Greg McKeown:
Welcome. I’m your host, Greg McKeown, and I am here with you on this journey to become 1% wiser every day. What would your business or your life look like if you designed it from scratch using essentialist and effortless principles to guide you?
It’s long been thought that some industries like private equity, medicine, and law just take 80-hour weeks to be successful, but this is false. What we know now is that the way these industries are designed to produce this kind of burnout culture.
Today is part two of my conversation with Kyle Westaway, who has designed a law firm from scratch using these principles. By the end of this episode, you will be able to say no with greater competence and confidence so that you can design a life and business where it’s more effortless to achieve what matters most. Let’s begin.
If you want to learn faster, understand more deeply and increase your influence, teach the ideas from this episode to someone else within the next 24 to 48 hours.
I was just thinking today that you can’t fix the burnout culture with a wellness app. No, that’s not going to do it. The burnout culture is created by other things like an iceberg, all the stuff under the surface that you can’t really see, and if you just try to treat the presenting symptom on the surface, then you’re going to still have the condition again and again until we can diagnose it more correctly. You are saying that at the heart of why things tend towards burnout within the legal profession, but perhaps beyond, is that there’s an incentive to ask for burnout from people rather than an incentive to get people to produce sustainable quality results.
Kyle Westaway:
Yep. You said it. I totally agree with that. I have many friends in big law firms and big consulting firms. My wife is at a big consulting firm, and they are doing, they’ve taken a lot of steps in the last couple of years to do some amazing things. What I’ve been hearing is doing a lot of work and recognizing mental health issues that come with that sort of work culture, offering so many services, like an abundance of supports and services around this structure. But to your point, the incentive, the core incentive of how the thing operates, it drives towards, I think, mental unwell being right, and so having these little, these little palliative opportunities, which is certainly very appreciated, but it’s not enough. It’s not enough because the whole system is designed to really overextend and overutilize some really bright people.
Greg McKeown:
The system is perfectly aligned to produce burnout. We’re not getting symptoms of burnout from people consistently, increasingly, and across the board because we didn’t offer yoga at our company.
Kyle Westaway:
Right.
Greg McKeown:
Even if that’s a good idea, right? If you could take a metaphor now, a traditional law firm, and you could now announce we’re going to offer yoga classes, you’d be straightening deck chairs on the Titanic. That’s not the problem. Even if it’s a good idea to do it, it doesn’t address the undercurrent. So help me to make this even more actionable. Somebody listening to this right now who’s suddenly waking up to this idea of, my goodness, I am in a system that incentivizes something other than quality results. What can they do? Let’s say they’re working for an existing company. What can they do to change this? Or are they just victims of the system, and they need to get out and create their own business as you have?
Kyle Westaway:
That’s a possible answer. I always think that there’s room for entrepreneurship within companies. I find that the best entrepreneurs in big organizations, first of all, are already seen as really competent in their organizations. So they already have internal credibility, right? They’re good at their job. They’re not trying to quote innovate because they’re a bad employee, they’re not delivering, but they’re high producers. So if you have that credibility within your organization, you have some sphere of influence. And the question is, what do you do with that sphere of influence?
I wonder, an open question that I have is, if I were in their shoes, is there a way that I could try a very small bet, maybe a tiny client project or a tiny objective, and organize it in a way that aligns incentives for results as opposed to, let’s say, hours in as a point of contrast?
And I wonder if I was in that position and I chose the right project correctly and was able to excel and show that there’s decent profit margins for the company there, if I might have the credibility to try it again on a slightly bigger scale next time, and then try it again on a slightly bigger scale next time. And then, if the answer is yes to all of those 40 times over, maybe you’re able to say, “Hey, I’m going to run my practice group in a different way. I’m going to be delivering higher profit margins to the firm, but I’m just going to do it in a different way.” I think that’s where internal change can happen. And then you start to have a system that’s working in your favor.
