Dear Attorney, Your Bookkeeper Deserves A Vacation (Everything is Going To Be Fine)
9 Jul 2026 · 22 min
Lynda Artesani, Sarah Prevost, and Stephen Libhardt argue that bookkeepers need real vacation time, not just coverage plans. They walk through a firm that resisted one bookkeeper's time off until a crisis forced them to document everything, then compare legal software like Clio, LeanLaw, and CosmoLex on integration and support.
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Welcome to Accountants Law Pod, where accounting professionals and law firms converge. Hosted by Lynda Artesani, Sarah Prevost, and Stephen Libhardt.
Welcome back to the podcast, everybody. And it's been a while since I've been on. I traveled a little bit and I had some fun when I was in California. I got to be with Sarah for quite a few days and then I tripped and fell and then I have a broken shoulder. Fractured shoulder. I don't think it's that bad, but we'll see. I still in the find out mode, but I miss you guys.
We missed you.
We missed you too, and we're glad you're safe.
Yeah, I want to come up with a better story, Steve, because it's a really lame story.
I was just gonna segue into one for you. I want to know what shoes you had on when you fell.
Sneakers.
I had sneakers on.
Oh, for goodness sake, Lynda Artesani.
I had sneakers on, and it was— just didn't see the tile that was lifted, and I went flying. And, oh, you know when you're tripping and falling? Like, I've had that happen walking home from the gym even, where some of the sidewalk is out of whack and I've hit my toe, but I've always managed to stay upright. I just, oh, yo, look, bring me back up. And this time it didn't. I went flying pretty hard and it was tile, so I landed on my shoulder. And so it just cracked a little bit and it's growing back, but I have to wear a sling, but it's really warm here right now, so I'm just gonna hang up the wall.
That's a downplayed version, but yeah.
I was gonna ask then, did you hide the gin bottle before you got to the hospital?
Oh, I don't drink, so no.
Oh goodness. Okay. I'm trying to find a reason for why you fell down, but I fell because it was a raised tile in the hallway. So glad you're okay though.
It was not great, but I'm trying to make it. But this week we're going to actually have a good conversation about— I love the title. It's called Dear Attorney. I had, I think when I wrote the blog post, it was Dear Mr. and Mrs. Attorney, but Mr. and Ms. Attorney, your bookkeeper deserves a vacation. Everything's going to be fine. Great topic. This actually happens IRL in our company where we have one particular client that just doesn't like the bookkeeper going on vacation and we have to all scramble. It's actually a good practice though, because we did switch people into that role and let them do the SOP, which helped us to make sure that the SOP was finessed so that anybody sitting in the seat to fill in could actually do it. So in a way it was a good action, but everybody deserves a vacation. I just took one and it was great except for the breaking of the shoulder. And I started out as work vacation, became just a vacation. I got some extra sleep. I think that's important.
I think the work vacation doesn't go together. It's just we had a working event.
Yeah, that's the thing. We— the beginning of the trip was just us working in a conference and all that. So it was that, and then there was just some extra days added on that I was kind of in vacation mode a little bit.
Not—
I'm not looked at my— I did not look at my phone. This is the important parts of going on vacation. I didn't really look at my phone. I had full confidence in Everybody that was, because Sarah was actually away at the same time. And so both bosses were gone at the Proper Trust and it worked beautifully where everybody, Nicole took the reins and everybody did their job and there was no fires that I'm aware of.
Nice.
If there was any, we didn't know about them.
It's a good, it's good for everybody. It's good for the homeowner. It's good for the staff. It gives them opportunity to find where they're most dependent on you, where they can grow. But I think you said it best, Lynda. It's everyone deserves a vacation and it's unfortunate that some people in this world still feel like no matter what, the service is the service and I get the service.
I mean, and the work's getting, the work got done. Even if the employee was on vacation, when she got back, she did the work. It's not like the work didn't get done. I think she did the work on the Sunday that she came back. She was, oh wow. All employees, she was like freaked out about, we all do this, right? We come back from vacation. Vacation and we look at the giant mess and the 600 emails that we have to address and you try to organize through it and how far behind we were away in the beginning of the month, God forbid, between the work part and then the vacation part. And then God forbid, now you got to— we, Sarah and I both still handle our own accounts. We do some accounts on our own just so that we stay in tune with work and knowing how to do the work. And I think it's important and we both do it and we both had sales tax deadlines when we came back and with our other clients and it was just interesting. To get caught up. Yeah, you'd have to work on the weekend. I worked all weekend trying to get caught up this weekend because it was the first weekend back, but I felt more refreshed. I feel better because I slept a lot on the trip, which I really needed sleep, and it was something lacking before I left. And you had it all planned out, I was going to sleep on a plane, and it didn't happen the way I wanted it to. But yeah, I think everybody needs a vacation to get away from the computer and get outside and get in the light and get into the nature and have a good time and just chill and not think about work.
