When we last spoke with Keshav Puttaswamy, he told us about spending 20 years at Microsoft, finally making the break for a new venture in Australia and ultimately coming back home again. Hitting the 25 year mark with Microsoft and watching his own daughter set off on a new adventure, the time seemed to be right to make a leap again. In this Roads Taken Revisited, find out how being open and staying in the present can provide options for the future.
When we last spoke with Keshav Puttaswamy, he told us about spending 20 years at Microsoft, finally making the break for a new venture in Australia and ultimately coming back home again. In this Roads Taken Revisited, Keshav talks about the five years that passed at Microsoft since his return from Australia and how the coincidence of 25 years at one company and his daughter’s prep for her college career jumpstarted a new venture for him.
In this episode, find out from Keshav how being open and staying in the present can provide options for the future…on Roads Taken with Leslie Jennings Rowley.
About This Episode’s Guest
Keshav Puttaswamy, a Seattle-based product manager, recently hit his 25th work anniversary at Microsoft and took it as an opportunity to take a chance on a new experience. His new chapter has begun with a leap to the Foundations team at Meta where he will weave his product management experience into something new and far-reaching. Check out the picture from his going-away party at Microsoft, complete with cupcakes with his face on them.
For Keshav’s first appearance on Roads Taken, listen to Time Traveler.
Keshav Puttaswamy: My older daughter is about to embark on her college adventure, and yes, I'm 25, 30 years into my career, but I shouldn't get comfortable here. I should kind of pace my daughter in some ways and say, Hey, why don't I jump in a little bit into that deep end? And how can I create that sense of excitement for myself?
Leslie Jennings Rowley: When we last spoke with Kesha Puttaswamy, he told us about spending 20 years at Microsoft, finally making the break for a new venture in Australia and ultimately coming back home again. Hitting the 25 year mark with Microsoft and watching his own daughter set off on a new adventure, the time seemed to be right to make a leap again. Find out how being open and staying in the present can provide options for the future on today's Roads Taken Redux with me, Leslie Jennings Rowley.
Today I'm here with my friend Keshav Puttaswamy and we are in a special edition of Roads Taken Revisited, taking a seat with one of our past guests who was so kind to take us down the road from our graduation in college to where they were at that moment. And that moment was a little while ago, so we're taking another deep dive into a shorter period of time and we'll see where the shorter part of that road has taken us. So Keshav, thanks so much for being here.
KP: Thank you, Leslie. It's always fun catching up and listening to all the stories from our classmates as well. So I'm really excited to keep this going.
LJR: Right. So, the last time we spoke, I asked you those very big questions of when we were in college, who you were, who you thought you'd become. We got to travel down nearly 30 years of that pathway, and we kind of left you having been all around the world after a very long time in one place. And those travels ultimately led you right back to that place. So, let me have you fill us in. You had been at Microsoft for all those years. You had a great adventure in Australia. You came back to Microsoft with kind of that storyline of we think we can never go home again, but you were able to do it.
KP: Mm hmm.
LJR: You were embarking on that second journey in the same place when we last spoke. So what was that like and where has that taken you?
KP: Yeah, so the second stint, the first stint was 20 years before I left for Sydney, Australia. And then I came back after about two and a half years. So now I'm, actually, yesterday was my last day after another five year stint at Microsoft. So a total of 25 years. So it was, it was really a sort of a poignant moment where the team, literally on my last day, got together and did balloons and it was like a 25th work anniversary. It was an emotional moment for me just because of how much time I've spent there. But, you know, it does in many ways…you know, when you spend 25 years in a place, it has a special kind of significance and it is kind of home in some ways. And, you know, even as I leave, folks at Microsoft are like, you know, you might come back at some point. Like once a boomerang, always a boomerang. But yeah, no, I think, you know, it was a wonderful five years. I got to be part of kind of a new phase for the company. A lot of transformation and I was working more internally the last 5 years as opposed to the rest of my career. These 5 years were all about helping our Microsoft employees get more productive and sort of help them balance their lives better and, you know, work through. And we went through a lot. We went through in the last five years, some heady growth initially as a company, but then the pandemic and everyone went remote. So we kind of had to figure out how does this all work? How do we continue to stay productive? And then we were in this kind of interesting phase where it's hybrid and people are trying to figure out, should I come into the office? And why should I come? Was it worth it? And it's like a whole set of things. And now in the last year, it's been all about AI. And, you know, are we all gonna lose our jobs? Or, you know, what is it going to do? And it creates a ton of opportunities. It's been a fun ride.
LJR: Yeah, so I do love that your colleagues recognized once a boomerang, always a boomerang. And we can never say you can't go home again. But did there feel with those balloons and everything, like there was a different kind of finality? Or at least like in the chapter, or do you really kind of think, Oh, it's possible that that could be another place I end up or a place I end up again?
