Navigating a business pivot can stir up a mix of emotions, from fear and uncertainty to excitement about new possibilities.

In our first roundtable discussion, we dive into the heart of mindful marketing transformations.

Joining me are special guests Jamar Diggs, Diane Mayor, and Diann Wingert, who share their firsthand experiences of steering their businesses through significant shifts.

From moving beyond traditional marketing roles to redefining their audience and messaging, each story sheds light on the challenges, wins, and lessons learned during their journeys.

In this episode of the podcast, we talk about:

  • Marketing your business through significant pivots
  • The role of feedback and intuition in refining your strategy
  • Lessons learned from navigating business transformations
  • Strategies for communicating and implementing changes
  • The future direction for our businesses in the context of mindful marketing

This Episode Was Made Possible By:

Riverside All-in-One Podcast & Video Platform
Visit Riverside and use the code DREA to get 15% off any Riverside individual plan. We use it to record all our podcast interviews!

Fab Fiesta
To celebrate my 10 year anniversary, I'm throwing a Fab Fiesta from April 15-24, 2024. 

For 10 days, I'm rolling out 10 exclusive offers – each day, a new surprise. And because I love a good party, I’m slicing prices by 50%. Want in?

About the Guests:

Jamar Diggs is a YouTube Marketing Strategist for businesses who want to leverage YouTube to create a low-lift marketing strategy so they can make marketing only 10% of their focus. He takes his corporate marketing experience from working in large marketing departments like and to help his clients create a content strategy and marketing system that will generate results for years. 


Diane Mayor is a business strategist who helps entrepreneurs build a strategy that goes beyond the funnel to make more and keep more in their business.

Each day as the host of The 5-Minute Strategist podcast, Diane shares one strategic question to get your gears turning and spark new ideas for growth, innovation, and leadership in just 5 minutes.

In her spare time, this spreadsheet-crazy, puzzle-solving, systems nerd is passionate about travel, live events, coffee, and Converse though not always in that order.


Diann Wingert became a business strategist, coach, and mentor after a 20-year career as a psychotherapist. Her mission is to help female solopreneurs with big ideas and busy brains get focused, fired up and flame retardant. Diann is the creator of The Boss Up Breakthrough and host of The Driven Woman Entrepreneur Podcast.


Watch the Episode Below:


Andréa Jones (00:00):
Marketing your business while going through a pivot can be a very challenging space to be as an entrepreneur and business owner, emotionally, spiritually, get the tissues ready sort of moment. And today I am really excited to have a wonderful, wonderful panel of guests to talk about how they marketed their businesses through a pivot. This is our first round table discussion here on the podcast. As an example of our own pivot, we are really bringing in more voices and adding more flavor to our conversation. So I'm excited to bring this new show format to you. Let's get into it.

Before we get into it, this episode is sponsored by Riverside, which is the all-in-one podcasting tool we now use for our show. And y'all, they feel super luxurious. Riverside is the all-in-one podcasting and video platform that gives you studio quality recordings right inside your browser. And y'all, it's super intuitive and easy to use. Once your recording is done, you'll be able to automatically download separate audio and video tracks and edit it all within a few clicks. It's really very easy. So head over to Riverside and you'll get 15% off. That's one 5% off, using my code Drea, DREA at checkout. But y'all, it's free to get started. So click the link in the show notes and get started today.

Alright, so today on the show I have Jamar Diggs, Diane Mayor and Diann Wingert on the show. And I am so excited to talk to each of them about their pivots, but we're going to give a little background about their pivot and where they are now, whether they're beginning, middle, and end of it all. And I want to kick things off with Diann Wingert. Diann, tell us, give us a little background about you. What are you pivoting from and where are you in your pivot?

Diann Wingert (01:49):
Well, I am in the midst of it. I'd say I'm in the messy middle. It definitely feels that way on all the levels. And for the last several years I have been marketing exclusively to female solopreneurs who are struggling to hit their stride in business because they're unclear about their positioning, packaging, and pricing. So where I'm headed is branding that is not focused on either gender or business type, but on the reasons behind the struggle, which I'm calling a DH ADHD ish because most creative and entrepreneurial people in my experience have these traits, whether they have a diagnosis or not. And I am moving away from labels of all kinds, gender and diagnostic.

Andréa Jones (02:36):
This seems super significant. As someone with a therapy background, how do you feel about moving away from the kind of box of the terms that therapy being a practitioner has given you towards this more flowy language?

