How To…. Become the CEO of Your Career with Tammy Alvarez

Kathi: Hi everyone, we're back. I'm with Tammy Alvarez. She is the CEO of the Career Winners Circle. And today we're going to talk about winning and keeping your sanity at the same time. And Tammy is a good case in point of how you can create whatever kind of reality you want. So let's jump into it. And thanks, Tammy, for coming on the show.

Tammy: Thank you so much for having me. I've been looking forward to this.

Kathi: This is great. Yeah, I'm excited. Okay, so let's talk about your journey. I know you've landed now in Mexico City, which I'm totally intrigued about, after spending time in Belize, which is one of my favorite countries in the world. So talk to me about the journey. How did you move from Wall Street to what you're doing right now?

Tammy: Yeah, it's a fun journey, and it's one that either people think is terrifying or they want to do, depending on what side of that coin you're on. I spent my career on Wall Street, and I became a C-suite executive managing 2,000 people in 54 countries. It was just crazy, and I loved it, and it thrived. My career thrived, and I was fortified and just stepped into every day with joy, until I didn't. And I just remember that moment where it started to go from invigorating to soul-crushing. And once I hit that line, it just free fell, and I really started to have that apathetic view. And that was never like me. So at the height of my career, where everybody thought, okay, you've made it, the big office, the big fancy apartment, all those things, I decided that this no longer served me. And so about six years ago I cashed out of Wall Street. I moved to a tropical island in Central America, in Belize, and lived on that tropical island for five years and started this coaching business. I had no idea what I was doing, right? You can lead a big corporate, but entrepreneurship was a whole new world for me. So I'm excited to share all the mistakes and all the foibles that I've made. But then after five years in Belize, we really loved everything, but we were ready for urban again. I'm a New York City girl, and so we did some country shopping, and now we are here in Mexico City for as long as we want to be.

It started to go from invigorating to soul-crushing.

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Kathi: I think it's fantastic that you went to the extreme. You left all the hubbub. You're like, I've got to add space and debrief and defunk my life, and let's go to an island and just cast things away. But then you're like, I gotta do something. I'm gonna launch a business. So did you find that challenging with internet and whatnot? Did you do it over Zoom, or what happened?

Tammy: Yeah. So I did this before anyone knew what Zoom was. In the New York metro area, and a coaching business, people were like, you can't do this remotely. What's Zoom? And I was like, yes, I can, and Google it, you'll figure it out. And so it was an interesting experience, because on one hand I had the freedom from all of the American culture of more.

Kathi: Yeah.

Tammy: And I had the freedom from keeping up with the Joneses and my expensive apartment and the fancy shoes and the handbags and the lifestyle. So my expenses plummeted, which was a great time to start a business. Yet I was disconnected now. I wasn't there at the pulse of what was happening every day. And starting a business, for everyone who's done that, which is your audience, you know how hard it is. And I think some of the bigger challenges for me were going from a high-pressure corporate role to being alone, where no one even knew or cared that I existed. It was so weird. I'm like, where's all my meetings? Where's the line outside my door? And so I felt very lonely. And I'm also, the magpie is my spirit animal. I love shiny objects. I will chase all of them. And so I spent a lot of the beginning of my entrepreneurial journey just going down rabbit holes that didn't serve me, until I finally figured it out with some help. So being on that tropical island really gave me a break that I didn't know I needed. It gave me a place to center and find balance, because I never had balance. Even when I was raising a family, it was always work first. So almost giving myself the permission to go scuba diving in the morning before work felt really weird. I'm like, I shouldn't be doing this. It's not how it's done. And I found a way to grow a thriving practice while working about 30 hours a week. And so for me it was a really fun journey, because socially it's very different and the pace is different. But I need to be challenged, and that's why I left my corporate career, because I was no longer challenged. So I'm stepping into this environment where I had no idea what I was doing. And I purposely went to a business-to-consumer model, because I promised myself, for the first three years, you're only selling B2C. Because I knew if I went back and sold B2B coaching services or consulting, I'd be right back in the environment that I left, because I was still addicted to it and I needed to detox. And so that was quite a journey, trying to learn all that.

