Sales Hustle is now Sales Transformation
June 28, 2021

Episode #112 Mindfulness for Sales with Jordan Benjamin

Joining Collin Mitchell in this episode of the Sales Hustle Podcast is Jordan Benjamin. Let’s hear from Jordan as he delves into mental health and mindfulness and why this is very important to sales folks.

Jordan Benjamin is the Founder of My Core OS. My Core OS is built to help you update your personal/corporate operating system to drive peak performance and harmony between work and life. We work with companies and specialize in working with sales teams to help drive a growth mindset and open the doors for more effective learning and growth for your team.

Jordan is also the host of the Peak Performance Selling Podcast where they interview top sellers and sales leaders on how they play the mental game to show up at their best every day. You can listen to the podcast at

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Episode 112 - Jordan Benjamin

Welcome to the sales hustle. The only no BS podcast, where we bring you the real raw uncut experiences from sales makers across various industries. The only place where you can get what you're looking for. Uh, your sales game today's episode is brought to you by sales cast sales cast helps sales professionals transform the relationship building process and win their dream clients.

[00:00:30] I'm your host, Colin. All right, sales hustlers. Welcome to another episode. I've got a great guest and we have an awesome topic for all the sales hustlers. Today. I'm going to be speaking with Jordan Benjamin. He's the principal founder, man, uh, manager over at my core O S uh, he's very passionate about mental health mindfulness for sales evangelists, and that's what we're going to be talking about today.

[00:00:54] So Jordan, welcome to sales. Excited to be here. Yeah. Awesome man. And we were just having a lot of fun. We've gotten to know each other, uh, quite a bit recently here. Uh, and before we jump in, you know, we're going to talk about, you know, selling mindset, mindfulness, why it's important to sellers, things that you love talking about.

[00:01:13] But before we jump into those things, there, just give us the short version of yourself. Yeah, I stumbled into sales, uh, after working retail at Lulu lemon, uh, out of college had a business degree and from there got into startup world, uh, did the BDR a hundred dials a day, marking them down on a note pad, maybe being successful once out of those a hundred times.

[00:01:39] Startup failed, went to another one, got laid off again twice within about six months, uh, jumped over to HubSpot before they went public and have been coaching their agency partners on how they grow their businesses and selling quite a bit, uh, for quite a few years now, uh, before I really kind of realized there was a huge opportunity.

[00:01:59] Gap in my sales training, uh, that was all about the tactic. All of my managers, all my leaders said, Hey, dial the phone more and never got into the core motivation of why am I not dialing the phone more? What am I afraid to fail on? So that led me to start my CoreOS and my peak performance selling podcast to ultimately help sellers think about the attitude, the mindset, the mental health that needs to be sustained to really be blatant and sustain a long-term career in sales as a salesperson.

[00:02:27] Yeah. Wow. All right. So thanks so much. I'm gonna, I'm gonna dig into a couple of things there. Um, Lulu lemon, huh? Not a bad gig. It was fantastic. I was in Boulder, but one of the cool things that I never realized until I reflected on it is they had us actually write out our one, three five-year goals. Yeah, post them up inside of the store early on.

[00:02:47] So not only did that get me into a bunch of free yoga classes. Uh, it was just a fantastic place to work and got me a bunch of bunch of clothes that, uh, are just normally obscenely expensive that were only mildly expensive for me as it. Yeah. Yeah. But the interesting thing there, right. Is, is, is that experience, you're not selling yoga pants, right?

[00:03:08] You're selling people feeling good about themselves, right. Because they feel good when they wear those types of clothes that make them look fantastic. Yeah. We, we were actually called educators versus associates or sales reps, and they also. You know, used language really intentionally that got me into this concept of neuro-linguistic programming and our goals.

[00:03:31] It wasn't a due date or internal items. It was a by windy opposed to having a deadline with like, oh, dead. But like that's kind of scary and intimidating. So they, you really set an early foundation in me to really think about how I approach the world quite a bit differently. I didn't really realize at the time, but it's totally stuck in how I approach the world now.

[00:03:52] And what's really helped me be pretty successful in a lot of the roles that I've gone into. Yeah. Yeah. So then, so then you started out in, in BDR SDR roles in. Sounded like you weren't having a lot of success right now in the little, you know, I would imagine they had some fancier tech than chicken scratch on a, on a, on a notepad for seeing how many dials you did today.