Diann Wingert (02:54):
It started in 2015 when I was running a successful private psychotherapy practice. And I realized, and it was, I'd like to say it was one dramatic pivotal moment, but it was over a series of conversations with my then clients where I realized I have outgrown my role here. I was a wonderful therapist, and I know that there are times in life where a therapist is absolutely what you need. I do not consider therapists and coaches to be equivalent. However, I was at a point where I wanted to move conversations from talking about problems and pain to talking about purpose and potential. So it was time for me to grow into a new role, and I had so many questions and I still have so many questions. Why would you give all that up to become a coach? I mean, anyone can be a coach. And while that's valid, there's also a lot more freedom in coaching because as a therapist, you really have to conform to the norms of what your license requires. Your license is not portable. We moved out of the state, my license couldn't go with me, and I realized that that freedom was a good thing and my clients still benefit from all of my therapist training and background. It's not like I put that to rest. I just choose not to diagnose or treat people. I choose to partner with, mentor and serve them instead, but I'm still helping. Oh,

Andréa Jones (04:29):
That's beautiful. I love that. And I'm excited to dive more into that into this episode. I'm going to move over to Jamar now, Jamar Diggs, I so relate to your pivot because I know you as the YouTube guy, but now you're so much more than that. So talk to us about your background, what you're pivoting from and where are you now?

Jamar Diggs (04:48):
Yeah, so I've had so many pivots in the past few years, but I came from a YouTube marketing agency, so I was helping people with that. And then I decided to really pivot over into solo consulting. I love strategy. I really love helping my clients really identify the strategy that they can leverage with YouTube, but also more than YouTube. And really seeing their marketing strategy as that, a marketing strategy, a holistic and integrated marketing approach that just specializing in YouTube just isn't able to do. And I found myself being labeled as the YouTube guy, which I do not mind that, but I wanted to call in people that saw YouTube as an integrated part of their marketing. And so I kind of branded this phrase of low lift marketing. And so we're leveraging YouTube in these different ways as a part of your marketing strategy and how it can just integrate and really help elevate your business goals that you have. So I really wanted to try to make sure that I was calling in people who were interested in leveraging marketing to elevate their business goals, what are your marketing objectives and how marketing and sales work together? And I wanted to find people that really understood that. And so that's kind of where I am now.

Andréa Jones (06:34):
Yeah, and that's the thing that stood out to me about your pivot is this low lift marketing shift from YouTube to low lift marketing. I instantly understand how you are different from the other YouTube strategists out there who really seem to focus on more like influencer marketing versus creating content as a business owner. Would you agree?

Jamar Diggs (06:57):
Oh my gosh, yes. That's one of the things that I love that makes me stand out. It's one of the things that, because I focus specifically with business owners, I do not work with any creators or influencers. I don't even work with business owners who want to be creators, which is, I mean, it's not, I'm like, I'll never work with you, but I love using YouTube or using marketing as a tool to get more clients as a tool to get people into your marketing ecosystem. And I love that the low lift marketing verbiage is really resonating with people because you're right, when I was just talking about YouTube and giving these tips and all of the things, I'll always get that question where it's like, oh, but do you work with business owners? And I was like, yeah, girl, I sure do. And so it was not enough to just talk about YouTube, and I was doing a little bit of, actually no, I wasn't. I was teaching about YouTube for business, but with people that just see for a little blip of a second, sometimes it's hard to retain certain things. But when you understand low lift marketing and when you identify with making marketing more less complex and more integrated with your business goals, you're like, now how do you do that with YouTube? What are you doing? What are those parts? It really helped me create more conversations and really get down to the core of what business owners really wanted to achieve with their marketing.

Andréa Jones (08:38):
Yes, I love that messaging shift. Totally relate to it. So aligned with the messaging shift we're making in our business as well. And I can't wait to dive into that, but last certainly, but not least, Diane Mayor, I'm really excited to talk about your pivot specifically with podcast, but also seeing echoes of it in your entire business. So tell us, give us the background. What are you pivoting from and where are you now?

Diane Mayor (09:05):
Yeah, so I'm predominantly pivoting a piece of my essentially marketing, but a piece of my business strategy. So I had coffee and converse for three and a half years, or 255 episodes, and it was a weekly mix of solo and guest episodes. And I have pivoted into a daily show, which is really geared to giving you one strategic idea to think about every single day in your business. What I was finding was because I'd been in coffee and converse for so long, I had grown up in my business, but also my listener had grown up in their business. And so it wasn't really a space to bring a framework anymore and wasn't, I wasn't getting enough juicy ideas. And what I really wanted to facilitate was my busy, ideal listener who didn't have time for CEO time, but still wanted to be strategic in their business. So the five minute strategist was born, but I will say it was born incredibly slowly. So the idea of it happening was probably nine months before it actually happened. And as of recording this, it's been about two weeks. So I'm still in that very freshly pivoted space versus the other two. So it's all very fresh for me.

