Time to talk about the other F-word.
Today’s letter-writer is filling about five different roles at his company—and feels like he’s failing at all of them. Add in gaslighting executives and the finite number of hours in a workday, and he’s about ready to shut down entirely. Should he just take off all these extra hats and quiet-quit? Should he just care less about work? Listen in as Jen and Sara help him decide which balls to drop and how to redefine success, and failure, on his own terms.
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Jen Dionisio 0:00 If you like Per My Last Email, we want to make sure you know about our newsletter Nice Work. We've just moved it to a new platform, and we've got plans to publish a whole bunch of essays over the next few months. So if you're not getting Nice Work yet, head to https://newsletter.activevoicehq.com/ to see all the past editions and subscribe.
Sara Wachter-Boettcher 0:18 What's up, everyone? This is Per My Last Email—the show about what to do when work gets weird. I am Sara Wachter-Boettcher.
JD 0:43 I'm Jen Dionisio.
SWB 0:45 So what are we talking about today?
JD 0:47 Well, today, we're going to look at one of the F words: failing.
SWB 0:52 Oh, I know that one.
JD 0:53 Uh-huh. So specifically, we're going to talk about what happens when you've got so much on your plate that you feel like there's absolutely no way you can be successful.
SWB 1:03 Yeah, this has been coming up with a lot of my clients lately. It's all of that, like post-layoff gaslighting.
JD 1:08 Yeah.
SWB 1:08 "It's time to do more with less. We need everyone to deliver faster. You need to be spread across more product areas." All of these different messages people are getting that really come back to somehow you just need to do more than is humanly possible, and if you don't, you're failing.
JD 1:23 More responsibility, same pay. Aren't you happy about that?
SWB 1:30 And yeah, you're supposed to be pleased because you still have a job.
JD 1:32 Ugh.
SWB 1:32 Yeah, and you know, there's another one that's coming up a lot, too. In fact, I just talked to somebody yesterday who's going through this, where they're basically told, you know, "Hey, we laid off this team's manager. So congratulations. They report to you now, too.
JD 1:42 Oh, brutal.
SWB 1:43 And you know, it's so common. I even saw that there was some new research about it. We'll put it in the show notes. But what I was reading was an article in Axios where they were talking about how the average number of direct reports a manager has has doubled in the last few years.
JD 1:57 Wow.
SWB 1:58 And I'm not sure that's happening across the board. I think a lot of that is more focused in like, small to mid-size businesses. But still, I've seen this trend a lot anecdotally, and it's, like, very clear that people are getting stretched in serious ways. So yeah, in that context, no wonder we have folks who are writing in feeling like they're failing.
JD 2:17 And if everyone feels like they're failing, is anyone failing, huh?
SWB 2:21 Yes, perhaps we have to reset our expectations.
JD 2:24 Oh. So, speaking of that, let's get to our letter-writer.
JD 2:33 So Sara, this person describes themselves as a player/coach, already two roles in one, and they are dealing with that same kind of overwhelm we were just talking about.
CL 2:45 I am in a 50/50 global manager/individual contributor role. I'm also the domain mentor for my team so aside from recruiting and hiring, I also onboard and upskill them. I'm expected to increase retention and engagement on my team, and improve team culture. Problem is: there is quite a bit of corporate (and senior leadership) gaslighting going on. Wearing soooo many hats and faced with a "head-wind" culture, how do I come to terms with failing? Should I give up on trying to personally succeed and thrive? Or - as my partner suggests - should I simply care less?
SWB 3:24 Oof Jen, this one hit me hard. This guy sounds like he has too many jobs.
JD 3:28 Yeah.
SWB 3:29 Like craft leadership, people management, and IC work. And you know, I know he's not alone in that. I know a lot of people are wearing all of those hats, but I also know that it can be pretty exhausting to switch gears so often and to feel like nothing you're working on can get any real attention.
JD 3:45 Yeah. I mean, it's no wonder they're wondering if they should care less, because I can't imagine caring a lot about all of that. Let's actually call them that: CL or "Care Less." And let's start with the more extreme question that they posed: what is your reaction to this idea that maybe he should give up on trying to personally succeed and thrive?
