Surviving the Side Hustle

Don't Give Up Everything, Just Change How You Work: A Guide to Career Transitions

• Coach Rob • Season 1 • Episode 87

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Ready to transform your professional life and love Mondays again? Tammy Alvarez, founder of the Career Winner Circle, takes us through her remarkable journey from commanding a 2,000-person team across 36 countries as a Wall Street executive to starting her thriving coaching business from a tropical island off Belize.

Tammy reveals the exact moment her corporate career became terminal — when she developed what she calls "I don't give a shit-itis" during yet another blame game in the boardroom. This candid revelation leads to powerful insights on finding your career sweet spot by focusing on what genuinely energizes you rather than just leveraging your marketable skills.

At the heart of Tammy's methodology are "the five lies" holding most professionals back from meaningful career changes. These deceptive beliefs — that industries don't hire outsiders, that career changes require sacrifice, that skills aren't transferable, that different means disadvantaged, and that companies will take care of you — keep talented people trapped in uninspiring roles. Her breakthrough realization that being different is actually a competitive advantage will resonate with anyone who's ever felt like an outsider.

For entrepreneurs and business owners, Tammy shares the game-changing strategy that increased her business's customer lifetime value by 40% — transforming from project-based to subscription-based service models. This isn't just theoretical advice; it's a proven approach that works across both B2B and B2C environments when properly implemented.

Looking ahead to 2025, she emphasizes the crucial need to embrace AI literacy ("you won't lose your job to AI, you'll lose it to people who know AI") and diversify income streams amid economic uncertainty. This forward-thinking guidance helps both employees and entrepreneurs prepare for whatever challenges lie ahead.

Connect with Tammy on LinkedIn or visit careerwinnercircle.com for a complimentary assessment that could change the trajectory of your career or business. Whether you're contemplating a major professional shift or simply want to fall in love with your work again, this episode delivers actionable strategies to make it happen.

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Speaker 1:

What's up, guys, and welcome back to another episode of Surviving the Side Hustle. On today's episode we've got Tammy. Tammy, how are you doing?

Speaker 2:

I am great, Rob. Happy New Year. How are you?

Speaker 1:

Oh, I'm doing excellent. This is a great week, kicking off the new year strong, and can't get better than having a great conversation with you.

Speaker 2:

I'm excited about this Great way to start the year. Everybody seems really refreshed and back in action, so this is a high energy week for sure.

Speaker 1:

Perfect, and this is a great way to kick it off. So, tammy, why don't we dive right in? Would you mind sharing a little bit about who you are, who you help, kind of situation and the problems that you're solving?

Speaker 2:

Sure, absolutely so. Again, I'm Tammy Alvarez. I'm the founder of the Career Winner Circle, where we empower business leaders to make a big impact and love every Monday again. And that is what we do for people who are in the corporate roles, people who are entrepreneurs, and business owners and leaders. If you find that you're stuck in that soul-crushing grind and that Sundays start to feel not great around three or four o'clock, then those are the people that we serve.

Speaker 1:

So, tammy, how did you get into this great world?

Speaker 2:

Yes, interesting, right. So I was a corporate knucklehead for decades and I was an executive on wall street and for the last 15 years of my career is leading big teams. So I had 2000 people in 36 countries. So I had that big girl job in Manhattan and I absolutely loved it until I did it. And I remember one day just sitting in this boardroom and having this massive knockdown drag out with all my peers on whose fault it was, that we were missing earnings. And I used to love these games.

Speaker 2:

And I jokingly say, especially in my book, that I got this disease that I didn't know was terminal for my corporate career and it was called I don't give a shit-itis. And so within about six months I had cashed out of Wall Street. I moved to a tropical island off the coast of Belize in Central America and started this coaching company and that was seven years ago and had no idea what I was doing, made all the mistakes you can possibly imagine. So you know, happy to talk to our listeners about all the things not to do, but that's really how I started is. I just couldn't find another way in corporate to feel engaged and motivated and excited about what I did anymore. So it was time to make a dramatic change.