Andréa Jones (10:30):
And I'm curious, as someone who is a business strategist, how has this pivot changed your business model at all? Because it sounds like it's moving towards you really sitting in the expert seat because the five minute convos is all you, whereas before you had other voices on the show,

Diane Mayor (10:49):
It's all me and it's all me every single day. You don't get to have an off day. So for me, I think as a business strategist, when I think of a pivot, I need to see the entire picture first. And I think that's why it took me so long from something isn't sitting here and we need to get somewhere else to figuring out what that something else was. And I think this is one of the problems we see with pivots is people think, oh, I'm going to pivot, and the next day they've pivoted and you're like, probably going to have some regrets there. So for me, I really wanted to see where does my podcast fit into the ecosystem, and then where am I driving that to? What does my offer look like, how does my podcast ideas support that? And then where am I driving people to my podcast? Where do people come to my podcast and where do they go next? What does the whole customer journey look like? Before I decided on anything, the concept, the name, the cover art, all the stuff you actually think about came lost. All the strategy came first.

Andréa Jones (11:47):
Yeah. Okay. This is such a good transition into my next question, which is for everyone, thank you for teeing me up. So for a little bit of context, this is part three in our series. So if y'all have been listening with me here that Mindful Marketing is a name, domain name that I've owned since 2020. So four years. I have had having this pivot idea in the back of my head, and I never could quite figure out how to make it work in my business model. And that's what I'm hearing with each of these pivots is that the shift that we're making, whether it's in our marketing or in our business, really aligns with a larger plan and it has to align with a larger plan in order for it to make sense. Otherwise, we're just adding more work to our plate for funsies. So I'm curious, what was your plan for this pivot and how did it, well, you already answered how long it took, but I'm curious about some of the steps along the way, and I'll throw this back to you at Diane Mayor first to talk more about that pivot plan. You said it took nine months, so what are you doing in these nine months?

Diane Mayor (13:09):
I mean, to be clear, I wasn't planning for nine months. I think I had the idea at about, I was trying to think about what to do for my three year episode, and I realized, okay, I have no ideas and I'm an ideas person. And immediately to me, I was like, something is off now. I need to try and figure out what that is. And so initially I thought, oh, maybe I'll just pivot into a whole new show in three months time. And the more I dug into it, the less clear I was on the actual idea what was I trying to achieve? So where did it fit? What was it supposed to do? My offers needed to be updated, my branding needed to be updated. Everything I thought about added something to it. And so I think my plan was probably very market research heavy at the beginning.

I had some ideas of where I wanted it to go. And so I was asking listeners, I was asking peers. I was chatting in communities. I had some ideas where people were just like, I have no idea what you're talking about. I was like, okay, not that concept. So I think a lot of it was those initial steps that we like to gloss over. And then I would say probably, I probably made the call only in December and we're now in March. So I knew what the concept was, but then I didn't have a name. I knew I wanted to update my branding, so that had to happen before the podcast could happen. And so the last three, four months is the real plan, whereas I would say the first few were more the concept and the idea sitting at the back of my head, kind of like yours, that sat there for a while. It just needs to percolate for a while.

Andréa Jones (14:48):
Yeah. And it sounds like there was a key moment for you too, after having conversations where things really clicked into place. Diann Wingert, was there a key moment for you in your planning process where as you're going through and you're thinking about, okay, here are the next steps, or even just conceptualizing the moment, was there a key moment for you where you're like, ah, now I feel like I'm going in the right direction?

Diann Wingert (15:13):
The most important thing I decided about this pivot, because I have pivoted many, many times in business and in life, was that I was not going to rush myself, and that I was going to make decisions through a combination of information and intuition. Because usually historically, I'm a quick decider and a quick actor, but not always with desirable results. So this time I thought, I'm going to put the word out to people in my community. I engage with my email list, I put the word out through the podcast, I engaged with even a couple of the people on this call in other formats, and I just kept removing what had become clear that I didn't want. I think it was a process of elimination rather than a Aha, this is it. I would love that. That's so much more sexy and exciting and brag worthy.

But for me, it was more like, no, that's not it. That's not it. And I almost think of it like a big gift bag with lots and lots and lots of tissue in it, and then the prize is at the bottom, and I just kept pulling out tissue. Nope, nope, nope. And I started getting honed in, honed in, honed in, and I started issuing messages that were more aligned with where I thought I was going as little trial balloons. And those seem to be ones that I had people in my audience saying, was this for me? Were you thinking of me when you said this, when you recorded this, when you released this? And I'm like, we're getting warmer. But it's been a process of iteration. It would've been so great to have. I woke up one morning and there it was my future just waiting for me to step onto the path. No, that's not my case. And it doesn't sound like it is for most people.

