Olivia Muenter
Updated Jun 12, 2020 @ 5:58 pm
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Credit: Photo by Carter Fish

Even the most successful people had to face a few obstacles to get to where they are today. In our series Failing Forward, women at the top of their game reveal the biggest mistakes they made in their careers—and why they’re actually glad they made them.

If you visit Lauren Chan’s Instagram bio, you’ll find a few different career titles: founder and CEO, “sometimes” model, and former fashion editor for Glamour. Transitioning from plus-size modeling with Ford Models to a freelance writing career for outlets like Interview and T Magazine, then eventually landing a role as an editor isn’t an easy trajectory for anyone. But when you get to know Chan, those steps seem like a thoughtful, logical progression that was meant to be—though that doesn’t mean it was simple.

“When I left my job as an editor, I didn’t know what I was going to do next. I made sure to give myself some time to seriously think through my options,” Chan tells HelloGiggles. The model-writer-editor ultimately chose to create the one thing she had always lacked in the fashion editorial industry: luxury, well-made clothing that actually came in her size.

“When I decided that I wanted to start a brand, the first things I did were research, research, and more research,” Chan says. “The first step beyond that was taking meetings in the garment district to find vendors and partners. The to-do list saw a steep incline after that.”

This led to Chan’s current role: CEO and founder of Henning, a luxury womenswear brand that caters to women size 12 and up. Step by step, Chan built Henning herself, knowing that there was a gap in the market when it came to high-quality clothing for plus-size women.

HelloGiggles spoke to Chan about the career transitions that led her to create Henning, the mistakes she’s made along the way, and how she plans to learn from them in the future. And, as it turns out, trying to be like everyone else when it comes to career success is a little overrated.

Mistake 1: Trying to make her success look like her colleagues’ success.

Beginning her career as a freelance fashion writer, Chan says that she initially thought to emulate the “well-to-do industry veterans who thoughtfully critiqued fashion weeks around the world” was the key to success. From attempting to mirror her colleagues’ style to trying to write about fashion in the same way, Chan says she wanted to blend in with them in “every way”—despite the fact that she was nothing like them.

When following the fashion crowd wasn’t landing her the promotions and the accolades she wanted, she decided to do something different.

“I realized that I needed to find a personal niche, so I began to speak about fashion from my own point of view,” Chan says, explaining how when she started covering plus-size style instead of the traditional, less size-inclusive fashion that the rest of her colleagues were covering, she landed a monthly column and promotions.

Mistake 2: Not being a strong negotiator when it comes to salaries, titles, and beyond.

Even though Chan had a successful writing and editing career at Glamour and beyond, it took her a few years before she learned how to properly advocate for herself and negotiate titles and salaries.

“Early on, I didn’t negotiate because I was scared to, honestly,” Chan says. “I didn’t want to seem difficult or ungrateful. I didn’t want anything to be awkward if I got turned down.”

Eventually, Chan learned how much more money the people around her were making and got “intensely motivated” to make up the difference by asking for more regularly. Those raises and promotions she was hoping for before? This time, she got them.

“As I got more confident in myself and my work, the idea of negotiating for what I’m worth became much easier,” Chan says. “Now, I make sure to push hard, within reason, from the get-go when negotiating.”

These days, when it comes to sharing advice with other women about how to ask for more money, she repeats advice she once received from someone else: “Say the highest number you can with a straight face,” Chan suggests.

Mistake 3: Thinking she was alone in her insecurities.

Though she had found her niche, learned to negotiate, and was more confident than ever in her work, Chan says she often still felt “othered” as a plus-size person in an industry that rarely featured or catered to plus-size women at all.

“It’s easy to feel self-conscious in work environments…even when it comes to what you look like. Imagine how that feeling is magnified in a fashion environment,” Chan shares, explaining how she often felt like the only person who wasn’t a size 2 or wearing designer clothing during her job as a fashion editor.

“I was regularly embarrassed when I had issues with my cheap size 14+ clothes,” Chan shares, naming instances of pants ripping and shirt buttons popping off as examples. Once I started commiserating with my readers and followers about these experiences, I realized I wasn’t alone. There were millions of women experiencing similar frustration with their lack of access to quality plus-size clothing—and that’s part of the reason I started my brand, Henning.”

It was when Chan realized that her insecurities were not only hers— they were many other women’s, too—that she found a community she desperately needed.

“Being vulnerable with those experiences and finding a community with the same experiences is the single greatest experience I’ve had, personally or professionally,” Chan says.

Mistake 4: Trying to figure out everything by herself.

At some point during our careers, we’ve probably all had the thought that if we do everything ourselves, we’ll be (or seem) more successful. Chan says she felt this way more than ever when she started Henning and didn’t know every in and out of clothing production and running a company.

“Most of the time, I obsessively researched, taught myself skills on YouTube, and powered through conversations pretending to know what was being discussed. But every so often, something would come up that felt too overwhelming to tackle solo,” Chan says, explaining that this is what forced her to learn to lean on her community.

“An example: After our first photo shoot, we realized that the armholes in the blazers were too high. Our production was set to start that same week, and I didn’t have time for multiple rounds of redesigning, resampling, and refitting the garments until we got it right,” she says. “After wasting time and energy panicking, I put up a post [on Instagram] requesting Henning’s followers’ arm measurements—and to my surprise, we got tons of responses. We averaged them out and only had to rework the garment once. Problem solved, together.”

Mistake 5: Letting the pressure of a “successful startup” mold get to her.

Even though Chan was excited to begin Henning, she still struggled with trying to fit into the mold of what a successful startup is “supposed” to look like as a CEO and founder.

“These days, there’s a lot of pressure in the startup space to raise a ton of money, grow extremely fast, become famous in the process, and sell the business at a huge multiple or go public,” Chan explains. “The pressure alone to follow the mold was mentally quite taxing on me as a founder.”

Chan has since learned not to let the pressure of starting a new company get to her.

“None of us are perfect—me especially—so I had to take a moment and revisit the lesson from my first mistake,” Chan says. “Clearly, trying to fit in has never worked well for me.”

Through editorial work and in running Henning, Chan shares that the most impactful way not fitting in has changed her career is actually in how it has affected others and “allowed other folks who haven’t fit in to feel seen.”

“They’ve become my readers while I was an editor and [later my] customers at Henning…and, hopefully, they’ll stick with me for whatever the future holds.”