Real Life: Your Second Career

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Earlier this summer, over my birthday weekend, I was sitting around the table with a bunch of friends. We were eating dinner, drinking lots of wine, enjoying the gorgeous weather, and generally just basking in the laziness of an awesome sumer night. You know how these nights go…you end up having some really fun, great conversations!

As the conversation turned to our jobs and our futures, one person posed to the group, “If you guys could do anything for your next career, what would you be doing?” I loved this question, not only because it assumes something I think everyone should consider — that what you do now won’t always be what you’re doing — but it was fascinating to hear everyone’s responses and see whose jobs would be similar to what they work on now, and whose would be a total departure. For example, it was no surprise that someone who works as a consultant was interested in getting into venture capital, or a financial accountant was interested in rising through the ranks and working as a CFO.

For my own response, I initially thought I would have to really hem and haw over it, but almost immediately, my answer came to me. I like to think that means something.

But before I reveal all (ha!), I was curious to pose this question to you all today, because it’s one I’ve been thinking about ever since that dinner. It’s so easy to think of your life as static, even though intellectually you know that’s not the case. Sometimes when you’re unhappy with your job, or where you live, or any number of other things, it’s hard to imagine what it will feel like on the other side. I think opening yourself up to the possibility of change, and concurrently keeping your ambitions in mind can help lead your life into surprising and (good) uncharted territory. As I’ve headed into my 30s, perhaps this has been on my mind more as we grapple with if/when we would have a kid, or what that next career would be (and when it would start and how we’d get into it), or where the next decade will take us and where we’ll be when we hit 40 (!). Seeing myself through this different lens has meant I’m kind of fascinated with seeing my friends through it as well — I wonder what people really want and where they’re headed.

So here I am, being nosy and curious with you! If you could do anything for your “next career” — i.e., something reasonably realistic that you would want to work on and build for another long-ish period of your life — what would it be? What would it take for you to do it, and sustain it? I’m legit interested in hearing what you think about doing.

Ready for my response? It might surprise you. 

While I really, truly enjoy my job now and can see myself doing it for many more years, I would eventually like to get into the wine business. When I was in culinary school, ironically, one of my favorite series of classes were the two we took on wine and spirits. I adored learning about all things wine, specifically how it was made and how wine styles are developed. Later, when I was working as a freelance food writer in San Francisco, I also worked a harvest at a local winery, which was a custom crush facility. It’s no longer in business the way it once was (and has since relocated to Napa), but the idea behind this winery was anyone could come in and make their own wine. You bought grapes from some of the most notable vineyards along the west coast (wine enthusiasts might recognize names such as To Kalon, Beckstoffer, and Stagecoach), came up with a wine plan in terms of how it would be fermented, aged, and blended, and could even design your own label.

The result was that in the harvest I worked, the winery made 1000 different wines (for reference, a mega-winery like Robert Mondavi makes around 20). My job at the winery was to teach clients about making wine, as well as helping with all the manual labor required of a harvest. Honestly? It was the most fun I ever had at a job, and it got me hooked. I could ramble on about wine and my work there, but you get the gist. So yes, that’s what I’d love my second career to be — something in the wine industry, preferable close to either growing or making. Are you surprised? Here I am in a past life, on the right, teaching people about fermentation:


Your turn: what would you want your second career to be?


Top Image: Jakub, Foodie’s Feed


  1. 10.15.14

    Great post! I love questions like this. Although I went to school for Journalism and my first full-time job was in the Journalism field, my heart is in Creative Writing. It’s always been, but it was only last week when I sat down and thought “Why didn’t I pursue Creative Writing as a career instead of Journalism?” I would love to write a series of novels for young adults.

    I’m 22, so this is definitely my next venture!

    • 10.15.14

      Ooh, the YA novels sounds awesome! You know, it’s totally possible. I’m sure you’re familiar with how the Divergent author got her start? You really just never know!

  2. 10.15.14

    You know, I can’t remember what my answer was to this question!