[00:04:16] No, and we were, you know, we were venture back company, uh, by Google ventures, but you know, everybody's selling this kind of unique model of pay-per-click marketing. We're like, oh yeah, we're trying to. People are like your Prada. Yeah. Please like Google and vet your Google. Yeah. Google, please just take my phone.

[00:04:37] Call a startup live with zero brand recognition, kind of Kylie competitive space. When you talk about pay-per-click marketing, uh, it is something that a lot of people. Get calls for every day saying, Hey, we can do it better and cheaper for you. So there was a lot of competition going into it and we did have a really unique model.

[00:04:59] We got that company up to about a hundred employees, but then. It went down to about 10 and has since folded, uh, from that perspective, but it was great learning experience. So much fun, a lot of opportunity to grow and learn in the SDR role and the account executive role there closing, you know, pretty good sized deals.

[00:05:18] Working with companies large and small was a really fun learning opportunity where we didn't have a lot of structure or anything of the store. It was a blast. Uh, well, so, so tell me. When did you get so passionate about mindfulness and, and, and you know, why mindset is, is so essential to, to, to sellers?

[00:05:40] Yeah. So I got into meditation and yoga. My freshman year of college, I had a girlfriend that was like, you gotta come try this yoga thing. And I was an athletic guy who. Like, that's definitely not for me. That's like, ah, it's too soft. I'm not into it. And yeah, I think that's, I think most guys feel that same way.

[00:06:01] They're like, it's super common. We're pretty stubborn too. Absolutely. I she'd been pressing me to go to yoga for years. And finally I came back after spending a little time in California for college and it's like, all right, maybe I'll try this thing. And the end of that class, I laid down in the final Shavasana pose.

[00:06:21] Yeah. Just felt an energy coursing through my body that I'd never felt that I've never touched before. That gave me this first insight of maybe there's more than I've been taught in school about one possible. And I had a friend, so that freshman year of college that shared some different meditation, CDs with me that got me to a point of feeling my brain operating in a different way than I'd ever felt.

[00:06:47] That operate feeling. Or even not feeling my body. And so I just got on this path early on in my freshman year of college that opened my mind to what more could there be than the answers in the textbook in school. And then as I got into sales, I'd continued on with that meditation practice. I'd gone to this conference called wisdom 2.0 a bunch of years, where there were a lot of leaders from LinkedIn and Google and.

[00:07:15] Major major tech companies talking about how do they bring mindfulness into business and leadership. And then some of these major meditation practitioners like Jack Kornfeld, Sharon Salzberg, John Robinson, that all started talking about how so many bleeders in tech companies, especially that they'd been working with in San Francisco and around the world, actually practice mindfulness and use that as a way to balance their.

[00:07:40] And use that as a way as a leader to help their teams show up and move away from trying to juggle work and life all the time to actually bring harmony or integration between the two. So it doesn't just have to be this balancing act. And so that's really been a 12, 13 year journey for me into really seeing a lot of sellers struggle mentally.

[00:08:04] A lot of colors struggle with that concept of buoyancy that Daniel pink talks about bouncing back from getting told no from coming off of your worst sales month ever, and really quick. If you actually come back and do it again. So that's, what's led me at HubSpot as a yoga teacher, as a mindfulness practitioner, leading different meditations, doing goal setting workshops.

[00:08:25] I've done so much around my own personal development in Seth. Godin's all MBA talking about how the school system is broken and really needing to see these foundational learnings that most of us don't get in school around. How do we operate our best and how do we actually understand ourselves first?

[00:08:43] So we can show up for ourselves and show up for others and really create our own best personal operating system intentionally versus the hamster wheel that most of us were kind of conditioned to run on in our school system. At least here in the United States. Man. There's so many good things in there.

[00:08:59] Like I know I'm going to miss some of the nuggets, so I apologize in advance to all of the sales hustlers, because I just, I mean, all of those, you know, we were talking before, I think we got on this mindfulness meditation journey somewhat around the same time. And all those people that you mentioned are people that I have a ton of respect for and, and follow.

[00:09:19] And, um, and so, uh, I'm just. Curious now, um, to try to tie this in right is, is, is because I know that a lot in, in, like you said, you know, a lot of sellers have this stress and, you know, bouncing back from a bad month or, or even just the, the opposite of having a great month and then starting back at zero, right.

[00:09:40] Um, in, in, in these emotional ups and downs and stress and pressure, um, that are still in a lot of sales environments and culture, um, That makes sales really hard. And, and, and you talked about integration, right? So integrating people, so many people view their personal and their professional life as these separate silos, right.

