How to Actually Relax on Vacation as an In-House Lawyer (Without Letting Anything Slip)

Deep Dive

Preparing for Vacation

Want to know something I truly love? Like, something that brings me immense joy and I’d be seriously bummed to live without?

Vacation.

I love it for myself, and I love it for my team.

Whether I’m relaxing in an upscale hotel between days of sightseeing and great food in Cape Town, running across the Grand Canyon (and back) for the challenge, or doing something more “normal” like spending a few days on the coast of Maine, vacation recharges me. It brings me joy.

And when I see my team taking their vacations, whatever they choose to do, I see the same thing: people loving their lives, and coming back happy, rested, and ready to go.

If you’re thinking: “I’m the team lead, I don’t have time for vacation,” I would strongly encourage you to re-think. As a GC, one of the most powerful signals you can send is that rest is respected, rather than just permitted. You do that that by taking your own vacation.

Let’s be honest: vacationing with kids isn’t always relaxing in the spa-scented, feet-up sense. But even when it’s chaotic, it’s a reset. It’s connection. It matters.

The same goes for time off when travel doesn’t fit your budget or life circumstances. The change of pace is important and valuable.

If your team can’t function without you for one week, something’s broken—because what if you win the lottery and leave? (Yes, I’m going with the best-case scenario. The world’s heavy enough already.)

But here’s what I’ve learned: you can’t just take a vacation and expect it to be restful. You have to set yourself up before you go if you want a real break.

That’s what this issue is all about: the concrete steps you can take to set yourself up for a real break, on your terms, and make your return to work smooth and stress-free.

With summer in full swing, whether you're jetting off, road-tripping, or just staying home in stretchy pants, a little prep can turn your OOO into an actual break, rather than just a different place to answer emails.

1. Months Before You Leave

Laying the groundwork early makes things easier for you and for everyone you work with. Here’s what to do in the earliest phase of your vacation prep:

• Block your time. After getting any required approvals, add your PTO to your calendar and any relevant shared team calendars. On my team, we use a formal process to request and track PTO, and we also send each other calendar invites as a helpful reminder. That approach doesn’t work for every team, but it’s been great for keeping track of who’s out when (when I’m looking at my calendar on any given day, I can see right up top whether anyone is out). The earlier you block your time, the less likely something important will get scheduled over it. Added bonus: studies show that looking forward to your vacation brings as much (or more) joy than actually experiencing it. Planning it early also means you get more time to look forward to it!

• Shape your legal work timelines. Look ahead to key deliverables like contract signings, regulatory filings, or deal closings, and begin adjusting timelines or sequencing your work to avoid a crunch right before you leave. A little planning now can prevent a lot of fire drills later. Pro tip: deadlines shift often, sometimes because the business moves them, sometimes because counterparties delay. Build in buffers where you can so you’re not knee-deep in a redline or filing the day before your flight.

• Communicate early about high-stakes meetings. If you’ll be out during a critical meeting or milestone like a board meeting, quarter-end push, audit committee prep, or important negotiation, flag it early. Depending on your role, you may need to plan around these moments. But when that’s not possible, don’t just hope it’ll resolve itself. Advance notice helps others prepare, ensures coverage is in place, and keeps the business moving in your absence.

• Schedule time for the prep work.  As soon as your vacation dates are set, block time on your calendar (ideally a month out and again a week out) to handle the tasks on this list. It’s the best way to make sure nothing falls through the cracks and that you’re pacing your prep realistically.

2. One Month Before You Leave

With about a month to go, it’s time to shift from blocking time to coordinating with your team and the colleagues your support. This is when you make sure the right people know your plans, and that no one’s caught off guard when you're out.

• Give advance notice to key stakeholders. Remind your manager, legal teammates, and cross-functional partners of your upcoming PTO dates. Flag the legal matters that will still be active while you're out, whether that's a contract in final negotiation, a policy under review, or an open compliance issue. It doesn’t need to be a big production. A quick note or check-in does the job. Bonus points for highlighting any decisions or approvals they'll need from you beforehand. A little clarity now prevents confusion later, and builds trust that things are under control.

