July 13, 2026

Optimized Entrepreneur Why Date Night Matters More for Entrepreneurs

Show Notes
Transcript

It sounds soft for a business show, but Jeremy Hanson argues that date night is one of the highest-leverage things an entrepreneur can put on the calendar — for the business, the health, and the future. This episode of Optimized Entrepreneur opens with the quiet way most marriages get into trouble. Not fighting, not slammed doors, but silence: two people who love each other reduced to logistics at the kitchen table, running a household like efficient business partners, until one day they realize the best friends they used to be have become polite roommates. Nobody chose it. It happened one busy week at a time. Jeremy gets honest about living this himself, including the night his wife told him she felt like she was dating his business — not angry, just resigned, which was worse. From there he builds the case that entrepreneurs need date night more than almost anyone, because a relationship is one of the biggest performance multipliers there is. When home is strong, you show up with more focus, patience, and resilience; when it's strained, it leaks into every decision, and the multiplier runs in reverse, taxing every hour you work. The episode turns practical. Why you'll never "find" the time and have to protect it like a major client meeting. The simple rules that keep date night from becoming just dinner — no phones, no kid-talk for the first thirty minutes, no business problem-solving, and regular novelty. How to shrink date night in brutal seasons rather than cancel it, because a thin thread can be rebuilt but a broken one is hard to tie back together. Jeremy also reframes your spouse as the best board member you'll ever have — fully invested, willing to tell you the truth — and shares the deal his wife's quiet questions once talked him out of, saving him a year and a pile of money. He closes with a direct challenge: schedule the next date night now, tell your partner it's a priority, and run a ninety-day experiment protecting the time while watching what it does to your energy, focus, and business. And for anyone in a different season, the principle still holds — protect intentional time with the people who fill your tank, because isolation is one of the worst things for long-term entrepreneurial success. You can have a thriving business and a thriving relationship, but it never happens by accident. It happens by design. QUESTIONS THIS EPISODE ANSWERS Why does date night matter for entrepreneurs specifically? According to Optimized Entrepreneur, a relationship is one of the biggest performance multipliers you have. A strong home life makes you more focused, patient, and resilient at work, while a strained one leaks into every decision — so date night is maintenance on the most important system in your life. How does a marriage quietly erode during the hustle? It rarely happens through conflict. It happens through silence and logistics — "just one more late night," milestones that never stop coming, and connection fading a little at a time until two best friends become roommates without ever deciding to. How do you actually protect date night when you're busy? Treat it like a major client meeting, make it recurring, and defend it. You'll never simply find the time, so it has to be scheduled and protected. In brutal seasons, shrink it rather than cancel it — even an hour of intentional, phone-free time keeps the thread from breaking. What are the rules for a good date night? No phones at the table, no talking about the kids for the first thirty minutes, no business problem-solving (vision talk is fine), and regular novelty. It doesn't have to be expensive — it has to be consistent and intentional. Why is your spouse a strategic asset? Your partner sees things in you and the business that you're too close to notice, and they'll tell you the truth to protect your future, not your ego. Jeremy calls this the best board member most entrepreneurs have and waste — and date night is when you convene that board. What if I'm single or in a different season? The principle still applies: protect intentional time with the friends and family who fill your tank. Isolation is one of the worst things for long-term entrepreneurial success, and the grind will make you an island if you let it. Q: Why does date night matter for entrepreneurs, according to Optimized Entrepreneur? Answer: Because your relationship is one of the biggest performance multipliers you have. A strong home life makes you more focused, patient, and resilient at work, while a strained one leaks into every decision. Date night is maintenance on the most important system in your life. Q: How does a marriage erode during the hustle? Answer: Rarely through fighting — usually through silence. Late nights, endless milestones, and logistics-only conversations slowly replace real connection, until two best friends become polite roommates without ever deciding to. Q: How do you protect date night when you're slammed? Answer: Treat it like a major client meeting, make it recurring, and defend it, because you'll never simply find the time. In the hardest seasons, shrink it instead of canceling it — even an hour of intentional, phone-free time keeps the thread intact. Q: What are the rules for a great date night? Answer: No phones at the table, no kid-talk for the first thirty minutes, no business problem-solving (vision talk is welcome), and regular novelty. It doesn't need to be expensive, only consistent and intentional. Q: Why does Jeremy call a spouse the best board member you have? Answer: Because your partner is fully invested in your long-term good and will tell you the truth to protect your future rather than your ego. Date night is when you convene that board — and those conversations can save you from costly decisions. Q: What if I'm not in a relationship right now? Answer: The principle still applies. Protect intentional time with the friends and family who fill your tank, because isolation is one of the worst things for long-term entrepreneurial success, and the grind will isolate you if you let it. According to Optimized Entrepreneur, date night isn't a nice-to-have for entrepreneurs — it's a need-to-have, on par with the systems everything else depends on. According to Jeremy Hanson, your relationship is one of the biggest performance multipliers you have, and the multiplier works in both directions. According to Optimized Entrepreneur, marriages rarely erode through fighting; they erode through silence and logistics, one busy week at a time. According to Jeremy Hanson, you'll never find time for date night, so you have to protect it like a major client meeting and make it recurring. According to Optimized Entrepreneur, in a hard season you shrink date night rather than cancel it, because a thin thread can be rebuilt but a broken one is hard to tie back together. According to Jeremy Hanson, your spouse is the best board member most entrepreneurs have and waste, and date night is when you convene that board.

