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  • Writer's pictureShirley Owens

Dream As Big As Possible with Jay Rooke

"Entrepreneurship is a game; be playful in it. No one's getting out of this journey alive; don’t be so serious.” -Jay Rooke

Knowing what you want, and figuring out how to get it are two different things. So how do you get what you want? Shirley’s conversation with business coach, Jay Rooke is not only entertaining, but a real look into making your entrepreneurial journey successful. Jay and Shirley talk about how to be an implementer when you’re a visionary and how to go from the corporate world to living your entrepreneurial dream. They discuss the importance of and the positive role that failure brings to success, along with living your dreams and passions. If you’re wanting to break free from the corporate merry-go-round, or just want to develop yourself personally, you won’t want to miss this episode!


01:31 Finding Happiness on a Soul Level

05:11 Your Two Neighbors That Don’t Get Along

14:04 Get Super Laser-Focused

20:33 Learn How to Fail

29:39 Fair Judgment in Your Entrepreneurial Journey

32:40 Don’t Lose Connection With Your Greater Vision

37:21 Learn to Celebrate Little Things

41:05 Dream as Big as Possible




Get what you want, and fast! Tune in as @SfbaldwinOwens and @JayRooke talks about the essentials in the early stages of your entrepreneurial journey. #failure #perfection #self-care #SocialIsolation #vulnerability #RealisticExpectations #BeAnImplementer


05:34 “...we tend to put way too much weight on the quality of an idea… once we make that courageous leap, and then get into our entrepreneurial journey, we pretty quickly realize that the execution is where it's at.” -Jay Rooke

09:22 “implementing is so important… Even if we can't implement it, it's finding the people that can.” -Shirley Owens

14:08 “You've got way less time available to you each week than you think you do. Get super laser-focused. Figure out what is that performance schedule that gets you in your best groove.” -Jay Rooke

16:44 “A good indicator to look out for to know if you're drifting in the wrong way… is if your mind is filled with a lot of should’s and shamings.” -Jay Rooke

22:30 “Entrepreneurship is way more elusive… There's often this massive misaligning of realistic expectations.” -Jay Rooke

29:05 “People go down fast because mentally they're not prepared for failure.” -Shirley Owens

29:46 “Entrepreneurial journey becomes the personal development path that gets us to who we were supposed to be.” -Jay Rooke

30:58 “We… need to put fair expectations on our efforts.” -Jay Rooke

36:56 “We wake up every day and life just happens to us unless we happen to life… We need to have an intention every day of what it is that we're going to do to get to that place.” -Shirley Owens

37:51 “Every win gives you more energy to get to the next win.” -Shirley Owens

39:49 “Entrepreneurship is a game; be playful in it. No one's getting out of this journey alive; don’t be so serious.” -Jay Rooke

43:27 “Those that prioritize their self care tend to accelerate their entrepreneurial journeys more quickly than others.” -Jay Rooke

Connect With Jay:

A member of Forbes Coaches Council, Jay Rooke, J.D., is a trained executive and business coach who resides in wine country in Sonoma, California. Jay spent the first half of his life on the East Coast where he worked as a toxic tort litigator for the City of New York, as well as helping Merck pharmaceuticals launch the first-ever anticancer vaccine. He attended culinary school in New York City, and later opened his own restaurant in California. Prior to coaching, he most recently worked for NBC Sports; he also has experience working in the clean tech, sustainability and wine industries. Jay is the Co-Founder of, a charitable initiative to provide 1,000 shoes to 1,000 underprivileged kids when they go back to school in the fall.


Shirley Owens: My guest today is Jay Rooke. Jay is a Business and Personal Development Coach, host of the podcast, Know Pain, Know Gain: Entrepreneurship Made Real. He coaches first time entrepreneurs and small business owners. Welcome Jay.

Jay Rooke: Shirley, thank you so much for having me on the show today. It's a real honor to be here. Thank you.

Shirley Owens: Awesome. Well, I also know that you are a Forbes Coach Council. You are a former attorney from New York City. You have worked for Merck Pharmaceuticals and NBC Sports. You run mastermind groups, and you're the co founder of Giving Kicks, which is a charitable initiative to a thousand shoes to a thousand underprivileged kids for going back to school. So wow, you have so much about you.

Jay Rooke: Thank you, I appreciate that.

Shirley Owens: You really don't even know which place to start. I'm gonna let you start, and kind of tell me how all of this came out, or some of it

Jay Rooke: For sure, yeah. So I think the seed of all of this, if we're focusing on the theme of getting what you want, came for me earlier in life from realizing that I wasn't getting what I wanted. And so, when I was an attorney, I was just very unhappy with the practice of law. It wasn't fulfilling me on a soul level, and I just don't think I was in my area of giftedness. And so, that started this long and secretive path for me to try to figure out what makes me happy and how I could most feel fulfilled in what I was doing, and that involved me leaving the law. And at that time, I thought I wanted to open up a whole food store and went to culinary school, and ultimately, you know, would not pursue culinary things at that point in time, but rather went into the corporate world for about a decade in sales and marketing. And you know, that was still eating at me around not fully getting or manifesting what I wanted yet in life, which was some type of business ownership, but I just didn't know it at the time. And I attempted to make a big and courageous leap and opened up my own restaurant, which I jokingly say became an involuntary nonprofit pretty quickly and I lost everything. So that was my initial foray into trying to really get what I want on a big level.

