Ask HN: A Career Dilemma • Hacker News Board

Re: Ask HN: A Career Dilemma

#11

Post by scarface_74 » Wed, Jan 15, 2025, 3:27 PM UTC

Shaun0 wrote: post #10

scarface_74 wrote: post #9

Earlier quoted context omitted.

> 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…

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 me…

> 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.

Re: Ask HN: A Career Dilemma

#12

Post by shw1n » Wed, Jan 15, 2025, 4:38 PM UTC

Shaun0 wrote: post #6

shw1n wrote: post #4

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 "…

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 technic…

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.

Re: Ask HN: A Career Dilemma

#13

Post by Shaun0 » Thu, Jan 16, 2025, 1:38 AM UTC

shw1n wrote: post #12

Shaun0 wrote: post #6

Earlier quoted context omitted.

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 technic…

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 ser…

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?

Re: Ask HN: A Career Dilemma

#14

Post by shw1n » Thu, Jan 16, 2025, 6:10 AM UTC

Shaun0 wrote: post #13

shw1n wrote: post #12

Earlier quoted context omitted.

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 ser…

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 strateg…

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)