34. An Essential Intervention with Elena Aguilar

SPEAKERS

Greg McKeown, Elena Aguilar

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Greg McKeown 

Let’s start from the beginning.

Elena Aguilar   

Yes, my name is Elena Aguilar and I am a writer. I’m a coach. I am an educator, I founded my own small business. I work on topics that include team development, emotional resilience, racial justice, communication. But more than anything, I’m a writer.

Greg McKeown     

And what do you write?

Elena Aguilar     

So I have written six books about the topics that I just listed. And those are specifically for educators. I worked in the public schools, I live in Oakland, California, and I worked in the public schools here for 20 years. And so I have written for teachers, school leaders, school coaches, for about a decade now.

Greg McKeown   

You emailed me. What did you say? How did we get here?

Elena Aguilar     

I just have to first thank you for your work. Because when I first I heard you first on a podcast, and I remember literally stopping in my tracks, I was doing something like cleaning the house. And I just remember stopping and feeling like I was having one of those epiphany moments.

So I started my own business about six years ago, in part because I wanted to keep writing and I, I sort of needed to have a structure around me to, I don’t get paid much at all for the books that I write not in the field I’m in and so I needed some way to have the other revenue streams. But that business took and has taken on an enormous life of its own. And I find myself over and over saying, sometimes in the form of sort of a temper tantrum at the end of the week, or on a weekend, like I just want to write, I want to be a writer, I’m a writer, I want to write and, and so I mean, this is my primary dilemma that I go around and around, and I read so much, and I listen to so much. And I want to write books, but there’s so much that feels like you have to do to get your book out there. You have to do keynotes and workshops and Q+A and you have to write other articles and blogs so that you can get the word out so people learn about you. And you have to do social media and podcasting and newsletters, and it feels like I have to do all of that to create and maintain and expand my platform. And all of that eats away at my writing time.

Greg McKeown     

You’re describing a true calling, true passion around the writing itself. That’s what you want to be doing. That’s what is important to you. That’s where you feel your clearest contribution. But there is this mighty other whole cloud of activities that are supposed to support that effort. But it’s a bit like the tail wagging the dog. The other becomes the work and the writing is actually taking a smaller percentage of your time and attention.

Elena Aguilar     

I’m really clear on my sense of my own mission or purpose in life. I’m really clear on what I do best I’m clear on it feels like what is essential to me. And I just keep going around and around. And then of course, having a pandemic hasn’t helped because that completely well it shattered my business and then I quickly restructured it, and it’s okay. But it, I used to do everything in person. And, and so just when I felt like I was sort of getting a hold of this monster, and I could actually get into the writing, then we had the pandemic. And so and then, you know, and now it’s been five or six years. And I didn’t list also that when you do all of these other things, and you have a business, then you also have to run a business. And there’s all there’s so much to do. And yeah, I’m just like, what do I do?

Greg McKeown     

Yeah, the way you asked that question. It’s not like, surface. You’re not kidding around. There’s some emotion behind that. There’s some pain behind that.

Elena Aguilar     

So I turned 50 a year ago. And I feel like I have a dozen more books in me. And I have books that are in different genres. And I want to write for a broader audience. I’ve learned so much in my life, and especially in the work that I’ve done in the last 25 years in education that is relevant outside of education. And there’s been interest. And so, I feel like I am reaching an age where I recognize that I can’t take for granted. I mean, you can’t at any time, but it’s sort of feels like 50 feels really big. It’s a big number. And, and how do I get the time to write these books? And how do I you know, and there’s another part that I have to mention, which is just the realistic part of earning a living, and I have a, I have a son, I have a partner, a husband, who’s an artist, and he’s following his passion and doing incredible work. And but we don’t have big income streams that, you know, have to figure out the income piece. And, and so it does, it feels more intense than and feels more charged, because I don’t want to be trying to create brilliant Instagram stories, as much as I have been.

Greg McKeown     

Yet you, you’re describing a challenge where the money pressure comes like a tiger. Meaning it lurks all the time. It creates this burden. Fear really, even when things before the pandemic, were starting to work in the business, or even were working well. You still have this frustration. You are keeping me from writing? How am I supposed to write when there’s a tiger lurking over there?

