8. Navigating a Lasting Career: The Adventures of Women in Tech

Alexis and Alana Karen, an award-winning author who spent over 23 years at Google, explore the question of how to navigate a long and enduring career as a woman in tech. In this raw and honest conversation, they discuss the realities women face in the tech industry and the tools needed to not just survive, but thrive.

What does it take to build a lasting career in tech when you're one of only a few women in the room? Behind the glossy media articles questioning whether women can "make it" in tech lies a more nuanced reality, one where resilience, community, and strategic self-advocacy are the keys to navigating a lasting career in tech.

After interviewing 80 women across the industry, Alana distilled their collective wisdom into five essential tools. They explore how these skills create staying power in an industry where it can feel like you don't belong.

As tech confronts a new wave of challenges, from layoffs to ethical questions about AI, they examine what's changed since Alana first published her book. Where she originally emphasized belonging, her upcoming fifth-anniversary edition explores agency in an industry where trust has eroded. As for the key to a lasting career? A delicate balance of patience and strategic action, knowing when to endure difficult periods and when to pivot toward growth and change.

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In this episode:

• [1:27] Background on today's guest, Alana Karen
• [2:00] Alexis' career journey: the good, the bad, the ugly
• [12:15] Alana: welcome and introduction
• [17:13] Why Alana wrote "The Adventures of Women in Tech"
• [25:10] Five essential tools for women in tech
• [34:04] The Fifth Anniversary Edition: a sneak peek!
• [43:42] Power moves: career pivots and growth
• [59:50] Advice for long-term career success

Find Alana:

• Website: alanakaren.com  
• LinkedIn
• Sign up for her Newsletter

References:

• Alana’s book: The Adventures of Women in Tech
• Alana’s workbook: The Adventures of Women in Tech Workbook
• Previous episode: Navigating Burnout
• Jonathan Haidt: The Anxious Generation
• Alana's Interview with Sheryl Sandberg

Chapters

• 1:27 Background on today's guest: Alana Karen
• 2:00 Alexis' career journey: the good, the bad, the ugly
• 12:15 Alana: Welcome and introduction
• 17:13 Why Alana Wrote "The Adventures of Women in Tech"
• 25:10 Five essential tools for women in tech
• 34:04 The Fifth Anniversary Edition: a sneak peek!
• 43:42 Power moves: our career pivots that led to growth
• 59:50 Advice for long-term career success

Transcript

Alexis: 0:05

Hey, I'm Alexis Booth and welcome to the Breakout Booth. I was a senior manager at Google. I'm a wife and a mother, and I learned the hard way If you're not fired up, you're on hold. I believe success is closer than you think. There's a set of skills and habits you can grow to unlock unbelievable outcomes. In this podcast, we'll explore them through real talk and bold conversation, because I want to help you break out.

Alexis: 0:40

Hey there, folks, and welcome to the Breakout Booth.

Alexis: 0:43

I'm Alexis Booth, and today we are going to discuss how to navigate a lasting career. Longevity and endurance are the two words I invite you to keep in mind throughout the episode. Now we'll specifically discuss this in the context of being a woman in tech, but I believe a lot of the themes we'll explore are relevant to many different industries and paths, and it'll be useful for you to listen in, no matter how you identify. In case it's not obvious why I'm focusing on women in tech, well, it's who I am and it's what I've spent the past 25 years doing. It's my own lived experience.

Alexis: 1:22

But beyond that, our guest for today literally wrote the book on it. In just a little bit, we'll bring Alana Karen to the mic. She wrote this beautiful book titled "the adventures of women in tech how we got here and why we stay. In addition to getting my official thumbs up, it's won several shiny awards and it's also been celebrated in quite a few different places and forums. Alana is also currently working on a fifth anniversary edition of the book, which will include some reflections on what has happened in the years since she first published it.

Alexis: 2:00

But before we dive into our discussion with Alana today, I'd like to share some reflections on my own adventures as a woman in tech. Going back through her book helped me realize that so many of the things that I've loved about tech, as well as the things I've struggled with over the years many of which I've never talked about with bosses or colleagues because I thought they'd make me look weak are actually common threads that I share with so many other people. Since I love the rule of threes, that's how we're going to talk about my experiences today the good, the bad and the ugly.

Alexis: 2:40

First off, let's talk about the good stuff

Alexis: 2:42

.

Alexis: 2:43

I love solving technical problems. Tech gave me the opportunity to tinker and play on a daily basis, but not only did it give me access to fascinating problems and a constant stream of puzzles to wrap my brain around. I actually got paid to do it. It's been incredibly satisfying and gratifying to do tech work. Even as a young kid, I was naturally drawn to toys and challenges that fit in the spaces of math, science and the arts. When I was in elementary school, I used to spend hours upon hours playing ColecoVision that is old school gaming right there, nintendo and later on Sega, although I gravitated toward games that involved solving puzzles, not guns and killing.

Alexis: 3:35

In high school I wrote math programs on my TI-85 graphing calculator. It wasn't part of any assignment. No one told me to do it, but someone else showed me something they'd made and I wondered if I could do it too. It turns out I could and I thought it was the coolest thing ever. In college, my favorite class in my entire four years of study was Java programming. So if I were to describe why I love tech in bigger terms, I love the challenge of problem solving and I especially love tech because the problems in it ultimately have a binary answer. You build a

Alexis: 4:16

thing and it either works or it doesn't. You know right away if your code compiles and whether or not the application you wrote satisfies the set of requirements or plans that you imagined when you designed it For me. I love the types of problems that I've been able to work on in tech.

Alexis: 4:38

On to our second point, let's talk about the bad. I am a rarity as a woman in tech, and that's not a good thing. It's lonely and I've often felt like I'm on an island all by myself. Also, tell you what I'm not alone in feeling alone. It's why community and belonging are so incredibly important for us to forge and find as women in tech. As for exactly how lonely it is, a quick round of research suggests that women currently hold somewhere between 20 and 30 percent of tech jobs on the whole, which is pretty consistent with what I've heard over the years. So, basically, for every one woman in tech, there's three guys, and while

Alexis: 5:25

I do want to celebrate the fact that many of the men I have had the privilege of working with over the years are fantastic human beings, but there have also been plenty of dudes and bros that repeatedly talk over me mansplain things problem: that sexual no,

Alexis: 5:45

I really don't need to hear from you, or they exhibit a particularly irritating quality where they don't hear something valuable I have to say, and then two minutes later they echo the very same point I just made and get rewarded with a room full of ahas or a thing that you'll never hear me describe in a positive sense violent agreement. What the hell even is that? And if I had a nickel for every time that I was the only woman in a work meeting, let's just say I would have a very, very heavy piggy bank, very heavy piggy bank.

