The Line You Draw at 5:00

Every demanding job teaches you the same lesson without ever saying it out loud: if you answer at 6 PM, you'll get asked at 6 PM again.

In this episode of The 5:00 Project, we look at why the line between work and everything else keeps moving on you — even when the job is legitimately urgent, even when you're the kind of person who's good under pressure. That instinct isn't a flaw. It's often exactly why you're trusted with the work you do. The problem is when it runs unsupervised after 5:00.

We break down:

• Why boundaries aren't announced — they're taught, one small yes at a time
• The real, untracked cost of the evenings that quietly disappear
• Why "just set boundaries" is incomplete advice, and what's missing from it
• A simple three-question filter to run before you ever open the laptop back up
• Why protecting your time only works if you know what you're building with it

This isn't about working less for its own sake. It's about making sure the exceptions are chosen — not defaulted into because a phone buzzed and old habit took over.

Transcript

Copy Transcript Copied

SPEAKER_00 0:00

There's a moment I want you to picture. It's 4 58 p.m. You've closed the laptop or you're about to, and your phone lights up. One more email. One more quick question. One more fire that somebody upstream decided was yours to put out. Or it's a colleague who stops by your desk. Hey, I just got one more thing for you. You got a second to talk? And you know that feeling in your chest, that half second where you've got to decide, do I really answer this right now, or do I let it wait until tomorrow? Well, that half second, that's the whole episode today. Because what you do in that half second over and over for years, that's not a small thing. It's the difference between having a life after work and just having work with some sleep in between. I'm going to spend the next half hour or thereabouts talking about that line, where it is, why it keeps moving on you without your permission and how you hold it. Not in theory, but in practice. When the person asking you to cross it out ranks you, needs you, or just doesn't know any better. This is the five o'clock project. Let's get into it. I do defense work part-time, right? So that means when somebody's career or rank, their ability to stay in the army or sometimes pay is on the line, they call me. And here's the thing about that kind of work: it doesn't punch a clock. These separation board hearings don't care that it's Thursday at 5 p.m. and I had plans. Or there's a soldier that just found out they're facing a separation action, guess what? They're not waiting until business hours to panic. They're not waiting for a convenient time to call and say, hey, sir, I need some help. So if you do work like that, whether it's legal work, medical work, or anything, where someone's crisis becomes your entire Tuesday night, you know the line doesn't move because you're lazy or you're undisciplined. It's because the job, well, genuinely and legitimately, sometimes urgently requires it to move. And that can be why it's dangerous. If the job never had any real stakes, protecting your time is easy. Nobody feels guilty ignoring a low priority Teams message at 6 o'clock in the evening, or hard cases were ones that could actually erode your life. Those are the ones where the ask is very, very real. Someone genuinely really needs you. That chain of custody issue, for instance, I do need to nail that down before the hearing later this week, or this memo that I have to prepare for a suspense date really does matter to somebody's career. And here's what I want you to sit with. The legitimacy of the request is not the same question as whether it has to happen right now. Those are two very different things. And for a lot of demanding jobs, you're trained to sort of collapse them into one. If it's important, it better be now. And if it's now, it better be you. And if it's you, it must be tonight at your kitchen table or at your desk at home instead of you being with your family or, God forbid, alone with your own thoughts. It's not a rule, it's a habit that the job or the task is building in you one exception at a time, every time you make it. You have to think about how it happens, though, because it's again not one big decision where you sign a contract and saying, I hereby sacrifice my evenings. Because no one does that. It's a hundred small decisions. It's one late email answered at 9 p.m. just this one time, or some issue at the office that really can't wait, or a boss or a client, a soldier, partner who learns that if they ask you at 6 o'clock, you'll answer at 6 o'clock. And once they learn that, well, why would they ever not ask then? You've just taught them that it's okay. You have then set that rule. And that's the part that nobody tells you. Boundaries aren't something that are truly announced, they're taught and learned and developed through what you actually do, message by message, and I'd even say action by action. If you answer at nine o'clock tonight, you send a very clear, quiet memo to people around you, and it's that this hour is open for business. You can't be surprised when they take you up on that again. So that line doesn't move because your job is unusually demanding. Plenty of jobs are demanding. It moves because sometime along the way, you started teaching people one small yes at a time that it really wasn't a line at all. And ultimately, just from a personal experience, this is just being a victim of one's own expectations at some point. If I want to get