Your Life After Tech

Ep 005: Jenny Shirey - From Research to Red Wines

• Life After Tech • Season 1 • Episode 5

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While staying in tech (UX research), Jenny Shirey takes a bold leap into the world of wine. It's a tale of resilience and transformation, where wine becomes more than just a beverage—it's a gateway to a fulfilling second career.

As Jenny contemplates opening a wine shop or bar, her tale of transition offers invaluable lessons for anyone considering a career change. Setting deadlines and embracing accountability emerge as crucial strategies to overcome the overwhelming task of creating a business plan. 

With an emphasis on finding joy and fulfillment in one's work, this episode is a heartfelt reminder that life is too short to be stuck in unsatisfying roles. Jenny encourages us to pursue opportunities that resonate with our passions, ensuring that happiness and work are not mutually exclusive.

Connect with her @JennyTeachesWine on Instagram.

PS: She passed her test!

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Debbie:

Welcome to the your Life After Tech podcast. This is Episode 5. I'm Debbie Levitt. Don't forget to check out our lifeaftertech. info multiverse, including our book, Discord, community coaching and more, Because you might be done with tech, tech might be done with you, or you're thinking about adding non-tech work to your tech career. Today's guest is Jenny Shirey, J-E-N-N-Y, S-H-I-R-E-Y, and you can find her on Instagram at JennyTeachesWine. J-e-n-n-y, T-E-A-C-H-E-S-W-I-N-E. We'll be talking about how she's staying in tech, but she has been studying and taking courses related to wine. She's even working in a wine bar and has some interesting future plans that include staying in tech and working outside of tech in wine. Let's get to know Jenny.

Jenny:

Hey everyone, I'm Jenny Shirey. I have been working in tech for many years, since 2011. I'm working in design since 2005, when I started my career as a graphic designer in design. Since 2005, when I started my career as a graphic designer, I went back to school to get a master's degree at Carnegie Mellon a master of design in 2009, and then, in 2011, switched over to user experience design, worked at some smaller companies, some bigger companies. I also even ended up working as a manager in Copenhagen, denmark, for about three and a half years, and then came back to the Bay Area. I was really enjoying all of this and then decided that I was feeling kind of burnt out. We can talk about that later, decided to start my own consulting business, and so that was something that I started in January 2020. And that was the year that, of course, everything changed. Oh, that's a tough year to start consulting business, and so that was something that I started in January 2020.

Debbie:

And that was the year that, of course, everything changed. Oh, that's a tough year to start a business.

Jenny:

Mm. Hmm, it was tough, but you know, my business has survived. It's called Bay Bridge UX. It's a consulting business of one. It's me. That was also the year that I realized I wanted to explore things other than UX. So in 2020, I also started getting into learning about wine seriously, and that has really morphed into a new career path, or perhaps I should say potential career path. I'm still figuring it out.

Jenny:

Career path. Exactly At this point, I am also teaching classes about wine at the San Francisco Wine School. I'm working as a part-time bartender at a woman-owned wine bar in Soma, san Francisco, called Wine Down, and I have also worked at a wine shop for a few months. So I'm really just exploring a lot of different options in the wine industry while still keeping my consulting business. So yeah, nice to meet everyone and nice to see you, debbie.

Debbie:

Yeah, thanks so much. I was so interested in your story when it popped up in a Slack that we're both in, so you've talked a little bit about your tech background and where your tech career brought you. I'm curious how wine popped up as a possibility for you.

Jenny:

Yeah Well, living in San Francisco, we're so close to Napa and Sonoma. I had been going to taste wine in these places for many years and I realized during the pandemic I had a lot of extra time, as many of us did. I was very fortunate that, you know, I was already working from home, so, um, I was safe. Of course, I didn't have a lot of clients, so that was a bummer. But with that extra time I thought why don't I go ahead and start learning about this thing, that I really love wine, and I had been thinking about possibly taking a formal class, a formal exam called the introductory exam in the Court of Master Sommeliers.

Jenny:

The reason I thought about that was I had seen this documentary on Netflix called Psalm into the Bottle. I don't know if any of you have seen it, but it was pretty. I think a lot of people watched it and they got really excited about this idea of these like super knowledgeable sommeliers that pass this test. It's said to be the hardest test in the world. That is obviously not the test that I did. That was a level four and I did level one, so on your way levels to go, yeah, on my way.

