My Journey from Tech to Fashion Styling

If you told me two years ago that I would be making a career out of dressing women in beautiful clothes, I wouldn’t have believed you.

Two years ago, I was living in San Francisco, deeply embedded in the Bay Area tech scene, secretly miserable but living a comfortable, average young millennial lifestyle.

The decision to leave actually began during a Halloween party. I was co-manager of recruiting and HR at a small startup and I was tasked with throwing a Halloween party for the staff. I remember that day so vividly. I was running around to different grocery stores and party decorations stores, picking up bottles of wine and packs of beer, trying to set up a photo-taking station, wrestling with wires to try and connect a projector so the remote employees could call in, talking on the phone with catering and just hating every single minute of it. I remember later that day, standing in the middle of the party, watching everyone else in their Halloween costumes laughing and drinking wine and talking about sprint goals and website updates and test features, and feeling so detached from everything. I should have been enjoying the moment, chatting with everyone, reveling in our week’s wins and taking pride in a successful event but instead I was awestruck by how little I actually cared.

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The Halloween party that started it all

I knew that this was no one else’s fault but my own. My coworkers were very nice people, the company culture itself was supportive and wasn’t toxic, and my manager didn’t try to micromanage me and tried to take an active interest in my development. I knew that the problem lay with me.

I no longer felt connected to my work. I had been in recruiting for about four years and it had lost any excitement or meaning for me. I would essentially go into work on autopilot everyday – never fully engaged or finding joy in my work, my mind trying to focus on what was in front of me but my heart wishing it was elsewhere. It caused a severe cognitive dissonance within me and, as someone who thrives off of living authentically, it was slowly eating me up on the inside.

I remember returning home after that party and texting my boyfriend, “I’m done.”

That night, I made a vow to stop being complacent. I would stop letting jobs and employers and essentially what I thought other people’s opinions were dictate my life trajectory, and start taking matters into my own hands.

Part 1: Exploring My Options

While the buildup sounds quite dramatic, the truth is my decision to enter fashion wasn’t some grand lightening-bolt epiphany. In fact, it wasn’t even my first option.  I entertained a bunch of different career paths in my mind before I finally settled on fashion.

At first, I actually considered being a graphic designer. I had worked with designers often when I was in tech recruiting and I had always respected the field of design. I knew I wanted to do something more creative and I thought that creating beautiful graphics might satisfy that innate urge inside of me.

So in order to test out that theory, I actually enrolled in a few visual design and UX design one-day workshops at General Assembly. Looking back on it, those workshops were extremely helpful in my decision-making process. I was able to get an overall picture of how my days would be spent, what kind of work I would be doing on a daily basis, how it would actually feel to “create” through this medium, and also what kinds of personalities I might find in that field. I truly believe that if anyone is considering embarking on a new career or trying a new profession, that it is a good idea to “dip your toes in” somehow before diving in headfirst.

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Several hours of work and $400+ dollars poorer, I came to the ultimate conclusion that design was not the profession for me. I realized that, while I enjoyed the research and visual aspect of the work, it felt too precise, too sterile and too removed from the actual “creation” process for me. I didn’t want to spend my days drawing vectors on a computer – I wanted the creation process to be more tangible, more sensory. I wanted to touch my work in a way that I couldn’t with a computer. I also realized that while I enjoyed being surrounded by beautiful things and touching and seeing beautiful things, that the process of actually building them didn’t call to me as much. UX Design resonated even less with me – I realized that I had no interest in designing logos or building apps and websites.

Although I didn’t come away from those classes with a fiery passion for graphic design, I do not regret taking them a single bit. While some may have considered it a waste of money, I considered it an investment in my future. It gave me a newfound respect for the profession, a deeper understanding of the world of designers and also more clarity on what I liked and disliked as a career.

Part 2: Exploring Myself

While I knew it was important to become acquainted with my options, it was even more important for me to become acquainted with myself. After allowing external factors like salary and social status to dictate my life path for so many years, I needed to relearn what my actual passions and desires were.