• Plan for coverage. Not everything needs coverage, but some things will, like ongoing contracts negotiation, key fundraising activities, or active litigation. Take stock of the responsibilities that will be active while you’re out, and identify who’s best positioned to step in. Depending on your role and the structure of your team, this redistribution may be something you do yourself or in coordination with your manager. Either way, it’s important to give people time to prepare, ask questions, and get up to speed.

• Start drafting your handoff. Even if it’s rough at this stage, getting a head start on your handoff doc makes the final week easier. Begin capturing key projects, deadlines, contacts, and anything you’re waiting on. It’s will help the people covering for you, and give you a great place to pick things up when you return.

3. One Week Before You Leave

With just a week to go, it’s time to shift from planning to execution. This is your window to finalize handoffs, tie up loose ends, and make sure your team and cross-functional partners are set up for a smooth stretch while you’re out. A little extra communication now can save everyone a lot of stress later!

• Send a “pre-out-of-office” check-in. Remind key partners you’ll be out next week, ask if there’s anything they need from you, and confirm coverage.

• Start preparing your handoff doc. Include project statuses, key dates, contact info for coverage people, and helpful links. Make it easy for others to step in—or leave things alone. While you’ll want to finalize this immediately before going out, having it substantially complete in advance means you’ll spend less time on it when you’re also trying to finish urgent tasks- and you can give it to people in time for them to review and ask questions.

• Set a meeting to review your handoff. About a week before you leave, schedule time with your manager (if they’re coordinating coverage) or with the colleague primarily stepping in for you. Aim to review the handoff doc together a day or two before your last day to make sure everything’s clear, aligned, and ready to go.

4. Last Day Before You Leave

You’re almost out the door, but a few final steps can make a big difference. Use your last day to wrap things up, reinforce your plan with the team, and set your future self up for a smoother return. A thoughtful departure helps everyone feel confident and covered while you're away.

• Set your out-of-office message. Keep it clear, friendly, and informative. Include the dates you’ll be out, when you’ll return, and who to contact while you’re gone. If relevant, link to your handoff doc. And triple-check that your backup contact isn’t also out of office—there’s nothing more frustrating (or more avoidable) than an auto-reply that sends someone in circles.

• Finalize and share your handoff doc. Make sure everything is clear, up to date, and easy to follow. Include project statuses, key dates, helpful links, and contact info. Even if your coverage is light, the doc helps others feel confident—and prevents unnecessary messages while you’re away. Make sure your team knows your level of availability while you're out (more on this below).

• Leave breadcrumbs for your future self. Jot down a few quick notes in a document or email about where things stand, what’s pending, and what to prioritize when you’re back. It takes five minutes and saves you an hour of context-switching later. I find it helpful to make this an annotated version of my handoff doc.

5. While You’re Out

In 2025, it’s rare to be truly unreachable. But just because people can contact you doesn’t mean they should. Be clear with your team about your availability while you’re away, including what is technically possible, what you’re comfortable with, and what makes sense for the business.

What’s appropriate will depend on several factors: your role, your company’s PTO policy, the nature of your vacation, and your personal preference. Some people want to unplug completely and avoid work communication altogether. If that’s you and works in your role, great—say so, and make sure coverage is solid.

Others prefer to stay lightly in the loop. Personally, I prefer that my team reaches out while I’m away if I’m a blocker or can provide a quick answer to keep things moving. They know I likely won’t reply right away, and they also know I’ll check in. Most of the time, I’ll spend an hour or so in the evening replying to emails. That rhythm works for me—it keeps things on track and makes reentry easier, without taking anything away from my vacation.

Whatever your preference, the key is to decide in advance and communicate it clearly.

A little preparation goes a long way.

Taking vacation is awesome. And it’s extra awesome when you have taken the steps to ensure things run smoothly while you’re gone. That confidences lets you truly rest without anxiety about what’s happening in the office hanging over your vacation.

When you’re thoughtful about the lead-up, intentional with communication, and realistic about your preferences, you set the stage for a real break, and a smoother return.

Bonus resource: I pulled all the key steps into a simple checklist you can download and use to prep for your next vacation—whether you’re unplugging completely or just dialing things down. Download it here.

Are you going anywhere exciting this summer? Or have you planned a restful staycation? Hit reply and let me know. I read every email.