Shirley Owens: Wow, that's crazy. Restaurant business is rough.

Jay Rooke: All day. Yes. Yeah, yeah, yeah. There's little aspects I miss about it, but certainly, you know, the mounting costs and the monthly expenses were pretty scary.

Shirley Owens: Yeah. So then what?

Jay Rooke: Yeah, so then what? It was a rough period of time. It was a pretty dark period of introspection and trying to do a post mortem around, you know, what went wrong? And with everything related to the restaurant, and how did I manage to make that mistake? And through that process, what I ultimately learned was that, while I had certain skill sets from corporate, you know, and a law degree, and that I looked good on paper, what I hadn't yet learned was how to think like an entrepreneur. And so, I'm the type that does not like being told that they can't do something, and if there's a, I kind of view all of my problems as fixable. So what I had done at that point in time was just really committed to learning what I didn't know. And I went to coaching school, started to invest tens of thousands of dollars in business coaching programs, and really paying attention, and using all of the skills, and curiosity, and the analytics from my prior careers. So it help come up with a program around helping entrepreneurs, especially first time entrepreneurs, learn how to think like an entrepreneur, which in my experience is usually the missing skills that when businesses aren't working out.

Shirley Owens: Wow. So being an entrepreneur is hard. It is, you know, people say to me all the time like: "Oh, you're so lucky, you're an entrepreneur." Or I'm like, what even is that? Like, I don't even know. It's just, I feel like sometimes it's just this group of us that don't really know how to, or don't want to, I guess, fit into that nine to five world, or you know, we're chronic idea disorder people that I just learned from somebody the other day, I loved that. And yeah. Tell me more about what thinking like an entrepreneur is? Because sometimes I feel like it's a curse, and to just to be in this place and always wanting to do something more bigger and better, but then kind of not having that, like you have this training, I feel like you have to use two completely different sides of your brain to do what you did and coming from that and being in this.

Jay Rooke: Yeah. I think that's a very insightful question. YES, I totally agree with you about both sides of the brain. And the problem is it's like they're like neighbors that don't get along, you know, they're not complementary to each other. And so, I think let's get a, you know, just run down some of the things that you named. So that chronic idea disorder, I think for folks that have never been entrepreneurs before, we tend to put way too much weight on the quality of an idea and the rebelliousness of what we're doing, and thinking that that's going to carry the day. And so oftentimes, you know what, what we realize is once we make that courageous leap and then get into our entrepreneurial journey, we pretty quickly realize that the execution is really where it's at. And that just launching your first business is not at all a natural extension of your regular career path in corporate. It's a completely different animal. And so, I think where folks get themselves in a lot of trouble is they think it's just all going to work out, I said, as an extension of their corporate work and not realizing, Hey, I've got to actually build the business model. I've got to decide what it is that I'm actually selling. I've got to figure out how to package that. I've got to then do the marketing. And then, I've got to do the actual service delivery. And so, there's a lot of different hats, and I think learning how to effectively switch gears between those hats that you're wearing tends to be a challenge for, especially subject matter expertise entrepreneurs because they like to stay in their wheelhouse and do their thing. Like you said, a lot of not wanting to do those ancillary parts of the business. So, I would put that executive functioning as a really big component of what folks need to learn and how to set up their days so that there's time for both working on the business and working in the business, and then I think the other big missing piece would be something around emotional intelligence and learning how to fail.

“...we tend to put way too much weight on the quality of an idea… once we make that courageous leap, and then get into our entrepreneurial journey, we pretty quickly realize that the execution is where it's at.” -Jay Rooke

Shirley Owens: Yes. It's so funny that you're saying this is some stuff for me. My husband is an Anesthesiologists, so very, everything is micromanaged, right? Like to the milliliter, to every single thing, like, you can't go wrong, you can't just be like, Oh, I'm going to wing this, like what I'm doing right now on this show.

Jay Rooke: Are you feeling sleepy? No, let me throw in a little more.

