Breaking All The Rules In Coaching, With Tammy Alvarez

Unleash your potential and defy conventional boundaries – discover the transformative power of breaking all the rules in coaching. In this episode, we have a remarkable guest, Tammy Alvarez, the visionary CEO and founder of Career Winners Circle. Tammy’s Career Winners Circle is a haven for professionals seeking to supercharge their growth and transform their careers rapidly and sustainably. Tammy’s coaching style combines her extensive experience in the C-Suite on Wall Street with a results-driven approach that challenges the norm and inspires her clients to make a profound impact. As a result, her clients wake up energized and motivated every Monday morning. Today, Tammy discusses her rule-breaking philosophy, unveiling the secrets behind her coaching success. Discover how Tammy’s unconventional strategies can help you break free from the shackles of traditional thinking and unlock your full potential. With her spirited approach and practical insights, Tammy challenges conventional wisdom, guiding listeners toward career breakthroughs they never thought possible.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/tammy-alvarez

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Breaking All The Rules In Coaching, With Tammy Alvarez

Founder Of Career Winners Circle

In this episode, my guest is Tammy Alvarez. She is the CEO and Founder of Career Winners Circle, which offers a comprehensive collection of coaching and training programs designed to strengthen leaders to grow their careers quickly and sustainably. Her spirited break-all-the-rules approach blends decades of C-Suite experience on Wall Street with a pragmatic results-based coaching style. She helps business professionals create an impact so they can love every Monday morning. Prior to starting Career Winners Circle, Tammy held a variety of leadership roles at AIG, Bank Leumi, Genesis10, Bank of America, and Compuware. She earned her Bachelor’s Degree in Business Administration from American Intercontinental University.

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Tammy, welcome. Thanks for doing the show with me.

Thanks. I appreciate the invitation. I’ve been looking forward to this.

Tell us about Career Winners Circle.

It is a coaching and advising company that helps people get the most out of their careers. The areas that we focus on most are helping people drive career strategy and figuring out where they need to take their career and where they want to. We have a lot of work that we do also in leadership development. If you’re on the right path and you love what you’re doing, how do you thrive in that environment? We also help new entrepreneurs and small businesses. If your career path takes you that way and you’re looking for advisory work on how to do that, in a profitable and fast way, then that’s another area that we help people in.

Do you tend to do more work with people individually or more work through companies that hire you to work with their teams?

Most of our work is done individually. When I started the business, I left a thriving career in Corporate America. I was still addicted to the work. I knew that if I started selling business to business, I’d get sucked right back into what I was trying to get out of. The organization was founded on a business-to-consumer model focused on those people who are mid to senior level who aren’t getting the coaching, guidance and things that they need from their companies and that are willing to self-fund because they know that with a little guidance, they’re able to level up much more quickly.

Most people tend to focus a lot on working with companies because that’s usually where the money is. I also thought about what I was trying to do with PathWise as being oriented toward a more business-to-consumer model. I think particularly because this generation that’s starting their careers is going to change jobs. They may change careers multiple times during the course of their career. They can’t depend on the company that they’re working for necessarily to be giving them the long-term advice that they need. It’s a little bit like the old world of defined benefit pension plans shifting into defined contribution 401(k) plans. This is born from the same thesis or general trend.

What ended up happening is I was only selling to self-funding individuals, but as I started working with my clients over time, they start bringing us into their organizations. From an organic perspective, we do support companies in terms of their leadership development and things like that, but that comes from clients who have funded themselves and then say, “My team needs you or one of your coaches.” That’s another way that we have started to begin to work over the past years with businesses as well.

You had a successful career in financial services and IT consulting. Was there a moment for you that led to the decision to go in a different direction and get into coaching?

There’s one of those defining moments. I spent my entire career in and around Wall Street. I became known as a transformation expert because I love change, drama and all things. Typically when the building was burning, and everyone was running out, I was bringing my team, and we were going in. Fortunately, in financial services, there was never a gap. There was always some kind of crisis that was going on. Through that, I earned a reputation, my brand and loved what I was doing.

I remember we were sitting on an earnings call. We were with the analysts. We were getting our clocks cleaned because we had missed earnings. I had that spidey sense for the past couple of years that this was no longer serving me the way it had in the past. After that, I was like, “This sucks. I’m sick of this. I am making bad decisions quarter after quarter to serve the analyst, the industry and the stock price,” but in the job, what’s important is your shareholders. It no longer served me.

The timing was right. My daughter was graduating college. She was off the payroll. With my big fancy apartment in New York, because I was a managing director and we had all the fancy things, the lease was coming up on that. I decided, “This is not going to work for me anymore.” Pivoting into another executive role for me was the pinnacle of failure. It was another acronym and the same crap. I couldn’t do it for another minute. It’s been many years. I cashed out, moved to a tropical island in Central America off the coast of Belize and started this coaching company.

