EP: 172 What Authentic Leadership Really Means With Emily Drake

Brave Women at Work | Emily Drake | Authentic Leadership


According to Merriam-Webster, “authentic” means to be “true to one’s own personality, spirit, or character.”


As you will learn during my conversation with guest, Emily Drake, the word “authentic” was also 2023 word of the year. It was one of the most looked up words in Merriam-Webster’s dictionary last year.


And the word “authentic” showed up as a top character trait of executive/leadership presence in a 2022 study referenced in a recent article on executive presence by the Harvard Business Review.


And finally, I recently reviewed my personal and professional values, and authenticity and integrity are two of them. I need to live and work authentically to me at this point in my life. Here’s a quick plug if you haven’t reviewed your values lately. Just like you go to the doctor for your annual check-up, you need to review your values annually. Know your values is so important because it drives clarity, especially when you need to make key personal or professional decisions. Google Brene Brown’s values exercise for awesome tools!


The bottom line is that we can’t get away from authentic leadership!


During my chat with Emily, we discussed:


  1. What authentic leadership means to Emily.
  2. What prompted her to start her company, The Collective Academy.
  3. How we can determine what success means to us and how it changes over time.
  4. How we can avoid career complacency, especially when we hear others encourage us to slide into our comfort zones and stay there.
  5. Emily shares some of the hurdles that she has seen ambitious women face and how to overcome them.
  6. And she shares signs of organizational cultures that don’t foster authenticity and what to do about it.

Listen to the podcast here


What Authentic Leadership Really Means With Emily Drake

According to Miriam Webster, authentic means to be true to one’s own personality, spirit, or character. As you will learn during my conversation with my guest, Emily Drake, the word authentic was also the 2023 word of the year. It was also one of the most looked-up words in Merriam-Webster’s dictionary. The word authentic showed up or popped up as a top character trait of an article I found in the Harvard Business Review that conducted studies between 2012 and 2022 on executive or leadership presence. In 2022, it was the first time that the word authentic appeared as a trait we’re looking for in leadership.

Interestingly enough, in 2012, the word authentic didn’t show up. We are starting to want that in our leaders and in terms of executive presence. Finally, this goes to my personal side. I recently reviewed my personal and professional values, and authenticity and integrity are two of them. What that means is I simply need to live and work authentically at this point in my life. I need to do what feels authentic to me.

As an aside, here’s a quick plug. If you haven’t reviewed your values lately, after this show, go and do and review your values. Just like you go to the doctor for your annual physical and you want to check up on your health, you also need to review your values annually. Knowing your values or simply what’s most important to you is critical because it’s going to drive clarity, especially when you need to make key personal or professional decisions. If you’ve never done it before, I love Brené Brown. Simply google Brene Brown and then google values exercise, and you’re going to find some awesome tools on her website.

From what I can tell, we simply cannot get away from authenticity and authentic leadership. During my chat with Emily, we discussed what authentic leadership means to her, what prompted her to start her company, The Collective Academy, how we can determine what success means to us, how it changes over time, and how we can avoid career complacency, especially when we hear others encourage us to slide into our comfort zones and stay there.

Emily also shares some of the hurdles that she has seen ambitious women face and how to overcome them. We also discuss signs of organizational cultures that don’t foster authenticity and what we can do about it. Here is more about Emily. Emily Drake is a podcast host, a mental health clinician, and the CEO of The Collective Academy, a leadership development firm that works with organizations around the world.

With decades of experience in counseling, coaching, and facilitation, she helps leaders and teams create cultures that foster community, purpose, and well-being. Through her podcast, Who’s Missing? which I highly recommend, she explores the stories and perspectives of people from diverse backgrounds and fields and inspires her listeners to reflect on their own connections and values.

She also produces and leads programs for clients such as Crane Communications, the George W. Bush Presidential Center, and other professional services and nonprofit organizations, where she supports entrepreneurial thinkers, creators, and leaders as they envision the future. Additionally, she was the founder of the Justice Marathon, an initiative to help allies stay committed and accountable to racial justice and societal change. Emily is passionate about amplifying underrepresented communities in business and empowering leaders everywhere. I enjoy this conversation and I’m sure you will too.

Before we get started, if you’re enjoying Brave Women at Work, please make sure to leave a rating and review on Apple Podcasts or Spotify. As I always say, if this show has made an impact on you, whether it’s one show or many. Please make sure to share it with a friend, a family member, or a colleague. Of course, your ratings and reviews help the show continue to gain traction and grow. If you’ve taken a minute and you’ve already left a rating or review, I thank you so much. It means the absolute world to me. I’m giving you a high five and a hug in the interwebs.

