Lessons in failure and audacity from a women’s career coach and influencer

Before she was a career influencer, Emilie Aries struggled personally and professionally. She thinks we need to talk more about failure, be audacious and stop giving 100% to things we don't care about.
Emilie Aries (photo by Emma Keith)

Emilie Aries approaches the table I’ve saved for us and immediately says, “I was reading your blog in the Lyft on the way over and it’s so good.” I try not to scream with excitement.

Let me back up. Emilie is an influencer in women’s career development with an impressive resume. I first learned about her work when she was co-hosting the Stuff Mom Never Told You (SMNTY) podcast for HowStuffWorks. I was struck by her well-researched strong opinions and her constant acknowledgment of how hard things are for women, and harder still for women of color.

When Emilie left SMNTY to focus full-time on building Bossed Up, her training company focused on supporting  women through career growth and transitions, I continued to follow what she was up to online. After connecting through social media, we met up in San Antonio, where she was giving a keynote speech at a conference the next day.

“Focus is the name of the game.”

We started our conversation by bonding over how difficult writing can be. While some days are productive and rewarding, others are terrible. “I have days where I’ll watch TV for three hours when I should be writing and then cry about it,” Emilie admits. Her recipe for her (mostly) good days? Having a routine, setting realistic goals and prioritizing. “Focus is the name of the game. You cannot do it all well, all the time.”

We moved on to what she thinks we’re not discussing enough when it comes to women’s careers — failure. “We’re obsessed with stories about people who achieve fast success and win big. But you don’t see the muddling through the middle part — all the shit that goes down on the way to success.” I asked her for an example of the shit in the middle of her professional journey, and she said, “I burned out at age 24, at the peak of a political organizing career.”

“You need to get the fuck out of Rhode Island.”

Here’s the backstory: in her early 20s, Emilie took a job as the state director for Obama for America in Rhode Island. The youngest state director in the country, she worked constantly because she felt like she was trying to “save the world.” She stopped exercising and was in an unhealthy relationship with a man who struggled with alcoholism. “Everything looked so good on paper, but I felt so unhappy and out of control.”

When she got laid off in 2010, Emilie became deeply depressed about the state of her life, career and relationship. But she managed to gather the courage to leave her relationship, which she describes as “the hardest thing I’ve ever done — when you leave addicts they don’t take it very well.” For a brief moment, she accepted another executive director job in Rhode Island but quickly backed out when a friend told her, “You need to get the fuck out of Rhode Island,” and convinced her to move to Washington D.C., the city she’d always dreamed of living in.

She drove to D.C. with her dog and a coffee table and rented a one-bedroom basement apartment where she slept on a mattress on the floor. Despite her simple digs, she felt like “the richest woman alive. I wasn’t playing by everybody else’s rules in a town that was run by all of my ex-boyfriend’s peers anymore.”

A new lease on life

Motivated by her experience with burnout and the subsequent two years she spent healing, Emilie set out to help other women find sustainable jobs they loved. When she wasn’t doing her new day job of ad buying for political campaigns, she was reading everything she could get her hands on about the psychology of behavior change, happiness, habit formation and how gender intersects with it all. She stopped hitting up happy hour with her politico colleagues to focus on her own personal growth and self-care. “I felt like I had just survived something and I wasn’t going to waste any more time. I had to get busy living.”

After saving up some money, Emilie quit her job and started Bossed Up. However, she quickly realized she couldn’t afford to be self-employed yet — “I should have started it as a side hustle instead” — and worked in online advertising for political campaigns for two more years. In 2015, she tried going full-time on Bossed Up again, and this time it worked.

Bossed Up 2.0

When Emilie first launched Bossed Up in 2013, she offered weekend boot camps “for women who think, ‘I don’t really know what I want but I can’t pretend to want this any longer.’” Participants work on clarifying their career vision, aligning work with their personal lives and strengthening their negotiation and communication skills.

Since rebooting in 2015, Emilie has added multiple services to Bossed Up. On top of boot camps, she hosts the Bossed Up podcast, does speaking engagements and workshops all over the U.S. and is promoting her new book, “Bossed Up: A Grown Woman’s Guide for Getting Your Sh*t Together,” which she wrote by hiding out for two weeks at her in-laws’ farm.

“We can’t adapt our ambitions to the BS the world tells us about ourselves.”

When I asked Emilie what she’s most excited about right now, she said it’s that people are thinking about their careers as multiple acts. She’d also like to see more women pursuing what they want without feeling like they have to prove themselves first. “I want women to feel entitled to pursue the kind of careers they would love,” she said. “Despite living in an unjust world, we can’t allow our ambitions to adapt to the BS the world sometimes tells us about ourselves. While power and privilege are a part of it, for sure, I don’t want women to edit their own ambition preemptively.”

She’d also love to see women focusing on what is most important to them at work, instead of giving 100 percent to every task they’re asked to do. “Give 80 or 85 percent to things you don’t care about, if you must. Only give 100 percent towards what’s most important to you, even if it’s not urgent to anyone else. You’d be surprised how few folks might notice.”

One of Emilie’s favorite Bossed Up podcast episodes is the first one she recorded, “To lead or be liked,” in which she discusses leadership characteristics with former Harvard Business Review editor Sarah Green Carmichael. It turns out that women outperform men on most leadership characteristics, except one — having a clear vision. Emilie feels like women don’t feel entitled to have a vision, sort of like we often don’t feel entitled to give advice. “I want women to have more audacity. It’s like a muscle; you can develop it with practice.”

“Living the life I want to live, not reacting to life as it comes at me”

With all that’s on her plate, I asked Emilie how she gets everything done. Her tenets are delegating tasks that aren’t her strong suits (“I give myself permission to be bad at some things so I can be good at others.”) and blocking off office hours for herself (“This is when I actually do the work.”). She reserves mornings for creative work (i.e., no meetings!) because that’s when she’s most productive.

Emilie spends time outside to decompress. She walks her dog at a big park near her home every morning, and she and her husband hike and ski on weekends. This year, she’s committed to being outside more without her phone.

In terms of work-life balance, she said she feels like she’s doing well. The life tracker planner she developed helps her, too. “That thing keeps me on top of my shit. Anything that forces me to plan and set personal and professional goals makes me feel like I’m living the life I want to live, not reacting to life as it comes at me.”

“A no-bullshit guide for whatever you want to do next”

With her book coming out in May, I asked Emilie what she wants The Juggle readers to know about it. She says it’s a data-driven, “no-bullshit guide for whatever you want to do next.” It’s full of stories of women from all walks of life who have taken control over their careers.

Her goal is to give women the tools they need to get what they want, without telling them what exactly that should be. She says, “This book should help accelerate people toward whatever they do next, which could include quitting your prestigious law career to become a mechanic, taking time off to work on yourself and your wellbeing or landing a promotion and raise.”

Meet Emilie

What struck me most about meeting Emilie in person (aside from the fact that she agreed to it in the first place and spent three hours eating, drinking and talking with me) was how confident and unapologetic she was. She never once hesitated when she answered a question and didn’t qualify her statements with the crutches I so often use, like, “Now this is just my opinion, but…” or, “I could be wrong, but…” It was refreshing and affirming to meet a woman who isn’t uncomfortable saying what she thinks and knows. It made me want to do the same.

Interested in meeting Emilie? This year, Bossed Up Bootcamps are happening in New York, Chicago, Washington D.C. and Los Angeles. Tour dates for her book are TBD, but get on her email list at bossedup.org or follow her on Twitter and Instagram at @emiliearies to find out more.

Emilie’s book recommendations


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