You’re then in Mexico City. You talk about breaking all the rules. What are the core beliefs that underpin your approach to coaching?

You touched on one of them. I reinvented my career many times, mostly because I got bored and wanted something different, but I didn’t know what I was doing. I used to do what comes naturally. As I was doing that and with the benefit of hindsight, I realized that many people say stuck in these soul-crushing jobs that they hate because they feel that there’s no other option. There are several flat-out lies that we are either taught or we believe that hold us back. You touched on one when we started, and that’s the company’s going to take care of us. If we do good work, we get noticed and recognized. The right thing will happen, but that never happens.

If you don’t advocate for yourself and you don’t drive the change that you want, you will never get where you want to be. Another core belief that people hold people back is they believe that if they want to make a substantial change, they’re going to have to take a step back. As it turns out, if you do it wrong, that happens. When you do it right, then you have got these amazing opportunities where you’re paid more.

We spend a lot of time helping mid to senior-level leaders pivot into something they’ve never done before. They’re worried because they’ve got ex-spouses to pay for, houses, kids in college and all kinds of toys. They can’t sell everything and live for a year. When you do it right, on average, our clients are making 20% more. One of the other core beliefs that people, for some reason, have given up on is not just the pipe dream but the demand that you should love every Monday. Everything that you do should light you up. If it doesn’t, you have the power to change it.

You have the power to use that to pivot into a career that you’re thriving in and where you feel like you’re making an impact. You’re working with people who get you. I don’t know how many times you look around, and you’re like, “I’m surrounded by the idiots here. I can’t take this anymore.” To give up on all of those things and thinking that it’s for other people doesn’t work that way, but the reality is it does. You can structure that type of reality for yourself if you want to.

Your marketing materials brought to mind Moonstruck, that scene where Cher slaps Nicolas Cage and tells them to snap out of it. It’s a little like what you’re saying to your clients, figuratively, in terms of getting themselves out of the inertia, the doldrums that they’re in. What do you do specifically to get them to snap out of it?

Put themselves first. When you are in a job that doesn’t serve you or in an organization where there’s not a good culture fit, you tend to feel like you don’t fit in. You spend a lot of time trying to make yourself fit in. It’s a waste of time because it won’t work. What we teach our clients to do is to come back to the center. I’m not like an area fairy coach. I’ll give you a kick in the butt as much as I’ll give you a hug.

What we want to do is understand what are the things in terms of the tasks, the leadership environment and the culture that lights you up. Not the things that you think are most marketable or valuable but what are the things in the environments that you can lean into for twelve hours a day and never get tired, then go find that. When you do that, then you are in a position where you’re naturally going to be energized. That’s step one.

Step two is what we spend a lot of time doing, which is helping clients find what I call their IT factor. That’s a unique set of circumstances, perspectives and experiences that make you better, not just different than everyone else. Everyone has that. When that IT factor is in high demand and short supply, then that’s magic. All of a sudden, you’re showing up big in places that desperately need what you have and value what you can deliver and you’re able to make a much bigger impact.

You’ve chosen the IT factor over the superpower.

Superpower has a bit overused. IT factors are used a lot too. There are only many different ways you can cut this. What it boils down to is what are the things that light you up? How do you use that and your experience to find places in the market where you are in high demand and short supply? That’s what people forget about. There are so many situations. Let’s face it. The economy has been volatile for decades. It will not change. That creates an opportunity because volatility does create opportunity from a career perspective. When you find places or industries where the skills that you have aren’t organically available, that’s where you go.

You start shifting from getting paid for what you do to getting paid for what you know, and then that’s how you lean in. You’re high-demand, your compensation goes through the roof and the amount of impact that you’re able to make is much more significant because you’ve got the playbook for what they need. I’ve got a good example. One of my corporate clients are hypergrowth for over a decade, and they’re hitting some headwinds. They need to continue to grow, but with more financial, let’s say mindfulness because you throw money at a problem. For those that have grown up in that company, they don’t know how to do that because anytime they’ve had a problem, they hire more people and throw more money.

That sounds like most of the tech industry.

This is why we’re seeing the compression that we’re seeing. From that perspective, when you come in and you know how to do this well, inspire people and be able to lead, then all of a sudden, you are the holy crap. Every person that is ambitious and cares about their career has that. What we do is help them find it and then figure out where are going to be most valued in terms of what’s going on in the market.

For clients who’ve come to you with that need to break the rules and snap out of it, what percent of them end up staying with the company they’re with? What percent goes to another company in the same industry? What percent goes in a different direction?

