How To Take a "Gap Year" as an Adult Without Falling Behind with Taskrabbit CEO Ania Smith

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3:14Can you close your eyes for a second and think about what it felt like to be 18? There were probably a lot of feelings. I mean, we all had a lot of feelings at 18. But I want you to remember one in particular, that you could do anything. That you had a sense that you had some commitment coming, whether it was a job or going to college or starting a family, but that maybe you didn't have to start that commitment just yet. that maybe you could take a gap year. You could move to the other side of the world if you wanted to. You could try a weird out there job that you knew you would never want to do for the rest of your life, but you could take a chance.

3:5018 feels like the one time you can step out of the stream of your life without risking forward momentum. But Anya Smith would tell you, with careful planning, you can recreate this moment in your life again without risking a career setback. Anya and her husband, Rob, were both in high-powered jobs. She was at Airbnb. He was at Glassdoor when they decided to take their three kids on a gap year to Argentina. You might think that taking a year off work would have stopped Anya and Rob's careers in their tracks. But he now has a big finance job in Silicon Valley, and she is the CEO of TaskRabbit. So clearly, they are crushing it.

4:29And today, Anya explains how they pulled all of this off. In our conversation, we talk about how she and her husband budgeted and prepped for their gap year, what lessons they learned from taking a step back from their demanding jobs, and the point system they use to make sure their family comes first. And then, of course, Anya and I dive into everything TaskRabbit, including how they're tackling the supply and demand questions that are stumping other gig employers and the oddest jobs that people post on TaskRabbit. Anya Smith, welcome to Money Rehab. Thank you so much for having me. I'm so excited to talk specifically about this gap year that you and your family took.

5:07It was about six years ago, right? In Buenos Aires. At the time, I'm fascinated because you and your husband are both at the height of your careers. Why did you do that? So we had been planning for quite some time. Really, it goes back to when I was pregnant with my youngest son. And I knew then that our lives are going to just about, they were already crazy and they were going to about to get worse. And so I remember having a conversation one day with my husband saying, is this sort of it for the foreseeable future? Or can we start thinking about taking some time off at some point? And then I've always thought that when your youngest one is five, when you're a little bit more free.

5:49And so we started saying, hey, how about five years from now when he's five? Let's see if we can make that work. And then actually, when he turned five, we were not ready. I had only been at Airbnb for a couple of years. My husband had been at Glassdoor for a couple of years, and it just didn't quite seem like the right time, especially for me at Airbnb. But we also knew that there would never be the right time. so we promised ourself that we're going to reevaluate this every year and so a year went by and as it happened there is all sorts of stuff glass door got purchased so there is some possibility of taking a break for my husband and then I thought yes I should wait for four years but then when I wait he starts something it'll never work and so we decided to pull the trigger and say okay we are ready and we've got ourselves together to do it quite quickly but it had been in our minds for quite some time.

6:43And we had been saving money for quite some time in order to make it happen because really it meant no income for a year. And then of course, spending money on top of it and a double whammy. Of course, the cost of living in Argentina was much lower than it was in a Bay Area. I think it still is. Yes. And so you decided to do it quickly, but six years in the making, it sounds like. Your kids were what, six, eight, and 10. How did you even talk to them about the idea of a gap year? Oh, wow. It's such a great question. I remember just being scared. And so we had dinner together every night and my husband and I practiced and said, okay, tonight, we're going to say it.

7:21We didn't want to tell him too early because then we thought it's just going to prolong the pain. But we also wanted them to have some warning and not say, hey, tomorrow we're moving. So probably around April timeframe, we sat down with them and said, hey, hey, this summer we have all this travel planned where we're still going to do the travel, but then we're going to continue that on and we're going to actually not come back for this next school year. It was definitely not an easy conversation, even at their young ages, especially the oldest one was not pleased. And did you tell them how they were going to fill their time?

8:00Did you guys even know how you were going to fill your time? Like how much planning went into this? I'm assuming you said you saved, you made a budget, maybe a family P &L or something like that. Yes, but there was so much planning. It took, I left my job in April and until we left for, we first went to Asia that summer. And so until we left in June, I was working all day, every day on the planning, literally. So it's just takes a lot to take yourself out of your day-to-day life, We knew for them what we wanted to do is make sure that they continue going to school. And it was really important for us to make sure that they learn Spanish.

