411 | Overcoming Overwhelm with Jaime Masters

Overwhelm is all too common these days. Overcoming overwhelm means that you have to be willing to change the way you do your work, but also the way you see yourself too. Jaime Masters is our guest today, and she shares her experience with overwhelm in a very vulnerable way. Jaime gives us concrete tips in overcoming overwhelm. This is a significant episode if you want to create more success and create a life that serves you on all levels.

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Target Audience: Jaime is a Business coach, author, and professional speaker. She interviewed over 350+ millionaires and billionaires and been helping business owners make things more simple and more profitable for the last 10 years.


Jaime Masters: The Transcript

Disclaimer: This transcript was created using YouTube’s translator tool and that may mean that some of the words, grammar, and typos come from a misinterpretation of the video.

Leaders in the trenches and your host today is Gene Hammett.

Gene Hammett: Hi, I’m Gene Hammett. I am the host of leaders in the trenches. And my question for you today is this, have you ever felt overwhelmed as a leader? Well, I know you probably have because I’ve felt it and it’s something that we all have to deal with and you’re not alone. I am talking today with Jaime Masters. She’s the host of the Eventual Millionaire, a fantastic podcast, but she also is a coach just like me. She works with a lot of owners, just like me, did help them understand, overwhelmed and create systems and really identify some of the things that are blocking them from their growth and their success. And I’m bringing her on because she’s got a fresh perspective around these topics and she’s going to share some insights with you, my guest here, leaders in the trenches. So stay tuned for that interview with Jaime Masters.

Gene Hammett: Hi Jamie. How are you?

Jaime Masters: Hey, I am amazing. How are you?

Gene Hammett: Well, I’m excited to be. Have you here. I am so pumped to be able to talk to you about what’s new in your life and what’s going on as you serve these amazing people. So thanks for being here at leaders in the trenches.

Jaime Masters: Thanks so much for having me on. It’s nice to actually see you again. It’s been forever.

Gene Hammett: I know. It has been forever, like years when I already introduced a little bit about you and told her clients, tell the audience a lot about you know who you are and how you work. I want you to tell him about your own self about who you are and who you serve.

Jaime Masters: So I’ve been a business coach, hardcore like an offline business coach for a very long time and went online for the past 10 years, which makes me feel very old in the space. But going back and seeing patterns over and over and over again. I have over 5,000 hours one on one hours with clients and realizing that we are so similar in so many ways as you’re going through and being a business owner and yet we feel so alone and so completely different than the rest of them. And so part of my mission, especially with the new programs that we have coming out, is to go, you’re not a number one, you’re not alone, which is a wonderful thing to hear, but number two, there are solutions that have already been prepaid in this network of crazy information on the internet where we’re trying to figure out what works and what doesn’t work. That’s my goal is to have the 80/20 what actually works in business for you specifically and just to get that information and that action out so that way you can actually see results. I feel like unfortunately nowadays there’s just so much information that could or could not work that was like scared to know, right. Which path is right for us. And so if I can just help as many people as possible and the testing mindset and trying things for yourself and knowing that you’re not alone, that’s what I’m here for.

Gene Hammett: Well, I know we’re not alone, but it feels like it sometimes. So why do you think that entrepreneurs feel like they are alone or that they can’t really open up to someone inside their circles?

Jaime Masters: That’s a great question because number one, we feel like we have to do it all ourselves, right? Especially just going back through, I know way too many personal issues of all the very amazing clients that I have and we lead ourselves up to this point, right? Where I feel like it’s not good enough unless I did figure it out myself. Right. One of the beliefs that we have, Yay. Go, team. Not serving us in any way. So what we’ll do, especially as if we have employees, we’ll keep it to ourselves. Like I’ve had a lot of clients that are like, oh, I can’t share things with my employees. Well, there are lines, don’t get me wrong. There are boundaries in their alliance. You don’t share absolutely everything but letting them in enough so that way you can actually let go of some of the responsibility because being a business owner, you feel like you have the weight of the world on your shoulders, right?

