10 years experience as a generalist. It's becoming a problem. I feel stuck.

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Candid_Exam276@reddit

Hey thanks for sharing your journey! It sounds like you've gained a wealth of diverse experience over the years, which is a valuable asset, even if it feels like a challenge right now. Many professionals go through phases of feeling stuck, especially when trying to find a specialization in a competitive field.

If you're open to it, I’d love to invite you to a free coaching clarity call. We can explore your experiences further and discuss strategies to leverage your broad skill set into a more fulfilling path. Sometimes, a fresh perspective can help uncover the opportunities you might not have considered yet.

Feel free to reach out if you're interested—your next step could be just a conversation away!
You can also check out my website here www.chenmadar.com

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HorseWithNoUsername1@reddit

Find an IT specialization and an industry where said speciality cannot be offshored.

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Moontoya@reddit

Everyone wants experts whilst offering intern compensation.

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proud_traveler@reddit

You'd probs do well at a small/medium sized business, if that floats your boat. They tend to want one guy who can do everything from setting up cctv to pulling cables in

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SouthJerseyPride@reddit

SMB is where I thrive. 16 years of experience between SMB and Corporate. I'll never go back to corporate world, its just not for me.

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daweinah@reddit

Where does a 2500 person company fall on the SMB to Corporate scale?

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jimmyjohn2018@reddit

SMB implies fewer than 500 employees.

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daweinah@reddit

Thanks. I always wondered what the cutoff was.

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brusiddit@reddit

It's different in different countries. I think enterprise = 1000+ where I am from.

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jimmyjohn2018@reddit

There are a few different technical metric in the US based on income or size, but this one was always easy to remember.

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SouthJerseyPride@reddit

That's on the medium to large size to me

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Jaereth@reddit

We were a SMB that got bought by a corporate....

Shit's been weird...

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MisterUnbekannt@reddit

That is my current situation, changes will be starting dec/jan. Anything specific to look forward to?

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Jaereth@reddit

Is corporate ISO/CMMC/Etc certified and your company is not? Get ready to do it.

Also - no matter how "hands off" they are with the child companies - you are going to have to likely prove compliance with their IT policies. Probably "whatever is more strict" will be the rule. I've never seen anything we had on the books as a policy when we were purchased that was MORE strict than what the parent company was doing.

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brother_yam@reddit

Paperwork

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byrontheconqueror@reddit

and meetings to discuss meetings and paperwork

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After_Nerve_8401@reddit

SMBs are where generalists thrive. The trade-off is that specialists tend to make more. Decide if you want to be happier or make more money. If it's the latter, pick an area to focus on, i.e., networking, storage, security, etc.

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EastDallasMatt@reddit

Yeah, I ran into the pay ceiling problem and chose the management route, which was much more accessible to me (without a degree) in an SMB.

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223454@reddit

Maybe I've worked at the wrong places, but in my experience generalists aren't treated well or paid well. A lot of people see us as glorified HD. I've definitely hit a pay ceiling too. I'll be job hunting again this winter. I might just try management.

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jimmyjohn2018@reddit

Here's the secret. Become the manager.

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Jaereth@reddit

So say you are an ace generalist - can design and maintain networks for SMB, Can set up servers for SMB with all services - Great with O365 - Can set up a bit of Azure. Should check all the boxes done it all

But never managed people or been manager of anything and would worry about the lack of skills there.

How do you make the jump?

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somesketchykid@reddit

You don't need to be a manager to be a leader, you can start being a leader today. If you have really good soft skills or client management skills they go a long way and there is a lot that is directly applicable.

You should also consider whether or not you'd actively enjoy doing things like hiring, performance managing, being responsible for other people's quality of work, maybe budgets depending on size of org, vendor management, training

What kind of strategies will you have for example when you try to give somebody some work and they say "I'm not sure how to do that."

There are so many things I'd have never dreamed about doing as an employee so I never considered the fact that I might have to deal with these issues as a manager until after the fact.

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jimmyjohn2018@reddit

Great answer.

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Valdaraak@reddit

I fell into the management route and am currently working to get right back out of it. I do not jive well with management skill sets.

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gtipwnz@reddit

How come?

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null-character@reddit

Because being a manager sucks. You have to deal with putting out fires all day, dealing with employees personal issues and employees thinking you don't do dick all day.

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gtipwnz@reddit

Aw

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pascalbrax@reddit

a good manager can say "yes" to the right people while they think "fuck no"

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kaarri@reddit

Yep, seems so. I have been capped at around 3000 euros while specialists (Azure etc.) / MSP can almost double that.

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secret_configuration@reddit

Decide if you want to be happier or make more money.

Some here might be surprised but it can be both. SMBs can pay very well, you just have to be in the right industry.

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jmeador42@reddit

Local government would be great too. They don't have the budgets for an entire team of people. Low stress, high job security and satisfaction.

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nomadz93@reddit

LOL...low stress and high job satisfaction is a joke. Hard to have either of those when you are juggling 10 different balls and can only spend time getting things off the ground kinda working then on to the next thing.

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jmeador42@reddit

That’s only if you’re a one man show, and even then, you really should be doing less and taking the time to do things right.

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nomadz93@reddit

Maybe in sleepy towns. Not in any decent size county.

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Jbugx@reddit

I was basically a one man show for a county here in Texas. I got the chance to teach myself networking there because it was needed. I got to the point where I was either just watching YouTube all day or I would get up and walk around talking to people to see how things were going. It was boring but very very low stress.

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Kraeftluder@reddit

And primary/secondary schools. They don't have money and need someone who understands things about as many things as possible. There are plenty of schools (or districts in the US) with enrollment numbers ranging in the few thousands. Anything up to 5K I've seen my US colleagues handle with just 2 people, excluding feet on the ground that swap out broken keyboards and reset a password every now and then.