Speaker 1:

Yeah, I mean dramatic and pretty stylish too. That sounds pretty awesome to dive down there and starting your own thing, and off the coast, yeah.

Speaker 2:

Well, yeah, and it was before you know. Anybody even knew what Zoom was. So I was like, how are you going to work? I'm like, oh, zoom, they're like what's that you know? But moving from a 14 hour workday, high stress, all that stuff, to going scuba diving a couple times a day before work was just a great shift that I needed to get out of the rat race and the corporate programming and also help other people do the same thing.

Speaker 1:

Well, I know myself and the audience definitely want to know how do you do that? How do you get in those scuba sessions early in the day? What is the secret?

Speaker 2:

Yeah, and I think the secret is not everyone can, you know, move to a tropical island, right? So let's be, you know, realistic here. It was a great time in terms of me for timing. You know, my daughter graduated college. She was off the payroll. The timing was just right for me. But I think we can find these moments of joy in what we do and we can create these scuba diving moments, whatever it is for you, when we're having a corporate job, to see if this is really going to work on a larger scale versus just a hobby, and when we hone in and focus on the things that energize us. And a lot of people focus on what they have the most experience in, or what's most marketable, what's most valuable, what they're expected to do. But when you can think about the things that you can do for 12 hours a day and end the day more energized than when you started, that's your sweet spot, and everyone can do that today and try and incorporate more of that into their day.

Speaker 1:

So how do you get them? So, say, someone's listening right now, they're like, oh, wow, this is definitely what I need to do. How do I dial in and you start working with them. How do you start right off the bat with like, hey, what makes you energized? Or how does what does that whole process kind of look like?

Speaker 2:

Yeah, so the process that we go through because we are absolute experts in career changers, right, and that was never the type of company I thought I was going to start, but it kind of found me. People were like what are you doing? How'd you do that? And I want to do that too. And so we're really a three-part process that we walk our clients through and there's been over 500 clients that have gone through this over the past seven years and the first part of this is really where we lean in to what energizes you. You know, we look into the past because we all have those moments where we have those like epic battle scene moments that we talk about over a beer, you know, in the pub it's like you're not going to believe what happened and this and all of those things, and so those moments can be lifestyles, because if it can happen once, it can happen again.

Speaker 2:

So we identify that and get rid of all of the expectations that people have and understand why you want to do what you do, because it's not about buying the Range Rover like your neighbor just got for Christmas and how do we really lean into that sense of self. And then from there we look and see where in the market is this in high demand and in short supply? And that's really where the key is, because it's one thing to know okay, I really am energized by this, but I don't get to do it. Enough. Fair enough, and you can add a little bit more into it. But when you can find a place where that's in high demand and in short supply, that's when you start to accelerate and that's when you start to see a significant impact that you're able to make on the organization and income that you're able to bring in for your family.

Speaker 1:

Well, so you said something kind of funny right there about comparing against what you have what the neighbors have. Do you see a lot of people either too afraid to kind of change or too slow or hesitant about change because they're stuck comparing themselves to either who they used to be Maybe I'm too old to change careers, or maybe I'm not old enough or do you see a lot of comparison with the individuals you're working with?

Speaker 2:

Oh, absolutely All the time. And it's not. You know, it's the comparison of I'm too much or I'm not enough, right? So there's always that, whether I'm working with a CEO, you know, of a major corporation, or whether I'm working with somebody who's got like 10 years in, we see that show up for everyone. So it seems to be a human, but we immediately go into this scarcity mindset, thinking that if we're going to have to make a change, we're going to have to start over again and give up all the things that we've worked so hard for.

Speaker 2:

And most of us can't sell everything and live in a yurt, right? So we need to keep that lifestyle up that we've built for ourselves in many cases. And so, getting rid of we call these the five lies, and there's a five lies that hold us back from making these career changes, and that's one of the biggest ones is I'm not enough or I have to take a step back, and everything that you've done in your career up to this point is valuable, and so when we can take that, figure out what lights you up and find a place in the market where that is absolutely needed, that's really the you know, the magic potion there.