8:42And so that's really what we focused on is trying to find a school for them. I didn't speak any Spanish. And what I wanted to do is find a school that isn't the expat American school or British school for a couple of reasons. Most of those types of schools are actually located on the outskirts of towns or in the suburbs. and we really wanted to live in the center of Buenos Aires. And then secondly, many of those schools teach in English and our whole goal was to ensure that our kids learned Spanish. And so that meant getting some help and getting some friends to make phone calls for us and interview schools and try to do this long distance until we had a chance to get down to ourselves.

9:26So we knew that kids would be going to school And then we started thinking a lot about what we were going to do with our time. So first and foremost, we're going to spend a lot more time with our kids, right? They would be down to school at three or something. So that meant that we still had some time in the morning and midday to give ourselves back. And so we started thinking about what are we going to do? Like which hobbies we're going to pursue? And what are we going to do with our time? And that was really fun. What'd you do? So we both did different types of things. We studied Spanish. We did that for a couple of hours every morning.

10:00And then we went and did long workouts every day. And then we had long lunches every day, which is really nice. And then in the afternoons, we spent a lot of time really trying to learn new hobbies. So we danced. I went horseback riding a ton. My husband learned how to drum. I took a photography class. So we did lots of those types of things. We also, actually, I was just talking about this to someone today. it's really hard when you're generally quite ambitious which both of us are to let go so this concept for example seeing a movie in a movie theater at 11 a.m on a Tuesday it was really hard to say that's okay that we will go back and work again that we have to give ourselves the space to relax as well and really think about what we want to do with our the rest of our lives where do we want to live?

10:52What types of careers do we want to pursue? Do we want to keep working in tech or not? And what is that going to look like? And so we spent a lot of time focused on that. Yeah, the planning alone, it sounds like the type A ambitious you like really snapped into high gear for this. It sounds like even that part was exhausting, even though it was supposed to be a relaxing experience. It took some lead up. And also, I'm assuming you guys had a lot of discussions about being able to find an on-ramp again when you did decide to rejoin the workforce at such high levels that you guys were at. That's right.

11:29And that spring before we left, I was just focused on making sure we find renters for our house, making sure we can pack up, making sure we can sell our cars, all of those types of things, speaking with the school so that they could give us some guidance as to what our kids should be learning the next year, because we knew that we would pull them out for a year and then they'd come back and not go back a year. They would keep going. And so what did that mean? So it was a lot of planning, but it was exciting as well. And then we promised ourselves that for the first six to eight months, we're really not going to focus onto what's next.

12:04We're gonna first decompress and relax and focus on ourselves really and our family. And we won't start working on what's next until the spring. And we stayed pretty true to that, I would say. And you, it sounds like you saved, you had a budget. How detailed was like a P &L or a financial plan? And did this gap year change the way you guys looked at money? Certainly it changed. When you have no income, we don't have infinite funding in any case. So we had to be quite strict. So yeah, we knew how much we would spend, obviously, on rent and food. And then our expenses after that were quite low because we have car payments or many other things.

12:46We were making some money on the rent from our house in Marin. And so that also helped to set up or helped to offset some of the costs. And then we knew that we would want to travel quite extensively. Obviously, winter in Argentina is the opposite timing. And so therefore, summer is the opposite timing. So we knew middle of the year around Christmas time, we're going to have some time to take off. And we really wanted to travel in Patagonia. And that's just expensive, whether you come from here or from there or really anywhere. The cost of a hotel room is the same. Yeah. Yeah. And I think one of the most valuable skills that any executive or CEO can have is this ability to adapt to change really quickly.

13:29It sounds like this gap year was a crash course than that. Of course. And we really wanted our kids to be able to do that. It's really hard to show up at a new school with all new friends, with a totally different layout, different ways of learning. And then most importantly, not knowing the language. It forces you to really try to figure out how to navigate that. And for us, it was really important that it helped our kids to build independence and to build resilience. I think resilience in particular is really important to grasp that skill quite early on and continue to push yourself into new learnings and new territories and honestly to feel uncomfortable because that is the easiest way to learn.

14:13And so it was important for me to give my kids the opportunity to take them out of their comfort zone in Marin and their kind of very nice life and somewhat of a bubble and make them figure out how to navigate something totally new and different. It's super cool that you did that. And as the year came to a close, it sounds like for the first six months, you didn't do any thinking about what's next. And then what happened? You guys thought maybe you would move back to Park City or even South Dakota. Fascinating choice. You ended up back in the I grew up in South Dakota. So then that was easy to think about.