Many of these, we’ll say client services as an example, many of these firms have a high degree of internal competition within them. So one partner wants to outperform the other partner for bragging rights, et cetera. So if you can be the leader within that organization that’s proving really quality results at high-profit margins in a different way, then you, the competition internally, starts to kick in. Maybe we should try what Susan is doing because she seems to be doing it great, and her team is not in the office nights and weekends, and they’re delivering results. So that would be my guess. And I’ve never been in that position, Greg, so I don’t know how actionable that advice is, but that would be my guess.
Greg McKeown:
It seems to me that there are specific phrases people can use to be able to increase the probability that they can affect this in whatever situation they’re in. And if I might suggest that people listening to this just pause and ask. For example, somebody asks you to do X, right? Your internal customer, you pause, and you ask, what does success really look like for you? So instead of being an order taker, they’ve asked for it, let’s go. They’ve got the email, we’re already reacting, we’re already doing, we are jumping in unaware of what is really valuable here. If you think that just responding quickly to the email that produces value, then you’ve already determined what the incentive structure is that you are limited by. What does success look like? What problem are you really trying to solve? So that if you use those questions, if you pause and ask, then you can start to understand what is really valuable rather than what the preexisting incentive structure is telling you is valuable. What’s your reaction to that?
Kyle Westaway:
My reaction is that takes a little bit of bravery, and it will feel awkward the first couple of times that you asked that question, what does success look like? And then you have to take an unexpected reaction to that email, and you have a whole chapter in Essentialism around gracefully saying no. And that might be a good resource to look at if you’re thinking about going this route. But yeah, one of my life principles is the quality of our yeses is dictated by the quantity of our no’s. So the more we can say no to the non-essential, the higher contribution we can have with our yeses.
Greg McKeown:
The quality of our yeses, say it again,
Kyle Westaway:
Is dictated by the quantity of our no’s,
Greg McKeown:
Dictated by the quantity of no’s. Speaking to that, you put a link to an article from Harvard Business Review. It’s by Melody Wilding. It’s called When and How to Say No to Extra Work. Why did you put that in the newsletter?
Kyle Westaway:
There are a few themes that I get weirdly excited about in the newsletter. One of them is actually bees. I love bees. I think they’re amazing. I think more people should know about bees. The second is sleep. I’m a huge sleep advocate, and I think it’s under-talked about the impact of having a lot of sleep. And the third is saying, no.
I think the world would be a better place if people felt more comfortable to say, no. I am by nature a people pleaser, and a big part of my maturity, personal maturity, has been not saying yes to everything. And every time I’ve been better about that, the quality of my life has increased. And why did I put that in there? Because I take every opportunity I can to help remind my incredibly high-achieving readers that it’s okay to say no. And it’s actually you. You may actually pat yourself on the back for saying no. And here are some ways to do it in ways that don’t piss people off.
Greg McKeown:
Yeah, insecure overachievers. Let’s give it that name. Yeah, they can run a marathon three weeks from now, but say, no, that’s a different kind of test.
Kyle Westaway:
They can run a marathon while putting together that deck that they’ve been working on. They can do ’em all at the same time.
Greg McKeown:
Yes. So there’s a very high competence to be able to do a lot, but as a result, there’s this underdeveloped muscle of actually eliminating. It reminds me of that advertisement. I think it’s a Skittles advertisement. It’s like in the wild, wild West. Have you seen this ad?
Kyle Westaway:
I haven’t seen it. I’m trying to picture it.
Greg McKeown:
They’re doing these arm wrestles and whoever wins gets the whatever is the Skittles or something. And so, as a result, this entire society has this massive one arm. And the other one is like puny. And so there’s this overdeveloped ability to get stuff done, and this underdeveloped ability to eliminate what should not be done at all.