    I can’t think of a singular dream job, but I know that working on multiple projects and having a satisfying home life is what’s important to me. I’ll never do just one thing (my brain would drive me crazier than usual), but I do want to be challenged and passionate about what I’m doing.

    Dream job – luxury hotel reviewer/travel writer, among other things.

    • 10.15.14

      I think that last thing was one of yours, the other was a biz you’re already working on (the charity one!).

  3. 10.15.14

    Love this! I’d love to have a bottle of wine from the “McGinley Vineyards!” Ha. I would love learn more about food photography and shoot for cookbooks. I think about it every time I purchase a cookbook – which is often!

    • 10.15.14

      Funnily enough, there is already a McGinley vineyard down in the south central coast of California, not far from Santa Barbara!

      I probably have an idea or two for how you could get into that business, having worked with food photographers, food writers, stylists, etc for the San Francisco Chronicle. Let me know if you ever want to talk! :)

  4. 10.15.14

    I love this question! I think about teaching & if this is something I really want to be doing for 20-30 years. Maybe it will be but I also think about what I’d do if I had the chance to start over in college. I think I’d like to study graphic design & get into a more artistic, creative field.

    For me I always had a very linear track in my head of go to college, study and then get a job in that field. I’m beginning to think that there are other ways to navigate your career & this definitely makes me wonder where I will be in 15 years!

    • 10.15.14

      I feel the same way re: the college track. I don’t have many regrets in life, but two that are very acute for me are a) not studying abroad and b) not studying something different in college. I went with business because it seemed so practical; if I could do it over again, I think I’d study Art History and French.

      I think as Americans we are often trained to follow that path, since that’s what generations before us did and it worked out for them. But I think the Internet kind of changed everything. I mean, look at me, I’m a self-taught designer who owns a design business now, so to your aspirations I say — anything is possible!

  5. 10.15.14
    Kodi said:

    I work in photography now, shooting, doing sales and design for albums, cards, etc. But I think I’d love advertising — when in college, my absolute favorite, stay up late excited to work on them projects were designing advertising campaigns for business. And I’d like to think I was good at it, my professor recommended I send one to the company. Which I never did, but I love my current job, my hours, my coworkers and where I’m able to live because of where my job is located. No complaints here!

  6. 10.15.14

    I love this. I think about this question all the time. I’d love to own my own brick and mortar store with an in-house styling business. What I love best about my job now is that I can (I hope) make women feel stronger and more confident through style and understanding how to dress for their bodies. I’d also moonlight as a novelist, ha ha. Great post!

  7. 10.15.14

    This question scares the bejesus out of me because a slew of things come to mind, but one thing is certain, it would be far from what I’m doing right now :)I’ll have to get back to you with my answer!

  8. 10.15.14
    whitney said:

    Great post Victoria. I think I’d like to be a chef, or maybe a travel writer, or something in the art field or at a museum. Thanks for making me think :)

    On a side note…you should do a post on your favorite wines, or maybe your picks for affordable but delicious options. I’d love to read about that! On another side note, let’s get wine together next time I’m in town!


  9. 10.15.14

    I absolutely love this post and this question. Working in an industry that is largely data driven, but being immensely passionate about clothing, i’d love to design my own line of perfect fitting denim :) Color me selfish, but I think the creativity of that profession, coupled with the challenge of launching a business would be so rewarding. Plus, i’d finally find denim that fit well!

    Thank you for the thought provoking post, Victoria!

  10. 10.15.14
    Maria said:

    I’m working at a snails pace to be a small business owner for an online boutique with a goal to be my own boss and have the ability to make my own business decisions.

  11. 10.15.14

    Oh that’s so interesting! I love questions like these. It’s something I’ve been pondering as well, only because I’m not sure that I could do what I’m doing for very many more years. I’m still not sure of the answer to be honest… but I love to hear that yours is so vastly different – maybe I should be thinking more out of the box!