[00:10:04] Or, or in, in, in integration is what really needs to happen. And, you know, when you take better care of yourself, personally, whatever that looks like, uh, you know, sleeping well, eating, healthy yoga, exercise meditation. You exceed professionally in a way that you didn't think is possible. So there's so many good things in there.

[00:10:31] I know I missed some of them, but I want to ask this question to you. What have you seen either? For yourself or for people that you've worked with that have started to adopt some of these, you know, things that we're talking about it by investing in themselves personally. And how has it helped them professionally?

[00:10:49] Yeah. So some of the folks that I work with, one of the first exercises we like to do. Really working to understand what are the key areas that they value in their life. What are the areas that are most important to them? Because we all have different things that we value at different times, you know, and really setting the tone of understanding that that may change for us next week.

[00:11:09] Next month, next year, as things evolve, you know, it was COVID has come up. A lot of people have had to reevaluate. What do they value? You know, maybe they valued going out to the bars or going to live music, which I still love. And miss completely granted I'm really pumped. I just bought some tickets to go see some shows.

[00:11:24] Uh, but we've had to really evaluate, like, what are those key things in our life? You know, I think most people as you go through a school system, you think about, okay, I need a job. I need the house with the white picket fence and all of these areas that we haven't really taken time to sit back and say, well, what is really empowering?

[00:11:42] Maybe it's family, maybe it's money. Maybe it's my career and understanding where are those things like, where do I actually stand today? Because so many of us, if we're going to drive a new place, we're going to open up Google maps. It's going to say, yeah, here's where my location is today. And here's where I want to go.

[00:12:00] But most of us don't live our lives that way. And so we really work to evaluate and understand where am I at in my life today? How am I doing? How do I actually maybe quantify that. One to 10 scale and then how do I start seeing, well, where is it that I want to go from here? So that's one of the exercises that I love to do, but the first thing that as I run different new hire trainings and work with folks.

[00:12:21] Yeah. Understanding do we have a growth mindset? And do folks understand that you can grow and develop? You know, again, you hear me beat up our traditional school system, which I think is just so outdated in how it trains us to be our best versions of ourselves as humans, because technology and computers are fantastic, but we are.

[00:12:42] Computers, we are not infinite scalable machines, but we can interact in their face with those things really well. So once we can understand that we can grow, we can develop that just because we got an F on some tests in high school, doesn't mean that we're always going to be a failure at whatever that subject is, because we have the ability to use our brain power to put in time and effort.

[00:13:02] So I love working with folks on first getting into Carol Dweck's growth mindset, and then from there moving into, okay, how do we understand. Where do we want to grow? Where do we find that richness in our lives? And then we can start to align our career, our financial priorities, our family, and all those other areas of life that are really important to a whole life.

[00:13:25] As we show up, uh, in a really rich. Yeah. So a couple of things there, I love, um, love that you brought up growth mindset. Right? So, and I love that you said too, is that, you know, knowing like where do you want to go? That's that's, that's great. And a lot of people maybe can figure that part out. Right. But then you mentioned like it changed.

[00:13:50] Things come up and it changes. And I think so many leaders sometimes don't do that constant. Check-in like, Hey, is this still the runway? Right? Or even just individually, this is where I said, I want to go. And then I'm still just trucking along on that hamster wheel or on that treadmill, trying to get there, trying to get there.

[00:14:08] And I haven't even really checked in with myself to figure out like, Hey, wait a minute, wait a second. Is that where I still want to go? Oh, no, these things have changed. That's no longer as important to me as I maybe thought it was, or actually prefer to go somewhere else, maybe. Um, totally. And so being, you know, being intentional and being mindful and, and having a practice where you have that relationship with yourself to be able to check in and, and be in touch with like, That felt great six months ago, not so great now.

[00:14:39] Um, and, and be able to change the course. Right. So, so I think that's a really important piece in, and then you mentioned, you know, uh, you, you gave a great example there of getting an F on a test and then feeling like, oh my gosh, I'm going to be a failure forever. And with a growth mindset, you're like, oh, okay.

[00:14:56] I got it now. This is fantastic. I know the things that I now need to work on. This is great. I'm now aware of the things that I can be better at that I need to work on that I need. And even more so. Do I care to be better at those things, maybe not work on it, you know? And that's the part where I think the mindfulness is so powerful of being able to just sit with yourself or walk or whatever that may be to get in touch with yourself and say, well, what are the thoughts coming up?