Jaime Masters: We have employment, we have payroll, we have cash flow issues, we have all this stuff. Our wife or husband is like, oh my gosh, you’re working too much. And on this son, you’re not seeing your kids. And that there’s always something that you should get getting better at. And because we feel like we’re supposed to know how to do it, telling anybody that we don’t know how to do it is crappy and for longer bull, like it feels not fun. And so a coaching relationship is one place where we can do that, right? Where we feel like, Hey, I’m paying them. I can talk about as much crap as I want. Right? But what I want to do is open it up for people to know that you can open it up and be more vulnerable in a good way when you’re with your employees and your clients. And so that way it’s not, it doesn’t feel so alone. You can reach out for help, which is one of the hardest things that we can do. Right. But set yourself up for success and all of that so that way it’s not a lonely road till you’re 80 and then you’re like, oh, that was fun. I made a lot of money go team. Right. Does that make sense?

Gene Hammett: Yeah, absolutely. And I can relate to a lot of the things you’re talking about there Jaime. Because in my work and my research, I see the value transparency, the ability to have honest conversations with our team to get their ideas and so that they don’t feel judged by having a stupid idea when you are working with, so transparency’s one of the things that I see and empowerment and all this stuff. When you were working with company leaders and owners to activate their team, what are some of the things that you see as challenges for them?

Jaime Masters: Okay, so I can only pick a couple, right? So some of the big ones are when I work in an owner when we first come in, so the owner bucks program that we have, the owners actually have a decision that they have to make, right? So we give them information on what decisions they need to make and then we actually work with their team. So my right-hand works with their right-hand half the time they don’t even have a right hand, they don’t, they don’t have anybody that they feel like they can have responsibility can be handed off, which makes them not be able to even let go. Right. So when I go, Oh, who would you consider on your team as your operator? We call one person’s the owner, we call it their operators, their operations person. But it’s the person that sort of running the systems because every business is made up of systems.

Jaime Masters: We have all heard that many times before, but who owns those systems? And usually it’s the owner and the smaller and companies like 20 employees or so it’s like they’re still trying to kind of do it and most owners suck at it. Like really bad. Like we’re visionaries. There’s a great book called rocket fuel that really talks about the visionary versus the integrator. And when they’re smaller companies, they don’t understand that they can’t afford a COO, right? But you cannot have somebody on your team that you can call your operator. So one of the very first things we do is go, well, who would it be? Right? So either they know hands down like, oh, it should be so and so. And they can actually start to develop the talent that is in them. So that way they can be more responsible because one of the issues is they feel like they’re not supported, so they don’t ask for help.

Jaime Masters: They’re not even asking or training somebody that could support them if they wanted to write for a long term. And so that’s the very, very first step we go, well, who is your operator? If they don’t have somebody that’s an operator, we usually do what I call a team test to start trying to figure out what their team looks like. Great workflow from the book who write with it has you sort of rate your team so that way we can go well, who raises their hand? Like who could potentially be moved up into this role? If we have somebody there, we’ll move them sort of up into that role. If we don’t have somebody there though, they have to go find them. And one of the reasons why their company is not doing as well as it probably could be is because they’re missing that gap of somebody that can really be responsible for those things.

Jaime Masters: Does that make sense? And so those are the big key pieces. Like, Hey, do we have somebody that you’re willing to give up responsibility on at all? And sometimes it’s a little lower level sign, like a project manager. It could be even an executive admin on the lower level side. It doesn’t have to be someone that is an operations person making six figures. I’m not saying that at all. But what I’m saying is that we need to find somebody that you can train well enough that you can actually let go that way you don’t feel so alone.

Gene Hammett: Yeah, and that’s really important. My core work really helps them use of responsibility about seven times. And I’m going to poke it, you’re just a little bit because I want fast growth companies to look at how people go beyond responsibilities to take real ownership.

Jaime Masters: Yes!

Gene Hammett: You call this owner’s box and then maybe that’s a part of your work too, but do you see that as being a challenge for people that are just, Oh, I need to get this work done versus owners like you and I show up differently with everything?

Jaime Masters: Well, I think, okay, so, so bucks ready. I think one of the issues though is that as an owner they’re not good at giving up anything, whether it be responsibility or anything. And so because they hold so tight right their level of micromanaging or their level of whatever, they can’t even give up the responsibility, quote-unquote, right? Yes. 1 million times better. It would be better for them to own it and run with it right there. The operator is a bazillion time better than so many efforts with details than with the owner in a million years, and yet the owner’s like, well, wait, let me just put in my little flavor. Oh wait, just let me. Right? They metal like all heck because it could be their company. There are all sorts of reasons. We’re making this stuff up as we go. People just like parenting, right? We’re doing the best we can. We’re learning the best we possibly can. Um, but the line of responsibility to ownership, I feel like the owner doesn’t even do a good job of letting the person do it themselves in many aspects of letting go in many aspects, at least the people that I work with anyway. Maybe you work with higher level teams, but the, the 20 or so employees can get a little dicey in there when they realize that, hey, you know what? They’re their own person and they could actually run with the ball too. Things change.