KP: Well, I've learned after all this time to never rule anything out. I'm always open to wherever the road takes, I guess, so, uh, you know, I have a lot of friends and I'm certainly not with coming, leaving with the intention to come back by any means. I think, you know, I've had a great chapter there and I'm ready to take on the next step, but you know, it's interesting. I think I had a much harder time the first time I left, because it was 20 years, and I literally hadn't worked in any other company, so it was a very daunting. Well, also we were moving continents, and you know, that was also kind of a part of it. But at that time it felt like, oh my god, I'm making this big change. Now, I…It didn't feel quite as huge. I mean, it was a big milestone, 25 years, but, you know, at the same time, I'm not moving. I'm staying where I am. My family, their lives are literally, they wouldn't even know any different. Like I, I'm just going to go work at a different company as opposed to the one I was. So for the most part, it'll just be me and what I go through. And so it wasn't a hard, as hard for me, even though it was emotional in a different sense.
LJR: Yeah. Yeah. Okay. So there you are, you're going to stay in Seattle. So what is the next move career wise?
KP: So I'm gonna join Meta. AKA Facebook.
LJR: I've heard of it.
KP: Yeah, exactly. I will be working, I continue in the discipline I'm in, which is product management. I'll be working on What's referred to as the foundations team for the family of apps. So the family of apps are the four big apps that we all know, Facebook, Instagram, WhatsApp, and Messenger. And our team works on sort of a horizontal layer—if you think about it—just a foundational element that can be part of every one of these apps. There's a lot of similar things in these apps. They all have video, they all have messaging, they all have voice calling, you know, those kinds of things. And trying to get more efficient and be better at doing those things and allow for each of the apps also to then focus on what's unique about them.
LJR: That sounds like a great—I mean, of course, this is probably why you said, yeah, I'll do this--marriage of past skills, past, expertise that you've gained over all of those 25 years, or 30, really, with your other experiences, and yet in a new environment that is so well known and ubiquitous, really, to many of our lives. And so the day to day is going to feel similar but new, and I'm sure that's exciting. But does that afford you also any new insights into, like, what the big arc of the next chapter might look like? Is it, I'm doing something that I feel kind of comfortable in because I want to be shifting energies elsewhere, not just career? Or is it I'm looking at something new, like this new environment, because I want that career thing to be kind of, the thing I'm really putting my thoughts and energies into? Where are you in the big arc?
KP: I think it's you know, I'm definitely thinking about my career and I feel like, you know, after a reunion, I mean, the time has kind of flown by, it's pretty crazy. And as I look at sort of up ahead, you know, I don't want to say it in a negative way, but we don't have that much time more, you know, and things keep moving. In fact, my older daughter is about to embark on her college adventure. So she's a senior in high school and she finally has decided where she's going and it's all very exciting. But when I think about it, you know, this was literally how I processed this: When we all got into college, I mean, and we were looking at the four years ahead, it was a big deal. And there was so much excitement and newness. And, you know, then we went out and made new friends. And, you know, it was such an incredible experience. And we came out of it four years later very different. There's a whole transformation that happened in those four years and so much can happen in four years and I'm expecting with my daughter it's going to be the same thing and I sort of had to challenge myself and say, Hey, yes, I'm 25, 30 years into my career, but I shouldn't sort of get comfortable here. I should actually see if I can kind of pace my daughter in some ways and say Hey why don't I jump in a little bit into that deep end and take that same kind of journey? How can I create that sense of excitement for myself? What would it take to have that sense of entirely new learnings? completely different experience ? And I think Meta is going to be very, very different from Microsoft. Yes, big company. I'm hoping I can apply many of the skills that I have developed. But I also know that it's a very different culture. I think the problem space is very different. The scale at which Meta operates…As big a scale as Microsoft operates, Meta is like, you know, in the foundation team, like I was talking to one of the, um, uh, the leaders in, in the foundation team and he used to work interesting. He was ex-Microsoft as well. And he worked on Windows and he would say, well, in Windows, I would go in and say, Oh, I'm going to work on some. piece of code that is going to touch maybe a billion users. And he thought that was mind blowing. And then he comes to Meta and now he's like, I developed this video platform that is literally used by 3 billion users a day. It's insane. It's like almost everyone on the planet that has internet connectivity. So it's mind boggling.
LJR: It’s amazing. Right, right. Well, that's a point onto itself. But going back a tiny bit where you were saying kind of. This is a chance for you to be in step with your daughter who's at that threshold moment of what promise the next few four years holds and then beyond that. I love that. And it harkens back to our first conversation where you said that you'd gotten advice from someone who told you if you want to remember something, make a change. [KP: Yeah.] Because often when we continue to do the same, all of it runs together. And these Moments punctuated by something new kind of wake us up again, right? And so that's the, that's the feeling that you want to get.