There are no heroes created by not taking a vacation. You become a control freak if you don't, and people resent that in your office.
And we saw that with a client one time where the one of the employees didn't take a vacation for 25 years. Oh my, never took a vacation, just kept— and it had an accrual. So maybe he thought that was his retirement plan, I don't know, but he never took a vacation, never. And that is not a good practice. I think everybody needs to get away from this.
Yeah. Yeah, definitely.
Interesting point too, Steve, that you just brought up. Like nothing good comes of it and you really—
nothing good comes of it. It's not healthy.
Yeah. Yeah. You do need, it's something that like Lynda is saying, the reset. You need a reset moment. Everyone needs it in their lives.
Yeah.
We actually changed our contract. So I think it's in the contract now that says the bookkeeper will have a vacation and your work will get done, but they will not work on the week that they're on vacation.
Yeah.
I think we did.
We can have, like most people, you have supplemental support, I guess is the best way to describe it. It's not something you just drop somebody new in and just take over. There's some intimate working details that happen in a file and you want to make sure that the basic coverage is happening. So I believe that in my opinion and how you structure this is you need some sort of outline of you're going to have the basic structure of what is pertinent, that needs to get done. If there's deposit tracking, trust release of information, so forth, everything, all the extra stuff that's not as dependent, let's say, of a particular deadline, that can wait, and that can be done if it's easily possible for someone to get done on the extra time that they have. Great. Otherwise, if you think about it, I want to flip the cards around. You've got a law firm and you've got 12 attorneys going out. And someone's caseload is going to get handled, what happens then? How are you going to— you're just going to dump it on everybody? Or is there a junior associate that kind of updates another partner on what's happening? So the question has to go in the reverse. If you're a solo firm, what happens then? Do you have a contract colleague that helps you?
If there's no fires, usually, like bank feeds, that can wait till the bookkeeper comes back. It's a bank feed. It's not going to change the world. But like you said, If it's billing or positive pay, for example, those things have to be done every day, and we just have a backup system where somebody else will log in and make sure that the positive pay is done. Or if they're needed to get a check out for something or anything like that, that all happened. It wasn't like it didn't happen. And I think the bookkeeper actually was like, I prefer I do it myself because I know the details of the file and I don't have to come back and fix stuff, which Fortunately did not happen. She didn't have to fix anything, but I think sometimes it's like she protective of her work, right? And just knows the client really well, but we managed through it. And I think all in all, the positive out of it was we were able to improve the workflow a little bit. Things that like links to things weren't there and our other bookkeeper went in and just kind of tweaked it so that it was ready for next time. So that was a good part of it. But yeah, I think, I think most people though are okay with being on vac— the bookkeeper taking a week or two off. A year? I don't think that's—
if you're an independent bookkeeper or an accountant or accountant, whatever, it's about communication with the client. It's okay to call the client up and say, hey, I'm going to be on vacation at this time. If you're solo and you're on your own and you don't have anybody else to back you up, then you tell them if it's an absolute emergency, you know where to find me, but I will be on vacation. They, I've never had anybody disrespect that. And in my own life, you guys know I'm an entrepreneur, so I will work extra hard before and after vacation. And then I do take my work with me. I've got it with me. I take a laptop with me. I've got everything, every tool I need. And if there's an emergency, I'm on Starlink and they can find me and I can answer the question, transfer the money, do whatever we're doing. And right now we're in the middle of a huge— and this is huge— bank merger going on here in Colorado. And a lot of the clients are on it. You've been through that before. And so I'm dealing with that. In the midst of this vacation I'm taking this week. And so it's just a matter of getting, being a little more aggressive with the bank when I call and say, let's get this done.
Exactly. I think the big thing too, that our experiences, and I understand this, I'm not telling everybody I work with or my—
yeah, we're not doing a finger blast that we're going on vacation.
