Ask HN: How can I realistically change careers?

179 points · throw101010101 · 4 days ago

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!


159 comments
w10-1 · 3 days 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.

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PaulRobinson · 4 days 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.

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austin-cheney · 4 days 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.

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physhster · 3 days 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...

khafra · 3 days ago
Broad advice I've seen for already-employed people looking for a change: Switch employers and roles at different times.

e.g., Learn enough to be useful, then talk to the security guys at your company. Prove you're useful and trustworthy; see if there's any tasks you can do for them without violating policy. If a spot opens up, see about changing roles within your company.

Or, join a smaller company, where your role and some security responsibilities overlap.

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