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Balancing in the Air: Days in the Lives of Female Entrepreneurs

Learn how other entrepreneurs manage this delicate balancing act.

Entrepreneurship is a lot like running around a hospital, going from case to case and caring for patients. Or maybe it’s more like a tricky circus act where you’re suspended high off the ground. Whatever metaphor you prefer, there’s no denying that running your own business can be overwhelming or frantic. We’re continuing our series on the days in the lives of female entrepreneurs. Read on to hear about how they streamline their work lives and manage their teams every day.

And if you missed Part One, be sure to check it out here!

Lauren Eskin, Owner, Brand Strategist and Designer, LoLa Design Co.

My typical day:

I wake up at 7:30 a.m. and take my dog Lincoln out before sitting down for my morning coffee and getting ready for the day. Until 9 a.m., I take it slow, reading through emails and creating my to-do list of big projects and small to-dos. I always break my to-do list down into three lists: things to do myself, things to assign to my team and things that can wait until another day.

From 9 to 11 a.m., I do a lot of administrative work (answering emails, taking meetings, communicating with my team, managing print orders and working on business development).

Around lunchtime, I eat something and always take Lincoln for an hour-long walk somewhere around the city, sometimes with a friend that works nearby and her dog too. This really breaks up my day and gets me in a creative headspace for the afternoon.

After this break, I do my creative work. This is when I’m designing brands, developing websites, creating content and working on bigger ongoing projects.

Towards the end of the afternoon, I check in on my progress and my team’s progress and compare it with the to-do list I created for the day. I take note of what’s on schedule and what we need to create more time for and start creating the following day’s to-do list. I always spend an hour or so at the end of the day responding to clients’ emails and preparing progress reports to stay on top of our biggest accounts.

At least twice a week, I like to do something to wind down after the workday like happy hour, going to the city dog parks or Trivia Night at a local spot with some friends. This gives me something to look forward to at the end of the workday!

My best time management advice:

  • Time block! It’s nearly impossible to mix creative and administrative work and still be productive. I like to split up my day, and then create mini to-do lists for each block.
  • If you’re like me, you’ll just work through the day from start to finish if you don’t schedule breaks. My hour walking outside with my dog and a friend is built into my schedule just like a meeting or project, and this means it’s something I make time for, not find time for.
  • Fit in the “big things” first, and build the small stuff around that. If you place too much importance on the small stuff, you’ll never find time for the big stuff.

Michelle Orrantia, Founder, Ollie Jay Official

As a small business owner with two small children, my day starts at 6 a.m. I prepare my kids for school and drop them off by 7:30 a.m. By 8 a.m, I’m in my office, a townhouse I own three blocks from my actual home where I keep my inventory and have a room upstairs for the kids.

I founded a children’s clothing brand that’s designed in-house, and all of our inventory is stored in our office/townhouse, so the first thing I do when I get in the office is package any orders from the weekend or the day before to get them ready for the USPS pickup. I always schedule a pickup the day before to save me time driving to the post office. It’s a free service and only takes about 30 seconds to request the pickup!

Once that’s completed, I’ll start planning special tasks for the day depending on the day or the month. Typically my first tasks involve social media strategy, content creation, customer service  and responding to emails. I also do a lot of design, and I collaborate with other artists to license their patterns, so I dedicate time each week to seek out new and talented artists to work with. Once I’ve selected my final prints for the season, I’ll start developing the product lines for those prints and ordering samples from my manufacturer. When I have the samples in hand, I’ll schedule photography and start collecting pre-orders by sending line sheets, attending markets and using online platforms like Faire.

In the weeks that I have a collection launching directly to consumers, I plan the marketing strategy, including updating the website graphics, creating email blasts, updating my private Facebook group and scheduling social media content. This way, I can show my consumers what products are launching, when, at what time and what the cost is. I’ve found this helps them plan their orders and it makes my launch day more successful!

At the end of each week, I’ll review my inventory levels to make sure what I have on hand matches what I have listed on my platforms and adjust as needed, or restock popular items.

It sounds like a lot, but typically I’m in the office by 8 a.m. and out by 2 or 3 p.m. However, if we have inventory incoming that we need to sort—which is typically once a month—I may end up staying until 5 p.m. for a few days to make sure everything is organized.

Megan Kitt, Founder, Tuli

I’ve tailored a non-traditional workday that’s perfect for my lifestyle. I get up around 5 a.m. to drink coffee, read the news, exercise and have some time to myself before my young kids wake up. After making breakfast and getting everyone ready for the day, my nanny arrives at 8 a.m. I kiss them goodbye and start the long commute down the hall to my in-home office.

I work until 2 p.m. and then have the afternoon open with the kids. We’ll hit the beach, go for a hike or just hang out at home. Often, I have afternoon photoshoots for Tuli’s fashion campaigns, and I’ll bring the kids along to help. My daughter loves telling the models how to pose (her go-to is “twirl around!”) and I babywear my son while shooting. It’s important for me to model for them working hard toward a dream, and I love having the flexibility to include them in my work in this way.

After that, we make dinner together, and then it’s time for baths, books and bedtime. My husband is often deployed, so after the kids are asleep by 7:30 or 8 p.m., I’ll return to my office to get a few more hours of work in. Doing that allows me to take Thursdays and Fridays totally off (minus working during nap time!) to spend all day with my kids and friends or pursue hobbies.

