I lost thirty days of Claude Code sessions last week. Just gone. No warning email, no “your files are about to disappear” notification, nothing. I was sitting there looking for a conversation I’d been having with the AI about restructuring my side project’s architecture, and it vanished like it never existed. That’s when I realized what was happening-and honestly, I’m still annoyed about it.

Why This Keeps Coming Up

Most of us GenXers learned to build things by saving obsessively. Floppy disk. External hard drive. Cloud backup. We know the world doesn’t preserve your work unless you force it to. But somewhere along the way, we started trusting that digital platforms would just keep our stuff, and Claude Code let us believe that without any real warning.

The thing is, it’s not malicious. Claude Code has a built-in cleanup timer that automatically deletes inactive sessions after thirty days. That’s the actual policy, sitting there in the settings nobody reads. I’m guessing Anthropic did this for server management and cost reasons, which is fine, but they buried the detail in a way that caught a lot of people off guard. Including me.

And here’s the kicker-when I started asking around in the AI builder communities, I found out I wasn’t alone. This was happening to people constantly, and most of them had no idea why their sessions were disappearing.

What I Actually Found Out

Once I got over being annoyed, I actually dug into the Claude Code settings and found the culprit: a value called `cleanupPeriodDays` that’s set to 30 by default. That’s it. That’s the timer. Your sessions are on borrowed time unless you change it.

The fix took me about two minutes. I went into the settings, located that variable, and bumped it up to 365. You could go higher if you wanted-I’ve seen people set it to 730 for two years or just make it something ridiculous. The point is, you have control over this, but you have to actually do it. It doesn’t happen automatically.

Once I fixed that, I realized I still needed a better system. Thirty days of recovered sessions is one thing, but if I’m going to keep doing AI-assisted work, I need my thinking documented somewhere it actually sticks around. So I started using Claude to auto-summarize the important conversations and push them into a GitHub repo. Now my project thinking lives somewhere permanent-somewhere I can actually find it later when I need to remember why I made a decision.

What You Can Do With This Today

First, go into your Claude Code settings right now and change that `cleanupPeriodDays` value. Set it to something reasonable-at least 365 if you’re doing actual work. This buys you time and gives you breathing room while you figure out a better long-term system.

Second, if you’ve got sessions you care about, grab them before they disappear. Don’t assume they’ll still be there in three weeks. Download them, screenshot them, copy the text-whatever makes sense for your workflow.

Third, and this is the smarter play, start thinking about where your AI-assisted work is actually supposed to live. For me, it’s a combination of GitHub repos and Notion. For you, it might be different. But the key insight is that you can’t rely on Claude Code’s session history as your permanent archive. It was never designed to be that.

This is the kind of thing that feels obvious once someone tells you, but nobody puts it in the welcome email. We’re still figuring out how to live with AI as a professional tool, and that means figuring out stuff like data retention on our own.

Take the two minutes. Change that setting. Your future self-the one who actually needs to remember that conversation-will thank you.

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My brain has felt like 47 open browser tabs since about 2003. Work stuff, kid schedules, aging parents calling about their medications, my side hustle, health appointments I keep forgetting, money spreadsheets I started and abandoned. I’d write things on my phone, lose them, write them again. Sound familiar? Last month I stopped fighting it and threw everything into Notion AI. Four minutes later, I had an actual system. No spreadsheet purgatory. No more pretending I remember when my mom’s cardiologist appointment is.

Why This Keeps Coming Up

We’re the generation that remembers having actual filing cabinets. Then we got email and lost everything digital. Now we’ve got notes apps, reminders, calendar invites, project management tools, and still can’t find anything when we need it. The problem isn’t the tools-it’s that we’re trying to keep everything in our heads or scattered across six different apps.

GenX especially feels this. We didn’t grow up digital native. We adapted. But we also never really developed a system because everything kept changing. One day it’s a Palm Pilot, next it’s Google Calendar, now it’s Discord. Meanwhile, your actual life is getting more complicated. You’ve got work, maybe kids or grandkids, parents who need more help, your side gig, health stuff nobody tells you about at fifty.