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whythehellnote@reddit

I doubt SMBs are paying €100k for an IT guy, more likely "my nephew says he can handle it for €50 on the occasional weekend"

Or do I have the wrong impression?

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Remarkable-Cut-981@reddit

Why you hate and is jealous ?

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Ikinoki@reddit

This is rare now, because all nephew millennials grew up. Now gen z is coming and they are as adamant as boomers.

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IDontWantToArgueOK@reddit

Yes sir. Sole contributer at a small business is awesome as a generalist.

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secret_configuration@reddit

16 year SMB generalist checking in. At this point, I can't imagine going to work at a large corp.

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londumpster@reddit

I would advise to Go full time. Possibly a consultancy for a few years. Get some good experience on technologies that interest you and client facing roles. And then you can move back to contracting if you prefer. I have done this. Was a sysadmin 15 years back, joined consulting and left after 5 years as senior consultant . Now a Solutions Architect for Azure and M365 for last 8 years contracting.

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Ok_Mention6990@reddit

Being a specialist is incredibly boring. Doing the same exact thing day in and day out. I mean ugh. In my job I literally do everything from creating networks for phones servers switch’s desktops and cameras. Setting up servers, both physical and virtual. Currently about to go hybrid with azure. I get to plan out and implement anything and everything I see fit. I also deal with EV installs and setup. Solar energy systems, websites. Honestly it just goes on and on. So tell me. Why in the world would you just want to do a single thing for the rest of your life.

To me it sounds like you are not a contractor. But really an employee with no say so in anything day to day.

Why don’t you actually branch out to be an actual contractor and open your own company doing IT work for SMBs. Not the plural. As a contractor you cannot be told what to do or what time to do it. That’s the point of a contractor. So if you are doing set hours you are just an employee with benefits or further prospects. Hope you take this all to heart.

What you need is to be your own person and not someone else’s.

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xxtoni@reddit (OP)

I agree with what you're saying and I'm trying to do something in that direction but do you have some examples of which companies do work like that? I am looking for a business model that would work for me right now.

Can you elaborate on what you mean exactly with being an actual contractor and doing IT work for SMBs. Like what does that mean in exact terms?

Thanks for the tips.

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robotbeatrally@reddit

Pretty much the same except I make half that lol So I have imposter syndrome and I'm poor xD

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null-character@reddit

If you manage stress OK you can probably make more money at an MSP (they love generalists). The trick about MSPs is finding the right one that isn't understaffed and/or run by morons.

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xxtoni@reddit (OP)

I don't want to own a MSP let alone be employed by one.

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null-character@reddit

There are good ones out there but it certainly isn't for everyone

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asedlfkh20h38fhl2k3f@reddit

OP I think people like you are gold. All it's going to take is applying for positions until you find someone who realizes your value. There are countless companies who desperately need an internal IT manager who basically works full time, and who knows how to reach out to vendors, ensure their environments are properly managed and maintained, who can facilitate projects with vendors, implement changes to keep the org up to snuff by way of security, and the fact that you have hands on experience puts you in a good position for that type of work. Mega MSP's are attempting to fill that role for as many business as they can, equipping a large army of idiots who will continuously cycle through, and the end result is an awful IT experience.

Any company that can afford a full time internal IT manager should absolutely get one. IT is far too messy to just put all your eggs in the basket of some 3rd party mega-suck-msp. Even if you have a good year with that big MSP this year, wait another year and see. Odds are that IT guy you like has moved on because that big MSP doesn't pay their army of idiots enough to keep them around long enough to become smart. The good ones never stick around, why would they? They'll probably move into an in house IT manager role someday.

Moving forward, as big MSP's continue buying up smaller IT companies and then scratching their heads when they get complaints, there's going to be an increasing void and need for on premises IT managers who have a decade more of experience.

I've lived it and seen it first hand - having an in house IT manager positions companies into a much better place - much faster. But the kicker here is most companies don't know what they're missing. Gotta find one who values that type of role and who can also afford it.

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Burnerd2023@reddit

SMB my guy, I’m literally in the same boat. A generalist. I can’t setup most anything and have skillsets that merge into other professions. I make what you do but I’m not remote but free to come and go for whatever I need to do, granted I’m here around opening and clock out at closing.

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Pilsner33@reddit

I get the contract purgatory. I have also been in it 5+ years.

There is good and bad to it. This one I am on now I like but it isn't budgeted beyond Feb 2025. The last one was 3 years and likely could have been longer but the 3rd boss absolutely did not click with me. It is exhausting.

I am going to try for a security cert. I think it can help. Certs may be a route for you?

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Helpdesk512@reddit

I call myself the “Senior Generalist”. I am in a medium size mom and pop biz with about 10 locations and a corporate office. 6 digit salary for everything from printers to music to project management to dataflows.

I’m handcuffed to my company and it took about 5 years to become “indispensable” but may be a path for you. In your scenario I’d avoid MSPs

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ErikTheEngineer@reddit

Looking at the jobs/contracts on the market everyone of course wants specalists in something

I think that's because you're looking at contractor roles. Very few places revolving-door their general IT workers on contracts, but lots of places parachute in a contractor with laser focus on one or two items, then throw them away when they're done with them. You're paid to do a job and leave.

If you have actual skill in multiple areas, generalists are a great find these days. Most people during the tech bubble went to DevOps bootcamp and are tunnel-vision focused on the cloud and a narrow set of cloud tools. Being a generalist gives you enough background to talk intelligently with specialists to help solve problems. I've made a whole career out of not being a single-minded person focused on one thing, but jumping around and picking up knowledge in a lot of areas.

