Ask HN: A Career Dilemma

[Shaun0]

I've spent several years at a small company, starting as an iOS developer and gradually expanding my role to cover frontend, backend, DevOps, and even product management. I eventually learned to write business proposals and handle various aspects of product development.

Now that I'm looking for a new job, I've hit a wall: most positions require deep specialization in specific areas, while my breadth of experience, though valuable, doesn't seem to align with market demands. My generalist background, which was essential in a small company, appears to be more of a limitation than an advantage in the current job market.

How do you navigate the transition from being a technical generalist to finding your place in a market that values specialists? Has anyone successfully made a similar transition?

[shw1n]

I had this problem in my recent search, very similar situation (early-stage startup, then founded two companies).

What yielded success was shooting for "Full-Stack Engineer" and "Product Engineer" roles

Surprisingly, while startups were particularly excited, a lot of bigger tech companies were too

But while shooting for "Product Manager" or "Backend Developer" or even "Front-end Developer" I got nothing, it was the "Full-stack" keyword that got me tons of interviews

[Shaun0 → shw1n]

Thank you for your insights! I'd love to hear your thoughts on choosing between companies/industries. While I'm naturally drawn to smaller companies despite the higher job security risks (risk/reward ratio makes sense to me), I've found that many startups lack the interesting work and open culture they advertise, and sometimes their business prospects are questionable. As for larger companies, they often seek technical leads with management experience, which creates a barrier for someone like me. How did you navigate this dynamic in your search?

[shw1n → Shaun0]

My personal thesis is some combination of Bezos’ “regret minimization framework” and working on “cool problems with the smartest people”

This job application cycle I encountered three tranches of roles:

1) Great WLB companies — fully remote, ~$200k salary, if slightly less exciting work

2) Big tech companies — typically hybrid, much higher salaries ($300k+), if possibly less WLB and more boring day-to-day work in service of an exciting larger goal

3) Early-stage — super exciting work, smart people, at cost of WLB, salary, and brand

Not having gone to a prestigious university, brand was a big factor I considered — esp for future fundraising and roles. Some of the big tech companies were also likely to IPO for some quick cash, and obviously had smart people there.

Having a family leaned me towards the great WLB roles too, but ultimately I went with the early-stage because life is just a pure joy when both the work and people are great.

Another reason is community. I lacked true peers/mentors much of my life until I joined a really solid early-stage with smart people, who became great friends. So when I sense a chance to recreate this experience, I jump at the chance.

[Shaun0 → shw1n]

I couldn't agree more with your breakdown! These three categories perfectly capture the landscape of most tech roles today.

Your point about the early-stage company experience particularly resonates with me. Like you, I don't have a prestigious university background, and what you said about finding true peers/mentors really hits home. I think most of us in tech struggle to find mentors who can provide genuine strategic guidance rather than just technical advice.

I'm also drawn to startups and the prospect of working with brilliant teammates. The energy and growth potential in such environments is unmatched. But finding these 'small but mighty' companies feels like searching for needles in a haystack - they're rare gems where everything aligns: smart people, exciting work, and good culture.

Just curious - when searching for these early-stage roles, did you have any specific strategies for identifying truly promising opportunities? And the trickier question... how did you assess whether you'd be working with genuinely smart people versus just well-practiced interviewers?

[shw1n → Shaun0]

I actually wasn't searching for early-stage, in fact I was explicitly looking for the opposite (brands for the resume)

But I accidentally signed up for YC's "work at a startup", and two great offers reached out to me via LinkedIn

For vetting: I've found I can usually tell within a conversation, how quickly someone gets to the core of their business, insights they have about new topics, and ofc some degree of accomplishments (not degrees or brands, but companies founded or tech they've built)

[WheelsAtLarge]

You have to pick a specialty and get certified. Certificates are the only way you'll be able to break into the field you want to pursue. They don't guarantee anything but for a hiring manager, they at least signal that the person has received training. Additionally, I would volunteer at work on projects that are specially useful towards your career path.

Going forward you'll need to start looking for jobs that will move you forward on what you want to specialize in. It won't be easy but eventually, you'll get something. Learn from every interview and get a better understanding of what employers are looking for.

Also. don't pick a specialty just because it pays well. Money is nice but remember you'll have to do your job for the rest of your career. Money will not make up for the mental stress of doing a job you hate.

[scarface_74 → WheelsAtLarge]

I have 6 AWS certifications. Certifications have always been easy to memorize enough to pass a multiple choice test and no one who hires thinks because you have a certification means you are competent.

