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Winners Know When to Quit
I had to call my wife to pick me up yesterday after re-injuring my knee by pushing six miles when my physical therapist said three. Sitting on that corner waiting for her, I realized something uncomfortable: sometimes the hardest thing you need to do is quit. We glorify resilience, grit, and stick-to-itiveness because they work... until they don't. If you've achieved success through raw determination and sheer will like I have, you've been rewarded for pushing through—which makes it even harder to stop when stopping is exactly what you need. I break down why business model problems and product-market fit issues can't be solved with more effort or longer hours, why pushing harder on the wrong problem makes it worse, and how to recognize when your most reliable tool (perseverance) has become a hammer making you see every problem as a nail. This is honestly as much a message to myself as it is to you—for anyone whose feedback loop of "don't quit, push harder" has become so ingrained that knowing when to pause, pivot, or walk away feels impossible.
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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.
About Ray:
→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.
→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.
→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com
→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.
→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com
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Transcript
Yesterday I had to call my wife to come pick me up um on my walk run um because after about six miles or so because I fucked up my knee again by not listening to my physical therapist and pushing further than I should have. And there's a really important like legitimate lesson in here that's you know I'm I wrote and recorded this to to remind myself and so I hope it's it's helpful for somebody else. And you know the the thing is when we things like resilience and patience and grit and stick-to-itiveness like all of those things are are great like we we glorify those things and they're they're strengths in in many many ways. But a lot of times the hardest thing that you need to do is quit right. And we like we associate quitting with giving up. We associate quitting with taking the easy path. We associate quitting with something bad like that's what's hammered into us as a kid or at least me right like what was hammered into me like you don't quit like you got to stick to it you can't quit that sport early because you don't like it you can't do this. And quitting is is the easy road so sticking to it is the good thing and that's the muscle that you need to build. And you know if you've achieved any level of success through like raw determination sheer will work ethic what's happened is it gets actually harder to quit uh beca no even when it's the right thing to do right. It gets it becomes more difficult to slow down to temper to pause to say I can't do something and that is the hard decision that you need to make if your pattern has been I get success through this grit and stick-to-itiveness and not quitting then you've been rewarded over time right like the the rewards the success that you have is a is a function of the stick-to-itiveness and so that's the feedback loop right like that's that's what you've trained into your brain that by doing this th I get what I want like this is the path and when I do this thing good things come from it. And a lot of times that's that's very true right like that's why if you have that muscle that's like why you tend to succeed when other people don't because you're able to see things through you're able to endure the pain you're able to will that shit into happen into happening while other people are going to quit right. And so again that feedback loop gets really like settled in and that is a strength until it's not right until you hit a wall that isn't going to move no matter how long you stick to it until you get a problem that's not going to be solved with more effort or with more mental toughness because you're you're solving the wrong problem. It's like a physical injury right like there's a physical injury or or an illness type of thing that you say hey you know what um I can't I I'm going to prolong this like I'm going to actually make it worse because I'm going to try to like push through this thing right like I I was supposed to go three miles yesterday I went six and guess what fucked up my knee like it's not I'm not going to fix the problem by doing more I'm not going to fix the problem by going longer or going harder I'm going to fix the problem by knowing that at mile three you stop right. Like that's and that to me sometimes that's the hard thing is I want to push harder I want to keep going. The the feedback loop has been good. This happens a lot in business right like if you have a business model problem like a or a or a product market fit problem like two fundamental things in your business that you try to solve by sheer effort by working longer hours by working harder effort isn't going to solve the business model problem it's not going to solve the product market fit problem. The inability to to stop the inability to to pause the inability to zoom out and say I need to quit for a moment and and reassess this is no longer a mental toughness it's now a liability. It's now holding you back right and in the prior data points that I have or that you have that said by doing this I get what I want by doing this I win that's now like it's misleading me right like I'm relying on those data points to keep doing this thing and it's the wrong thing to be doing. And like sometimes that answer is rest dude don't run like or or on the business case like this is when you pivot. This is when you say you know what this isn't working like instead of pushing harder let's pivot instead of choosing to persevere. And the the way that I I I look at this and this message is as obviously as much for myself right as I sit on the corner waiting for my wife to pick me up yesterday and processing this the ability to push on when others don't is a is a strength it's one tool at your disposal. It's one of the many tools you have in the toolbox to draw on to solve the problems that are in front of you and to achieve the goals that you want. But as they say like having a hammer doesn't make everything a nail right. It is just one tool it is not the only tool so use it accordingly. It sounds like I'm talking to you I'm talking to myself like this is legitimately a message and a reminder for myself to use the right tool for the right job at the right time. Hope it helps adios.