KP: Yeah, I think that those thoughts went through my mind as well. I think it's very true. When I think about my first 20 years of Microsoft, it is a bit of a blur. And then those two and a half years in Australia just pop out. When I came back, I was starting to get into rhythm and it was five years and before you know, I blinked and it was gone. And so yeah, I want to cheat a little bit and recreate, you know, I want to slow down time in a, in a weird way and see if this will help me kind of really remember what's going on and just be really connected with everything that's going on. And I, I do, do believe that it is a bit of a hack, but change really slows time down in an interesting way.
LJR: I think that's the first time that the words slow down. And anything to do with Meta have ever been put together. So it does not seem like the place that you'll be able to slow down. But maybe, I don't know. It's a hack, as you said.
KP: Not, not slow down like the intensity or what I'm doing, but slow down in a way that of my perception of time really is what it is.
LJR: Right, right. So, that said, you have been going through things in the last few years and now will be, you know, having your plate full with just a new complement of things. Does that afford time for cricket and all the other things and travel? And are you still keeping a pace with your numbers of countries?
KP: No, I have not, unfortunately. And I have not. I haven't done anything more on the cricket front, although all my friends, there are a few of my colleagues who are still playing and they're like, Hey, we're ready to start an over-50 league. So [LJR: That’s right.] you want to join that's the time I might, you know, consider at least trying it out, you know, as long as they don't like pull a hamstring on the first day or something, uh, I would give it a go. But in terms of travel. I haven't, other than a few trips to the East Coast. You know, I've made more trips to the East Coast than you know, I can remember. Partly, well, it started with the reunion, but then with my daughter, she's going to land up in the East coast. And so we ended up making a few trips there for her. And so I expect I will pick up a little bit of travel because the team that I'll be in is distributed across here in Seattle, California, New York, and London. So I suspect I will end up just from a work perspective. But catching up on the country count, I think is going to be challenging. I don't know how I'm going to do that. I'll have to figure that plan, that part of it out again, because I'm really far behind now.
LJR: I do love that some of the things that you've been thinking about, you've tied to your daughter's journey and, you know, this moment of reinvention. Are there anything else, is there anything else that you kind of have gleaned from this moment where she's been having to figure out who she is in relation to who she might want to be and who makes that fit really nicely in terms of an institution that she's going to? Or just the process of kind of introspection or any of that, has that helped you in any way? Or is it, is it just chance that, that you've had the opportunity to put a close on the Microsoft for now and move on? Or was it really, Oh, I'm seeing something that I want to get in on.
KP: Yeah, it wasn't as planned, to be honest. The opportunity, this particular opportunity just presented itself. It was from somebody I'm, I knew and he said, hey, can we talk? I think there's a role here. We really think you'd be a great fit. And so I wasn't thinking about leaving but so when that conversation started, it got me thinking about you know the parallel because my daughter was also going through that and you know for me it was—as I gave her advice It made me also think, uh, you know, I don't know, there's a story of, Mahatma Gandhi who apparently, I don't know how true this is, but it's been told that this mom took her son to Mahatma, they walked like three days from a village all the way to where he was and there was a line outside his house and then they finally got in front of him and the mom asked Mahatma Gandhi to tell her son to stop eating sugar. And Mahatma Gandhi said, well, um, Come back in two weeks. And so, she was a little bit perplexed and walked all the way back to her village. And two weeks later, she made the trek back and finally got in line and came back up in front of him and, and said, Can you please tell my son to stop eating sugar? And,Mahatma Gandhi said, stop eating sugar. And, and so she was like, well, why did you make me walk all this, you know, back and forth?
It was not easy. He's like, well, you know, If I were going to tell him to stop eating sugar, I needed to stop eating sugar myself. So it was that kind of same moment, like if I'm going to give my daughter advice about, hey, you know, you should be open to change and try as many things as you can when you're in college, this is your opportunity. You know, she's going to liberal arts college and she's going to have this opportunity to explore lots of things. You know, I was thinking to myself, well, So, how much have I explored and really tried new things myself and, and, you know, perhaps I should do the same and try this out. It's, it's not, you know, super crazy. I know people have completely switched careers and going to law school or doing, done crazy things like that. I am not, I'm not trying to do anything that…but still in my own world, it definitely pushes me to try something that is you know, uncomfortable and probably, you know, you could say it's a bit risky. I’m well settled at Microsoft and it's going to be a new world. And I think that that part of it, which is, hey, change can be good. You learn a lot about yourself, you know, try new things and, and you'll come out of it. You don't know what you're going to learn, but it's going to be good. We'll, we'll both get through it. And so that's part of what was going in the back of my mind. I felt like I needed to push myself out of my comfort zone. And, um, this definitely hit that sweet spot. Nothing excessively crazy, but still well out of my comfort zone.