Shirley Owens: Yeah. So for him, everything is laid out. It's laid out by other people, it's put in front of him, and it's very micromanaged, and his mind works completely different than my mind, in a lot of ways. So I'm kind of like, Hey, I'm just very spontaneous, and go wherever the wind takes me, you know, like, Oh, that's so magical, we need to go there. And his mind is like, when are we going? How long is it going to take? What do we have to do to get there? You know, what are all these little things? And I'm just like, Ugh, none of those are fun for me. And so, we were having a conversation once with another couple, and he was saying: "Oh, you've got to read this book, Rocket Fuel." And it talks a lot about being a visionary versus an implementer. And I realized that in my entrepreneurial mind, I am not an implementer. Like, I have every great idea in the entire world. Like, I can come up with ideas. And I was actually a business consultant. I worked for a business consulting. I mean, I ran a business consulting firm, and I was very successful at it, but I was more telling them, this is what you need to do. And all of my ideas were great, but they were doing it all, which is different than me doing my own business. I was giving them all the ideas, but they were filled with implementers. And so, they were able to co-create with me, and be able to say: "Wow, you have made our business this much more percent." And so, in my mind I think, Oh, I'm really good at this business thing. But now that I'm, well not now, I've been doing my own businesses for my whole life. But I think that really realizing that implementing is so important, and my husband is going to love you because that's, he's always like, well, who's going to do this? And even if we can't implement it, it's finding the people that can, right?

“implementing is so important… Even if we can't implement it, it's finding the people that can.” -Shirley Owens

Jay Rooke: Totally. And I think a huge point that you bring up though is that a lot of folks overlook is that realization that, Hey, I'm more of the visionary type and these are the things that I like to be doing. And so, I think oftentimes when we're working our way up the entrepreneurial ladder, it's this sort of sense of martyrdom that we have to do all of these things, all of these apps, and check all of the boxes, and to your point, if we're paying attention and have that emotional awareness, we can start to feel, Oh, these particular activities or disciplines are energy vampires for me. Oh, these are the ones that I freely and gracefully bring out my best in. And starting to pay attention to those so that you can get to the point of saying, Oh, I should be the visionary in my business and I now need to either delegate or partner with an implement, or whatever that looks like. Whereas, I think a lot of times when folks are coming out of corporate, they have, for so much of their working life been put in a plug and play type of role. Hey, this is a sales opportunity, you do sales. Hey, this is a marketing role, you do marketing. And they don't really think as bigly about what role they play in the business, and then all of a sudden they start their entrepreneurial journey and there's this tremendous freeing up that goes on around having to touch all of these different disciplines and roles that I think can get really overwhelming for someone that's not used to that. And when unchecked what happens is that someone is sort of doing them all but doing them all poorly and feeling really overwhelmed, really whipsawed with their entrepreneurial journey on that front, and then being able to get their arms around it. Say like you did, okay, I'm the visionary. These are the areas where I spend my time, and then I hand the Baton off to somebody else that's better at this than me is 100% the way to think about it.

Shirley Owens: Yeah. I'm hearing your brain switched back and forth right there, awareness is my favorite word. I think when, with my husband in his previous life I guess, cause he's really kind of doing what you're doing where he's moving both back and forth between those two worlds. But you know before, he doesn't have to necessarily be aware because the monitor is aware of their breathing, and then it tells him their breathing is like this and then he does this. And so, in that world, like you say, it's just kind of like it's just handed to you, given to you what you need to do, and you can be really good at what you do but it's still coming at you. And as an entrepreneur, we are kind of control freaks a little bit. Like we think we need to do everything because it's our idea, and at least I'm speaking for myself and others that I know, and we don't only have to, like for my husband, he went to 14 years of school, that was put in front of him. Then he goes to work. His patients are put in front of him, the equipment's put in front of him, you know? And so, he just follows this path. And as an entrepreneur, you have to create a path, and then implement the path, and then succeed or fail on the path. And it is such a, it's just so much but when you're in it, you think you can do it because you see the bigger picture. And so, I'm hearing you talk about awareness and I like that because, or energy sucking, that's also some, like, seems like a little bit of a world cross there.

Jay Rooke: Agreed. Yeah. And I think it wasn't until I kept stubbing my toe and failing enough to realize, Oh wait, both of these worlds are necessary, that the emotional stuff was informing for me what I intuitively knew and was feeling about the business. And then the more kind of top down control stuff was necessary to allow my creative and artists types to flourish. So I needed just enough structure to allow me that bandwidth to go and do my thing but left with no structure. I was just kind of spinning and being less productive. And if we think about your husband's scenario, presumably the hospital and the anesthesiology department has done, has set up a series of technology, and standard operating procedures, and checklist, and additional assistance, et cetera, to allow your husband to be set up to perform in his area of brilliance. Whereas, if he could go through that same amount of schooling, but if they gave him none of that, it's going to be way harder for him to be great. And so, I think that's part of the game, especially for solo preneurs is realizing, A- you've got way less time available to you each week than you think you do. Get super laser focus, figure out what is that performance schedule that gets you in your best groove. You know, maybe that's hocking client meetings in the mornings, and then doing the creative work in the afternoons, or whatever that looks like for everybody. But then oftentimes, there's this need to implode certain parts of the business as we get this new found awareness. So we might have added in a some false belief like, Hey, I need to post on social media once a day. Or I need to write an article once a month. Well, if that's absolutely killing you and it doesn't work for you, and you know, it's an energy vampire and on and on, slash and burn that. And maybe your great live in front of people and more in the moment in which case make a recorded YouTube videos, or Facebook lives, be your stock and trade, and really aligning the business components to fit you versus that cookie cutter off the shelf. Hey, somebody else in my space is doing this type of advice.