However, I do feel that when you have such a partnership relationship, which is what Proper Trust works in, and you're the firm owner heading out of town, it is respectful courtesy to inform us so that we understand we're not disrupting you while you're on vacation. We're not asking for things that we would normally expect to be asking for in that timeframe. And like you said, Steve, most firm owners like ourselves, we all work. So it's understandable if you're going to reach out while working, but then set precedence. I do that when I travel. I always set, especially when I'm in Europe, I will say I'm available between these times. I can meet you between these times. I'll shift my meetings to accommodate that. Like you said, my work doesn't stop either, but there were things— there will be days where I'll call it blackout week and say I'm out, I'm unavailable, maybe an extra couple of days here and there. But yeah, I do feel what Lynda and I experienced, like whether, you know, you do a retreat as owners to make this work and that just coincides with a work professional event, a learning event, that seems to make the most sense sometimes. But other times you can just do an actual team retreat or something like that. That whole out will impact as well. And it's sad that we had to put it in our agreement, but for those accounting folks out there, that might be something to consider depending on the type of profession you're servicing. Or I've always been told, and I don't know if you remember this, but we were told you should have a somehow a backup system. If you're out, somebody else can help out. But that's also really tricky because it can be If you're solo, that's hard.
If you're solo, it is tricky, but you could do that.
But I love the title, Dear Attorney, Your Bookkeeper Deserves a Vacation.
So did you see me jump? Yeah, they're working in the house. I saw you working in my house and all of a sudden they do something.
I'm like, ah, we could flip it to Attorney, You Deserve a Vacation.
Yeah, a lot of them don't. But that's the thing with solos. A lot of times they don't vacation and they do deserve a vacation for sure. We also had a question on our YouTube about, remember when we did the kind of a playoff of LeanLaw and Clio, what's the best software? And somebody said the legal software showdown, and they wanted to know what about Karat and TimeSolve and Rocket Matter, especially Karat, which seems to be nearly as comprehensive as Clio. Karat, AKA, as Steve looked up before we started, Abacus, which was the original name of it, and then they changed it to Karat. My head went right to the vegetable. I did not think of the diamond when I thought of a carrot, but it's carrot that's more like a diamond.
You had a good point. What did you call it, Steve?
I don't remember.
Amnesia just set in right now.
Conveniently.
Yeah, I agree. When it's a product that we have seen, we've not actually worked it in. Does look nice. It looks better than what it looked like a few years ago when we first saw it.
And it's an all-in-one. So no QuickBooks, no Xero. It's all in one. So you have all in one, like a CosmoLex, right?
Yeah. And we've worked—
which limits you, which will limit you because now doesn't have the integrations. Payroll, it must have some payroll kind of integration, right?
Having had worked, I worked with Abacus in the past and it was not a pleasant experience.
No, that's not a nice way to say that.
That was very kind. That's not how you said before we started the meeting.
Oh, I know, but trying to be professional. Professional here. It was a rough ride with that software. So I'm sitting here thinking that maybe they had enough pushback finally that they were pretty antiquated, and they were. And it's kind of nice to see that maybe they're morphing into something more professional and friendly, user-friendly.
Yeah, we have worked in TimeSolve and in Rocket Matter. There are actually other platforms that we work in too.
Rocket Matter wasn't too bad. I was able to poke around in there.
Did it integrate with QuickBooks?
Parts of it. Parts of it did. Parts of it did. What I had a struggle with in that particular product was getting the actual— you could see inside the product certain numbers and you could figure stuff out, but they had a confusion at the time, and this was about 4 to 5 years ago, between operating and trust, the way they used to lay it out, the operating retainers and trust retainers. And there was, by user, there was confusion. So ultimately resulted in data being confused. Yeah. I'm not saying it's that way now.
Did it have, did it have the, was it the one that you couldn't record a partial payment? I know my case, you can't, you have to record, like, you can't record like one check with a bunch of invoices. You have to record individual, which could equal a total of the check. But I don't know if that's the case with Rocket Matter. I'm trying to remember. If that was one that you couldn't enter partial, like a not fully paid invoice.
Yeah, I know, I follow you. I'm just trying to remember. It's been a while. Exactly. It's been a while. I'm happy this question came up. These are areas that we are happy to pursue and inquire if they would like to join us on a conversation to discuss their softwares and where they stand today. And personally, I would like to know their roadmaps. I would like to know where they're going because Partly why we sit in the two other modules is because we have some very strong relationships. We know where they, where their roadmaps are going, not maybe so clearly sometimes, 'cause Clio's a big company, but we get some really good support and understanding of it. And so yeah, we would be happy to have those conversations and help highlight and understand what you're asking so we can provide a better showing of the other softwares.
And it's important to, to learn what type of law firm they support, the software supports. Is it, is it, do they target the solos? Do they target the midsize? Do they target the large firms?
They, what I love, what, that's a good point, Steve, because when I first went and looked, there's so many that cover all the buckets and all the practice.
One size fits all.