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i_cant_find_a_name99@reddit

From some of your follow-up posts it seems the issue is more finding new contracts is difficult as a generalist rather than you wanting to specialise as you think it would be more interesting? If so I think the obvious route in (joining a large company or IT services provider as an employee and trying to specialise once there) is going to mean a big pay cut (and maybe less flexibility in your 100% remote situation). Personally I'd stay doing what I was doing unless I totally ran out of work...

The only more generalist roles I see for contracting are either very short-term where they are just trying to get bodies in to help with a big deployment etc. or for roles needing security clearances (but most of those would likely need you to be a citizen of the country and not just obtain clearance, although even obtaining clearance in the first place usually requires citizenship) so that sounds a non-starter for your situation

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CantWeAllGetAlongNF@reddit

Try getting some certs

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welcome2devnull@reddit

SMB (up to \~ 500 employees) need more generalists as their IT departments are not that huge to have for everything individual specialists.

Even at medium and larget businesses there is always a need for some generalists - they have their specialist departments, everything structured with communication channels, ticketing systems, hierarchies, processes, ... and then they have special projects where you need people who can think above departments, with good (not specialized) skills in many areas to see how everything works together and to understand how systems are linked / dependent on others. Specialists in larger companies tend to think only in their own silo and don't care about others "not my business / responsibility / problem".
Your role there would be something like "Technical Project Manager with Hands-on capabilities" - working with the lead project manager, "power of attorney" for all IT related parts above the specialized departments - they are resources for you in such projects.

I'm more than 20y in IT and was always a generalist, working from small to very large companies and i just know one thing for sure, i would never want to be a specialist.

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mschuster91@reddit

Bruh, you make 100k€ in Europe?! You damn made it, congratulations. Milk that gig and retire in a few years.

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Active-Season5521@reddit

Hold on, this is a lot in europe? Can double this in USA or even Australia as a contractor.

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EvenClock9@reddit

We get called europoor for a reason. The median wage here in France is \~$2080 per month.

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xxtoni@reddit (OP)

BUT I would like to say to me it seems that in certain ways it is more hardcode being employed at will in the US than being a contractor in Europe, so its not really a 1 to 1 comparison. As a contractor the 2 worst things that can happen to you is that you lose the contract or that you get sued. You can form a company to limit your exposure and of course get liability insurance.

With the high cost of living and healthcare in the US to me it seems there is a lot more pressure to earn a lot of money.

Even at an early age I noticed that being an employee isnt a great way to build capital. When you think about it it doesn't even make sense. Nobody is going to employ you at cost, you always have to create more value for your employer than you cost him and he has a vested interest in keeping the money for himself/the business. Also as a business you pay lower taxes almost everywhere I can think of, a lot of places significantly less.

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Active-Season5521@reddit

I'm in Australia, we don't have the same issues as Americans. Was just making a couple of suggestions, but yeah, honestly didn't know wages were that poor in Europe

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mschuster91@reddit

Well, 'muricans have to pay for healthcare and retirement which is handled by governments here, and cost of living is way lower - even Berlin, you can get 60 m²/650 sqft for about 1500€, from a quick search on zillow that's about 2500-3000$ in SF. And groceries are way cheaper here too, and of way higher quality.

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Active-Season5521@reddit

Does put it in perspective a little, but I feel like OP is with more than they think.

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xxtoni@reddit (OP)

What do you mean?

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Active-Season5521@reddit

I responded to your other comment but I really do think you have more specialist knowledge than most specialists. I'm only sys admin adjacent in cybersecurity, but I market myself as a specialist in detection engineering with only 2 years of detection engineering experience. And it works. I feel you could do the same in your chosen interests

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DeputyDumbDumb@reddit

Jesus 1500 for 650sqft? I pay $1550 for 1100 sq ft (no garage all house) and am currently in a more generalist EUS role and make 87k and am way under market range for my duties and industry. This is in Idaho, I don't think comparing SF area matches the 200k. If you're a contractor doing 200k you'd be remote in a lower cost of living area like me but making 200k. If you're a contractor in SF, you should move away from SF and then grab contracts and let yourself pocket way more money.

But yes, our deductions suck here especially as a single person with 0 dependents.

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xxtoni@reddit (OP)

I am on a directors salary so healthcare is public in my case but I'm gonna have to take care of my retirment myself, it's not 100k NET. Theres a few costs as well like accounting, insurance, traveling to clients, but not to complain, I know I am lucky.

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xxtoni@reddit (OP)

I know a few people that earn over 1000€/day as a contractor but its niche stuff and they are either very good at what they do or have the right connections. I am on the lower end for contracting.

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Active-Season5521@reddit

Have you applied to some of these roles, tailoring your resume to suit? I honestly think you could get some of these specialist roles with your experience

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xxtoni@reddit (OP)

A few, never got one. They really wanted someone with deep knowledge of certain products which I didn't have.

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FunkyFreshJayPi@reddit

Lol you can't just generalize Europe like that. There's a huge difference between 100k€ in Luxembourg or 100k€ in Greece.

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xxtoni@reddit (OP)

Thats of course true but in any B2B company I can think of, you probably need 100k€/employee in revenue per year. In countries like Germany, Switzerland etc it probably has to be much more even for the company to be viable.

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xxtoni@reddit (OP)

As an employee I would probably be making half that. There's a lot of money to be made in Europe, even in Eastern Europe but never as an employee.

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cmcauley770@reddit

Whatever is above first world problems, this is that’s

Honestly, what is bad about being a generalist? Let’s look at the alternative. You become a terraform expert. 10 years pass. Terraform is replaced with the next shiny thing.