14:49We had a lot of conversations. And when you think about it, we had a lot of time, right? We would take, drop off our kids at school sometimes and then just say, okay, let's skip the Spanish lessons today. And they're working out, but let's go and have a really long breakfast through lunch and just talk about different options and what we want our lives to be. And it's really nice to have that space because normally, especially when you have kids, you're just constantly busy. And honestly, at least for me, I'm just trying to survive. There's a lot going on when you have a two, four and a six year old, especially trying to still maintain a career outside the home for both of us.

15:27And it was really nice to have the space. And we wanted to let ourselves know that, hey, maybe and this is obviously pre pandemic and the way we work has really shifted, obviously, in the last four years. Before then, most of us couldn't quite imagine where we would be today. and we spend a lot of time talking about what would it be like if we left the bay area and moved to a small town what would we like what wouldn't we like what do we want out of our lives what do we want for the next decade where our kids are still at home how present do we want to be what do we want out of our careers what will we want after the kids leave and so there's just a lot of questions and meandering and letting things simmer and then talking again and again And then to the point where I started interviewing, as did my husband in different parts of the country, even while we were still living in Argentina.

16:23So I flew out to Washington, D.C. I used to live there and really love that area and thought maybe it's time to move back to the East Coast. And then after all of that, it became fairly clear to us that, no, we actually still want to stay in tech. And this is why and this is the impact that we want to have. And this is what we want to do. And so that clarity and knowing that we're making that decision in a very deliberate way was really freeing. Oftentimes, figuring out what you don't want to do is just as important as figuring out what you do want to do. And so getting back to that choice sounds like it wasn't an easy one.

17:01It took a lot of discussions. How did you ultimately get the job as CEO? Was it toward the end of your gap time? No. So I first came back and started working at Uber. So I looked at many different opportunities in the Bay Area, and I obviously had already made some connections prior to my departure. And so I started having long conversations. I flew up a couple of times, and I really believed in what Uber was doing, particularly on the EAT side. It was very complementary to my skill set, and I really loved the team. And I was very excited about the new opportunity at Uber. And then did TaskRabbit reach out to you directly?

17:39did an executive search firm? Like, how did it work? Sometimes I think people think getting a job as a CEO is confusing black box. It can be. And I think there is no one path. I think that there's multiple different ways. It also depends on what the company is, the size of the company, all the things. But for me, and in my, in this instance, it was an executive recruiter that reached out and said, Hey, we are running a search for this role. And they're looking for someone who was marketplace experience and would you be interested? And that was that. And you and your husband have a point system that I really love in, in, in, in surrounds career.

18:15Can you share what that is? Both my husband and I come back, come from a background of investment banking and consulting. And unfortunately that's not always a good thing. And there are a lot of spreadsheets in your household. There are like way more than there need to be honestly. And so when we first started having children, there was a lot of talk about, wow, what does this mean for our careers? And my first child was born in London. And so in the UK, the actual benefits are quite better than they are here. And so as a new mom, you're guaranteed a year off work, which is really, truly spectacular.

18:52And so I took the year, which is very nice. But then we started thinking about when I go back, what does that mean? And how is that going to work? And I want to work less because I can't work the way I did before I had the baby. And we started having these conversations where what does it mean? And what will it mean in the long term? And then we came up with a system where we essentially said, okay, there are some principles for us as a family that are important. One of which is we don't want to be weekend only parents. So we wanted, both of us wanted to spend time in the mornings and the evenings with our children, not just on weekends.

19:30We knew lots of people who often had, for example, two nannies, right? There was someone who would come in and start from seven, work from seven to four, and then another person would show up and work from four to 10, which would give the parents a lot of flexibility to work late or do work dinners and so on. And I totally understand that. I think that everyone should do what works for them because it's this is a really rough road overall. And so you need to know what works for you and what makes you happy. For us, for us, it was very clear that we wanted to spend time with our kids. And so we started rating what does that mean for our careers.

20:07And we decided that any sort of part time role or almost no job would equate to a normal solid corporate job, a nine to five job with some travel and some late dinners or so on. There's always a special project or something is roughly around a two. And then a very busy and demanding role, like a consultant or banker would be a three. Often those roles would require 70, 80, 60 hour weeks that make it very difficult. And so what we decided is that between the two of us, we don't want to really ever go above four and a half. And because neither one of us wanted to let go of our career, it automatically meant neither one of us could also have this high demanding job, because that would indicate that we would be closer to a five.