  12. 10.15.14
    Caroline said:

    I think about this all the time as I’m in the beginning of my career. I currently work at a fashion magazine but day dream about culinary school and going to France for a year to learn it all and eventually owning my own place (similar to Meryl Streep in It’s Complicated…I’d take the divorce to live her life!) Love this post!

  13. 10.15.14

    So interesting! Wine is an art in and of itself so it could happen. I asked myself that question when I started Rose & Ivy, it was what I always wanted to do but making it happen was the hardest part. Great post :)

  14. 10.15.14
    Caro said:

    Glad to know I’m not the only one musing over future career changes! Maybe it’s because the freelancing I’ve done has been varied enough that it feels like I’ve already made a bunch of career changes, but I feel this question is always in the back of my mind. Most of the options I mull over are in creative fields… but if there were no restrictions, I’d have to say politics. I’m passionate about them and I’ve always wanted to work on a campaign!

  15. 10.15.14
    Swati said:

    Loved reading this – your posts always make me pause and think! I recently read something about how our passions as a kid show what truly excites and motivates us. For me that was drawing and designing elaborate evening gowns. So, maybe start my own clothing line or open a boutique? We shall see!

    • 10.15.14

      I agree with you. And I think it’s true, because as a kid, I was passionate about layout design, and…wine! Haha. (No but really, it was an important part of the eating/entertaining experience in my family, and my mom was fine with me enjoying a little wine and tasting different varieties.).

      And you know, as for your own dream, the first step is always putting it out there! Maybe share your drawings online or sell them as prints. Who knows — that could lead to an actual dress design commission!

  16. 10.15.14

    It’s as if you read my mind/recent ponderings. I am so on the same page in terms of thinking through what is next but less ready to step out and make a big change.

    I’m taking a more phased approach. Right now I work in biotech quality but I am SO incredibly drawn to stationery. I would just love to own my own company that produces letterpress greeting cards, stationery sets, invitations and calligraphy services. Phase 1 was formally learn calligraphy. I’m currently in phase 2 and will be addressing wedding envelopes until the cows come home! (which I’m really very thrilled about). Still brainstorming the next phases but am in no rush :)

    Can’t wait to learn what your new direction will be!

    xx Katie
    lovely letters

  17. 10.15.14

    I love this post! I am already on my third career, so I’m going to try to stick with this therapy gig for a while. But I can already picture my fourth– bed and breakfast owner. I’m saving that for the retirement phase though. It sounds like you belong back in CA with those vino aspirations, although I hear the vineyards out on Long Island are great!

  18. 10.15.14

    Another very strong and powerful post. I’ve been reading through some of your previous posts and finally decided to drop a comment on this one. I signed up for your newsletter, so please keep up the informative posts!

  19. 10.15.14
    Abby said:

    This is so funny that you wrote about this today! I was just thinking about it myself and looking up grad school programs for something so different than the career I’m in. I’m a reality TV producer but I’m moving to Chicago and thinking it may be good for another change. I have always felt drawn to international non-profits and human rights and would love to find some way to do work in that realm, preferably without having to go back to school (my degree is in religion and writing, rhetoric and communication -so not too far off already). Great post- you’re right I wouldn’t have guessed the wine business! I will say my family works in the bourbon industry and it seems like nothing but fun honestly!

  20. 10.15.14
    Ellie said:

    I’ve tried to answer this question several times in the past 6 months or so and I am having so much trouble coming up with an answer! I currently work as a catering sales manager for three hotels and not only love what I do, but know where I want to go. The only thing I can think of that I might do otherwise would be interior design. I explored that career option in the beginning of high school and if it weren’t for the less shiny parts (think HVAC, plumbing, etc), I think I would have pursued that path further.

    I loved this post and hearing about what your second career would be! I would love to see some wine education posts that highlight your expertise and let you dabble in your alter-ego career :)

  21. 10.16.14

    Love this post Victoria! I think about this often. I work in accounting for a large bank and as much I’ve always enjoyed that my mind works well with numbers I think in my next job that will take a backseat to being a little more creative. I dont think I can answer the question with a specific answer at this point but I know I love food, travel and photography so I’m hoping to explore these interests more in the upcoming years.