ahead, this is what I have to do. Well, really the solution is counterintuitive. If I actually block out time to get this done, I will be more effective. And we'll explore that here in the next couple of segments as we move through. And kind of going off of that, let's talk about cost for a minute. In the legal world and in the financial world, those are two worlds that I experience before five o'clock each day, right? Cost is always recorded. There's some type of cost metric. There's a billable hour, right? For the guard, I keep track of time. I spent 0.5 hours on the phone talking with this client about this issue. Uh I have a case file. There's exhibits. There's a log for everything. Activities for most corporate jobs today are logged, especially if they involve client-facing personnel. You are logging in some type of resource management system in your CRM system that you made a client contact or you did some type of work for the client. It's because those types of things are important for the job that you're doing. And I'm not getting around that. It kind of helps businesses and certain organizations keep track of time spent versus the revenue brought in. It makes sense. But your evenings don't get logged anywhere. Time after five isn't really getting logged anywhere. For a lot of people, it's not. And that's part of the issue. Let's say for a minute, your job asked you to work an extra, let's call it 10 hours a week and put it in writing. Hey, sign here. Now the expectation is you're gonna work 50 hours instead of 40. Well, at least you'd see it. You could negotiate it, you could argue about it, you could decide if it's worth it. But usually that's not how it happens. It happens in 15-minute increments that don't show up anywhere. It's a phone call here, an email thread there, a hey, can you look this over? It turns into 90 minutes gone very, very quickly. And nobody is gonna do the accounting work and add up that time for you. That's gotta fall on us individually. And here's an exercise that was referred to me by someone, and I know I'll be trying it. If you guys are familiar with Cal Newport or with Mike Hyatt, Cal has a time block planner, which I think is fantastic for organization. And Michael Hyatt and his team have the full focus planner, uh, both very, very good uh tools for productivity. Ultimately, they're going to have a spot on your daily tasks where you are going to go through your afternoon or evening routine and check shut down. Make note of that time you shut down. If you don't have a routine, just write down that time you're actually ending work every day. Or at least make note of it somewhere. Do that for seven days. Then look at the pattern. And you might be surprised. And it's not because any single night was bad, but your average is probably going to creep somewhere that you never thought it would. So what is that stolen time? Well, stolen maybe too strong a word. What does that time actually cost you? And it's the part that matters to us, it's the part that matters to people who listen to this podcast, because we're talking about building using that time. It's not some type of abstract work-life balance, although we tend to reduce it to that. It's things we just don't get back. It's a rep at the gym that you're skipped because you're white by eight o'clock. It's, you know, a phone call with my son where you know I'm present in the room, but not in the conversation. Because half my brain is still working on something that I never spun down from. It's a relationship conversation with a spouse or a loved one that needed real attention, and that people who don't control that time with postpone because they're waiting for things to calm down. I'll admit I've been guilty of that one lately. Except things never do calm down because you've never drawn the line that allows it to calm down. And the one that really hits hardest, it's the things that we care about at that stage that don't have a deadline. It can be really important things that we're chasing that don't have a deadline. No one's chasing you about your own estate plan. At least not at my age, people aren't. It's something that I know about and that I actually exercise a lot, right? I mean, I do this sort of thing for a living, but nobody's chasing me down to get one done. Nobody's emailing me at 9 p.m. demanding I sit down and figure out a passive income plan or I don't know, enjoy the house, or other things you've worked so hard for throughout the course of your career. The things with no dreadline are going to lose out to the things that do unless you protect time for them on purpose, and it's gotta come from you. It's not gonna come from anywhere else. And that's that's the cost. I don't want to reduce it just to burnout, but that can happen if you don't do this for long enough. I think we've all been there. The actual cost becomes smaller. And actually it is sneakier, and it you don't realize it until it can be too late. It's that your own priorities are quietly eroded every day to someone else's deadlines. It's not necessarily because their deadlines are more important. Work deadlines are important, but it's because their deadlines have a voice and yours don't. And you've got to give them one. Now, I know what a lot of advice on this topic is going to sound like. Set boundaries, learn to say no, and protect your time. And that is true, but it's a little bit incomplete. And incomplete advice can make you feel like a failure if it doesn't work. Here's the problem. Advice assumes that all that friction is external.

unknown 13:05

Right?

