NOEL: Hello and welcome to Episode 65 of the Tech Done Right podcast, Table XI's podcast about building better software, careers, companies, and communities. I'm Noel Rappin.

Our guest this week is Amy Newell. Amy is the Director of Engineering at Wistia, and she gave a talk at RailsConf this year entitled Failure, Risk, and Shame: Approaching Pain and Suffering at Work. We have what I hope is an uplifting conversation about failure and pain, how to recognize it, and how to skillfully manage those feelings to be more resilient and ultimately more satisfied with your job. It's a conversation that I hope you'll find interesting and useful. And so, here is my conversation with Amy.

Amy, would you like to introduce yourself?

AMY: Sure. I am currently the Director of Engineering at Wistia. I manage the product teams there. Before Wistia, I was Director of Engineering at PatientsLikeMe which is a social network for people with life-changing diseases. I was there for eight years. I've been a Software Engineer since 1999. I also have two teenage children which is super fun. Managing engineers is much easier than managing teenagers. And I also do a lot of work around mental health, mental health in tech, and sort of managing suffering in the workplace. I have bipolar disorder and I know a lot of other people out there are also struggling with mental health issues.

NOEL: And we are here because you gave a talk at RailsConf, like a month ago as we record this? 

AMY: Yep.

NOEL: Which was called Failure, Risk and Shame: Approaching Pain and Suffering at Work. I thought we'd have, hopefully, an uplifting conversation about failure, risk, shame, pain, and suffering.

AMY: [Laughs]

NOEL: One of the things that struck me -- so we will include a link to the talk in the show notes and you should definitely listen to it. You don't have to. But we will reference it, I suppose, some. One of the things that struck me most about the talk just right off the bat was the explicitness of talking about pain and shame and suffering as things that happen at work where I think that we are often trained to sort of euphemize that. We talk generically about stress or something like that. Why is it important to you to use terms like pain and shame when you talk about work experience?

AMY: That's a really good question. I sort of hadn't considered using the word stress instead of those words. And the reason for that is that stress, as you said, it's super vague. It could mean any number of things. And what I think is most helpful about how to learn to manage pain and suffering in the workplace is that you need to really pay attention to the emotion that you're feeling. And it helps to be able to name it more specifically, so that you're really focusing on how that feels.

As I talked about, in my talk, as engineers and as white collar professionals and in this environment of professionalism that is, for the most part, what our workplaces are like, we're really supposed to exist from our sort of neck up. And not only from our neck up, but only as rational beings. And in fact, if you think about sort of the whole notion of Thinking Fast and Slow, much of the choices we make and the ways that we're behaving are driven by things that are non-rational in the way that we think of rationalism, and by feelings that we're actually mostly feeling in our bodies not in our heads. So, naming more specifically the kinds of pain that you might experience and really paying more attention to the experience of that pain, in not only the thoughts that we're having, "Oh, I failed. What if I'm going to be fired," but also, "How does that feel in my body," I think really makes it easier to live through and respond to the pain.

NOEL: What kinds of things are you talking about when you talk about suffering and pain at work? At most workplaces, I'm not being slapped or anything like that. But the pain and the suffering, I think, that you're talking about is real. And maybe you could talk a little bit about what the boundaries of that are and what the causes of it are.

AMY: Sure. I think there is a big spectrum. I touched on this a little bit at the beginning of the talk when I said, "These are some kinds of pain that I'm not going to speak about in this talk." And that was sort of the pain that is caused by being in a toxic workplace where people are backstabbing or lying, or there's no psychological safety, or there's a lot of uncertainty, or you feel judged all the time. That's a whole sort of bolus of different kinds of pain that you might feel in a workplace depending on how sort of safe it is. There's also pain that you kind of bring with you into your workplace because there's pain in your life and that doesn't go away just because you go sit down at your desk. If you have a sick child, or a parent in a nursing home, or you're worried about money, or you have a chronic health issue, those things are still causing pain at work to the extent that you may feel that you can't be open about them or ask for help about those things. You're kind of piling pain on top of pain. And then in the talk that I gave at RailsConf, I'm talking about kinds of pain, and there are more than the three types I talked about, of course, but kinds of pain that you're going to feel even in a wonderful workplace where you get to be as authentic as you can about everything that's going on in your life and nobody's actively deliberately causing you pain through sort of being toxic. Even in a really great workplace and even if you get to be honest about what's going on in your life, sometimes you're going to mess up, sometimes you're going to have to do really hard stuff that you don't know how to do. And that's going to involve a lot of uncertainty about whether you can accomplish it, and vulnerability about asking for help or sharing ideas that might be rejected that then might cause you to feel shame like, "I'm not good enough." In the talk, I talk explicitly about those three kinds of pain - the pain of failure, the pain of anxiety, and the pain of shame, sort of feeling like you're not good enough. And we'll all experience those both in and out of work, even when everything is really great.