I do have that data. You can take the girl out of Wall Street but you can’t take the Wall Street out of the girl. I hang onto all the stuff, keep track of my clients and see where they’re going. About 10% to 15% end up staying within the organization that they’re in, but they usually end up getting promoted because what happens is, if they’re in big enough companies, there are other parts of the area or the organization that has the culture, vibe and demand that they need and they start showing up differently because of they’re getting coached. All of a sudden, this dead end seems like it’s an option.

Out of that 10%, let’s take the other 90, about 60% to 70% of those people make a pivot to doing something that they’ve never done before. The smartest or the easiest way to do that is to either stay in the same role, new industry or stay in the same industry with a brand new role. That’s typically where you’re going to be able to see that type of pivot, whether you and I encourage people to think about things in terms of an ecosystem.

Think about all the different companies and businesses that are involved in your business, whether it’s a vendor, supplier, upstream or those types of things. They’re very different. It’s a greenfield opportunity to do something new, exciting and still be relevant. Another 10% head into different fields and new roles. I’ve had a finance exec end up working as a government liaison for a renewable energy startup. You can’t get two more diametrically opposed things, but there was enough commonality between their capabilities and interests that it worked out. There are a couple of other examples like that.

You also work with people who are trying to get a promotion. It’s a little bit different situation. You talked a bit before about people who don’t feel like they’re fitting in where they are. What are some of the other reasons for people who are more interested in staying where they are but want that promotion or feel that sense of being stuck? What are some of the other things that tend to be the cause of their feeling stuck?

The biggest root cause, and I suffered from this too early in my career until I realized that this was not getting me where I wanted to go, so I had to change my tack, people are not spending enough time building what I call their power base. We worry about networks, all that kind of stuff, how many connections we have on LinkedIn and all these quick vanity metrics. At the end of the day, what you need to get promoted are three things.

Tammy Alvarez: People are not spending enough time building their power base.

The most important thing is that you need to have sponsors within the organization beyond your boss. This sponsor is somebody who is going to advocate for you when you’re not in the room because here’s the reality. There are only many promotions to go around. If somebody’s going to nominate you, that’s at the expense of their team members and managers.

You need to be able to have those stakeholders that are around the table that are all saying, “Out of all of our leaders, this is the one we need to bet on.” How do you do that? How do you become that person that everyone advocates for at the expense of their people? Bonuses work the same way. What you need to do is identify and lead on a problem that everyone is afraid to take responsibility for. In my mind, there are lights on, BAU, do your job, and there are two other extra credit project type things that one gets you noticed and one will not.

One is what I call The Doormat Project, which is crap no one else wants to do. Don’t take those because no one wants them but the other ones, I’m a New Yorker. I call them My Third Rail Projects. The third rail in the subway system, if you touch it, will kill you. We all see them 1 mile away. These are massive problems the organization has. You can drive a truck through it. It’s big.

No one wants to touch it because it’s like a dead man walking. The opportunity for failure is significant. Even on a small level, if you start to handle the things that people are too afraid to touch when everyone else is hiding under their desk and you’re like, “I will lead this, but I’m going to do it inclusively. Get the right people involved. Make sure that it’s transparent,” you don’t have to get it over the finish line. You only have to get it a little bit over the finish line, and then you’re seen as the leader that people choose to follow.

When you can do that, then you start to get that sponsorship that you know you need. The third piece is you need to believe it yourself. Too many people are the last ones to agree that they need it. Even if they want it, you don’t step into that role. If you’re not stepping into that role and you don’t believe you can do it, then you won’t. That trifecta is the things that you need to be able to move your career forward and get promoted.

How do the people who jump into the fray, the 2nd of your 3 things, avoid becoming the perma fixer? Where do they get thrown on one high-visibility project after another, but they’re always flying a level below where they want to be?

The biggest rule is don’t overcommit to your ability without compensation. Companies will only pay you what they have to. If you don’t demand compensation for yourself, your title and the span control that you deserve, you’re not going to get it. Why would they? It’s not personal. It’s business. When you start to treat your career like a CEO, or you look at your career like a CEO and a business, you make different decisions. You want to get in there and fix something, but what I’ve always seen and what I help my clients do is as you are doing that big thing that people are afraid of and bringing that to a solution of some sort, then you usually end up taking it over or end up in a position where you can call where you want to go next.

From that perspective, the way you don’t stay the perma fixer and you’re able to continue to move up is you’re building a new thing that people need, you can oversee it and continue to grow because the higher up you go, then the bigger problems you can fix. You can start this in a very micro situation in your department or the group that you work with and then continue to use the same techniques but use that to continue to level up every time you do it.