SPEAKER_00 13:06

The only thing kind of standing between you and that protected evening is the audacity for you to say no to someone important, a boss, a client. And yeah, maybe. To a point, right? It could be hard to say no to somebody who has some power or authority over you or who might complain if you say no. But if you do really serious high-stakes work, it's not just that. There's a lot of internal friction too. It's the way that we're trained. If you're a high performer by training and by action, we're someone who's good in a crisis. That's not incidental. It's why we're trusted to do what we do. And people who fold under pressure don't handle difficult things where people's lives or livelihoods or future can be on the line. So when something urgent lands at an inconvenient time, the instinct that we have to jump on that type of task, I don't think it's tantamount to weakness, but it is an instinct that makes us good at what we do. It's hard to switch it off. And oftentimes we don't want to do that because that instinct is such an asset before 5 p.m. The problem is if we let that program that makes us so good at what we do before 5 o'clock run unsupervised after 5, if that mental routine keeps running. If I can handle this now because I must handle this now every time, with no distinction between an actual emergency and a preference for speed, it can be a recipe for disaster over the long term. So the advice is often reduced to simple phrases such as stop caring so much or tough it up and say no. You have to build a filter. You have to build different approaches that we actually use in the moment and as part of our routines, not just in theory. I know that's where I struggle. The first thing I did when I had these types of competing interests as an inexperienced trust officer, you know, in a faster-paced environment in the bank where you're dealing with very wealthy people who are demanding your time and you're managing their assets. So I stuck with an Eisenhower matrix, and I've brought this up in meetings, I don't know how many times. So it was very counterproductive. But an Eisenhower matrix can be a great way for you to determine priorities. So you get a sheet of paper, I tend to turn a piece of notebook paper on its side here in a landscape format, draw a rectangle, and then divide it into four quadrants. On one axis, you have urgency, and on the other axis, you have importance. So for instance, let's draw it up as if the top left-hand corner, that first quadrant, is important and urgent. Those are the things you handle and you handle immediately, because they can't wait, and they are important. The top right can be important, but not so urgent. Right? So those are things that really are important. I think of this as maybe like development plan items or maybe other things on the five o'clock project that I have, like this podcast for too long, where yeah, I do want to get to them, but I have other pressing matters that have to come first. So unfortunately, those do get delayed, but they do get done. And then if you go to the bottom corner, the bottom two quadrants, if you go to that bottom left, I usually mark that as urgent but not important. I tend to delegate those things to somebody else who can handle it. This is great with the advent of AI. This is great with having uh someone working underneath you. So if you have an associate, if you have an analyst, somebody you can delegate things to, or an AI agent that you can have it running a subroutine on, that could be something that fits that square. And then the final one, not important, not urgent, delete. If it's not important and you don't have to get it done right now anyway, it does it really require your attention at all. I just think it's something that worked for me. I hope it would work for you guys too, and it works with so many different areas of your life, whether that's professional tasks that need to be completed from nine to five, or during your own projects later on in the day with the time that you have to yourself. I think that's an important thing to distinguish. What is important and what you need to do right now versus, yeah, this is important, but it can wait, and things that just aren't important at all. The other thing we need to do is to create some type of filter. So within that half second, if you're within it, you have a decision-making matrix. The Eisenhower matrix is going to work before you ever get there. So you can immediately classify this by using the filter, right? In this situation, within this half second where you have to make a decision, you can place it in that quadrant real quickly. First question Is there going to be real harm if this waits until tomorrow? I'm not talking about a mere inconvenience, not someone's mild irritation. I mean actual harm. You're gonna lose a lot of revenue. There's a case that's gonna go south. A person's not gonna get the help they absolutely need right now to avoid something catastrophic. There's a deadline that is genuinely immovable, and those can do occur. There's a lot of things in our daily lives that fail this test. Now, an ER doctor that has somebody come straight in that needs urgent attention or they might die on the table, yeah, you're probably gonna take care of that. That's a pretty genuine, immovable deadline. It's now but a lot of things do fail that test. A lot of things are urgent because someone else procrastinated. And if everything is urgent