LJR: Yeah. Yeah. That is, that's sage advice. You don't know what you're going to learn and you have to be open to it. And you said, you know, earlier, you're open to everything and I can definitely feel that and see that. I will say that is a very odd Gandhi story because I was struck by, that's what you go ask him? Like, really? I'm not sure that's what I would have chosen.
KP: I know. Hey, I didn't, I didn't, you know, I don't know how true it is. It's just been told. It could be, it could be fictional. But it was, it makes a point. Like, don't tell somebody to stop eating sugar if you're eating sugar yourself.
LJR: That's right. That's right. All right. Well, I want to ask, and I don't know how to ask this, particularly since I think I want to start asking all of my revisited people this, so maybe you can help me. You said you're, you're a candidate for the senior league in, cricket here.
KP: Right.
LJR: So we are getting to a certain Age or place in the life cycle, if that's the nicer way to put it, where we kind of could be considering slowing down or like, I've heard a lot of people say, I have one more in me, like, not two more in me. I have like one more big push. And I think that's the part that we're now feeling more like your daughter, like, Oh, my gosh, what, what is this…What's it going to look like? And how do I make it happen? And I think I know the answer that you will give. But do you think that our next phase is something that we should make happen? Or is it something that we should just deal with when we get there? Do you know what I mean?
KP: I think, I mean, a little bit. I mean, at the end of the day, I also give this advice to my daughter, which is, you know, stay present, spending too much time in the past, will probably make you depressed. And you spend too much time worrying about the future and it will cause anxiety. So staying present. And I think that I would say, see what's in front of you. You know, if this hadn't happened, I would still be appreciating life and enjoying life. Like, it's not like, you know, this change is the thing that I needed, you know, and, and without it, you know, my life wouldn't have meaning or anything like that.
It just worked out at the moment and I just went with it. And I think that I'm more in that mold where I'm, I wasn't trying to make something happen or I mean, it wasn't like, Oh my God, I have to make one big push in my career now. And otherwise I won't have that opportunity for me. It was just like, Hey, What's going on in my life? What do I, when I look around, what, what's around me? And I didn't try super hard to, to try to create this opportunity for myself. It just happened. And the only thing I did was challenge myself to be like, when those opportunities arise, don't choose kind of the comfortable option. Because that's kind of my tendency, you know, well, that'll be like a natural thing to do is like, Hey, 25 years. There's a lot of other benefits. If I stick around for another, you know, there's like this whole at Microsoft, if you retire at 55, scarily enough, you get to keep all your stock and everything. So there's like a extra financial incentive to hang around. But, you know, I said, you know, just break it down and you know, focus on what is the most important. And for me, the most important is that experience. Time is the most valuable commodity we have. And so how do I make sure, how do I, you know, sort of extend that time, that feeling of, you know, living and really exploring and learning, I think, and so that's really what I'm doing. It's not to me. It wasn't very complicated.
LJR: Have you always been the present focused type?
KP: I try to be. It's hard. I think it requires intentionality. I think it's very hard to do it. So I have to keep reminding myself to do that, and just so that I can sleep well, and, you know, enjoy what's around. Because, you know, there's a lot of ups and downs that happen in life, and I found myself the more present I am, the less stress I feel and just happier, you know, in the state of mind. And, and there's times where it's like super hard because you feel like you're stuck or you're down and it's easy to kind of get caught up in it. And you sort of, woe is me and you know, all that kind of stuff. But I just try to remind myself of what I have and, and stay present. And this is what I try to tell my daughter as well, as well as, you know, anyone who ask me for any advice. If there's one thing I would say is, you know, just stay present.
LJR: Well, wise words, sage words, and I hope that we get to follow some of your other presents. So, this probably won't be the last time. Boomerang. What is it? A boomerang is always a boomer.
KP: Once a boomerang, always a boomerang.
LJR: Once a boomerang, always a boomerang. So we might see you on Roads Taken again.
KP: Yeah.
LJR: But I love that we got to catch up and see, where you've been since we last talked. So all the best in your new venture, and your daughter’s as well. And we'll catch up soon.
KP: Awesome. Great chatting, Leslie. Thank you so much.
LJR: That was Keshav Puttaswamy, who recently hit his 25th work anniversary at Microsoft. (Check out the show notes for a link to the picture of his party, complete with cupcakes with his face on them.) His new chapter will begin with a leap to the Foundations team at Meta where he will weave his product management experience into something new and far-reaching. We wish him and his daughter all the best for their next adventures.
We are excited by this new adventure of ours, trying out this redux concept and we wonder what you think of it! Drop us a line through the Contact Us link at RoadsTakenShow.com to let us know or to nominate our next revisited guest. We're looking forward to this season with both new and repeat voices and having you tune in weekly with me, Leslie Jennings Rowley, on Roads Taken.