Speaker 1:

So what are those full five lies? I'm sorry if you kind of brushed over those. Could you repeat those?

Speaker 2:

Yeah, no, so you know. So one of the first lies is you know, no one hires from outside the industry, right, so it's like I got to stay in my lane. But what happens? If you know the industry that you chose is now the Titanic, right, everything changes and so it's like if that was the case, then no one get into AI, no one get into these new industries, you know. So we want to think about, okay, the. You know, no one hires from within the industry. The other thing is I have to give something up right To to change careers. So that scarcity mindset.

Speaker 2:

We have another one that holds a lot of people back, thinking I need like my skills aren't transferable, because you can't really see how what you're doing today plays in different markets, you know. The fourth one is really talking about, and where people get stuck is in that imposter syndrome where you know, no one. You know how am I going to win against somebody who's been doing this for 10 years? No one, you know how am I going to win against somebody who's been doing this for 10 years? And what we do is we show people how being different isn't just like you don't have. That can be a competitive advantage and I'll never forget the day I learned this with my career has been if I learned it 10 years earlier, it would have made my life a lot less painful.

Speaker 2:

But I had this moment. I was working in compliance and I don't even know how I got in there, right Cause I was a front office girl on wall street and I was in someone's office a very senior executive and we were having literally just a battle, screaming at each other because I needed something done in the UK. He didn't want to do it. So we were screaming at each other that's how you communicate and he had this giant office right and the phone rings and I know he did this on purpose. So he picks up the phone, puts it on speaker and on the other end of the phone I knew the voice immediately and basically the conversation went hey, dude, how'd I do last night? And my jaw dropped because it was John McCain, the day after his first debate with Barack Obama, and I was like, and they sit there for 20 minutes bro-ing out on how the conversation, how the debate went, and I'm like, what am I doing here? So you know, I listened to the conversation. We get back to arguing. Of course I lose.

Speaker 2:

And I go back to my boss's office and I'm like, what are you doing? Like why am I here? I don't belong here, I'm not a lawyer, I'm not this, I'm not that, and I'm just raving like a lunatic and she just lets me rant. And then she starts laughing at me and she's like are you done? Yet I'm like, yeah, she's like, you're here because you weren't part of the problem. You're here because you think differently. You're here because you're not like everyone else.

Speaker 2:

And I had spent my entire career thinking that because I was different, I wasn't as good, I was less than when. The reality is the reason I because I was different. That's why I kept getting these opportunities. So for anyone who's thinking you know I'm not enough, I don't look like the others, you know I don't act or think like the others, you can absolutely turn that into your competitive advantage. And then the last lie is that some you know that corporate's going to take care of you, right, that the company will take care of you, and that's actually not true and not on purpose and not to be jerky, but that's not actually how it works. So until you become that CEO of your career and you start to treat your career like a business. That's when things start to change, and that's the big aha, for so many people is like oh, I actually have way more control over this than I ever thought I could.

Speaker 1:

Wow, yeah, those, those, those lies or myths there they sound pretty familiar. I hear a lot of people always talking about those are one way or another, something similar to those. But so, as an individual who's dealing with a lot of change all the time and you're seeing people moving careers and shifting stuff, where do you see everybody kind of moving and going to? Now Is a lot of people moving towards AI, or are you seeing people kind of getting into coaching or health or what is? Where's people? Where's everybody going?

Speaker 2:

Yeah, so we're in the beginning of 2025, right. So let's talk about how 2024 shaped up, and there was two big themes that showed up for our clients in terms of what to pivot to, and one of them was pivoting to entrepreneurship. And so, whether they started you know they all started their own. You know many of them started their own businesses. I deal with primarily very senior level people. I mean, we service everyone as a company, but my clients tend to be very senior and so they're moving in as fractional executives, you know, for startups and middle. You know small businesses that need that executive perspective but can't afford the full-time salary and they are living their best lives doing the work that they love and helping companies grow at the same time. So that's one big trend that I'm seeing is a lot of people moving into their own, doing their own thing.