to those people, nothing's going to be urgent. And it's not because the world ends if you wait 12 hours, it's because somebody didn't prepare. All right, secondly. If this does, if this does pass the first test, does it really require me specifically right now, tonight, to do this? Or does it just require a response, letting somebody know that I've seen this and I've got the ball, and I can give a shorter response and really finish the real work tomorrow? Oftentimes, especially in client-facing professions, somebody just wants to know that the issue has been seen and is being worked on. About 80% of the time. Maybe more than that. So if you just say, hey, I got this, I'll have it to you by the end of the day tomorrow, you just saved yourself a 90-minute session at the end of the day. If I do this tonight, what does it teach the person asking? And I said this before, every yes is a lesson to someone asking you to do something at an inconvenient time. If the answer to that question is it teaches them that this is always available, then we're incurring these costs that we've talked about. Their deadlines matter and ours do not. Or at least we're not giving ours that voice that's necessary. You're not holding the line. So you have to run those questions pretty quickly in your head before you even reopen your laptop. Most times, the honest answers that you're giving yourself from that filter is permission to close off and move on. And some nights they don't, and that's fine because you're choosing to work with your eyes open instead of reacting because someone stopped by your desk or a notification lit up your screen or your phone. And that's the difference between a boundary and a discipline. So the boundary is the line that we draw, the discipline. Is the action behind that and the filter we run every single time? And one of those survives contact with the commanding, with a demanding job. Command is a demanding job. Certainly advised a few commanders. Moving on, here's something else that I kind of noticed in myself and a lot of people I'm talking to. If we're protecting time, but we don't know what it's really for. So let's say you're protecting white space. We just tend to fill it in with something else. That's almost as draining as work. It could be doom scrolling, you're half watching something on TV, just being tired somewhere else. That's not really winning. You're just shuffling the exhaustion around. And I've been guilty of this quite recently. So the second half of this isn't just guard the time, it's know what you're going to do with that time. And it means a few specific things for me. I'm just going to be as honest as I can about it because I think specifics can be far more useful than generalization. So for me, it's something that I'm working towards being home ownership. I know in this economy, it's not just the idea of having the house, but the sense of something that's actually mine that I've earned over time. Nobody can take that away from me because I'm busy. It's something different about working you do on your own home versus work you do for somebody else. One depletes you, and the other, even though it's tiring you out, fills you back up. I think that's worth protecting time for. The other thing could be building something on the side, maybe using what you already know how to do. Not necessarily a job that's recreating the same pressure with a different name, but things that can compound templates, processes, relationships, someone in your network who trusts your judgment on something specific. So in my case, that's estate planning. It's where an hour tonight can still work for me next year. Right? It's also part of building your pathway forward for your professional life. Or maybe it's helping you build something for a passion project that you can turn into your job later on. It's an important thing to keep in mind. It's instead of just evaporating everything when you send an email about those types of things, it's just something you continue to work for. I'm not saying these things because I think your version has to look like mine, because it's not going to. I think you know what yours is, but it's the thing you keep saying you're going to get to once things calm down. It's a project that has no deadline and then can't win the fight against the things that do. For me, that was starting the five o'clock project. I did it right now. I set up set aside time to record an intro episode and this episode here. And this was the result. Crazy what happens when we set aside the time. Another thing that we'll talk about with that is fitness. You've got to set the time aside for it to make sure you're taking care of yourself. And fitness can look like so many different things for so many different people. It just depends upon what you're most comfortable with. It doesn't have to be something that you're going to work so hard at that you're going to absolutely cook yourself for the next day. Far from it. You just need something to keep coming back to. That can be going for an evening walk to start, something you genuinely enjoy that helps you move and keep your body moving and helps your mind stay active. Could be reading a book as part of your routine. Anyway, I say all that to say this. Treat your own priorities as if they have that same deadline pressure as someone else's requests. It's not urgent in the way that demanding jobs can have things that are urgent, because it's really