Also, if you haven’t yet downloaded one or all of my freebies from my website, check them out at BraveWomenAtWork.com. I have created three for you. The first one is 24 Career and Leadership Affirmations. The second one is Five Ways to Manage Your Imposter Syndrome, and the most popular one is Getting Paid: 10 Negotiation Tips. As you can see, I’m focusing on mindset, as well as some getting paid because who doesn’t want to get paid for what they’re worth?

They are workbook-style guides. It means that you can write in them and you can jot other little notes on the side. They’re completely for you and you can complete them on your own time. If you’d like to learn more, go to my website at BraveWomenAtWork.com and get yourself some freebies. Let’s welcome Emily to the show.


Brave Women at Work | Emily Drake | Authentic Leadership


Hello, Emily. Welcome to Brave Woman at Work. How are you?

Jen, it’s great to be here. It is a Monday coming after a weekend. We call it our Do Nothing Weekends, but it’s really Doing Whatever We Want Weekends. I’m feeling particularly restored and it’s a beautiful day in Illinois where we live. I have complaints and I could go into those but I was balanced. I am feeling excited to talk to you and excited for the day.

Thank you. If you don’t mind sharing, these restorative weekends. What happened this last weekend? Can you share what happened? That’d be fun.

It is all about self-trust for me these weekends. I used to live a very rigid way of approaching a day. I thought because I’m sure you have all the same books that I do that would lead me to happiness. It wound up leading me to burn out. It turns out I’m someone who doesn’t do the same thing every day. I love having the freedom to be like, “Okay, I can trust myself. What is it that I need today? What do I want to do today?”

Once a month, we have these weekends at my house. I’m a step-parent and we’re kid-free on a couple of weekends, which I want to acknowledge. In some ways, it sucks. In a lot of ways, it sucks. There are some benefits. One of them is being able to set aside time. I watched a documentary and had a very rich conversation with my partner about it over dinner out in Logan Square at a restaurant called Giant. The documentary was called Stamped From the Beginning, Ibram Kendi’s documentary about the roots of racism and some surprising facts about how the system was created 600 years ago.

I then played my video game because I have a kid in my life. I’m a new step-parent. They’re nine years old. They play video games. I thought, “I could play video games.” There are so many things that we bonded over, but it’s been sweet as a 44-year-old woman who’s becoming a caregiver for a kid for the first time in my life to be rediscovering some of my childlike interests. I did some of that. When I had moments that felt like, “I’m going to do this,” I tidied up. I made banana bread. Here’s the thing. I don’t want to stick to a schedule. I want the freedom. Independence is my number one value. When I get to flex that, I’m happy.

You’re one of my people. I have two kids as our pod people know, and I love unstructured weekends. I don’t get them as often. I love that you do it once a month. I may take a play out of your playbook and maybe try to figure out how to do that next month. That might be fun. Everybody, we’re getting into it. Emily, why don’t you tell us a little bit about your background story and how you’ve gotten to where you are now in your career?

What Authentic Leadership Means

I’m the proud owner of The Collective Academy, which is a leadership development organization that is merging with another women-owned business, which we’re very excited about. Our organization is all about teams and the senior levels of leadership within a group, and helping leaders lead as better versions of themselves.

That’s what I’ve been doing for the last ten years, which is super cool. I went on LinkedIn the other day because I’m on the board of an organization here in Chicago called Ignite. We’re working on helping young people maintain their dignity while experiencing homelessness and getting them into a stable place, not only from an employment perspective but mentally and physically as well. It’s that holistic approach that I’m fond of.

I was looking back at my LinkedIn to remember when I worked in direct service and social services. It was more than ten years ago. When you asked me, “Can you tell me about your background story?” I bring that up because at this stage in our career and our world and work, when you’re a woman and you’re in your mid-40s, it’s like, “I’ve done a lot.” I am the sum of all of these parts.

I love internal family systems. I’m a mental health clinician. I have the training in a lot of different psychological frameworks. I love Dick Schwartz’s Internal Family Systems because he talks about the parts of us. This is analogous to coaching too. We talk about it as well. I think to myself, there is a part of me. That’s why this weekend was so awesome. I got to sit with parts that I hadn’t thought about in a while; the advocate, the activist, and the creative writer. I was a columnist for Crain Chicago Business during the pandemic. What brings me here is all of that.

Along with the founder of our organization, I saw a need in the marketplace to have audacious career conversations. You and I both probably were climbing a ladder for a good portion of our career and then you’re like, “There’s more ladder ahead, but am I even leaning it on the right wall? I don’t know.” It’s like, “Oh, god.” Once you have that insight and that moment, you’ve got those choices and I know you help people with this too. Are you going to explore it or are you going to ignore it?