You focus on executive presence as well. Executive presence is one of these terms that probably means somewhat different things to different people. How do you define it?

I define executive presence as being the leader that people choose to follow. It doesn’t matter what the org chart or the hierarchy says, but people will go to battle for you no matter what. When you have that, then you’ve got executive presence.

How do you help your clients build that?

We look at six different specific leadership attributes that you need to be able to get there in whatever way there is. It’s building that vision, being able to drive the strategy to be able to execute that vision, moving forward, being able to get that done, handling the roadblocks and inspiring people along the way. We look at all of these things. We start to break down where are their natural strengths. We’re going to go back to the overused “superpower” word. Many leaders are focused on the things they’re not good at, where it’s like, “I got to fix this. I’m terrible at that.” They’re obsessed over that.

You’re never going to be, so don’t try. When you identify those core things that come naturally to you that are strengths and you perfect, hone, build and get better at those, you will grow your career significantly faster. You will develop that executive presence significantly faster if you sit there trying to fix all the things that you don’t. A core part of our coaching methodology is we play to your strengths. You learn how to use those and leverage those as an asset and, at the same time, build mitigation strategies on how you close the gaps for the things that you’re not good at. I’ve led ultimately at the end of my career. The biggest teams I ever led were about 2,000 people across 36 different countries.

I had a lot going on. There were a lot of things I suck at, but I made sure that I surrounded myself with people who had the skills that I didn’t and that I felt were smarter than me, and so I listened to their advice and also the people who were brave enough to tell me that my baby was ugly. The further up you go, the less honest people can be. What you’ll hear at the ground level is very different than what you’ll hear 3 or 4 levels up. You start to buy your own BS after a while because everyone is feeding it to you. You want to surround yourself with people who will challenge, be honest and say, “What you think is happening is not.” That’s how you build that executive presence having those people that will challenge you as well.

One last coaching-related question is boundary setting. This is another area that you’ve worked with clients on. The whole idea of work-life balance and boundary setting is taking on a much different meaning in our post-COVID work world. I’m curious to hear how your clients are struggling with setting boundaries and the guidance you give them on how to better do so.

There’s still so much going on in terms of the call back to work versus working remotely and all that mess. The way I look at boundaries is the way I look at your career trajectory. There’s seasonality to our careers. There are times when you can take more risks and you can’t, depending on what’s going on, kids in college or those types of things. Instead of looking at boundaries in terms of equality every week, and there’s a lot going on, what we need to do is constantly check in on where our priorities are. What’s going on? There are times when you’ve got to lean into work.

It’s like, “There are no boundaries. I got to get this done.” It’s a short sprint. It’s not years, but you’re able to do that. There are times when you need to take care of personal things like aging parents and children. That’s where you’ll be like, “Good enough is going to have to be good enough.” Where the whole boundary setting comes in is being aware of not only what your priorities are but what your priorities are in the moment because they’re going to shift, change, flex and find the opportunity and the discipline to be able to do that.

I find that with almost all my clients as we go through this. A lot of us have this hero complex. We think if we don’t get involved, don’t respond to that email at 10:00 at night and don’t log on on Sunday afternoon to get a head start on the week, bad things will happen. I guarantee you, it won’t. For the most part, we’re not saving lives. If you’re saving lives, that’s a different story. For most of us, in a regular corporate role, we overinflate the need for our involvement. When you start to realize that maybe that’s a little more self-imposed than not and change those behaviors, good things start to happen.

Tammy Alvarez: For most of us, in a regular corporate role, we overinflate the need for our involvement. When you start to realize that maybe that’s a little more self-imposed than not and change those behaviors, good things start to happen.

One of the other people I interviewed had an interesting take on it. His view is, “I want to do only the work that I am uniquely good at.” It was a diametrically opposed view of the people who are like, “I have to be involved.” His view was, “My job is to find people who make it possible for me to do almost as little as I can.” This is a person who’s leading a very big organization and is very engaged. It’s not like he’s slacking off by any stretch, but it turns the whole thing on its head. It’s empowering and delegating to people in your organization to tap into their full set of strains so that you can focus on your superpower.

My team does the same thing. There are things that I suck at, and I know that. Those were the first things where I’m like, “Let’s get some help and support.” The best thing I can do for my company and my team is to stay out of the way, feeding into the same concept for sure.

It’s a good segue into talking about your role as a business owner. How did you find that transition out of the corporate world and into being an entrepreneur?