SWB 4:09 Yeah. Well, I think before answering that, I would suggest that we unpack the concepts of succeeding and thriving. So my first question for CL is this: succeed and thrive according to whom? What is the definition of success you're using? And where did that definition come from? And same with thriving. What does it mean to thrive, and who decided that? And Jen, I say this because in my experience, and maybe in yours too, when I'm coaching people, I find that a lot of people really haven't defined those things for themselves. They're just kind of reflexively defaulting to whatever they've absorbed from their company or from, like, general senses about what society expects.
And CL, you might care about what your company thinks, and you might care about what the world thinks about you, but I will say I think that in this moment, that's not sufficient, and I think you also need your own definition. So let's start there. And to do that, here's what I would encourage you to think about: CL, what is actually important to you here? And I'd go back to your values to really think that through. Like, what kind of person do you want to be? Let's imagine it's five years, 10 years, 20 years from now, and you're looking back at the decisions and the behaviors that you have today. Which ones would you be proud of? What would you be less proud of?
And in addition to thinking about your values, I'd also encourage you to think a little bit about your interests right now. And I know it can be an impossible time to feel like your interests matter when you're getting all this pressure from your company, but I think that this is actually really important for keeping a sense of self and keeping, like, something for you here in a time when it could be so easy to kind of lose track of who you are and what you care about. So think about like, what kind of work makes you tick? Where do you find yourself curious to learn more? What kinds of growth feel exciting right now?
Again, that's not to say that what your company wants isn't a factor. Like, they sign your paychecks. I understand. You gotta think about their expectations. You gotta think about business priorities. But to me, what it sounds like is that what your company wants from you is everything. And you also said that there's a lot of gaslighting going on, and so if your definition of success is purely driven by them, like, "I am succeeding when my company tells me I'm doing awesome," well, I'm not sure that kind of external validation is achievable right now. It doesn't sound like your company's gonna offer you that. Or if it even is achievable, it may not be achievable in any way that's sustainable, like in a way that accounts for your wellbeing, that avoids you burning out.
And so if meeting their definition of success will stop you personally from thriving, is that worth it? Obviously you can guess that I'm thinking that might not be worth it, and I would encourage you to really think about that, CL. And the other thing I would really suggest is, instead of focusing on getting as much of that external validation, like having your company tell you you're doing great, I think it might be helpful to think about, "How can I give myself more internal validation here?"
When you define what you really care about, like when you sit down and you go, "What is actually meaningful or important to me?" that gives you something you can validate yourself about, because you can focus on achieving that and actually feel good about that work, even if you're not acing everything that they've shoved into your already crowded plate.
JD 7:25 Yeah. Okay, so, Sara, this actually brings me to another question about failure, because I had a really strong reaction to CL asking how to come to terms with failing, because I just don't feel like this is a simple win/lose situation.
SWB 7:41 Yeah, yeah. I definitely flagged that word too. And you know, CL, I don't know you, but I've worked with a lot of people who've used similar language, and what I've found is that oftentimes they are stuck in what I see as a perfectionist mindset, where they see anything other than being perfect as a failure. So if that resonates at all, I would really encourage you to think a little bit about perfectionism here. Perfectionism is something that a lot of us learned as a coping pattern in childhood.
JD 8:09 Not me.
SWB 8:12 Maybe because we grew up being criticized a lot and we fear rejection. But those tendencies actually can also develop as adults in the workplace, often as a response to fear, as in, if you're afraid that you're gonna lose your job in another layoff round, which, let's be honest, that's a valid fear for a lot of people, that can bring out perfectionism as well. Because what our brains are doing is they are trying to have a sense of control. They're basically telling us, like, "Okay, if I just control every detail, if I never miss a beat, if I can be perfect all the time, then that's gonna keep me safe. That's gonna control the outcomes."
And you know, CL, that can work kinda for a while, meaning being really excellent at what you do, and keeping lots of balls in the air, and wearing all the hats, it might help you avoid a layoff. But honestly, it might not, because a lot of layoff decisions are being made based on totally different criteria. Sometimes it's like, well, the business is going in this other direction, and it's going to focus its bets somewhere else. And so doesn't matter how perfect you are if you happen to work in a part of the organization that's getting deprioritized. Or the other thing I've seen is organizations making layoff decisions truly haphazardly, just like based off of vibes and whims. And again, trying to be excellent at everything?