I’ve gotten to where I am because I’ve explored more than I’ve ignored and when I’ve ignored, which there’s been two times in my life that had grave consequences, like suicidal ideation and having to kill myself consequences. That’s how ignoring can exacerbate. I have ignored it and it’s been nearly catastrophic for me. I’m on a mission for myself to not ignore that still quiet voice inside all of us and help it become more amplified. That’s how I got here.

We’re going to go off track a little bit, then we’re going to go back on track. I’ve been there. You’re climbing the ladder, you keep going, and you keep getting all these awesome opportunities, and you keep being successful. Everyone’s thinking, “Emily, or Jen, or Amy, or whoever, you’re doing so well.” You then have this epiphany where it sucks because you were in darkness or almost in sweet ignorance before. All of a sudden, you’re like, “Do I even want to go to the next rung?” People are freaked out because they’re thinking, “Who are you”? They’ve known you as this climber for millions of years. What would you say to women who are just opening their eyes and having those realizations? What should they do?

The first thing that comes to mind for me is to do your best to not ignore it wholesale. Not ignoring it and listening to the voice is probably the most heroic thing. The next thing is sharing it. I am always auditing what I call my personal advisory board. The people in my life, I call them an iOS, where if you have an iPhone, you can pin ten conversations at the top of your text message. That’s my personal advisory board.

Those are the people who if I’m going to say a thing, I’m going to say it to them because they’ve been carefully vetted and screened to be not assholes and also truth-tellers. They also know me well or they know me in different ways. Saying out loud that I’ve thought about this other way. I’ve thought about this thing that I used to do that I don’t do anymore.

This is why I love assessments because they get us anchored in what is true no matter what setting you’re in. Whether you’re a zookeeper, a chemist, or a therapist, your top strength of empathy goes wherever you go. Through that, talking about it with myself, which is why I love reflection and journaling, which is increasingly becoming a practice. That’s number one and number two is talking it out with someone else. Let it breathe a little bit and see what it feels like.

The other thing is those top ten people in my life, the number varies from day to day potentially, but stepping outside of that, starting to read, and listen. You’re probably doing it anyway if you’re thinking about it. I think the punchline for me when it comes to what’s my first step is to honor it and honor yourself. There are ways to do that internally and externally that I could go on about.

Part of this is a lot of systems are working against that exploration. Internalized capitalism, gender inequality, and imposter syndrome are all these things that are built so that we don’t ask questions. When you do and you feel like this is scary, that’s where courage comes in. Of course, it is. What will your mom say? What will your boss say? What will your colleagues say?

I’m sure you’ve had similar experiences. That’s what got me so sick. When I was sick and this wasn’t too long ago, it was in 2022, I was living a successful life. Keep going, get bigger, and scale, and then I had to take a leave of absence because I was willing to make the ultimate sacrifice and that wasn’t okay to me. I was living according to the rungs of a ladder that made sense to everyone but me. I didn’t know that. Some of this is self-propulsion. You’re going without thinking.

I have to read this from one of my friends. She sent me a meme and it says, “Don’t forget that every dead body on Mount Everest was once a highly motivated person. Maybe calm down a little in this 2024.”

Right. What are we working so hard for? Have you stopped and thought about it? In service of what? I have no judgment about your answer. I work with lots of high achieving, high net worth, type A achievers, that’s the self-description. There’s a huge movement right now of rest and slowing down and doing less. That jives with me. That’s my constitution, my personality, and who I am.

If it doesn’t jive for you, and you are literally on fire inside with passion and excitement for living at that pace, go for it. I want all of us to stop and ask, “In service of who? In service of what?” If you tell me it’s for a system outside of you that’s not thinking about you one way or the other, I’d ask you to think about it. Be intentional.

You deal a lot with authentic leadership and I think you’re talking about that right now even self-leadership. How do we know when we’re being authentic and listening to that voice and when we’re not, whether it’s with a business? I was surprised by what you said. You’ve owned this business, The Collective Academy, for ten years. Even when you’re in entrepreneurship, you are thinking, “I was going down the wrong path.” It doesn’t have to be in corporate life. When can we say, “You know what? All signs are good, we’re being authentic,” or “All signs are not good, we’re not being authentic.”

The tricky part of this is the answer is different for everybody. This is why I think if you don’t stop once in a while to check in and have your advisory board looking out for you, there’s no way to avoid burning out or being unhappy. I’m unhappy too. I probably feeling six things right now. We’re all complex beings but for me, I can tell you what my watch signs are.

If you don't stop once in a while to check in on yourself, there's just no way to avoid burning out or being unhappy. Click To Tweet

Yesterday, I was looking back at my Instagram stories archive because sometimes I like to ask, “What was I doing two years ago today? That’s so cool.” I didn’t post anything for the entire months of February, March, and April 2022 when I was sick, in treatment, fighting for my life, and living with my mom.