Elena Aguilar     

Yes, that is definitely true. I love that analogy. And I also want to acknowledge that or just want to bring into it that I knew that when I wrote my first book, I needed to do a lot of the marketing I needed to be getting out. And I did that because I wanted the book to have a life and I wanted people to read it. And since then I’ve known that I have a very deep commitment. I mean, my primary commitment is to impact and to, to doing what I can do to get my work out because I know that it helps it’s in service of a greater good. And, and so a lot of what I’ve done, I’ve done because I wanted the work to get out. I think it’s more recently this year 2020 turning 50 thinking about my son’s college that I’ve been thinking, you know, I’ve been working at this business in this writing for seven years now and sort of okay, I need to actually have a bigger savings account. This is real now. I got to figure this out.

Greg McKeown     

There’s urgency to it. What you’re really I think telling me is, this writing hasn’t got to the place I want it to get to it, I’ve made progress. I have put my ideas out there that’s helping. I’m building this platform, but I feel somewhat stuck in the journey. I want it to reach a new tipping point a new audience, so that so that I can provide better so that I can fund college for my son, so that so that all of it adds up to urgency. And in that urgency, frustration, too.

Elena Aguilar     

Mmhmm.

Greg McKeown   

And I think, in your voice, that weariness. I’ve been doing this for years now.

Elena Aguilar     

Yeah, and it, you know, it feels like, there are so many decisions that only I can make, as the CEO of my company, as the person writing the books. And, and there’s weariness, I have had a lot of impact. And I’m so grateful that I’ve been able to reach the people I’ve had, I have folks around the world who read my books and send me emails, and that’s incredibly rewarding. And, and then I think, and it’s been exhausting. And I thought I had all kinds of plans for 2020, which were about scaling back and working, you know, four days a week, and so on. And then and then 2020 happened. And, and now, for example, here’s a present current day dilemma. I was asked to do a keynote in the end of January, that’s on a Saturday morning, and it would start at 6am pacific time because it’s on the east coast. So I would need to be up at 430 or 5 and delivering this keynote at 6am on a Saturday. And part of me wanted to just say, No, I take the weekend off. And then the other part said, I can’t say no to that kind of money. I can’t say no. Are when do I say no. And I’m the person even though I have a team of people. And uh, but ultimately, it’s my decision.

Greg McKeown     

It’s a great example of the awfulness of tradeoffs. Mean, I’ve written a decent amount about tradeoffs. But it doesn’t make them more enjoyable for me. It doesn’t make me suddenly always rejoice in them. There’s an inherent pain, you want to be able to take Saturday off, and have this keynote and get paid for it. And right now, the trouble is, everything’s taking a bit more of you than there is to go around.

Elena Aguilar     

 Yeah.

Greg McKeown      

Let’s try and get concrete about what success looks like for you. How would you know?

Elena Aguilar     

I think, okay, I would know if I could easily say, I don’t want to do that keynote. I don’t need to I can say no. Or I can say if you guys really want me to do it, you’ve got to figure out a way to do it on a weekday. I wouldn’t feel like I had to. I wouldn’t feel like I couldn’t turn down that because of the money at this point.

Greg McKeown   

What you just said to me was that you’d be in a financial position to pick and choose what work to do, and when. And I think what you may really be saying is that my writing business is successful enough that I can write for a living, rather than coach for a living. Or at least that they’re both in play. So that, again, you have the option. You still want to coach you still want to speak there’s, there’s a portfolio here of the right balance between them. But right now, right now, it’s just whatever the money is. That’s what I need to be doing. However tired. I am, whatever’s going on. That is the default priority. You wish it wasn’t?

Elena Aguilar   

Yeah, that I would have the choice. It feels like I don’t have the choice. I don’t have a choice right now. And I don’t I don’t know when. I mean, I think the unpredictability of the really the economic situation that we’re in is what also makes me think, Well, you know, if I say no to this, maybe that’s fine, because there’ll be enough offers there’s enough work in the following months. But at this point, I still feel like who knows what’s gonna happen in this economy?

Greg McKeown     

Let me ask you this question, what really is the dream, just describe like perfection for me.