Kyle Westaway:
I don’t know if you’ve read any Richard Rohr, but he talks about this idea of moving from the first half of life to the second half of life. And a big part of that journey is realizing that the skills that got us here aren’t going to be the skills that bring us to the next level. I think that is for insecure high achievers, which I’m counting myself in that group, right? I think we’ve said yes to a lot of things and gotten patted on the head for it our whole life, right? It is literally a part of our identity to be the go-to person to get something done. And so for me to walk away, to lay down that piece of my identity is, I’d rather run the marathon, right? It’s an easier thing to take something else on, then let go of that. Because if I’m not the person that says yes and gets the job done and gets the whatever, the bonus or the A plus or the compliment from our parents, whatever it is if I’m not that person, who am I?
And so I think that there’s a big element of this skill that has gotten me to this place, but it’s also now holding you back. It’s holding you back from your highest contribution. And that’s the thing that is frustrating. I’m trying to work through this on my own too, but I also see a lot of my friends that are really excelling in their career, and they’re exhausted. They’re just, the primary feeling is that of exhaustion. And we’re talking in the mid-thirties to mid-forties range, right? And my hope is that as we grow this muscle of saying no, which is counter to our identity, as we grow that muscle, we can go from a shotgun approach of being able to do a lot of stuff with a high level of competency to a laser approach of, yes, those are all good things, but what is the best thing? And I think that requires laying down the identity of being the yes person that is the go-to person that can do it all.
Greg McKeown:
That’s the thing that you are underscoring for us, is that until you change your sense of identity, then it’s hard to behave in this new way. If you can capture, for example, if somebody says, part of my new identity is to be an essentialist, how would an essentialist act, an essentialist would act in a way that is highly selective, that questions, that pauses and asks, instead of just reactively doing. In this article, Wilding goes through specific times when we should say no when your primary job responsibilities will suffer. Now, this is what you’ve been doing in creating this law firm in these conversations that you had before. Is that right?
Kyle Westaway:
Absolutely. From my experience, if it takes me too far out or if it takes me outside of my circle of competence, then I’m less available for work that is in that circle, and I have to spend a lot of time getting up to speed on something. Now, Greg, there may be points in time where I’m interested in growing my circle of competence, and that’s an awesome thing. And there have been a number of times in my career, I’m going through one of those right now, actually. But that has to be an intentional and purposeful process as opposed to just saying yes because the question was asked.
Greg McKeown:
Yes, if we’re simply doing it because somebody sent us an email, then it’s probably not a very strategic way to be making that trade-off. She goes on, she says, say no when it’s someone else’s work. That seems like also what you’ve been doing with this law firm, where you are comfortable and happily smilingly, this is somebody you might want to work with for that kind of work. That’s not what we do.
Kyle Westaway:
Absolutely. The amount of times that I say there are a lot of great law firms out there doing a lot of great work, you should go check out one of them, or, “Hey, let me introduce you to my friend who runs that firm that does that thing.” It feels great to be able to say that, and then just to be able to move forward and focus on the stuff that’s in our wheelhouse.
Greg McKeown:
Wilding then continues here. Another item say no when there’s no clear exit strategy. That sounds like these massively complex jobs that you were describing before, the international work, the complex tax structures, it’s like, this is just going to go on and on. And I don’t want to be a part of something that has no clear exit strategy.
Kyle Westaway:
I love that type of work is really exciting for some people. But for us, I actually really like a pretty tight like timeline on a project from start to finish. I want to know what the arc is going to be, and I want to ideally beat that timeline that you would usually, you know, it would usually occur in and then be done with it. I like to get the check box of done. And so, for me, a clear exit strategy is really important because I don’t want interminable engagements. You know?
Greg McKeown:
The final Wilding example here is say no when the ask is unreasonable. And I’m thinking here of someone listening who is so overwhelmed, so exhausted, so burned out, they have almost no time to think, barely to breathe, certainly no time to recuperate or to get well. That in a sense, they really are in a lot of quiet suffering that they keep saying yes, and yes, they keep taking it on. They never push back, even when it’s unreasonable. What are your thoughts or insights for someone in that situation?