Alexis: 6:29

There is an incredible wealth of research that demonstrates the value of diversity. It is beneficial to a company's bottom line and if you're creating products for the masses. 50% of human beings on the planet are female, and herein is the difficulty of being a rarity as a woman in tech and the reason that I've filed it in the bad category. There are plenty of other folks who do not believe in the value of diversity. It's a problem that definitely qualifies as outside of my control, which means it's something I've inevitably had to learn how to deal with, and I could easily talk about all the twists and turns I made on my lonely path as a woman in tech. But I want to make sure we touch upon one other topic today, and that is the ugly. There are several deep and difficult challenges that I'd put in this category, but the one I'm going to focus on here is an age-old problem Sexual harassment.

Alexis: 7:35

I personally endured a lot of things, especially early on in my career, that made it difficult to stick it out as a young woman in tech. I was hit on, I heard inappropriate jokes and I experienced microaggressions so often, especially in the first 10 years of my career, that I simply learned to filter out the noise and I was conditioned to think that doing so was part of the job. I had to develop resilience and thick skin real fast if I wanted to survive and tough it out. Within four months of starting my first job after college, I was groped by a senior colleague after he told me a totally inappropriate not-safe-for work story. I've been stalked by a coworker and pursued by someone else persistently, despite turning them down many times, and I stuck it out for far too long in a particularly gross workplace where in the first week of my job there, my boss made jokes with sexual innuendo about me to a client that we were pitching, and when I walked into his office for a one-on-one meeting in that first week there was a big screen TV on the wall playing porn I'm not joking. And when I made a stink about it, the guy played it off like it was my problem that I couldn't just avert my eyes and shut my ears. He totally gaslit me in the moment, but I stuck it out because I needed the job. I was reeling from being laid off and I was already swimming in thousands of dollars of debt.

Alexis: 9:21

Sadly, there are many other women who have experienced far worse things than I did. I do suppose I did learn one thing early on as a result of all of this, which is how to have direct and uncomfortable conversations with people who are way out of line, but I wouldn't wish these experiences upon anyone. It's also worth noting the first four places I worked were all incredibly small businesses, and only one of them even had an HR person. This is not a department, it was an individual. So while the challenges and mistrust of HR departments is well known, it's also not great when you're at a business that's too small to Karen even

Alexis: 10:07

have one.

Alana: 10:08

Now

Alexis: 10:09

, thankfully, the proactive acts

Alexis: 10:11

that I took to call out bad behavior and take a stand against these men made it clear I wasn't interested. I wasn't having it and for the most part, it prevented future occurrences, but it also left me with an overwhelming feeling that I always had to be

Alexis: 10:29

ready to defend myself, and I learned a necessary but unfortunate habit of putting up walls to protect myself as soon as I stepped into the building of my workplace. It wasn't until I'd already been at Google for several years so this was well beyond 10 years into my career that I was finally able to set down my mask of self-preservation and start bringing my full self to work. There were two male leaders in particular that I consider myself incredibly lucky to have worked under Alex and Patrick. They created a safe environment at work that made all the difference in the world for me. So, in case either of you ever happened to hear this episode, thank you. You changed my life in far more ways than you probably know.

Alexis: 11:26

Now, let's be clear no one should be put through these types of situations, but the reality is it happens, and I think your best bet is to be prepared for it. My number one piece of advice is to take a self-defense class. If you haven't, they're a great way for you to boost your own sense of confidence that you can handle an unexpected situation where your body is at risk. Now there's plenty more stories that I would love to share with you about my career journey, but they are simply going to have to wait for another time, because I'm super excited to bring to the mic the one and only Alana Karen. Thank you for joining me today and welcome to the Breakout Booth.

Alana: 12:19

Thank you for having me.

Alexis: 12:20

Whenever you're bringing someone up on stage or you're getting ready for a first one-on-one with someone, what are some of the things that you do to help get them comfortable? A first one-on-one with someone what are some of the things that you do to help get them comfortable?

Alana: 12:29

I like really rely on humor maybe too much, honestly. So I think I'm always like a little jokey about something. I'm a little self-deprecating. I think I got used to that at Google because as I got longer tenured I found that a lot of times people knew that and were already sort of pre-scared of me, which is hilarious because I'm like five foot one and really not that scary. But I think that just that sense of like wow, she's been here 10 years, she's been here, however, long. So I think I just got into a habit of sort of being a little jokey, a little self-deprecating. A good amount of eye contact unless they are someone who doesn't love eye contact and I can usually pick up on that pretty quickly just paying attention to physical cues and usually just like easy questions at first Life, anything you would just know. So that's usually my go-to ingredient.

Alexis: 13:29

All right. Well, I love that. That is awesome. Alana is a well-known female leader in the world of tech. She spent the majority of her career - 23 years at Google! But the last 16 of that or so was as an executive. So not only were you shaping the people who were on your teams, you were actually shaping the company as a whole, which is just really cool. And over the last 10 years or so, Alana has really leaned in to giving back and stepping up as a role model and as an advocate to women in tech across the globe.

Alexis: 14:09

I never got the chance to actually work with Alana directly when we were at Google, but I do recall a discussion that she graciously hosted for the women's ERG that I'd co-founded. She'd shared some of the key messages from the book and reflected on people's reactions to it. But I also remember asking a question at the end of the session, because the discussion was right after my first time of getting rejected in my pursuit of becoming a director there. I was still nursing an open wound because I didn't get it.