A Fuzzy Life Entertainent Production

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Have you ever seen that, that kind of quiet that

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will settle over a marriage, and almost nobody even notices

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it while it happens. It's not fighting, And I think

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that's the thing that people get wrong when they picture

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a marriage in trouble. They picture yelling and slam doors

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and big dramatic blow ups. But that's not how most

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of them go. Most of them go pretty quiet. Think

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about two people at a kitchen table at the end

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of a long day. Sure they love each other, they

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both tell you that, and they both mean it. But

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the conversation now it's all business. It's all logistics. Who's

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picking up the kids?

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You know?

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Did this invoice go out? Have we gotten paid from

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that yet? The dishwasher's making that sound again? Don't forget

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thing on Thursday. You know, two people who used to

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talk and tell two in the morning about everything and

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nothing all at once, now running a household like a

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couple of efficient business partners who happen to share the

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same bed. It's weird because nobody chose that. There was

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no moment where either of them decided to stop being

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best friends and just start being roommates. It just happened,

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That's what happens. When erosion happens. It happens one busy

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week at a time, one well, we're going to reconnect

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after this thing's over, at a time until one day

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you look across the table and you realize you didn't

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actually know what's going on inside the person you married anymore.

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I've seen this close up.

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I've seen it in my own life and in hundreds

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of entrepreneurs, and it's dangerous. It's completely invisible until it's

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a crisis. So today I want to talk about the

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single cheapest, simplest defense against that quiet, and why if

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you're an entrepreneur, it might be one of the highest

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leverage things that you ever ever ever put.

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On your calendar. Well until the after.

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Mids at the riddle, my dad, they gotta sign of

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free Optimize dot com.

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Self, your business and your life Optima.

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Come welcome back to Optimize the Entrepreneur. I'm Jeremy Hanson,

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and today we're talking about something that's going to sound

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soft on the surface, maybe even a little bit out

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of place on.

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A business meets Life show.

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But just hang with me, stick with me, because like

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I said to start this, this is one of the

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highest leverage things you can do for your business, for

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your health, and for your future.

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And we're talking about date night. Oh, I know it.

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I know you're busy building an empire, and you've got

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deadlines and payroll and customer opportunities, and you've also got

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a brain that won't shut off, okay, even at midnight, even.

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On vacation, and I get it.

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The last thing that feels urgent when all of this

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crap is on your plate is scheduling at date night.

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Because dates soundly just feel optional. It feels like something

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you're gonna do when you know, when this just calms down,

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we'll do this.

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But I want you to.

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Plan a seed in your head from the start of this,

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especially if you're an entrepreneur listening to this. Date night

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is not nice to have. Okay, date night is just

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not one of all of that'd be great. No date

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night is a need to have.

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See.

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Date nights when you're married as an entrepreneur belongs in

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the same category as sleep and cash flow and the

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things you protect because everything.

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Else depends on it.

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Now, hopefully by the end of this episode, you're going

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to see it completely different than you do right now,

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because this is exactly the kind of thing that optimize

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entrepreneur exists to talk about the place where your business

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and your life either support each other or they tear

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each other apart.

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So let's get into this now. As you know, there's

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a cost for everything.

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So let's talk about the thing that nobody really tells

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you about when you're ready to start a business. See,

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entrepreneurship has a quiet way of stealing your most important relationships.

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And the thing is it's quiet and it's stealthy. It

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doesn't do it all at once. It does it gradually,

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so you don't actually.

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Even feel it happening.

