Coming from a family of accountants and engineers, Sheryl Jacobson didn't have any real models of what to do with a liberal arts degree. But with a love of history, culture, and story she knew she wanted an international experience after graduation. Her consulting life bounced her all over the world and presented her with opportunties she never could have imagined. At some point, she realized she could come home and still have other adventures. Find out how balancing adventure and loneliness is a dance that can work out in the end.
Coming from a family of accountants and engineers, Sheryl Jacobson didn't have any real models of what to do with a liberal arts degree. But with a love of history, culture, and story she knew she wanted an international experience after graduation. She landed a job with the boutique Monitor Group, working first in marketing and market research, just beyond her comfort zone. Her consulting life bounced her all over the world and presented her with opportunities she never could have imagined from London and Hong Kong to Istanbul and Shanghai, even as Monitor became part of Deloitte. Meeting her husband along the way and contemplating motherhood after many years, she realized she could come home and still have other adventures.
In this episode, find out from Sheryl how balancing adventure and loneliness is a dance that can work out in the end…on today's Roads Taken with Leslie Jennings Rowley.
About This Episode’s Guest
Sheryl Jacobson is the lead strategy partner for one of Deloitte’s Life Sciences clients. She has spent the last 20+ years helping clients and her sole employer Deloitte tackle strategic challenges and make the most of opportunities for growth and innovation. She lives in her to-the-studs renovated Brownstone in Harlem with her husband and their son.
For another story about the ups and downs of expat life with Heather McNemar.
Find more episodes at https://roadstakenshow.com
Executive Producer/Host: Leslie Jennings Rowley
Music: Brian Burrows
Email the show at RoadsTakenShow@gmail.com
Sheryl Jacobson: It's funny, my career has been back and forth international. You underestimate the loneliness and overestimate the adventure when you think about these things. But the loneliness and like learning to figure out your mechanisms, you know, for those times, I think that was helpful and helpful for kind of the adventures that I kind of had since then.
Leslie Jennings Rowley: Coming from a family of accountants and engineers, Sheryl Jacobson didn't have any real models for what to do with a liberal arts degree. But with a love of history, culture, and story, she knew she wanted an international experience after graduation. Her consulting life bounced her all over the world and presented her with opportunities she never could have imagined. At some point, she realized she could come home and still have other adventures. Find out how balancing adventure and loneliness is a dance that can work out in the end on today's Roads Taken with me, Leslie Jennings Rowley.
Today I'm here with my friend Sheryl Jacobson and we're going to talk about paths that lead from the mountains to the valleys to the big city and everywhere in between.
So Sheryl, thanks so much for being here today.
SJ: Thank you for having me. I'm excited. I've been listening for a long time. So when I got my invitation, I was like, all right, my turn.
LJR: Long-time listener, first-time caller. I love it. Okay. So, you know then, these are the two questions I ask everybody. So we'll ask them of you. When we were in college, who were you? And when we were getting ready to leave, who did you think you would become?
SJ: Kind of the same answer to both. I had no idea on either one. You know, I came to Dartmouth, I moved around a lot as a kid, but then ended up in a relatively small town in Western Colorado and was, you know, wildly pleasantly surprised to get into Dartmouth. I'd never visited, saw the pictures, thought this place is beautiful. This is what a New England college kind of looks like and was happy to be there and happy to be part of the adventure. But a lot of my four years and beyond was like, yeah, figuring out who I was, figuring out what this totally different world was. And not doing it particularly deliberately, right? I was, I don't know, 17 when I got there and 21 when, when I graduated. So it was just a lot of exploration. And then when I left, it was similar. I came from a family of accountants and engineers. You know, my parents were the first ones in their family that went to college. My mom even went back to school because she had us when she was really young. So she went back to school to become an accountant, you know, so truly a family of accountants and engineers. And so the notion of kind of career options, you know, and what those could actually be? I just didn't know, you know, I kind of fell into what I'm doing and luckily I love it, but definitely fell into what I was doing. So I knew I didn't want to be a doctor. I didn't want to be an archaeologist. I knew I didn't want to be an accountant or an engineer. And that was probably about it.
LJR: Yeah, so, and the kind of schooling your mom would have gone back to was fairly vocational, and yet here you were at the liberal arts, and kind of eating it all up, and history was where you found yourself. But it could have been a number of places I'm sure.