Who else was I going to? Provided you like your mom and she’s alive, that’s where you go. I realized that’s a gift that I had those two things. That’s a watch sign for me, disengaging and you know, depression, a hallmark is isolation for a lot of us but for me, it was truly receding from the world. I wasn’t posting anything, I wasn’t engaging online. We can say what we want about social media, but that was my relationship with it/, I find it joyful and I wasn’t doing it. That’s one.

The other was I wasn’t listening to music. Part of my watch sign for me now is if I’m not engaging with the arts, typically for me that’s going to be music, more than movies, more than books. What’s going on with me that I can’t be present for music? That’s one for me. The other is being irritated all the time. We all get annoyed, but when identifying my values, this is the step before all of these. I know you’re going to love this because I know you believe it too. Not only believe it, I’m sure you live it. These are my values. When these are in conflict, I get sick and that’s the truth.

Independence is the top one for me. If I can’t have that, which is very different than freedom, solitude, or autonomy. I define independence as going with the flow at my pace. I could be with someone, that would be fine. It doesn’t mean that I’m alone. I’m coming around to this many different ways, but the audience is not going to love it. It’s different for everybody what authentic living means for you and what leading as yourself means for you, and then deciding if it’s safe to lead as yourself in any given environment.

I think about that specifically with women and with people of color. To be who you are is courageous and to define what that is is courageous, and then to go public with it, there are a lot of risks. There’s a risk that by saying “I’m not going to take meetings after 05:00” I won’t be included in projects. As a woman, in particular, I’ll be overlooked for promotion. I know you talk a lot about this on your podcast and you know this as much as I do, living within my values is inconvenient.

It’s not always joyful like it was this weekend. That’s what authentic leadership means to me. It’s a life-or-death matter for me. I’ve proven that to myself now. I don’t need more evidence. You have to decide what it is for you and then meet wonderful people like me and Jen who will support you in that challenge.

Brave Women at Work | Emily Drake | Authentic Leadership
Authentic Leadership: You have to decide what authentic is for you and then meet wonderful people will support you.


Not diving too into detail, but with 2022 being such a rough time, was that a repeat for you, or was that the first time that you were thinking, “I’ve hit some bottom and I’m not living in accordance with my values?”

It was a repeat. It happened once in 2008 when I was working in public relations. I had reached a level in my career that had very finite and indefinite, in some ways, rungs to this ladder. I think we both brought things into the equation, but an abusive person. I also was a person who was like, “I don’t quit things.” This is me before. I don’t quit things.

I’m not sure what value that was in security. I don’t know, but I wasn’t a quitter and whatever that meant, and I’m sure I can thank my mom and dad for it in some ways. It took my mom and my ex-husband intervening and saying, “You’re going to leave this job.” I had gained and lost 50 pounds in a month. I wasn’t sleeping. That’s another big watch sign for me.

In the shower one day in 2008, I think it would be better not to be alive. I had never had that thought before, so I quit and I began rebuilding. This last time was sneaky. I was working hard if you looked at my calendar back then. I looked at it now and I thought, “What was I doing?” It was a lot of hustling and not slowing down to audit and to feel. I wasn’t sleeping then either.

If anyone out there struggles with insomnia, you’re not alone. It is a serious illness and it’s something to pay attention to. At the same time, you put a gun to someone’s head and you demand, “Sleep.” They’re not going to be able to sleep. It’s a chronic thing and it’s crippling. I’ll say this, I identify as a plus-size woman. I’ve been a plus-size girly my whole life except for two times when I was able to get to a smaller body size. I was in both instances, the sickest I’ve ever been. That also correlates to these two instances in my life.

There are a lot of systems at play there. I know we’re not here to talk about fatphobia. We’re not here to talk about necessarily body image, but I will say starving myself was detrimental to my health. All that is to say this was the second time. Some things were similar. The difference in me still being alive right now, at least as far as I can ascertain because who knows, was being willing to ask for help.

The first time I wasn’t, I had to be shown the way. The second time, I was in the community to know myself enough at 42 to know that this is not what I want to do, and I don’t know how to help myself. As an entrepreneur, I reached out to my corporate clients and I said I was taking a leave of absence, then I went to treatment. It’s wild because my business partner, we’re emerging businesses this year, specializes in individual coaching. She’s also taken a medical leave of absence. That’s why it’s there for, folks, to take the time.

The Collective Academy

I appreciate you sharing that. I had to take a medical leave in 2019. You see the common thread, everybody. When you’re ambitious and hard-driving, there is that risk where you can light yourself up. You start to singed a little and then you need to take that break. You’ve mentioned a couple of times about your board of advisors. That isn’t always common. Not all women take the time for this. I think it is so critical.