NOEL: One of the things I definitely appreciated about the talk was the idea that even in a great workplace, even in a place where you can be authentic and get along, that you're still going to have these painful conflicts, that they're still going to be deadlines, that people are still going to ask you to do things that you don't necessarily want to do. That's why they pay us to come in, right?

AMY: Yeah.

NOEL: It's work and it's often mentally challenging and you are often pushing yourself to the boundaries of what you think you can do cognitively in a way that is stressful. What is a mistake that people commonly make when they feel failure, anxiety, or shame in a workplace? What is a mistake that people make that makes that feeling worse or deals that feeling unproductively?

AMY: There are probably two answers to that question. One thing that people will do is not notice that they are feeling that way. It's very easy to have an emotion and actually be basically dissociated from it and not recognize that you're feeling it. And when that occurs, it will influence your behavior in ways that you remain unaware of, but that other people are feeling.

NOEL: Stay away from Noel, who's really snappy today.

AMY: Yes. Exactly.

NOEL: Hypothetically.

AMY: Right. I see this, sometimes people will say something in a meeting and other people will be, "Oh, you seem upset." And the person will be like, "No, I'm not upset. What makes you think I'm upset?"

NOEL: "I'm not yelling."

AMY: Yeah, exactly. And so, it's this lack of recognition of the emotion that can really steer you wrong. And it's hard to deal with because in order to -- as a manager, when I see that happening, I want to be able to help people sort of see the emotion, see how it's affecting other people around them, and then be able to talk about the thing that's causing it. But if people don't want to see that they're feeling a certain way, that presents a bit of a challenge.

The second thing, I think is very unhelpful is this reaction that we jump to, if we do notice that we're feeling that way, "Oh, I shouldn't feel this way. Stop it. Stop it. Don't feel this way," which all the research has ever been done and pretty much everyone's sort of basic experience of trying to stop feeling a certain way that it's actually not possible and generally makes you feel more that way, because then you think, "Why can't I stop feeling this way?" It's just a sort of rat-hole.

NOEL: Yeah. You spiral.

AMY: Yeah.

NOEL: So, the spiral just causes you to -- you can't get rid of the original pain and you just cause yourself more pain by adding to your feeling of failure and anxiety by obsessing over the failure and anxiety.

AMY: Yes. And people have different personalities and different ways of dealing with pain. Some people are much more prone to notice and then obsess that they can't get out of that emotion. And then, there are people who are more prone to not noticing but kind of projecting it out on other people. I think the answer to both of those kinds of reactions to pain is really the same which is learning to pay attention. Learning to pay attention on what's going on non-judgmentally. And through that, being able to kind of move through the pain, whatever it is, to a more productive, or as I talk about in the talk, a skillful response to it.

NOEL: Right. You talk about a skillful response and that involves, I think, using these negative emotions of failure and the anxiety and shame and using them not just to help work past them but to help you improve in general. What are the skillful ways of doing that?

AMY: It's tricky because take failure, there is a very strong idea in software development that, and in sort of go-go venture tech Silicon Valley-land generally, that we learn from our failure. Failure is fine. We figure out the lessons and then we move on as quickly as possible to the next thing. So, you can sort of be too focused, "All right. How do I make myself a better person because of this?" In a kind of tense way, I think, that doesn't leave quite enough space to also feel the feeling.

NOEL: You can become so anxious about whether you're actually having a productive failure.

AMY: Yes. [Chuckles]

NOEL: That you start spiraling off in that direction.