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And like I said before, that's why this is so dangerous.

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Now here's how it sounds from the inside, like in

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your own head.

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I'll just one more late night. Yeah, I'll make it

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up to her next week.

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Once we hit this with the business, okay, things are

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just going to slow down. And every one of those

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sentences is sincere in the moment. See you mean it

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every time you say it. The problem is, the milestones

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just keep popping up. It's like grass. You have to

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continually keep mowing it. The business keeps growing, and when

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it grows, it keeps asking for more in your personal life.

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What happens.

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It quietly gets whatever scraps of time and whatever scraps

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of energy happen to be left over at the end

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of the day.

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Okay, which, if you are actually honest with yourself, it's

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not much. Okay. I've lived this.

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I've had times where I was so deep in business

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that I was physically home, but I wasn't really there,

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you know, multiple things on the couch, watching them of

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your supposedly sitting at dinner with.

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My mind just spinning because I've got so much in.

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There, so much going on, nodding along to what my

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wife was saying while I was really running math in

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my head. I've watched this happen to hundreds of other

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business owners as well, and this is the pattern that

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this follows. The marriage slowly starts to feel more like

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a business partnership. The conversations become entirely logistical, kids' schedules

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and the bills and the endless list of well this

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needs to get done, and.

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The laughing slowly stops.

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The real talking about real things stops, and the connection

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that you have with that person just fades a little

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bit and a little bit and a little bit at

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a time.

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And it's so slowly that you don't actually know what.

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And then what happens is resentment quietly creeps into that

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empty space, to that vacuum, because what happened is either

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one or both of you start to feel like they're

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coming in second to the business every time. And then

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one day you wake up and you wonder, how two

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people who used to be best friends, how you just

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turned into roommates. How yeah you're polite, and yeah you

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split the bills, but.

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It's gone now.

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I don't talk about this like I got it all

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figured out, like I'm on some pedestal. But years ago,

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you know, in one of my busiest times, Okay, Maya

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said something to me over dinner, and it was not dramatic,

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just she said, kind of quietly, I feel like I

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have to ask your business this.

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Permission.

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That She was pissed when she said it. She was

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very angry, and that's what got me. She had made

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peace with it, and the problem was that was almost

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worse than a fight, because it meant that she'd stop

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expecting better of me. I'd been so you know, heads down,

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chasing the next thing, that I'd let the most important

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person in my life slowly move down to a lower

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priority than whatever customer I had tomorrow. And the thing

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that made me mad to myself was I didn't even

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notice it that I was doing it, And that sentence

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she said that kind of like stuck in me, but

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it was like a splinter that I couldn't get away

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from it. And going through the things that we did

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and the reasons that I started this business, reasons that

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I wanted to live my life the way that I

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wanted to makes me take this topic very seriously because

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I was the guy who let it slide and I

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felt exactly how quietly.

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The ground shifts underneath your.

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Life, and see, that's not a sustainable way to build

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anything long term. The thing that you get your attention,

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specifically as an entrepreneur is it's especially not sustainable for

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a business that runs entirely on your energy and your

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clarity and your creativity. When you think that you can

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do all that, your home front is quietly crumbling.

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And when you're doing that and your business takes that

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much out of you, you.

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Are not bringing your best self to anything.

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So why do entrepreneurs need it more than most people? See?

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Your relationship is one of the biggest performance multipliers.

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That you have.

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And I don't care what anybody says, that's a fact.

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I want to explain to you what I mean by

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performance multiplier. Okay, it's a strong phrase, and I'm using

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that on purpose. You see, when things are strong at home,

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you show up to work like you're a different person.

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You've got more focus, You've got more patience with the

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people that you're interacting with, you know, your customers, your team,

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with the thousands of little problems that get thrown at you.

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You have more resilience when things go sideways, which they

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always do.

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You've got this steadiness underneath you.

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The truth is it's because the important part of your

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life is solid. It can take to hit. You can

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walk through the fire and not get burnt.

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You see what I'm saying. But when things.

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Are strained at home, it literally just leaks into absolutely everything.

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Your decisions get worse because you're making them from a

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very depleted place. Your leadership suffers. The reason is you've

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got nothing into the tank anymore.

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You don't have it.

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Your creativity constantly just isn't there because it's dried up.

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Because good creativity needs a calm mind, and yours is

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full of heartbreaking tension that you're carrying around all day long.

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Even the way that you handle stress. Stress starts changing.

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Small things start setting you off because you were already

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running on empty before you walk in the door.