21:01And so we both started thinking about how do we succeed in more quote unquote jobs that allow a bit more flexibility and allow us to manage our house in a way that give us that space with our family that we felt was very much so needed. But then you said that there was a time when your husband, Rob's company was going through a capital raise and then there were big initiatives for you at TaskRabbit, which I'm assuming is a very solid three or three plus, I don't know. So collectively you said you guys were at a five. In those moments where the points are too high, which I love this point system and coming up with a system and a process for something that feels squishy, how did you decide who needs to take lower points?

21:51And there are so many different ways and it comes down to really communication. Five for two months is okay. Five for a year, probably not. And we needed to understand what it really means and which one of us is willing to give in or offer more flexibility, right? There was a time when we were both really busy and we asked my parents to move in for a little bit of time because that felt like we would get the extra support for our kids, but it also felt very temporary, right? We're both going through a lot of work. It's not going to be permanent, but we wanted some extra support right then. And so we're very fortunate to have that kind of flexibility and very fortunate to have those types of choices.

22:36And it doesn't always perfectly work out because, again, we're both quite ambitious. And obviously, my job is quite demanding. My husband is also building a career. It takes a lot of give and take. It means sometimes I can't go on a business trip when I thought I could or I have to say no to a dinner. And same goes for my husband. And that's sometimes very difficult. How often do you guys check in on this number? And what's your number right now? We check in whenever it feels like it's not working. So if it's working, we're not even having the conversations. If things are not working, we're like, this isn't quite a four and a half.

23:12This is looking closer to five for extended period of time. And again, it's quite personal how we manage it. Sometimes for me, the way I structure it is having the flexibility, right? As an example, my daughter is at a camp this summer and she has a big performance and I want to surprise her. And I didn't think I was going to do this, but I just decided this. And I have the flexibility to say, okay, let me take the second half of the afternoon off and clear my calendar so I can run to the airport on a flight and then show up in Michigan and watch her perform. And I think, so while my job is very demanding, the flexibility and the autonomy that I have really helps to offset some of the long and grueling hours.

24:03Hold onto your wallets. Money Rehab will be right back. And now for some more Money Rehab. Let's hook business now. You have worked at public and private companies. Which do you prefer? There is really no preference, honestly. For me, it just really depends on the mission of the company and what the overall vision is. I really spend a lot of time thinking about the team and thinking about what are the goals and what the company's trying to accomplish. It really doesn't matter how many zeros there are. I think it matters more whether the company has the type of culture that I want to be a part of or that I want to help to set, whether there is an opportunity for continued growth and how fast the company is growing.

24:55So there's a lot of other factors. I haven't really spent time thinking about how different it is, whether it's public or private. But we just generally had CEOs on who find being a public company a pain in the ass or like really stressful to keep checking stock. And there's no doubt that being running a public company would be much more stressful, right? You have to continually answer to the street. I sit on a board of a public company and that is a lot of responsibility and certainly a lot less than what the CEO has to be thinking through every day. and day in, day out. There's pros and cons on both sides, right?

25:36Working as part of the Inca or Ikea family, there's some amazing, amazing benefits. And then it also means that we're not beholden to the street in the same way. But that can also mean that the pressure maybe is not always what it needs to be. And it is really fascinating to understand the trade-offs. I would argue that it's very easy to always say the grass is always greener. I think that it just, it really depends on so many factors. I mean, you have really leaned into this gig economy too. Leadership positions, you mentioned Airbnb, and then you came back from Buenos Aires, went to Uber. What about the gig economy is so fascinating to you?

26:18There's so many things. First thing though, and foremost, is just the way that I grew up, and I think I talked about this, or you mentioned it, that I was in South Dakota. I moved to United States when I was 12, and we moved from Poland into South Dakota. And it was really hard, just like it is for many immigrants, to try to find your footing and try to find a way to make an income and to make ends meet. And so my parents, both of whom had to, both of whom had to work really, really hard. And so they would have double shifts at factories, eventually they opened up a restaurant but their hours were so high and there was no flexibility so my parents couldn't come and see our performance and they couldn't come and do the things that I get to do for my children and so I think having some flexibility and being able to fill in the hours especially some weeks or some months were particularly tough and so trying to make ends meet, having that flexibility to add a meaningful income, I think is really important.

27:26And so I can't help to think that had these types of platforms existed 30, 40 years ago, when we moved here, it would have really provided a lot of help to families like our family. And this is why I have such a soft spot on the supply side of the business. So at Airbnb, I worked with hosts at Uber. I worked with couriers and then a task driver. I obviously oversee the entire company, but I certainly spend a lot of more of my time with taskers and really trying to understand what their needs are and really feeling quite good about the fact that we do provide a lot of opportunity to earn a meaningful income.