Andréa Jones (17:03):
No, and I think it's important to talk about that because we want it to be, oh, we so desperately want to just wake up one morning and go, aha, I found it. But it often is a lot of, I love what you said about figuring out what it isn't. We're figuring out what, Nope, that's not it. That's not it. And I think that is a process that a lot of us go through. And I'm curious, Jamar, if you found this with the agency. So as someone who runs an agency, anytime someone's like, yeah, I close the agency to focus on consulting. I'm like, oh, that sounds amazing. The agency is a lot of work. I love my job, I love what I do, and also I spend more time managing people than strategizing. So if you don't like managing people, don't start an agency what you'll spend your days doing. And so I totally relate to that. And I'm curious about your pivot plan. What was it like to move from agency to consulting? And then now I believe you have a membership all about low lift marketing. So what was the plan and the timeline as you went through those changes?

Jamar Diggs (18:07):
So it all started, I want to say in August. So let's just think back about six or seven months ago because that's when I started making these small changes. At that time, I already kind of told myself, I am not taking on any more management clients. The girls that are here can stay. You know what I'm saying? I'll do it. It's cool. I like them. They like me. Why give them up? You know what I'm saying? If they're good, I'm good. And so the ones that left are gone. I ended up just kind of focusing more in my expertise, my frameworks. So I really wanted to figure out what is the messaging that I need to have, right? And I've done all of this discovery. I've made these offers. It is so funny because the pivot, I made it feel like it was this huge thing that I needed to change everything and that things are going to be different. I'm going to be calling in, I don't know, these higher quality clients or whatever, as if my clients that came in were not quality, which is not true. They were great.

But I did all of this. I did all of this changing to where now I realized that really it was just the agency, like how you said, I didn't want to really manage people. I wanted to probably have an assistant that was self-sufficient and myself, and I can just keep on being the talent, keep on being the strategist. You know what I'm saying? I love being that partner for people. It's just so great. And so what I had realized was that I wanted to get back to that quickly. And so I was thinking, I want to expand my impact. I wanted to create a way that I can get people introduced into my world a lot more easier, whether they stay for a month or six months or whatever. I was like, well, let's do this membership. I've had all of this collection of things, which is why I love every experience that I've had with the agency.

I have all these processes and all this stuff. Now, I was a process queen, honey, so it wasn't like things were just burning down and I didn't have things. So I was like, you know what? I bet business owners would love this stuff that I had in this agency. And so I had a template shop already, and I just created this membership as a resource for someone to just get introduced into my ecosystem. And to this day, I still have YouTube intensives and done for you YouTube strategies, which I love. And I've just been focusing up on those. And so this whole time I was thinking that it had to be something big and something crazy changing, and I had those things and nobody wanted them. Or maybe it was not that no one wanted them, maybe it just didn't align. I was trying to overcompensate for my change when really it was just the messaging tweak.

It was just that tweak in messaging. I had the things that my clients wanted. It was just how do I get the right people at the level that I want that saw marketing at the way that I saw marketing? And so that was kind of my plan, essentially was to keep the clients that are happy, good, keep things going. If I can do it by myself, which I can, I have the systems, the process and stuff like that, I can. But as I was moving forward and I was working on my frameworks with other consultants to get things out of my head and onto paper, doing my website rebrand and my branding rebrand, I did all these things because I needed to fit. I felt like I needed to my messaging and the look of my brand, I wanted to elevate it because that was important to me.

For most people, it all depends on what motivates you, what makes you feel good to actually give your 100% to this new version of your business. And for me was I've always been the person to where I love client led decisions or I want people to feel like they have everything that they need to know about working with me on my website. There is no, we don't got to be talking in the dms all the time. I mean, my God. So for me to feel really good about this transition, I needed to have my website up to date with the new messaging and branding to make people feel like they knew what they were getting from me.

Andréa Jones (23:09):
Yes, that's something I've noticed with all of us, is that in the entire pivot process, there's been a lot of communication, not only internally with ourselves as we're discovering what this new pivot is, but also with the people who we're taking along on the pivot. Every single one of you have talked about talking to clients and customers, sharing new offers with your people, teasing things out a little bit to see how they resonate. And I think that's an important thing to do as we're going through this. It can be very easy to have the best idea in head, and there's spend all this time crafting it and just push out to the world and realize this isn't what people needed or wanted. And so I love that with each of the plans, with each of the moments that we're pivoting, there has been communication with our community along the way. So we're going to take a quick break. When we get back, I want to talk about the challenges, lessons learned and wins that we've had in our pivots. We'll get into that when we get back.