    Also I love hearing about your next career in the wine industry! I know nothing about wine other than that I love it hah. I hope you’ll share more of your knowledge and general interest in future posts. Best of luck with that second career, I can see it working out well for you!

  22. 10.16.14

    Very interesting question! Im surprised that it actually took me a second to think about what I would do! Although I absolutely love what I do second career would def be a food + travel blogger from somewhat of an average persons point of view! They are two things I am really passionate about and would thoroughly enjoy spending my later years doing

  23. 10.16.14
    Rose said:

    Victoria, you really have some of the best posts around (Grace of Stripes & Sequins and I were just talking yesterday how your blog & Hallie’s are the two we always read when we get time!).

    Anyways, I think what I would do would depend on a lot on where I was, physically and mentally. I grew up and went to school with the intention of working in music in some way, and carried that intention through graduation although I didn’t pursue it as actively as I could have/should have. Once I moved to NYC, I just needed a job, and somehow fell into fashion marketing, where I’ve stayed for 3+ years…part of me would still like to get into music (promotions, booking, A&R, something like that). Then, there’s another part of me that knows if/when I ever move back home, I would want to get involved in urban revitalization, working with businesses to encourage them to open stores and offices there, making it a truly fun place to live. Lastly, I have always LOVED baking (my mom taught me to make pie crust when I was about 6) and I’d really love to go to pastry school and open/work in a niche or boutique bakery.

    The good thing about our generation is, we can do/be all these things if we want! It’s never really too late to change course. And, as a longtime follower/reader, I would absolutely come to you for wine recommendations or to buy from your someday-winery :)

  24. 10.16.14
    JC said:

    I have really been thinking about this lately, since talking about babies has me thinking a part time job might be ideal for our family. Currently I am an engineer, and I’m not enthused about it (never go go school to please your parents). I think moving into yoga instructing, or massage therapy would be a wonderful career move for the time being.

  25. 10.16.14

    What a great question! I loved reading your answer, and here’s mine (which I wouldn’t have dreamed of until recently): I’d like to start a tech start-up.

  26. 10.16.14
    tasha said:

    CMO of a tech company or I would be a director of a homeless shelter. It really is a toss up of what I would do.

  27. 10.16.14
    Vanessa said:

    This post hit me like a sack of bricks because I’ve been thinking about these things a lot lately. We are approaching a crossroads soon, and I don’t know how it’s going to pan out or what I’ll end up doing. It’s the first time since I graduated high school in which I’ve felt absolutely rudderless! Part of the problem is there are so MANY things I love that choosing one is absolute torture.

  28. 10.16.14
    Sarah said:

    Love this post! And it definitely is making me think. I’m really not sure what I would want to do… there’s what I want and what I should. Oh there I go being a complete control freak.

    Now some self reflection time…

    – Sarah :)

  29. 10.16.14

    Great topic! My background is in public relations, and I would love to eventually pursue a career in restaurant PR, however, I always feel this tug to go in to social work, either working in mental health services, homelessness or decreasing our criminal justice system’s recidivism rates.

    I love food, and I enjoy talking and writing about it, but sometimes I feel that it’s a bit frivolous, at least compared to social work.

    Thankfully, I know that I don’t have to pick and choose, I can always find a way to make both sides work. :)

  30. 10.17.14
    Martie said:

    Victoria, that´s such a nice post! Actually, while reading your post I was thinking about having my own vineyard but also be a freelance writer. I am not even a big wine drinker to begin with, but I totally agree with you, the whole process is kind of fascinating and also therapeutic in a way…. But maybe I look at it in a far too romantic way :)

    Creative writing also was always a passion of mine – so we´ll see what will happen!