Kathi: I'm sure. I'm sure. But intuitively you knew that you had to debrief and defunk. I applaud you on that. When I had 10 months off to reinvent myself, it took me three months to even settle into: I'm not in guilt anymore. I don't have to do this thing. I'm not guilty for doing this. It's like, oh, okay, there is no real accountability. But I should be figuring it out, right?

Tammy: Busy.

Kathi: Yeah. My husband finally said, at I think month two and a half, "If you don't settle down, you take the job working for the man and I'll take the year off, because you're going to be reinventing yourself right now." And I'm like, "Oh, okay." That was my wake-up call. My first question for you was, how did you land that first client? How did you find clients on a little old island in Belize to do what you wanted to do with your new career?

Tammy: All of my clients are in the US and the UK, right? So there were no clients for me in Belize. It's a tropical island with hospitality, scuba diving and amazing palapa bars everywhere. It's a vacation place. It's got a big expat community, but they're all retired. So there were no clients for me in Belize. So I worked my network, and I continued to listen to all the experts, right? I didn't know what a sales funnel was. I had no idea what an email campaign was, or email automation. None of these things were things that I was aware of. And so I'm listening to all the big names, and I'm trying to do all the things that they say to do, and it is a disaster, because all of those things only work if you have a million-dollar advertising budget. They forget to tell you that part. And so eventually I found some really good advisers that were just a few steps ahead of me in terms of how things really got done.

Kathi: Yeah.

Tammy: And I think there were two key moments where I really started to focus on client acquisition. The first one was, I had a very good adviser who was also on the island, but retired. He had sold several companies, sat on boards. We would have a margarita and talk about the business, and he was a very good adviser. And I was chasing all the things, and he sat me down. He's like, "Tammy, without revenue, you don't have a company. This is the only thing you should be focused on." Because I want to write a book, I want to do all these things. He's like, "You need money." And I'm like, that's probably a good point. Now, Wall Street girl, you'd think I would know this. And I spent so much time completely disassociating everything I ever knew, because I wanted a fresh start, that I forgot to bring some of the common-sense things in with me. So that was a nice wake-up call: you've got no other focus in your whole life for the next three years other than to generate income and make this a viable company. And so then I started to look at, how do I do that? Where do I find my tribe? And the reality is my tribe found me. I was a transformation…

Tammy, without revenue, you don't have a company.

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Kathi: Something you said that was very interesting to me is that you found advisers that were just a few steps above you. You don't go for the multimillion-dollar gurus to advise you. I totally think that this is true. You have people who are just a little bit ahead of you, because they can relate to where you are, and they can give you more practical, applicable, actionable tips.

Tammy: Yeah. And the pain is still fresh, right?

Kathi: And they're gonna get real.

Tammy: Yeah. They're gonna get real with you. They're gonna say, "No, no, it doesn't work that way."

Kathi: Okay.

Tammy: Thank you for stopping me on that. And then I think the other piece of advice that I got that really helped is, because my business found me. I was a transformation expert on Wall Street. So when there was crisis and everyone was running out of the building, me and my teams were running in, and I loved it. I love change, transformation. Fortunately, in financial services, it's always a mess, right? So there's always something to do. And I thought that's what I'd coach on, because most people suck at change and transformation. So I'm like, great business opportunity. But the other issue with that, and this is where I started to learn how to lean into being smart and thinking about things differently, is that yes, I'm a transformation expert and have a lot of value to offer, but I also said I'm only doing business to consumer. And what I didn't think to check on is, are individuals willing to self-fund their leadership development to become better transformation leaders? The answer to that was no, they're not. Companies will pay for it, but as an individual they will not. And so my business started to find me as I was talking to people, and they're like, "I don't need that, but I am in a career I hate, and I am stuck in the ivory tower in the soul-crushing grind, and I want to know how I can live on a tropical island like you." And while they didn't necessarily mean that literally, it was very much part of an accidental twist in my business: helping mid- to senior-level leaders get out of the soul-crushing grind and pivot into something that they love, without having to give up everything that they've worked so hard for. And so that found me. So I think it's listening to what the needs are versus what you think you're going to do. I think every entrepreneur I've ever coached is not doing what they thought they'd be doing, right? And it's important to know that.

Kathi: What I think is important about what you said is that it's back to the avatar. I took so much training on who's your avatar, right? Your avatar is you.

Tammy: Yes.