Jenny:

So I passed, and then I think I just got the bug of wow, learning about wine. This is not just about wine, it's about the earth, it's about biology, it's about science, chemistry, it's about history, it's about culture, and then also I just love traveling. So for me, traveling to places and being able to experience the food and the wine of that place is so special and important. I'm a huge foodie. I just love eating all kinds of food. Learning about how wine pairs with different kinds of foods and what cultures make what types of wine, has just been so much fun. So really I think that's what drew me to it is wine, is culture, and also wine is just really fun. And at the same time, I was starting to become really disillusioned with the tech industry, and I think during COVID a lot of us became disillusioned with kind of capitalism in general. So it was fun to just say this is something that I truly enjoy, that brings me joy, that brings a lot of people joy, and I want to pursue it more.

Debbie:

Yeah, really interesting. Thank you for that. So you've, so you're juggling a lot of things in the wine multiverse. Right now you're doing some bartending, which probably gives you the opportunity to be junior sommelier of some sort. Is that accurate?

Jenny:

Yeah, I mean, it's funny, funny the term sommelier. It sounds so fancy but it really just means anyone that serves wine, so okay. So, yes, I guess I could say I'm a sommelier. Um, the wine bar I'm at is very casual, like their mission is actually to make awesome wine down to earth. So I would probably not call myself that there, because you know, I don't want to use a word that might make people feel intimidated. That said, I am thinking about taking the certified sommelier exam, which is the level two within the court of master sommeliers. So if I pass that, I could call myself a certified sommelier. I'm actually taking a totally different exam on Monday, so we can talk about that too, but yeah, exams are interesting.

Debbie:

Thank you. Yeah, so you've passed level one. You're thinking about level two, but it sounds like in parallel there's something else you're studying that has an exam. Yeah, parallel, there's something else you're studying that that has an exam.

Jenny:

Yeah, sure, tell us more. Yeah, this is funny because it's so different from user experience design, where you learn on the job. And with wine you learn on the job. You know no question. You have to learn those service aspects and also just understanding what people really want. And a lot of people don't know how to talk about wine, so you kind of have to decode what they're saying. They like um, and you learn that with time and you learn how to be gracious and even bartending like I seriously have started to become a little bit of that therapist bartender. There have been times when someone's crying at the bar and I'm, you know, there to listen and that's fine. And when people come in and they're celebrating, we can celebrate together and that's really fun too.

Jenny:

So the credentials though these are really helpful just to make sure that you have your theory, and of course, it's also a shorthand for anybody who's looking to hire you. If you don't have 10 years or 15 years of experience working in wine, it's a shorthand to say this person does know their theory. And if it's with the Court of Master Sums, you have a service portion of the exam as well. So this person can do formal service. The one that I chose to take on Monday is called the Certified Specialist of Wine exam. It's through the Society of Wine Educators and that's because I absolutely love teaching and I love their approach on education, and so this one's a purely theoretical exam. It is difficult. It has a 40% first time pass rate. So we'll see um. I will say to the listeners at this point when this podcast has been released, I will know whether or not I passed um, and you can find out by going to my instagram, because I will certainly be posting there either way if I do not pass then?

Jenny:

oh, instantaneously.

Debbie:

So, thank goodness, so you'll tell us and we'll get it in the show notes, so we will on monday. Yeah, oh great, okay, yeah, because the show's not going live for a few weeks, so please let me know I'll. I'll be. I'll be excited for you and hopeful, and even if you don't make it for some reason, it sounds like you get another chance yeah, you have to pay a little bit of money.

Jenny:

Of course, all of these tests have fees, but you certainly can take it as many times as you want.

Debbie:

So I'm curious about kind of the shorter, long term future for this. You know, we know that many of us would like to stay in tech if we can get the work, but we don't know what the future might be. That's an unknown. What's the future for the wine multiverse for you? What is the goal for you? Maybe business-wise?

Jenny:

That's exactly what I'm trying to find out right now. I actually have signed up for an online class to create a business plan because I've realized that for me, I need deadlines to get things done. I can certainly set my own deadlines and say I want to make a business plan by the end of the year, but it's better for me when I have homework and I half about possibly opening up either a wine shop or a wine bar or a combination of both. I've looked into things like legally, what would be required in terms of alcohol permitting, and I've looked a little bit into financing and pricing and I've been testing out working for other people, but I haven't actually come down and put the numbers into a plan and I haven't said exactly this is my audience, this is my product, this is what I want to sell. Basically, this is the whole business plan.