They might have a friend whom they met at a PTA meeting or their kids after school program or whatever, but I still think that being an adult can be lonely. Being a working woman can be lonely. How would you recommend if a woman doesn’t have those people pinned at the top? How she could start reaching out and getting that community?

A book came out. I have not read it. I love doing this, “A book came out,” and then I have nothing to say about it. I’m going to bring it up because this is a very common predicament, especially women and I’m sure men too, but let’s talk about women because that’s who we are. The book is by Rhaina Cohen, The Other Significant Others. The subhead is Re-imagining Life With Friendship at the Center. This is a cultural conversation that’s happening a lot in the circles that I run in; professional women, women who may have kids who may not, women who are in partnerships, and reorganizing what we prioritize.

The running joke is that we have to book out eight weeks to see a friend. I think there’s a collective frustration around it but it’s by design. There’s a lot that’s asked of us, and Eve Radsky is my go-to to talk about leveling the playing field, especially with emotional labor at home, especially in heteronormative relationships. We don’t have time for friends and for engagement in a way that is enjoyable and not necessarily driving towards something other than developing really strong relationships with people.

I would love to say to the audience that it’s a shared experience, especially if you’re looking to connect with other women, we are all stretched. Here’s the thing, I laugh when I tell people I play video games especially when I’m working in these huge multinational companies. I know what they’re going to be thinking. It’s not what they say but it’s, “How do you have time for that?” We all have the same amount of time.

I think the point is if you have kiddos to raise or if you have a partner or spouse or an ailing parent, what slot of time can you give to nourishing those relationships? Who is going to reciprocate? Reciprocity is one of my top values. I’m not going to chase anyone down, but I am going to try. That mutual effort, I’m hearing from a lot of my friends. I talked to one last week. I stopped by to drop off a Valentine. She was asked, “You have a minute?” I answered, “I do.” We had a spontaneous coffee. She’s not maybe on my personal advisory board, but she’s someone I want to have a relationship with. It takes time.

I think if you have kids at home and you have a partner or spouse who is not supportive, who doesn’t maybe pick up some of the tasks and work at home like Eve Rodsky talks about in Fair Play, which is a whole system on how to equalize things a little bit, you’re not going to have the friendships you want. You’re not going to have that personal advisory board because it’s not going to happen. It takes a lot and it’s a huge privilege for me to have the ability to nurture those relationships, but I also don’t do it perfectly.

I will tell you this, as you said, you book with people six weeks out or whatever. It’s interesting. I do schedule my conversations and put them on the calendar. I know that may sound so not organic and like, “That’s not real.” No, it is real. I’ll be saying, “Okay, Sunday, 7:30. What time zone are you in?” I’ve got friends on other coasts and things like that.

I put it on the calendar and my husband is amazing. I know that not everyone has a partner. You might be a single parent or you have an ailing parent or family member. There are all these other machinations of lifestyle, but my husband is great with and I’m blessed in this case that he sees it as an appointment on my calendar.

Sometimes I may have to cut it short, I’ve got a five-year-old in my face or whatever. “Mom, mom, mom.” That kind of stuff but it doesn’t matter because I’m making the time. I love that you share that because it does take effort but I will tell you, since my burnout, I’ve put a lot of effort into the community.

It’s multiplied and brought back to me tenfold in terms of support, enjoyment, and laughter. I’m not saying that my partner, my spouse doesn’t support me, but this community also supports me. Even this podcast community The Brave Woman at Work supports me differently and enriches my life. It does take time. It does take effort.

It does like everything else. If you are tuning in and you’re in a place of, “I haven’t talked to any of my friends in two months.” That’s fine. It’s okay. There is no chasm to cross to begin, other than what we come up with in our minds, like all the stories. I say this to people all the time, especially when I’m talking about mentoring and sponsoring, reaching out to ask someone for their time.

Be intentional and purposeful about it, but most people want to help and are willing to do that. Especially, you’re talking about friends. I’m also talking about friends. I think it takes at least one of us to say, “I love you” first. One of you has to reach out. bBe the person and fumble through it. It’s far better than sitting in shame of, “I should be better.” We’re all struggling and it’s beautiful and we can laugh a little about it. That’s how you know who your people are.

Be intentional and purposeful about asking people for their time. But most people want to help and are willing to do that. Click To Tweet

Avoiding Career Complacency

Glennon Doyle always said, “Life is brutiful” It’s brutal and beautiful at the same time. It’s cool to admit that like we’re all in this difficult soup together. We all have to wade through it all together. Some of the things also that I know you cover a lot are leadership, career advancement, complacency, and all this stuff.