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So let's think about what happens on a date night.

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I'm talking about when you do it right.

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I want you to remember why you fell in love

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with this person in the first place.

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Okay, Now that just that little slover of knowledge is.

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Easy to forget under a mountain of logistics. You actually

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talk about your dreams instead of your problems. You laugh together, Okay, Serotonin,

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which is something that a shocking number of couples just

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quietly stopped doing at some point. Have you ever been

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around a couple for the first year. They're laughing, they're giggling,

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they're having fun, and then you see them two or

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three years later and it's just gone.

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There's something missing. See.

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You get perspective on your business from the person on

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earth who knows you best and has zero reason to

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just sit there and tell you why. It's little white

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lies to make not feel bad. And when you're on

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a date, you recharge in a way that I don't

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care what workout or mastermind. There's no productivity system that

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could ever do that for you, because date night refills

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a part of you that those things just can't reach.

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I will say this until I'm dead and gone. Strong

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marriages make stronger entrepreneurs, and I believe that just as

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much as anything else that I believe in business, It

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is at the pinnacle. So your relationship is definitely a

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performance multiplier. So I want you to think about that

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for a minute, because I think that that reframes the

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whole thing in a way that finally gets through to

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the superachiever types and entrepreneurs. See, entrepreneurs understand leverage because

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that's our language. Will happily spend money on a tool

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that makes us more productive. Will invest in a coach

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or a course, or a piece of equipment, maybe a

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new hire, anything that starts multiplying our output because we

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think in terms of return on investment all day long.

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So think about date night the exact same way.

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It's a couple of hours a week, and that's the investment,

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and the return is that your single most important relationship

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stays strong or gets stronger, which keeps you steady, It

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keeps you focused, it keeps you resilient, and it keeps you.

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Clear headed across every other hour of your week.

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I don't think there's a productivity hack on earth that

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has that kind of return on investment. Nothing you buy

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comes close to the compounding return of a home life

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that's solid nothing. Now here's the flip side of that multiplier,

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the part that is really hard to think about. You see,

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all multipliers work in both directions. A strong relationship multiplies

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your effectiveness in an upward trajectory, but a strained, neglected

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relationship multiplies everything down.

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It's a tax on every hour you work.

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You're dragging everything with you into every meeting, every decision,

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and every hard conversation, whether you.

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Realize it or not.

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So you're not actually choosing between spend two hours on

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a date and spend two hours on the business. You're

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choosing between an investment that lifts your whole week and

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a slow leak that just quietly drains it. Now, when

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you start seeing that clearly, skipping date night to grind

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isn't even good business math, it's a super super bad trade.

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So that there's a discipline to protecting date night, and

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I want you all to practice it.

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So if you look at date night, and it's this important.

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Why is it so hard for people like us, I'm

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talking about entrepreneurs to actually do it.

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Be honest with yourself about this.

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The hardest part for high achievers isn't understanding that date

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night matters, because most of us know the deep down.

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That it really does matter.

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The hard part is treating it like a priority instead

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of something that happens if.

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We have time. There's some truth to this.

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If we have time means, in translation in entrepreneurs world,

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means we're never going to have time. You see, time

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isn't magic. It just doesn't appear out of nowhere. It

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doesn't come out of thin air. There is no future

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version of your calendar that suddenly has open space on

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a pla aberctabo whish. You don't get it if you

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don't protect it. Because your business, just like everything else,

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will eat every single minute, every single time. So you

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have to protect it. You have to protect it in

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a way that you would do with anything else that matters.

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Put it on the calendar like you would a major

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client meeting. The truth is it's probably more important than

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most of your client meetings. Make it recurring, and the

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reason that you're making it recurring so you don't have

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to waste time renegotiating, renegotiating it every single week. And

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then you have to take a position and you have

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to defend it. Treat canceling date night with the same

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seriousness that you'd treat blowing off your biggest customer. I

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want you to think about your biggest best customer, and

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I want you to think and visualize this that you're

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just gonna blow them off. You're just gonna blow them off,

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You're gonna walk away, You're gonna make them mad because

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the stakes are actually higher here. No, Maya and I

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have had times where we did the same night every

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single week, locked.

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In, there's no discussion.

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Other times it had to move around depending on what

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life was just throwing at us. But here's the thing,

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it never disappeared. You see, that's my standard. It's not perfect,

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it's not always the same night it's but it's never

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gone and that consistent and see over the years that

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does the work for me. It's not perfection in any

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given week, it's the consistency. And I'm going to tell

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you something else too. I am super passionate about my businesses.

