Hi there! It’s Heather Stevenson.
Happy Wednesday and thanks for being here! Here’s what’s covered in today’s issue:
Practical tips to help you prep for vacation and actually relax while you’re away
A free guide (in case you missed it) on how to intentionally build an in-house career you truly enjoy
Smart, curated links worth your time
And a little more
Let’s dive in.
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.