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Gene Hammett: You talk a lot about the value of systems and I went through a really revamping of my entire business this past year. There was a book I read clockwork, you know Mike McCullough?

Jaime Masters: Yeah, he’s coming back on the show. Oh yeah. And I

Gene Hammett: And I really felt like the systems that I was putting in place, although hard has allowed me a new level of freedom within the business. So what do you do with your clients around systems that you could share with us today?

Jaime Masters: Yes, and I did not read clockwork, even though I love Mike because I didn’t want to take anything that he said and many of my work. So what we’ve done is we’ve sort of 80/20 and what needs to happen at a business and the systems side. So for me, I have to do an assessment first because of systems for the system’s sake, our silly, right? So somebody that doesn’t have a lot of time or assets or resources are like, well I don’t want systems because it’s going to take up so much. Right? You see the upfront piece. So what we try and do is go through and go, okay, what’s going to give you the most bang for your buck up front? So we have different boxes that we have. So we have a company box, right? And the company bucks could include weekly meetings. Sometimes people don’t even have weekly meetings, all right.

Jaime Masters: They don’t have agendas set up for them if they had weekly meetings, I don’t have agenda set up and so very similar to like traction and those sorts of things. What are those key elements that every company that is successful has to have in it? The 80/20 of it anyway, that comes first, right? So a lot of the times it’s going through the teamwork first and going, Oh, teams have no systems. Where do we put the Sop? We don’t even know where some of the foundational pieces come from. Soon the upfront, she usually some form of tech problem, right? Some form of escalation process or plan that they don’t have. So whatever those top-level things because if you can get that one hinge, that makes a big difference. Escalation. I’m doing a speech next week about this because most I work with, a lot of agencies don’t have an escalation process in place.

Jaime Masters: Everybody pings the owner when they want to ping the owner, which is like not cool. Right. And you’d think self-explanatory, right? You would think that’s not a big deal. Um, but when it’s not in there, we don’t realize that that’s one of the main issues that’s coming up. Right. And so what we’re trying to do is go, okay, what is the most bang for your buck? What do I think is the biggest issue and what system can solve it? Because nine times out of 10, it’s a systems problem that can be put in place and of course given to the team. But that way you can free yourself up. So we’re not banging our heads against the wall over and over and over again. That’s a definition of insanity. And we do that like constantly as business owners.

Gene Hammett: Yeah. I love the fact that you’re talking about this and the way you’re talking about it, but I want to go back to the beginning. You mentioned 5,000 individual hours looking at at this and kind of looking at the commonalities. What is some of the things you can share with us besides we’ve already talked about not wanting to give up and us feeling like we’re alone? Other things you can share.

Jaime Masters: So one of the reasons why I started interviewing millionaires to begin with anyway is also to do the data. I’m a data geek, I have a degree in computers. So to me, pulling out as much data as I can that can help me and using it with clients was huge. So that’s some of the pieces that I started to do. So one of the things that I found from millionaires that I’ve found works extremely well with owners is that feedback loop, right? So it’s this constant forward motion, but not only concept forward motion, but reassessing where you’re at. Does that make sense? And so the clients that I see that don’t move as fast or don’t grow as fast are the ones that have a really slow feedback loop. And it could be for lots of different reasons, could be a team, it could be whatever those reasons are.

Jaime Masters: But whatever that feedback loop is, the shorter it is typically the double or tripling we can do when it takes forever to get feedback or to test anything and to get feedback and to go that path to ideally systemize it in the long run. It takes forever. And they’re like, okay, I really want to see graphs now. Well, you didn’t do the thing that I told you two weeks ago, so do that. You should have done it two weeks ago. Do you know what I mean? And so the patterns that come up over and over and over again, and sometimes it’s the type of owner, right? That we all have different types of people on the planet. But I found that the ones that can really have the massive levels of success that I’ve always looked to data mine is the ones that have really short feedback loops.

Gene Hammett: I love that. Cause I know how important it is within my own team. But I see the problem with my clients. Hey, they’re afraid to get the feedback or they’re not doing the work like you mentioned. And so they’re like, oh well I didn’t do that yet. So how do you get people to create better feedback with inside those systems?