[00:15:27] How do I check in with myself to say, does this feel right for me now or not? And just giving yourself some quiet time and space to process, I think is so powerful because. The technology that we have buzzing dinging, giving us alerts. Everything is fighting for our attention aside from ourselves. And so if we can find even maybe it's one minute, five or six deep breaths to just slow down and see, how am I feeling today?

[00:15:58] What, what feels good for me here? You know, does it feel right? It gives us this power to really step into our own best version of ourselves. Again, I never gotten school or really in many other places until I started dealing with my own stress or anxiety and started searching it out on my own. Yeah. And I think sometimes, you know, maybe.

[00:16:21] People are looking for like, you know, an experience like you had on the yoga mat here, where you're like, wow, this is what I've been missing out on to really understand like, okay, this is worth the energy that I'm going to have to, you know, the energy output to get these sort of results. Cause it also can like, feel like a lot of work if you're not getting it.

[00:16:42] The experiences that maybe you're hoping for, but then going into it with an expectation, um, can, can make it not a successful activity as well. So it's really important to like go into it with an open mind, and you're not going to sit for five minutes and, and feel fantastic and stress free and be Mr. Or Mrs.

[00:16:59] Zen. Like it just doesn't work like that. It's, it's a constant practice sometimes. You're good at it. Sometimes you're not, um, yeah. The, the practice it's like that is not every day is going to be fantastic. That's what I got. That's what I learned in my yoga teacher training classes was it's a practice and it's not about what the person next to you is.

[00:17:22] It's about, what's good for you. And I think that was where I started thinking about sales and my entire life is this concept of a practice versus a perfect and you know, folks that I've talked to, uh, I'd love the mantra progress over perfection. And how do you know you're, you're moving forward every day.

[00:17:38] How do you realize I'm getting some imposter syndrome, which means, oh, great. I'm actually pushing myself and challenging myself to get into that growth mindset and any time it's chattering in the background, uh, it's. A good thing to know that you're challenging yourself, but taking that deep breath, being able to just touch it, touch base with yourself and check in is where now all of a sudden you create that space to move away from this fight or flight mentality.

[00:18:05] That's served us all. That's why we're alive. It's kept us alive for tens of thousands of years, but in today's technological age like that doesn't necessarily serve us. The vast majority of the time in the decisions we have to make, especially as sellers sales leaders, managers, uh, w it's not life or death.

[00:18:25] If we take 30 seconds to take a deep breath or two, before I move into my next one-on-one, or before I move into that next call, where yet we're always trying to slam things back to back to back to back to back. And we find through neuroscience through all sorts of different studies and SMRI that our brain doesn't perform that well.

[00:18:42] After about 80 to 90 minutes of focus. And so what do we do to actually create those systems that make it easy for us to operate at our best and to sustain it? Because I don't think anybody in sales just wants to have one good quarter or one good year. It's something that we want to be able to do for a long time, uh, and grow as our careers continue to develop and we learn new stuff.

[00:19:06] Yeah. Yeah. And I love the point you made there, right. Is, is like, if you're feeling a certain way, having the ability to check in on yourself and that's kind of the big that's, that's the thing here, right. Is by having a practice, then you can start to change your relationship with these things that come up.

[00:19:22] Yeah. Your mind is going to become a little quieter, but it's not going to shut up. It's not going to shut up. It's not going to turn off. It's not going to like, oh, I made a tasty today. Everything is fantastic. And, and yeah, and it doesn't even have to be like, uh, you know, you can be mindful in a lot of things.

[00:19:39] And I think that's a common, a very common misconception is like, you know, uh, Mindfulness is meditation and that's it. Right? Or like the, like in yoga people think like, oh yeah, I'm doing yoga when I'm on my mat. Well, what are you doing? And how are you practicing off your mat? Right. So mindfulness is a lifestyle.

[00:19:58] Right. And you can be ma you can mindfully eat. You can mindfully walk, you can mindfully cold call. You can apply it to anything. If you're just being very intentional about that activity and not, you know, being distracted by, you know, the thousands of notifications from slack and LinkedIn, and anything else that you might have on your computer.

[00:20:20] Yes, it's, that's one of the things that so many people come to me. I think I can't turn my mind off, so I can't meditate. And that is the actual practice. That is the actual workout of finding that space in the breadth of walking up to the door handle and being fully present in the room. To twist the knob to do your pre-call research, looking at somebody's LinkedIn profile to take a minute to say, I'm going to shut off my notifications and fully show up in my one-on-one with my rep or my team.