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Okay, we're back. Let's talk about some of the challenges and lessons learned in this pivoting process because, oh, boy, am I learning lessons. One that I'm currently learning is that, oh, for some reason, recording podcast episodes when you're nine months pregnant is challenging. Who knew? Who knew? And so this is a lesson learned, but similar to Diane Mayor, is that I had episode 300 plotted out. It just so happens that that episode 300 is also a week and a half after I have a baby. So with this pivot, I decided to put it on episode 300 a couple months ago when I was in the glowy second trimester where you have all the energy. And now that I'm here, I'm like, oh, this is tough. This is really tough, and I'm so excited to be on the other side of this. So I'm curious about some of the challenges or lessons learned that you've had as you've gone through your pivot where you can look back and go, if I could do that again differently, I would. So let's go to Diane Mayor first. You're just on the other side. Two weeks into this new podcast, what have you learned?

Diane Mayor (26:37):
Well, I think it's still teaching me the same lesson. So I think for me, the biggest challenge that I had through this whole process was patience. I'm the kind of person who, I have an idea and I want to implement it, and I want to see if it works, and I'm super excited about it. And there have been, when you can see the whole strategy, you can see how many moving pieces need to happen and which domino needs to fall and hit the next domino and the next domino before you can think about what will I call my show or what does my cover art look like, or which photo shall I use? There's so much more that has to go. And I'm finding, even coming out the other side of it, I'm like, Ooh, these are the 20 ways I can repurpose an episode. And I have to be like, you've transitioned into a daily show. Step one, produce a daily show for a month. Step two, add the next thing. So really that allowing myself some grace and that it doesn't all have to be done by next Monday. That isn't a tech, this is complete kind of moment. And I think my probably biggest lesson along the way was there comes a point where you have to stop asking other people's opinions.

So you start off with all this market research and you get a lot of feedback, and you're asking people what they think about the graphic and what they think about the colors and what they think about the concept and 50 50, 50 50, 50 50. So you don't actually get any input other than none of your options are terrible. But there comes a point where you have to make a decision and understand that nothing is permanent, but put it out there, get some data, and then you can adjust based on data, not on your best business mate's opinion of which photo you've used in your cover arts.

Andréa Jones (28:28):
How do we know?

Diane Mayor (28:28):
Yes, lots of input.

Andréa Jones (28:30):
How do we know when that moment is?

Diane Mayor (28:33):
For me, it was when I got irritated that somebody was giving me feedback. I felt like I had moved past that decision, and then people were still giving me input in it. And you just kind of have to go, thank you so much, moving swiftly along or say, this is the one I've chosen. I'm not seeking input right now. I said to a few people, they were like, oh, what's the final one? And cover art is very subjective, and I sent it to a few people and I said, this is the final version. Thanks for your support. I don't need any input. I just put it out there, not in a rude way or anything, but I didn't want to hear, oh, if you tweak this letter or if you change this color, because you can input yourself into a state of not getting anything done. So I think those were my two is allowing myself some grace and then knowing when I had made a decision in stopping, asking for further input,

Andréa Jones (29:27):
Yes, I so relate to this because I just recently had this, and I didn't realize it was the irritation underneath it all that I was like, oh, no, I've already decided. Thank you very much. You've put that into new perspective for me. Look, here I am learning as well in the middle of my pivot, so I want to go to Jamar next. When you think about the challenges you've had through this pivot, what has come up? What lessons have you learned along the way?

Jamar Diggs (29:56):
Yeah, so I want to also just piggyback and say I too am not open to unsolicited feedback. If I say, this is the thing, baby, that does not mean for you to give more feedback. That window has closed. Sorry. Okay. But

Diane Mayor (30:15):
We're about to be non friends. If you tell me anything different other than you love it,

Jamar Diggs (30:20):
Oh my gosh. But no. One of my lessons, the biggest lesson is that, and I've always had this issue or this challenge in any iteration of my business, is that I tend to not trust myself, which is so crazy. People see me on the internet and they're like, oh my God, Jamar, you're so fun and vibey and whatever. But girl, back behind the scenes, I'm over here asking everybody, what should I do? What should I do? What do you think about this? What you think about that? Oh my God, oh my God, I'm dying and felt this pivot because I was so unsure, not unsure about the pivot, but what should my next step be?

And I think I had to, my lesson was, girl, don't nobody know what the hell they are doing. Stop asking these goddamn people. Sorry, girl. I'm asking these people what you should do. Everybody is going to have an opinion, but that doesn't mean that you have to move forward with that, right? And so during the beginning of this pivot, I heard from even valued friends that I really do trust that want nothing but the best for me, but at the end of the day, I have to feel good about which offer I put out, and do I really think this offer is the thing that is going to set me up for success? And so I had these offers. I was like, what is this thing that I said that I'll sell? This is stupid why I have this thing. It was so funny. I had this whole plan, and if you don't mind me sharing what my plan, yeah, go for.