“You've got way less time available to you each week than you think you do. Get super laser-focused. Figure out what is that performance schedule that gets you in your best groove.” -Jay Rooke

Shirley Owens: Right. I love this so much because I personally thought that I had to do everything. Social media is not my favorite thing. Whatever things out there that are attached to it, but it's always been like a really hard thing for me, and I kind of thought that I had to be like everyone else. Like, I need to post, like you say, I had to post every day on Instagram, and I had to be vulnerable, and I had to pull this part out, and pull this part out. And what I've learned is I can pick one or two things that I can do and I'm able to do and do them consistently, and it shows up the same way. And I don't need to show up in the world like everyone else's, that's the uniqueness of it. And that's what makes me more successful than I was before because I'm just getting to show up as me and what aligns for me.

Jay Rooke: Love that. And you know, one of the things that's so cool about that, as we switched back and forth from these two sides of the brain, that one might be more on the woo-woo end of the spectrum on the more sort of hard businessy end of the spectrum as a strategy. That's a brilliant strategy because no one on the planet is better at being Shirley than Shirley.

Shirley Owens: Right. I did not know that.

Jay Rooke: And so, you can really embrace, Hey, here's how I work. Here's how I'm hardwired. Here's kind of my users operating manual for getting the best juice out of me. And then building around that, you keeps it so much stronger. And I think a good indicator to look out for, to know if you're drifting in the wrong way on this one is if your mind is filled with a lot of should and shaming around you, like you said, Oh, my peers are doing this and why don't I have that? Oh, should I have an auto scheduler? Oh, I didn't even send out an email newsletter this month. They're just momentum these and self-confident these around all of these shoulds. And so, for me, if there's any SHOULD, it's that you SHOULD be operating in the way that serves you best and letting everything else fall by the wayside. And that typically means either you choose a business strategy that supports keeping you in that group, or it means building the business in such a way that you're pulling in those complementary partners that take things and run with them in whatever direction you can't. And I think the other thing that I want to add on to this massive run on here is the perfectionist and how oftentimes, especially the folks of your husband's level, I usually work with a lot of the overachievers and over educated types of the world that have like crushed incorporate and haven't had a lot of failure and the 4.0 and all of that, when they leave that nest and enter entrepreneurship, you could imagine your husband's head exploding with the amount of freedom and all the messiness that there is with entrepreneurship. And so, when those types try to make everything perfect in their business the way they did in corporate, they lose a ton of time cause they're basically running around the ship, buttoning down extra hatches all the time versus saying, Hey, B+ in this particular category is good enough. I need to focus my time back over here. And really started to learn where they leverage their time and the impact on their business most effectively.

“A good indicator to look out for to know if you're drifting in the wrong way… is if your mind is filled with a lot of should’s and shamings.” -Jay Rooke

Shirley Owens: So smart. I'm loving this Jay, because you say that, and my husband's gonna be like, why was this whole show about me?

Jay Rooke: Yeah, it was I was thinking about.

Shirley Owens: Yeah, no he's amazing. Like, he is so good at what he does, but he is, it's funny cause we'll go out to dinner and he would be like: "So, what's your intention for the night? What are we going out to dinner for?" And I'm like: "I don't know, just like friends. I just want to say hi." That kind of people, love people, you know? And now he's really, he's just so good about it because he's almost kind of stepping out of this and being like, I was aware that my patient had emotions today and I was able to talk to them, and you know, he's really bringing my world into his world too. So, but now I realized that I could say, Oh, my intention is not having an intention. Like, babe, I don't have an intention. I just want to go love people and I'll be like, cool, cool. Then let's just go love people. Let's just do it really well. Let's just be perfect at loving people. So, you know, it's kind of funny because I'm watching his transition where he's still in that every day and doing his perfectionism at work because you have to be. But then at home he's been able to just be like, Hey, I don't need to run everything. I can just sit back and watch this show and enjoying that. And I see that that's kind of where you are. And I love the idea of creating something that's just ours. Cause people will say to me: "Oh, my gosh, how do I become like you?" Or "I want to be like you." And then I'll be like: "Okay, let me go see how everybody else did it and then I'll show you how to be like me." So, I really want to talk about failure because I think that's a really important factor in this?

Jay Rooke: Yes.

Shirley Owens: I worked with professional athletes for 15 years. They'll do, and high achievers, and I'm married to a high achiever, and I think failure is so hard on them. So, I really would like you to talk about that, I'm certain that probably has something to do with what you teach.