Elena Aguilar     

I would have months when I didn’t have to show up in the public world. And I could completely immerse myself in a writing project. And I don’t mind I usually have written very intensely, as well as working at the same time, but then the book comes out. And then I don’t work on a writing project for about six months, and I just help the book go out into the world. And I, I get away from the screen, and I enjoy that. And then I go back to writing, I think. But I think I would have, but during the time, I’ve written my last books, almost all of those books I wrote, while simultaneously having to present and go out deliver workshops and keynotes on the same day. So I like to write early in the morning, I get up, I would write for three or four hours, you know, finish writing at seven or eight in the morning. And then I would go out and work a full day, and I’d write on the weekends and I’d write. And so I wouldn’t have to do two jobs at the same time, I would just get to write and it’d be immersed in it. And I wouldn’t have to, I wouldn’t have to do Instagram stories, and I wouldn’t have to write newsletters, or I would just get to, I love writing, it’s my favorite thing. Like it’s I it’s rarely painful, I love it. And, and I would just be able to be completely immersed in it. That would be that would be the dream. And I would earn enough of a living to not have to worry about the fact that I was doing that.

Greg McKeown     

It sounds like if you could get your writing career to the next level, if you could have the books be more successful than they currently are. And they’re already, you’re doing great with it. But you want to go to the next level, that that would enable the kind of the real dream that you want to be pursuing. Does that sound right? Yes. Maybe we should spend our time focused on that for a moment. Because something that keeps getting my attention in this conversation is this idea of I’ve got a dozen books. And I’m not saying you don’t. But the thing I want to say to you is, what if you could only have one, but that you are going to do it so right that it’s going to reach 10 times 100 times 1000 times 10,000 times more than the all the previous books. And to challenge you to actually crack the code on, like, what is it that’s going to help you to get to that next level. There’s a lot of people within the writing industry that I know a little about. But also, in every industry that keep putting poles in the tent of their career of equal height. There are already 10 poles in there, and they want the tent to go higher, but they just keep on putting more poles of the same height in it, instead of what’s the one pole that’s longer, that will actually take me to the next level. I wonder if there’s a way we could rethink, reconfigure how you’re doing the books, so that you can have one that you say that just took off? That really worked, and it’s given me a whole new platform, your thoughts on any of this?

Elena Aguilar     

Yeah, that makes a lot of sense. I hear you. That’s a really interesting way to think about it.

Greg McKeown     

You sounded burdened as I said that to you.

Elena Aguilar     

Hmm, no, I actually was feeling relieved. I think I like that. Yeah. I mean, I, that makes so much sense. And I you know, I also Yeah, no, that makes a lot of sense. And it sort of sparks all kinds of little connected ideas. I think it’s just Okay, so then it’s this is I have unanswerable questions, because then it’s how do you crack the code on what that book is? And? And nobody knows the answer to that but I think I can’t think about that question with the kind of with the tiger lurking. I can’t like I won’t get clear on the answer to that question. If I’m feeling like I’m trying to figure out the answer to the question because it will serve a purpose that is very narrow.

Greg McKeown     

You’re saying you don’t have space. Because of the financial pressure, you don’t have the emotional and mental space to even be able to consider the answer to that question.

Elena Aguilar     

So I feel like in some ways to connect with the part of me that has figured out what is the right book to focus on, I need to extract the anxiety around the financial pressure. Does that make sense? Like, it’s like, it’ll pollute my thinking and my intuition.

Greg McKeown     

Help me understand that. You’re saying that just worrying about financial concern is going to make you write the wrong book, you’re not going to be as pure in your writing?

Elena Aguilar      

Well, maybe it’s not as black and white. But kind of like, I think it would make me feel, I think I would keep chasing my tail in a circle. If I just try to think about, what is the book that I could write that would, you know, that would do really, really well. And that would even whether it’s the book does well, or brings in audiences that can pay more than what educators can pay for a keynote kind of thing? Like, if I just tried to think about that, I don’t think I don’t trust that I’ll land on the bright idea.

Greg McKeown      

You’re saying that that question feels like it would take you out of the sweet spot that you’ve been in as you’ve been creating in the past?

Elena Aguilar 

Yeah, yeah.