[00:20:55] Those are the ways that we can bring this into our life. That again are not conditioned in us in most of the ways that we operate. You know, you think about looking at young kids today that are already so distracted with technology, and it's amazing what they can do. But it also shows you this programming that's in our minds and in our brain of great, I'm always looking at 500 different things.

[00:21:18] Even young kids, seeing their parents. Constantly on their phones, distracted, driving, whatever it might be focusing on so many different things. And Cal Newport talks about deep work, and I just got a chance to listen to him, speak, and there's so much evidence behind. If we can really show up fully and present in each moment, we're going to be happier and we're going to do better at whatever task that is that we work on.

[00:21:44] And so for me, I think that is. This concept of mindfulness. Yes. You get a great practice by taking a sit for 5, 10, 20 minutes, whatever feels good for you. But then taking that off of the mat, the bench, the cushion is really where that comes in to help you have this much more fulfilling, robust and rich life that goes beyond just, oh, I can only meditate when I'm sitting on the cushion.

[00:22:13] Yeah. Yeah. I mean, it gives you this, this level full of awareness where you can be more present in any activity and be more aware when things crop up. Right. So I think that there's, there's so many benefits. I mean, we can talk on and on, on forever. Right. But like the bottom line is, is, is sales is a really stressful role.

[00:22:34] Right? And, and, and mindfulness is, is proven, you know, Tons of different studies, right? That, that, that, uh, that a consistent practice is going to really help decrease anxiety, you know, negative, um, you know, talk, um, and really just, you know, have a more, uh, emotional balance. Right. I mean, and there's probably a lot more benefits that you could add too, but where can a seller.

[00:23:01] Get started if they're like, oh, this all sounds great, but it also sounds overwhelming and I'm not sure where to start. How do I take some action? Yeah. There are a ton of fantastic different apps. You can check out. Uh, I'm a big fan. I'm a big fan of the insight timer app. You can find different talks from different folks, uh, anything along the lines there, uh, 10% happier.

[00:23:27] I know we were touching on that. That you're a big fan of, I also, I'm starting to run some different meditation sessions, uh, for sellers for totally free, uh, anybody that wants to check them out, find me on LinkedIn or send me the I'm happy to share when I'm running the next session. And there are endless amounts of books.

[00:23:46] YouTube talks. Google it you're going to find something. But the simplest thing that I tell folks to do is just see if you can sit and take six deep breaths in and out, not focus on anything else. And it doesn't have to be more complicated than that. Maybe you go longer, maybe you go shorter, but the best part about mindfulness and practicing it.

[00:24:08] The second you notice your mind has wandered off, which it's going to, as you didn't simply begin again. And that's the practice and that's the beauty of it. It doesn't have to be a 10 day retreat going, living with monks somewhere around the world. It can be just this really simple, just notice the inhale and the exhale that typically happens subconsciously for us.

[00:24:30] Yeah. Yeah, those are all great. One of my favorite guided meditations on the 10% happier app is it's like a three minute meditation and it's by Dan Harris himself. And it's proof that I don't suck or something like that. I think that's what it's called. Um, and it's just such a simple. Uh, example of like, Hey, anybody can do this.

[00:24:52] And this is like a really comfortable place to start. Um, so I love this, you know, Jordan, thanks so much for coming on today. Uh, really, really appreciate it. Love this topic. Uh, where can people find out more and follow you and see what you're up to? Yeah, the best place is to check out the peak performance selling podcast.

[00:25:12] I am interviewing all sorts of different sellers sales leaders on the mental side of this. How do they think about it? What do they focus on? How do we help support more D and I, and belonging in sales as well, which I think actually being a little bit more mindful is a huge, huge help to helping us build a much more diverse, inclusive and supportive environment in sales.

[00:25:35] So check me out peak performance selling podcast, where wherever you get it, uh, today you'll, you'll find us on Spotify, apple, anywhere you want it. Awesome. And we'll share the link there. Sales hustlers to, uh, to Jordan show so you can check it out. Uh, if you enjoy today's episode, please, please write us a review.

[00:25:54] Share the show with your friends and as always we're listening for your feet. Thank you for tuning in to this episode of sales hustle. Are you a sales profession? Looking to take your sales career to the next level. If the answer is yes, then I want you to go over to sales,, check us out. And if you feel that you are ready, set up a time to talk with me and my co-founder Chris, I'm your host column Mitchell.

[00:26:22] And if you enjoyed this episode, feel free to leave us a review and share the podcast with your friends.