Two things helped me immensely during this time: journaling and a concept called Ikigai. Journaling is hands-down one of the most transformative practices I’ve ever put into place in my life. I plan on writing a blog post soon about the benefits of journaling and how it can help you on your path to self-awareness. During the time that I was figuring out my career transition, I journaled every single day – my thoughts, my fears, my desires, my ideas and visions for my ideal life. Being able to work through my thoughts on paper really helped me put into perspective what exactly I wanted to change about my current life and what I hoped to accomplish for my future.

I stumbled upon the concept of Ikigai through a Youtube video. I was consuming a lot of self-help content at this time and found this video during a late night media binge (as one does).

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Ikigai is a Japanese concept and essentially means, “one’s reason for being”. It is the intersection of four primary elements – what you love, what the world needs, what you are good at and what you can get paid for.

When you are able to find a sweet spot where all four elements intersect, it is said to bring fulfillment, happiness and a longer life.

Having this concept as a prompt was extremely helpful in getting me to brainstorm all the elements of my career that I had ignored in the past. For many years, I solely focused on what I was good at and what could make me money, leaving out my interests and my desires to meaningfully contribute to the world. Based on the Ikigai Venn diagram above, I was working from a profession mindset, which left me comfortable but wholly empty.

I remember doing this exercise around 2 AM in my bedroom. Some parts were easier than others. For things I was good at, I wrote “listening and relating to others, conversation, emotional intelligence, giving advice”, and for things that I loved, I had a long extensive list – clothes, beauty, food, travel, Youtube, reading, connecting with new people, listening to podcasts, sharing ideas with others, expressively myself creatively whether it was through photos, writing, style etc… But when it came to what the world needed and what I could be paid for, I felt the pressure to be realistic and practical. When I wrote down that people needed “help with gaining self-confidence”, I thought that this meant that I should probably become a therapist, given my skills. However, I knew deep down that going into mental health wasn’t the path for me. I needed to think of what excited me first, and then build possible options from there.

To be frank, “fashion stylist” likely came to me out of sheer lack of sleep and delirium. It was past 3 in the morning. I was thinking about what things sparked excitement in me, and I thought about how I genuinely enjoyed clothes. I always noticed what my friends and people on the street were wearing, I could spend hours endlessly browsing through fashion blogs, online stores, and fashion videos without getting bored, and I loved talking about things like fabric and clothing construction. I remember having the random thought to myself, “Well, what if my job was styling clothes on people?”

It was then that something clicked. I realized that being a fashion stylist ticked all my boxes – it utilized the skills that I was good at (conversation, intuition, connecting with strangers), would stimulate my interests (fashion, creativity, connection), would contribute to the world in some way (help empower women and men to feel good about themselves), and – if I was successful – would help pay the bills.

Part 3: Exploring The Internet

Once the seed of being a fashion stylist was planted, I was ravenous for knowledge.

I spent hours trawling the internet for information on fashion styling – what an average day was like, what the pay was like, who I would work with, and more. To be perfectly honest, I had to really dig to find reliable information. As the About Me section of this blog will tell you, there is an oddly sparse amount of information online on how to practically build a career in fashion styling – that doesn’t involve you already majoring in fashion.

I give a lot of my credit to the School of Style‘s free Youtube videos for first teaching me the basics of what life as a fashion stylist was like.

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Started by celebrity stylist Luke Storey and personal stylist / Youtube personality Lauren Messiah, the School of Style Youtube account has a treasure trove of digestible short videos on topics that range from landing an assistant stylist gig to pricing your styling services. The School of Style actually has two certification courses – one in Editorial Styling and one in Personal Styling. While I personally did not take either of the courses, I gained a lot of valuable knowledge just from watching the free videos.

The Business of Fashion was also a really good source for in-depth articles on the fashion industry. It was there that I found a few interviews from successful stylists who had “made it” and it was helpful to read their journeys and see how they had built a career for themselves through this field.

Part 4: Exploring with Others

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To say that I was a bit of a pest during this time period would be an understatement.

Once I knew that I was interested in fashion styling, it was as if I was determined to put it out into the universe as much as possible.