Greg McKeown     

So I have a couple of thoughts about that for you. One is, what do you think, is the way to increase your impact, therefore increasing your ability to make writing your primary work, and also increased the value, the perceived value of your keynotes and coaching to other people?

Elena Aguilar 

So what do you do when you see three possible paths?

Greg McKeown  

What are the three possible paths?

Elena Aguilar 

Well, let’s say like you see, three. So I have outlines for what three or four different books right now?

Greg McKeown     

Go, what are they?

Elena Aguilar 

That’s like, talking about a pregnancy in its first week. Okay, so I wrote a book about how to build resilience and educators. And it’s done. It’s, it’s got, you know, I know a lot of people are writing about resilience. But I also own that I have some unique ideas and unique ways of approaching it. And that book has done really well. And I have been asked people have, have shared that book with folks outside of education. And those people have said, you know, you should write something for parents, or you should write something for CEOs or you should write. And so there’s interest in a book on cultivating resilient teams, on how do you build a resilient team? How do we, for lack of a better word right now, sort of a problematic word, but how do we unify and come together and connect around our mission and I know that there’s books on this already out there. And I also again, recognize I have some unique approaches. And so that that’s a that’s a project I’ve been thinking about.  And then I have ideas for books that are for much narrower, specific audience and so for example, I do a lot of work around racial justice. And so I work with a lot of people of color, I identify as a person of color. I do a lot of coaching and resilience building and people of color. And so that’s another area that people have asked me. How do I as a person of color, what is different for me in terms of building my resilience? How do I? How do I get rid of the internalized racism that that I’ve ingested in my lifetime? So then there’s a very specific audience there. And then, I’ve been working on something that is much more personal and creative, and mixes history and memoir and social science research, and that that’s a project that I think is has real potential.

Greg McKeown     

But that one, I didn’t understand what that was.

Elena Aguilar 

No, cuz I don’t want to talk about it yet.

Greg McKeown   

Which you don’t need to feel forced or pressured to talk about it.

Greg McKeown 

Of the three, if you had to choose one, right now you would choose which one?

Elena Aguilar 

Okay, the last one that I really think about.  

Greg McKeown     

So now, I don’t want to tell you, that’s gonna make this conversation trickier. But I do understand something of, of how precious ideas are in their early stage and how one wants to protect them. And, and not just announced these things, and I do understand that hesitancy. Why is it that that is the idea you want to run with?

Elena Aguilar 

Because it’s something that I haven’t read anywhere.

Greg McKeown     

It’s unique?

Elena Aguilar 

Yes. Yeah, I haven’t read anything like it. It combines. I love books that combine ideas and combine genres and try. And that’s what it does.

Greg McKeown     

Often in life, when we’re not quite getting the results we want. We think the answer is to push harder on the current strategy, rather than find a new strategy, find a better strategy. I mean, in this case, it might not be an easiest strategy. Exactly. Because you’ve just described, the one you’re on is, is so much easier, because it’s just, it sort of came to you it found you. And you’ve just been able to, to go with it. But I wonder whether the way to the 10x level isn’t just 10 more of what you’re doing. It’s one of something else,

Elena Aguilar 

Yeah, that makes a lot of sense. Then how do you figure out what that something else is?

Greg McKeown     

I mean, I could be wrong, but it feels like you, it feels to me, like you may already know. But because it’s unfamiliar. It’s taking courage to take that journey, to take that step. And courage, as we all either know, or ought to know, is not a nice feeling. We want to be in need of courage and to feel courage as rarely as possible. Because it really just takes all of that vulnerability. Yeah, it takes all of what we have to step one inch into that vulnerability. It’s not really that the way itself is harder. It’s not the work itself. That’s harder. It’s the fear. The sense of I am such a what’s the word I’m looking for? I am such I’m faking this. I am a I am such a fake. It’s such a phony. I’m gonna be found out, if I take this path.

Elena Aguilar 

Yeah.  

Greg McKeown     

What are you even doing thinking about this? You’re not credible in this. You’re going to stick with your stick with your knitting, you’ve got to stay within your core competency of the past. And I’m not even here telling you what to do. I’m really trying to hear you. And I think what I hear is there is it’s not really the easy versus the hard path. It’s the safe path versus the right path.