Alexis: 14:36

But what Alana offered in that discussion was compassion. She gave me some advice and it came from her own experience of having gone through similar stuff in her own experience and, perhaps most importantly, she made me feel heard. She didn't know me, but I knew she cared about what I was feeling and what I had to say, and she knew what I was struggling with. And so she couldn't give me a promotion, but she gave me the next best thing that I could have asked for. Can you share a little bit more about yourself and the things that you're most passionate about with our listeners?

Alana: 15:13

Sure, I mean, you covered my career very well. I got into tech not accidentally, but my educational background had nothing to do with it. I was a history major, I did like creative writing. I could have minored in French but I gave up, like I was very much humanities. But in college I got interested in the then new world of web design and creating websites for the world and self-taught myself HTML, some JavaScript et cetera, and just forged a path there for myself on the side, which ended up becoming my entrance into tech later, first as a webmaster and then at another startup and then at Google.

Alana: 16:03

So I think that I'm just like a big proponent of people of different backgrounds exploring tech. Because of that, I think it added a lot to my career. It's a huge part of my identity. I fancy myself as creative, even though I didn't necessarily go down that career path, and I think, separately from that, I am a mom. I have three kids, two dogs and a cat, which you know you never know when they'll show up, so we might hear them at some point and I think that gave me like another balancing characteristic to my journey through tech. At the same time that I was becoming a leader, I also became a parent, and so I think what you were talking about in terms of sensing that I really cared was a characteristic throughout that I was building this. What would it be to be a people-focused leader, and what would that look like in the workplace? That was often very business or finance-focused or product-focused. What would that look like to forge that for myself? So definitely some big themes you've picked up on there, cool.

Alexis: 17:10

Well, thank you so much for being here today. Let's start off this discussion exploring some of the backstory around the book that you wrote several years ago now. What led you to do the work in the first place, and what's the reaction been to your book?

Alana: 17:27

I was really annoyed. It's always how I start, it's even in the book jacket, because I do think sometimes a passion project. I was working full time. My youngest was like maybe three years old.

Alana: 17:42

I think taking on something like writing a book sometimes needs a real spark, and for me it was annoyance, both where I saw the overall market heading but also just personally for myself, and what I was seeing was that the Me Too movement, which had been very useful in getting out stories that needed to be out, was also producing kind of a chilling effect in the media, where the articles that I was seeing had sexy headlines like can women even make it in tech? Like should women come to tech, and I was like, who are these articles benefiting? Like, when you are an editor at a newspaper, you don't understand the high schoolers, the college kids, the women in tech that are going to see that and what that's going to mean to them. And so, instead of the feeling being like, oh, here are the challenges we need to address, it was much more like oh, maybe you shouldn't even bother ladies, even though most industries have challenges and that's just known for.

Alana: 18:53

So it was just sexy headlines and people not realizing what it meant. And, at the same time, when you looked at books that were out there, often the books captured the stories of women who'd made it to the tippy top but didn't necessarily represent the majority that hadn't. And I also wasn't seeing stories about women of all different types, all different backgrounds, all different paths, non-technical and technical who journeyed through tech. And I just had one of these moments, kind of triggered by my own angst, where I was like I can write that book. I know people. I call it Google hubris, by the way, because I've been at Google so long that you start to just think like there's a problem, I can solve it, I get it. And I don't think I would have thought that way earlier in my career. I think it definitely was like something I learned along the way, you know. So I just started doing it. I did it in my evenings, I did holidays, I did it all the time I wrote it. I, you know, figured out how to self-publish when I realized I wouldn't be able to get a publisher.

Alana: 19:59

That's a whole anecdote in a traditional industry. But in the end, I thought the reception was what I was looking for, honestly, which was I would hear back from people who said, oh yeah, I like saw myself, or I wouldn't have done this, or I wouldn't have thought I could do it if I hadn't read that at that time, or even if the book as a whole you know, they weren't huge commenters on it they would be like that story that I saw that story was really helpful. And so I think that's what I was looking for was really this, this thing that if you were looking for yourself or you were looking for evidence that you could belong, that you would find it.

Alexis: 20:44

I love that.

Alexis: 20:45

It's really cool. It's funny. You're saying you were irritated or you were annoyed. I'd actually say that my own reasons for the podcast. I spent my own second half of Google as a senior manager.

Alexis: 20:55

I was responsible for growing teams and hiring people, but I, as a woman who wanted to have more women around me, I and the recruiting teams that I was working with we could not find women to bring in. And it wasn't just a matter of we had these like really diverse sets of candidates who were coming through and it was just like at that last interview, like nope, we're gonna give it to the guy. When you think about hiring, it's a funnel. It starts with all of the leads and the potential you know people you're going after. There were no women in it and in fact it wasn't just women, it was diversity of all forms, and we did a lot of things trying to go after this. I did a lot of my own personal outreach. I was trying to find people. So if they weren't applying, they must be out there somewhere. Let me go find them. I could not find them. And ultimately what it led to was I was unsuccessful in building a team that was as diverse as I wish that I could have, and what I realized is that if I wanted to actually make a difference, I had to get myself inserted earlier in the pipeline and actually make a difference. Too many young women and girls are dropping out of tech way before they would have ever been able to send me a resume if they're even getting to college to pursue technical fields. Or, like your experience, you didn't get a comp sci degree but actually you have the ability to do tech and you picked it up later on. There's all sorts of different profiles of people who have excelled and done amazing things.

Alexis: 22:45

Now the second part of my story.

Alexis: 22:47

I've talked about burnout in a previous episode, but the long and short of it is I had to hit rock bottom in my mental health to get there, and then I had to find a coach who was capable of actually calling me out and helping me unwind all of these pieces along the way. This is not something that we teach people how to do and, in fact, if you find yourself being burned out as an adult, what you have to do is unwind a belief system that started in your childhood and you have to like dismantle it and start over. And it's a long process. Ultimately it's with a lot of little steps along the way, but that's really what I'm trying to help bring to the forefront here is helping people see these little tiny things that can start becoming bigger and bigger shifts, because I think this is also part of this set of skills that you need to be able to sustain a long career. If you can't manage your energy and you're hitting burnout, you have to change what's going on before you can actually fix it.

Alana: 23:53

Yeah, absolutely. And I don't think a lot of us were taught to value ourself or think about what long-term would look like. I think we were very much taught to just win, win, win, win, win, succeed, succeed, succeed and then you will be successful in life. And I grew up in New Jersey where no one even brought up happiness for the record.

