How To Not Look Back On Your Career Journey With Regret

Lindsey Knowles

Lindsey Knowles


Name: Lindsey Knowles

Job: VP of Marketing at Winc Wines

Location: Los Angeles, CA

As a kid, what did you want to be when you grew up?

I really struggled with that because the only jobs you know about are the ones that are super visible to you as a kid, whether that’s a teacher, a doctor, or whatever else. Those didn’t necessarily appeal to me, so I didn’t have a really clear idea, which in some ways I think was probably good because it left me open as I was exploring different options.

What was your first full-time job and how did it impact your career?

My first job after graduating college was in finance working for Goldman Sachs in New York. I was there for about five years, and my experience there was really valuable. Right out of college, you don’t even really know how to be in a workplace—and this was a great workplace to learn in. There were a lot of chances to try new things and grow. I was in a sales and client service role, so a lot of that ended up being really relatable to what I do now in marketing and customer experience. At the end of the day, I also learned a lot about myself, specifically that: a) a big company probably wasn’t for me and b) finance wasn’t really my passion. I also knew that I wanted to get back to the West Coast—I’m originally from California—and at that point I was ready for a career shift. So I ended up moving out to Los Angeles to go to business school at UCLA.

How important was it to get your MBA? Is that something you would recommend?

I would certainly recommend it. I think you want to go in with a goal. I had worked in finance, that was my whole frame of reference, and I knew I needed some different skills. UCLA is strong in marketing, entrepreneurship, and tech, and those were areas I really wanted to explore. For me, I got out of it what I was looking for. I learned things I use in my daily life all the time. So you want to have some goal going into it and not just go because you don’t know what else to do. I also had five years of work experience at that time, and looking back, I would not have been ready for business school or gotten nearly as much out of it if I had less work experience. It’s important to bring real life experience to bear when you’re discussing things in class and trying to solve problems.

"I’ve always loved food, beverage, and hospitality, so I was pretty sure that’s where I would end up."

“I’ve always loved food, beverage, and hospitality, so I was pretty sure that’s where I would end up.”


How did you land in your current role?

When I was thinking about leaving finance and what I wanted to do next, I knew I wanted an industry switch. I’ve always loved food, beverage, and hospitality, so I was pretty sure that’s where I would end up. As I was getting ready to leave business school, those were the jobs I was looking at—and at mostly smaller companies, wanting a little more room to grow and to actually really help build something rather than something that was much more established. There was a woman who was a year ahead of me in business school who was working at Winc, and we were kind of in touch, so when this job came up, she put me in touch with the right people—and it was a good match!

Describe an average day as the VP of Marketing at Winc Wines.

A typical day for me is a lot of cross-functional work, which is probably my favorite part about my job. It’s working with our creative team on marketing emails, it’s working with our engineering team with optimizing the website for conversions, it’s working with our operations team making sure our customers get their boxes on time and are happy with their delivery experience. It keeps every day a little different and challenging.

What was the biggest challenge in your career and how did you overcome it?

The biggest challenge was figuring out what I “wanted to be when I grew up.” That’s a really tough thing to figure out. There’s some trial and error. I was lucky enough to get a good job right after college that had a lot of structure, formalized training, and really clear career paths, so I was able to explore within that framework. But when I was ready to make a switch, the whole world was open to me and I had to kind of create my own path. I had to navigate next steps and where I could add value and be happy.

"There’s so much you can’t know until you do it."

“There’s so much you can’t know until you do it.”


What advice would you give to another woman who’s in a similar position now about how to figure out what she’s passionate about and where she belongs?

Be open. And try different things. There’s so much you can’t know until you do it. There are things that I wouldn’t necessarily have thought I would have liked that I ended up really liking (and vice versa). So dive in and try—whether it’s a different type of role or size of company. Until you’ve been in a few different types of workplaces, you can’t know what your preferred working style is or the types of problems you like to solve.

If you could go back and do things differently, would you change anything?

Definitely not. I think all of the career experiences I’ve had have taught me something. One of the best jobs I’ve ever had was working at a bakery in high school. It was straight-up customer service. I was standing behind a bakery counter, handing out donuts, ringing up orders on an old school cash register. It was really eye-opening. I loved working with people, and I think that was an early indication of the path I’d take to sales and client service at Goldman Sachs and now customer experience and marketing at Winc—understanding what makes people tick and trying to engage with them and make them happy. And then learning how to deal with different personality types—you know, people are pre-coffee at 7 a.m., so they’re not necessarily in their best moods!

And I’ve definitely made mistakes, but you learn from those too. I’m not really someone who believes in regrets or wishing you could change the past, because I believe that the past is how we arrive at who we are today. And I’m grateful for all the experiences I’ve had. Even when it didn’t turn out to be a great fit, it definitely added something to my life and taught me something. So I’m happy with the journey that I ended up with.