Jenny:

That has been really intimidating to me. To be honest, it's not something I've needed to do for my UX consulting business. For UX consulting. I already knew UX very well and there's not really any startup costs. I already had a laptop. I could just. I mean it's creating a website letting people know that you're available. I mean it's creating a website letting people know that you're available. It is difficult to get clients, so that's a challenge with UX consulting. Is that sales part of it? But it's completely different from having $100,000 to $300,000 to open up a wine bar and potentially renovate and get equipment and wine and product and all of that and I've heard that a lot of that is the license.

Jenny:

Oh, the license is, I wouldn't say, the biggest cost. I think the equipment is the biggest cost.

Jenny:

Yeah, from what I've heard yeah, but the license is pricey as well and, honestly, that is the biggest time hurdle from what I've heard. So it's just completely different and I'm forcing myself to um face. My fears make the business plan. So there are options. All of this is to say if someone is thinking about other avenues. It's really easy to get into a rut of just saying I want to do this, I have this dream without thinking about the realities of it, and to me it's really important to take small steps towards it. So, experimenting with do I even like this type of work? That's why I've worked for other people for the past year to see if I enjoy teaching, selling wine, bartending. It's not that I'm doing it for the money, it's more to find out. It's like an internship. Do I actually enjoy doing this and what can I learn from this experience?

Debbie:

So that's how I've been approaching it. I think that's really smart is to try it out. It's almost like people know I'm not a huge fan of the minimum viable product idea, but it's kind of like taking that baby step where it's still a very low risk thing because you haven't laid out a lot of money to do some teaching or work for someone else, and you can start to get deeper into the industry and see is this really where I would want to put more of my time, energy or money?

Jenny:

Absolutely yeah, and I also did hire a career coach last year who I love. She is part cheerleader and part challenger, so she has been really wonderful at asking me questions to help me decide what I really want to do. But also I have a lot of self-doubt and I did need someone to just say you can definitely do this, and maybe you're not even dreaming big enough, and for me that was a really worthwhile investment, I think, just to push myself to continue moving. I think also, when you do spend money on something, then you take it seriously too. So she's expensive but worth it. So I would highly recommend Career Coaches if you find someone that you love and click with.

Debbie:

Yeah, great idea. I do recommend that as well. So I wanted to ask you because I'm asking everybody this, thinking about the wine business and the directions you can go with it, how would you say that that matches some of what I call your core personal qualities or your key personality traits?

Jenny:

yeah, I love learning. I place a high value on being an expert in something. Um, I don't know that that's like a personality trait, but it's definitely something. When I took a strengths finder exam, that was something that came up as a strength.

Debbie:

Okay.

Jenny:

I also love, uh, teaching other people, um, so, spreading this knowledge. So it's like accumulating knowledge and then sharing it with others. So that really fits well, especially the, you know, leading wine tastings or teaching classes, which which I am already doing now and then I think the other part is the independence, but I would say UX consulting also fits that value. So it's not that I need to start a wine business to have that value. I could start any business and I have already started a business. So that itch is already being scratched. I think it's just trying to decide what will make me happy, especially now, in this sort of second half of my life. What do I really want to spend my time on?

Debbie:

Yeah, and sometimes our hobbies and our passions can turn into businesses that people will pay for, and sometimes they're just better as hobbies and they're not exactly moneymakers. So it sounds like you've run into something that has some earning potential.

Jenny:

Yeah, that's such a good point, debbie, because, like I also love writing and I have written some creative nonfiction, some memoir type of writings I don't consider any type of a money making business. At some point Maybe I'll self-publish, but that's not something that I'm expecting to turn into a viable career option, especially living in San Francisco. But wine, you know, people are drinking wine and there's many wine bars and wine shops and wine clubs and wine classes, so people do make money, and sometimes really good money, doing this. So it seems like a viable option. Then again, you know, doing the business plan will definitely help me figure that out as well.

Debbie:

Yeah, it sounds like the business plan, among other things, might help you understand. Can you work for yourself, you know? Might you have to continue working for someone else, and maybe how long that runway is before you'd be able to branch out more on your own? That's just my guess.

Jenny:

Exactly. Yeah, I've realized about myself that I I don't mind working for someone else if we fit well together. But I think that was one of my issues with tech is I found myself continuing to be in these companies where I have a fairly kind and laid back and not laid back, I would say. I have a kind and empathetic working style and management style that often did not fit well with tech in general, I would say, and a lot of tech um leadership within these companies, especially these highly technical B2B companies that I was working within um it was very aggressive and kind of wanting people to put more and more in and be very critical of each other, just in a way that really didn't fit my personality, Whereas I've been finding that in the wide industry, not everyone I'm meeting is a great fit for me, but I have been finding some people that I feel like I work really well with, so that's definitely an option.