Any social situation that I found myself in – happy hour, a lunch date, a friend’s birthday party – I found a way to briefly slip in that I was in the midst of “pursuing fashion styling”. While this may sound cringey, I think it’s something that many people overlook when job hunting. We want to make a major change happen but we keep it bottled up to ourselves. We are afraid to ask for help or we believe that we will be judged but what I  have personally experienced is that if you are sincere and respectful, then people are happy to give advice or at least connect you to someone else who may give you that advice.

I began putting out feelers for “informational interviews”. My strategy was two-fold: I began systematically applying to more entry-level fashion styling jobs, hoping that my professional background and my eagerness would translate to at least an informational interview, and I also reached out people in my network who currently worked or at some point worked in the fashion industry.

The best contact I made was a recruiter named Sara at The RealReal. I actually found her through a former roommate of mine who was working in a customer service role at The RealReal at the time. After seeing on LinkedIn that my old roommate was working at the company, I reached out to her on Facebook and asked if she wouldn’t mind giving me advice or putting me in touch with someone in recruiting. She connected me to Sara, who suggested that I come in to The RealReal office to chat with her about potential job opportunities.

Although I specifically went in to interview for a recruiting role (I thought working in HR at a fashion company was still a step in the right direction), the conversation quickly shifted into me asking her a ton of questions about the industry itself, about fashion styling, and about how I could market myself as an emerging stylist. I ended up telling her everything – how I was hoping to leave tech, how fashion styling was ultimately my interest, how I was trying to break into the industry without any past experience and how I was just looking for any “in”. Sara was incredibly kind and knowledgeable about the industry – having worked as a previous StitchFix stylist and as a fashion recruiter for years – and she gave me tons of useful advice.

She ultimately was the one who convinced me not to go into recruiting at a fashion company, if styling was ultimately what I wanted. If I was going to make this transition, I needed to dedicate all my time and efforts towards it. She was also the one who informed me that one of the best ways to truly get experience as a stylist was to become an assistant to an already established stylist and even gave me the name of a well-known wardrobe stylist who a friend of hers had assisted in the past.

Part 5: Getting the Job!

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Although I wouldn’t necessarily label myself as a highly spiritual person, I truly do believe in the concept of manifestation – that if you truly want something from the universe, you have to ask for it.

After sending out my resume to several job listings in San Francisco, I finally got an invitation for a phone interview with a fashion showroom that had just opened in the city. The job listing had been for part-time stylist position for the showroom’s regular clients. I remember being nervous before speaking on the phone with the showroom manager, but at the same time, at peace. It’s hard to describe now but I think part of me knew that that phone call was exactly where I needed to be. I knew who I was and what I had to offer and although I very badly wanted the job, I knew the only thing I could do in that moment was be real. I spoke with the showroom manager, Alana and told her about my background, my career change, my people skills and I also told her that if given the opportunity, I would work incredibly hard to prove my worth as an employee.

One take-home assignment and in-person interview later, I was offered the job.

Around the same time, after I had cold emailed the wardrobe stylist that Sara had given me the name of, I received a phone call from MGKStyle’s operations manager who mentioned that they were looking for assistants and that my email intrigued her. After a phone interview with her and MGK herself, I was also offered a part-time gig with them as an assistant stylist.

Final Thoughts

In October of 2019, I was miserable, lost, and desperately wanted to do something creative with my life but had no idea how.

Two months later, I had not one but two fashion styling jobs.

But this incredibly long story isn’t me trying to brag. If anything, it’s me trying to show that change is a process. My career transition from tech recruiting to fashion styling may have seemed like a big leap from the outside, but in truth, it was a series of small, calculated and hopeful efforts on my part to be vulnerable and put myself out there.

We’ve all heard the phrase, “luck is what happens when preparation meets opportunity”. If I hadn’t gone through those self-reflection exercises to figure out what I wanted, if I hadn’t ruled out professions that weren’t a good fit for me, if I hadn’t reached out to others for help or done my research – I may never have gotten the job opportunities that I did. So if you yourself are reading this and are on the brink of making a change, I hope my story has given you some inspiration on where to start.

Just know that the most important step is to start.

~

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