Jaime Masters: Making somebody else bug the crap? It’s so technically yes. So for me, I’ll use me as an example. I avoid stuff I don’t like, Huh, who knew does mess to my clients? Right? And so knowing what my core strengths are, and I do this with my clients to knowing what their core strengths are, they’re going to lean into their strengths most likely, right? As humans, we do that, Ooh, I’m really good at this. I like doing more of it. The problem comes is if the feedback loop or whatever that pieces is where I don’t want to look right, whether it’s uncomfortable or whatever those pieces are, it makes it more difficult to go down that path so I can avoid them. Right. So for me, it’s funny, I was just chatting about youtube with you before and I was avoiding it. I was totally avoiding it and so I gave it to my team to make me responsible and have her actually manage.

Jaime Masters: I don’t like asking for help either. And I had that moment of, Hey, I’m slow as heck feedback loop-wise from redoing our youtube channel because I’m scared. I don’t like, I’m a perfectionist recovering, but right now it’s popping out big time. I’m in learning mode. Right. I’ve got all these excuses as to why I’m not actually doing the actions. Nobody was holding me responsible for it at all. Like not even checking in. And so because it was, I was like, it’s my project, I’m going to take it and go, don’t worry about me because it’s, I’m scared about it. Right? So whatever it is, it can be in any aspect in your business, but there are pieces like that you’re avoiding and having somebody out scope that’s outside of your comfort zone. Good to know. How can I help you? And then be accountability, be it is huge.

Jaime Masters: So for me as a coach, one of the pieces is to make them more accountable. Hey, you said you were going to do this. You’re not. You said you’re going to do this. He’s still not like there’s a reason behind why you’re not. And so putting in that feedback loop of accountability, doing what you say you’re going to do, kind of important. But again, super easy to avoid, super easy to avoid, but then you’re not going to get the results that you want anyway. So if we can actually put the accountability within the feedback loop knowing that would be really helpful.

Gene Hammett: One of the things I want to point out here is how truly vulnerable you are sharing some of the things that you’ve struggled with. A lot of people try to put on airs and it’s saying they don’t have these problems and we’re coaches. Like I struggle with things all the time. I’m trying to, you know, shift my language. I, I’ll say I don’t have enough time but realized I always have enough time for what’s the most important.

Jaime Masters: Just new on that one thing really quick cause that was my mantra for a long time. I had all the people around me call me out every single time I said that. So my children don’t give children things to do like that because they will call you out.

Gene Hammett: Yeah.

Jaime Masters: That was the lesson. A hard lesson learned. I literally set it probably 15 times every single day, every single day but not anymore. So that’s good.

Gene Hammett: I’m with you and I’m catching myself. I did ask my son a very critical question I’m going to share with you and I don’t know how your kids would answer this question, but I said, you know, cause they have a different perspective for life inside of what we work. And I said, what is this something you think I do too much of or you won’t be surprised when he said, daddy, you do too work. What would your kids say that you do too much?

Jaime Masters: I’ve asked them that and they also said work funny thing is I stop at three so kids come home, I’m done their level. So my parents worked constantly like my mom. One of the things when I was little, and this has just been my past, but my mom worked all the time and I was like, I just want my mom to be with me. So I’ve done whatever I possibly can to put my kids first. Now don’t get me wrong, I love working and I love showing them. Then what’s so funny though is that they have no idea what normal parents work live. Their dad is a professional performer and does show within their stilt walkers. They think that’s normal too. So interesting. Is there like work, I was like you guys, hey work maybe five hours a day when I’m with you like this.

Jaime Masters: I mean I love work, don’t get me wrong. But as far as the hours go, it’s not very much there. Like you are called the time like wow. Okay. So they would also say work. That being said, I’ve asked that question and gone deeper a little bit more too. And so they think I do too much. Well, I did do too much cleaning, complaining about cleaning cause that was another one. Right. So being able to be vulnerable enough to take the crap from your children. Yes. I’m still learning. I’m not great at it yet. And yes, I technically worked too much, but I don’t know. I don’t think I do anyway.

Gene Hammett: Yeah, I know I do because I still have some big things and big projects that are in the middle of, but you know that’s an interesting question for our audience to really reflect on where they are right now with their business is what would your kids say? Not what you think they would say, but what would they actually say? And we just opened up here and said it was about work.