SJ: Mainly because of the like really terrible grades my freshman year in in basic chemistry and in like I realized I was not prepared for intro to calculus and I was like science is not for me. Let me go read books. I'm really good at reading books.
But no, my dad went to the Colorado School of Mines and my mom went to Mesa State College for an accounting engineer. So it was a very…my brother went to the School of Engineering at University of Colorado and my sister went to accounting at University of Denver. So, I wasn't joking. A family of accountants and engineers is where I came from.
LJR: Yeah, with no other models of what something more expansive might look like. So, when we were leaving and you were saying, I still don't know and I'm going to be forging that for a while what were the first couple of steps?
SJ: It was really funny. I was listening to Andy's podcast, I think last week. Cause I was listening to some of the ones that really resonated. And I believe he was the one that said consulting is for the lost. Totally true. I had a lot of student loans. So it was very clear I had to get a job and I was not welcomed back on my family's couch. Like my dad was like, I love you, but we got you to college. Like now you need to start making your own way.
So I started doing the executive recruiting process kind of as you do. And that was actually how I started figuring out you know some careers. So I was really looking at marketing and then some consulting. And I got just really lucky. So they got my, I got acquired. But it was Monitor Group, which was a little boutique corporate and business strategy. They were starting out a new group that was going to be focused on marketing strategy. So it was right when the consulting industry was going from like general management, consulting, business consulting, to being more specialized. And I thought I liked marketing cause I, and I still do, but marketing is like the story of why people do what they do and how to change that. And I really liked that. It appealed to my history major and my love of literature. And this particular group wanted to go from basically PhDs and econometricians to a traditional consulting model. So they wanted undergraduates with some form of social skills. And I fit the bill. They were basically like, you can talk to a wide variety of humans. You're hired. You are fundamentally and truly, we could talk about imposter syndrome and all these other pieces. I was unqualified for this job, like just flat out unqualified for this job, but I got it. And they paid me enough that I could pay my student loans and pay rent. And they were also a global profit pool. So the one thing I really knew I wanted to do was work internationally. That was…I don't know quite know why. I think it's because I lived a lot in books and I lived a lot in my head and I loved history. And so an opportunity to actually live and work internationally. And Monitor was the place that offered me that because you could move around pretty fluidly. It was 1200 people and you could move around. And so I was like, all right.
LJR: Had you taken advantage of any of the international things at Dartmouth?
SJ: I did the semester abroad for in Italy. So I was in Siena.
LJR: I knew that because you were with me.
SJ: That's, yeah! I could not speak Italian. They should not have sent me on that trip. Like, in all seriousness. I think they were basically like, Really she shouldn't go. Her gentleman's Bs in Italian. It's going to make that semester hard. But I, like, I loved it and it was really hard. Like it was lonely and fun [LJR: It was!] and full of adventures and…
LJR: The funny thing, Sheryl, you were talking about reading and losing yourself in literature. I did that it in that semester. I read more British and American kind of 19th century fiction than I have ever in my life [SJ: Yes!] because I was so, I needed to be thinking in English because our days and nights were in Italian and I was, I was so lonely that I was like, I'll make friends with these, you know, British courtesans. I don't know. It was very weird.
SJ: I remember we would pass those books around. I have a visceral memory of like reading that genre extensively there. And it's funny, we'll talk about it, because my career has been back and forth international. You underestimate the loneliness and overestimate the adventure…
LJR: Right!
Sj: …when you think about these things. And it's not that the adventure wasn't there, right? We had great times. Go down to Capri, or you just get lost wandering. I gained so much weight, not just because of my Italian mom's wonderful cooking, but also I would just buy jars of Nutella and eat it, you know, while I was reading. I came off the plane and everybody was like, oh, interesting. She needs to get back into fitness. But the loneliness and, and like learning to figure out your mechanisms, you know, for those times, I think that was helpful and helpful for kind of the adventures that I kind of had since then.