It was like I was going to have people come in to this one offer. They do a, I don't know, some kind of strategy thing with me. And then after that, they get put into this secondary little mastermind group thing where they can, and I'm like, girl, how am I going to get people to get to that when I just open up a membership? I'm trying to get people to do the membership, what is happening? And it was stuff that I talked through on, I literally hired people to help me with this, and they helped me. It felt good in the moment, but then I was like, Jamar, let's be for real. And so at the end of the day, I hired these people, and then I was like, no, no, no. Listen to myself. What do I really want? And that was the best decision I had ever made because if I had kept it the way that it was, I would've been broke, evicted out of my damn apartment, honey.

I was like, what is going on? The sales are not coming. I said, F this. We are changing this up. And ever since I changed it to this very simple, simple, whatever people call it, alpha ladder, value, ladder, whatever, I have been getting inquiries, people working with me. It's great over here. I love it. At the end of the day, I knew what the transformation was or what it needed to be. If I would just listen to my people and listen to people as I'm having these sales conversations with them, and then change off of that, I was set up for success. I didn't really need to listen to these people.

Or if you're like me where you have to fail first to learn, maybe you did. And that was my lesson. I was like, oh my gosh, I am actually really good at what I do. I'm really good at thinking at what my business needs to best get the results that I want to make, the money that I want to have, the freedom that I really want. And my lesson was like, believe in yourself. Even when you're pivoting, even when you don't really know what the next 30 days is going to be, you will figure it out because you are the only person who has all of the data. You are the only person who knows who you're selling to the most, right? Even if you want to have a more elevated audience, that audience comes from somewhere. That audience comes from all the work that you've put in, you have the data. No one else is going to come in and be able to tell you what you should do. And it be 100% right. Everyone always have to tweak it. So you either pay someone to tweak it or honey, you got the answers all in you yourself.

Andréa Jones (35:17):
Another check for intuition. I mean, Diane, Mary, you said that at some point you have stopped listening to other people. What I'm hearing from you too, even hiring the experts, the strategists, they can only work with so much information. And I'm going to guess, Diann Wingert, since yours is information and intuition. I'm going to guess your lessons learned along the way, have something to do with that. But I would love to hear more about what are the bumps that you ran into and are still running into because you're currently pivoting?

Diann Wingert (35:49):
Yes, you've seen my head nodding continuously. I'm literally giving myself whiplash here because every single thing that the other Diane and Jamar have been saying is exactly my experience. I am not a patient person by nature. I'm also not a person who typically asks other people what I should do. But going through a pivot, it really gets you in touch with what I think all human beings experience during any time of transition in life, not just business, fear, uncertainty and doubt. I did a podcast episode on this, and I called it fud, fear, uncertainty, and Doubt because you're in a change process, you know, want to change. You've made the decision to change. But that's the easy part. The mechanics of it, how long it's going to take, how it's going to look at the end, we don't know. And we can get maybe some guidance, maybe some support, maybe some accountability partnership from other people.

But at the end of the day, it's going to take how long it takes. It's going to be as painful as it needs to be. It is your own personal evolution. And I think most of us, I would a hundred percent agree with actually both of the other guests. You kind of have to get to a point where you are so sick of yourself that it just somehow breaks you through to what you've probably always known deep down, but you haven't quite accessed yet. And part of the problem, as Jamar said, is that we don't think we can do this by ourself. We know how we got to where we are, but how do we get to the next place? Honey, you've been getting from one place to the next your whole damn life. This is not new. You have done every single thing for the first time at some time, and you had fear, uncertainty, and doubt.

So I really had to take a much bigger dose of my own fricking medicine because I am so good at helping other people through transitions. Sometimes I would send out some information and then people would talk, and then I realized that is not helpful because you either weren't ready to hear it or you just thought, well, I've been talking about it to myself. I better say something. And then they're like, oh, when's it going to happen? I'm like, whoa, whoa, whoa. Back off. Why did you engage them if you don't want to hear it? And it's kind of like, I think so much of this is our own discomfort with tolerating uncertainty, with tolerating things that aren't firm. I've been practicing meditation for many, many years, and I really had to double down on my meditation practice because that more than any other thing in my life has helped me not get comfortable with, to be clear tolerate my own experience of being in what I call the in-between I'm not where I was. I'm not where I'm going. I'm in the in-between, I don't know how long I'm going to be here, but I have been here so many times. I went from being a therapist to being a coach. I went from being married to divorce. I went from being a single mom to remarrying at 50. I've been through many transitions, and this is just the latest one. And so I think as Jamar said, you get to the point where you realize, I know, and I feel like it's right around the corner.