The real issue is that you need one place where everything talks to everything else. Your doctor’s visit actually connects to your follow-up questions, which connect to the medications, which somehow ties into your health goals. Your side gig projects connect to your income tracking. Your parents’ stuff is separate but accessible when you need it. That’s not a filing system-that’s an operating system for your life.

What I Actually Found Out

I started simple. I opened Notion, made a blank page, and literally dumped a month of scattered notes into it. Grocery lists, doctor visit notes, project ideas for my freelance work, stuff my mom asked me to remember, fitness tracking I started and stopped, financial goals. Just brain dump. A complete mess.

Then I used Notion AI to organize it. Took about four minutes. It created a dashboard that actually made sense. It pulled my medical stuff into one database, flagged all the follow-ups I’d written but forgotten about, organized my side gig projects by deadline, and created a separate tracker for my parents’ appointments and medications. It even suggested a weekly review template so I’d actually use the damn thing.

The medical piece alone was worth the entire experiment. I typed in my doctor visit notes-messy, scattered thoughts exactly as I remembered them. Notion AI extracted every prescription, every follow-up question I’d meant to ask but forgot, every test result, every next step. It built a clean summary I could send to my actual doctor. I’ve never had that before. Usually I just hope I remember to mention things.

What got me was how it connected things. My side gig invoices automatically linked to a revenue tracker, which linked to a broader financial goals section. My parents’ appointments showed up on a shared family calendar view. My health stuff had a dashboard that showed my medications, doctor visits, and fitness goals all in one place. It’s not that any individual piece is revolutionary. It’s that everything talks to everything else now.

What You Can Do With This Today

Start where I started. Open Notion (it’s free). Make a blank page. Dump everything that’s cluttering your brain into it. Don’t organize. Just write. Your doctor visits, your work projects, your parents’ needs, your side gig, your health stuff, your money situation. Give yourself fifteen minutes. Don’t think about structure.

Then copy that mess into Notion AI and ask it to organize your life. Tell it you’re fifty-something and juggling multiple responsibilities. Ask it to build you a dashboard. It’ll create databases, templates, summaries. You’ll get something functional in minutes. Is it perfect? No. But it’s better than what you had, and it’s actually there when you need it.

The whole point is this: you don’t have to be the system anymore. AI can be your second brain. One place. Everything in it. That’s not lazy-that’s smart.

Talk soon.

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We grew up with no internet, no cell phones, and somehow ran paper routes with more efficiency than our current inbox. Now I spend half my morning copying data between apps like it’s 1987. That stops today.

Why This Keeps Coming Up

Every GenX entrepreneur I talk to has the same problem. We’ve got five or six apps running our business-a contact form, a CRM, email, Slack, maybe a spreadsheet or two-and nothing talks to each other. So you’re manually entering the same data everywhere, reading the same emails twice, and wondering why you’re not getting rich if automation is supposed to be such a thing by now. I realized I was spending at least two hours a day on pure busywork, the kind of stuff a teenager in 2026 would find laughable.

The worst part? I knew the technology existed to stop this. I just didn’t know where to start without hiring someone or spending months learning to code.

What I Actually Found Out

Zapier is basically a middleman that connects apps and runs simple workflows when something happens. You don’t write code. You set up a trigger-”when a new lead comes through my contact form”-and then tell Zapier what to do next. The game-changer for me was adding AI into those workflows. Instead of just moving data around, I could have AI do something useful with it first.

Here’s the setup I’m running now. A new lead comes through my website form, which triggers a Zapier workflow. Before that lead gets near my CRM, an AI step reads all the information and scores it based on how qualified they are. It also pulls out the key details and writes a one-sentence summary so I’m not reading through their whole message. Then it drops everything-lead data, AI score, summary-straight into my CRM with no human hands touching it. I literally never see the junk leads.

Email triage was the other big one. I set Zapier to watch my inbox for new emails, run them through an AI classifier that reads the content and figures out what type of message it is-quote request, support issue, complaint, junk-and then move it to the right folder automatically. Ninety percent of my email routing now happens without me ever clicking on it. The AI even adds a label so I can see at a glance what I’m dealing with.

The part that really blew my mind? Setting this up took maybe four hours total, mostly because I was overthinking it. The actual complexity level is closer to “make a pizza online” than “learn to code.”