LJR: I totally…that resonates with me of kind of the allure and the adventure is all only what you see, even in hindsight, like you forget the lonely and you're like, Oh, but it was so stunning. And it was so this. And so it makes you want to do it more. And then you find yourself there again. And you're like, Oh, shoot. Okay, I forgot this part. So, okay. So the allure of being in an international company that gave you the opportunities to kind of dabble and do different things was great as a young person. So kind of how did that blossom both professionally and then into the other sides of who you were becoming?
SJ: So when I had started monitor like July 8th. 'cause basically I had over the course of Dartmouth, taken like semesters off or done as many credits just 'cause I was paying for a chunk of my school. My parents definitely contributed and, you know, I had loans and, and everything else. But I was, I was paying for as much as my school as possible. So what that meant is your student loans started to come due. Six months after you complete the credits, not six months or three months, whatever it was after you walk. And so I it was July 8th. I still celebrate my work anniversary. So I'm technically, I guess, with the same company. And I was, I started in Boston. So in our Cambridge office, but I got lucky enough that I got put on a project in Toronto kind of over the summer. I was in Hong Kong actually in February of that year. And then I transferred to London and I was based in London from 97 to 2000, all around Europe. But it was, it was a really interesting time. Cause when I got there, literally July 8, this particular group was just forming. I got handed the little SAS book, which is this little red book, which is basically how do you program statistics in SAS? I had never taken a statistics course and I like programs, I don't know, the Apple II-e that we had at home, like when I was 15, it was basically a market research job. And in hindsight, awesome. Like just, it got me grounded in data. It got me grounded in logic. It really got me grounded in, in marketing. You know, and, and behavior, but, oh, was when I say I was unqualified for that job, I massively was, and so I worked really hard my first year basically to be like, I can't get fired. I must pay those student loans and I'm going to figure this out. I can do this. I have no idea how I'm going to do this, but I can do this and made great friends amongst the other analysts that I'm actually still good friends with. And then ended up when I moved to London, it was basically to found this marketing group or be part of the founding members in London. I had my apartment in London. But then it was wonderful. I just wanted any country, any topic. And so they were like, do you want to do automobile association, you know, up in the peak district? And I was like, sure. You know, do you want to do data networks in Stuttgart? Absolutely. You know, do you want to do durable goods in Istanbul? Like go! So it was, it was awesome. And to do that in your early. It's funny. It's like, all I had to do was like pack up some books, you know, in storage and I could go wander the world. And it was also at the time when the really cheap airlines hadn't come in yet. And so it was really expensive to go back to London. And so basically the firm's policy was like, Hey, if it's cheaper than your air ticket back to London, yeah, go to Stockholm, you know.
LJR: Just for fun.
SJ: Yeah, exactly. Or, you know, meet somebody in Milan or…But in ’99, 2000, I did kind of, it was a good question, but it was a naive question. I thought like I needed to figure out what I wanted to do when I grew up, you know. Everybody was starting to think about business school and the network and that kind of thing. And I knew I wasn't going to be a lifer expat because that's just a particular path to go on. And it was lonely. I, you know, I was dating somebody at the time actually was with monitor and you have expat friends, but you don't really have British friends. You know, your British colleagues, and ironically, some of my colleagues from there have now become my friends, you know, cause we've just been working together for so, so long, but just also kind of realizing like, okay, this isn't, this isn't my forever home. So let me move to the next stage and start to figure out what that is. And I was also in the, like, do I like consulting? You know, I'd been doing it for so many years. I'd worked really hard at it. I was good at what I was doing, but like nobody ever says that they want to be a consulting partner, right? It's just, that's not the career aspiration of a senior consultant or even a manager. And that's when I first came to New York was in 2000. And that was starting to figure out that I liked the job. Starting to figure out that I didn't, I did do business school, but I didn't necessarily need business school. But it was starting to figure out that I actually really liked the job which then helped me start to figure out, like, who I was in that context, which was good. I'm still figuring it out, but at least that was the start of it.
LJR: Yeah. And that's funny because you and Andy say that consulting is for the lost and you started to find yourself only when you realized you liked the job.
SJ: Yeah. Yeah.
LJR: There's a little irony there.
SJ: Yeah, it totally is. I think that I, I had so much growing up to do. Which, you know, I was very...young coming into Dartmouth. I had a, just a very particular set of experiences and perfectly good set of experiences. But there was just so much of, you remember when people would call it The City?
LJR: Yeah.