Also I have been working for almost 30 years. My first “specialty” was writing C and Fortran for mainframes. Being in tech is all about pivoting

[mech422 → scarface_74]

>>Being in tech is all about pivoting

And remembering stuff 30 years later so you can be one of the last 10 people left that remember it. I figure COBOL should make a nice lil side hustle when I retire :-P

[Shaun0 → scarface_74]

I'm curious - how do you maintain the energy to learn new technologies while keeping your existing skills sharp? Don't you ever feel burnout or fatigue from the constant need to stay current? Would love to hear your strategies for sustainable learning in this field.

[scarface_74 → Shaun0]

> how do you maintain the energy to learn new technologies while keeping your existing skills sharp?

I don’t keep my existing skills sharp.

This was in response to another comment. But should give a little context.

https://news.ycombinator.com/item?id=42704502

By 2018, I stopped trying to be a “full stack developer”. I gave up on keeping up with what was going on the front end and start learning AWS.

I was the first technical hire by a then new CTO who was bringing development in house from a third party consulting company. I jumped on every AWS related initiative who threw at me and started leading them by doing proof of concepts and working with teams to establish patterns and processes.

Stepping back for a second, I got my first AWS certification without ever opening the console and my first six within the first year of opening the console. The purpose of them were merely a guided learning path so I would know what I didn’t know.

Between 2018 and 2020, I got a lot of hands on experience combining development + AWS.

A full time position working at AWS in the Professional Services (consulting) department fell into my lap in 2020.

https://news.ycombinator.com/item?id=38474212

While there, slowly I started being put on projects where I was over the DevOps “work stream” showing clients how to automate builds and deployments on AWS. A work stream is basically a smaller project in a larger implementation. I was a mid level (L5) “Cloud Application Architect” supposedly specializing in cloud architecture + application development. But it soon became DevOps + a few Python scripts. That means I started doing even less development and became hyper focused on one or two specific niches

I worked at a shit show of a third party cloud consulting company for a year doing the same thing and now I work as a “staff software architect” at a much better third party consulting company.

I come into a project right after sales and validate the business requirements, current state, desired future state and then work with the client to propose a high level technical design and implementation plan. We as a company get paid for giving the client an “assessment”. They can either take it and run with it or have us do the work.

At this phase, I have to have a broad enough understanding of the AWS ecosystem to know what questions to ask and how to implement what they need in broad strokes and ask the subject matter experts at our company in areas that are not my strong points.

In other words, I don’t need to be the best developer, data analysis, cloud engineer, etc. I just have to know the specialties well enough to talk the talk.

Part of the assessment is breaking down the projects into “work streams” - sub projects based on specialties. If the client wants us to do the work, I then turn into a tech lead and assign the work streams to “architects” who are the hands on specialists. I for the most part defer to their technical expertise and they are responsible for leading their work streams and working with the client to make sure their work stream is done. My job is to coordinate the architects, client, sales and project managers.

My hands on skills may not be as sharp as they were. But I spend my down time learning and staying abreast of industry trends. I use getting certifications mostly as a guided curriculum to force me to keep learning. It’s not for resume building.

The next logical question is what happens if I need to work as a hands on software developer or God forbid a “cloud engineer”? I have a year’s worth of expenses in the bank aside from retirement savings to give me the runway to get interview ready.

[Shaun0 → scarface_74]

Wow, thank you for sharing such a detailed and honest career journey! I really resonate with what you're saying about shifting focus to becoming an expert rather than trying to stay sharp in everything. The pressure to 'know it all' can be overwhelming, but as you've shown, doubling down in one area can actually open new doors and create opportunities.

I'm on the fence about the certification learning approach you mentioned - not sure if it would work the same way for me, but it's interesting to hear how you used it.

Your point about building financial runway is incredibly helpful - definitely something I'll keep in mind when planning long-term career moves.

Thanks again for sharing your insights and perspective!

[scarface_74 → Shaun0]

> I really resonate with what you're saying about shifting focus to becoming an expert rather than trying to stay sharp in everything

I’m honestly not sure I am the “expert” anymore. The different specialties within AWS are so varied, no one can be an expert at everything. Any of the specialist “architects” that work streams get assigned to when I lead a project are probably better than I am at their specialty. My knowledge is wider than most. But not deep. Someone needs to be deep to get the job done.

If I had to down level in responsibilities to be hands on within any specific area of technology, it would take me a few months to be competitive.

[Shaun0 → WheelsAtLarge]

I appreciate your advice about certification and specialization. However, from my experience in software engineering, I've observed that certificates seem to carry less weight compared to previous employers and actual work experience. Companies tend to focus more on demonstrated skills and project history. Nevertheless, thank you for sharing your perspective!