It was a disaster. I was such a hot mess. I had no idea what I was doing. I made every mistake you could imagine. I knew it would be different, but it’s like having kids. You’re never ready, no matter how much people tell you. I screwed everything up. You name it, I made the mistake. The good news is, though, because of my corporate training, I’m used to making mistakes, failing fast and pivoting. One thing that saved my bacon was my ability to say, “Hang on a second. Slow. This doesn’t work. Let’s try something different.” I found the transition incredibly difficult.

The solopreneur route was very lonely for me. I’m an adrenaline junkie. I’m used to 10 hours of meetings, 4 hours of work, lines out my door and those types of things. All of a sudden, no one needed me. It was a very weird transition. Learning how to be a smart entrepreneur and spending my money instead of other people was a bit of an adjustment as well. Ultimately, while I have a sales background, and that’s how I grew up in terms of the early parts of my career because I decided to go business as a consumer, I didn’t know any of it. I didn’t know sales funnel or email marketing. I knew nothing.

I’m adjusting to all this. One of the biggest mistakes I made is I built this great offer that I know was desperately needed. It was how to be a good transformational leader. That was my background. I know people suck at this. What could possibly go wrong? The big mistake I made is I didn’t ask people who would maybe buy it for me if they would pay for it. As it turns out, I built this great offer for something no one would buy because I wasn’t selling to businesses. For people who were self-funding, that wasn’t a pain point they were willing to pay to fix.

I’m wasted in the first 6 to 7 months of blowing money and having no idea what I was doing. I quickly hired a coach, and I’ve had a coach ever since. They’ve changed as my company has grown, but I realized that I need a wingman to help me with what I’m doing. In 2023, we’ve got five coaches. We’re thriving and growing like crazy. Fortunately, the mistakes weren’t fatal, but they were good learning experiences.

Sometimes they’re moderately expensive. What’s the state of the business? How much of it is about one-on-one coaching, leading courses, and all of that?

All of our stuff has a live coaching element to it. It doesn’t matter. The idea of these courses is to set it and forget it. People don’t do it. They don’t get the value from it, let’s face it. What we like to do is provide a variety of different ways for people to lean in. Most of our stuff is private. It ebbs and flows. During COVID, our staff went to a group because two things happened. Demand went through the roof, but people’s willingness to pay private coaching rates did not because they were hedging financially for good reason. You then go to a one-to-many model so that way people can get the same level of transformation for themselves but at a lower price point.

Between quick challenges where it’s hitting the reset button, group coaching where there’s a live session every week or private coaching, all of those things are a nice blend so we can meet our customers where they want to be, both financially as well as some people like a community. They build this little cohort, and they got ride-or-die partners that they’re not working with that they can lead on. I keep in touch with many of our former clients. There’s like an alumni group. They stay in touch, which is great. It is seasonal in terms of what’s going on in the market.

Most people are looking for private work, but they’re not what we’re finding also because what we’ve done is moved to more of a subscription-based model where there’s not a coaching engagement per se. We have a coaching plan. We know what you want to accomplish, but what happens is when you achieve something, you’ve got new obstacles and new opportunities. You’re in environments that you haven’t been in before. They’re finding that as we continue to coach with them, as they grow and evolve, they’re growing significantly faster.

It’s interesting because I’m in the process of a survey that I send out once a year to our growing client base. So in early days, I’d like to understand the long-term benefits of coaching or not, but so far, 75% of our clients are making more than 30% when they started working with us. This is after they’ve stopped working with us. Those types of things are interesting to see the way people are using coaching in replacement of the company’s support that they’re not getting to start to advocate for themselves and get where they want to go a lot faster.

It’s a little bit like physical exercise. If you invest in it, you will get better. You will see noticeable improvements, but you’ve got to commit to doing it.

There’s no pixie dust. I didn’t have that in the budget. You have to do the work yourself, but you’ve got these great guides with all of our coaches that help get you there. The fundamental difference in how we coach is that we advise. ICF probably hates us. I don’t know. Instead of asking the 700 questions, it’s always our client’s journey, but sometimes you need to be told what to do.

At least once a week, out of my mouth will come, “Don’t do that. That’s the dumbest idea ever. That’s career suicide.” That blend of advice and helping them get there the way they want to is big, and it does have significance. I love it because they’ll come back the next two weeks like, “I did that and it worked.” I’m like, “I know.” That’s always fun when you’re able to help them do that.

Different space, but have you seen this show on Apple TV Shrinking?

I have not.

Jason Segel is the star. It’s got Harrison Ford and others in it as well. He’s a psychiatrist. He gets tired of asking questions and not saying what’s on his mind. He decides to start telling people what to do, and it goes from there. I won’t spoil it for you in case you want to watch it.