not. But if you never treat them like they matter on a clock, they constantly lose to things that do by default. And it may mean you literally block it out on your calendar. Not eh, someday I'll start that podcast. No, Tuesday, 6 30 to 8 o'clock. Put it out there. Give it the same respect you'd give something like a client meeting. Because if it's not on the calendar, it's not competing for your time. It's just hoping you'll get to it eventually. You're just hoping you'll get to it eventually. And I'll also say this. The stuff you build in protected time, it doesn't sit next to your career. It can become things that give you leverage in your career and in life, depending upon what you pick. It can be a financial cushion, an alternate path. It can be a reason you don't have to say yes to these 6 to 9 p.m. emails out of fear or out of trying to get ahead. Protecting your other hours and building your future are not separate goals. One makes the other sustainable long term. Instead of just a discipline you have to white knuckle through all the time. That's something I'm still learning to do. And it takes time and effort on both sides. I'll give you an example. Lately, as caseloads on the military side increase, people are demanding my time during my nine to five job. In some cases, it is warranted because I know some people who are working are working full-time as military lawyers, and it's really the only time I can reasonably speak to them. But that's the exception, not the rule. A client calling me out of fear at, say, 11 a.m. on a Monday when I'm in a team meeting is not going to get my attention because that's not what I'm sitting in that meeting for. Simple as that. I've had to build boundaries on both. Likewise, if I'm working on something for a client outside of my working hours after 5 o'clock, as part of one of my 5 o'clock projects, you can always have multiples. My nine to five job doesn't get my time. That laptop stays closed until 9 o'clock the following morning. Or eight o'clock the following morning, depending upon when I get in. So the practical part is you have to actually hold this line. I don't want to just close off with something that's merely inspirational. It needs to be more concrete, logistical. Because good intentions don't survive this kind of hard week without a structure underneath it. Pick your actual cutoff, make it specific. Not I'll try to log off earlier than, you know, six. No, pick a time. For me, if my kids are at home with the babysitter over the summer when they're not in school, I make note of what time it takes for me to get back here by five o'clock. That's the time I log off. Every day. Every day I'm in the office. Without fail. Whatever's real for you. Don't be vague about it. Specifics give you something to notice if you've crossed the line. Two, if someone does come up to you, you got to use that three question filter before we engage. Not after. Again, real harm if it waits. Does it really need me right now? And what if saying yes? What if I say yes and it teaches somebody else something that I don't want them to know? Or what does it teach them if I say yes? Excuse me. 90% of that time that filter is going to give you your time back before you've ever lost it. When something does pass the filter, this is number three now. If something does pass the filter and it genuinely needs you, commit to a time that you're going to give it. Time box it. Out loud, even if it's just to you. This gets 30 minutes, then I'm done. Emergencies expand if you don't put a wall around them. Fourth, protect that thing you're building the same way you'd protect a client meeting or an obligation. Put it on your calendar with a name at a specific time. If it's abstract, it loses. If it's scheduled, it's got a chance. Five, and this might be the hardest one. You have to accept that some nights the answer really is yes. Work wins and it's not a failure. I'm going to say that again. Sometimes the answer's got to be yes. Work wins, and it's not a failure of discipline. The goal for this was never to have zero exceptions, it's just to minimize the exceptions. They're chosen exceptions, being aware of the exceptions, using whatever filter that we need at that time, like the five, excuse me, the questions that we've said before. This is number five. We just don't want to default back into a reaction behavior because your phone buzzed or somebody walked over and you're right back into an old habit. I mean, that's really the whole episode, if I'm being honest. So that line at five o'clock was never really about the clock, right? It's about who's making the decision in that half second where someone wants you to give more of your time up. And that person is you on purpose, or the notification can do it for you on autopilot, reacting in that old habit. So tonight, whatever tonight is for you, when that message comes in, right as you're about to close that laptop, walk away, go do something else, I want you to pause, ask those three questions to run that filter, and then decide on purpose instead of just reacting. That's it. We're not trying to do nothing after five o'clock, though sometimes it sure feels good to do nothing after five o'clock. Just let it be yours on purpose, far more often than not. Anyway, I am so glad you guys decided to spend this time with me. I'm glad that we're building all these things together. This is the Five O'Clock Project. I'll see you guys in the next episode.