Andréa Jones (39:34):
Yeah. I think that period of knowing is also challenging as someone who's also not a patient person. The second I knew where I was going, I wanted it to happen immediately. Exactly. Why aren't we there already? And that to me is actually just as uncomfortable as not knowing where to go. So true. And so I relate to everything that everyone is saying, and this is why I wanted to have this conversation, because I feel like there are a lot of business owners, and especially in marketing and social media, there's a glossy finish of here's the thing that we are releasing, or even let's pretend it's not happening while it's happening, which is where I'm currently, one of my friends texted me the other day and was like, oh, you must be feeling great. I watch all your social. I was like, oh, no. That was filmed months ago.

I feel terrible. So the glossy finish on social media, yep, it's there. My team's running it. It's beautiful. And the realities behind the scenes don't often match that. So I love that. We talked a lot about some of those challenges that we are all experiencing along the way, and a lot of it has to do with waiting and leaning into our intuition. But I'd also love to explore some of the wins that we've had as we're pivoting. Because one of the things that I have thoroughly enjoyed about this process is once I knew where I was going in my head, I was like, oh, this is where I was going the entire time. I just didn't know that this is where I was going the entire time. Even rebrand something simple, rebranding the podcast to me, it's a rebrand in name only. There are some concepts like this round table that's different, but my beliefs about marketing and social media have actually already been here.

And so that's the biggest win for me, is just simply changing the name of it, just named what I was currently already doing. And I had a client who came in, a new client came in, she saw my email series where I was thinking out loud about this whole pivot and shift, and she was like, as soon as I saw the word mindful marketing, I thought, ah, this is the company I want to work with. And I was like, oh. So it helps other people understand it. And that was a huge win for me in this pivot process, was having someone confirm and decide to work with us because of how I showed up during the process. So I'll leave this as an open question. What's a win that you've had as you are pivoting your business, your marketing, et cetera?

Jamar Diggs (42:18):
I would love to go first. I have two to share, if you don't mind. The first one is that in this whole pivot, it's been so great to get back to the things that make me really excited. Well, actually normally when I had the agency, I never had time to do my own marketing, which I know is like a faux pa. I know, I know. But now that I have kind of released that and I have so much, I have room to do strategy for my own business, and it really lights me up inside to where I get excited to film my YouTube videos. Now I just have so many ideas. I'm like, oh my gosh, what else can I do? And so I have a more excitement to serve my community because I am leaning into this pivot that is so much more aligned to what I really want for myself and my business and my impact. And because I have been doing that going into the second win, is that just recently I've been able to sign a Fortune 500 company to work with.

Guess when we met with them, everything that they were saying that they really wanted to move in with their marketing was, oh my gosh, everything that's in my messaging. And so it was so cool to see that all the work that I did is for those elevated brands and things like that, and how they wanted more of an integrated marketing approach. They're taking a more holistic approach to marketing. They want to have it be more customer centric. And I was like, oh my God, word for word in my document, this is great. I should talk about this even more. And so it was just such a win and such a great validating moment, these two things that now I'm able to, I just feel like I'm going in the right direction.

Andréa Jones (44:23):
Yes, beautiful. I love hearing wins. Love it. Who's next?

Diane Mayor (44:27):
I can go. So I think for me, and this is going to be super coming from a business strategist, but I think because I spent so much time on the strategy that making the pivot, everything is just super clear. Not just for the thing that I pivoted because I didn't pivot my business. I just pivoted a piece of my business, and that has made my customer journey clear, my delivery journey clear. I know exactly what each element of my business is bringing to the table. So when I have to make a decision, I can really clearly look at each element and go, how is it impacted? Does that work? Or what's the next step? How do I bring this in? So I think having spent all of that time up front, getting really clear has really helped the rest of my business. Yes, it's helped me to see the path through my business for somebody external.

Andréa Jones (45:22):
Yes. No, I'm not surprised that that's your answer. It makes perfect sense to me, and I love hearing that. I think even just early days of pivoting for me, the lack of clarity, like Dan Winger said, is just so uncomfy that when you finally do it and all the pieces start clicking into place, yes, there is a moment of relief. I love that. Diann Wingert, what are your wins as you're still pivoting.