Alexis: 24:19

T he armpit of America, as I sometimes - sorry if you're from New Jersey!

Alana: 24:27

I don't know if any East Coasters are listening.

Alexis: 24:29

Well, I lived in New York for a long time and definitely, my Midwest mindset changed a lot when I was living there and I came back from

Alana: 24:38

There was no East Coast sense that you were aiming for happiness, to be clear.

Alana: 24:45

Like, this is very much like the other parts of the country maybe, cool.

Alexis: 24:49

Let's come back to our discussion here. I would love to go into all of the different skills and habits that are in the book, but since we have problems with attention in our culture today, we're going to go to shortcuts.

Alexis: 25:02

What are the shortcuts that we can all take? What are the hacks and the tricks? Because we just need to go straight to the punchline.

Alana: 25:10

Straight to the punchline. Yeah, I talk about - after having interviewed 80 women and talking about their challenges and things that they learned along the way, I boiled it down to five main tools that, if people were attentive to, it, would certainly help them in their careers, because it clearly helped these women as they formed them along the way. And often it would take a while for these women to realize that like they needed to work on something.

Alana: 25:38

So can we just cut to the chase, tell you what they were all earlier and speed this all up for us, and the five things were resilience, the ability to get up when you fall down, the ability to like keep going after you don't get that promo right. Number two self-marketing marketing 101, something that women often either don't learn or when they first try to do it are basically like put down for it or face penalties.

Alexis: 26:05

It gets called bragging or we're trying to be too humble, Like we value humility which comes at the expense of actually letting people know what you do and you're good at. Absolutely.

Alana: 26:17

Related: ask for it. Ask for what you want. Ask for what you need. Fourthly, finding support. A lot of us go it alone and then, in fact, it's a value of independence of us go it alone and then, in fact, it's a value of independence, but then that ends up harming us over the long run. And then, lastly, owning your awesome, which is probably the thing that takes the longest to do in our careers, but to feel inherently that we are amazing and valuable without anyone telling us for it, and that we are inherently worth the other things.

Alana: 26:49

So if I'm giving you quick hacks, I would probably say finding support. I think it's probably the tool that naturally leads to the other ones.

Alexis: 27:00

Sure.

Alana: 27:01

And it can go in all kinds. I think sometimes we over talk about, for instance, mentorship or sponsorship, which can sound like a lot of effort, and like you're marrying someone and I prefer to talk to people about speed dating. What about if you just have little interactions with lots of people? You request a half hour one-on-one because you saw that they're great at giving presentations and you want to learn their quick tips. You ask for, like, a coffee chat because you saw them describe their work really well and you're trying to figure out how you describe your work better and you just want to have a conversation about that, right, I think too often we're like is this person wonderful and amazing at all things and would they take the time to talk with me? Oh my gosh, I'm nobody, I won't reach out, yeah.

Alexis: 27:54

I actually love the way that you just described even the... maybe you're not even looking for a mentor, or at least out of the gate, that's not what you're asking for. You're simply going like, Alana, wow, I saw you do this presentation. It was so amazing. How did you do that? Can we have just, you know, 20, 30 minute chat, like I'd love to know how you got to that. And so you're like, oh, I could talk about that for hours, like sure, and I appreciate how forthright you're being in this request, but I think one of the things that I've always had a challenge with is I know I need more mentors, or I'm supposed to have more of them, but it feel, you know, like the alternative of what I've always thought it's supposed to be is like hey, Alana, you don't know me. You're really cool, can you be my mentor?

Alana: 28:48

Totally. Will you be my mommy. Like that little book where, like you, just like wander around asking people to be your mommy.

Alexis: 28:53

That does not work.

Alana: 28:54

Yeah, no, it's terrifying. And so it sets up this like weird blocker that most people are never able to get over, whereas I think that this is so much easier. Like you, you've paid attention to something that you like about the person. You go, you compliment them about it and you ask for a minimal amount of time and most people not everyone, but most people will say yes to that, mainly because you complimented them, but also because you're respecting their time. It sounds finite. It's easy to do right Now.

Alana: 29:25

If you click, you can always try to translate that into like oh, you know what I'd love could, could we do this quarterly? That was so valuable. You could always try to turn it into a long term relationship, but either way, you've built that connection and the next time you have a question about that, you could go back and say hey, I remember we had this great conversation about this. I have this follow-up, and just building a bunch of those starts to build you this network that I think then you might be able to do the next thing, which is build a little board for yourself, right, like you've got maybe five people you go to when you're about to make a job change and they help talk to you, and then maybe it graduates to the next thing where you've got a couple people who will call you on your crap and say, hey, you're not describing your work well.

Alexis: 30:15

So I think it's just a great beginning, stepping stone, and it gets the fear out of networking which most of us and I love where you're going with this too of their very tactical interactions and they can be in the context of a much deeper and longer relationship, but it's I need time to talk about this particular thing. I think one of the things that, as I'd signed up for mentor programs and I offered myself on different forums that we had mentoring and I'd have people show up and they're like, Hi, I'm here. I was like, okay, step one of this discussion is for you to tell me what you want, and oftentimes that wound up being like, oh well, what do I want? Well, what should I want? Coming back to some of your shortcuts, it's really you know, knowing what it is that you want.

Alexis: 31:04

I'd say for me some of my shortcuts that I would talk about, there's really two of them, and the first one is notice the things that I'm curious about or that bring me energy, or, on the flip side, notice the things that deplete me. And then part two is do more of the good stuff and less of the bad stuff..

Alexis: 31:26

You know, when I was burned out, literally the way that I got through it I took a week off of work and I dug up my yard. I was like your dog. I was planting shrubbery and flowers.

Alana: 31:38

I like how you said shrubbery.

Alexis: 31:40

Shrubbery. So, I was like getting my hands dirty and then, over the course of the next several months, I watched things grow and I also watched a lot of things die and it was like, oh, I guess that didn't work, let's try something else. But it was this... it was this like beautiful thing. I'd never gotten into gardening and suddenly I had this like wonderful thing that just brought me joy and energy and it was something to look forward to. It keeps you moving forward rather than stagnating in a place that, ultimately, when you're stagnating, those are the things that are depleting you, those are the things that are not filling your life with joy and goodness.