What You Can Do With This Today

Start small. Don’t try to automate your entire business on day one. Pick one workflow that wastes your time and focus there. For most of us, it’s either lead management or email. If you’re taking manual notes on every new customer inquiry, that’s your starting point.

Sign up for Zapier, create your first zap with just a trigger and one AI step, and test it before you go wild. I used OpenAI’s API integrated into Zapier, which is straightforward enough. The cost is maybe ten to twenty bucks a month depending on how many zaps you’re running, and most of that is the AI processing, not Zapier itself.

Once you see it working once, you’ll start spotting other places where AI can jump in. It’s like your brain finally realizes what’s possible. Next thing you know, you’re not managing routine customer triage, you’re not hunting through emails, and you’ve got maybe three hours of your day back.

That’s real money, by the way. Three hours a day is a thousand hours a year. Even if you just bill at thirty bucks an hour, you’re looking at thirty grand in productive time you just freed up. And that’s not counting the fact that you’ll probably make fewer mistakes when machines are doing the sorting.

Look, we didn’t have options when we were climbing the career ladder. Now we do, and the tools are cheap enough that there’s no excuse for staying stuck. If I figured this out at fifty, anyone can.

Talk soon.

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Remember when Google felt like a superpower? Now it’s twelve ads, five SEO spam sites, and you still don’t have your answer. I’ve been there – spend twenty minutes digging through garbage when I just need one solid answer. Last month I got frustrated enough to try something different, and I landed on Perplexity AI. It’s not hype. It’s genuinely changed how I research everything from AI tools to market trends to just understanding why my side hustle isn’t working.

Why This Keeps Coming Up

Google’s been dying for a while now, and we all know it. The search results aren’t worse because Google got dumb – they’re worse because the incentives changed. Everyone’s optimizing for clicks, not answers. Reddit threads are now polluted with AI-generated spam. News sites have fourteen popups before you see the article. And Google itself has become a slot machine for whoever paid for the top spot.

I noticed I was spending more time filtering noise than actually learning. That’s when it hit me that I was still using a tool built for 1999 in a 2025 internet. Perplexity works completely differently. Instead of handing you a list of links and making you do the archaeology, it reads multiple sources in real time and synthesizes an actual answer for you. You get the information and the sources right there, no excavation required.

What I Actually Found Out

Perplexity feels like having a research assistant who actually reads stuff instead of just bookmarking it. I asked it “What are the best AI tools for writing product descriptions for e-commerce?” and got back a thoughtful breakdown of four tools, how they compare, pricing, and links to each one. Five minutes. Google would’ve taken twenty, and I’d still be wondering if I missed something better.

The interface is stupid simple. You type a question like you’re texting a friend. “Should I learn Python or JavaScript for building AI side projects?” You get back a real answer with reasoning, not a list of articles that *might* address your question if you read through all ten of them. It’s conversational. It’s immediate. It actually answers the question you asked instead of making you rephrase it four times.

What surprised me most was the sources. Every claim gets cited. You can click through and verify anything you don’t trust. I can actually see where the information came from instead of wondering if that article is just someone’s opinion. For someone building a side hustle or learning new skills, that’s the difference between making informed decisions and wasting money on tools that sounded good.

What You Can Do With This Today

If you’re researching tools, markets, or skills for a side project, Perplexity saves you hours every month. I use it for comparing software – “Which Shopify alternative is best for dropshipping under $50 per month?” – and actually getting a usable answer instead of landing on a review site that just wants affiliate commissions. You can use it for market research, competitive analysis, learning new skills, understanding how something works.

The free version is solid. The paid version gets you more queries and a Pro search that goes deeper. I pay for Pro because my time is worth more than the subscription fee, but I spent two weeks on the free tier before upgrading just to make sure it was real.

Here’s what matters: you’re not learning new search syntax or trying to game algorithms. You’re just asking questions and getting answers. No more four-year-old articles ranking above current information. No more wondering if you’re being manipulated by SEO tricks or paid placements.

I’ve rebuilt a big chunk of how I research since starting with Perplexity. It’s faster, cleaner, and I actually trust the information more because I can see where it’s coming from. If you’re past the point of being impressed by shiny stuff and you just want your answers back, this is worth your time to try.

