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Working Boldly: A Day in the Life of Devin Drake,
Executive Assistant & Project Manager

Written by: Audrey Fairbrother

You’ve probably heard of the amazing perks of remote work: Flexibility, freedom, work-life balance, and more.

While those sound incredibly enticing, what if I told you that remote work can be even better than the classic Instagram version?

At Boldly, it is! Because you can add to that list:

  • Stability…
  • W2 employment…
  • Energizing community…
  • Serious career…
  • Challenging, diverse work…

And that’s just scratching the surface.

It’s not about hunting for new clients, or signing up to a platform, filling out your profile and then waiting months to get a call, wondering “do they even know who I am?”

At Boldly, it’s different. It’s personal. No platforms or profiles here. A real job, with real people. Our model is the first of its kind: premium subscription staffing.

Hundreds of world-class clients like Apple, Grammarly, Zendesk, Facebook, and Asana subscribe to Boldly to work with Fortune 500-trained, hand-matched members of our team—people like Devin Drake.

Working Boldly with Devin Drake

In this series, we pull back the curtain so you can get a glimpse of the new way to work.

We spent some time with Devin to find out what a day in the life of an executive assistant, project manager, and military spouse advocate is really like!

(Plus get Devin’s Top 7 Tips for Remote Productivity!)

Meet Devin (and a Special Guest)

Devin Drake
Executive Assistant, Project Manager, and Military Spouse Advocate

Military Spouse, United States Marine Corps

Stationed, San Diego (off-base)


  • Webster University
    MBA, Administration and Management
  • University of South Carolina-Columbia
    BS, Human Services
  • John C Calhoun State Community College
    AA, Elementary Education and Teaching

Professional Experience: 12 years

Office Buddy: Pet Rabbit Chewy Bun-Bun

remote work benefits

A Day in Devin’s Life

To start, we asked Devin to give us the play-by-play of a normal day to see how her work integrates with her life.

5:00 a.m. Wake up and prep for an organized day.

5:30 a.m. Start working for my clients whose projects require lots of creativity. I do my best creative work early in the morning.

7:00 a.m. Get my son ready for school and drop him off.

8:15 a.m. Head to the gym. I do this every day — rain or shine — because I’m a big believer in health and wellness.

10 a.m. I typically go back to work at this time, but because of my job’s flexibility, I’m often able to have coffee with friends! This is something that never would have been possible before Boldly.

11 a.m. Continue working for my amazing clients. I do project management and administrative tasks that don’t require as much creativity.

1 p.m. Done working for the day! I have some time before I pick my son up to go for a swim, walk the dog, run to the grocery, or clean the house.

2:30 p.m. It’s time to pick up my son from school! This is the highlight of my day. He gets in my car sticky and excited, talking non stop about his day. We head home, do homework, then spend time together or he has friends over to play.

5:00 p.m. My husband will have just gotten home from work and we will make dinner together. After dinner, we will catch up on the TV shows we are watching. We really like Stranger Things, The Good Doctor, and 911.

8:30 p.m. We all head to bed to read and wind down. My book of choice is normally a good thriller with lots of twists and an unexpected ending.

9:00 p.m. It’s lights out time. I like to get 8-9 hours of sleep so that I start my mornings refreshed and energized.

Life as a Military Spouse

Beyond her extensive experience and education, one of the most interesting things about Devin’s story is her life as a military spouse.

Devin explained, “Military spouses, face lots of misconceptions. We have to fight stigmas around lacking education, experience, and marketable skill sets.”

These stereotypes couldn’t be further from the truth. Case-in-point, just look at Devin’s 12 years of professional experience, her MBA, and the adaptability that comes with living all over the world.

“Milsos bring a lot of worldly experience … Everywhere I’ve lived, I’ve learned to adapt to new cultures: Japan, China, Taiwan, and Hawaii — there’s just so much experience that comes with that!”

Plus, milsos have an uncanny knack for quickly forming warm relationships.

After all, as Devin says, “We’re moving every three years, so relationships are a revolving door. No one ever moves with you, and in the military, everyone is always moving. Even though I lived somewhere for three years, I didn’t have the same friends for three years. There is no stability or consistency.”

Not only does this help with colleague relationships, but it gives milsos like Devin an advantage in building client relationships; a key to our work at Boldly.

How Life has Changed

Since coming aboard at Boldly, though, things have changed.

For starters, even with a fully distributed team, her sense of community has never felt more stable.