Being a generalist means stability, safety. You’re in one of the highest paying fields in one of the highest quality of living countries in the world, and could slot into any company that needs your services.

That’s the dream my friend

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xxtoni@reddit (OP)

You're preaching to the choir here but most of the positions I am seeing want some kind of specialization.

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BeardyDrummer@reddit

I am the same as yourself, total generalist.

Every interview where specialisations are required on the posting I have gotten the job with statements along the line of "Not too hot on networking, but I understand the general principal and would be keen to learn more".

From my own experience as a manager, I'd rather have someone who I thought was competent and maybe rough around the edges in skills, but crucially, who seems keen and would be a good fit for the team. I imagine most other managers think along the same lines.

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Ikinoki@reddit

Honestly, write down your CV. And by that I mean everything you know.

Here's an example:

Like I had experience modifying C code. I've never written a C app myself. But I did Kernel tinkering, adding new parts. Refactored C, C++ software. So I can write down C/C++ development because if need-be I know where to start and the software limits. I also did patching and manual rework of patches, fixed breaking changes by upstreams etc. So I can add maintenance and debugging.

I also had 5 successful AD setups, AD migrations, AD recoveries, numerous Windows setups etc so I can add Windows Server and AD maintenance, installation, administration etc etc.

I did ground up SMTP/IMAP/POP3 programming so I can write a very detailed CV regarding that but this is no longer interesting for many companies due to offers from cloud providers. But I'd still add all those skills as there's like 10 DSLs to maintain and high-pressure, high-risk environment.

When you start picking up all the shit you went through and worked through even if it happened once or twice you'll have a huge list of achievements.

After that look at offer and ask chatgpt to refactor it accordingly so you don't get discarded as overqualified (or what business means - will eventually ask too much while vendor-locking in their deployment). Good tip - add that you write perfect documentation or maintained documentation for your projects - nobody likes vendor-locking.

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FuckingNoise@reddit

As a generalist you should know enough to interview on those specializations. Just adjust your resume to appear more specialized for those roles. I agree with everyone else that being a generalist is almost always a positive.

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countvonruckus@reddit

In my experience you're right for half or so of IT specialists. Specifically specialists that focus on a particular way to solve business or technical problems, such as specific programming languages or tool specialists. As you pointed out, these folks can have their skills become obsolete just because Cobol fell out of common usage or whatever.

There's another side of specialists that are specialized in solving specific problems with an evolving set of skills and tools as the field develops. These are folks like cybersecurity specialists, network architects, AI specialists, coding that accounts for specific needs (such as extremely high uptime/reliability software development or secure coding practices), auditors of particular types of IT systems (such as NERC CIP reportable systems), and specialists in IT for very specific industries like local government. These needs are basically always going to be there, so being someone who has learned the ins-and-outs of solving those problems is a viable career and business model. This also focuses in what you need to continue to develop; an enterprise IT architect is going to be much less knowledgeable on IT forensics but if that's all the IT forensic specialist is doing then it's fairly easy to stay up to speed.

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peepopowitz67@reddit

These are folks like cybersecurity specialists, network architects, AI specialists, coding that accounts for specific needs (such as extremely high uptime/reliability software development or secure coding practices), auditors of particular types of IT systems (such as NERC CIP reportable systems), and specialists in IT for very specific industries like local government.

♫♪One of these things is not like the others♫♪♪

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countvonruckus@reddit

Interesting! I think we have different views on how AI will be part of IT in the future. I can see your perspective on the new and potentially trendy risk for a career. I think AI's gonna be part of IT for a long time; you can't put the djinni back in the bottle. That's just my reading of the tea leaves and you're right that it doesn't really belong in that list, showing my personal experiences.

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uptimefordays@reddit

This is why building foundational skills is so critical, implementations come and go but underlying concepts change much slower.

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EastDallasMatt@reddit

I think your problem might be less about being a generalist and more about being a contractor. I still consider myself a generalist, but the way I learned specialties was either by my employer paying for specialized training or me doing it by myself on the job. No one wants to invest time and training into a contractor. In addition, being a contractor inhibits your ability to go the management route.

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xxtoni@reddit (OP)

That makes perfect sense but theres a few complications for me. I have to target clients in other countries because the local market is beyond terrible both in size and compensation. The advantage of being a contractor in this case is that its a B2B relationship so borders dont really matter also it is much more acceptable to be mostly remote (other than ocassional on-site meetings) as a contractor since you arent an employee anyway so why would you sit in their offices.

Ideally I'd love to turn this into a "real" business, expand and hire people but I am having a hard time finding the right business model. It seems much simpler having a B2B relationship as a developer for example since you are delivering something (finished code) than in infrastructure where you are providing a service. I really dont want to become a classic MSP.

One German redditor suggested something like service as a product and I'm looking into that. Since you are a director do you encounter any businsses that provide infrastructure/sysadmin services that isnt an MSP?

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Ninjamuh@reddit

German all-round contractor here. You’d probably be better off staying solo to be honest. A business model that would work for you is renting out your employees to head hunters. You’d build a relationship with various head hunter companies and offer them your employees for various contracts. The headhunters get a monthly cut, you get the rest and your employees get their wages.

I personally didn’t want to deal with employees because they’re hard to get rid of due to labor laws and finding someone reliable was a huge pain.

You can just send your CV to headhunters or post it to various portals. Set up a small home lab and start going through YouTube lessons on what you want to learn.

Say networking, for example. Start setting up simple switches with a domain controller, DHCP, dns, Fileserver. Learn how they interact, learn about CIDR and subnets. Then move on to managed Switches so you can learn about vlans. Learning by doing on your own time in the evenings is going to be the best way.