AMY: Yes, exactly. For example, failure -- and I talk about this in the talk --  there's some research that it's actually the pain that you feel that is the thing that helps you not fail again. Not that you've done a really good blame-free retro and you have some things not to do in the future. There is a very popular talk format '10 Mistakes I Made That You Shouldn't Make'. And I like those talks and I always write those things down. But somehow, when it comes time for me to decide whether I should make the mistake or not, I think, "No, my situation is different. So, this is going to be fine." Whereas if I've actually made that mistake already and I felt that pain, I don't want to feel the pain again. So, I'm much more averse to doing that thing. For failure in particular, I think that the feeling of the pain is actually part of how you productively get better at making choices in the future because you're trying to avoid that pain.

NOEL: Table XI occasionally does this evening event called My Greatest Mistake where they invite a bunch of people to give like five or ten minute talks about the biggest mistake they've ever made. Our CEO likes to talk about the time that he lost a fight with a vending machine and hurt himself fairly badly. But he's okay now, so I can talk about it. Anyway, the thing that was striking about that to me is that even in this situation where people are going on stage to talk about their failures, people are very, very quick to re-conceptualize them as like not really failures. They have to be able to say, "This was a productive thing that I learned from," or, "This was only a failure when you look at it from the outside, but from the inside, it was a dramatic success." That even in this venue where we are like telling people, "Tell us about a failure that you made," that it is very, very hard for people to go up and say, "Yep, I screwed up. There was no redemption from this. I didn't learn anything valuable. I just made a mistake." It's very hard to do. But in some ways, might be useful to be able to do.

AMY: Yeah. Storytelling is a whole interesting topic in terms of how we, as you said, want to find the productiveness in the mistake or the good or, "Oh, this wasn't really a failure." And you're right. I think that there are very few venues where you could just feel like, "This sucked. I wish I'd never done that." I feel like people often will admit that about personal relationships that have failed badly, [laughs] more so than in a work context where we're all supposed to be kind of marching forward, upward, onward toward our best fast-company selves.

NOEL: If you're in an interview and the interviewer asks you like the biggest mistake you made, they want to hear that you learned a life lesson from it.

AMY: Yes, exactly. And we can often find life lessons from our failures but...

NOEL: It feels very pat to say, "I made this mistake, I learned this lesson and then I didn't make this mistake anymore." I don't think that's how it works for me except in very, very specific cases where I learned something factual.

AMY: Yes.

NOEL: Like I learned how to do something in Ruby, and so I didn't do something dumb anymore. But I don't feel like I get that sort of pat story in inter-coworker or interpersonal relationships.

AMY: Yeah. I think the more you get into sort of process or projects or what went wrong on a team, that a product was delivered late, all of those failures have so many different pieces to them that you will learn some lessons. The next situation will be different enough that you might say, "This time, it doesn't apply."

NOEL: And then you become a 20-year veteran and you kind of have instincts of, "This is going to hurt if I go this way."

AMY: Yes.

NOEL: And I'm not sure why, but I'm pretty sure it will. And you can't explain it.

AMY: Right. It's those instincts that are the things that are really steering you in the right direction. But yes, that is the knowledge that has been sort of wired into our bodies and our minds because of all the varieties of pain we've experienced over 20 years.

NOEL: Right when I first started, I was on a project that was -- failure is maybe the wrong word for the project as a whole. But I was on a project very early on that was extremely painful for a long period of time. And there were practices, there are practices that we did in that or that led to that situation that I avoided and still avoid now kind of instinctively because of that experience which is now almost 20 years ago. So, there's a certain training. [Chuckles]

AMY: One of the examples I used in the talk is this huge site redesign that I was involved in that was on a very, like months-long running branch. And it involved really touching all of the CSS on the site. At the same time, that people were still shipping features on Master and at the end of every sprint, someone had to merge all these changes and it would take like four hours minimum to do this. The accumulated pain of that has made me so averse to branches that are more than like two weeks old.

NOEL: Yeah I once watched a co-worker try to rebase in a long-standing branch and having to manually merge the Rails schema file because of the date stamp. He manually merged the Rails schema file in every commit for over, I think it had been like a nine-month or a year branch. It took him like a day and a half. And yeah, that was a rare case where I was able to learn from somebody else's pain because watching him do this was so...