Kathi: The people who want to hire you are you. They were you. They want to not be like you were. They want to transform like you wanted to. That's where it's at. And I think that we spend so much time… I wasted so many thousands of dollars trying to figure out avatar, and now it just comes down to the simple thing that my avatar is me. Your avatar is you. The people who need you are who you are, and they're like you.

Tammy: Well, it was funny, because I just had this conversation with our coaching team. We've got about seven coaches on the team now, and we were talking about their target market and all that stuff. Like, you're coaching you. So just go find people like you, because you like them, they'll like you back, and you're going to be able to close business much faster.

Kathi: Yeah, exactly. But you're not going to make a million dollars selling that online, so you can't say that out loud. It's just, don't blow your money on that kind of stuff. And I love the fact that you said we're chasing shiny objects. That's what we do as entrepreneurs when we launch. We're like, that guru, that guru, this is the answer, this is the answer. Let's put all those answers together. And I agree with you, they don't say, "Well, you need to have a big budget to do what we're going to say that you're going to do."

Tammy: Well, the other thing I got sucked into, and a good friend finally smacked me upside the head and said, "What are you doing?", is you look at the vanity metrics on social media. So this one has 17,000 likes, and this one has 30 comments. And you're like, okay, I need more. I need a bigger mailing list. I need more. I need more. And one of the friends and advisers that helped me get this stuff set up, she's like, "Why don't you spend time loving on the people you have instead of always worrying about getting more and being bigger?" And again, these things are so simple, but they were not obvious to me. Because you get sucked into, as a new entrepreneur, okay, what's everybody doing? Let me repeat a process that already works. And so when I started to lean into the community that wanted to be with me, instead of worrying about trying to attract all the ones that were just too busy to care or it's not the right time, then things started to really change for me.

Kathi: Yeah. This is a write-it-down moment, you guys. This is a write-it-down moment, right?

Tammy: Love the ones who love you. Love the ones who are following you, and just smother them in love. And it doesn't matter if there's only 20. Just love them, because then that 20 is going to turn to 30. It's going to turn into a hundred, and those types of things. And so that was really an important lesson for me to learn: to stop caring about what everyone else was doing and just lean into who I'm here to serve, and make sure that those experiences are epic.

It doesn't matter if there's only 20. Just love them, because then that 20 is going to turn to 30.

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Kathi: Yeah. Let's talk about one of your favorite client experiences. Tell me a story about someone.

Tammy: There's so many.

Kathi: I know. I know. It's funny.

Tammy: Yeah. Right. So yeah, shameless plug: I just wrote a book, and it's coming out in mid-January. So there's tons of my client stories in there. But I think my favorite stories… I've got this one client that's been with me for a bit. High ambition, high talent, and incredibly focused, and just an amazing leader. And she joined an organization in its earlier days. It just went from zero to explosion, and then they're going to go public, and she's part of that team, and then it falls apart. They don't go public. Everything just goes to hell in a handbasket, and she's leading through all of this adversity. And meanwhile, she's just getting potshots, and it's just all of these things. And so what's interesting to me, in terms of the work that I do with both my leadership and my entrepreneurial clients, is that people who have ambition are used to putting themselves out of their comfort zone.

Kathi: Yeah.

Tammy: But no one wins alone, and success is not linear. And so when you feel like you're ambitious and you're going for it, and then you get halfway there, but then somebody cuts you off at the knees and you've got to go back and try again. And we do that with our businesses too. And so it's helping them maintain perspective, right? Helping them with strategies that have worked for me in the past, because we do advisory and coaching. So it's a blend, instead of just asking a million questions and hoping they find the answer. And just helping them find that inner resilience, because that is the stuff that lasts, right? Tactics, situations, they change. We are always going to have challenges. And so it's trying to figure out, how do you get through that brick wall without giving yourself a massive concussion, and then using those skills over and over again.