Set up a Hypervisor like hyper-v, then try Esxi, then Proxmox etc.

All you really need is a single homelab PC with a decent cpu and enough ram to host 3-4 VMs.

If it’s any encouragement to you… I’ve met a lot of „specialists“ who have no clue what they’re doing. They’re theoretical specialists, but not so much when it comes to practical application.

A medium sized business would be perfect for you to branch out to all the different hardware and software solutions. Better yet if it’s a team so you don’t feel like you’re getting dropped into the deep end of the pool.

Government contracts are nice as well since they’re slow paced and usually have every single aspect delegated to a particular team. You’d never be alone in what you do and can learn from others.

Don’t get discouraged by all the requirements. Most are only looking for someone with experience , but not necessarily someone to build an entire Datacenter from scratch for 100k employees.

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xxtoni@reddit (OP)

Oh hey I recognise your username from EDV_de.

Honestly I've been thinking about the body shop as well. That was my first idea honestly cause what one agency did to me was daylight robery so they weren't even a body shop, they just did a Vermittlung and added 70% to my hourly rate. Good times.

That's something I'd like to avoid cause it feels kinda scammy but it's probably the simplest approach (though not necessarily easy).

I already have a small lab with a R730 just need to build it out further. I have done most of the things you have mentioned I just need to expand it deeper and wider.

Yea I've had many such experiences honestly. A vendor sends me an expert only for me to realize he is following a Docu and can't answer any of my (in my opinion) basic questions how these things interact with another. Then I found out he has never done this independently on his own. I mean it's not an issue in itself but if you are charging me 200€/h for an expert I'd expect him to know something about this stuff.

One of the main reasons I was thinking of starting a consultancy or it business or body shop whatever you wanna call it is cause ein bekannter of mine from Southeastern Europe worked for a body shop and he mentioned a few times to me that I should do it cause if his idiot boss could do it, I could probably manage it as well. He told me quite a story about how the body shops force the employees to become seniors almost by force. They "turn" them into seniors in like 2 years but this isn't just some story about foreigners ruining the German IT market, almost every vendor does this as well. Heck recently my German client was complaining about some entrance system they are deploying and said they gave him some almost Azubi as a contact for them and he is obviously struggling.

BTW thanks for the tips.

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czenst@reddit

Everyone does that because every customer wants a "senior" then it turns out it is some shitty job copy pasting XML from one file to some database and also you are not allowed to automate anything because of made up reasons.

For "scammy" part on adding 70% on top of your salary - do you happen to have access and relationships with customers that allow you to have that 70% for yourself? Because magic sauce is being named "preferred provider" so having enough credibility so someone gives you a project or having access to people who have payment authority.

Once you are in you can command such rates - being technically competent is unfortunately not the door opener but required to keep good relation and competent doesn't mean "best of the best".

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xxtoni@reddit (OP)

Nah that was scammy, everyone I spoke with agreed including contractors and other agencies. Normally agencies take 10-20%. They were just greedy. This is not normal industry practice.

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EastDallasMatt@reddit

I think you found your answer. Make it a business instead of a job.

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crystallize1@reddit

On imageboards they say generalist sysadmin is a trap job that does not provide you any basis to jump to other fields

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pg3crypto@reddit

I would disagree with that. Sysadmins overlap everywhere and can usually see the full picture in 4K whereas specialists only see their own bubble and have very little overlap with other areas.

I'm a generalist and wouldnt change a damned thing...there is nothing more depressing and unfulfilling in the tech industry than being a specialist.

If you want to get stuff done and take responsibility you have to be a generalist. Anything else and you're waiting on other specialists and trading blame back and forth...which is bollocks.

A lemon juicer is a very specialist thing, gets every drop of juice out of a lemon...amazing...but you can only juice lemons with it. A hammer can juice a lemon, you might not get every drop, but you'll get plenty of juice...and the hammer can also help you build a shed, put up a shelf, hang a painting, tenderise a steak, knock down a wall, nail down carpet...the sky is the limit...hammers are epic.

A hammer might not be the best tool for every job, but it can be used for more than one job...which makes a hammer extremely good value for money...and if the hammer turns out to be a bit naff you can always rent a specialist tool for a short period of time to pick up the slack.

If you're running a business that juices lemons, then having a world class lemon juicer is amazing...but if you're smart enough to realise that lemon juicing can't last forever, you need to ensure that you can pivot...you might have to start juicing pomegranates...the guy with the hammer can do both, but the guy with the lemon juicer becomes worthless when the lemon business dries up...moreover, if you decide to try and set up your pomegranate operation around your lemon specialist, he'll do a worse job than the guy with the hammer because he just can't handle pomegranates...it's too different, he needs you to spend money on retraining him, he needs time to get used to pomegranates...he wants to become a specialist again...to a generalist, its just another fucking fruit.

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xxtoni@reddit (OP)

They say that, do they? How very witty of them!

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crystallize1@reddit

I mean i kinda feel it myself. Setting up and fixing client machines and changing rollers and heaters in printers does not seem like a vast skill set.

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xxtoni@reddit (OP)

I escaped that particular level of Inferno long ago thankfully.

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Spiritual_Brick5346@reddit

smb, schools, doctors offices, law offices and startups love you

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hairykiwi1971@reddit

Generalists can make excellent solutions architects. Have you thought about that route?

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pg3crypto@reddit

I'm in a similar boat. I just remind myself of the grind it took to get here and occupy myself with personal projects to scratch various itches.

I've never really considered the professional work I di to be a job though to be fair. Its just a way to do what I enjoy and fund my own projects.