AMY: Excruciating?

NOEL: Yeah, it was excruciating. I had very similar mistakes in that respect. Is there a possibility that we can over-learn these lessons that come out of the pain and suffering in a way that prevents us too strongly from doing things in the future?

AMY: It is very easy to learn from any sort of pain that you do not like the pain and so you will not do the thing that might result in the pain ever again. And the reason that I'm so passionate about helping people pay attention to their pain, acknowledge that it exists, and giving people tools that they can use to actually tolerate the pain is because the more you can tolerate the pain of trying stuff and working with people and screwing up, and you don't know what's going to happen and it's making you really anxious, the more you can tolerate all of these kinds of pain, the more cool stuff you can do because you know that you'll probably feel pain but you're confident that you can walk through it.

NOEL: You don't mean it like a stoic, "pain does not affect me" kind of way but more like in a resilient kind of a way that, "I know that this is going to happen and I'm going to be able to roll with it." Is that a fair way of saying it?

AMY: Yeah. It's not, "I'm going to ignore this pain. My leg's been cut off but I'm still dragging myself through the jungle with my 300-pound pack on my back. It's not bothering me." It's more that you know that you could feel like hell but you will get on the other side of it. It will be temporary. And you're confident that you're not going to die from the pain or be sort of permanently damaged from it, or never feel happiness or joy or competence or acceptance again. So you know that on the other side of the pain, you'll be OK and you will have accomplished whatever putting up with the pain allowed you to accomplish.

NOEL: Mitigating the pain in this context doesn't mean ignoring it and doesn't mean trying not to treat it if there might be larger issues involved. But it just means not letting the pain define the experiences that you can and can't have.

AMY: Yes. That is exactly what I mean and that's a really good point. If you are in a toxic situation, yes, part of dealing with that pain is finding the agency to get out of the toxic situation. If you have stuff going on in your head like I do, I certainly don't grit my teeth and bear it without medication, without all of the different ways that I try to assist myself to deal with a lot of emotional suffering that doesn't even necessarily come from anything in my life. It's just my brain chemistry. And that is also a skillful means of dealing with the pain.

I also want to address, I think, another way of dealing with the pain which is it's something we all do. It isn't a very skillful way to deal with the pain but I want to acknowledge it because I think no matter how much I sit here and talk about, "Oh, there are healthy ways to manage your pain and then you'll be able to have a bigger life." Sometimes, I get home from work and I pour myself a glass of scotch, and that is numbing the pain. And if I do it too much, then I'm numbing everything else in my life, too. I'm not really living my life. But I want to make space to acknowledge that it is a normal human behavior to sometimes deal with our pain by numbing it in whatever our chosen numbing way is. 

NOEL: That can, at least, be a short-term mitigation even if it doesn't solve the longer problem.

AMY: Yeah.

NOEL: There's a point where you watch a YouTube video to feel better and that's fine. But if you do it for 12 hours, then there's probably a better way to deal with your circumstance.

AMY: Right. 

NOEL: What are some of the things that people can sort of do to deal with these feelings in a more skillful way?

AMY: Sure. There are some things that you can keep in mind. Pain is temporary. You can look at your own past and look at times that you've been in pain and thought you would never feel better again. And that those times have passed and you can therefore extrapolate to your current pain and think, "Well, this doesn't feel like it will ever end. But I have past evidence to suggest that it will." Sometimes, you are going to be experiencing, for example, anxiety a lot. You can reality check with other people. "I'm very anxious about X. Are you anxious about X? Do you think we're doing enough to mitigate X? What is your reality?" We all are living in different realities and we try to come to some agreement about what's actually going on in the world. But to understand that the reality that I am experiencing is not the same as the reality my co-workers are experiencing and we can triangulate off one another to get closer to what's really going on. Sometimes, that can mitigate some kinds of pain.

NOEL: One thing that I do when I start to feel anxious, which is something that happens fairly regularly, is that I try to think about when I started to feel anxious and try to use that to try to figure out what actually is making me feel anxious and then trying to figure out whether that's a real thing in the world that I need to do something about or whether it's just my brain coming up with things for me to be anxious about and I can try to ignore it. And sometimes that helps. The hard part of it is getting to that first step of, "Oh, I feel anxious. When did this start?"

