I’m also nervous about using an OS I’m not familiar with for business purposes right away

Absolutely STOP. Do not go with Linux, go with what you are comfortable with. If this is business, you do not have time to be uncomfortable and the learning curve to ramp up to ANY new OS and be productive is something that’s just a non-negotiable kind of thing.

If you’ve never used Linux, play with Linux first on personal time. For business time, use what you know works first and foremost.

All OSes are tools. You do not just learn a tool when your job is waiting for a bed frame to be made or whatever.

TL;DR

If you are not comfortable with Linux, do NOT use it for business.

I use linux to run my law office, so it can be done. Most of what I use is web-based these days, so headaches are minor. That being typed, I’ve been using linux off and on since the 1990s, and there was a fair amount of learning involved. A few notes:

-Libreoffice is good enough for document drafting, unless you’re extremely reliant on templates generated in Word. Even then, that’s a few hours of clerical work that you can farm out with, presumably, no confidentiality issues to flag. Also bear in mind that if you end up using different Linux distributions on more than one computer, then you may run into minor formatting differences between different versions of your word processing software. Microsoft Office will be a reliable option unless you run windows as a virtual machine. There are workarounds, but they aren’t business ready.

-Some aspects of PDF authoring can be tricky if you’re doing discovery prep, redaction, and related tasks in-house. This is very workflow-specific, so if you’re not a litigator or your jurisdiction doesn’t have a lot of specific requirements for pdf submissions, it might not be something that you need to worry about. If it becomes a problem, then a Windows virtual machine might be a solution.

-Video support depends greatly on the linux distribution, so you may want to do a bit of research and avoid distributions like Fedora, where certain mainstream AV formats are not supported by default for philosophical/licensing reasons.

-Compatibility with co-counsel and clients will be hit or miss. I don’t let anything leave my office that hasn’t been converted to PDF and I only do collaboration when there is a special request to do so. I can fall back on a computer that I have which runs Office. It sounds like you have more than one computer, so you can have a backup plan.

-Hardware support is critical. If you need to videoconference and it turns out that your webcam doesn’t have a linux driver, then you may be hosed. Research and test on the front-end so that you don’t find yourself in an embarrassing situation of your own making.

-Learning curves cost money. If you’re using an entirely new set of user software AND you’re hopping between different distributions to find the version of linux that works for you, you’ll waste a LOT of time that you could be using to generate billable work.

Starting a new business is hard enough as it is - please do not complicated it by adding in something that brings limited tangible benefits to the company, whilst making it unnecessarily harder than what it will be anyway.

Either get fluent now, and then start your business - or start your business with Windows and move on when you’re profitable and can afford the reduction in productively while you learn the ropes.

Do not go anywhere near MacOS - you can’t afford it.

Don’t do it.

First off, I love Linux. It’s my daily driver and I wouldn’t want to use anything else.

But in my past career I was the CIO at a very large firm. Lawyers need Microsoft Office and Windows. If you hire a good assistant or paralegal with word processing experience, they are going to need Microsoft Word. LibreOffice is good, but it’s not a replacement in this scenario. Good word processors are like wizards and will save you hours. It’s not worth it to make them learn something else.

Then there’s drafting software, templating, practice-specific tools, etc. Anything geared for legal is going to run on Windows. What are you using for time entry? What about accounting?

Not to mention, you have some information security obligations under the model rules and you don’t want to mess with that. Although Linux has security advantages over Windows, you still have to take measures to secure it. Maybe that’s easy enough for you to do on your own laptop, but your practice will grow to at least a few staff and an associate. Somebody has to do IT because you’re sure as hell not going to waste billable hours on it.

I had to use Windows in that old gig and it really wasn’t bad. It’s stable, reliable, easy to support. Everyone you hire will have used it before. It’s an unpopular opinion around here, but it’s a quality operating system that’s affordable. I guarantee your cost of ownership will be lower on Windows in your particular situation.

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I’m a software engineer, and I’ve used Linux on my computer for work before when my company allowed Linux installs on their computers (most don’t in my experience). I don’t recommend it for you.

For me, my main productivity tools, even proprietary ones, run natively on Linux. I very very rarely have to do anything involving word processing. When I do open source or in-browser word processors are enough. Windows can also be a constant headache to use in a lot of software development settings. It’s a horrible development environment. I try to avoid working on Windows as much as I can.

When something breaks (and on Linux, something eventually will), I have more than a decade of technical experience in computing I can fall back on to fix the issue myself. My work computer has failed to boot before and all I had to diagnose and fix the issue was a black screen with a terminal prompt. Even my company’s outsourced IT company had very little experience with Linux and I was largely on my own to fix it when things went wrong.

For you I don’t think it would make sense for basically all the opposite reasons. I imagine you’ll be doing heavy word processing and editing a lot of documents that need to be formatted correctly. Browser based and open source word processing are probably not going to cut it. I’m not sure if there are any proprietary file formats you may come across in the legal field, but if there are do you want to have to ask people “could you send that in a different format? I can’t open that on Linux.”

If something goes wrong on your machine you may not have all the experience to resolve it quickly on your own which could impact your business. Windows can break too but there’s a lot more support out there and the barrier is much lower to fix most issues (I can’t remember the last time I had to bust out a terminal to fix something on windows)

For all its faults, windows is pretty well set up for your typical use case.