That's not gonna help you in that circumstance either, because the layoffs aren't really about you, and I think that's such an important piece to always remember: A lot of organizational decisions? They're not about you at all, and trying to like, control and be perfect to prevent anything bad from happening is a super high energy endeavor. It takes so much from us. Like, the cost is really high. And there's a pretty good chance it's not gonna make a difference. So if perfectionism is something that resonates with you, I'd really think about, how is that showing up right now in your feeling that you can't let go of anything?
What is it costing you? Like, what's it doing to your brain and your body to feel like anything less than excellence is failing? In my experience, when that bar is set so high, especially in an organization that sounds under-resourced and, frankly, kind of chaotic, it's a recipe for burnout, because there's just no way that you can constantly context shift and keep up with all the details of your team members, of your own work, keep up with the craft without something slipping. And I think feeling perpetually like a failure is very, very hard on people's psyches and very, very draining, and I don't want that for you.
JD 10:34 Yeah, Sara, as you were describing that, I have to admit, my mind kind of wandered to when I very much felt like the way you were describing of that perfectionism just forcing me to keep all those balls in the air, and not surprised that that led you to start talking about burnout, because that was exactly where that took me when all of those balls just came crashing down.
SWB 10:55 Yeah. So CL, this is why I started out by suggesting that you really think about what you care about, and that you start determining your own definition of success. Because when you know what that is, you can give yourself permission to focus. You can give yourself permission to say, "Okay, well, my company thinks I'm gonna wear 38 different hats. That is too many. So which hats really matter based on my values, my interests, and what I think is most important to the organization right now?"
And then for the rest of those hats, "What would happen if I dropped a few and I just stopped investing energy in them entirely?" Which, CL, I want to be clear that is not the same as failing. That's a strategic choice. That's choosing where it matters that you actually do a good job and where you're willing to make a trade-off to make that possible. So, CL, what might you just drop? And also, where do you need to accept that maybe you're gonna do like, a B- job, or, hell, a C- job? What are some things that can just be good enough so that you still have energy to make a few things excellent?
JD 11:56 C's are still average.
SWB 11:57 Yeah, that's what they say. So CL, I want you to know that if you do this, if you start thinking about dropping some things, if you start thinking about sometimes doing a C- job, that might bring up a lot of thoughts and feelings for you. You might worry that you're lazy, or you're incompetent, or you're just not ambitious enough, or maybe you're gonna worry about letting people down or letting the organization down. Whatever those thoughts are for you, and I suspect you'll have a few of your own, I just want you to know those are normal. Those are very normal thoughts to have, and they come from the parts of us that are scared, like, the parts of us that are afraid that being imperfect makes us unworthy or unlovable or will get us rejected forever.
So these are thoughts that are coming from parts of us that really just want to be safe and that believe that if we can just control everything, then we'll be safe. It's okay to have those thoughts, but that doesn't mean those thoughts need to be in the driver's seat and calling the shots. So whatever your particular worries are, I will just encourage you to allow yourself some space to allow the thoughts to exist, but kind of think of them as like they are thoughts that are floating by. You don't have to fully believe any of them, and you don't have to act on any of them. They are simply thoughts that are floating in the wind, and you can observe them and remember that that's just one way of seeing things, and it's a way that is laser focused on trying to keep you safe, even if that safety comes at the expense of your wellbeing or your health or your sense of self-worth.
And so I'd also love for you to try on a reframe here, CL. What if letting go of some things doesn't mean you're being less ambitious, what if it means you're being more ambitious because now you're being super selective about what you're ambitious towards?
JD 13:43 I love that. I actually wish I had given that recommendation to some of the people I used to manage, too. I truly think it would have helped them find that focus. Okay, I digress. Let's imagine CL has kind of redefined success for themselves and redefined failure for themselves. What should he do after that? I know that their partner suggested that CL just care less, which can feel really impossible to practice.