That’s what my advisor does for me. I’m like, “If some coaching headspace limiting beliefs, all those kind of fun things, which is desperately needed, at every point in time in our careers, but it’s also the, ‘What do I do here? What do I think about this? What decisions do I have to make? What kind of critical thinking do I need to consider to make a good outcome for everyone?’”

Sometimes you need a nudge or a push. What are your aspirations for the business over the next few years?

We are in hyper-growth mode. Aspirations are to continue to grow. We’ve got five coaches that we’ve added to the platform so far. We’ll have a total of ten by the end of 2023. We’re going to continue to grow and serve our clients. Each of our coaches comes from a different perspective. They’ve got different professional backgrounds. It’s fun to be able to leverage for our clients the multi-dimensionality of our coaching staff. For example, I’ve got a private client who has a lot of board work. She’s presenting to boards and stuff like that.

She’s in a very male-dominated industry, and there are a lot of bullies on the board. This confident, assertive, self-assured woman struggles with holding her space at the ward level. I’ve got one of our coaches who got a military background, and it’s great practice. He can go bully her around, and she can practice the things that she works in a safe environment.

I’ve got another one who’s looked at. She’s done a TED talk and got amazing background, but she’s a communications expert in terms of presentations. For our clients that get tongue-tied or feel like, “I’ve got a big presentation,” being able to bring a situational expert in to help our clients with a specific need as we continue to broaden out the breadth of our coaching staff becomes more valuable for our clients.

Do you find that a lot of your clients take advantage of multiple coaches like they work with different people in your group on different things, or do they tend to zero-in and pretty much and work with one person?

Primarily, it’s one person because you’ve got that relationship. I’m a negotiation expert. When it comes to comp negotiation, being able to hold your own and do those types of things, that’s my jam. I’m happy to come in, help supply and support that. You’ve got your primary coach because that’s the one who knows you best. That’s the one you’ve got the best compatibility with, and then we bring in experts to help our clients through very specific situations when they need it.

Go back to the beginning of your career when you were in school. I’m sure you didn’t imagine that you would be living in Mexico City and running a coaching business. What did you see yourself doing professionally when you were a college student?

I didn’t get my college degree until I was 40. It’s a very interesting or different trajectory in terms of being a managing director on Wall Street as a young female with no college degree. I never spent a day in college. Long story short, what ended up happening was that as a teenager, my parents split up. We didn’t have any money. Quite frankly, I pretty much sucked in high school. I was not motivated to continue on my dime, so I started working. I figured, “Let me work for a couple of years, figure out what I want to do, then I’ll go back to college,” but then I kept getting promoted. From that perspective, I got married and had my daughter.

All of a sudden, I’m sitting here at 40 years old, managing giant teams, having a thriving career and never spent a day in college. I finally went back to get my degree when I was getting vetted to sit on a board of directors for a tech startup. It was perfect. My connections were great. We’re going to be able to help grow. I got DQ’d because I didn’t have a degree, and it looked bad on the bottom. I’m like, “Are you kidding me?” In spite, I went and got my degree.

I’ve always played because I’ve been the underdog, poor girl who grew up in a country town in New Jersey, didn’t have a lot of money and never traveled. My background was very different from those that I ended up working with. My risk tolerance, I’ve always played like I’ve had nothing to lose because I didn’t have anything to lose. That with a lot of moxie and the benefit of having some tremendous mentors in my career who have been single-handedly responsible for putting me in situations that they knew I could handle that I didn’t think I could. Very early in my career, I didn’t know I wasn’t supposed to be able to do these things.

What’s interesting is we’ve pretty much banned educational requirements on job descriptions other than maybe when there’s a professional certification involved. The idea is to broaden the candidate pool. It certainly feels like five years into adulthood. Does it matter anymore? Historically, the work world has clung to fifteen years of experience with a Master’s degree. It’s interesting how all that’s changing.

You have a personal perspective on this. I wonder what it’s going to do to the value that people place on college. Some of this is COVID, but The percentage of people who are going off to a four-year school has gone from 70% to 60%. I wonder whether there’s a big change in the tide coming around the value that people put on getting a college degree versus going right into the work world and making it for themselves.

Speaking in the US at least, the entire education system could use a little disrupting, if you ask me, whether it’s a post-grad. I even saw my daughter. She’s been out of college for a bit, but even the best and brightest kids in her school were going to community college for undergrad for the first two years. Why are they going to be spending $80,000 a year on 101 and 201 classes on Gen Ed? That doesn’t make any sense at all. We have to rethink how we structure education and the pricing of education.

Tammy Alvarez: The entire education system could use a little disruption.