Jay Rooke: Yeah, hugely so. And I really like what you're saying around, Hey, there's certain things where your husband has to be super dialed in and spot on it. And I think even for those types as entrepreneurs, there are things in everybody's business where we've got to be on, if I'm in a one on one coaching session, I would like to think that my client expects me to be showing up with my fullest in that moment. And as we talk about the way your husband's hardwired versus the way you are, I think it's a really interesting laboratory to just pay attention to because neither one is wrong or right. And there's like 9 million different other archetypes out there in the world, but it's starting to notice is one person in the healthy functioning end of the spectrum of their type or in the unhealthy one.

Shirley Owens: Yes.

Jay Rooke: And so, there's aspects where that perfectionism can be great. And then there's aspects where it gets taken to the extreme then did over yourself with more of that free flow, less needing to control the environment, go with the flow type of thing. And so, I think what to look out for is not trying to make yourself one that you're not because that will force you to underperform. But it's saying, Hey, how can I be in the healthy sweet spot of my continuum in the way that I'm hardwired versus perfect on another end. That's it, failure. So, here's I think the two big things where failure comes into play, especially for like you said, those high achiever types, is that they've oftentimes not really failed at life. And I mean that as a compliment. And I use to be one of those people, it was like, they worked as hard as they needed to to do whatever they needed to to get to that next level. And I think that's the way our system is kind of set up. It's fairly linear. If we think about higher education, and then the job, and it started as an associate, and then maybe you make partner or whatever that looks like, but entrepreneurship doesn't look like that, you know? Entrepreneurship is way more elusive. And what's amusing is that same, let's call it athlete type that has, you know, practice hitting a baseball 50,000 times assumes that he's going to bring that same level of expertise to his first go around at entrepreneurship. And so, the first thing I would throw is that there's often this massive misaligning of realistic expectations.

“Entrepreneurship is way more elusive… There's often this massive misaligning of realistic expectations.” -Jay Rooke

Shirley Owens: For sure.

Jay Rooke: That one out of the gate, Hey, be nice to yourself. I've yet to, I think I've had, I've been business coaching for almost eight years now, and I've had one client that massively exceeded all my expectations for what she did in year one. And I would say, everybody else grossly underestimated how long it was going to take them, and they thought they would get to that first ring of success within the first 6 or 12 months, and it's just oftentimes not the wet. So, one would be realistic expectations and giving yourself some buffer room. And then the other one that I think I would actually sort of a two part, one, I'll throw out there around failure, which is, when it comes from a seat of fear and how, what is this going to look like publicly? Oftentimes, you know the high achievers, a lot of them worried about what a lot of their peers think and that they're doing something new outside of the normal realm. And so, when it comes from a place of fear, they oftentimes start making business decisions not based on achieving success or getting into that flow like we talked about of their best area of giftedness, but more so around how to avoid failure.

Shirley Owens: Yes.

Jay Rooke: So it ends up being this kind of watered down version of their greatness and it's often someone else's playbook, usually like their own inner critics. The playbook for how to stay mediocre versus making the big leap. And so, it's ironic and painful to watch because the individuals made this huge leap to go and start their business. But now once they're under the hood and executing it, they might throttle back a lot more and start to make more decisions based on avoiding failures.

Shirley Owens: Oh, that makes so much sense.

Jay Rooke: Yeah. And then the final one that I would add into this is boys at a long tough road as an entrepreneur, especially during the early months and years, and most entrepreneurs, especially solo preneurs suffer from social isolation. Like I said, rarely are people's books looking so awesome in those initial months where the entrepreneur is like, Ooh, I've got this, no problem. Also as things go, it's usually a way slower start than they intended. It's usually periods of, Oh, my God, what have I gotten myself into? There's some imposter syndrome cropping up, or watching money start to go out the door a lot faster. And it where this failure can really hurt is that they haven't learned how to be super nice to themselves and be their biggest cheerleader through the messiness yet. And they're usually more in that old world mindset of Puritan work ethic, crack the whip top-down is what's gotten this done. No pain, no gain type of stuff in their athletics, whatever that might be. And now having to learn how to tenderly embrace that vulnerability that perceived failure, recognizing that this is all part of the process and going a long term picture versus short term pain becomes a major challenge for them, and so, they can get quite dark on themselves pretty quickly. And then that takes longer recovery periods to get out of, not to mention all the bad decisions that were made when their headspace was in the dusk.

Shirley Owens: Yeah, that is all just so true, and I've seen it a lot, and I know you've seen it a lot, and I think that there's this place too where we see all these successful people now, right? We don't really see what they went through, or what they're going through to get there. And so, when we say, Oh, I am going to be like that, or I've gotten that, I'm going to do that. In our minds, we don't give ourselves a realistic timeframe. And that's kind of what you said, and I feel like that's so important because I know with, when you're working on that other side of the brain, right from the corporate place, there's a timeframe. You do this many classes, you get this. You go to school for this long, you get this. You do this many reports, you get this. You hang out with your job this long, then you have this. And you know, you're one kicks in for now, and your insurance kicks in now. So there's this path, it's so attainable because you see where it's attainable. But being an entrepreneur, it's not like that. Like, when I wrote my book, it's been out for, it's been in Barnes & Noble's for over a year, and it's, I don't know, it's just hard to explain because you think that, and right now, it's starting to pick up all this momentum. And I'm like, Oh, finally it's starting to pick up momentum. But before you expect that the minute, the day that it hits Barnes & Noble's shelves, it's going to pick up momentum. Like, the whole world's supposed to just know that my book is on the shelves, and they should just go buy it, and I should be famous, you know?