Alana: 32:19

The only thing I will say is and I think you're treating this quite healthily I have seen people use it unhealthily, where they literally don't want to do anything they don't want to do, and then you're coaching in the opposite, which is like well, every job has some percent of treachery,

Alexis: 32:37

100%. Well, not 100% of the job, 100%, agree with you.

Alana: 32:41

Yeah, you can never have like a hundred, like there's always a 20% of record keeping, 20% of something manual Like, and I think that I would see people misperceive that if you were getting more senior, you would stop doing those things, you would graduate out of them.

Alana: 32:59

And then they would tell themselves the story that they were too senior for that, and then I would have to say, as like a senior director, no, no, no, every job has this stuff. But I like what you're talking about in terms of your energy, right Like you are paying attention to what gives you energy and you are trying to make more and more of your job reflect that.

Alexis: 33:20

I agree with you. I also do personally think, when I go back in my own career and I look at other people, I do think that there are periods that you definitely need to double down and like really dig deep into things that are hard if you're going to grow and get better. And I do think you should always be focusing on maximizing the positives and the good things that you have. But ultimately, if you don't address the things that you're not good at or you're not well, it's really if you're not focusing on or you're not well, it's really if you're not focusing on progressing those things they will hold you back. So I do think that's a reality, but it's not a shortcut. That's actually like the some of the tough stuff that I think you need to do.

Alana: 34:00

Yeah, a little bit of a hidden, hidden problem that could get you later.

Alexis: 34:04

All right. So you have been working on a fifth anniversary edition of your book. Can you give us a little preview of what you are expecting in it?

Alana: 34:14

Yeah, a little sneak peek. So, like I said earlier, the first book really focused on this kernel of a problem, which was the story of belonging, and the book really focused on then telling stories about people from all different backgrounds making their way into tech. All different jobs, all different paths, Then some of the challenges that they face and the skills that help them. But overall, a pretty positive tilt on the whole. Come to tech because you could and it's and people can have meaningful careers here and don't tell yourself you can't right Like you could belong to you.

Alana: 34:58

Fast forward five years and I felt like maybe a little bit more had to be written, Because tech has gone through a journey where a lot of people are feeling let down, disappointed, and some of it has to do with the maturation of big tech becoming quite traditional. Some of it has to do with what happened during the whole pandemic arc with getting more flexibility and then having it retract, taken away and now having to come back to the office. Some of it has to do with the overall product direction of tech. Is it really solving the world's problems? What's happening with AI? Are we creating more problems than we are solving? So there's all kinds of aspects to it, but I felt like not having written about that and talking about oh, do you want tech? What's going on with it, what is our journey through it, what are our paths through it and what has happened Like a little bit of group therapy what has happened in tech over the last handful of years giving people doubts, pause, et cetera and how is that then relating to how we're thinking about whether we want to stay in tech, leave tech, et cetera? So a bit of a fast forward five years. Oh, wait a second. Where are we with all of this?

Alana: 36:30

And I just felt pretty haunted by the fact that if I didn't write more, that it would end up being this weird like archaic view of tech.

Alana: 36:44

But also I liked the idea of coming back to it five years later. There was something pleasing about this idea that if you're talking about an adventure of women in tech, the adventure is long, the adventure will have ups and downs, and where are we on that journey. So I'm adding a few chapters that really focus on that sort of history of where we are, the trust loss that we're seeing in tech as an industry, but also the tech major, tech employers, and what's that mean for the space? And then where we go from here. What are the different paths women seem to be taking? Honestly, I will say that the addition is probably quite a bit more gender neutral, because I do think all genders are probably facing very similar questions in this regard, but women continue to lag in all the major metrics. Minorities continue to lag in all the major metrics in tech, so I still think it might be more prevalent in certain places, and so I'm continuing my minority focus take.

Alexis: 37:46

I think it's really cool, the first one is really you can belong. The additional chapters, it sounds like, will be more like do you choose to belong?

Alana: 37:58

You chose to, and I talk a lot about agency in the addition, because I do think that one of the things tech was really benefiting from was that it was the hottest thing around and that then all the companies really made it seem like an imperative everything that they were doing, and that it was an imperative to be your everything.

Alana: 38:26

You would succeed. And that was true for a lot of people for a while not everyone, but it was a pretty common tale to hear people join tech and grow quickly and continue to make more and more money. But all of a sudden the stories changed. All of a sudden the stories are like well, maybe you joined and then you were laid off, or maybe you were employed by that company for years and then one day they laid you off with no notice, right, and that really breaks the relationship that I think people have had with their company and made them feel often very powerless and maybe they always were, by the way. So maybe this is just a harsh awakening, but I think it's a really interesting thing to think about now. Well, what agency do you have in this and where else would you go? What else would you do? What could you do and still journey in tech if you're not liking where you were, and so it's been good to dig into, well, what's really interesting about these two different dimensions you're taking.

Alexis: 39:26

We talked in my burnout episode and there's three components of burnout. One of them is a lack of agency. So the choice, the feeling like you have a choice the reality is, you cannot control all of the things but the sense and the belief that you do have a choice and that you can you know direct where you're going with things.

Alana: 39:48

Yeah.

Alexis: 39:49

Yeah. The second one is community Having a place that you belong, having people. So even if things are terrible at work, that there's at least someone that you can go commiserate with. That counts. Like you have your tribe, you have your people that you can be with. The third one is actually overwork and overwhelm, because as you get more and more depleted, you actually have to work harder and harder and you sort of fall into this pit of despair. I do think that a lot of what people are reporting in tech really ultimately speaks to burnout, and you're actually addressing two out of the three pillars of what comprises burnout. You may not have meant to specifically address it from that standpoint, but it actually aligns very well.

Alana: 40:41

Yeah, and I think that the real thing about burnout usually is that it's not necessarily the hours that you work. It's the feeling of excitement of what you're working on and that you're in it and you're part of it and you get it and you believe in it. And I think tech really benefited from having everyone in that belief system for so long.

