I was delegating people and supporting the business. Ultimately, the role was more of a condition given by the company just to "reward" my work. However, I knew that I was also going to be an actual CTO but with the skills of a mid/senior developer and no proper management experience with teams.
Hence why I decided to prioritize my individual growth and keep mastering backend development. If I'm leading teams, it'll be from learned experience and mastery. Not in a reactive way when I was firefigthing the whole stack and it limited my growth.
Thank you for the clarification.
As you mention you were given the title, but not all the responsibilities.
For me a CTO is more a manager than a developer. A CTO doesn't build a resilient system at 3 AM, they instruct the people to build the system.
I don't doubt you were given the title, my doubt is with the company and if they knew what the weight of the title is.
Like developers learn to build for the realistic scale, companies should not hand out titles that don't fit their personnel structure.
From your post and your comment, I think a more fitting title would be technical lead.
Yes, a CTO is more of a manager for me as well. The CTO title, particularly in a young startup often serves as a recognition of dedication and initial technical ownership more than a reflection of a scaled management role.
I knew I needed to step back and master backend development or another specialized area before I could lead an entire team.
My current focus is precisely on becoming that Technical Lead/Senior Engineer but from a position of mastery. Thanks again for the valuable perspective! I'll keep working towards that true leadership role.
I can see that perspective, but I think it hollows out the title.
When the hierarchy of the company is flat, what is the case in most small companies, I think titles are useless.
It might be good on your resume, but it is more fluff than anything else.
Right. Certainly titles are not really useful in small startups. I'd always prefer to use "Founding Engineer" over CTO in my resume. Even though I was something different legally. 😅
Thanks for all the comments David!
i experienced these in several ways in my life too: when you are being paid very well, and others expectation did not match up, you will not last long and relationship with boss or peers will not match. or when you in sales oriented environment, and you constantly provide support for customer for free (as a presales engineer), likely the boss will terminate your role very soon. or when you constantly like development, but the boss need you to be in a project management mode to delegate the role instead.