Life is beautiful, but it's really cool to admit that we're all in this difficult soup together. Click To Tweet

One of the things I’ve experienced recently, and I wanted to dive in with you a little bit, is that even in my own family. I love my family and love you all, but I’ve talked to people and they say, “I’m going to hang here because things are the way they are and things are good,” but I can hear in their voice a complacency. Remember, I have to be careful because I could also be that person who’s climbing Mount Everest to my death.

There’s a spectrum and sometimes I lean too far in that Mount Everest spectrum, but I also refuse to become complacent and I’ve had people encourage me to become complacent. I wanted to have you give some wisdom there. If someone is feeling it’s in their career, it’s a leadership situation. It’s like we keep talking about that complacency.

Any thoughts about that? Should they hang? Should they not hang? When do they know to stay or go? I think that especially in our 40s, a lot of people and I’m not judging, get to a complacent point in their careers. They’re thinking, “I got fifteen years left.” Or, “I got X years left or whatever. I’m going to tick down the days.” I don’t know about you, Emily, but I can’t live like that. I wanted you to comment on that.

The first thing I hear is I want to affirm in your self-awareness like, “I can’t do that. Me and Jen cannot do that.” As you said, no judgment on whether someone is being complacent or too satisfied with themselves or a situation, or if they’re at peace and have to keep this like it is because they’re not complacent with all the things you mentioned or we’ve been mentioning, like caring for a parent, caring for kids, and caring for who knows.

Thank you for checking your own judgment. I do it too, because of course, the people I love most, I talk to them in my head the way that I talk to myself. That’s the voice. That’s the voice that got me sick, “You don’t quit. What are you doing? You keep going,” and then we’re dead on a mountain. The advice that I would give is that life is a series of decisions.

I think there are something like 35,000 choices we make every day, whether we realize it or not. It’s a lot. You can decide at any time to not be satisfied with yourself and want to do something different. I had someone on my podcast last season who talked about her decision to leave Big Law and the distance between the decision date and the actual time that she left. It was a year.

This thought of if you want something to change, I love talking about micro-movements. Taking like a different way to walk to work or choosing a different ice cream flavor. We’re all so attached. For me, it’s Moose Tracks. It’s hard for me. What if I walked into a restaurant, Jen, and they were like, “Our strawberry ice cream is the best in the county.” I feel like I should probably try strawberry.

All that is to say, I love it when I’m facilitating with groups, asking questions like, “When’s the last time you did something for the first time?” I think that’s what you’re getting at. I come around to complacency. Whenever I come up against that, I know what you mean when you see someone and you can feel it. They don’t like this. It’s not that they’re choosing this. They’ve just found themselves here. It’s to get curious about it.

For me, inspire that voice somewhere in there that’s like, “I am a person of parts and there are things I’m capable of. I can flex. I can do that. I can try strawberry ice cream.” I don’t fault anyone for being able to get through a routine, especially now. One thing that puts my hackles up is when someone is living with depression.

For example, they say, “Go for a walk.” Yes, of course, and the world’s on fire. A lot is going on. All that is to say I love your generosity of spirit with complacency. I love your clarity on, “This doesn’t work for me.” It’s not aligned with my values and then when it comes to someone in front of me, who might be saying that? Let’s lead with curiosity and ask how can you flex in one way or another.

What’s important to you? One of my partner’s top values is security. To me, it can look like complacency, but to him, this is security. This is why I show up for this job. This is why I haven’t changed jobs. This is why. I’m like, “Okay, good for you.” You said it too, Jen. The punchline is, “You do you, and let me help you explore it if you want to.”

That makes total sense. I should have asked you this before because we’ve never mentioned IFS. I wanted you to leave some resources here for people too. For Internal Family Systems, can you double back for me and redefine what it is, you mentioned who founded it and any resources. If someone was like, “I tuned in a couple of minutes ago, and I want to dive on IFS.” Where can they find info on that?

Internal Family Systems, the homepage is IFS-Institute.com. This is where all of Dick Schwartz’s work is and everybody who’s connected in his sphere as practitioners. The core idea of IFS is that every one of us is a system of protective and wounded inner parts. Led by a core self. These inner parts work together and we express ourselves in a certain way but this self is in everyone. It can’t be damaged. It knows how to heal.

That core self is what IFS gets to. Of course, there are parts of me, honestly. I had this experience the other day where I didn’t feel included and my feelings were hurt, “You want to talk. Let’s go there.” That is a core wound of mine, “I don’t matter. Nobody sees me.” While I was able to honor that protective and wounded part, the core self is this person who loves independence, leads with authenticity, and is great at relationship-building.