SJ: And like, and I had no idea which city they were talking about. Like, that's just the perfect, and a lot of people didn't, don't get me wrong, but that was like the perfect microcosm for me and, and Dartmouth, I thought. And so I, I just had a lot of. Like grounding and learning and sorting things out. And when I started at Monitor, I just started working so hard. Probably because I was just, like, I was insecure that I was qualified for that job. And so I lost myself in work for a while, too. You know, and so there was this kind of moment of moving out, coming to New York, and starting to figure out, okay, so what is it that I actually want to do? And, you know, where do I want to live and who do I want to be kind of started more then.
LJR: Yeah. Well, and that makes sense because so many of those earlier opportunities where you were taking advantage of, you know, the opportunity to go to Istanbul, the opportunity to go to Stuttgart, that was very reactive and you finally are at a stage where you're still, you know, you've proven that part, and then now you get to exercise a little agency of, you know, what do I want, how do I craft these, my own opportunities, even within this organization? But the organization is changing, right?
SJ: Well, so I have always been with Monitor and now Monitor Deloitte. So I am, I don't know how many others in the class of 96 have only had one employer, but that is effectively what I have done. And I haven't even...I did the Friday, Saturday program at Columbia. [LJR: Oh, wow.] So my longest time not working was maternity leave.
LJR: Whoa. Which we can say was a little bit later than some of our maternity leaves.
SJ: Yes.
LJR: So get us from that move back to New York to that first breath of, breath of a different break.
SJ: Yeah. It's, it was funny. So I realized I liked the job. Realize I needed to really understand how organizations work, which I realize ironic as a consultant in an organization realized that I needed to start working with a client for a longer term because I was a great project manager. So I started working as a consultant in pharmaceuticals. So about an hour away from my, away from my house and realized I loved it. Like that, that actually is a part of the job that I really liked was the people side of it and the empathy. And as a consultant, in order for somebody to hire you, they have to be asking for help, even if it's to implement SAP, right? Which, you know, people are like, that's not very exciting. I'm like, but they're asking for help. It's part of a transformation, a journey. So I realized that about the job and I was like, that's cool. I like it. And I loved the people I was working with. Love, love, loved it. And I knew Monitor wasn't doing well economically. We all knew it. Like, but to do work that you love with people that you really like, that's, that is not an opportunity that comes along very often. So anyway, I love my job. Realized I didn't need to do like business school to switch jobs, but I did want the language system. So I did the executive MBA at Columbia. I'd also had bought actually the house I'm still in. I bought a brownstone in Harlem that I gut-renovated and I had a mortgage. So student loans were paid off, but had a mortgage. So two year business school kind of wasn't, wasn't the right path for me. 2011, I met my husband in New York and I needed a change. I need to go on the learning curve again. And I was super grateful and lucky–and we'll come back to the loneliness piece—that my husband had the flexibility to move and monitor needed leadership in Asia, we were either going to go bankrupt. So we have to break up in bankruptcy or we were going to get acquired.And modern needed leadership in, in Asia. And so I moved to Shanghai and Mark, my husband came with me again. Very grateful for that. We've been dating like nine months. So, [LJR: Oh] Yeah. And he's a black man that was doing basically it and didn't speak Mandarin. And Sheryl's naivete was like, you'll totally find a job in Shanghai. Mark is not that naive. Mark was like, oh, okay, we'll, we'll give this a try. And it was, it was amazing, but it goes back to that kind of loneliness piece. I think when you think about these expat roles, like I had a job, I had things I had to do, you know, kind of thing. Mark had to sort all those things out. And so it's so much harder on the spouse than it is on the person going, even with all those components. Anyway, we end up getting married. He was raised in Trinidad, though he's came to the States at 17 or so. So we had an amazing wedding down in Trinidad, gigantic party. And I wasn't a person that necessarily said, like, I need to be a mom. I wasn't opposed to it, but it wasn't a... You know, that's something that I really want. Like, I don't think my biological clock ever ticked. I never heard it, if it did. Maybe I was just working and enjoying what I did. But I also wasn't opposed. And so, but it gets to be a, gosh, we, Mark and I met maybe at 36. So when you hit like 39, you know, it's kind of like, Oh, it's going to happen or not going to happen. And got really lucky in that it did. And I stayed in China until 2016, Deloitte acquired us in 2013. So stayed to lead the strategy practice for the region and life sciences consulting for the Asia Pac region. And then my expat contract was up and I got pregnant that year. And so actually it was. It all worked out because the China firm, so Deloitte China, you know, for client service I wasn't that useful at a certain point. Like I could sell projects but I couldn't, I wasn't going to be around for delivery and I shouldn't have a client relationship because I can't do delivery. In the U. S. Deloitte didn't know who I was. Right? Except for my network. I hadn't worked there yet. And so, I spent like a month in Japan, wandering around took some other time off on different piece parts. So I had a six month of traditional maternity leave, but honestly, probably two months prior to that I was, I was wandering the world at, you know, seven to eight months pregnant and It was, it was great. It was a really nice time. It was a really nice time with Mark because it was a benefit of him not working. So we had, you know, eight months: two just us and then six months when Michael was just born for us to be kind of a nuclear family.
