Ask HN: DevOps Career Advice for an Oldy

I'm a late 30's devops / SRE guy who previously worked as a sysadmin in financial services. Suddenly, the jobs in my area seem to ask for only 5 years of experience of Python, AWS, Kubernetes, Docker and CICD, my salary demands are too high and I'm being interviewed by people in their 20's who think I'm an idiot. I'm struggling with the whole process I have several paths and I was hoping you could pick what YOU would do:

A) Continue learning more Python - I'm good but I don't know the math and sorting questions I'm getting asked. Continue with AWS. Take a lower-paying job with folks 15 years younger just so I can pick up Docker, Kubernetes, etc. That's a 30-40K pay decrease in New York.

Downside: I have grey hair and I think I'm competing with cheaper people.

B) Go independent contractor. I have done this but I am very bad with marketing myself, and my network isn't wide enough to score jobs, so I'm stuck with recruiters. I like this the most but I'm also struggling.

Downside: Everything else is perfect, but my marketing skills are 0 after all these years.

C) Go management. I've already been a manager on the infra side. I shied away in future roles thinking I preferred hands-on (even though I got accolades as a people person and a well-organized improver of infrastructure).

Downside: Narrow job listings to choose from, also weak at marketing.

What would you do and why?

1) What is motivating this change? Are you currently unemployed, looking for new work or rather concerned about ensuring your employability over time? Are you looking to earn a higher salary?

2) In an ideal world, would you want to learn this new technology or would you rather stick with building your existing skills / working with tools you are familiar with? Are you willing / interested in learning these tools outside of work, or would do you have other engagements that take precedence (family, non tech hobbies, etc).

3) How much risk are you willing tolerate? Do you have a big enough safety net if the independent contractor thing doesn't work? Maybe plan out this scenario on paper, and do some rough math if possible.

4) You are well within your right to avoid management roles (or anything that doesn't serve you). What are your goals with work, pay the bills even if the work is tedious, emotionally challenging?

My apologies if these questions aren't helpful for you. I'm just yet another obnoxious 20 something in tech.

Businesses want DevOps, no one wants to pay for it (as you point out, "Take a lower-paying job with folks 15 years younger just so I can pick up Docker, Kubernetes, etc. That's a 30-40K pay decrease in New York."). The market has spoken, go where the dollars are (and the on-call rotation and fire drills aren't). Get paid for what you know, not selling each hour of writing code or infrastructure via DSL and the PagerDuty rotation.

OP: I'm happy to connect you with some NY specific recruiters for the job type I mention.

anyway, my advice: don't settle. you are a senior. find a job that is willing to accept you as a senior and acknowledge your ability to learn quickly and adapt. demand a high salary (higher than what you're making now) with confidence.

it may take you a couple months to get up to speed, but you have seen it all before. you know what to look out for. you can smell the bullshit out there and you are responsible enough to have autonomy. you don't get this with newbies. this is what a company is really paying you for.

in the meantime, start building environments using these tools you are unfamiliar with. show you have initiative and can talk about these tools for when you get interviews. it may take a month or two until you find the right job. it's hard, but be patient.

as for management, well that's up to you. I tried it once and sucked at it, so I'm fine just being an engineer :) p.s. also check out terraform