I have to live with those parts and instead write, this is a real watchword for me, whenever anyone says, “I want to get rid of this part of me.” I’m like, “I know, right?” It would also be great if someone could tell me what to do next. All these things, but it doesn’t work like that. I think IFS is if you’re already going to therapy, chances are your therapist has at least a passing awareness of IFS.

I love it because it focuses so much on the integration of self and also acknowledges that we all, literally all, your CEO, your kids’ teacher, all of us have those protective and wounded in our parts. What would it be like to try to look at the core self in addition because that’s a thing I’m sure you experienced too? It’s so easy to be focusing on the things we can’t do.

I had a call with a woman interested in coaching who lives with ADHD and OCD. I’m starting to take a real interest in neurodivergence in the workplace. In the first five minutes, she was able to say, “These are all the things that I’m not good at.” I said, “What are you capable of because of maybe how you think?” There’s a great 17-minute video or something that tells you all about the system. Probably not particularly interesting for someone who isn’t necessarily getting clinical training. I think it’s worth watching at least that video to understand a little bit more about the theory, and Dick Schwartz is great.

I’m not clinically trained like you are, but I have talked to people about it. I’ve gone through IFS therapy myself and it’s super helpful because when we start talking to those other parts, we think, “That’s where that behavior comes from,” or “That’s why I feel the way I do.” I don’t know. I think for me, it brought more clarity that I thought, “That’s where that’s coming from.” I don’t know if that resonates with you, Emily.

Overcoming Hurdles

Yes, absolutely. It didn’t pop up and I know you talk a lot about imposter syndrome. Imposter syndrome didn’t show up in your life. This is a part of how the world works, that there is, at least from my vantage point. Reshma Saujani and everything she’s talking about now, there are systems set up that it’s hard to live as yourself and to have confidence.

To proceed with confidence when there might be systems inside of an organization or inside of a structure that is invested in you not being confident or you not having as much of a say. It’s all this stuff working together that I think you and I are excited about because it’s so compelling to say, “It’s my fault.” It’s not that easy.

It’s not that easy. I think everything we’re talking about is universal. I always tell people that the most confident person is also faced with or is facing imposter syndrome. They may have learned how to manage it better or differently or whatever but we’re all in it together. Remember we talked about this at the top of the call.

Brave Women at Work | Emily Drake | Authentic Leadership
Authentic Leadership: The most confident person is also facing imposter syndrome. They may just have learned how to manage it better.


At the top of our conversation, we’re all in this rough soup together. I want to make sure that the audience knows about your business and what you do. I don’t know if you’re still with the Crain’s Leadership Academy. What kind of services do you provide with The Collective Academy in case someone is interested in looking you up and diving in and learning more?

If you are a decision maker or someone within an organization that’s interested in bringing more emotional and mental health into your organization in a very practical, tactical way, we are great at multi-session experiences that create community. A lot of organizations will bring us in when there’s new leadership and they want to build trust when there is a group of individuals moving into a senior level of leadership and they want to make sure they have what they need. We move beyond skill building.

We’re passionate about making sure that everyone in an organization becomes the better version of themselves and doesn’t slack off even when you’ve, “Arrived.” That’s the bread and butter of what The Collective Academy does. The Crain’s Leadership Academy sunset a few years ago, but we had probably twenty different sessions of that across the country, which was wonderful.

That program, the skeleton of it is the whole methodology of The Collective Academy, which is bringing together people who have different perspectives and backgrounds, introducing them to experiences they’ve never had before, and learning as a result of that, especially from sources that they haven’t considered.

We’re huge fans of bringing in social influencers, nonprofits, artists, and musicians because leadership comes from every angle, which is what my podcast is about, Who’s Missing. That’s what we do and then you can also reach out to us. If you want to bring us into your organization, reach out to us, and then you can also reach out to us if you want individual coaching. We do leadership coaching and career coaching. It depends on who’s paying for it. The business or you? By the way, get your company to pay for it if you can. We can help you with that if you want to know how to do that.

That’s cool. One other thing that you mentioned was assessments. Do you guys have any favorites that you use and why?

That’s a good question. I think assessments are great and they’re a great tool. You take what you need and leave the rest. Do I have a favorite? No. Do I have several that we use? Yes. CliftonStrengths, everything DISC, the Enneagram I’ve used with people, Hogan. I always ask people some sense of, “Who are you?” Depending on how they answer that question, which tool might help you go a little bit deeper?

Most of the time though, I use assessments in my individual work to affirm people who are thinking, “What’s wrong with me?” I’ll say, “Nothing.” I know you’ve been told that your whole life, but you happen to be a dominant style. That’s productive. Maybe you soften the edges this way. That’s why I like to use them but they’re great. I also like astrology. Whatever gets us talking.