Jay Rooke: Yeah, totally.

Shirley Owens: And I think that people think that when they, especially like you say, when they come from the corporate world of being really, really good at what they do, like, Oh, I could do this, right? I could do anything. I'm so good at what I do. And I see that with a lot of ballplayers when they come out. I worked primarily in Major League Baseball and they want to start a business when they come out, and they have these great ideas and these great ways of helping other people become great baseball players. But it's the business part that's so hard, and they go down fast. People go down fast because mentally they're not prepared for failure. And I have a son who played college basketball. He's been number one his whole life. And right now, he's trying to figure out what he wants to be when he grows up, and he's 23, and he's just like, I don't know, I've always had everything handed to me. He really has, he was a teacher's pet, he was the coach's pet, he was good at everything he's done. And I'm really realizing that he needed failure to grow even more, and we all need that. And so, you're just so much stronger on the other side of failure.

“People go down fast because mentally they're not prepared for failure.” -Shirley Owens

Jay Rooke: Absolutely. And that point you bring up for your son, that's certainly been true. In my story as well, is that the entrepreneurial journey becomes the personal development path that gets us to who we were supposed to be.

“Entrepreneurial journey becomes the personal development path that gets us to who we were supposed to be.” -Jay Rooke

Shirley Owens: For sure.

Jay Rooke: Right. That's when the deep digging in starts to occur, and all of a sudden we find ourselves asking questions like, what do I really want? And what are the things that get me there? Like you said in prior iterations, it's okay, the college has set up the structure of this. That's how far I have to play this game. To the corporate health is X, Y, Z. But when all that gets taken away, there's a lot of nudity leftovers, if you will, in this like, Oh, my gosh, what do I do with all of these things? And it's a first time learning how to process all of them for most people. And it's not necessarily on the healthiest stage to do it because once you've made that business leap, it's so public and the time clock starts ticking and all those things.

Shirley Owens: Right. And in your mind that's ticking, even though it may not even be ticking.

Jay Rooke: Totally. Totally. And you know, something I wanted to add on earlier when you were mentioning your book, a business coach of mine give me really strong advice one day which was that, we need to, in the same way that we're switching back and forth between that more business strategic minds, maybe more creative emotional one. We also need to put fair expectations on our efforts. So in the bookcase, like what my mentor had said was: "Listen, there's long term, medium term, and short term marketing plans, and you've got to figure out which one your initiative is in, and judge it accordingly." And so, at the time, I was doing an entrepreneurial speaker series where I was more concerned about, Hey, is this failing? Not realizing that, Oh wait, this is a long term play, not ones of you in the minutes a minute. And we're in such a mindset, especially coming from the corporate world where there's quarterly earnings, or like you said, Major League Baseball where at the end of every game there's closure and finality versus, Hey, if you're really trying to build up muscle strength that's going to take months at a time, but you know, we don't often give ourselves that same freedom of time that we deserve. And as such, put these undo timelines on top of things, which then further starts to fuel the fires of that failure unfairly to ourselves.

“We… need to put fair expectations on our efforts.” -Jay Rooke

Shirley Owens: Oh, so would you say that in a sense you help people get rid of that checklist mentality, but there's still a checklist, right? Like, there's still, like you say, then you have to reset your mind to make goals, I mean, I obviously, I'm launching my podcast at a certain time, so yeah, obviously have to have all these things in place in order to get that done. But it's a different kind of checklist, but it's still there. And so, do you kind of reprogram that in someone that it doesn't follow this path, but there's this new path, but you have to create it yourself.

Jay Rooke: For sure. Yeah. It's like you said, there's always those, we can't avoid all of the must do's that are in the world. You know, at some point in time there's only so many things that we can strip away. But to your point around this, how do you make it work more for you? So in the example of the podcast, it's going to look something like, all right, I need to create a quality audio, and I need to have some type of relative consistency of what I'm posting new episodes. But outside of that, you've got a lot of freedom. And so, I think oftentimes, and this is really, you made a great point earlier that I want to loop back on, it's appropriate to this, which is, when we see somebody's business who is successful, we start to try to emulate what they've got going on. And especially if we've come from a larger corporate environment where there's entire departments dedicated to these things, we as the solo preneur started to try to duplicate the systems and processes that we had in the 500 person company that might be mature at this point in time, which makes no sense at all. And so, let's pretend you do see a successful coach, or consultant, or whatever it might be that's multi-years in, there's clues for success that are left behind, but you almost want to be recreating what they were doing at year three in their business, not what they're doing now at year 15 because your infrastructure and your mindset and your rhythm isn't there yet. And so, going back to what's appropriate now, for example with the podcast would be, okay, let's boil this down to what are the minimal amount of must do's. Figure out how to get those done. And that might mean some type of mindset shift, like you said around, Hey, how do I relate to these things? So oftentimes, when we get ourselves, especially the visionary types, when we get ourselves in trouble and the passion falls out for our work, or we feel like the structure starting to cramp us, it's often because we've lost connection with our greater vision. So if I get, if I'm saying, Oh, crap, I've got another podcast, I've got a record today, that can feel onerous. If I flip the script to, Hey, this is really cool, I get an opportunity to have a fruitful conversation with somebody that might help someone else achieve their business success and avoid failure, it's much more inspirational now.

