OG Tuesday Issue #300

📊 Habit tracking is the cheapest productivity hack that compounds.

⚡ Turns out AI doesn’t lighten your workload, it speeds everything up.

🔮 What the summer solstice means for every star sign.

💸 Nearly half of women have no emergency fund right now.

There’s a version of going on vacation where you spend the first two days mentally running through everything you might have forgotten, answering “quick questions” from your team, and refreshing your email just in case. And there’s a version where you actually unplug.

The difference is almost entirely in how well you prepared before you left. Every summer, we write about this because it’s a challenge every holiday.

Whether you’re taking a long weekend or two weeks off the grid, here’s how to set yourself, your team, and your inbox up so you can actually be present for the trip you’ve been looking forward to.

Tie up your loose ends early

Don’t save your prep for the day before you leave. Start wrapping things up at least a week out. Identify every project that’s in flight and decide what needs to be completed before you go, what can be delegated, and what can wait until you’re back. Write it all down so nothing is living only in your head.

For anything you’re handing off, be specific. Don’t just say “you’re covering X.” Create a brief document that covers the current status of ongoing projects and their deadlines, who the point person is for each workstream, where to find the relevant documents and logins, and how to reach any external contacts like vendors or clients if something comes up. This OOO coverage plan template is a clean way to organize everything in one place.

Write an OOO that actually works

Your out-of-office message is doing more than you think. A good one sets expectations, redirects urgent needs, and gives people everything they need without having to reach out to you. A bad one just says you’re gone and leaves people guessing.

A few swipe-worthy formats:

• For the warm and practical: “I’m out of the office until [date] enjoying some well-deserved rest. For anything urgent, [colleague name] at [email] has you covered. Otherwise, I’ll be back on [date] and will respond then.”
• For a little personality: “Currently sipping something tropical with a tiny umbrella. I’ll return on [date] with a clear head and possibly a sunburn. For anything pressing, reach out to [colleague name] at [email].”
• For when you’re fully offline: “I’m out of the office and intentionally disconnected until [date]. I won’t be checking email during this time. If it’s urgent, please contact [colleague name] at [email]. Everything else will get my full attention when I return.”

Block your re-entry before you leave

This one is easy to forget and makes a huge difference. Before you close your laptop, block the first day back on your calendar. No meetings. Just time to get through your inbox, triage what actually needs your attention, and ease back in before anyone pulls you into something.

Pick your top three priorities for the week you return and write them down somewhere you’ll see them. Coming back to a clear, short list is a lot less overwhelming than coming back to chaos.

Use a prompt to help you prep

If you’re feeling overwhelmed by everything you need to tie up before you leave, this is exactly the kind of thing Claude is useful for.

📋 Try this prompt:

“I’m going on PTO from [date] to [date]. Here are all the projects I’m currently working on: [list]. Help me figure out what I need to complete before I go, what I should delegate and to whom, and what can wait until I return. Then help me draft a handoff document I can share with my team.”

You can also ask Claude to draft your OOO message, write a pre-vacation email to your team, or create a day-by-day wind-down plan for the week before you leave.

Actually log off

This is the hardest part for a lot of high performers, and it’s worth saying directly: checking your email on vacation is not the same as resting. Your brain needs real downtime to recover, and that requires a genuine break from work inputs.

Set app limits on your phone if you need to. Put Slack and email in a separate folder and move it off your home screen. Turn on Do Not Disturb. Tell the people you’re traveling with that you’re going to be present.

Rest is part of how you show up well when you get back. Let yourself be all the way off, guilt and all. The work will still be there when you return. The trip you’re on right now is the part worth protecting.

Think about the last time a card came around the office and a dozen people had written something real on it. You probably still remember how that felt.

That feeling, being genuinely seen, is one of the kindest things you can hand someone, and right now it’s free to give.

Right now, GroupTogether is giving you your first group card free (a $5.50 value), and it only takes two minutes.

Someone already coming to mind?

• A new hire joining that you want to welcome to the team
• Someone on the team going through a rough stretch
• A coworker who is leaving and deserves a heartfelt goodbye

It’s just as good for life outside the office:

• Thanking the kids’ teacher/coach
• A birthday card the whole group chat signs
• The whole crew coming together for someone’s big news

Everyone signs one digital card from anywhere in the world and the recipient sees a personalized card opening animation that actually wows. It’s why 5,000+ companies (including us at The Assist!) use it.

Send one today and feel how good it is to make someone’s day. Every card includes unlimited messages for one flat price, and you can add a gift collection without chasing anyone on Venmo.

Claim your free card through to the end of June, good to use through December 31, 2026.

👉 Claim your FREE group card.

“My biggest challenge right now is finding work in the current job market after being part of a RIF. Not just work, but work that fits, is exciting, and the right pay.” — Kristen C.