But as we know, it's like what Lynda always says, this, it's QuickBooks and Xero is a ledger system and you put a suit in front of it, whatever that is. There is beauty if you think about where we are today and now. There is beauty in non-all-in-one systems, and there's beauty in having all-in-one systems. It's just dependent on your firm, the workflow, and what's needed. And that's the whole difference there too, is looking through that lens. A lot of times what we like is what we're seeing right now is some advances in LeanLaw and, and Clio equally where they're working better sometimes with these systems that they may have a similar product in product. It might be somewhat parallel, but not as robust. I like that. I think that's—
I like the versatility of being able to go into QuickBooks and be able to, because it's a GL, it's got a ton of reporting, it's got a ton of other features.
Exactly.
And then you've got the other layer of Clio or LeanLaw on top of it where we can get all the details on the customer side of things and extract that out. I think that's a nice— because both of those products, Xero and QuickBooks, have a lot of integrations. Clio has a lot of integrations. LeanLaw has some integrations. A lot of the all-in-ones don't. They're siloed off. And then you gotta find a bookkeeper that knows how to use the per product, or they have to learn on the job because they're not gonna sit in the seat and they'll have QuickBooks background or Xero background. I've used this software, but very unusual to say I'm an expert in Karat. Maybe there are some people out there. But I think that they have to learn it. And that's another part of—
one other part of the point is so spot on. And Steve, you've brought this up before, is the specialized— yeah, we're specialized, we know our niche, but to go one step further and be at this point, if you look at our firms independently, we are beyond accounting. We're operationally helping you design things. We're doing IT support. Not that we take IT on, but just the integration of the accounting softwares. We have to understand that data. —set of information that moves back and forth between product. We have to know how to troubleshoot it. We spend a lot of time with support calls. I would like to know how open are you in working with your partners? There's some criteria on the accounting side that I'd like to know, and there's some on the firm side. And then who within your firm is the best person to work with? Who's going to learn it? Because we often see it. Most people jump into firm softwares, practice management softwares, and they use about a quarter of it. And they're not fully—
What was it? Didn't we just see the other—
where was it? Yeah, we had LeanLaw. We had Jonathan Fishman. He gave us that.
Yeah, 80% of the— yeah, of the people don't use the whole program.
Precisely. Yeah, that's true. We see that all software because we're the same way.
We're using Carbon and we're making sure that we use all the goodness of it because what's the point in spending the dollar that we're spending on it if everybody's not using it and they're just touching the edges of it, if you're not really going deep, you picked it because it had all these features. Why not use them all? And that's, I think that's important. And I think that those are the things you got to think about. Also, Sarah, you just touched upon it. When you pick up a software like a Karat, a TimeSell, how is their support? Yeah. Are you talking to a chatbot and it's really difficult to get through? I mean, I know QuickBooks isn't that great unless you've achieved the levels, right? But how good is the software support? Because that's, you're locked into that. There's no other software but Karat, right? That's it. That's your software. So it better be good support for you because that's all you have.
Expensive to date a move. Expensive. It is expensive.
That would be really expensive if you want to get off of it, because now you got to put the GL side into— if you want to go to a Clio.
And then the interface, what's going to come over? What's— oh yeah, there's that whole basket of money.
That's a big decision to make if you go into an all-in-one.
I can tell you very, very— just kind of a benchmark idea. If you think of the figure around $4,000 to $8,000. Roughly for data migration, depending on the size of your firm. Yeah, that's what you're looking at because it is tedious work. Yes, in this day and age, a lot of data can move, but is it moving correctly? Is it the right data? Do you have the right people? We go through a lot of diligent reviews to ensure, do we have everything lined up correctly? Do we have the right information? Does it balance back? Does it actually tie out to your tax return? All of these little nuances. And I'm just throwing out a number out there just for understanding of, hey, I made a mistake, or my paralegal said to do this, and then come to find out it's not been great. I looked at a product that a client's been in for some time, and I found so many manual admin hours being spent in that product. It was— honestly, it disgusted me because I was like, we're losing a lot of money. So that's a big thing. Pay it one way or the other.
Manual processes. Is it manual? How much of it's manual? The benefit of an all-in-one is you've got the three-way bank reconciliation is right inside the product.
Like we've seen with Cosmolex, some of the detrimental costs with that.
Yeah. How locked down is it? Can you make changes if there's a change? If you're dealing with the same amounts of money coming in and you accidentally put it against the wrong account, do you have to unravel everything because it's locked down like a vault when you reconcile it. Yeah, those are the things you need to really look into.
But yeah, we went out with the winner, but that was a good question. Thank you. Yes, very good question. Now we've got our minds rolling.
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Thank you, everybody. Take a vacation now. I'm gonna do that. Yeah, you are. Bye.
