Hacker Remix

Ask HN: How can I realistically change careers?

152 points by throw101010101 19 hours ago | 145 comments

I’ve spent almost two decades in digital-focused roles, specialising in strategy, user research, and creating frameworks for better customer experiences (ostensibly UX I suppose).

While I’ve found the work rewarding, I feel it’s time for a significant career change—potentially outside of this domain entirely.

I’m seeking advice from others who have made mid-career transitions:

• How did you pinpoint new directions that matched your skills and interests?

• What were the most effective ways to reposition your experience in a new field?

• Are there any resources or strategies you’d recommend for upskilling or building networks?

I've often thought about cybersecurity as something I'd like to specialise in, but it seems like bootcamps and the like aren't worth the money they charge (most advice has been starting at the bottom as an IT helpdesk worker and going from there, but I'm no spring chicken anymore. But I'm not against starting at the very bottom and working my way up).

I realise this is quite a broad ask, and apologies for the throwaway. I’d appreciate any insights, especially from those who’ve shifted from established careers to something entirely different. Thanks in advance!

w10-1 11 hours ago

The domain (digital) might be less important than the role.

As a contributor, you have to be an expert, but you're really not on the hook.

As a decider, you can be a generalist, but you're on the hook.

The traditional mid-life transition is from contributor to decider, into management or starting your own company.

In my lifetime, the value of contributors has diminished while the value of deciders has exploded, largely due to the pace of change and the leverage of capital. Contributor skills get stale fast, but deciders making the right decision at the right time is a gold mine, waiting to be tapped by capital leveraging the latest tech/policy.

Also, I think people mature more as deciders. It grows confidence and effectiveness. Contributors grow to become defensive and stuck, i.e., dependent on being specifically useful.

It's tempting to look for nearby opportunities, but it may be more transformative to ask what kind of person you want to be in 10 years (and what will the world be like). If you operate from that perspective, you're leveraging world change and relatively immune to personal difficulty. People respect that, and you can be proud of making your way instead of just fitting in.

Becoming a principal rather than an agent is something (like meditation) that applies at all fractal scales of life, so you can re-orient while in current roles.

And don't worry too much about realistic. Focus more on delivering value, and the principle of least action will arrange things for you.

afiodorov 8 hours ago

Overall, I like the sentiment. However, there’s a common pitfall: as experts transition into decision-making roles, they often rely on their older technical knowledge. Over time, this once-valuable expertise can work against them, because it’s based on a previous generation of technology.

Many people assume that excelling at a role automatically qualifies them to lead, believing firsthand experience is enough. Yet as the gap between how things are actually done and how they think they’re done widens, their decisions can become increasingly detached and counterproductive.

scarface_74 8 hours ago

That’s true. You have to hire well, ask the right questions and have “strong opinions weakly held” or sometimes even “weak opinions weakly held”.

And in my case, always be studying.

hn_throwaway_99 5 hours ago

Wow, this is a really, really great answer. It was also a bit of a hard read for me personally, because I know it to be true, and because I kinda discovered I was a bit f'd in midlife - I had been a great (and I think recognized as great) contributor early on in my career, but I didn't want to make the transition to "decider" because I fundamentally don't enjoy managing teams of people. I've found it increasingly difficult to be good at the "contributor" role because I find it hard to stay motivated to keep change with the pace of tech. Not sure if it's really hard for me to learn new tech (though that's likely, as it's basically an inevitable consequence of aging), I just honestly don't care as much.

So for me, I'm actually getting off the career train to become a craftsman, and I plan to go to school to become a luthier (violin maker). May not be as cool as that guy who switched from a Microsoft principal engineer to duck farmer, but it's probably similar. I was lucky enough to have earned and saved enough early in my career to make this change.

But as you say, "In my lifetime, the value of contributors has diminished while the value of deciders has exploded", and that is totally true. I've accepted I'll never make as much money as I used to (obviously not even close being a luthier). But I think I'll be much happier.

jimmydddd 9 hours ago

Great answer. Along with the "what kind of person ... in ten years" question, you might be able to search around for folks who look like they're doing something you might want to do, and move in that direction. I had a colleague do the opposite. He looked at the day-to-day existence of the folks at the top of our organization (where he could possibly be in 8-10 years) and realized he didn't want to do that. So he shifted career paths.

zemvpferreira 10 hours ago

While I’m sure it doesn’t apply to all cases, I really enjoyed your way of framing the transition. Well put.