Diann Wingert (45:51):
A couple of them. One is that as I was toying with why am I only marketing to women? I work with men. I work with gender non-conforming individuals. I work with all kinds of people, but they're not going to find that out if I don't make that clear. So as I was kind of noodling on that and thinking, okay, I'm going to do this, I got a message from someone who said, I listen to your podcast. I follow your newsletter. I am constantly checking out everything that you do, and would you consider working with me because I'm a man. And it was so cute

Because I thought, would I, so this individual turned out to be an absolute ideal client, and I thought, what a missed opportunity that he actually felt he had to apologize for being male. So I thought, I'm doing this. So it was the clarity that came from that. And actually in looking back over my history, some of my very best clients have always been men, but it was a confirmation. And the other one, which I think is an even bigger one, I was interacting in another community and talking about the pivot and talking about where I've been and where I'm going, and with a lot of clarity around the things that I have figured out. And someone in that community said, I went to your website. It is not aligned with what you're talking about now. And I would love for us to have a discovery call about you and I working together. I'm a rebranding strategist and graphic designer. I met with this person, totally fell in love, and we start the first week of April, and I've never worked with a professional to design my website or my branding before. I've always just kind of figured it out myself. So I'm going to get a professional rebrand and I'm sure a delightful collaboration out of the process.

Andréa Jones (47:44):
That's beautiful. I love that. I've been thinking a lot about gendered language and marketing. I think that needs to be a whole nother podcast because while my marketing definitely has a lot of feminine elements, I've struggled with the assumption of the gender of the folks that I work with. And it's like, I mean, as far as the list of qualifications of my ideal clients, gender is not even on the list for me. But there is this assumption in how we work with people, and even some of the groups that we're in. It's definitely an interesting conversation. That is probably another podcast episode. But I love this clarity for you on both who you're working with and finding someone to collaborate with you, which it just feels magical. Right? Love that. So as we move into this next phase, I would love for all of you to, we'll go around the room, share how people can connect with you, and give us one little kernel of an idea of what the future holds for you and your business. Let's start with Diane Mayor. Tell us where people can connect with you and what the future holds for your business.

Diane Mayor (48:54):
So I am on all the socials at Diane Mayor. It's M-A-Y-O-R. So I'm pretty easy to find unusual spelling. Obviously. The place I would love you to go is to the five minute strategist. Have a listen to the new podcast. I'm open to feedback, suggestions, ideas. Tell me what you liked, and if you really love it and want to leave me reviews, we can be BFFs. I think for me, with the Pivot, the next phase is trying to work out how I can do something collaborative with it. Five minutes doesn't lend itself to a guest interview, but as people who know me know, I've always got an unusual idea up my sleeve. So I think that will probably be phase two, but I'm forcing myself to think about that from a May, June kind of timeline to allow myself that patience to let all the other pieces click into place first.

Andréa Jones (49:43):
Beautiful. Love it. We'll put the podcast in the show notes. Y'all go check it out and see what that feature looks like. Jamar, over to you. Where can people connect with you and what's next for you and your business?

Jamar Diggs (49:54):
So you can find me at Jamar Diggs on everywhere. Threads, YouTube, Instagram, every place that you can find me, you will not regret it. It's just, look, I'm just telling you, you'll come from the podcast and you'll just stay for the vibes. Okay, but what's next for me? I honestly, being on the other side of this pivot, I think I don't do a good enough job at living in the success, living in the, and so I know your question was like, what's next? What are you doing now? I'm like, girl, I am enjoying this moment. You know what I'm saying? I'm like, girl, can I just enjoy this moment first? Oh my God. No, I'm kidding. But yeah, I really want to just keep this going and keep on repeating. That's really a goal of mine. My goal is to be here for a long time and good time. You know what I'm saying? My goal. So really it's just keeping it going, keeping it staying, making these tweaks to making sure that I am giving the best product possible. The messaging is good. Really, the messaging is already good. It's really just positioning. So focusing up on my positioning even more with larger brands while still helping my small business clients as well. So that's really what my goal is, just maintaining and repeating the success that I've been able to get.

Andréa Jones (51:42):
Beautiful. Love it. Diann Wingert, tell us, what does the future hold for your business?

Diann Wingert (51:46):
I need to get to the end of this pivot because everything is going to be changing. The podcast is changing. My signature framework is changing. My offers are changing. I'm working my way all the way through the business, so I need to get all the way to the end of it. And I have no doubt that I will. I'm literally doing one thing at a time and making a lot of progress on that. And as for where people can find me, I would love it if you would check out The Driven Woman Entrepreneur Podcast, because even though its name and show art will be changing, it'll still be me.

Andréa Jones (52:22):
Yes, definitely check out the podcast. I'll put the links to everything we talked about today in our show notes. You can find those at slash 300 episode 300. This is part three. Thank you so much for listening to this round table discussion and hanging out with us today. Stay tuned. We've got more awesome things coming down the pipeline for the podcast. I'll see you in the next episode. Bye.