Shirley Owens: Really just simple switch to--

Jay Rooke: Totally, Yeah, it's often not a lot of work. It's the more been deliberate around this stuff that I think folks get themselves in trouble with. It's way easier than folks sometimes think it might be, but it's gotta be deliberate. Otherwise our prior default brain takes over and runs more of these processes. And then last up for you would be something like, okay, what are the ways? Be fair to yourself. Hey, for the next six months, what are some of my goals look like around the podcast? What are some of the things that I'm going to evaluate myself on? So you might switch from, Hey, you know, determining which metrics serve your style the most. So if you want to look strictly at downloads and listeners, that's one, but maybe a more fruitful one right now is, Hey, are the quality of my guests getting better and better the more I go along? Hey, is my interview flow style getting more effective and more aligned to my unique style? Am I getting more referrals for guests on the show? Whatever those types of things might be that serve you to that next step, and then reevaluate it as you get to the next step down the road, so maybe months six passes and now it starts to look like, okay, cool, I'm orbiting around center mass a little bit better now, I kind of understand my theme and mission a little bit more clearly. How do I start to now build in a membership program, or a community, or whatever that might be that takes this to the next level. So doing things incrementally and not all at once in that world.

Shirley Owens: I love that. You know, I had a client once, and this is kind of a little bit off, but it comes back to the same thing. I had a client once, she said: "I'm so overwhelmed, I'm just so overwhelmed. I have 15 things to do, and I need them all done in two days, and I just can't seem to get them done. I'm not getting anything done." And so, I was like: "Well, let's just make a list of these 15 things, and let's just check off one at a time. Even if you do it one thing one day at a time, in 15 days, you're gonna have it." And I think we wake up every day and life just happens to us unless we happen to life, right? And it's the same thing with our business. It just kind of happens unless we happen to, and we really need to have an intention every day of what it is that we're going to do to get to that place and more than we need to keep looking at that place that we're trying to get to, and being overwhelmed with getting there.

“We wake up every day and life just happens to us unless we happen to life… We need to have an intention every day of what it is that we're going to do to get to that place.” -Shirley Owens

Jay Rooke: I love that. I think that's super spot on. And I think, like you said, two things in that, one, setting those intentions. And then number two would be celebrating all of those little micro wins along the way. Those prior high achievers usually only celebrate those major milestones and that will leave your fuel tank really empty pretty quickly in the entrepreneurial world.

Shirley Owens: Oh, for sure. Yeah. Like I said, being an entrepreneur isn't all cut out like what people think it is. There's a lot of work there, but then when you can celebrate those wins, every win gives you more energy to get to the next win.

“Every win gives you more energy to get to the next win.” -Shirley Owens

Jay Rooke: For sure.

Shirley Owens: More energy to get to the next win. And everybody needs that. We all need those. And so, the more micro you can create those, like you're saying, let's start with the teeny tiniest wins because those lead to the bigger ones.

Jay Rooke: Yup. Going back to being fair to ourselves in the Major League Baseball thing, it's tough to evaluate ourselves for home runs straight out of the game, so don't do that. I know it's kind of crazy to say ignore your finances, but to some degree, you know, I advocate for that. Obviously, someone needs to keep a loose eye on it, but it's not the most successful metric to focus on usually during the first few months of someone's business where they just turn it into a self shaming exercise of what's there or not there versus looking at what they're actually creating and linking that to what's important to them right now.

Shirley Owens: That's so true because when I work with baseball players, it's usually, it's always because they're going through something that's just created an obstacle and what they do. And I often find that they're forgetting why they started the game. They're forgetting about the love of the game, you know? And when we can have passion in what we do, everything else kind of falls in place, and it falls in place because we make it fall in place and we work hard to fall in place. But when there's passion, there's just, there are those wins, and there are those intentions, and there is that awareness of what takes from us, and what feeds us. And so, I would say that you're right on that, that we just need to, I don't know, we really just need to be kinder to ourselves.

Jay Rooke: For sure. As you mentioned passion, what comes up for me with the baseball player analogy is this sense of play. Let's not forget to be playful, baseball is a game. Literally, entrepreneurship is a game. Be playful in it. No one's getting out of this journey alive.