AMY: Right. Because anxiety, in particular -- failure will often hit you all at once. "Production is down and I'm the one who just pushed code." Anxiety feels like this thin sort of crack that's chasing you sometimes and it can be very hard to look back and see, "Well, where did it start and what is the thing that's causing it?" And I think that that's a very good thing to do is to try and find what's causing it and see, "Do I need to kind of nice that thought back down?" "OK, I'm not really dying of whatever I think I'm dying of this week." I'm a big hypochondriac. Or, "Oh yeah, maybe there are some security issues that we should consider as we're adding this feature to the app, and let's ensure that we have a really good test plan in place here." So, those are two different kinds of -- one of those anxieties is actually really sort of helpful to doing a good job. And the other is just like, "OK. For whatever reason, I'm anxious and that's not based in reality. And I can let that anxiety run in the background until it sort of runs itself out."

NOEL: Are there other strategies that people can use to manage their work-related pain?

AMY: Sure. I'm a big proponent of mindfulness. I know that just everybody in the entire universe is a big proponent of mindfulness right now and there's a lot of great scientific research about it and there's about a billion mindfulness apps that you can download. But just because it's popular doesn't mean that it is not actually one of the best things that you can be doing to help yourself manage pain. I really like a mindfulness teacher named Tara Brach. She's also a psychologist and she teaches a really simple process for mindfulness of pain and suffering in the moment that I think can be really useful. It's called RAIN. It starts with recognizing, "Oh, I'm feeling this emotion..." At the beginning of this conversation, I talked about sort of the situation where people don't even recognize that they're feeling an emotion even though everybody else around them does. So, recognizing that you're feeling an emotion and then sort of allowing that emotion instead of saying, "No, I shouldn't feel this way." "OK, this is how I'm feeling. Let me next investigate how the emotion feels in our bodies and in our minds. What are the thoughts that are going with it? How does it feel in my stomach, in my heart, in my arms, in my feet?" It's constantly changing. Our pain is constantly changing. It's very bodily. It's kind of interesting when you stop running from it and start paying attention to it just to see what it feels like, and paying attention to what it feels like. It reduces the suffering because you're spending less energy running from it. Running from your pain takes a lot of energy. So, investigating. And then, the end in RAIN is for nurturing and that's really giving yourself some compassion. If you messed up, if you're feeling insecure, you're feeling this pain. We all feel pain. None of us really deserve to feel pain. We can treat ourselves like a friend we love and comfort ourselves because we're feeling bad, and then really recognize that all of that stuff, the thoughts and the churn and the pain, that there's something bigger than that that we can watch. This is, I think, the number one thing I've learned from mindfulness and I've been practicing mindfulness for 16 years now. I started when my son was born. That you can step back from the churn and sort of be the sky instead of the clouds is what a lot of the teachers will give as a metaphor. And sometimes, you can only do that for like five seconds.

[Chuckles]

AMY: But it's a very powerful five seconds.

NOEL: And then five seconds can become 10 and hopefully...

AMY: Yes.

NOEL: You can move forward.

AMY: Yeah. 

NOEL: I like that, the being the sky and not the clouds. You are not your worst day, I think, is another similar kind of phrase that I sometimes think about.

AMY: Yeah. We're not our thoughts and we're not our feelings. Who knows what we are? But we're none of those things.

NOEL: Yeah. Not letting yourself become defined by the pain and the suffering seems like kind of a thread of all of these techniques.

AMY: Yes. And I think becoming defined by anything is really very limiting. Part of my persona is I have a lot of boots. It fits me and I love boots. It's true. But I'm bigger than a Director of Engineering with a lot of boots and a love of scotch and bipolar disordered. I'm bigger than my identity because all of those things are in kind of thoughts and feelings and presentation. And again, that's kind of the clouds. It's not the sky.

NOEL: To be like a little more self-indulgent than I normally am, I always, for a long time, perceived myself as like "the testing guy" because I was writing these books about testing. And I remember very clearly the DHH keynote at RailsConf in Chicago in 2014 which was very much about how like people with advanced degrees are ruining the Ruby community and consultants are ruining the Ruby community and people who are advocating for testing are ruining the Ruby community. I was like, "Check, check, check."