SWB 14:13 Yeah.
JD 14:14 Are there some tools or techniques that CL might put into place to kind of maintain that sweet spot between apathy and over-investment?
SWB 14:22 Yeah. I mean, I can really see where CL's partner is coming from. Caring less seems like it might be a way for CL to stop worrying so much and to stop feeling like they have to be perfect at wearing all these hats and spinning all the plates. But you said apathy there. I think that's a really important thing to think about. When people get apathetic at work, it doesn't make them happy or fulfilled in their lives. It doesn't give them a lot of joy. We spend a lot of time at work, and so going too far in that direction of apathy, even though it can prevent us from being over-invested, it can also leave us feeling really drained and numb and lonely and cynical.
And it really turns every day into a slog, because if you don't care about anything, you can't enjoy anything, there are no wins. All you can do is survive it. And look CL, that might be okay if you're planning to be there for only a very short term time. Like, if you're simply trying to survive a toxic environment for a few more months while you job search? Okay, that can work. But when you take it on as a life strategy, like, "My entire relationship to my work now is not caring," yeah, it's not great. I believe strongly after seeing a lot of people go down this path that it's just as big of a driver for burnout as over-investment.
JD 15:33 Yeah.
SWB 15:33 Because no investment makes your days feel pointless. There are no wins, there are no bright spots. And you know, it also tends to really alienate us from other people. Because we're shut down and we can't connect with them. And also, if we show up cynical, guess what? We make the vibes rancid around us, and people don't want to hang out with that.
JD 15:55 Yeah.
SWB 15:55 So I really can't recommend living in that way, where you just stop caring about work entirely. So Jen, you asked me, how does CL find the sweet spot between that kind of apathy and over-investment? What I want to suggest here is that it may be more helpful CL to almost let go of the idea of balance or moderation, not because you don't want to get to a place of some balance or moderation, but because that can be really hard to figure out how much is enough? How much is too much? And I think particularly when we've reached a place where we're already fed up and we're feeling frustrated and we've over-invested for so long, we kind of ping-pong. We treat it a little bit more like an on/off switch. It's all or nothing. We go from caring way too much to just saying, like, "Screw this. I don't care at all."
And so when that happens, then you definitely hit that apathy zone. And so instead of trying to figure out how to, like, modulate caring, I think an easier way into this that I would suggest trying out is framing it in the same way that we looked at success and failure: getting specific about where you care. So making it less about how much you care about your work, and instead looking at it as can I get selective about which things to care about? So going back to those values and those priorities, and then saying, "Okay, well, if this is what truly matters, what's worth me caring about? If my time is precious, if my attention is precious," and CL, I want to encourage you to believe that it is, "what is truly worth my care?"
JD 17:23 This was really helpful for me a while back when I was sort of wearing a lot of hats.
SWB 17:29 I hope they were cute.
JD 17:30 I kind of looked like Blossom. Did my little curtsy at the end, but it wasn't—
SWB 17:38 Our younger listeners might struggle with that reference.
JD 17:41 I know.
SWB 17:42 Look it up, everyone. Great hats.
JD 17:44 That was for all my elder millennials. But I felt like CL, just like failing all of the time, and where both my values were, you know, they're very relationship-oriented, and also even some of my interests, like that was when I was really starting to think about coaching as a path to follow. And so I realized that what I cared most about was the management piece of my role, not the craft, not the sales, not the you know, IC work, but the people that I was kind of in charge of supporting and helping to grow. And it was like, I know I can be a great manager or a great IC, but not both.
And when I started making the conscious choice to just lean into being the best manager I could be and being a "good enough" at everything else, I was so much less stressed, and I found so much more kind of like pleasure in the work I was doing, and I wasn't so bogged down in all of the like anxiety of all the other roles that I had. And kind of, like you said, it didn't mean I was suddenly bad at those or, like getting in trouble for not keeping up. It's just I didn't let those be, the thoughts that, like, stuck with me at the end of the day. It was like, "I'm gonna show up. I'm gonna do what I can, and trust that that's good enough, or else I wouldn't be here anyway."