With a team working remotely around the world, everyone is able to fit in hours at the times that work best for us. For me, that affords tons of time with my kids without sacrificing my career aspirations. It’s not perfect and can be stressful, but I wouldn’t trade it for a traditional work schedule.

My best advice is to set specific work hours. I didn’t do this prior to becoming a mom, but I’ve learned that you work much more efficiently when you have no choice but to get as much done as you can during a small window of time. It’s easy as an entrepreneur to default to working all the time, but my company is actually more successful now than it was when I worked during every spare moment. For now, those work windows exist out of necessity, but I wish I’d set similar boundaries for myself pre-kids!

Zoe Thomson, Co-founder and CIO, LUCID

A typical day in my life usually goes as follows:

I like to have a flexible sleep-wake schedule that changes with the seasons, so now that we’re getting sun earlier, I rise earlier as well

Before the day starts coming at me, I always give myself a solid block of time in the morning. I keep this time flexible to engage in whatever practices feel right—I’ll read, go for a walk, practice meditation, whatever I feel will help me enter the day feeling at ease, energized and excited about life. (Typically this time plays double-duty as I multitask by also caffeinating heavily, to be honest.)

Each morning I like to make a list of the top three things that I want to achieve that day. Not the top 10, not the top 100, the top three. I try to really stick to it. When there’s a lot on your plate, I think it’s all too easy to become distracted or overwhelmed by all the minute tasks that really aren’t so important in the grand scheme. By narrowing it down, I ensure that every day I’m asking myself the question of what’s really going to move the needle and I’m better able to avoid losing focus

Once I’m ready to tackle the day, I like to start my work days off with more cognitively intensive tasks, then move into the simpler tasks that just need to get done later in the day. That way I’m always putting my best energy toward the tasks that really count

My days typically contain a fair few meetings across several time zones, so the structure of my days is pretty variable. That said, I always, always, always make the time to get outside during the day, rain or shine. I think it’s important to recognize what energizes you and actively make space to do those things. The way I see it, it’s always worth prioritizing the things I need to do to show up as my best, even if that means showing up a bit sweaty to my afternoon meetings after a lunchtime run!

This might be an unpopular opinion, but once the workday is over I do my best to really unplug (there’s no answering emails from my phone in bed happening in this house). When I’m working, I’m working, and when I’m not working, I’m not working (or at least really trying not to). I’d rather give my mind the time and space to percolate in the evening so I can come to the next day with fresh energy and fresh ideas.

That said, when you’re committed to your work, sometimes things come up that just need to be done. I’m no stranger to a 10 p.m. meeting, or staying up until the wee hours prepping for a presentation the next day. In this line of work you need to be flexible, but for me, having a baseline routine that includes time to recharge and shake off whatever happened that day is important.

In the evenings I like to see loved ones, get some exercise in or spend some solo time practicing hobbies (I’m currently learning to DJ). When you’re working on a passion project, work can so easily become your whole life, but for me, it’s important to nourish other aspects of life too.

Christine Whitmarsh, President, The Ink Agency LLC

Typically I wake up around 7 a.m. and indulge the dog in her morning sniffing of every last rock, piece of dirt and shrub in our neighborhood. After that, once everyone has been fed and watered, I grab coffee in my “World’s Best Boss” (of myself) mug and head to my desk to lay out the day’s schedule and tasks.

Much of the “work grid” I’ve created to organize my day comes from my early, brief career as a hospital RN BSN. As it turns out, managing 10 orthopedic patients and running a creative agency are pretty similar endeavors! Regular tasks include my email/social media rounds (like medication rounds), creating at least one piece of new content daily and ideally, completing one business building and website SEO task daily.

Habits are a big part of my life. My biggest work habit is time boxing: assigning tasks to blocks of time to ensure they get done. That’s also my number one time management tip. Rather than hoping, wishing and praying for things to get done, assign them blocks of time in which to complete them. This also cuts down on wasted internet time, as “mindlessly scrolling social media” is not something people intentionally schedule.

My other habits! Well, there’s my daily 10-20 minute meditation around 5 p.m. to create a line of demarcation between work and life. And speaking of life… outside of writing books for influential people and coaching memoir authors, I am an aerialist. The short version of the story is, about five years ago, I was bored by going to the gym, so I didn’t go. So, in order to get in shape, I literally had to turn myself into an athlete—an aerialist. Think Cirque Du Soleil but done by a 49-year-old ghostwriter with a titanium rod in her back. So a few times a week, a key item on my work grid involves things like aerial private lessons and conditioning training.

Therefore, how I “stay on top of it all” has a lot to do with staying in the air… on top of a steel hoop!

About the author

Laura Grant

As Managing Editor of Lioness, Laura Grant works with the editorial team and a slew of freelancers and regular contributors to produce a publication that offers equal parts inspiration and information. Laura is a graduate of Western New England University with a bachelor’s degree in English Literature and a master's degree in Communications. She spent her undergraduate term developing her writing and communication skills through internships, tutoring and student media involvement. Her goal is to publish a novel one day. Before joining Lioness full-time, Laura was a freelancer herself and wrote many stories for the magazine.

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