It took me a long time to sort of process what I felt in that moment. Somebody else actually sort of correctly identified it as like a form of shame that I was feeling that I had been kind of called out, not by name, but by sort of reputationally. And it felt really weird for a long time. It did feel a little bit better once I was kind of able to sort of conceptualize it in this way that it wasn't really about me. This is not really me. This is not what I provide to the community. This is not what I provide in my job. These are just parts of what I do. But it was definitely an experience that I had that felt like super personal and probably shouldn't have. And until I was able to conceptualize why it felt super personal, I wasn't able to let go of it. 

AMY: That's really interesting. I am almost done reading a book called Thanks for the Feedback which is a fascinating book about how to get better receiving feedback even from people who maybe give feedback the way DHH gives feedback.

NOEL: I have a lot of opinions about feedback.

AMY: [Laughs] Oh, yeah. We talked about that. I look forward to talking more about that at some future moment. But one of the things this book talks about is that when feedback attacks something that we feel as our identity or that it feels particularly, like it's particularly hard to take in, that any attack on our identity is painful. Paul Graham wrote some blog posts that I always have a hard time finding when I'm looking for it, but it's about that. It's about holding your identity more lightly so that you can live more flexibly. I'm not sure how to relate that into pain and suffering.

NOEL: [Chuckles] I think it definitely involves a certain amount of pain. You talked about shame in the talk and we haven't really talked about it much here, but there is a sense of like, "You're attacking my identity. That makes me worth less."
 
AMY: Yes. Brene Brown has done all of this great research about how incredibly just devastating painful shame is and how much of it we feel, and how experiencing shame in unskillful way is so detrimental to our ability to live bigger lives or behave as we would like. I see this a lot actually in my role as a mother because the entire culture attacks everything mothers do, no matter what we do, at all times. And so, I'll find myself interacting with one of my children out of shame that someone out there is judging me for not doing a good enough job. And that makes me so much more sort of angry. "You have to do this. If you don't do this, I am not a good mother." And this happens in the workplace, as well. You want to control someone else's behavior because you are expected to be able to control something and you can't. So, you try to get other people to. I don't think that makes any sense actually.

NOEL: No, it does. You feel like you're going to be judged for somebody else's behavior which leads you to sort of try to control them in a way that is not necessarily helpful.

AMY: Right. 

NOEL: That's definitely something that would happen in an engineering management kind of context.

AMY: Luckily, as I think I said engineering, engineers are definitely easier to manage than children. And yes, certainly, I've seen it in myself in the past when projects are not going as well as I would like. And in previous jobs where I've gotten pressure, "Oh, this isn't going fast enough." And then I feel ashamed that I'm failing. It's extremely easy as a manager to push that chain down onto the people who report to you. And it's one of the things that I've become extremely aware of, through some experiences of doing that. And not like destroying other people particularly but just causing more stress for people who worked for me than I would have wanted to do. And so, I've really learned from that how much I need, as a manager, to manage my own emotions so that I'm not pushing those down further on the people who are reporting to me because that does not make anything better.

NOEL: Yeah. It has been really great to talk to you, Amy. And where can people find you if they want to continue this conversation with you?

AMY: I think probably just @AmyNewell on Twitter is the easiest place.

NOEL: Great. Amy, thank you for coming on the show. Really glad we got a chance to talk.

AMY: Thanks so much for having me. It was great.

NOEL: Tech Done Right is available on the web at TechDoneRight.io where you can learn more about our guests and comment on our episodes. Find us wherever you listen to podcasts. And if you like the show, tell a friend or an enemy, or your social media network or your anti-social media network, or your pets, or tell me. Leaving a review on Apple podcasts is also a great way to help people find the show.

Tech Done Right is hosted by me, Noel Rappin. Our editor is Mandy Moore. You can find us on Twitter @NoelRap and @TheRubyRep. 

Tech Done Right is produced by Table XI. Table XI is a custom design and software company in Chicago. We've been named one of Inc. Magazine's Best Workplaces and we're a top-rated custom software development company on clutch.co. You can learn more about working with us or working for us at TableXI.com or follow us on Twitter @TableXI. We'll be back in a couple of weeks with the next episode of Tech Done Right.