Advice for an older software developer looking for a change | Hacker News Reader

Advice for an older software developer looking for a change

17 pointsrcarndrums20 comments

My father is nearly 70. He works as a Cloud DevOps engineer for a large hospital. He seems really troubled with his current job, especially the fact that the people he work with don't value good engineering (my interpretation). He wants to move to a more tech/engineering driven company, but obviously with his age this is tough. He always talks about how he wants to move to a better job, but then says there's no point at his age. I do think he's a really competent engineer (I say this as, I think, a fairly competent software engineer myself, currently working at a major-ish tech company), and so I'd like to see him work somewhere he can thrive but worry it might be too late. Any advice on this?

Edit: Don't mean to be cynical, but as a potential plus, he does look quite young for his age (I'd say a solid 10-15 years)

View on HN

I do a lot of cloud infrastructure and system admin, at 62. I freelance so no one cares about my age, only what I can deliver. I see lots of freelance opportunities for that work because many companies don't need full-time, can't afford, or can't find people.

I second this. Freelancing roles for cloud infrastructure (and even data infrastructure) might be a good fit because there is some degree of needing quality engineering - otherwise, things just don’t work.

I agree. Contracting is great, and no one cares about your age, just what you can do. I've been paid and paid thousands of dollars without ever actually meeting someone in-person.

He should absolutely check his employment agreement, though, and make sure he doesn't:

* use company equipment

* do any work for a competitor

* work on company time

Contracting also is helpful because it is something he can dip his toe into without a large time commitment (as opposed to a job). I'd suggest he reach out to people he has worked with in the past that have left the company (LinkedIn is good, but Facebook might work well too). My go-to phrasing is:

"Hiya, hope you are doing well. <Anecdote, like 'remember when we shipped project X? Guess what, it's still running today'.>

I'm reaching out because I'm looking to do more contracting and to expand my network. In particular, I want to do <the type of work he wants to do>. I'd prefer to do it off hours, about <X hours a week>.

Do you know anyone who is looking for a hand? If you do, or think of anyone, I'd sure appreciate an intro."

This phrasing is far less direct than "Do you need help" but conveys the same message.

He should also think about a rate that he'd work for, as that will likely be one of the first questions any possible client will have.

How do you do contract work where you get paid a significant amount without even meeting the person? How does a company or a person trust you to give you some work without even meeting in person. You must be doing something super right that some of us might not know that would open doors for us.

Can you please elaborate?

I have customers who have paid me thousands of dollars every month, for years. I haven't met most of them face-to-face. It comes down to trust. Since 2014 I have worked through an agency that takes care of contracts, billing, payment, so that's one route. But even before going on with the agency I never had a problem getting paid.

You should not put yourself in a position where a customer owes you a lot of money. I define "a lot" as an amount I would consider legal action to recover. Charge for deliverables with clear expectations and definition of "done." If you get a sketchy or slow-pay customer who argues about your bills, drop them, they're not worth it.

Anecdotally I have known lots of freelancers in my career and slow pay/no pay is not a big problem for the freelancers who deliver what they promise and avoid the fringe customers. It's the customers who want you to clone eBay for $5,000 in a month who won't pay you. Reputable companies and organizations might take a while to cut a check but they won't screw you.

It's all about derisking what you are selling (your labor and expertise).

It's been a few years, but here are a couple of tips:

* Start with a warm intro from someone you've worked with in the past. This lowers the risk for both parties. This is why I suggested reaching out to former co-workers; they know you and (hopefully) will vouch for you.

* Begin with a small project first. Again, this is about lowering risk. Is there a project you can do for a couple hundred bucks? Can you write a planning document, or do an analysis of the current infrastructure with a read-only account? Or a small enhancement/bugfix?

* Document your expertise in a way that others can find you. This could be code, gists, a blog (I have multiple :) ), articles in places like dzone or the stackoverflow blog, or podcasts. This is good for finding new clients, too.

* An entirely different option is to use a contracting company, where they find the work and take a cut (a large one, typically). This way the company has trust that you can leverage. It's been decades since I walked this path, so I don't know how available it is now.

One other thing: contracting is risky for both sides, not just for the client.

For the first project or two with a new client, don't ever bill more than you can afford to lose. I've never been stiffed 100%, but one time I had to pursue a client for months to get a 4 figure paycheck. Here's that story: https://www.mooreds.com/wordpress/archives/2650

I am someone who has been interested in cloud freelancing for a very long time except freelancing and cloud don't seem to go well together for me. I've had zero callbacks when I tell them I'm a freelancer.

The companies I've worked with in the past have even the dev environments on the cloud pretty locked down and access to any higher environments are usually locked down even more. Given that cloud has a lot of important data and companies are usually very selective in how they give out access. How do you do freelance work when it comes to cloud?

Can you please elaborate? If cloud freelancing is something that looks like it could be within my reach it would make my family and I's life easier in so many ways.