Kyle Westaway:
Well, I’m highly empathetic. That’s a hard place to be. I think someone in that situation needs to have some honest conversations with the people that they’re working with and try to step back from work that is, yeah, an unreasonable request. I don’t know, like in some of these systems, that might mean I just need to work at a different firm or start my own thing. Or there might be an ability to have an honest conversation with a leader above you that’s like, “Hey, this is where I can have a contribution to the company. If you keep making these unreasonable asks of me, I’m going to be mediocre at a lot of things. And I don’t think that’s what you, I don’t think that’s what you hired me for.” But yeah, I just feel a lot of empathy for a person in that’s in that situation.
Greg McKeown:
I think it’s analogous to the situation you described at the very beginning of this process of designing a law firm from scratch using essentialist and effortless principles, that at the beginning it was enormously uncomfortable, it was really terrifying. You did not know how to do it. You did not know how to have that conversation with people. And it’s my observation as I think of people listening to this, that there will be many people listening that literally have never been taught how to have these kinds of conversations. So it’s hypothetical, oh yes, you should just have that conversation. They don’t know how to have that conversation.
I remember somebody who I worked with and coached, in fact, who was terrified of losing her job. And at first, I couldn’t work out why? Because she seemed competent and engaged. And once I really listened to them, I found out things that I didn’t understand I would never have supposed.
And I found that is really true. If you really listen to people, they will tell you unbelievable stories. She was able to explain to me that she has no parents who are alive, no siblings, no extended family, no friend network and that she’s working from paycheck to paycheck. Then add to that various forms of trauma that she had experienced in her life. And she is massively disempowered because if she loses her job tomorrow, then she’s two weeks away from being homeless. So it’s a complex question that I’m trying to get at here, but what language have you found helpful having negotiated and developed these skills that could be helpful for somebody in that kind of situation?
Kyle Westaway:
When I was building my law firm, especially the first five years of the firm, and we’re about to be in January, it’ll be 15 years, so we’re a 15-year-old firm, I would say I was that person. I found myself in this very weird tension of I would wake up every morning with a smile on my face because I couldn’t believe I was lucky enough to be doing the work I wanted to be doing with the clients I wanted to be doing it within this amazing city called New York City. And I would also wake up with a knot in my stomach that would increase in size depending on the day of the month. So as we’re getting closer to the end of the month, I needed to have money to pay my rent, like just like my apartment rent, not like my office rent, but just to keep a roof over my head. And there were many, many, many, many months where it was the 25th, the 26th, the 27th of the month, and that money wasn’t there, and it was just a really stressful way to live. The amount of weight that puts on every interaction is really intense, personal, and professional. So I would say that my situation is different, but I felt similar feelings to that.
Greg McKeown:
I think that’s a great note to end on, that really, although it doesn’t sound like it right now, although you do not seem like somebody that would be analogous to the person I put to you. Nevertheless, it’s more similar than it’s obvious, and that’s really the advertisement, so to speak here in this conversation, is that you can go from being such an extreme people pleaser with massive burdens and stresses that would disempower you to the point where you really are far more in control of your life, designing your life. And so that someone who’s listening to this, whether they’re the CEO, or whether they just want to be the CEO of their own life, can feel some inspiration, some encouragement that there are better days ahead, especially if they will discover the power that is in them, to be able to have these conversations and to design a life that really works, that really matters and is really less exhausting and stressful along the way. Kyle, thank you for being on the show.
Kyle Westaway:
Greg, it’s been a pleasure. Thank you.
Greg McKeown:
What is one idea you heard today that caught your attention? Why does that matter so much, and who is one person you can share that with within the next 24 to 48 hours? If you found value in this episode, please write a review on Apple Podcasts. The first five people to write a review of this episode will receive free access to the Essentialism Academy. For more details, go to essentialism.com/podcastpromo. Thank you. Really, thank you for listening, and I’ll see you next time.
