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!
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.
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.
And in my case, always be studying.
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.
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.
I usually think about a career in sales engineering because of this.
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.
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.
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...
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.
The short version is when people can ease sideways to a completely new role at their current employer. The longer version involves getting a new job doing the same thing, but at a company that does a lot more of the thing you want to do. Initially you do the thing you were doing before, but there's more opportunity to shift sideways when you get a good rep.
So "Wrote SOPs for spectrum analysis using CV480 machines" became "Analyzed processes.and wrote detailed plans to spread domain knowledge across team".
The most important thing is to decide as specifically as possible what new role you want to take on and angle everyrhing in that direction. You can't just be open to whoever will take you - make your transition seem inevitable.
Currently trying to become a wild beekeeper dropping hives anywhere anyone will let me while coding on side projects at the same time.
I recommend beekeeping. Go on a course somewhere, learn a little, get a hive, make mistakes, learn, scale, profit.
(Just a little joke, based the meme of developers quitting their jobs to start a goat farm.)
Also, I'm allergic to bees.
Oooof, I don't... maybe you know the secret, but being an amateur beekeeper and watching what the pros do, it looks darn hard to reach scale.
He casually drops that he has 250 hives, and that he's not that into it...
[0] https://web.bluebeansoftware.com/whats-all-the-buzz-with-sma...
Too cool! Might give it a try.
I'm assuming no-touch hives are designed differently than honey-extractive hives.
https://www.beekeepingnaturally.com.au/natural-beekeeping/th...
For me my greatest motivation was that I wanted to work with people individually, money be damned. I had a supportive spouse and we already lived frugally so I could build a business without (overwhelming) fear of failure.
If you can still stomach office work become an accountant. You’ll use all your analytic skills in a role that is useful to every sized company but your pace of work will be much more constant. Your ability to write small programs and debug excel will make you valuable.
Then there's "doing accounting work for a company as part of an accounting department" which is much more likely to be 40h weeks, punch-the-clock type of work. However there can still be crunch time there as the deadlines are real deadlines not VP-pulled-out-of-a-hat deadlines (e.g. tax filing deadlines, SEC reporting deadlines).
You can go to industry and climb the ladder and make good money with less crazy workload.
I know a chief accounting officer at a public company and she earns 7 figures. She works a lot but also goes on vacations and has free time.