Elena Aguilar 

Yes, you’re absolutely right. Courage is not a nice feeling. That feels liberating somehow, because we’re you know, encourages is such a lauded trait.

Greg McKeown     

isn’t it? it’s always good in in the hero and the heroine. It’s always good that they have it. But when you have it, it’s full of trembling.

Elena Aguilar 

Yeah. Yeah. Yeah. There’s no way to feel courageous without feeling terror at the same time.

Greg McKeown     

No, there’s no point whatsoever for courage. Unless we’re trembling.

Elena Aguilar 

So I’m just having a big like fear attack. That’s what that’s what I’m coming at. It’s like, right, I know what I want to write. I know what I want to do and not do. But I’m just really scared that I’ll make the wrong decision. The anxiety is always am I making the right decision? And am I making a decision that, you know, will this bring stability for my family? Will this decision have a positive impact on society? Will I regret it when I’m older?

Greg McKeown     

What are your answers to those questions given where we are in this conversation?

Elena Aguilar 

Well, I’ve made a lot of good decisions in my life. And I think I can take more risk than I’ve taken. I mean I can take a measured risk, and I really like the analogy of the tent poles. And what that evokes for me, which is, rather than writing five more books, that might be do sort of, as well as the ones I’ve written, maybe I can write one that is deeply meaningful and satisfying. And that has a greater deeper impact and creates different opportunities for me.

Greg McKeown     

It’s interesting that out of all the things we’re talking about, that’s the thing that you’re coming back to, that tells me something’s going on inside of you. That’s not just my opinion for you or something. That’s the part you’re being attracted to. What I think is happening in you is that there’s something nudging you towards a different strategy. And that this is good news because It’s your own mind and heart, telling you and teaching you how to go from where you are to where you want to be. You can’t go from here to there by doing what you’ve done in the past, what got you here won’t get you there.   And that doesn’t mean you have to go cold turkey. I’ve generally over stated that in my own life, that it’s entirely all or nothing. It could be that there is Patrick McGinnis was the author of FOMO. And the person who came up with the term FOMO. And I also had him on the podcast, he teaches the principle of the 10% entrepreneur. And that is, if you’re going to try and take a risk in a new area, maybe take 10% of your time and devoted entirely to that new thing. So that you’re not immediately feeling the panic of, well, I quit my job. And now I’ve got to make this happen. And there is a more sensible journey to the new. But do spend the 10%. So that you can start seeing these pieces come together, this new, your thoughts?

Elena Aguilar     

That feels really doable, that feels really clear, and actionable. And I also just, I really appreciate you said, to achieve what I want, I need a different strategy. That feels really, that feels really freeing. Because it doesn’t feel like I’m chasing my tail in a circle.

Greg McKeown     

So let me ask you this, what is the very first physical action that you can take to pursue this new direction?

Elena Aguilar     

I think I need to look at my calendar and block out the time I need to write, and ask someone, one of my teammates to sort of be my accountability partner or to help me hold that time. Like no matter what comes up, I can’t schedule anything on that day.

Greg McKeown  

It sounds like it’s something like one day a week. Maybe it’s even half a day if we’re thinking 10%

Elena Aguilar 

Mmhmm.

Greg McKeown     

So the very first step is opening your calendar.

Elena Aguilar 

Yes.

Greg McKeown     

That’s doable. You just open your calendar. You need to just put something new on there. What day are you going to do it?

Elena Aguilar     

I’ll probably have to work with the calendar, my calendars, about six months out has all kinds of things on it. So I’ll probably may not be the same day each week. I think what’s key for me is going to be asking my teammate to help me hold that time.

Greg McKeown     

So maybe the first step is calling or texting your teammate to say, I need to have a conversation with you.

Elena Aguilar     

I need to write this book, and I’m going to block out time on my calendar, and no matter what comes up, I mean, maybe if President Obama wants to talk, I’ll break that. But, uh, nothing, nothing can nothing can take go in that time. You know, because that’s the thing. Sometimes things come up and say like, Oh, this is a great opportunity, or this group has been trying to get you to work with them for three years. And you have that one afternoon. Could you do it then? And I just need to, I need to make it clear to everybody that I’m not, I can’t I’m not available.