Speaker 2:

The second trend that I see that's happening a lot is people from big corporate moving into the middle market.

Speaker 2:

Because you're able to make a bigger impact, have a bigger role right, do work with a lot of business owners and entrepreneurs that are getting their businesses off the ground or scaling is one of the biggest things that I saw last year, which will continue to see.

Speaker 2:

The trend for this year in terms of business operating models is moving their businesses, especially service-based businesses, to a subscription-based model. Businesses, um, to a subscription-based model. Because when you're in the service business, you're in this, you know you're hunting, then you eat what you kill and then you're like poor again, so you got to come back out with five more clients and you know you're in this delivery cycle that just gets really hard to get out of and so many entrepreneurs make the mistake of trading time for money. And so it's just so much fun looking at someone's business because I think most people will tell you, especially if you're in a service-based business, that you need a membership. I'm telling you that's a terrible idea and what you really need is to change the foundational core of your business to subscription. When I did that two and a half years ago, it was a game changer for my business.

Speaker 1:

Can you define the difference between membership and the subscription base?

Speaker 2:

You know. So membership, as the experts talk about it right, because it's out there everywhere is this low ticket item that you get a lot of people in, assuming you've got $7 million to advertise and get them in. You know that's content heavy and you know you, you've always got to update and refresh and all that kind of fun stuff. And I'm saying that that doesn't work, not for the average person who's either a solopreneur or a small team that doesn't have a bazillion dollars to advertise. The difference is from a subscription perspective. It's how you set up your core business. So, for example, when we coached, we would do, let's say, a five month contract and that five month contract would cost I don't know, somewhere between 10 and $20,000. And so when that contract was over, no matter how happy that client was, no matter how successful that client had been through coaching, getting them to write another $10,000 to $20,000 check was really hard. And when you take the exact same service, the exact same delivery model, but you turn it into a subscription instead, that's monthly now all of a sudden, you're not changing your operating model at all. All you're changing is how you bill and what happens is that client ends up staying significantly longer and you can close more clients, because now they're writing you you know they're they're swiping a card for $1,500 a month instead of at $10,000 a pop, and so that has been such a deal changer for me, because it's you know when, when contracts come in, you know, I think most of us, especially in service-based businesses, tend to have some type of cyclical nature to the business.

Speaker 2:

We do a lot of career stuff, we do a lot of leadership stuff, so that's usually the beginning of the year when they didn't get the promotion or bonus, and it's at the end of the year when they're sick of what they're doing. So we've got some peak seasons, but then everybody comes on and everybody goes off at the same time, and then, as a business owner, you're sitting here like, well, my bills haven't changed, and so how do we do this? And so by doing, by changing your core foundational model to subscription. What that does is, for us, that increased our LTV, our lifetime value, by 40%. Clients stay, not because they're not getting what they need, but because they're achieving more than they thought they could, and now they're in over their skis again and need more help. And so it is just absolutely a game changer for small business owners and entrepreneurs, and so it's been a lot of fun helping those businesses really lean into.

Speaker 2:

How do I do this? Because we think it's not going to work for my business Maybe I sell B2B. That's not true, it does work. Or it's too tech heavy, because it's not it's doing the same thing you're doing today. Or it's just too hard to implement and it's too much work to keep things up, and it's not that. So all the things that memberships are for low ticket items, subscriptions are not, and that's been a massive game changer for a lot of entrepreneurs last year.

Speaker 1:

Do people. So when you first bring up this idea, do they kind of hesitant about like increasing turnover of clients and maybe that initial not being able to get to work with them as much to the point where they fully are bought in? Do you hear people talking about that at all?

Speaker 2:

The things we work through most right Is how do you position this to your customers, right?