We are putting these children in poverty before they even have a chance to get out and make any money. It’s a hot mess. Until the value is there. In my time, that was the thing I was most insecure about. HR and my bosses knew I didn’t have a degree, but it was not something I touted that I was proud of like I do now. That was a closely guarded secret because it was a thing I was most insecure about, but things are different now. The generation that’s coming up has a different perspective. It’s not a work-first mentality, and I like it. The balance that they seem to bring before they even get started is something I’m helping my 30-year career clients start to migrate and unwind.

It is noticeable that they put work in a different place in their lives than our generation was taught that you have to do. It will be interesting to see as life continues for them, whether they put themselves onto more of a harder driving track or whether they don’t and stay comfortable with the fact that maybe they’re not going to have as many of the trappings of life as the people who do.

Is that a bad thing? One of my biggest a-ha moments was when I moved to Belize. We’re on this little tropical island off the coast of Belize. It was a diving community because we left scuba dive. I remember for the first two years, I have never made less money. We’re going back to when I started practically. I never made less money and lived richly in my life. Amazon doesn’t deliver to Belize. No one asks you what you do for a living because no one cares. You’re either a good person or a jerk, and that’s it. To be able to go from Manhattan Wall Street money, power, things, and status overnight go to basics.

I joke around and I’m like, “I went from Soho to Boho,” to a place where people wear flip-flops as formal wear. No one cares about how much money you have or power. Everyone’s on the playing field and no one cares. That to me was the biggest reset in my adult life I’ve ever had. Having the benefit of hindsight, did I really need those fourteen pair of Louis Vuitton designer shoes and all the fancy handbags? Probably not. Don’t get stuck to begin with, and then you’re not going to miss it, but there’s such a rich life that can be lived outside of commercialism, at least in American culture, that a lot of people get sucked into.

When you look back on your corporate career now that you’re a career coach, how would you rate your career ownership and your moves from the beginning of your career into your decision to jump into what you’re doing?

In terms of owning my career, it’s A-plus. I’m an impatient person. I don’t suffer fools. I have this horrible ability to be incredibly direct without a filter. I was always messy. Remember, I have a high-risk tolerance because I felt like I had nothing to lose, but also if I didn’t like something, I changed it. I didn’t stay. I’m like, “If this is a hot mess and I can’t fix it within where I am, then it’s time to leave.” I’ve been fired twice as well. I’ve certainly outstayed my welcome in a few places both times when I’ve inherited a boss, in a role, doing a great job, the boss leave, a new one comes in, and that didn’t work out.

In terms of taking ownership of my career, I always felt like I needed to do that because my mother was put in such a compromising position. She got pregnant with me in high school, and dad left. We were homeless for a bit. It was a hot mess. I saw how hard she struggled. I saw all the pain she went through, and that was my driving force to say, “I’ll never be like that.” I overcompensated significantly in terms of never being like that. Not having the apple pie upbringing that a lot of people have the luxury of and saying, “This is it. It’s got to be me,” that’s where all that came from.

I was always in control and if I didn’t, I left and did something different. I changed eleven different major companies along the way and lots of different roles. I would always get promoted a year and a half because I was being ambitious. If my role wouldn’t keep up with me, then I’d find something else that would. I’ve also had the benefit of those mentors that help be my sponsor and help advocate for me within the organization beyond my immediate boss, which is great.

What’s a day in life look like for you?

I work about 30 hours a week, give or take. Weekends are off. Mornings are mine. Two days a week that I’m coaching and then three days a week where I’m working on the business, other coaches and our operational teams to make sure that we’re there for our client and our coaches, growing the business, doing stuff like this and being able to help get the word out there because there are so many people that don’t know how easy it is once you get help to finally turn that corner and get to a place where your life is in track with where you want it to be. You don’t have to accept the status quo and second best. When you know how to do it right, and you have a fun partner to do it with, then all of a sudden, everything changes for them. The more people that know about that, then the better it is for everyone.

You talked about growing the business. What are the things that you do for yourself? What are the things that third parties help you with?

In terms of growing the business myself, I spend a lot of time with our client base, both active current and previous, their referrals are the lifeblood of our business in terms of any business. A lot of our business comes through those referral partners. The other thing I do to grow our business is work with channel, referral and affiliate partners. These are other coaching firms or business consulting firms that serve the same market differently. They’ll refer clients to us regularly as well. In terms of our coaches, they all have the networks that they’re working with. They’re out there working with their communities and networks to grow their business as well.

We also do advertising. We do some advertising in terms of YouTube and Google. We’ve got a good PR firm. We’ve been published in Business Insider and MarketWatch. Wall Street vet on how to pivot during a crisis. Those articles got published, which was good. We’re continuing to work with that and become a little bit more mainstream in terms of how people can find us. That’s the biggest issue.