Kathi: So did she want to transition out, or why did she…

Tammy: She didn't at first. And so she was just trying to survive the crazy, because she really bought into the mission of the organization. She loved the company, she loved the culture, she loved the clients. And so this company that she loved was also just sucking the life out of her. And she had a deep, deep sense of loyalty. And we can talk about misplaced loyalty in terms of corporate environments all day long, but that's not what this conversation is about. And so she was conflicted, like, I need to provide for my team. I need to leave a legacy. I need to make sure that they're going to be okay when I'm not here. And so we were on a two-year journey to help her through chaos, up, down and sideways, to be able to get to a point where she could finally say, "You guys are good." And three of her people moved into C-suite roles. So she was really able to be very, very purposeful in her values and in the things that were important to her, despite the personal sacrifices she was making, to be able to write her own chapter and to be able to say, yes, I want to do something different. And now she's on to doing really amazing things in a very different industry. But she wanted to make sure that the organization she loved so much was left in incredibly good shape. And so I think that's the journey, the wins, the losses, the tears, the laughter, all those things, as you're going through that with your clients and you're really helping them find their way, and then you see them come out on the other end, right? And she'd never taken a break. So once she left, which was earlier this year, she took the summer off and went to Greece and Italy, and she had an amazing time. And now she's back in New York, and she's working with private equity companies, helping manage their organizations as an operating partner, which is a totally different career, but using all the things that are her superpower.

Kathi: Right. Right. Yeah. I always think what you should be doing is stuff that comes natural to you. Whatever's natural to you, that I always say you can do asleep, standing on your head, that's your dharma. That's your gift. That's what you give back to the world, because that's actually what you were born to give. That becomes the easy. I think for anybody out there who's listening who's looking to reinvent, think about what do you naturally do? What's so easy for you? Like me, for you it's change, right? You're going to run into the fire. I'm probably going to run into the fire just because I want to have the thrills, right?

Tammy: Yeah. Adrenaline junkie.

Kathi: Totally. Yeah. Exactly.

Tammy: Exactly. And we love change and thrive, and some people hate it.

Kathi: But what can you do naturally? For those who are listening, standing on your head asleep, so to speak, that's just so easy and so effortless and just flows right off of you. That's what you do as you're reinventing yourself.

Tammy: And I also recommend that you take it one step further and focus on what energizes you.

Kathi: Yes.

Tammy: Right. Because there are things that come easy, that are easy and natural, and I also think there are things that light you up. And so what are the things that you can do for 12 hours a day and end the day more energized than when you started? As entrepreneurs, we do all of it until we get teams. And there are things like this I could do all day: coaching my coaches, coaching my clients. I love that stuff. That's energizing. Social media, the funny part, all the other things that go along with it, can I do them? Yes. Do they energize me? No. About two hours later, I'm just ready to throw pencils at the ceiling and spin around for a little while, right? And so I think that's the kind of stuff you delegate.

Kathi: Totally. Absolutely.

Tammy: Well, that's where Wall Street helped, because I was very fast to know the things I suck at and make sure I had people who loved those things. So that way we were in good shape with that. And I think a lot of people miss that part initially, because they're like, oh, I'm not making enough money yet, so I can't spend money. And it's that dichotomy of income versus spending it in the right ways to help you free up the time, so you can do the things that you are excellent at and that will make your business grow faster.

Kathi: Yeah. I just heard an amazing statistic from the Harvard Business journal, that if a company doesn't spend, I think it's $82,000 in the first three years of growing their business, they will most likely fail.

Tammy: Interesting.

Kathi: So there is an expenditure that you have to make. You just have to make sure that you're spending it in the right way. And like you said earlier, you think, "Oh, I can't delegate. I can't do this. I can't hire that." You can't not do that, right? So if you're underfunded, you've got to be able to delegate what you hate.

Tammy: Yes.

Kathi: Otherwise, you're going to get burned out.

Tammy: Well, and there's tons of resources. They don't all have to be high-priced, expensive local resources. Like, we got together through somebody on my team from the Philippines, right? I've got teammates that are all over the world. And so especially today, I think entrepreneurs have so many more available options in terms of time, cost and quality. And it's important to make sure that we review those and know what we have available, because we're the only engine that drives our business until it starts getting big enough. And that engine has got to be functioning at top speed.

Kathi: Right. Right. Yeah. And not sputtering for air or sputtering for gas, or just sputtering in general from burnout.

Tammy: Well, I was going to say, burnout is such a huge thing, not just for corporate but for entrepreneurs. And I think that's one of the things I'm most proud of, is that I've really been able to build a thriving company, and I don't think I've worked more than 30 hours a week since I started six years ago.