“Your vibe attracts your tribe,” says Devin. “Everyone at Boldly has the same vibe; we care about working with great people who build you up. And our relationships are closer than when I worked in an office 40 hours per week!”

This tight-knit camaraderie is amazing for productivity, feeling supported, and never feeling isolated. It’s also key to feeling comfortable enough to set clear working hours and finally maximize her work-life balance.

“Before when I was working 40 hours per week, here’s what my life looked like. Get up, drop my kid off at school, get him at 5 o’clock, and then spend a few hours of chaos where no one wants to talk to anybody,” she explained. “So, when we moved to San Diego I felt like I didn’t know him. He spent most of his time away from me.”

Today, though, her life looks much different.

“Now, I’m totally available for him. I volunteer at his school and have four different roles. This is something I never could do before.”

What’s Working as a Remote Executive Assistant and Project Manager Actually Like?

Next, we wanted to know what the work as a multi-talented executive assistant and project manager is actually like.

What’s most dazzling is the sheer variety of what Devin gets to do.

On an average day, she might move from content marketing work, like copywriting, blogging, and managing YouTube channels, to managing projects for interior designers in the Hamptons.

This includes everything from administrative tasks and expense management to communication and process creation.

“I feel like I’m getting as much out of it as they are. They teach me something they know how to do, then we document every process, and I’ve been able to get really good at it,” Devin says.

Plus, being able to completely set her own schedule allows her to work at optimal times for her focus and productivity. The standard 9-to-5 working day is dead at Boldly, and this allows her to get more done in work and in her life.

Plus, her officemates aren’t too bad: “Pretty much the first hour of my workday is spent with my bunny jumping on my lap and then on to the desk with me putting him back down. Over and over and over until he gets breakfast!”


The work is challenging, valuable, and can even be a little quirky at times.

Devin shared a story about her marketing work, when she was working on a niche blog post for a client.

“Last December, I was working on a ‘Stopping Overeating’ blog post for a client when the doorbell rang. It was a delivery for a package from my mom and grandmother filled with homemade goodies.

“I took a quick lunch break and binged on homemade Christmas goodies and then went back to my blog post thinking about the irony of how I had just had brownies, cookies, and fudge for lunch while writing a motivational piece on cutting flour and sugar from your diet.”

Some things happen #OnlyAtBoldly!

7 Productivity Tips for Working Boldly

remote work office

Finally, we asked Devin her best productivity tips and hacks for working Boldly—and she didn’t disappoint! Here are her seven top productivity tips for remote work:

  1. Set up a comfortable and efficient working environment. For me, that means having a quiet space with good lighting, dual monitors, and a clear desktop without any distractions. I even leave my phone in another room so I am not interrupted by texts or social media notifications.
  2. Be organized to produce at a higher level. It only takes a few extra minutes to create an organized system to track and plan your time. If you don’t know what you have done and what you are going to do, then you waste time deciding what to do in the moment.
  3. Working remotely is not about having the flexibility to work anywhere at any time, but about having the flexibility to work anywhere when I need to. Working on a laptop at a coffee shop in between a doctor’s appointment is great. Working there every day is inefficient.
  4. Communication in your everyday life is important. When you work remotely, its importance magnifies. It is so easy to misinterpret a written message. Take the time to respond to messages, ask for clarification, and confirm your understanding.
  5. Always choose a video conference over a phone call. When you can see a person’s face, you can read body language. This creates a connection a phone call could never achieve.
  6. Utilize your productivity and communication tools. There are so many of them out there, from Zoom to Asana to Lastpass; the list goes on. These online tools will help you work more productively by improving your communication and task management.
  7. Always be kind. When we think of productivity we often think of technology and tools that help us produce at our best. The way you treat others paves the way for these tools to work. It doesn’t matter how skilled you are at your job, if you aren’t kind, your attitude will cloud your success.

Working Boldly One Surprising Day at a Time

Life at Boldly is fast-paced and challenging because we work for the best founders, executives, and companies in the world.

This is precisely why we hire amazing people like Devin. Her clients call her, “A total life-saver!” and they mean it.

Every day, she gets to work, parent, and live at the top of her game.

In our book, that’s what working Boldly is all about.

Topic: Remote Executive Assistant

Updated on December 19th, 2022

About the author: Audrey Fairbrother is the Marketing Manager here at Boldly, when she's not spreading information about the benefits and joys of a premium remote team, she enjoys drinking a good coffee or going for a run in her hometown of Denver, CO.