If there’s a compromise here, you could try having a computer running windows and another running Linux. Having a backup in case something goes wrong isn’t a bad idea anyway. Dual booting is also an option. I made it through college for a CS degree with a dual boot Windows+Ubuntu laptop.

Whatever you end up doing, be sure to have a really good plan in place for backing up everything you need, especially files. Your computer can fail you at any time, Windows or Linux.

A lot of people lately have whined that Linux people are zealoted evangelists. You sure wouldn’t know that in this thread… Most popular jist of responses is “make sure its the right tool for the job first”

Sell me on Linux

No. I hate these kind of posts cause if you need to be talked into it, it’s not for you.

If you’re genuinely interested, just grab a distro and boot up a VM. Tinker and explore.

If you’re writing Word documents for your own use, to print, or to convert to PDF, you should be able to switch to LibreOffice seamlessly. However, if you’re emailing .docx files with the expectation that others are going to open them, make changes, save them, and send them back to you, you’re going to need Word or things will get messy. Office 365 online is probably your best bet.

I’ll echo what others are saying and tell you to learn linux at home first. Only use it for business when you’re sure it can do everything you need, and even then you might still want to keep a Windows laptop around in case you need it. Even though Linux is great, the rest of the business world still expects you to be able to work within Windows’ ecosystem.

Use whatever software your peers are using, the way they are using them. The importance of software compatibility cannot be overstated.

I have exactly zero experience in what work a law office does, but I would think it’s mostly paperwork and email? If so you can do that at no startup costs.

Pick a distro (pop, mint, whatever), and install libreoffice or one of its many variants for offfice integration.

A common misconception is that linux involves a lot of coding. Sure, it can if you want to - all the hooks for programatical access are there, for example if you want to build shell scripts for automation. But you don’t need to. It’s just an option many linux users, myself included, like to take advantage of.

When it comes to convincing you, all I can say is this: It costs you nothing to try.

The fact that there’s entire communities full of people who will spend energy trying to convince you to give it a try, rather than a corporation with a marketing budget and lobbying power :)

My general advice would be: look at the apps you use (or would need to use) on Windows. If you’re generally dealing with word documents, PDF’s, webpages, and videos that are viewable on VLC.

See if LibreOffice/OpenOffice/OnlyOffice on Windows work as expected for the documents. If not, see if M365 through the browser does (your can run Edge on Linux and accessing the MS ecosystems seem to be the primary reason many do so.

If you can’t do those things, Linux may not be for you, or at least may not meet the needs for your work.

For personal use, I’m all with users taking the plunge, seeing if Linux works for them, and/or some the adjustments they need to make. For many, it’s a matter of a different UI for the same applications/tasks, but less invasive while being more customizable. In many cases I dual-booting or a VM, in case that user runs into a special case holding them to Windows (maybe a particular game). You could also dual-boot and flip to Windows if the edge cases it’s needed are few and far between, but you’d still need to make sure to keep both OS’s updated.

For a business user who may face time crunches, the last thing I’d want is for somebody to find out that the proprietary file format they’re provided in the regular course of business only works on a proprietary software that only runs on Windows.

At the very least, grab a cheap windows license (got can purchase legit pro license codes online for cheap and then download the image for a USB installer from MS), run Linux as your primary and keep a Windows install in a VM (i.e. using KVM/libvirtd) for a bit in case edge cases emerge. For those that just need business apps (i.e. not games, graphics-intensive design tools or social hardware) that’ll bridge the gap just fine.

Another option would be to try something like Windows with Ubuntu installed via WSL (subsystem for Linux) and i.e. MobaXterm to access the various Linux graphical apps. However that pretty much gives you access to Linux tools without the OS UI, and all the headaches of running with an MS operating system as the primary.

For my own job, I could go 90%-95% of what I need purely in Linux, with the 5-10% left being stuff like editing Visio documents, screen-sharing with sound or only for a specific app (in our workplace’s conference app). Assuming you only need to join Teams/Zoom/etc conferences with audio and video, that part works fine from browser in either OS.

In short… it’s a business, so I can’t recommend just diving in, but it’s for the same reasons I wouldn’t recommend a business just switch their vehicle fleet to 100% EV’s or move their office to a different city/state/country without a well thought-out transition plan, preferably built in stages. It may work out great and overall be a better experience nearly all the time, but if it prevents work at a crucial moment without a backup plan that can still be a deal breaker.

It’s not windows.

Any bonus points for a concise answer?

The task question is:

Is Online Office 365 good enough for you? Or, is an ‘almost fully compatible’ word processor enough?

The features are there, but it’s a whole new interface to learn, and if you export to a word document, the document produced may look wonky when viewed in word. OTOH, whatever PDFs you produce, those will look right. And if Online Office 365 is enough, that’s great, because you won’t have to worry about that.

You’ll need to establish a workflow, and others in your office will need to use (and get used to) the same workflow.

It’s not a small leap for an office to take. I love Linux, but check out that it has what you need before you fully commit. Give it a try by dual-booting or by installing it on a secondary system.