Give it a week. You’ll get it.

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We survived rotary phones and card catalogs. We mastered fax machines, learned to forward emails with the “FW: FW: FW:” chains, and somehow made it through the AOL dial-up era without losing our minds. But somewhere along the way, email stopped being a tool and became a job. I’m sitting here with 300 emails in my inbox right now, and I’d bet you’re in the same boat. The guilt is real too – like you’re supposed to have some magical system where everything gets read, replied to, and filed before lunch.

Why This Keeps Coming Up

Look, I ignored this problem for way too long. I told myself I was “staying connected” and “responsive” when really I was just spinning my wheels. Every morning I’d open Gmail and feel that immediate dread. The noise-to-signal ratio has become absolutely insane. Most of what lands in your inbox doesn’t matter, but your brain can’t tell the difference fast enough anymore. So you read everything, or you feel like you’re missing something important, and neither option is sustainable.

The old GenX move was to develop a system – color coding, folders, rules, filters. I had all of that. I was organized as hell. Didn’t matter. The volume just kept growing and my time kept shrinking. That’s when I realized the problem wasn’t organization. It was that I was still the bottleneck. I was still the one doing the triage, and I was still the one drafting fifty half-assed replies a day.

What I Actually Found Out

About three weeks ago I decided to actually mess around with AI and email automation instead of just thinking about it. I set up a system using ChatGPT and some basic Gmail automation, and I’m not exaggerating when I say this took about twenty minutes. The setup was embarrassingly simple, which is probably why I procrastinated for six months.

Here’s what happens now: emails come in and get sorted by AI into categories based on what I actually told it matters to me. Client stuff floats to the top. Newsletters and automated notifications get bundled and deprioritized. Then for certain categories – things like follow-ups or common requests – AI drafts replies in my voice. It’s not perfect, but it’s usually about eighty percent there. I spend maybe two minutes tweaking and then I send it.

The thing I was most worried about was sounding like a robot. That’s the whole reason I stayed hands-off for so long. But here’s what I discovered: keeping control of the final send button actually solves that problem completely. The AI does the grunt work. I do the judgment calls. It’s a partnership, not a replacement. And my actual response time has gotten faster because I’m not dragging my feet on the stupid stuff anymore.

What You Can Do With This Today

If you want to try this without getting lost in technical documentation, start small. Pick one category of email that drives you crazy. For me it was client confirmations and meeting reschedules. Tell ChatGPT exactly what those emails look like and ask it to draft a response template. Then use Gmail’s built-in automation to flag those incoming messages and let AI handle the first draft.

The learning curve isn’t steep. You’re just teaching a tool to recognize patterns and handle repetition. The time investment is measured in minutes, not hours. And if it goes wrong? You delete it and try again. Nobody’s getting hurt here.

The real win isn’t that I’m checking email less. It’s that when I do check it, I’m actually looking at stuff that deserves my attention. I’m not wasting mental energy on the noise anymore. That’s the part that changes things.

We figured out a lot of stuff on our own when we had to. Sometimes I think we’ve gotten used to suffering through bad systems just because that’s how it’s always been. Turns out you can push back on that. Set it up, test it, adjust it. Your inbox will thank you.

-Jim

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Look, I know what you’re thinking. TikTok Shop. Another algorithm casino where you have to dance, lip-sync, or pretend to be 24. Hard pass. But here’s the thing I figured out after actually trying this: you don’t have to be any of those people to make real money on TikTok Shop. GenX already won at figuring out technology nobody understood. We built our own computers. We kept Windows 95 running on sheer spite and stubbornness. We pioneered file-sharing networks that scared the entire music industry. This is easier than that. Way easier.

Why This Keeps Coming Up

Everyone’s suddenly talking about TikTok Shop because the algorithm finally caught on that people don’t want entertainment-they want to buy stuff. For years, TikTok was pure content chaos. Now it’s a store. The creator economy people made a bunch of money telling you that you need a personal brand and a ring light and a content calendar. That’s true if you want to be famous. It’s not true if you want to sell products. Those are different games. I kept seeing people my age getting frustrated because they have actual products worth selling, but they thought TikTok Shop required being someone they’re not. It doesn’t.