You and I will have to chat about that because I’ve been into that too. It’s like you bring in all this stuff, you bring in the charts. Whatever’s going to help you. Who cares? What are one to two ways that you believe women can be braver at work today?

Asking for what you need is one. I can tell you in a room of 100 women in automotive I was with last fall, I asked, “How many of you are good at asking for what you need or asking for help?” Three people raised their hands. Identify it and ask for it, and then ask for it again. Keep asking for it. The other thing is not being afraid to speak up in general when you have an idea.

Identify what you need and ask for it. And then ask for it again and keep asking for it. Click To Tweet

Once you know your strengths, use those strengths. What I love about assessments is the affirmation foundation, “You are good. You are worthy,” and then being able to pull up to a table and say the thing. That one’s a little more squishy than my first thought. I wonder what I would say. What’s coming up? What would you say?

I do think speaking up is a big one for me. The ability to speak up and stand. I don’t know if this is the same or different, but standing in your power, which goes to your assessments. Maybe that’s the second one. Once you know, and there are so many of us, I’ve been such a geek about assessments my whole career.

I’ve always loved it because it was like looking into a lens about me so that I understood how to leverage and then stand in my power, which I talk a lot to clients about, “If it’s a no, then it’s a no.” Stick the landing. In an interview, what is that point that you’re saying, “This is why you should hire me?” All of those moments where I’m envisioning Wonder Woman right now, where you can stand confidently in your strength. I would tell you that any time that it makes sense for you to do it, I would say do it.

For you to do that, you may need to do work that we’re talking about, like taking an assessment, understanding your values, doing IFS, or whatever resources we’ve shared, read books. We all know that if you’re here, you are interested in that development. I think that it is all critical to do those two things. That’s what I would say if someone asked me that question.

I love it. Thank you. This is one quick thing, have a playlist. This is a woman who loves music, plays music, and plays an instrument, it’s my go-to, whatever that is. The works of art that you love or books. I think the personal advisory board can be people, but it also can be people you never meet, like your favorite band or your favorite artist. Maybe it’s Brené Brown if that’s your guru, so to speak. Maybe it’s Jen, you know what I mean? Be brave by being around bravery. Curate your life, curate your experience. I think that’s possible too.

That’s cool. Maybe when one of my social posts, you and I could wrap on a power playlist for women, that’d be super fun. Where can women find The Collective Academy online? I know you guys are going to have a merge of companies. What’s that going to be? Is it going to be the same? For now, where can they find you?

For now, we’re at Collective-Academy.com and you can find me on LinkedIn. It’s super easy. I would say go there first. If you want to see what I’m thinking. If you want to see what I’m doing, I’m over on Instagram. You can check me out personally. The Collective Academy is over there too, but I’m @Emdrake. It’d be great to get to know you however you find me.

Emily, thank you so much for being on the show. It was so much fun. We have a lot in common.

I had a blast. You’re good at this, Jen. Keep doing it.

Thank you.

That’s a wrap-up of my discussion with Emily. I hope you found our conversation both valuable and inspiring. Here are a few questions to consider or journal on until next time. The first one is, what does leading authentically mean to you? It may be different than what Emily and I discussed here, or there may be slight nuances. Being clear on what this means for you is important.

The second question is, what does success mean to you at this moment? Maybe success from a year ago is different from success today. Jot that down. Finally, be honest with yourself. Are you living or working from a place or state of complacency right now? Why or why not? You know what I mean. Complacency is a period of your life where maybe you’re stuck in your comfort zone or you feel stuck or frustrated and you don’t know what to do to move forward. Jot down some ideas, think of some ideas.

What are some small steps or what is one small step that you can take to break free from that feeling of stagnation? As a reminder, please rate, review, and subscribe to the podcast on Apple Podcasts and Spotify. The show is also available on any other podcast platform you enjoy. Until next time, show up, be authentic in your leadership, and be brave.


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About Emily Drake

Brave Women at Work | Emily Drake | Authentic LeadershipEmily Drake is a podcast host, a mental health clinician, and the CEO of The Collective Academy, a leadership development firm that works with organizations around the world. With decades of experience in counseling, coaching, and facilitation, she helps leaders and teams create cultures that foster community, purpose, and well-being.

Through her podcast, Who’s Missing?, she explores the stories and perspectives of people from diverse backgrounds and fields, and inspires her listeners to reflect on their own connections and values.

She also produces and leads programs for clients such as Crain Communications, the George W. Bush Presidential Center, and various professional services and nonprofit organizations, where she supports entrepreneurial thinkers, creators, and leaders as they envision the future.

Additionally, she was the founder of The Justice Marathon, an initiative to help allies stay committed and accountable to racial justice and societal change.

Emily is passionate about amplifying underrepresented communities in business and empowering leaders everywhere.

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