Debbie:

Now I'm going to ask you a question which you don't have to answer, but I see a lot of talk on LinkedIn and some other places where people say and I'm just going to make this up as an example I don't want to be a bartender, I don't want to work at Walmart, these are low paying jobs and so they're off the table. You know, I live in an expensive place. I don't want to do that, or maybe they even think it's beneath them. You don't have to tell us what being a bartender pays, but maybe how do you get past some of the thoughts or the self-talk around oh my gosh, do I want to go be a bartender at an hourly rate or for the tips, where it might be a lower number than you're used to?

Jenny:

Yeah, absolutely, and to be honest, I don't know that. I don't think that just bartending would be able to be a viable option for me, unless it was at a bar where possibly the prices are a bit higher and they are looking for I'm thinking of sort of Michelin level restaurants. Sometimes we'll have wine bars associated with them. I do think the pay there might end up being a livable salary even in San Francisco. However, that is thinking about it as being sort of beneath someone to serve other people.

Jenny:

I think um does rub me the wrong way, because I think that there is a lot of joy in serving other people and giving other people a pleasurable experience. That is like the highlight of their day. You're really making their day better. Um, I also really do love that educational aspect. So anytime I can teach someone about wine, well, I'm, you know, uh, helping them make a choice on what wine they want to drink. You know explaining that this one has purines and what does that even mean? How does that taste? Those sorts of things Like if they say they like, um, chablis, we only have California wine at our wine bar, so what would they enjoy if they like Chablis or Beaujolais or something.

Jenny:

Um, that part is still really fun to me. That said, this is all new. So I do think that, um, after years and years of doing anything, you can start to be a little bit jaded, and that's why I think it's great for people to realize they can always grow, they can always change and it's okay to change your realize. They can always grow, they can always change and it's okay to change your career. You don't have to stay in one thing. Just because you chose it doesn't mean you have to stay there forever.

Debbie:

Yeah, very true. Looking back at some of your arc, the last at least handful of years, is there anything you feel that might have been a mistake or regret or something you wish you could have done differently?

Jenny:

That's such a good question and it is something that I have been reflecting on lately. I honestly think that everything in my life has been a learning experience. So I would say that when I look back at my past choices, you know I made the best decision for myself with the information that I had at that time and so, in that sense, a lot of choices that I made maybe in my 20s or 30s I wouldn't make today, but that doesn't mean that it was the wrong choice at that time. Perhaps the only thing that I wish I had done differently is that in some tech companies I have been around some people who are pretty toxic, who disparaged the work of designers. So either my work or people that I managed I'm talking about like product people and engineers who didn't respect designers' work, and sometimes this would really come out in the comments they would make, in just being dismissive, in not being willing to work together with me or my team, and I wish that I had stood up for myself and my team more and said this is not okay and we deserve to be treated with respect.

Jenny:

And I think at that time, especially being a woman in a male dominated industry, being soft-spoken, being I don't like conflict, you know. That was really hard for me to do, and a lot of times I would just shy away from it and just allow things to happen that really were not good for my mental health or the mental health of my team. So that's. The only regret that I have is that I didn't say this is not okay and you need to be more respectful.

Debbie:

Yeah, thank you for sharing that. I'm sure a lot of people identify with that. Especially when our jobs can feel so insecure, we have to decide how much do I rock the boat when I don't know how that's going to come back to bite me later?

Jenny:

Yeah, I will say I have often made the decision to leave a company rather than staying in a situation that I felt was toxic and damaging for my own mental health, and maybe for some people that is the best choice. For other people, it might actually be a really good growth experience to stand up for yourself, to stay and try to make things better, and often we also don't have the financial means to leave, especially in today's tech job situation, where there's not enough jobs and too many people looking. So I do think it's possible to set boundaries and just really be mindful of what is good for your mental health and what is not good for your mental health, and part of that is why I ended up working for myself, and that's also something that I'm considering as I'm thinking about what I want to do next is what's going to fit with my life and my emotional needs too.

Debbie:

Yeah, thanks, that definitely makes sense. Yeah, thanks, that definitely makes sense.