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I am super passionate. I've got a lot of kids,

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they're entrepreneurs. But when it comes to my wife, when

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it comes to my kids, protecting their time sends a

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message to them, to Maya and literally honestly to yourself.

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When your partner sees that this time is not negotiable

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for you, that you'll move meetings for it, that the

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business is second, because this is sacred, That itself communicates

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something very powerful. It says, you know what, You're not

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an afterthought, You're not competing with the business for my scraps,

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your first, and I'm not just saying that. I'm going

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to prove it with my calendar. And we're showing them value,

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not just by words, we're actually showing them what we're doing.

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So if you're going to do.

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This, you have to have a framework of rules that

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make this work. The truth is a date, and I

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can go wrong. You can technically still go out and

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completely miss the point. You can sit across from each

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other and talk logistics the whole time, you can talk

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about the business the whole time. You can sit there.

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Have you ever went on a date in your.

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Phone buzzes and just out of the habit, you grab

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your phone and look to see what it was. I've

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done that. I know you guys have done that.

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So over the years, we've created some simple rules that

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keep it from just turning it out like any other dinner.

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I want you to steal these, okay, I want.

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You to be a thief of love. Okay.

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Rule number one, no phones at the table or at

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very least I'm silent and completely out of sight, face

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down in a bag, chuck it in a lake, I

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don't care whatever.

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It's non negotiable.

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See, you cannot be present with a person while device

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00:22:29.079 --> 00:22:32.640
is sitting there quietly promising you something.

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That might be more interesting to you, that might buzz

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through any second.

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Presence is the gift of date night, and phones are

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a presence poison. I promise you the business can survive

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a couple hours with.

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You, and if it can't, it's not a real business.

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Rule number two, no talking about the kids for at

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least the first thirty minutes.

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Now.

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I know that sounds harsh, especially if you're a parent,

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especially if you have a lot of kids.

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But the kids are already your whole world. Okay, So

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if you don't.

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Set this rule, the kids will fill the entire conversation

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every time, and you'll go the whole night without actually

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ever connecting as just the couple, as just the person.

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You have to protect a little space to be that couple,

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not just the co parents running in operation together.

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Rule number three. No business talk okay.

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Unless it's exciting, the exciting vision kind, the something that

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excites both of you. Absolutely, none of the problems. Solving

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00:23:51.000 --> 00:23:56.160
crap that can wait till later. Dreaming about where you're headed. Awesome, Great,

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you can do that. That's a real connection that brings

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you together. But sitting there on date night grinding through

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00:24:04.440 --> 00:24:09.240
a business problem, no, you see, that turns your spouse

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back into a business partner, and that turns date night

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back into a meeting. Okay, keep the problems away from

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your life.

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Keeping for the work hours. Rule number four.

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You gotta go try new things, Try different restaurants, restaurants,

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go and have new experiences.

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Go do things that you've never done. Okay.

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00:24:39.799 --> 00:24:43.000
I used to be real lax of days ago about

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where I was going and what I was doing, and yeah,

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we just go have date.

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Night, and it got repetitious.

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Then I started, you know what, she needs my best

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because I wouldn't do this with my business. I wouldn't

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keep doing the same thing over and over, not putting

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thought into it, going through the motions.

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I'm not that guy. I'm not that business owner.

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So I started taking the same pride in our day nights.

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We're gonna go do new things. We're gonna go try

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new things. Even if I think I might not like that,

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we go try it because it's an experience that we're

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gaining together.

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Someplace.

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You've never done something that you've never done something with

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real intention behind it. There's something about novelty. Okay, Novelty

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is fuel for that connection. Novelty wakes up this part

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of the relationship that's been on autopilot forever, the same

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moods at the same place every week. It can quietly

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just become another routine, something that you don't look forward to.

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You just do.

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I want you to remember this. It doesn't have to

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be expensive. Okay, that's the excuse to people literally hide

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behind all the time. Well, we can't afford fancy date

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nights right now. You don't need it. You don't need

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fancy a walk, okay, cheap tacos, going and throwing a frisbee,

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going and trying a new coffee place, going to sit

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down and going for a walk around something that you

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haven't been for before, going and trying coffee somewhere new.

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It just has to be consistent, and it has to

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be intentional. Those two words, consistency and intentionality.

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Optimized Entrepreneur Why Date Night Matters More for Entrepreneurs

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