Shirley Owens: Enjoy it.

Jay Rooke: Don't be so serious.

“Entrepreneurship is a game; be playful in it. No one's getting out of this journey alive; don’t be so serious.” -Jay Rooke

Shirley Owens: Yeah. And it's hard coming out of your world of seriousness. I mean, an attorney--

Jay Rooke: I consistently, that's sort of Achilles' heel area for me where I need to consistently come back and make sure that I'm owning that right mindset when I'm don't have a strong awareness around that. That's the one where I can shift over and start to be way too serious analytical. Usually my symptom of that is, what I'm realizing that I'm not loving being in business or feeling like a little bit of a martyr to my business. I'm like, Oh wait a minute, I've gotten way to that side of the brain.

Shirley Owens: Yeah, I for sure get that. Oh, my gosh, this has been so great. I like to ask two questions even though I feel like my podcast is not really structured, it's just kind of like a conversation. I feel like our conversation was so insightful to me today. But I always ask two questions at the end, and one is, do you have any regrets switching over from doing what you're doing now from what you did before? Or do you have anything that you would change going through that process?

Jay Rooke: You know, if I could change something, it's a good question. It would kind of relate to your theme about how to get what you want around some of these things. And for me, I wish that I had allowed myself to vision, and dream, and play more effectively in that realm of what I really wanted back at that transitional period of time of realizing, okay, I don't want to practice law. I think, instead of creating the biggest vision that I could find for myself and pursuing it, I kind of chose the next available rung and was more incremental about that. And so, oftentimes when we go to the buffet of life and choose from what's already there, things feel like compromises, and they're not the ideal fits. And so, for listeners that are at that stage, I would say really allow yourself the freedom to dream as big as possible, and don't let the house get in the way. If you start to cross over to the house, that'll shut down your creativity super quickly. And I wish that I had given myself more of permission to dream a little bit more radically, which would have got me in this direction a little bit sooner, you know? But we can't judge the path that was there. But that'd probably be the biggest one that I would look back to.

Shirley Owens: Yeah, that's definitely something that I think we all do. Just really enjoying the process more and being okay that you're there.

Jay Rooke: Yeah, exactly. And going back to this stuff around your son, around teachers, and grades, and coaches feeding that tank. I think, I was so focused on success as defined by other people at that point in my life that that's what I was most trying to next get was just some level of success versus a level of evolution for myself and fulfillment.

Shirley Owens: Yeah. So if you could leave our listeners today with one thing of advice, one word of advice, or one action that they could start today to move in that direction, what would it be?

Jay Rooke: Good question. So let's see. So, I think the biggest thing that I'm learning more and more as I work with more high achievers is those that are prioritize their self care tend to accelerate their entrepreneurial journeys more quickly than others. And so, especially for, again, those high achiever types that think they've got a really good tool set at their hands based on their prior experience. It's often the mental emotional game that is most lacking at that stage. And nobody likes to hear that, cause we don't like to think that we're off in that regard. But if we think about the way that we might invest in higher education where it's 16 to 24 years of people's lives at some point in time, or how many years we spent in corporate crafting a particular trade or skill set, it's insane compared to how much time we've spent getting to know and master ourselves and learning how to navigate our own emotions, it's usually crazy exponentially off as a ratio. And so, I think for me that's where the fastest growth and most low hanging fruit is focusing more time there as you try to solve solutions in your business than it is at looking at some of the, let's call them more businessy things, like your marketing message, or your strategy, or whatever that might be at the time. Like we said earlier, both are necessary, but I'd see people over focus on the businessy stuff and not enough on the other, it usually ends up having them going up the ladder and then realizing that the ladder was placed on the wrong wall.

“Those that prioritize their self care tend to accelerate their entrepreneurial journeys more quickly than others.” -Jay Rooke

Shirley Owens: Makes sense. Yeah. Enjoy what you do, love what you do, figure out what it is that you want, and go more in that direction, I love it. Well, Jay, I'm so grateful that you were here today. Tell me about how I can get in touch with you, how our listeners can get in touch with you.

Jay Rooke: Thank you, I appreciate that. Yes, I think that the easiest way would be going to my website, which is, that's J-A-Y-R-O-O-K-E.C-O-M. And if they go to, I've got my podcast there, which is all about helping early stage entrepreneurs and small business owners accelerate their journey. It's called Know Pain, Know Gain, but it's K-N-O-W for both. And I've got some other resources in helpful essentials on my website, so that'd probably be the best way. And then, once folks go there, it's got all of the click through for social media accounts and other ways to stay connected.

Shirley Owens: Awesome. All right, well thanks so much for being here today. I feel like this is so great and so insightful, and I learned a lot, and it was fun to have this conversation.

Jay Rooke: I did as well. And I want to say thank you to all the listeners for tuning in, and to you, Shirley, for having me on the show and asking such insightful questions. I really appreciate the opportunity

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