I don't think I've worked more than 30 hours a week since I started six years ago.

Kathi: Love it.

Tammy: And so it's not a superpower. It can be done. And I think one of the biggest things that I try and talk to my clients about is really having this experimental mindset, because nothing ever goes the way you think. And so if you continually experiment, say, "Okay, let's try this. What does this button do? Keep the things that work, tweak the things that were meh, and get rid of the things that didn't," and continue to do that cycle, then you're going to be able to grow your business much faster.

Kathi: Absolutely. That's really good advice as well. You're just a wealth of this information.

Tammy: Thank you.

Kathi: Okay. So obviously you're very well organized, because you're only working 30 hours a week on this amazing business. What's your favorite organizing hack or tactic? What do you use to keep yourself… what's your favorite hack?

Tammy: Yeah. So I am a tech freak, and yet I hate tech. I love the tools and toys, and I just don't have the superpowers to connect them together. But we automate everything, and I started doing that even when I was little, and that way it built as we go. So for example, and this is not an advertisement at all, we use Google Workspace as a team, and ClickUp is connected. Everything is integrated, and so you don't have to think about anything. It's just all there. In terms of our CRM, you pop on our website and you go in through a specific coach, one of our coaches, then we're going to know where you came from, and then you're going to automatically go into our email campaign under that coach. That's going to hit their CRM, so they know they've got a new client, and that's integrated with our portal. And so all of my software solutions are SaaS, right? And they're low cost. And so spending just a little bit of money to get all of these things to talk to each other saves me and my team, I can't even imagine how many hours, just in organization and communication. We're always in alignment and all of those things. So for me, it's all about the tech integration and using it to its fullest advantage.

Kathi: Yeah, things have to talk to each other, and they have to get along and play nicely. And as a professional organizer, that's something that I always discern: do you have two things competing in the background, fighting against each other? Do you have things that are half-baked? Half the time we go for the gadgets, bells and whistles, and then there's something half-baked in the background that's screwing up your other one that's really working, or you don't even know what's working, right? So I love Google Workspace. I think it's fantastic.

Tammy: Fantastic. Yeah. When it was more than just me, we started building teams, so we needed to have a shared space, and I just love the collaboration features. Nothing's perfect, right?

Kathi: But Mercury's in retrograde. Nothing works anyway, so you may as well figure that out, right? That's coming in December. I learned never to launch when Mercury's in retrograde. And I'm not an airy-fairy person, but I had definitely gotten my clock cleaned more than once trying to do some kind of launch during that time.

Tammy: Perfect time for closure. Time to wrap and close.

Kathi: Totally.

Tammy: And I think on a personal level, in terms of staying organized, I block my calendars for the things that are hardest, and I do them when I'm at my best. And so as I age, mornings are better for brain time. So the things that I hate, or the things that don't come naturally but that need to get done, that is the stuff that I will do first thing, while my brain is fresh, while I still have patience, and before the day gets going. So that's another way that I stay organized, just in terms of my own personal productivity.

Kathi: Yeah, you're following Mark Twain's advice: if you have to eat a frog, do it first thing in the morning.

Tammy: Exactly. Yes. Do it when you're fresh.

Kathi: Because I just got back from France. There's a lot of frogs there.

Tammy: But yeah, hopefully we won't be eating any frogs.

Kathi: No, no, don't do that. Okay. So just a couple more questions and then we'll wrap. If you had to look back and tell your 18-year-old self something, give her some little piece of advice, a nugget, a piece of gold, what would you tell her?

Tammy: I would tell my 18-year-old self that you are more than good enough just as you are. Growing up, we grew up poor. Long story short, parents split up. We ended up homeless, my mom and my sister and I, for a while. So I was always in this overachievement mode. And I didn't go to college until I was 40. I didn't get my degree till I was 40. So I started my professional career very differently. And so that informed… I just showed up different. I played different. I had high risks. And I had the imposter syndrome every day, because I didn't belong. I wasn't like everyone else. I wasn't as smart. I wasn't well traveled. I wasn't all the things. And so I spent my entire life thinking, I'm not enough, which made me try even harder to prove myself. And it worked in terms of outward success, but the inner turmoil of always feeling like I was less than… And it wasn't until later in my career where I had this epic moment where my boss finally told me, "You're here because you're not like everyone else. You're here because you're different." So I always looked at it as a concession, like, okay, I'm here even though I'm different. And it didn't occur to me until much later in my career that that was actually my competitive advantage.