PaulRobinson 17 hours ago

The most interesting jobs I've seen are where people bring two specializations together, into a single role.

Take the strategy, user research and frameworks you do to drive better CX, and apply that to something you have a deep interest in away from the usual mainstream. It could be a hobby, it could be the cyber stuff you're interested in.

On that, you're more likely to enjoy getting into cybersecurity by joining a company doing that today as a CX expert and getting more technical over time and looking for a horizontal move, than you are from starting from scratch and working on an IT help desk and trying to work your way up.

I'd also suggest starting a blog or producing open source content in the field you want to move into. I'm starting to do this, because it can highlight my knowledge/skills while my CV is in a completely different field, in order to gently build traction and attention in my "target" industry.

One last thought: don't underestimate that you're stressed, burned out and just need a decent period of slow work to recover. I think most people looking for major changes in their career are just tired and fed up. I know I am. They say a change is as good as a rest, but a rest is as good as a rest as well.

Gooblebrai 16 hours ago

> The most interesting jobs I've seen are where people bring two specializations together, into a single role

I usually think about a career in sales engineering because of this.

physhster 12 hours ago

I'm not quite where you are yet, but I can feel this approaching... I started my career in IT tech support, became a systems & networks engineer, dabbled in IT management, data center construction management, software technical program management, ending up managing compute resources for a large-ish product with 1B+ MAU. But I think I might be done with tech.

I can't shake off the feeling of impending doom for roles like mine in the current market and the constant push for AI solutions.

So I am seriously thinking of moving and opening a coffee shop or wine bar, or even a coffee truck to be honest. Meeting people, making their day a little better, rather than staring at the computer all day every day.

I would encourage you to read up on Ikigai[0] to figure out what makes you tick and can give you the income you need. Not all passion projects pay the bills but some do.

[0] https://stevelegler.com/2019/02/16/ikigai-a-four-circle-mode...

austin-cheney 17 hours ago

I was a 15 year JavaScript developer. Now I run operations for an enterprise API system at a large organization.

My career stagnated as a JavaScript developer. Most of my peers were afraid to write original software which made it really challenging to do anything until I was finally laid off from worst of it. Everything had to be little more than copy/paste from some enormous framework into an enormous mono…monster of stupidity. If you ever proposed sanity people would get irate because it threatens to expose that nobody has idea what they are doing.

Simultaneously, though, I have a part time job in the military. In the military I learned networking (routers and switches), operations, security, management, and more. I still maintain my security certs and have a clearance.

Last year a recruiter reached out to me about a work from home job writing enterprise APIs. I passed the interview using my knowledge of data structures and the inner mechanics of WebSockets from years of writing personal software. For most of my career as a JavaScript developer it seemed the only way I could program at all was to do it on my own outside of work.

Since then they promoted to lead operations and at the same time to be a team lead in a different organization.

scarface_74 16 hours ago

You’re still doing software development. That’s not a major transition.

austin-cheney 14 hours ago

Not really. Operations is, at best, 5% software and more like 90+% project management. It is handy being able to write original applications on the fly to automate some of the insanity because there are multiple things happening simultaneously and many things to account for.

hn_throwaway_99 11 hours ago

But in reality that's just a natural career progression for like 90% of people as they move up the ladder.

There are actually very few people above around age 45 or so that write code for a majority of their day (percentage-wise), and that includes people who still consider themselves in "individual contributor" roles. E.g. even a principal engineer is going to be spending a majority of their time reviewing code, doing systems and architecture work, mentoring more junior developers, organizing more junior developers, etc. When I was a principal engineer a huge part of my job was "project management" as you put it.

austin-cheney 9 hours ago

> "project management" as you put it

That is like saying “doctor” as you put it. It’s super cliche for people in software to title themselves as principal or expert or famed ninja grand wizard and yet simultaneously not know how the real world works. Project management is actually a real thing, seriously. It’s not just some imaginary invocation like lawyer or teacher. People actually do that for a job and get paid real money. Unlike software where developers pretend to be qualified against their own imagined baseline there is actually a license/cert from a universally recognized governance body.