Speaker 2:

Um, in terms of how that works. And so when I did it, I did it, I flipped the switch, so I told you know, all my clients that were currently working with me, I'm like we're moving to a subscription based model. Here's how it works. 100% of them made the conversion, you know. And then, when you bring the new ones on, that's much easier to do, right and so, and then, because, when you think about that subscription-based model and that recurring revenue, when a client falls off, it's not a $10,000 loss, it's not a $20,000 loss and it's much easier to replace. And so most of it, from an entrepreneurial perspective, is the mindset in terms of how do I do this and deliver, which is, you know, very tactical, and we can, you know, work through the. You know how the sausage is made, basically, and then the other part of it is positioning from a market perspective. And how do I get my clients excited about this? And, trust me, whether it's a B2B or a B2C, everyone's excited with lower bills, right?

Speaker 1:

Oh yeah, of course, of course. So you keep talking about how it doesn't really matter whether it's B2B or B2C, how much uniqueness and variability is there with people and their different businesses and such. Because I feel like like everybody listens like, well, not me, mine's totally different.

Speaker 2:

like you don't know me, lady, like you haven't seen this and it doesn't work for me and my clients won't do it and all that stuff, right, totally, um, you know and that's very common to hear um, especially in service-based businesses Products we all know Chewy, we all know this Tech, we know that stuff because our credit card statements are littered with these small payments that hit our cards every month. But from a service-based business perspective, the key is this Most entrepreneurs come in to solve a problem. Actually, that's why every business exists is because you're solving a problem for someone in some way.

Speaker 1:

Well, you, should be right.

Speaker 2:

If not, you're not gonna be around for very long, right? So, um and so, when you think about that core problem, what you need to think about is where is your client before they come to you for the problem? And then, what are their needs after you've solved that problem? Because then you become a drug, not a painkiller, right? And so when you realize that oh, hang on a second the people that I serve, the companies that I serve, the individuals that I serve, here's their journey before they get here. And then, once they've achieved that, here's where they're going.

Speaker 2:

So, for example, in my business, we started with career coaching. Now, our people end up in a billion different ways, right? Some open their own businesses, you know, some go nonprofit, some go big corporate they're all over the place. And so over the years, we've developed the ability to coach on everything from I don't know how to interview to I need to choose a board of directors for my company and everything in between. And this wasn't done overnight. It was done basically as our customers had needs and we just built it on the fly, right? That's how we all do it, let's be honest, and so you know.

Speaker 2:

So, from that perspective, when you start to get these business owners to see that there's a longer ability to serve. You can make a higher impact in being able to stay with your customers longer. And exactly here's how you do that for your business and very specific to their service offerings and things like that. That's when the light bulb clicks in, right? So, whether you know it's a health and wellness coach, it's like, okay, well, what are they struggling with before that? Right? And like, where can you start to get in when they're realizing, oh, I'm about five pounds overweight instead of 50, right. And how do you start to serve them there? Versus, oh, I've achieved this now. Now, how do I change my diet? How do I change my lifestyle? How do I change my mindset? So, if you can start to build your toolkit to be there with your customers and be there for what they need as they're on their journey with you, it's magic.

Speaker 1:

Wow, yeah, it's really cool. That is pretty sweet. So what do you see? Do you see this subscription kind of going forward in 2025? Are you seeing any other things that people should be kind of like being aware of or starting to kind of make changes for themselves?

Speaker 2:

for 2025. One is not new news, right. It's the whole AI thing, right. And so many people are afraid, like I'm going to lose my job to AI. I'm like, no, you're not, you're going to lose your job to people who know AI. Those are the ones that, like human beings who know that, are going to take your job, and I think we need to be really aware that, based on the role we're in, based on the industries that we serve, like, pay attention to this and adopt this in as part of your business. So a great example I was just on a coaching call yesterday with one of my clients and she's a marketing executive, right In terms of advertising.

Speaker 2:

You know everything from social media advertising to TV commercials and everything, and she has all these different things and she's like, you know she was looking to pick up a few other other projects. And she's like I'm getting my clock cleaned by AI. I'm like, yes, you are, and that's never changing. So how about, instead of trying to compete against a computer, you build an advisory capability to show companies how to use this and how to use it responsibly? Because now you're not making the small dollars you'd be making doing the work. You're an advisor and you only have to be five minutes smarter than your clients because you've got the time to educate yourself and understand what's happening in the market. So pay attention to this. Like we're even incorporating AI into our coaching, right? We've got a meeting taker that identifies trends and stuff. My clients love this, you know. We've got other analysis tools that look at what have we talked about for the past six months and let's see if we've got some recurring trends that we really haven't picked up. And so, being able to use this to help your business move forward faster, especially as a business owner, get smart about it right and use that to your advantage.