PS: I'm from a relatively third world country so please factor that in.

I understand the trust issue, and honestly working from a different country presents some problems. I (US citizen) only work for US companies (though I don't always live in the US). I think that makes the customer comfortable because they have legal protections. I also work through an agency that has vetted me and makes the relationship feel more solid and professional for the customer.

Some of my customers just give me the cloud credentials -- they have no idea what any of that means, it got dropped on them when the last sys admin quit or stopped returning emails. Some know how to manage their cloud assets and create an IAM user with appropriate permissions. A few have made me work with/through their IT department.

Generally I ask for a privileged user login to their cloud control panel (AWS, GCP, Azure, Rackspace, Digital Ocean) and an ssh login with sudo permissions. I may get some or all of that, depends on what they need. My involvement ranges from reviewing existing cloud setups and offering advice to fully managing cloud infrastructure and servers.

I kind of fell into this from programming work. I would notice problems in the customer's infrastructure, or they would tell me about problems, and I told them I could help so they gave me the keys. I tend to keep my customers for a long time (years, a couple over a decade) so they trust me already.

You might look at consultancies that focus on security and see if you can work through them. Security experts usually need the same kind of access I need. Very often the first time a company needs a cloud expert/system admin is when they get hacked or something crashes, so security consultancies and IT support companies get those calls, and you can freelance for or through them.

A cloud expert/engineer certification can't hurt. I don't have any certifications but I have gone through the AWS materials. I got started with cloud admin early-on so I've kind of grown with it as it exploded. I have prior system admin experience that helps.

Lots of smaller companies have cloud infra that they paid someone to set up for them, but that person/company has moved on and doesn't maintain or support the customer anymore, so that's where you look for opportunities.

Thank you for taking the time to write that response. This is helpful.

Also, all things considered equal, would you consider this an interesting line of work?

Sometimes. I work to make money, not-so-interesting pays the bills too. I get satisfaction from solving problems and happy customers, not from technology itself.

This post made me happy, just to know that there are 70 year olds working in software at the IC level. The oldest I have seen in my companies is probably 60 max - and I found a correlation between older people working in tech, and working as a freelancer / contractor. Probably because they have built up an expertise in an area so they can, plus enjoying the flexibility when you are possibly less reliant on the money (older kids, etc.). I want to see more people this age in tech, doing the coding / ops!

As for advice - I am not sure! Just keep applying. Don't let the age be a factor for him, and then if it is a discrimination factor for employers then it is unfortunate but keep applying anyway. There are plenty of people who appreciate talent.

What does he mean by a more tech/engineering driven company? Do you have examples? Does he mean AWS or Oracle or Azure or GCP?

Does your dad (and the cloud devops team) work with folks at their cloud provider and is it one of the big ones azure, gcp, aws. If he has close relationships with them then that might be a way in. Or is it a 3rd party contractor running the hospital-cloud interface?

There is a lot of engineering to be done at the interface level even at the devops level. Right now cloud "devops" for hospitals is a big growth area and since he has experience in in that environment, I would think the bigger cloud providers would want his expertise as a solutions/support engineer.

The other thing for him (and maybe you) to do would be to start a 3rd party cloud/devops integration company!

There are also med-tech companies that deliver services through the cloud as well. Devops itself is arguably being eaten by software as things progress (as devops ate sys admin).

He's 70 and if he's been in engineering for a while I'd guess he's built up a good nest egg. And he could get Social Security if he's not already getting it. Why not quit and start his own company?

What has he done in his career? It would be easier to help with a bit of history here. What did he enjoy the most? What did he feel he was best at? Why is he still working and not in retirement?

> Why is he still working and not in retirement?

This should not be a question. It is none of your business.

How about letting the person asking the question take a stance on that instead of you being offended from the side-line? I think it might be a very important piece of information to figure out a strategy going forward.

I am not offended, not by a long shot but I would be if someone asked me similar question.

He's passionate about engineering and has a lot of energy which is why he's still working and wants to continue. I think his focus is on identity, worked for a few years before this as a support engineer for an enterprise software company which ended up moving to a different state (he liked that job a lot more). But he's had a spotty work history, taking up engineering late in life and starting his own IT company which shut down ~15 years ago.

From what you've told so far, I think he should just simply look for another job. If it says DevOps, SAFe, Agile or something like that in the title or job description, then chances are the company has unfortunately been swindled by these snake oil salesmen and it will be hard to find time for good engineering.

There can't really be a shortage for more support engineers if he likes that, but if he wants to do more core engineering then of course go for that. Most of the big enterprises should have room for him in many different departments and he might be comfortable and safe.

As for concrete advice: Just go looking for jobs and weigh pros and cons. You can do it on his behalf and bring a few to him for discussion.

Don't be pushy if he's not into the idea and just feels like complaining a bit. Sometimes all a person needs is a bit of acknowledgement and not a solution.

Just like any age, apply to as many jobs as possible

Reply on news.ycombinator.com