Alexis: 41:11

Oh, totally, it's a virtuous cycle. Actually, your products are better. You wind up doing, I mean, like Gmail didn't exist, except that people were like, no, we have to do this! No one assigned it to them.

Alana: 41:23

Google News is another one Like oh, we should have done that better. I'll just do it on my weekend, right? So I think that that's really been degrading and, honestly, everything that these CEOs are doing is a little bit misplaced to try to get that back, but that's a whole other episode.

Alexis: 41:45

Cool. I'm very, very excited to read more of what you have to say here. I mean, I think the other thing here too is as a parent I have seen some of the more negative impacts of tech. Like I think about the book, Jonathan Haight? I don't know how you say his name, do you know the book The Anxious Generation, How the Great Rewiring of Childhood is Causing an Epidemic of Mental Illness, it's basically speaking to the presence of mobile phones and social media and how much time children are spending on this. The rates of anxiety have skyrocketed in children since that became a common thing. We are starting to see and come to grips and actually make realizations of some of these negative impacts.

Alexis: 42:39

It's not like anyone set out to say, I'm going to launch these things and destroy our children. That was never the plan, but it got used and adopted in ways that were .,

Alana: 42:54

Right, right. And I do write about how tech then was slow to accept that unintended consequences they are in fact responsible for, and that has degraded trust in the industry. Teenagers, when surveyed, have very low trust in tech companies. So they are self-aware, maybe more self-aware than the adults.

Alexis: 43:17

Probably more self-aware, because this is what they know.

Alana: 43:21

But I think it's interesting to think about. If you've got generations now growing up with it and they're skeptical, what is that going to mean for the future? I think there's some interesting things that we'll see play out over the next few decades.

Alexis: 43:36

Yeah, very interesting. All right.

Alexis: 43:39

So another thing I'd like to touch upon here. Throughout the podcast, I am exploring this idea of power moves. So these are past actions that you took that wound up changing your trajectory. Somehow they have to be in the past, because you're making different decisions and moves all the time. You never know which ones are actually going to be the most meaningful or impactful. Can you think of any power moves that have made a big difference in your life or career?

Alana: 44:08

Well, the one that I thought of right away was when I made my first big pivot at Google. So I had organically grown for about the first 10 years at Google, first on the front lines of being essentially a customer service rep for our ads product, but pretty early on taking on a project around documenting ads policy which turned into a full-time role creating, implementing and maintaining policies for ads and other products, and I organically started to become a manager and ultimately got supported for the director promo for that organization. But I had essentially sort of stuck with the same thing, riding the initial rocket ship and taking it about as far as I could before my first intentional okay, what's next? And I think the power move in it was feeling that okay, I've done this 10 years in this function in this team, but I'm going to look elsewhere and I'm going to market my skills from that as general strong skills, meaning like I'm not going to look for another job in policy. I'm not going to go to something highly correlated like legal necessarily. I'm going to say this job was decision making boot camp.

Alana: 45:47

I ran internal teams that supported all kinds of escalations and questions. I was involved in product development and worked closely with engineering and highly cross-functional teams and negotiations right. So I took the core of that and remarketed it and landed an internal role elsewhere at Google in a totally new product we were doing Google Fiber and essentially a somewhat different function, although it was still operations. I was going to run customer support and installs in home installations, so direct with consumers for Google Fiber. Now there were parts of that that were a ginormous leap and benefited from my tenure at Google, my great reputation within Google and the fact that I knew internal systems very well and that was partially something that they wanted to see. But the fact that I had the confidence to remarket myself, that I had the confidence to figure out how to describe my skills, that I just kind of did my own independent research, figured out what was wrong with the ISP customer service industry and walked in with a strategy right Like.

Alana: 47:08

I think there were things in that that I really had to learn along the way in those first 10 years about marketing my skills and about having the confidence. And I will say that I think there was a little bit of effort sprinkled in where I wasn't going to go back to the other role for sure for various reasons, and I'd already been at Google 10 years. So if it didn't work out, where I wasn't going to go back to the other role for sure for various reasons, and I'd already been at Google 10 years. So if it didn't work out, if I couldn't find anything else, okay fine, maybe that was the end of my Google journey.

Alana: 47:39

I wasn't not stressed out about it. I was somewhat stressed out. I was going to come back for my second maternity leave and maybe I wasn't going to have a job. But I think that little sprinkle of like well, let's see, worst thing that can happen is it doesn't work out and I'm looking for a job in the open market, right Like I think that that helped me. Just take risks, throw myself out there and see what happened. And yeah, I think that's the first one I thought of. Just like, go out there and tell the story you want and they'll take you or they don't.

Alexis: 48:14

Out of curiosity, how long was the process? So, like once, you decided I don't want to go back. Though was it just while you were out on leave that you were working through this, or was this a period of a more elongated period that you went through?

Alana: 48:24

I mean you could answer it different ways, because the the job search like from starting the job search to starting the job was only a couple months, so that part was pretty rapid. But for probably about two years I'd been starting to sense like, oh, maybe I'm getting towards the end of this journey. And then I got reorg'd into an organization that then ended up really convincing me. It was time to go the way. Organizations, oh sure. And right before I was going to go out on maternity leave, my then manager, in a very sort of Machiavellian way, revealed his master plan, and it was about ripping apart my team, regardless of what I thought or said or anything. And I was like, okay, I mean like I was upset. Sure, I was also super pregnant and hormonal. So thanks for waiting until I was like you were.

Alexis: 49:22

You were going to be out for a while anyway. What control do you have over that?

Alana: 49:27

Eight and a half months pregnant to reveal your master plan.

Alana: 49:30

Yeah, I was going to be out and and I I basically had to march back to my managers and be like prepare, because I'm out, right.

Alana: 49:37

Um. So the whole thing wasn't great, but I think that it I had been warming up to the idea, to the fact that, like I was probably getting towards the tail end of my energy and interest, like I was probably getting towards the tail end of my energy and interest, and then there was a forcing function, and the forcing function helped me get my ducks in a row and figure out what was next, in a way that if there hadn't been, if it had all been nice and everyone was supportive, you know, like maybe I would have dragged it out, or not even knowingly, but just like I would have had the energy to keep going, even if it wasn't sparking me quite as much. So in the end, I think it all came together as it should, but there were definitely some like bad things that forced it and then meant that I mentally was like great, I'm going to have the baby and then, around three months into my maturity, to leave, I have to start looking for a job.