What I Actually Found Out

The stack I’m using right now is stupid simple. I list products in TikTok Seller Center-same interface, same tools, nothing weird. Then I use ChatGPT to write video scripts. Thirty seconds, one hook, one call-to-action. No performance required. Then CapCut’s AI takes a product photo or URL and generates an actual video. Lights, angles, text overlays, transitions. You give it the product image and your script, and it builds the video for you. No camera. No filming. No editing skills.

The magic part is that CapCut’s AI actually understands product videos. It’s not making abstract art. It’s showing your product from angles that work, adding text at moments that matter, and timing everything to hooks that actually convert. I uploaded a product photo yesterday and got a 47-second video that looked like it took hours. It took me eleven minutes.

What You Can Do With This Today

First, pick a product category you actually know something about. Doesn’t have to be complicated. Tools, home stuff, outdoor gear, kitchen equipment-anything physical. You don’t manufacture it. You find suppliers through Alibaba or local wholesalers, order samples, and verify they’re actually good. That’s the real work, and it’s the same work you’d do offline.

Next, set up a TikTok Seller Center account. It takes about an hour. Add your products with real photos and honest descriptions. This is where you actually think like a business person instead of a performer.

Then write three to five video scripts using ChatGPT. Simple prompts like “Write a 30-second hook for a titanium bottle opener” or “Create a script that shows why this storage box solves a common problem.” ChatGPT spits out copy that actually works. Takes fifteen minutes per product.

Finally, feed those scripts and product photos into CapCut’s AI video generator. The AI builds videos that look professional. Share them to TikTok. That’s it. You’re running a storefront without being a performer. Without being an influencer. Without any of the nonsense that kept us away from this platform in the first place.

I’m making enough that I can actually see it becoming a second income stream. More importantly, I’m selling products I believe in without pretending to be someone I’m not. That’s the GenX win right there. We figured out the internet once already. This is just the next level of figuring it out without playing games. You’ve got this.

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Look, I wasn’t expecting to be the guy talking about AI side hustles at 50. But here we are. GenX got screwed out of a lot of things – pensions, job security, a housing market that made sense. So when something like AI shows up and actually makes making extra money easier, I figured I’d pay attention. The weird part? Nobody’s really talking about how accessible this is for people like us. We’ve got the work ethic, the skepticism, and honestly, the time flexibility our kids don’t have. AI isn’t some sci-fi thing anymore. It’s sitting in your laptop right now, just waiting for you to use it.

Why This Keeps Coming Up

I started noticing it a few months back. Every conversation about making extra income had someone mentioning AI in it. At first I thought it was hype, the usual internet noise. But then I realized something: the people actually making money with AI weren’t the 22-year-old crypto guys. They were people my age who got tired of one income stream and decided to build a second one. A woman in my neighborhood started using AI to write SEO content for local businesses. A buddy of mine automated his entire freelance invoicing process. These weren’t tech geniuses. They were just GenXers who said, “You know what, let me actually figure this out.”

The thing nobody tells you is that AI tools have gotten stupidly simple. Not even a year ago, using these things required coding knowledge or at least comfort with weird interfaces. Now? It’s basically just talking to a smart assistant. That changes everything when you’re considering a side hustle.

What I Actually Found Out

I started testing tools myself, partly because I’m curious, partly because my main business needed help. Microsoft Copilot is the first thing you should touch. It’s built into Office already, so you’re not learning something new for the sake of it. I use it constantly now to draft emails, to summarize meeting notes when I’m too tired to focus, to brainstorm copy for projects. It’s free. That alone makes it worth five minutes of your time to understand what it can do.

Then there’s Claude AI. I know everybody talks about ChatGPT, but Claude actually writes better. It sounds more human. Less like a robot. That matters when you’re writing anything that’s going to represent you or your business. I use it literally every working day. I can prompt it once and get back something I can actually use without heavy editing.

The real game-changer though is Zapier AI. This is the one that freed up actual hours. It connects all your tools together and automates the repetitive stuff. You set it up once – and I mean literally once – and then it just handles the boring work forever. I had been spending like five hours a month on data entry between different platforms. Now Zapier handles it. That’s five hours I can actually bill or spend on something that matters.