A layoff is hard enough on its own. Add a tight market and the pressure to find something that genuinely fits, and it can feel like threading an impossible needle. A reframe that helps: this is house hunting for your career. The right place, the one that’s exciting and pays what you’re worth, takes longer to find than the first listing that’ll have you. Be patient here. You’re not behind.

Grieve before you grind

Before you dive into applications, name what happened. A layoff says nothing about your worth, though it still comes with real loss. Give yourself a beat to process it before sprinting into the search; a clearer head makes better calls about which roles are worth your time.

Understand the market you’re in

The job market is really several markets at once, split by industry, role level, location, and how clearly you match what employers need right now. Knowing which one you’re in tells you how to position yourself.

Start with people before postings

Your network is the fastest path to a role that fits; people who know your work can vouch for what a resume can’t. Reconnecting with former colleagues before you’re desperate lands better than a cold ask the moment you need something. Keep the message simple: “I was part of a recent layoff and I’m exploring what’s next. If you hear of anything that feels like a fit, I’d love to be on your radar.” Most people want to help; they just need to know you’re looking.

Get your resume working harder

Tailor it to each role instead of blasting the same version everywhere, and lead with outcomes over duties. Quantifying your accomplishments with real numbers gives a hiring manager something concrete: “Responsible for onboarding” says little; “Cut onboarding time by 30 percent” says a lot. If you haven’t touched it in a while, get a second set of eyes, a friend in your industry, a career coach, or even a few minutes with AI to catch what you’ve stopped seeing.

Upskill while you search

A layoff is also, frustratingly, an opening. Use some of this time to sharpen something that makes you more competitive: a certification, a tool your field suddenly expects, a skill you never had bandwidth for. It doesn’t need to be a six-month commitment; a focused few weeks signals you’re moving forward.

Post like a thought leader

LinkedIn is more useful than most people give it credit for, though less for “open to work” posts and more for sharing what you know: a take on your industry, a lesson from a project you led. That builds visibility job boards never will and puts you in front of people before you apply. It’s a great time to build your personal brand.

Lean into your humanity, especially now

This is the part that matters most. AI has flooded the market with resumes and cover letters that all sound the same, and hiring managers can feel it. Generic, AI-written applications are increasingly filtered out before a human reads them. That’s your advantage: write a cover letter that sounds like a real person, reference something specific about the company, tell a real story about a problem you solved. In a sea of polished sameness, specific and human gets remembered, and your relationships, voice, and experience are things AI can’t replicate.

Negotiate even when it feels like you can’t

When an offer lands below what you need, it’s still worth a conversation. Layoffs push you to grab the first thing, but a role that underpays or underuses you often leads right back to searching within a year. A short, respectful negotiation is almost always worth the discomfort.

Give yourself grace

Finding the right home for your career was never going to take two weeks, and the wait isn’t a sign anything’s wrong, it’s a sign you’re being selective about something that deserves it. The right place is still out there; you’re just taking the time to find it instead of settling for the first door that opens.

We’re always looking for ways to improve daily life. A better morning routine. A more productive workspace. A healthier meal plan. But sometimes the most noticeable upgrades are the simplest ones.

Think about how often you touch your clothes, sheets, towels, and favorite sweatshirt. They are part of nearly every hour of your day.

Laundry Sauce turns an ordinary chore into something that feels a little more luxurious. Their premium laundry products are made with fragrances developed by luxury perfumers, so your home, wardrobe, and linens smell incredible.

It’s a small detail, but one you notice every time you get dressed, climb into bed, or pull a fresh towel from the closet.

Basically, it’s the easiest way to make a chore feel a little more luxurious, without adding a single extra step to your routine.

Explore the collection here.

📆 Learn how to manage a blended team of AI and humans at this free event. Reserve your spot on July 16.

💍 A travel jewelry case that keeps everything organized instead of tangled at the bottom of your bag.

🛠️ Floot is a vibe-coding app where you can build whatever you can imagine.

🤌🏻 A crisp white linen button-up that works at the office and on a beach chair.

 Upcoming Events

• TODAY 6/23 @ 7PM PT: Virtual Happy Hour (SGS Only* | Join the waitlist)
• Wed 6/24 @ 1pm PT : Co-Working Session (SGS Only* | Join the waitlist)
• Thurs 6/25 @ 10am PT: Automate Your Life: Live Build Workshop (SGS Only* | Join the waitlist)
• Fri 6/26 @ 4PM PT: AI Tools Yappy Hour (SGS Only* | Join the waitlist)

* Smart Girl Society is our private community for women who want deeper conversations, accountability, and tools that actually make life easier. Join the waitlist to get in the next round.

 Work Wisdom of the Week:

“Don’t wait to be discovered. Document your impact and ask for the seat.” A mentor told me that early and it reshaped my career: I track measurable outcomes, share concise updates, and propose next steps. That habit took me from Operations Manager to Director.”

Glory V. Bruno (Director of Operations)

 Share your best work wisdom here.

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