I've never really been bothered about career progression per se because to begin with I didn't consider tech to be a career, it was a way for me to avoid getting a proper job...I get my gratification from learning new things and building out my own ideas. If I'm really lucky those ideas turn out to be worth something and they make me some money, but usually they don't...and thats fine because all ideas are interesting but very few of them are commercially viable...if not for the boring ass work I do, I'd never get to explore the weirder and whackier ideas I have...I'd always be chasing the commercially viable ones.

Rank, titles, progression...these mean very little to me...if anything...I just want to make cool shit and try things out.

I'm currently experimenting with machine learning and I've built a prototype nutritional deficiency tool.

https://nutro.pg3.co.uk

I'm refactoring it as we speak and refining it. There is nobody that would pay me to build this let alone learn how to implement the machine learning behind it, there is no career path that I could have followed to enable me to do this professionally and I've no idea if it is commercially viable...but because I thought it was interesting, it exists.

I haven't made a penny from it, but it has helped people...it has accurately identified deficiencies in a few people that have used it...they used the toll, took the results to their GP, GP ordered blood tests looking for the markers and bingo diagnosed problem that was resolved swiftly...massive gratification.

So, if you're bored, allow your mind to wander. Build some whacky shit in your spare time...just because you have to be available, doesn't mean your mind has to be laser focused on being available...you don't have to sit around. You also don't have to consider your job to be your primary focus in life...it's ok to consider your job to be a means to an end and secondary or tertiary in your life...work isn't even tertiary to me. I get it done and I am professional but I don't consider it to be central to my life and I don't base my own self worth on it. Its not who I am...it's just some weird abstract shit that I do that exists in its own weird bubble.

Also, consider this...you can either be known by your friends and acquaintances as that bloke that always moans about work...or you can be that guy that builds all the weird shit...if you're the latter people will start approaching you with their bonkers ideas and you end up having some really good conversations which can be gratifying in themselves because you'll explore new territory and learn new concepts that you've never considered before...which leads to more whacky shit to build!

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brusiddit@reddit

Was in this boat. Studied postgraduate to specialise and then applied for positions looking for specialists.

Feels good to be much less replacable.

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Jaereth@reddit

So you're getting 100k a year to do a job you can get done in a few hours a week and you're fully remote?

And you feel "stuck" you say? you have 30 hours a week to learn anything!

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Ikhaatrauwekaas@reddit

This is the way

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Kurosanti@reddit

Pick up an interesting hobby or a side-hustle with no conflict of interests?

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Ikhaatrauwekaas@reddit

This works, but it is probably an issue with commitment because you cannot deliver during office hours of the main hobby.

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drangoj@reddit

In 4 years i changed from windows admin to a linux admin to a cloud engineer and to now devops. I think you need to learn about it infrastructure and architecture. For me a course in AWS Cloud Architecture changed my career as I understood for first time how everything works together.

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Fallingdamage@reddit

Ive found that the term 'specialist' is kind of a misnomer.

I came to that conclusion due to the fact that as a generalist, I tend to spend more time helping 'specialists' do their job on projects more than I spend getting help from them.

A person could spend 10 hours learning Entra/O365 and call themselves a specialist. I mean, its all they know (even though they dont know much) therefore its what they 'specialize' in.

I dont have any certifications yet I spend some of my time contracting with another MSP going around cleaning up shitty unsecure configurations and messy setups because the Fortinet NSE4 tech they hired was a moron and did more harm than good.

As a good student, you can become a specialist in something while being an absolute moron at doing the actual work. When I hear that a specialist is coming in, I expect that ill have to do more heavy lifting.

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DeputyDumbDumb@reddit

I agree. In some cases, I think being a "generalist" is humble for "I'm really good at an insane amount of areas and could be a specialist in any one of them"

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jimbaker@reddit

Government work did the trick for me.

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moldyjellybean@reddit

100k Euros sounds like a decent pay for doing only a few hours work a day? Every time I’ve seen IT pay in Europe I’m astonished at how low it pays.

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xxtoni@reddit (OP)

Its a few hours of work work, I actually have to be available the whole day, keeping an eye on PRTG, someone may call, being pulled into some bullshit meeting.

If this was an actual job, I'd probably be making 60-70k. In Europe if you want to make money you need some kind of business.

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cryonova@reddit

You have Municipal Government IT Manager written all over you friend.

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JiffasaurusRex@reddit

I have about 25 years of professional experience. The first 10 years or so I was a generalist working in MSPs. I then took a corporate job in network engineering and worked up to expert level. The job after that I took a senior systems engineer job. I switched jobs in other areas of IT as well. There is nothing but time stopping you from becoming expert level in multiple areas of IT as long as you keep up with old skills as you develop new skills.

I've spent the last few years writing code professionally but still do mostly senior level network, systems, and SAN storage stuff. I'm not expert level in software engineering yet but hope to get there in 5 years or so. I used to be heavy into migrating old PBX systems to VoIP, but that skill has probably fallen since I don't use it anymore. Job hopping frequently to develop different skills has also given me a large network of peers for when I do need to look for work.

My point is that being an expert in multiple areas of It starts with being a generalist, but then taking specialized jobs and mastering them over years and then move on to the next one. At the senior systems engineering job for example I had more knowledge than the guys on the network team about networking, and they as well as senior management recognized it because I was able to demonstrate what I knew. I often helped lead their initiatives as well as the system side since they were so tightly integrated. At a later job in an architect role, having the ability to "code switch" and have deep dive discussions with multiple teams to help them connect the dots was very valuable. I don't agree with people that think if you are a "jack of all trades" means that you are not a master of any, it just takes time, like multiple decades.

