Shownotes
I used to think that successful entrepreneurs had a "secret map" that gave them 100% certainty before they made a move. I spent years in planning mode, working my tail off but making zero progress because I was terrified of making the "wrong" bet.
In this episode, I’m sharing a raw look at a trap I see so many founders fall into: the endless pivot. I recently worked with a business owner who cycled through three different strategies in a month, not because he lacked talent, but because he was waiting for a feeling of certainty that simply doesn’t exist in business.
I’ve learned the hard way that our job isn't to find something that works—it’s to commit to making it work. We’re going to talk about escaping the "amygdala hijack," why most results live on the other side of a J-curve, and how to start thinking in probabilities rather than absolutes. If you feel like you’re rowing hard but staying in the same place, it’s time to stop looking for a guarantee and start making a bet.
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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.
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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Transcripts
You aren't looking for the thing that works, you're committing to making it work. And if you don't get that distinction, as I didn't for a long time, you'll stay stuck in planning mode forever, working your ass off, making zero progress and and again, I'm saying this because I experienced it, I lived it.
Now by the way, if you like reading this stuff and actually applying it, that's what the newsletter is for. You can hop in at https://www.google.com/search?q=rays-email.com for free.
So I was working with this this MSP business owner who was being driven mad by uncertainty is the is the best way that I can frame it. And I because I really mean just like it was driving him crazy. And you know we started with with him you know wanting a sales audit. You know, he's like, "You know I'm not sure what our our bottlenecks are, what the constraints are, I you know I'd love for you to to take a look and kind of build out a roadmap and figure out what the you know what the next six months or so looks like." I said "Cool. All right." So we we get agreement and we're ready to go. And then last minute he changes his mind. Like, "Ah, I'm not ready for that yet."
So okay, cool. We almost immediately afterwards are like, "Hey you know what? I want to hire an SDR. I want somebody like local that can they can do some canvassing, they can go down to local events, they can also be making some calls." So we start marching down that road, helping him with some recruiting. Changes directions again. "Nah Ray, that's that's I think that's too expensive. I just don't know if it's going to work. You know, I I can do some of the events in the interim. I'd rather hire somebody abroad."
We do recruiting, right? At MSP Sales Partners, so we start sourcing talent and we're sending over like really good candidates because we we screen with sales management experience. Like that's what we do, it's what I've done my whole life, it's what my team's done. So we're sending over good candidates and he's like "Yeah you know these are really good, I just I just need to see more. I just need to see more candidates. I just I'm just not sure, I'm I'm not sure who to pick." And so okay, cool, so we get him more candidates. And then he he puts them through this like very very extensive like process. At like multiple personality tests and multiple interviews, the whole nine yards. All trying to eliminate uncertainty.
And we get down to the offer stage and he's like, "Well I'm not sure if I like both of them. So I mean like should I hire one, should I hire two?" And we we have that conversation. Then it's, "Okay well you know like hey I I like both of them, uh but I want to negotiate on pay. I want to pay a couple hundred dollars less per month." And actually, you know what? It's offer day. Like we got to send them an offer. We've had all the conversations. "Actually I don't I actually don't know if this is going to work. Like I'm not ready for this. I I don't know if the SDR strategy is what we want to do. We're thinking about growing through acquisition this year and not necessarily you know going to get our own clients. Like we want to buy some businesses so I'm not sure if this is aligned."
And this was the pattern, like over and over. Now I'm not saying this to be critical. I'm saying this because I recognize this behavior very well. I've lived it. Like this is a past version of me.
And here's what I learned: the source of all of this comes down to looking for certainty instead of accepting that as business owners, as CEOs and entrepreneurs, we simply operate in uncertainty.
Right, like it's just it's just what we do. We don't find certainty, we make it. That is the job. We we make bets. We don't we don't think in terms of right and wrong and hey if this is a this is the wrong decision it's fucking over, right? Like we think in terms of uncertainty and probabilities. I feel 70, 75 percent sure this is going to work out. Never 100 percent. But like that's the job I chose. And that's why we get paid the way we do, or or don't, like unfortunately.
But when you refuse to accept that, when you keep looking for certainty, like thinking that you're just going to find it, thinking that you're going to stumble across it, like it fucking drives you crazy because you start operating from your amygdala. Right, like the reptile part of your brain and it's impulsive. It's like panic-driven, it's fight or flight.
And here's what happens when you combine that with the bias for action that that's required to be an entrepreneur: you end up changing all of the time because you're taking that fight or flight mode but you're constantly staying in motion because we have this bias for action and you're just you're pivoting constantly. We're going to go this direction. No, we're going to go this direction. Actually, this direction. I'm not sure about that direction.