SWB 19:12 It really strikes me that by doing that, it gave you things to point to that you felt really good about, instead of feeling kind of like meh about all the work you were doing. And so then when you're just doing so-so on some stuff, it doesn't feel like that's everything, because you have these other things to point to that you are genuinely feeling good about.
JD 19:32 Yeah.
SWB 19:32 You know, something else this brings up for me, though, that I think might be helpful to frame up for CL, is, like, it doesn't mean there's no value in being a great IC, right? Like it doesn't mean that just because you made that choice, that the other things don't matter. I think what it's more about is saying, "I am one human being. I have finite time and finite energy, and so I want to focus that in a way that allows me to actually get somewhere. And I'm willing to accept that I'm gonna have to lose or trade something off in the process." That means CL, that if you go down this path of making some tough choices about what's really important to you, whether you make similar ones to Jen or different ones, you might have some feelings about it.
Like, let's say that like Jen, you decided you really wanted to focus on being a great manager, and decided, like, being a so-so IC was okay with you. That might bring up some grief, like a sense of loss of craft skills, or a sense of loss of identity as like being the person who's the best at this particular area of work. And it's okay if you have those feelings. I know personally, when I decided to stop consulting on product work and really focus purely on the people working in design and tech, it felt weird.
JD 20:41 I bet.
SWB 20:41 And it felt a little scary.
JD 20:43 Yeah.
SWB 20:43 I mean, I was letting go of something that I had really cared about in the past and that I was good at, and that like people knew I was good at. And I was trading it for something that was newer to me and that I was objectively less of an expert in, but I wasn't going to become an expert in it if I didn't give it focus. And what I had to accept was in order for me to do this work, well, I needed to let that work go, not because I didn't like it, but because it was no longer the right fit for me, and because my attention was too split, and it meant that everything was suffering.
And so there was a little bit of a process of grief and acceptance I had to go through to be able to say, "Yeah, that other work is interesting and meaningful and it mattered to me, and I could keep investing in it, and I'm choosing not to, because the work that is calling me more strongly right now, the work that I feel like I can't not do, it deserves the best of me, not the me who's exhausted from context shifting and who's only half-attentive to the details."
JD 21:41 And also, I think, make space for other people who do want to focus on those things to also be able to really kind of focus their time. It has ripple effects.
SWB 21:50 Yeah, I think that there's this piece that's about, like, allowing yourself to evolve and trusting that not everything needs to be yours for it to be important, and that other people will pick different important things to them.
JD 22:03 Yeah. Okay, so Sara, we have talked about CL making some tough calls and accepting that they can be successful if they redefine success a little bit more narrowly, but I am imagining that if CL is like me and probably you at times, they might still be nervous that if they do this, they'll get in trouble anyway. Like, they'll get a bad review, or people might get mad at them, or people might stop thinking about them as being special or important. So how might CL navigate perceptions of them in their org? You know, especially in a place with a lot of gaslighting, as they described?
SWB 22:42 Yeah, this is a critical piece, and part of it is that CL, not all of this is in your control. Like, your organization, it sounds like, has people in it who are going to say and think things that are unfair irrespective of what you do. So what I would encourage you to do, CL, is to really think about where not choosing, where not being selective, leaves you and your reputation. Because in your letter, it sounds like you know you can't be successful keeping up with everything that they've tried to jam onto your plate.
So if you already know that you will "fail" if you keep trying to do what you're doing, then maybe the risk of doing something different isn't that high, because it sounds like doing what you're doing isn't actually that safe. It sounds like a pretty good chance that even if you keep juggling everything, you're still gonna be told you're not doing a good enough job. And so I'm like, well, if you're gonna get that feedback regardless of what you do, what if you at least made the job into something that is more sustainable and enjoyable for you? Also, what if you don't get a negative response?
JD 23:41 Ooh.
SWB 23:41 You might. But something I often find is that people are so convinced that if they drop anything, everyone's gonna be mad at them, and then they make these really extreme statements, right? Like, "If I drop anything, everyone will be mad." Like, really? And so that can turn into this big spiral where it's like, "Okay, well, I dropped one ball. Well, my cross functional partners are going to hate me, and they're going to escalate my manager, and then my manager is going to put me on a PIP, and then I'm going to get fired, and then I'm never going to find another job, and then my life is going to be over.
