The last time I went to Hawaii was in 2008, and I was on my honeymoon. I had just started work at a Big(ish) Nashville Law Firm, and I was nervous about taking a full week off, only six weeks in. (I was sort of worried that they’d deny my request to take a vacation.)
Fast-forward to this summer, 17 years later. Five years ago, I started my own law firm, and, as we planned another trip to Hawaii (with a 14 and 12 year old in tow), I began to worry about being away for two weeks and all the possible things that can come up.
Spoiler-alert: It was pretty easy.
My old law firm was run by folks in their late 60s and early 70s, and things like remote practice and cutting edge technology was never a priority (though our leather bound Martindale Hubbell collection was pristine).
When I started my own firm, I saw the rapid advances in technology made during the COVID pandemic and incorporated as much as I could.
The technology and systems that I use every day made the vacation so much easier than the one I took in 2008. For this trip, I leaned heavily on a few core tools:
- Cloud-Based Practice Management: My firm uses Clio. All case files, deadlines, and client communications are accessible online. My firm bills via Clio, and, on the 12 hour flight, I was able to get all of my May 2025 bills generated, approved, and delivered to clients…from the airplane.
- Microsoft Office: We are a Microsoft Office law firm. Microsoft is slowly pushing users to use the very secure online portal for Outlook, Word, and all the other applications. This is useful for remote work, obviously. I was able to access my entire law firm, easily, using a Microsoft Surface tablet.
- Zoom & Microsoft Teams: Client meetings ran as usual. Other than the random and exotic bird noises they could hear.
- NetDocuments with secure access: I use NetDocuments, an online document management system, so every document I needed was instantly available, but also secure. My paralegal could draft documents that I could easily access and respond to.
- VOIP Phone System: I use Dialpad (but am not a huge fan). Regardless, when a client called my office, they got me (in Hawaii) or my staff (not on vacation with me).
- E-Filing and Online Dockets: Lawyers violently oppose most technological advances, but the e-filing of pleadings (and new lawsuits) is so useful that even the most stubborn lawyers don’t fight this. In a pinch, I prepared and filed a lawsuit from a beach chair, and coordinated service of process via Proof Process Servers.
- Calendar & Time Zone Discipline: Hawaii is 5–6 hours behind most of my clients and courts. That meant early mornings — I typically started work at 4:30 or 5:00 AM Hawaii time to stay in sync with the mainland. This worked pretty well; instead of emails “trickling” in during the morning, I had a full plate of emails to power through with coffee, and I’d check in again at lunch by the beach (when my banker clients had gone home for the day).
What I Learned
- Time zone planning is everything: Build your schedule around your clients’ time zones, not your own. Having said that, to keep my family happy, I had to close the laptop by 8am in Hawaii…which was 1pm Nashville time. The time difference actually worked in my favor, as I had ample time to work, and then have guilt and distraction free days at the beach.
- A tight schedule keeps you focused: Being away from the day-to-day distractions of the office actually helped me focus. With a solid daily routine (coffee, sunrise, email triage), I found my time blocks more productive.
- Clients don’t care where you are, as long as you’re responsive: Big law firms cling too tightly to the old vestiges of tradition — fancy offices; suits and ties; strict hierarchies. For me, no clients cared that I was working remotely, because every call and email was answered promptly.
Final Thoughts
There are different mindsets when talking about running a law firm remotely. Some lawyers (the ones that may not have school age children) have the flexibility to run a truly remote firm, working in a new and exciting city and without being bound to a single location or your law partners’ judgey faces.
For me, I just needed to have a reliable tech-stack that would allow me to service my clients effectively while I was away. I had spent months preparing, blocking my calendar during that time, and warning clients about my limited availability.
It’s never easy to take a long vacation, especially if you are a busy solo lawyer, but it can be done–and fairly easily.
Creditors Rights 101 