People don’t know we’re here. If they can’t find you, then you can’t serve them. I learned early that for a lot of the funnel experts, that stuff doesn’t work, at least for me or any of my other corporate clients or my small business clients. We get back to some more traditional, blocking, tackling and handling people one at a time, like human beings, which is refreshing for many people.

You talked about scuba diving. What else do you do to recharge your battery and keep yourself energized?

My partner and I love to travel extensively. It’s a purpose-built company that, as long as I have my laptop, we’re in business, but hiking is a huge thing for us. It’s in terms of a lot of hiking, cycling, scuba diving lots of stuff like that. As long as it’s water or mountains, I’m super happy. We’ve got a volcano that has decided to be a little bit active. In some of the bigger and higher elevations, hiking is off-limits. Hopefully, that’ll calm down at some point. We can get some proper steep hiking in.

I would like to come down to Mexico and do some of the mountain hikes there that are supposed to be beautiful other than what I was there once for work.

The vibe is amazing. I’m also a big wine drinker. I love wine and all the things about it. I’m starting to learn about mezcal, and that’s also a lot of fun. It’s social. We’re always with other people doing some fun things, which is always good.

Last question. What do you wish you had known when you were back at the beginning of your career that you know now?

For every position I was in, I had already earned the right to be there. There are so many times that I felt like I was in over my skis that I didn’t belong. I thought like, “Somebody’s going to find out.” You want to talk about the poster child for Imposter syndrome before it was a thing. That slowed me down, even as fast as I was able to accelerate my career. I was having that consistent and persistent feeling that I didn’t belong and didn’t deserve to be there.

Tammy Alvarez: For every position I was in, I had already earned the right to be there.

I was at Bank of America. We had bought Merrill Lynch. There was a financial crisis. All hell was broken and loose. I was in charge of working with regulators around the world, trying to calm everybody down, keep the bank open and do all this regulatory stuff. I had no idea what I was doing. I wasn’t an attorney. I wasn’t a compliance person. I was a front office and middle office girl. I had no idea how I ended up there.

I was in a very senior executive’s office. The only way you could communicate was to scream at each other. We were in a cage match, screaming at each other because I needed some things done in the UK. He didn’t want to do it. I’m like, “It’s my job to keep your guys out of jail.” We were in this giant argument, and then his admin puts through a call. It’s John on the phone. The executive work is a total jerk egomaniac type of thing. He puts it on speaker. He’s like, “What’s going on?”

On the phone, the other guy goes, “How did I do last night?” I almost hit the floor. It was John McCain the night after his first debate with Barack Obama. I’m sitting here, twenty years younger, a girl with no college degree. I’m like, “What am I doing here?” I marched into my boss’ office once he hung up, and we got done fighting. I was like, “Why am I here? I don’t belong here. I’m out of my depth.”

She let me wind up for a good half hour, and then she’s like, “Are you done?” I’m like, “Yes.” She’s like, “You’re here because you’re not part of the problem. You’re here because you’re not afraid to call out BS. You have creative solutions. You belong here.” As soon as she said that, I was like, “I’m here because I’m different,” versus always having that mindset that I’m different and I don’t belong. Had I known that twenty years earlier, things would’ve been a lot more comfortable at least and maybe a lot different in terms of growth trajectory as well.

It’s good advice and a story for us to end on. Thank you. This has been fun.

It’s been great. Thank you.

Have a good rest of your day. I look forward to staying in touch.

I encourage all of your readers to connect with me on LinkedIn, @TammyAlvarez, and then you can also find more information at CareerWinnersCircle.com.

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That was fun, spending time with Tammy, getting to know her and hearing more about the work she does and the topic she covers with her coaching clients. It’s also interesting to hear about the business that she’s built, the way that she can lead it from anywhere in the world from Mexico City, the range of different things that she’s done over the years and what she’s learned along the way. If you’re ready to take control of your career, you can visit PathWise.io. If you’d like more regular insights, become a PathWise member, it’s free. You can also sign up on the website for our newsletter and follow us on LinkedIn, Twitter, Facebook and YouTube. Thanks. Have a great day.

Important Links

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About Tammy Alvarez

Tammy Alvarez is the CEO and founder of Career Winners Circle, which offers a comprehensive collection of coaching and training programs designed to strengthen leaders to grow their careers quickly and sustainably. Her spirited “Break all the Rules” approach blends decades of C-Suite experience on Wall Street with a pragmatic, results-based coaching style. She helps business professionals like you create impact so you can love every Monday morning again!

Prior to starting Career Winners Circle, Tammy held a variety of leadership roles at AIG, Bank Leumi, Genesis10, Bank of America, and Compuware. She earned her Bachelor’s Degree in Business Administration from American InterContinental University.