I would rather keep learning and mastering new skills to challenge myself than stay in one area and be bored. Not everyone is that way and just want to chill when they get home instead of spending hours studying boring textbooks and labbing/writing code. Up to you how you want to move forward but staying a generalist without mastering any particular skills will probably limit your future opportunities.

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Paul_McBeths_Nipples@reddit

Thanks for this post. As a kid running linux routers out of cardboard boxes in my basement at age 16 to BSA rols, admin roles, IT manager roles, Sr. Admin roles, cloud roles, I know I know a lot and am at a point in my career where there's marketable. I just need to learn how to market it.

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richf2001@reddit

I focused heavily in networking. My BS is in it and I have a ton of different switches I can configure without having to google it. I STILL have to put the cubes together and plug in power cords. Heck I've had to rip car guts out. You're way more of an expert than 90% (made up number but probably not far from wrong) of anyone else they could find. Find a company you like. Google what they want and get some cert in like 2 weeks. Honestly every time I've interviewed I just let them know I didn't know but I can learn in no time flat. Pull up some google searches and give them the run down. Ever heard of Extreme Networks? I didn't. Still configured their proprietary EAPS ring when no one had a clue. That gear is still running my configs 6 years later. I wont even talk about the database software I wrote as a frickin intern cause that number doesn't add up anymore.

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moffetts9001@reddit

The issue isn’t that you’re a generalist. The issue is that you don’t have enough work to fill your day. You can just as easily, if not more so, be a specialist with not enough to do. My org is American but we just hired a German guy; dude is super smart but he wasn’t hired for any specific knowledge. There’s jobs like this out there; be patient and keep looking!

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hivemind_MVGC@reddit

So learn a specialty. This is what certs are for.

Wanna be Cybersecurity guy? Go get your Security+ and CISSP and you're the CyberSecurity Guy.

Wanna be Cloud guy? Go get Microsoft AZ-900 and AZ-104T00-A and you're AzureMan. Go get AWS Cloud Practitioner and AWS Solutions Architect or AWS SysOps Administrator and you're the AWS Dude.

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Sasataf12@reddit

Are you not being considered for those roles, i.e. getting rejected or not landing interviews?

Or are you not considering those roles because you think you won't be successful in them?

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Anonymo123@reddit

Nearly 30 years as a generalist, I've loved it. I know a good deal about a bunch of things and I never pigeonholed myself into one thing. There are things I prefer to do and steer towards, but otherwise its been a great career so far.

I've worked with small startups up to multinational and and two FAANG companies... been very successful. I personally like being a generalist, for me its easy to see how all the things fit together and it helps me troubleshoot things out of my normal experience.

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xxtoni@reddit (OP)

I like it too but all the positions and contracts want specalists. How do you overcome that?

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dagbrown@reddit

Pretend to be a specialist. All it takes is temporarily disavowing knowledge of the stuff outside of your current supposed field of specialty.

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RikiWardOG@reddit

You show them you have enough experience with whatever they're hiring for? You can still prove knowledge without specializing in it. I've picked up a lot of intune and azure skills without ever being "specialized" in it.

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SmallBusinessITGuru@reddit

The same way everyone with two years of experience do when they want to become a specialist, they apply for multiple positions, interview, repeat until hired.

Is your problem that you're looking for a role with comparable hours, wage? Because, no you're not going to jump from 10 years general experience at 100K into an senior level specialist role. You will likely need to compete for junior roles at less income and a lot less freedom.

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Grrl_geek@reddit

When ppl ask what I do, I say I'm like the "conjunction junction" of computing - I hook things up and make them run right. :-)

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garlicriceadobo@reddit

+1 for Schoolhouse Rock reference

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spetcnaz@reddit

AWS and Azure are in demand. Become a generalist in AWS and Azure at a minimum. If you can create an AWS network, the instances and the storage, basically what you would do in a new SMB office, but in the cloud, you will be able to get a pay bump and move up.

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Maro1947@reddit

I was a generalist all my career

Didn't mean I wasn't elbows deep in SANs and Routers

As mentioned, SMB will love you experience

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Coign@reddit

Fellow generalist here. I got my Project Management Professional and did that for a year. Then I went back to school and got my Masters in Business to pursue management. My experience as a generalist gave me the edge to be (in order of my last few title to current):

Project Manager (For an SMB MSP)
Performance Engineer (for Enterprise, working in Splunk/SQL tracking electronic health records as they went from lab to central DB to patient portals to report metrics on how long that took and where bottlenecks were)
Sr. System Admin (for SMB)
Director of IT (for SMB)
Director of IT Governance (for Enterprise)
Director of Infrastructure for MSP (Enterprise)

Each one of these roles did not exist at the company before I was hired to "start it" and my generalist background gave me the insight to build these roles and departments from scratch. There is a large need for generalists and each of these roles benefited for it.

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progenyofeniac@reddit

Find jobs that are looking for someone with a focus on something you know how to do, and tailor your resumé to match.

I was a generalist for about the same amount of time, decided it was time to look elsewhere, and ended up in a role where I was an endpoint engineer with a nice raise.

I’ll admit, you may have a tough time finding a huge raise if you’re already at that level of pay, especially in Europe. But it never hurts to look.

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Shibidybow@reddit

Coming back to this thread later. Good luck to you.

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awit7317@reddit

After that long you should be what I like to call a “Specialist Generalist”

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mrhoopers@reddit

Me: As a generalist and working in multiple industries I can get a job anywhere, it'll make getting laid off annoying but not problematic
World: We ONLY WANT SPECIALISTS with DEEP INDUSTRY EXPERIENCE

Me: But you only need deep knowledge once in a very long while and how is selling chairs different from selling laundry detergent? It's still servers and endpoints...the cloud...
World: CLEARLY YOU DON'T KNOW HOW CHAIRS WORK!!!11!!!