Alexis: 50:30

It's funny I love the story that you're describing here when I think back to especially at Google the two biggest changes that I made. So one of them was I moved out of my immediate team. It wound up being to a supporting function. So instead of doing client-facing work, I wound up training the people to do the client-facing work. So I moved into the related learning organization, but ultimately, the decision of me quitting last year both of them were ideas that I had been toying with for some time and then there was a forcing function that actually was like oh, okay, it's time. And so I think what you described there I relate very much to it and I have a feeling that many of our listeners. It usually doesn't happen overnight, although sometimes it does. Sometimes you also. You get laid off and, all right, what am I gonna do?

Alana: 51:24

I will say, though, I do think that and one of the things people don't maybe talk enough about, although I'm starting to see it talked about a little bit more is that there is an emotional arc to acceptance.

Alana: 51:36

And if you get laid off while the forcing function happened overnight, your like grief about it, your acceptance about it, your ability to like harness your logical mind and figure out a plan can take a little time. And I think often people feel I've seen like people feel bad that six months later they're still looking or they're emotionally still in shock and denial. And while I think it, you should move through your change curve and if you're not, maybe you need a little help or support or someone to talk to to like help you through it. I do think sometimes it takes time and it's also not linear.

Alana: 52:19

You could like be totally fine. And then you see some announcement your company makes and you're like back in the rage.

Alexis: 52:26

Or or you're bawling, suddenly you're like curled over on the side of the road, like ah, I mean. Yeah, I'm saying this from personal experience.

Alana: 52:35

Absolutely so, I think. No matter what, there's a little bit of a journey to it and it's not usually overnight, Unless you truly are someone who tends to make those kind of snap. You just get an inspiration and you make those snap decisions. But that varies.

Alexis: 52:54

One other comment too many people who have been impacted by layoffs have commented on LinkedIn, but I also have friends who have also said it was the best possible thing that happened to me. I was unhappy in my job and, yes, it was a forcing function. It was hard, but it ripped the Band-Aid off for me. I needed to make a change anyway and I would never wish a layoff upon anyone. I have been laid off much earlier in my own career. It took me many, many years to be comfortable and confident in a job again. I'm not meaning to diminish the feelings of it.

Alana: 53:28

No, no, no no no.

Alexis: 53:29

But I also do think that there can be a silver lining.

Alana: 53:33

If there's anything that I think has helped me mentally grok what happens here, it's comparing your relationship with your company to a relationship oh, totally Right Like if you have a bad boyfriend and they finally break up with you, you're like, oh, ok.

Alana: 53:50

I mean I'm so sorry. Yes, let's go.

Alexis: 53:53

I had codependency issues with work. Work gave me purpose. Work gave me a reason to be here. The problem is I stopped having my own purpose and it was literally, I had to reclaim myself my value, and it changed my relationship with work dramatically. I think so many people are addicted to the value that they are able to derive out of a job.

Alana: 54:20

Oh, absolutely.

Alexis: 54:21

The attaboy kind of stuff.

Alana: 54:23

Yeah, who are you without it? But also, are you accepting things that you should not right? Are you accepting a really unhealthy dynamic because you think that that's what you have to do and then you're just grateful when they fire you and give you severance because you're like great Right. So it's just like a really interesting place. And the minute I sort of accepted Google as the bad boyfriend that I was choosing for very specific reasons to stay, I think it helped me get that appropriate distance and I find that people stay in a zone where they're in the relationship with the boyfriend but angry at the boyfriend all the time for a very long time, and I think that's a little. That's something to puzzle through.

Alexis: 55:14

So I want to share a power move for me that is quite unrelated to all of this, but I think especially - this is a women in tech episode. I took a public speaking class that changed my life. I know it sounds ridiculous. Let me describe what happened. I went to this class I actually am, I mean, I've spent years on stages and so, like I'm a, I'm a good presenter. The issue was a body language issue. I tilted my head and I fussed with my hair and my face. And guess what those are? Those are flirtatious signs and so, basically, even though I had great things to say and I commanded respect with my voice, I was doing these other things that made me get perceived in yucky ways. And what happened - this was over 15 years ago. This was before I was even at Google.

Alexis: 56:10

I took this class and the following Monday I showed up back at work and I had to deliver some really tough feedback to a senior executive. It was when I was at Accenture, so I was a consultant. Basically, we had to delay the project. Who the hell wants that? And it's going to cost them more money. So, like yuck, no one wants to hear this stuff. But so here's the deal. I was trained to hold my chin, between my forefinger and my thumb.

Alexis: 56:36

I'm showing Alana here. I can't show you listeners, but I practiced in front of a mirror, literally not moving my face, and even as I hold this you can see. Anyway, but I practiced in the mirror, not holding my face. It was so awkward. But basically in this meeting I held my head straight and I didn't move and it felt very robotic. And after this meeting I had like seven people come up to me and say, wow, that was awesome, like really great job in delivering that. I know that was hard for you to do. I had never in my entire career had I don't even think like one person come up to me, let alone a handful of them. The other thing that happened after this is I was never again sexually harassed and I was never again hit on by a married man.

Alexis: 57:29

It is so huge body language. I want to do an episode on this. I actually need to find someone to dig into this. I think it is this thing that, even though I had all these skills, I was being perceived in a way that was not helpful to me and was holding me back and, seriously, it changed my trajectory in so many different areas of my life.

Alana: 57:56

I love that. I will say that I often tell people that the most horrible, worst class to take is public speaking, and it is absolutely the best class to take, and the reason that it's the worst is that they will record you.

Alexis: 58:10

Oh yeah, you have to watch yourself and it's like oh.

Alana: 58:14

You will have to sit there and watch yourself, or you'll be doing it in front of a bunch of people and they will like clap every time you say um, or every time you tilt your head or whatever it is. So it is the worst. But then you will learn things for the rest of your career, both when you're just one on one or in small groups, but also the public speaking stuff. I just it is huge. Yes, it is, but horrible. But just take the hit.