Greg McKeown     

And can you just put into words why this matters so much? So that when you text you don’t just say the what, you can explain the why.

Elena Aguilar     

Yeah, I think I think I have to work on that. Because I think it’s, I have to figure out those words, because I want to say, because I have to write this book. I

Greg McKeown     

Why, why do you have to?

Elena Aguilar     

Why, because it sounds so dramatic to say, but I feel like if I don’t, I just like I’m gonna die. Like it’s a story that I have to tell. And that it just, I can’t. It’s, it’s already finding ways to come out. I think it’s just I’m anticipating that people said, Well, why are you writing that? Why don’t you write more of what we know you’re going to get a good response to. And so why take such a detour? This is you could write another book about this or that? And it would, we would do? Well, we know that. But I don’t want to.

Greg McKeown     

So, your why is I’m gonna die if I don’t write this?

Elena Aguilar     

Yeah.

Greg McKeown     

This has to come out of me.

Elena Aguilar     

Yeah.

Greg McKeown     

Or I’m going to get sick. And I’m not going to work anymore. I’m not going to function anymore. This must be done. One of my favorite quotes about writing is that writers write because they can’t not write. And that’s what I’m suddenly sensing in between the lines here is that tell me if I’m wrong. I think you got caught in a parallel path that you said, I want to write. I am writing. But I’ve got to run this business. And this business now needs me to keep writing these kinds of books. Yeah. So now, I am semi slave to the business strategy. But I can now in light of this conversation, assert that I am an author who happens to be an entrepreneur, not an entrepreneur who happens to be an author. So my strategy needs to be about writing the right thing. And then let’s build a business around that. build a career around that bill, whatever I need to do around that, but not the other way around. Mm hmm.

Elena Aguilar   

Yeah, I love that, that I’m caught in a parallel path. And I have sort of created this business that now I feed rather than it is feeding me in a sense, it feels like this, this little monster that I have to keep going. Which is okay, I can figure out a way to make it. Make it work better.

Greg McKeown     

Let me just make the observation. I think writing is primary in so many fields. And it’s actually taken me a while to understand that, strangely enough, even though, really what I do is teach and write, you know, that’s all I’ve done for many years. I still am amazed at how many things grow out of the writing part of my work. And you think about many other fields, too. Whatever it looks like on the surface, when you actually get down to where the value creation is happening. It’s some form of writing. The value creation isn’t just in the conversations in the brainstorming, it’s not just in that it’s the writing, it’s where you sit down. focused, concentrated writing is, I think, the beginning of most of the value flow.  That takes place, even in industries that it’s not obvious at first. So I think that that’s the key distinction going forward is that the writing is the priority. It’s gotta be intent driven. What do I need to bring forth into the world? What is within me that needs to get out of me? And let’s see where that journey takes you.

Elena Aguilar     

This is really helpful, so much I want to process and digest but mostly I feel a lot of relief and clarity, and, and affirmation in terms of, you know, I may be experiencing a lot of fear and everything else that’s going on. But I also am really clear what I need to do. And I need to figure out the next steps to do it.

Greg McKeown 

Elena, it’s been my real pleasure to talk with you to, to listen to your current grappling, wrestles to discern between the good and the great, the good and the right. And it’s an honor to be able to sense this early, but vitally important creation, that’s happening. You said it’s like, like, birthing. And I think it is, it’s an act of creation, to bring something forth. I think it always does take courage because it starts so small, and it starts so different. And we’ve got to try and nurture it and bring it to life. It’s already a little bit of life at the beginning, but we have to try and protect it and develop it and build it. And, and in that great things can happen. And I think my sense is that it’s not at the first phase within you that it’s made maybe the third or fourth or fifth phase. It’s just still feel small and young. But actually, it’s been growing for a long time, and it’s just bursting to come forward. But it’s not in alignment with the current strategy around you. So, it’s, it’s harder to imagine how it would, how to even bring it about and I hope today’s conversation has been helpful. And I really thank you for your time and your vulnerability in sharing your story with us. Thank you, Elena.

Elena Aguilar      Thank you so much, Greg. This was really helpful.