And there's two fundamental problems with this. Like first is, all of the big results in business happen down the road. And almost everything in business has an exponential curve on it. You know you think about an employee's productivity or a marketing strategy or a sales process. It's it's got this exponential curve. The early part is the hard part because you're figuring things out, right? But you but if you stick with it, if you learn how to do it, if you get through what Seth Godin calls "the dip," if you get in the reps and you build the right systems, get the right people in, get the right plays done, the results come later and they and they form a J-curve.
But if you're constantly changing directions, you never actually get to experience that. The second problem is, and this is the sneaky part, when you're constantly pivoting it keeps you in planning mode. And planning mode is the safe space, right? Because it feels safe to be building. It feels safe to be thinking, to be planning. But when it comes time to execute, like that's when the uncertainty actually kicks in, right? And and that's when it starts to feel unsafe. So you go, "You know, maybe we need to change directions now."
Like we've done all of this stuff. So take this example: all of the interviewing, all of the recruiting, all of the comp discussions, all of the one or two hires, all like everything that you can imagine, then when it gets down to like pulling the trigger, "Ah I don't know now. Like now I'm going to back out."
And you stay in that safe space of planning or you hit execution mode which is hard, right? Going back to the first problem, it's the hard part, and then you bail before the results show up. And either way you never actually get the outcome that you want.
So here's what I've learned like for myself in dealing with this. First, accept that uncertainty is simply part of our job description. Right, as CEOs we operate in that 55 percent to 85 percent confidence range. Like if because if it's if it's higher than 85 percent, 95 percent, like we're not really making like strong, bold decisions at that point, right? Like it's more like, "Yeah I feel pretty good about this. Let me weigh the returns."
Annie Duke actually has a really good book um called "Thinking in Bets." You know, the poker player and it's a really solid way to to think about decisions in general and and not necessarily think is this the right move or the wrong move. It's like, "Is it a good bet or a bad bet?"
Right, it's not "Oh my god if it's the wrong move like something catastrophic is going to happen here like it's the fucking end of the business." You know, like you're not you're not in fight or flight mode. It's like, "Nah I feel 80 percent about this one. That's good enough. It's a smart bet because we don't we don't have the luxury of 100 percent." And as soon as we accept that, it helps us get out of the amygdala part of our brain into the calmer, more strategic part of the brain where the bias for action isn't actually as dangerous.
Second thing that I've learned is that sometimes you've just got to slow the fuck down and clarify what the strategy is. You know, I hear like a lot of entrepreneurs like the old Facebook like move fast and break things. Yeah, that's great, but not if you don't have a North Star on where you guys are going. If everyone knows what the primary target is then yeah moving fast and breaking things is great. You're all moving in generally the same direction. You're rowing in the same direction. Awesome.
But if the strategy isn't really clear and everyone's rowing in different fucking directions and everyone's just running around in the business isn't making a lot of progress, you've got a ton of activity, a ton of effort, a lot of motion, and no real progress. And and sometimes the answer, and this is it's harder than it sounds, but it's the answer is you just got to slow down.
Like calm the bias for action for just a second, clarify what the strategy is because one of my mentors like hammered this to me probably because going through this exact same thing that I'm telling you about is: like tactics follow strategy. And if you're if you're really unclear on what tactic you're supposed to be using, like if you're constantly confused and there's a lack of clarity, a ton of uncertainty, a lot of times that's a symptom that you just don't have a clear strategy underneath.
And the third thing is, once you commit to a plan or commit to a strategy or commit to a tactic, then fucking commit, right? Like accept that you're going to have to make it work. Like very few things in business, well at least like anything that's worthwhile, very few of them come easy. Every business strategy is hard. Most tactics that are that are that are worthwhile are hard.
There's things to learn, there's things to iterate, and I have found very few of them that work very quickly and very well, or at least not sustainably, right? Like very hacks that might might go away overnight or something like that. But like you're not looking for the thing that works, you're committing to making it work. Because like I promise you if you don't have that mindset nothing is going to work.
You'll constantly be changing directions, you're going to invest a ton of time, a ton of money, a ton of effort and and you don't make progress. It was more like, "Hey you know we're going to go this direction. Ah it's a little hard. Like that one that one feels a little unsafe. I'm not quite certain on that one. Okay, we're going to go over here instead. Nah, actually, we're going to go over here." Like when you commit, fucking commit, because like I said like none of them are easy.
And the things that are easy usually aren't worth a shit candidly. So I don't say this critically. I say this passionately because I honest to god I've lived it. I've experienced it and I have gone through it so many times that these lessons are what I can see it in other people so easily and I almost I can almost feel like sympathy. Like feel how that person's feeling and know that I had to go through it enough times to learn these lessons.
So if you find yourself really frustrated, like working really hard if you're not making progress, I really genuinely hope that this message resonates. I hope I hope you hear what I'm saying and I I sincerely hope that it helps. Adios.