LJR: Wow. And where did you set up shop as a nuclear family?
SJ: So we came back to the house in New York. So I kept the brownstone. That I had bought in ’03. It's a three family brownstone up in Harlem. 130th. And Mark had moved in prior to us leaving. And then we came right back to, to here afterwards.
LJR: Nice. And so, Michael was born in 20...16. 16. Yeah, so I was 41 when he was born and ready for a new adventure.
LJR: Yeah, again It's one of those adventures that you think about all the great things and all the other stuff we completely forget about.
SJ: I still remember the lack of sleep First few years it goes through but it has been really nice Like you everybody has kids if and when they should have kids like life kind of works out that way For me, it was really nice to do it when I was economically stable and I was more mature for lack of a better word. And I'm at a point in my career where I'm very comfortable making the trade-offs that are needed to spend the time with my son and. I know there's trade-offs, and I'm fine with those trade-offs. I love my job. I'm good at my job. I believe Deloitte thinks I'm good at my job. But I also know what the priority actually is. And it's like, I only have so many book fairs, you know, with my son. I'm gonna show my butt up for that book fair! Just no, you know, kind of thing. And I'm, I'm at a point in my life where I can do that. And I think I'm lucky and privileged in that, in that way.
LJR: Yeah. Well, he's lucky and privileged now, too, to get you there.
SJ: Not what he said to me this morning.
LJR: Right. Right, now we're gonna get to…
SJ: That stage of motherhood.
LJR: Yeah, totally. Well, so, lots of twists and turns to get to here, but as you said about parenthood, it kind of happens when you need it. Life seems to put you in places that you need it when you need it. And if you were to go back now and tell your young 20-something Sheryl, Hey, let me give you a preview. Let's look at all this. What would her reaction be?
SJ: Gosh. It would be some version of like, Huh! Like, didn't know that was a pathway in life that could be taken. I think I probably expected myself to be, you know, kind of, I don't know, you know, settled earlier. I wouldn't have thought it would be a consulting job or whatever, but I think there would have been an appreciation for that adventure and the kind of path taken.
I think I also honestly probably would have told her though, like, just stay in Europe longer. Like you are bouncing around Europe in your twenties with an expense account. Like, could you just stay? Like, just give it a try for a little bit longer. So anyway, life will always work out regardless of, of where you are in the moment and the stresses and strains you may have.
LJR: Exactly. And had you stayed longer, some other things might not have fallen into place. So it sounds like you're exactly where you're supposed to be right now. Who knows what this you know, next time of motherhood and working and all of that will bring, but thank you so much, Sheryl, for sharing this much with us.
SJ: Absolutely.
LJR: That was Cheryl Jacobson, leader of Deloitte Consulting's medtech practice, as well as the lead strategy partner for one of Deloitte's life sciences clients. She spent the last 20 plus years helping clients and her sole employer, Deloitte, tackle strategic challenges and make the most of opportunities for growth and innovation. She lives in her to-the-studs renovated brownstone in Harlem with her husband and their son.
We have one more episode next week in this season before our next hiatus. We thank you for continuing to listen and follow us wherever you get your podcasts. And thanks for rating, reviewing, and passing along word of our show so that other people can become acquainted with my amazing guests and me, Leslie Jennings Rowley, on Roads Taken.