Alexis: 58:42

It's so uncomfortable and it's worth it. I mean it's it's totally worth it.

Alana: 58:48

If you are at a company that regularly offers these classes and you can get them for free, take it.

Alexis: 58:52

That was, that was why I did it so

Alana: 58:54

Yeah, just take it.

Alana: 58:55

Just take it. Have the terrible few days.

Alexis: 59:01

Mine was one day. That was all it. One day and two awful recordings.

Alana: 59:07

Mine was maybe a couple days, but probably not full days, and what I was going to say about it that really helped me was that when I get up in front of a crowd I have a lot of nervous energy that I thought people could see, because I literally shake, not like a huge shake, but like jitter. So in my head people could see because I literally shake, not like a huge shake, but like jitter, so in my head people could see that and I talked about it as something that made me nervous. And then people were like, oh, we can't see it and I was like, oh, it's not actually noticeable to the other people.

Alana: 59:41

It's not noticeable, and so the rest of my career. I've accepted my jitter and it doesn't make me nervous because I mean, listen, maybe some people can see it honestly, but I don't know.

Alexis: 59:49

All right. Last question for you today.

Alexis: 59:52

Let's say someone comes up to you and says Alana, I want to be a woman in tech and I want to stick it out for 25 years or more, just like you. What should I do? What's the advice?

Alana: 1:00:04

What should you do? What should you do? I think there's an interesting combination of patience and agency that I think you are going to have to figure out, because if you want a long career in tech, you are going to have amazing days, you're going to have bad days. You're going to be on teams that you feel a lot of alignment with and teams you feel almost none. You're going to be in situations where you are learning a ton and situations where that seems to dry up and you're going to be told you're valuable, and then you're going to get reorged and somehow same exact stuff you're going to be told isn't valuable. So there is going to be a lot of years in time and exercising some amount of patience. A bit of this, too, shall pass. A bit of noticing the patterns and being patient with them, knowing that when you get a new boss you're gonna have to do some retraining, yada, yada. But at the same time, balancing that out with a sense of agency.

Alana: 1:01:17

I started to give a lot of folks is set a timeline, right, if you notice that something isn't great, think about a couple things.

Alana: 1:01:26

You can try to change that and set a timeline. I'm going to try these X things and if that doesn't work, in six months I'm going to decide what to do next. If you can do that, I think it'll both give you the patience to get over some hurdles so that you continue, you don't overreact, you don't get disengaged too early, you don't start distracting yourself and looking for a job when really all you need to do is double down and get through this period. It'll get you over some of those humps but at the same time it won't make you too patient, it won't make you complacent, it won't make you accept things for the long run that you shouldn't in your career, because you've given yourself a timeline and you can go back to it.

Alana: 1:02:14

So endurance, I think, is going to be the name of the game, of that right. Like, how are you going to endure through some of the bad times but also take advantage of the great times, right, hurdle through them, enjoy them, love them, but have a plan B when times get rough. I think that's the .

Alexis: 1:02:34

I love that. Endurance. That is such a great word for it.

Alexis: 1:02:39

If I had to give advice, I think it is make a decision about what it is that you want, and the caveat is it's okay for you to change your mind at any point. You know, I like what you're talking about, though, because I do think that I myself, especially when I was younger I remember my parents used to, they used to call me fickle and like, especially my first five years out of college, I had five jobs in five years. This was not by choice, this was... I graduated right after the dot-com bust and I moved to New York right before 9-11. Like everything was just wild and crazy. I was just trying to survive. But I also remember they used to talk about like me being very fickle and just jumping to the next thing..

Alexis: 1:03:28

I like what you're talking about of having endurance and giving something enough time so that you're not just being flippant because like, oh, this dude said something that really pissed me off. I'm done. It's like yeah, they said something. What can I do about it? Let's try some things. Do I even need to listen to them? Or should I maybe say something back like hi, that was a jackass thing you just told me and guess what? It didn't feel very good. Can you not do that anymore? Or change Like?

Alexis: 1:03:55

There's all sorts of things that you could do just out of that one interaction, let alone everything that goes on over the course of a day or a week or a month in your work. But when I think about especially, make a decision and go after it, what's your plan? Come up with a plan, be flexible, both in terms of your own decisions but also the things that are changing around you. You might get offered a new position or, ooh, a manager role opens up. Do I want that, Do I not? By the way, both of those are fair decisions. Neither one of them is good nor bad. And then stick it out. Perhaps six months is like a good place to start with, or three months, you know just some period of time. So you're giving it space.

Alana: 1:04:36

It's completely your thing and it's going to vary, right, because some things are knowable quite quickly and some things take longer to work out, right, like at Google, the promotion cycle was every six months, so to really know if you're on the path towards what you want, sometimes it's a little bit longer. So, yeah, I think you set the time Again. You have the agency for what. You will be patient for, you will tolerate whatnot, but I think being too reactionary sometimes cuts off opportunity. I think we've seen lots of times where you just got to get through a little bit of a hurdle and then that manager would have given you a 2x larger team, right? And so I've had people look back and be like, oh, I should have, I should have tried X, I should have tried Y, and so I think this gives you a happy medium on both.

Alexis: 1:05:26

Yeah, I like that. Well, this has been a fantastic discussion today. Thank you so much for being here, Alana, on behalf of our listeners as well as me, because this has just been delightful to have this conversation. Thank you.

Alana: 1:05:41

Thank you for having me.

Alexis: 1:05:42

Before we close out our episode today for our listeners, I would like to invite you to get in touch with me. You can text me any reactions or advice or suggestions that you have for this episode or the show. You can find this in my show notes. I'd love to hear from you.

Alexis: 1:05:59

If you have enjoyed what you've heard also, please subscribe to the show, Leave a comment. It's a small thing, but it means so much to me and a world of difference for the show. As always, I will share links to notable reference in the show notes and I'll give a couple links for Alana. I mentioned a few earlier that I really love that interview you did with Cheryl that was great. But Alana's website, alanakaren. com. I'll send a link to where you can sign up for her newsletter and also her book, because it's awesome, and with that, all of our listeners. I wish you a very fond well and I hope you have an awesome day. Thanks..