    Thanks for sharing,


  31. 10.17.14
    Agoprime said:
  32. 10.17.14
    Jenn said:

    My hubby is right there with you. He was a kid in a candy store in France, soaking up all of the knowledge as we traveled around. He literally lights up when he can talk to someone about wine making, wine growing, wine tasting, etc. Our tour guides in Burgundy were ex-Pats from England that provide English-speaking tours. I’m trying to convince him that’s what we should do – pick a region, learn about it and each day he can provide the knowledge he’s bursting at the seams with to others. I’ll just drive around with our tour groups and enjoy the wine! ;)

  33. 10.17.14
    Nicola said:

    I love this post too and am actually nearing a cross roads too. I have decided to take the lunge and move into small business ownership, it makes me punch the air with equi-excitement/fear!!

    In the long long run, I would love to have a boutique hotel in France, Provence or the Dordogne. I love hosting and can’t think of anything better than spending time with people who are in the holiday spirit everyday!

  34. 10.19.14

    fascinating question! I love blogging but who knows where that will go in a few years. I think I’d love to focus more on my photography. I always wanted to be a national geographic photographer, but maybe now I’d love to shoot hotels and interiors. Photography is my passion and I don’t push myself enough at the moment.

  35. 10.20.14
    Jessica said:

    It’s funny because in a heartbeat I said have my own boutique. I like styling people and I love the idea of decorating my boutique. Starting from the ground up gives me goose bumps in a good way. But at the moment, right out of college, it’s not the most realistic of dreams. However, it’s what everyone encourages me to pursue eventually. Even my significant other wants to help me start up a boutique just because he knows that it’s my happy place helping people look good. I live in a small town and hope that this dream can come true one day :)

  36. 10.20.14
    Joanna said:

    I love this question, as I think it reminds us that we’re never stuck and (really, with just enough guts and planning) can make big changes in our careers if the desire is there. I think I would study art restoration with the goal of working in a museum somewhere in Europe. I studied a lot of art history and majored in studio art with an emphasis in sculpture in college, so it wouldn’t be a big move away from my interests, but definitely a change from my current work!

  37. 10.21.14
    Christine said:

    Definitely going to pose this question at my next dinner party! I just transitioned from a job in marketing and social media in a small accessories start-up to a position in brand partnerships in a larger tech startup. I also blog/freelance write/teach yoga classes–so plenty of opportunities to dabble. I’d love my next career to be as a full-time writer: my biggest dream is to be an editor at a magazine, maybe with enough time on the side to write a book :)

  38. 10.21.14

    I would happily serve your wine at my boutique hotel/B&B :)

  39. 10.23.14
    Sarah said:

    This post comes at such an interesting time for me. I have several people in my life who have been pushing me to write a book on my experiences as a new mom because they say I’m real and people can relate to me (huge compliment!). And I realize that this idea I’ve always had to be a full time writer is what I’d like to eventually fish out for myself. Maybe write a book, but I also love the idea of having my own magazine, but on my own terms. I know A LOT goes into a magazine, but I don’t want to sacrifice my time with my family for it. So an online magazine seems right up my alley. It’s something I’ve been looking into off and on for a couple years now. And now you’ve inspired me to write a post about this very thing for my own blog tomorrow. :)

  40. 10.23.14
    Caroline said:

    Love hearing this! I’m currently in the process of launching my own wine business, and after growing up in the Napa Valley and moving to NY, I never thought it a million years an interest in the wine industry would grow to what I feel now! Cheers to making it happen!


  41. 11.16.14
    Jessie said:

    This is SO inspiring to me, darling! Love to hear about where you can see your life going down the road, and can’t wait to watch it all unfold. :) XOXO

  42. 2.2.15

    There was a time when I’d say a baker, then I heard about the way-early mornings. Then I thought TV host, but then I realized wearing heavy makeup and having my hair constantly pulled and curled sounded awful. At one point, I also thought event planner, then I realized I actually enjoy having weekends to myself. Now I’m a freelance magazine writer, and I do actually love what I do (finally!), but I’m really fascinated by graphic design, too. I love logos and branding and typography and all that jazz. I want to be a prolific writer that knows good design—that seems like the ultimate package to me :)

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