This kind of nonsense is why so many developers that don’t have imposter syndrome want out.

If you want to see what real project managers do then peer into construction where they manage billions of dollars in assets with critical timelines that have multimillion liabilities.

hn_throwaway_99 5 hours ago

I think you took offense because you interpreted my "project management" statement to be in scare quotes, where that was certainly not my intention - I literally just put them in quotes to highlight that I was quoting from your previous comment.

I certainly didn't mean to denigrate the job of project management. But I do agree with the other response - project management is just about ensuring a job is done on time/budget by tracking and managing a complex set of dependencies. I will say, at least in my experience, that really great official software project managers (I mean that was their job title) are worth their weight in gold, but they happen to be quite rare (again, emphasis on "in my experience"). Too often I worked with project managers whose thought their role was scheduling meetings and constantly asking all the engineers if the Jira board was up to date. But I think this because, when done correctly, the project management role is a challenging one that takes an unusual combination of attention to detail, communication skills, and ability to stay motivated on what can feel like boring tasks in the moment.

scarface_74 5 hours ago

There are also “certifications” for AWS. I have six of them. They prove nothing as far as competence in an of themselves.

In the grand scheme of things, project management is about making sure projects are done on time, on budget and meets requirements.

It’s about managing dependencies, from a software development methodology, it’s creating a directed acyclic graph but with people instead of computers.

It’s also dealing with managing stakeholders, contributors, blockers, budgets, scheduling meetings, keeping the higher up informed, etc.

If you put a gun to my head, I can be a competent project manager. As a “staff” software architect half of my job managing cloud projects as a tech lead with the other half being more of a solution architect when we first sign a customer and designing an implementation plan with work streams and epics.

Usually I end up splitting the project management part up with a real project manager.

It’s not because of a lack of competence. It’s bandwidth.

But just like you can’t be a good tech lead if you don’t have some level of competence technically, you have to be decent at project management.

scarface_74 14 hours ago

What an I missing? You said you were writing “enterprise APIs”.

ecshafer 13 hours ago

OP said he "Runs operations for an enterprise API". My guess is that they are running a team that manages an infrastructure platform which developers in their org target. My guess is that this involves a team which manages deployments to multiple clouds / regions / data centers, some load balancing configuration, etc. using some software like Akana or some IBM product.

stonemetal12 13 hours ago

He could be clearer about what he does. He did say "Last year a recruiter reached out to me about a work from home job writing enterprise APIs." He doesn't mention going from writing APIs to operations management. Which seems to be where the confusion is coming from.

Though that is my understanding of how you make a big career change. Do your current job in a company that does what you want to do. Then change roles rather than jump to the role you want straight. Kind of beat the chicken and egg problem, of needing experience to get a job and can't get experience without a job. A job that is adjacent to the one you want is "second hand" experience.

brutus1213 17 hours ago

Curious about the military job (and other services including Police Departments). Are you eligible for pension/benefits as a presumably civilian subject matter expert? How does one get such a cyber gig?

austin-cheney 14 hours ago

Its Army Reserves. Yes, I am already locked in for a pension. I am not a civilian. I am completely interchangeable with full time military, evidenced by my 5 military deployments.

How does a person get such a job? They join the military.

When I joined cyber wasn't a thing, because I am old. I joined the first cyber organization shortly after it formed and was a member for about a decade. I was promoted out of that organization and shortly thereafter a formal cyber organization was created, not just a few units. By that point I had become an officer doing more generic systems integration and physical communication infrastructure things.

The biggest difference between the military side versus the corporate developer side is that military tends to run towards problems. The goal is have everything working so that you reach steady state and don't have to do high visibility work. High visibility is bad, because it suggests you are failing something important. Corporate developers, on the other hand, tend to be either trend chasers that want high visibility yet low effort work until things fall apart and then they run away or are long term employees that want boring steady constant employment.

Dachande663 16 hours ago

Sounds like a reserves position, probably in S6/Signal Corps given the description of dealing with IT.

austin-cheney 14 hours ago

That's it. I have been an acting/deputy brigade S6 on and off for years. Its more people and expectation management at that point than anything directly technical, but you are still expected to be an expert, like being a corporate associate director. I just promoted out of that and am looking for the next thing.