Kathi: Yeah. I think our own unique self is our competitive advantage, always, on anything, especially as entrepreneurs.

Tammy: Well, that's what you trade on, right? You're trading on your uniqueness. You're trading on your perspectives, and either being the contrarian or having an innovation, whatever the case may be. It's that point of differentiation that defines the organization that we're trying to build and how we show up to serve the world.

Kathi: Exactly. And only you can be you, which is a great thing, because no one can be you. And so I don't even consider competition competition. I just love the diversity. That's why I have so many other pro organizers on this show. We all are so different, and we all do things a different way, and it's thrilling to me to see everybody bring their unique gifts to the world in the way that they bring it to the world. And back to the avatar: we will resonate with people who are like us anyhow. So who cares?

Tammy: Exactly. Exactly. And I always think, when I start to coach people, because sometimes in corporate they're like, should I start my own business? Shouldn't I? Those types of things. Every time someone feels like the market's too crowded, it's like, that's the perfect time to enter, because you know the market's established. If no one's doing it, then there's a high probability no one either needs it or wants it. So you're better off jumping into the melee and differentiating yourself. And let's face it, how many customers do we really need to be prosperous and successful and feel like we're making an impact? It's not millions.

Kathi: No.

Tammy: So just keep things in perspective and serve your market.

Kathi: Yeah. Especially when you're loving on them. When you're loving on them, they're going to grow and thrive, and it's all good, right?

Tammy: Yeah. I love that. Absolutely.

Kathi: Yeah. Okay. So I know that you have a valuable free resource for the people who are looking to maybe make a transition or just step up their business a little bit. What is it, Tammy, that you will offer?

Tammy: Okay. So we are offering today a copy of our Resiliency Roadmap. It's a step-by-step guide on how to really step into having the resilience you need as a business owner. And that's getting rid of all the inner junk in our head. That's being able to flex and adapt, and things like that. So we'll make sure that we have that link for you in our show notes.

Kathi: I love that. Yeah, absolutely. Put it down below and click on it. Is there anything that you could say verbally for people who are listening who might not have show notes? Do you have a URL?

Tammy: Sure. And in there you'll see the option to download that Resiliency Roadmap.

Kathi: Perfect. Perfect. All right. Well, is there anything that I forgot to ask you that we should have touched on? Anything in your brain that you're like…

Tammy: I love where the conversation's gone. I think we've really covered a lot of ground in a short period of time. I think the parting words that I want to leave with the audience is to really step into what lights you up. And we talked about that a little bit, because I think we get so bogged down in the stress of life, the stress of what's going on in the world, the rate of change. All of these things are just hitting us from all different angles, and sometimes it feels like you can't even come up for air. And so if you can put yourself in your little happy bubble and focus on the things that light you up, and the things that you can control as you're growing your business, without letting all of those external factors continue to drag you down and provide distractions and all of those things, I think both from a mental wellness perspective as well as from a business perspective, you're going to be much better off. Because there's just so much going on right now that can just destroy our will to persevere.

Kathi: Yeah. Yeah. I agree. Look for that spark of happiness and follow what lights you up. And the should-do, the have-to-do, the want-to-do, just get rid of all the dos.

Tammy: Get rid of all the doo-doo.

Kathi: That's it. And follow what lights you up. I think that's really, really good advice. Well, this has been a huge pleasure. I absolutely love speaking with people with different modalities. I am so excited that you're living in Mexico City and you're living the dream of what you want to do, and that you were able to reinvent yourself and do whatever the heck you want. Everybody, tap into Tammy's resource, because you know what? We can all do whatever we want to do. We just have to know that to be true.

Tammy: Yes.

Kathi: So download the resource, and that will help you move forward.

Tammy: Excellent. Well, thank you so much today.

Kathi: Absolutely. It's been a pleasure. Thank you so much, and we'll hopefully see you soon in Mexico City. It's on my list.

Tammy: Definitely come visit.

Kathi: You got it. Thanks again. Okay, take care. Bye.

Tammy: Bye. Bye.