Yep, feel your pain...

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Tbzeed@reddit

Go into GRC. Better pay, and more challenging!

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Ryansit@reddit

Been in a the same boat, I have been a gov contractor for decades now for IT. It’s been impossible to keep up with tech since you get assigned one type of duty. Oh how I would love to get more access to the latest tech and online services. Sadly I’m stuck in imaging building and cyber security.

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countvonruckus@reddit

As a cybersecurity specialist that got my start in government contracting, it's actually relatively easy to specialize in this field. It requires changing jobs a few times (which sucks), but if you hop to a few different organizations (preferably in different industries if possible) then you can leverage specific aspects of your experiences with each job hop. Cyber folks tend to wear multiple hats, so if you emphasize what you did that's the direction you want to go you can lean into specific aspects of the field you like.

For example, at the government position you may spend 25% of your time doing imaging, 25% of your time doing security auditing, 25% doing vulnerability management, and 25% of the time doing general business stuff. If you enjoy it, you can apply to another company or organization as a vulnerability manager. They don't care that it was only a quarter of what you did before; they just care how many years you've done it. At the new position you get a new perspective on how they do things, and you're doing VM at a more focused level. You get better at VM and have a better perspective, maybe even learning to solve particular tricky VM problems like dealing with vulnerable EOL devices. Then you apply to a company that is likely to have that problem, such as a manufacturing organization. You're above most candidates since you've specialized a bit and you have experience solving the problem that their team apparently can't solve. After all, why would they be hiring a budding specialist if they already knew how to do it? Then you're a manufacturing vulnerability manager specialized in dealing with maybe industrial security (also called OT or ICS security), since that's where the EOL vulnerabilities were that you dealt with. Now you're someone who knows how to fix vulnerabilities in ICS/OT environments and you're a specialist.

Taking it further, once you've acted as an ICS/OT VM specialist, you learn how ICS/OT security programs function and participated in working through some of the challenges associated with that. Once you learn what works and what doesn't, you're not just an ICS/OT VM specialist; you're an OT security specialist. There aren't many of those and there's a huge need for them, so you can basically set your price and take your specialty wherever you want to go.

That's not exactly my career path, but it's the general structure of it. That process took about 9 years in government and 5 building the OT/ICS part of it. Now I've built OT security programs at several companies and organizations whereas a huge portion of companies don't have anyone that has done it even once. I can come in as an expert and do what they can't, which is a great spot to be in.

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Ryansit@reddit

Yeah I do most of this would love to get out of my current spot but love the fact I am 100% remote. Main reason I am stuck at my current job. Haven’t found anything 100% remote.

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countvonruckus@reddit

I've been remote my entire career, minus 4 months just before the pandemic. Bigger organizations often need security across many locations, so it's been fine for me to work wherever since there's no "central office" to go in to. There's been a trend away from that, but remote security jobs are definitely out there.

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Ryansit@reddit

Well shit thanks for the info I will look around for this see what’s out there.

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countvonruckus@reddit

If you're interested, IT generalists make excellent cybersecurity personnel with a bit of a pivot. That can translate into a specialist role pretty easily, and the base of IT knowledge you have will put you in a great position to enter that arena. Generalists can become IT security architects, which tend to be near the top of the cybersecurity food chain as far as technical folks go. A bit of success doing that can help you find a niche to build a company around.

The best part is that it'd probably be pretty easy for you. If you've worked in IT for 10 years on various parts of the IT space, then you probably know the fundamentals of security that cybersecurity folks need to learn in their early years. Try checking out the domains of the CISSP certificate; how many do you already know or have experience working around as a sysadmin? If it's most of them, then it's just a little security theory to learn and then you're a senior security professional with more technical depth than most.

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hundredpercenthuman@reddit

If nothing tickles your fancy specifically and you are just looking for advice on what to specialize in, I recommend containerization. It’s kind of the future of virtualization and lots of companies need specialized talent for it that they don’t currently have.

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wasserbox@reddit

Figure out what you want to do. Get a certificate in the relevant field Adjust your resume to emphasize that type of work.

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Anlarb@reddit

Generalist is just the foundation to build a specialty out of, you will probably pick up quite a few specializations.

https://www.smbc-comics.com/comic/2012-09-02

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Ok_Presentation_2671@reddit

No need to feel anything add credentials to prove your competency.

Doesn’t take long to test and get certs, why none listed?

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PMzyox@reddit

Generalist translates pretty well into devops currently.

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bythepowerofboobs@reddit

You can make a lot of money as a generalist. Find a job at a small/medium company with a large annual revenue (a lot of manufacturing and food companies fit this bill) and you can get paid very well.

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rosetacks@reddit

Forget what you aren’t, what skills do you have that you can hone or focus? Of those, what appeals to you the most and why? Start there

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Chaucer85@reddit

Approaching year 7, and not really wanting to go into leadership roles, spent all this past year working to pivot to Technical PM. Looks like it's gonna happen, just gotta keep busting my butt through this last Q1 to offload my training and expertise to the guy who'll be replacing me.

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BloodFeastMan@reddit

Just embellish your resume, it's what everyone else does. This stuff isn't that hard, we all have a gene for it, and if we don't know something, we self teach quickly.

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Zahrad70@reddit

Go get a cert in something you are interested in. Then pursue long-term (not less than a year) work specific to it. Get advanced certs then. If the cert and finding the gig take 6mos to a year, you’ll be out of that rut in two, and then that generalist experience will be very, very valuable.

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omgosaurus@reddit

You could explore the management side of things, with that kind of experience it would make sense, imo.