Jaime Masters: And we make them do that and be like, okay action item for this. Go ask your kiddos. I think it’s hugely important to know what they,

Gene Hammett: It’s you know, I also put, you know, look at this perspective cause I really don’t have a context like yours. Mine has no, he’s never had a job. He’s 11 no idea what work really is. He wants to get paid to watch Netflix or youtube or whatever it is. So I have enjoyed talking to you. I want to give you one more chance to bring this home. Like if someone’s feeling overwhelmed, they’re feeling that sense that they know that that could be doing something else. What is something you would share with them or ask them as though your experience?

Jaime Masters: Okay, I’m going to give them an action item and I’m going to send a link so that they can go more because we only have a couple of minutes and I can’t tell all the things, but I would do a brain dump and a time audit. Those are the things that you’ve heard of a million times. I’m not saying it’s rocket science, I’m saying it works and just about every single time. So getting everything out of your brain, personal and professional, everything that you absolutely think of along with the time audit and actually paying attention to what you are accurately spending your time on. Whenever I work with many entrepreneurs, the first thing I do is ask them like, okay, what are you spending your time on? They tell me. Then I have them do a time on it and they go, oh, so cause you can’t, yeah I need the data.

Jaime Masters: You can’t squirrel away. And I added up and nine times out of 10 they go, oh I’m, my goal is this or my, this is this. And my habits do not reflect what the outcomes are that I want. And that eye-opening piece, I would highly recommend, I’ll give the link out eventualmillionaire.com/leaders will put on, we’ll put it just for your people, but I have a time on it for free, not even opt-in, nothing. You can go and watch those things, but I highly, highly recommend three to five days. You’ll hate me at first. You’ll love me later to make sure that they actually have the eye-opening moment because the honesty of where we really are not what we think it’s fine to be wrong is okay to mess things up. We do as humans. And what are you doing now to get better? And that’s the best thing that I know of right now.

Gene Hammett: Well, I love it because it’s always something we do. And I am curious and it would be a very quick answer. What is the difference between a project that someone thinks the time it will take versus what is actual? What have you seen over the…

Jaime Masters: I tell people to double it.

Gene Hammett: I think I have to triple it.

Jaime Masters: I tried.

Gene Hammett: And knowing how long that one video will take.

Jaime Masters: Yes, I time myself there too cause I’m at efficient Nazi. Right. But what’s so interesting is my previous executive Admin, I told her to tell me to Dell, no matter what numbers I come up with, make sure I double it right. So whatever that goal is, we’re doubling whatever we have to take for actions in order to actually hit those goals. Because I agree with you a million times. Maybe we’ll have to triple it to be on the safe side, but I agree with you a million times over

Gene Hammett: Dangerous sitting back going, Oh yeah, I can definitely do that. I can write that article and then

Jaime Masters: Let me add this. The next the sheet that I’m going to give you the research on flow. So I care more about getting in states of flow so I can produce more rather than how much time I have to work on something because the numbers, at least in my life are vastly different. Vastly different when it actually feels on it versus not. I did 17 videos in an hour and 10 minutes by the way. So when I’m on I can be on so you can’t write when I’m not on it. It’ll take me two years now. I’ll avoid it.

Gene Hammett: Jamie, thank you so much for being here. Where do we send our audience if they want to get more of you and I can keep in touch?

Jaime Masters: Well go get all that stuff for free with no opt-in from eventual millionaire.com/leaders so that we will get that. Um, and you can check it out on her [email protected] but you can follow me online. I do random rants on like this. Not all the time.

Gene Hammett: Fantastic. Thanks for being here at leaders in the trenches.

Jaime Masters: Thanks so much.

Gene Hammett: Love talking to Jaime. She’s such a pistol and she’s just so vulnerable and open. Hopefully, you enjoyed that as much as I did. I learned a few things that I need to be doing about my own time, about the audit and the brain dump and I’m going to be doing that as well. So make sure you follow the instruction, support Jaime and what she’s, but also, if you have any questions about your business and I can help you in any way, make sure you reach out and I’d love to help you and serve you as always, lead with courage and I’ll see you next time.

Disclaimer: This transcript was created using YouTube’s translator tool and that may mean that some of the words, grammar, and typos come from a misinterpretation of the video.

In this episode we’ll cover:

  • Why Entrepreneurs Feels like Alone
  • Great Workflow
  • How People go beyond Responsibility
  • Real Ownership
  • Level of Micromanaging
  • A line of Responsibility to Ownership
  • Massive Levels of Success



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