JD 24:21 That sounds like my brain.
SWB 24:12 Slow it down. And so, like, we start telling ourselves these really extreme stories about what's going to happen if we make a change without pausing and asking, like, "Wait, how do I know that's true? Where's that coming from? What evidence is there that all of this is gonna happen?" Also, like, what else might happen? Okay, that's like, all of the most extreme worst cases. But what if some other things happened? What are some other possible outcomes here? And you know, the other thing that I know, CL, is that sometimes people do get criticized when they set priorities and drop things, but it's really common that they don't. Sometimes I find that what people get is actually praised.
And it's counterintuitive when you're in a moment where your organization is saying, like, "Do more, do more, do more." But what I've also seen happen is that even in that context, when somebody drops something that wasn't that important, they suddenly do better work in the areas where they've chosen to focus. They're more creative, they're more engaged. They speak up in meetings and bring a point of view because they're not just trying to like keep up, but they actually have something to contribute. They're better able to like move things forward and get things unblocked, because they have the energy to unblock them, as opposed to just like letting things churn and churn and churn, which is what happens when we're drained from being spread too thin.
JD 24:38 Yeah. You know, and Sara, I think that's such an important thing to remind managers to think of, because I do think a lot of folks, as they kind of move up in seniority, have accumulated all of these sort of like expectations of what they're supposed to do and never shed any parts of them as they—
SWB 25:43 Oh, yeah.
JD 25:44 have different roles.
SWB 25:45 Only additive.
JD 25:46 Yeah.
SWB 25:47 So CL, I mean, look, I don't work in your company, and so I don't know what response you'll get there. And I don't want to tell you like it'll be fine, because I don't actually know that. But what I do know is that it's important to find out. And so what I would encourage you to do is think about this as an experiment. When you identify the stuff you really care about and want to stay invested in, then you can start identifying some smaller stuff that you could maybe test out as places where you disinvest and where you deprioritize and see what happens. Does anyone notice? Does anyone get mad? How does doing that change the energy that you have for the rest of your work? How does it change the way you feel about your days? How does it change the way you feel about success and failure?
And as you experiment with letting some things go, you can start to, like, make some of those things a little bigger as you go. Doesn't have to be all at once, but you can try out little things and then see, "What if I let this other thing go?" And then keep checking in on that feedback. What happens? What feedback do you get? And finally, CL, I would really suggest thinking about this: Sometimes we assume everything is going to crumble if we stop holding it together. But there's something else that can happen, which is when we stop holding it together, somebody else shows up to hold it together, because they realize that it is important and it's not being attended to.
And in an organization that has under-invested or under-resourced, it can lead an organization to step up and say, "Oh, there's a problem here. Things aren't getting done." And if you never let anything drop, they don't notice or care, because for them, there isn't a problem. It's only a problem for you. You're the one who ends up breaking. And so, CL, you don't deserve to break just so this organization can keep under-investing. Maybe it's time to give them a chance to step up and solve some of the issues that are really organizational problems, not just CL problems.
JD 27:37 I suspect if CL is feeling this way, there are probably lots of people around them that are feeling the same. To close this, CL, I just think your wellbeing is always something that you're going to want to care more about and not less about. If you can make that an important part of your measurement of what failure or success means, I think it's going to be an incredibly worthwhile goal for you that's going to pay off throughout the rest of your career and hopefully your life, too.
SWB 28:08 Who cares what your title is if you're miserable?
JD 28:12 And that's it for this week's episode. Per My Last Email is a production of Active Voice. Check us out at https://www.activevoicehq.com/ and get all the past episodes, show notes, and full transcripts for Per My Last Email at https://www.pmleshow.com/. This episode was produced by Emily Duncan. Our theme music is "(I'm) a Modern Woman" by Maria T. You can buy her album at https://thisismariat.bandcamp.com/. Thank you to Care Less for caring enough to submit their story to today's show, and thank you for listening.If you've got a dilemma eating away at you, please send it over to us. Head to https://www.pmleshow.com/ to submit your story.