Jenny:

So, we might have listeners or viewers who are thinking about leaving tech or adding non-tech work to their tech universe. What advice would you like to give them? If you still enjoy tech and you have a job that you love and you just want something else, it's fine to have that something else. Just be a hobby. It doesn't need to pay your bills. Not everything needs to be a side gig. So I think it's lovely when we find things that we can just really enjoy doing and we enjoy doing them in our time, that we're not, you know, earning money or working for someone else. Tech has so many good things about it in terms of, you know, often we're able to work remotely. The pay is wonderful if you are working full-time within a company. Benefits like healthcare and retirement money, you know, all of those are things that I kind of took for granted paid time off. When I started working for myself, I realized, oh, I had a really cushy job and maybe I didn't realize it or I took a lot of it for granted. Now, that said, if you have become disillusioned with tech like I did and you're wanting just less of it in your life, that's also fine. There's a lot of ways to you know you could do something like I did and become more of a consultant or freelancer and just have less hours and then it feels less all consuming and I think that was really healthy for me. Now I can choose to work with clients that I really love, that my values align with theirs, and I enjoy that time with them. So I didn't have to completely leave tech and, to be honest, I don't know if I ever will.

Jenny:

I think I'll continue consulting. I'm really enjoying the research projects I'm doing right now. The user research projects I'm doing right now, uh, the user research projects. Um, so I think you know taking small steps to kind of figure out what you want. Maybe you go in this direction, a couple of steps. That's not quite right. You go in this direction, that's okay. You can just keep experimenting. You don't have to have everything figured out right away before, and you also don't have to commit to something for the rest of your life. You can always try something out and make a decision that that's not for you.

Debbie:

Thank you All great reminders. Got a couple more questions. How can people get in touch with you, follow you, do business with you, take your class? Give us some ways that we can find you yeah, well, I still am doing consulting work.

Jenny:

I've actually pivoted over into strategic user research, um. I love talking with people and I love helping companies figure out who are they really making their products for. Um, and that's funny because it has so much overlap with what I'm thinking about with wine as well. Who do I want to make products for? So I love helping other companies find that out as well, and I've been really enjoying that type of work. So if anyone needs that help with that, um, you can find me at babebridgeuxcom and, of course, you can find me at babebridgeuxcom and, of course, on LinkedIn under Jenny Shirey.

Jenny:

If you're interested in wine, I do teach classes on wine and I post about them on Instagram. So at Jenny teaches wine, j-e-n-n-y teaches wine all one word. You can find me on Instagram. That's where I'll announce, for example, when I'm teaching at the San Francisco Wine School. Excuse me, I teach a lot of classes on California wine there and they are virtual, so you can join from anywhere in the world, and they can even ship wine samples to you for the tasting. So that's really fun and I will also be posting there whenever I decide what's next. You know if I'm doing any kind of an online wine club or maybe even opening up a physical space or just doing pop-ups. So stay tuned. I would love to have you follow me there and engage with me, and I will definitely respond to messages on Instagram as well.

Debbie:

Excellent, excellent. You know I was thinking so many people ask me about Coming from especially UX and they say what can I do with my transferable skills, you know what? And they think about going laterally, in a sense, from one tech job To another tech job. Like I'm a UX researcher, where else can I do UX research? And I really hope that Hearing the stories you've been telling Will help that light bulb. Go on for people where you can use your core personal qualities. You can use some of the skills that you put into tech and they're just going to pop up somewhere else and you might not feel like you're applying UX research or design specifically to wine, but because these are part of who you are, you're still bringing it. It's still you.

Jenny:

Absolutely. Also, you know, I've been creating these experiences for people and thinking about customer journeys for so many years now that I can think about that in relation to someone who's signing up for a wine class for the first time, or somebody who, um is coming to a wine bar and trying to figure out what they want to drink. You know, what is that journey Like? All of this is very, very transferable. It's just thinking about someone else's experience, how you can make that better, how you can, um make it, uh, an experience where people want to come back. So, uh, maybe we call them guests instead of users, but you know, it's still thinking about like, how do you serve the needs of other people and what are their unmet needs that you can serve? And maybe there's like a new opening in the market for Love it, love it.

Debbie:

You're speaking my language and you know it, so I always like to try to give guests the last word. So anything else you want to add to what has been already said?

Jenny:

Oh, maybe I would just add I do really believe that life should be fun and enjoyable, and something that whatever you're doing with your time should be, most of the time, something that you enjoy doing. So if you are in a situation where your job fills you with dread on a daily basis, I'm sure there is some other solution out there for you that can make you a sustainable living and still allow you to enjoy the people that you're with, enjoy the work that you're creating well, great jenny.

Debbie:

Thank you so much for being on the show thanks so much for having me Debbie.

Jenny:

I really appreciate it. This is a lot of fun.

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