Speaker 2:

If you are an employee for a company, make sure that this is in your bag of tricks. There are so many things that are out from Google and MIT and Meta on free AI courses. There's no reason not to get smart on this. So I think that's the big thing. That is a hangover from 2024 that will continue to be in our world. I don't think it's going anywhere.

Speaker 2:

You know the other thing I think there's so much economic uncertainty right now right, we're, you know, a few weeks away from another big change and we have all these things going on, and so the other thing I'm encouraging both, you know, business owners and employees is to diversify.

Speaker 2:

So you need to have multiple sources of income stream or, you know, from an employee perspective, really making sure that your brand is out there and known within the market, externally as well as internally within your company, because we don't really know I mean, the experts like to sit on Sambia Sea and pretend they know, but we actually don't and so, from that standpoint, the more you can diversify, the better you're going to be when things actually unfold.

Speaker 2:

So, like we service self-funded individuals, we service, you know, small business owners, which are like self-funded individuals because they're solopreneurs and things like that, through their business, everything to a large corporate, and so we can pull these levers as we need to when we see something you know slowing down, or we can put additional investment dollars into something that we start to see that's getting some traction. So just hedge a bit and see what are the things that you do every day for your customers that you can offer to a different demographic or in a different way, because you want to have that ability to be nimble, especially, I think, in 2025, when things are going to be a bit topsy-turvy.

Speaker 1:

Wow, some golden advice throughout this whole episode. Thank you so much for all this stuff. This has been incredible throughout this whole episode. Thank you so much for all this stuff. This has been incredible. But before we kind of wrap up and roll, where do people go to kind of stay in touch with you? Try to figure out how to work with you? Are you taking on new clients? Tell us the whole. How do people stay in touch?

Speaker 2:

Sure, absolutely. So. The one thing I love to ask all of our listeners to do is to reach out and connect on LinkedIn at Tammy Alvarez. Let me know you heard the episode and, more importantly, what you thought of it right, what you liked, what you did and all that kind of fun stuff. So I love to hear that. But you can always check us out at careerwinnercirclecom to get all that stuff.

Speaker 2:

And for your listeners, rob, what we're doing is we are offering, especially for the entrepreneurs. Let me be specific. So for your business owners, we are offering a free assessment to see if you can apply a subscription model to your business. So you answer some questions, we're going to get in and get ugly for about an hour and see what's under the covers and show you where those opportunities are, and all of that's for free. And then we also have a free career strategy assessment for people who are in corporate. So we start out with an assessment Are you ready for a career change? Which will kind of, you know, look under the hood a bit, and then again a complimentary session with me to really figure out, you know, is this the right time? If so, how does it work and what are some of the things that you can take away today, with or without an engagement, to really start to own your career in a more impactful way. So, whether you're in the corporate grind or whether you're a business owner, we've got something to serve everyone.

Speaker 1:

Wow, that's awesome, and they can take those assessments at careerwinnercirclecom.

Speaker 2:

That's right, and we'll put the links in the show notes too, so that way they have it Awesome, awesome, and over on LinkedIn too.

Speaker 1:

Don't forget Tammy Alvarez. Check her out and let her know about the episode. Yes, so, really seriously, thank you so much. There's so much like golden nuggets in this. This is incredible. I really appreciate you taking the time Kicking off the new year strong. This is a perfect way to do it. Listen with this episode. So, tammy, thank you. Thank you so much for chiming in today.

Speaker 2:

Yeah, cheers to an epic 2025. It's going to be an exciting one, that's for sure.

Speaker 1:

There we go. That's all we've got today, guys. Peace, peace, peace.