What You Can Do With This Today

Here’s the honest version: you don’t need a big plan. You just need to start somewhere. Pick one of these tools and spend an hour with it. Just one. Kick the tires. See what it actually does instead of reading about what it supposedly does.

Most of us GenXers are decent writers or organizers or project managers. AI is a tool that amplifies that. You write better emails faster. You organize information better. You automate the garbage work. Those are skills that directly translate to freelance work, side businesses, or just making your main job way less exhausting. Some people I know have built entire content businesses on the back of these tools. Others have just used them to take on more freelance work without actually working more.

The income part isn’t automatic. You still have to sell something, still have to actually do the work. But the tools make it so you’re not wasting energy on the stupid stuff anymore.

I’m finding new tools every week and I keep a running list. If you want to actually see the full setup – what I’m actually using, how I have it configured – I put that all together in a guide. Link’s in the bio if you want it. But start with what you’ve got. That Copilot sitting in your Office apps right now? That’s genuinely where I started too.

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Look, nobody in our generation got the memo about AI making actual money. We grew up thinking side hustles meant flipping stuff on eBay or selling Amway to your neighbors. Then suddenly it’s 2024 and people my age are making real cash using tools that were science fiction five years ago. The wild part? You probably already have access to most of them.

Why This Keeps Coming Up

Here’s the thing about being GenX-we’re skeptical by nature. We didn’t grow up with participation trophies, so when something sounds too good to be true, we smell it immediately. But this isn’t hype. I’ve spent the last eighteen months actually using these tools, and they’re quietly changing how people our age make money on the side. The barrier to entry is basically zero. No college degree required. No startup capital. Just time and willingness to figure out something new.

I think what’s really happening is that AI democratized skills we used to need specialists for. You don’t need to hire a copywriter anymore. You don’t need to learn complex automation software. The tools are dumb-simple now, and they work.

What I Actually Found Out

First up-Microsoft Copilot. This one kills me because it’s already sitting in your Office apps and most people don’t even know it exists. I use it to draft client emails, summarize meeting notes, and turn rough ideas into actual documents. It’s free, it’s already integrated into everything you’re probably using, and it saves me maybe three to four hours a week. No learning curve. You just start talking to it like it’s a coworker.

Second-Claude AI. I switched from ChatGPT because Claude is genuinely better at writing work. Long-form stuff, client proposals, even editing. I use it every single day in my business now. The reasoning is sharper. It makes fewer weird mistakes. For anyone doing any kind of writing-adjacent work-and let’s be honest, most side hustles involve some writing-Claude is the move.

Third-Zapier AI. This one’s for when you’re ready to actually stop doing boring stuff. Zapier connects all your apps together and automates the repetitive tasks that kill your productivity. Set it up once, and it just runs forever in the background. You could automate email follow-ups, data entry, customer notifications-whatever’s eating your time. The AI part just makes the setup faster and smarter than the old way.

What You Can Do With This Today

The actual side hustles? They’re not complicated. You can start freelance writing or email copywriting tomorrow using Claude. People pay decent money for someone who can write clear, direct marketing emails. You can offer virtual assistant services-basically running someone’s inbox and calendar using Copilot to draft responses. You can create content-blog posts, LinkedIn stuff, email newsletters-way faster using AI, then sell that service to small business owners who don’t have the time.

I’ve also seen people build entire digital product businesses around AI. They’re using Claude to brainstorm and draft course content, then selling those courses for two hundred to five hundred bucks each. No inventory. No shipping. Just knowledge that AI helped them organize and package nicely.

The money’s real. I know a guy our age making twelve grand a month writing email copy for e-commerce companies. He’s working maybe twenty hours a week. He wouldn’t be doing this without Claude and Zapier.

The hardest part isn’t learning the tools-it’s actually starting. GenX paralysis. We want to understand everything before we touch it. But with these tools, you learn by doing. Spend a weekend playing with Copilot. Draft some emails. See what happens. Then decide if you want to push further.

I’m finding new AI tools and side hustle angles every week at this point. If you want my full setup guide and the exact tools I’m actually using in my business, link’s in the bio. We’re at a moment where our generation can actually catch up and get ahead. Nobody handed us the rulebook for this one, but at least we’ve got each other figuring it out.

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