balancing multiple businesses

#BOOKEDANDBUSY: How Women Entrepreneurs Balance Multiple Businesses and Personal Lives

As women entrepreneurs, we all hit this age where half of us are mothers, half of us are single fine aunties with ambiguous love lives and yet, there’s always a conversation on how we can possibly lead dope lives offline and run multiple businesses at the same time. What happens when you actually run more than one business? People eat up all of the #bookedandbusy posts feening for your secret recipe so they can somehow find order within their lives. Think about how many “share the prayer, sis” posts we see about Ciara and Russell. It’s not a prayer, we’re all looking for, it’s a taste of her secret sauce.

Unless your best friend is also a popular entrepreneur, these secret sauce conversations turn into secret societies. No one wants to speak on how they haven’t washed their hair in God knows how long or how their husband automatically goes to Chiptole on the way home everyday because he knows you don’t plan on tearing yourself away from your computer long enough to actually make a meal.

Regardless of what hashtag you use, if you identify with being a #mompreneur or a single, fine auntie, being #bookedandbusy is the new wave. Having multiple ventures and side hustles is popular and almost vital in 2019 and beyond to keep yourself financially secure. It’s cute to watch Instagram stories of jet-setting entrepreneurs book flights from city to city and gain clients but what we rarely see is the insight behind handling more than one business at a time.

Three savvy women entrepreneurs: Jasmine Katrina, Victoria Jackson and Gabrielle Hickmon, all have multiple ventures, very transparent personalities and yet also happen to keep bomb hair and poppin’ social lives. We asked all three questions about their own personal secret sauce that you want to know but may not feel comfortable asking. Equally as important as their happy hour schedule is the very last question we asked each of them: How do they redefine their relationship with hustling?

Gabrielle Hickmon

Gabrielle Hickmon is a model for Black girls who live on the road. Gabrielle Hickmon is a writer, creative director, and strategist. ‘sunny’ is her first book.

What are your favorite tools and resources that help you keep everything in order?

Airtable, Google Docs, Scrivener, Mailchimp, multiple Moleskine journals and a Productivity Planner.

Do you follow traditional business advice with handling three businesses, like mapping out strict schedules and rules for each one?

I have at different points in my journey. I try to work on certain projects on certain days to keep a rhythm and also ensure I’m not getting completely bogged down in one and ignoring another. But, it always happens that you’ll make a ton of progress in one area and then not so much in another. That’s just how life is.

I’m learning to be less rigid and give myself space to explore. That’s also reorienting my priorities so, one business might be getting a bit more love right now. I’ve realized that sometimes there has to be an order to things and doing big picture goals might make it easier to deliver on other dreams later on. So, I’ve been taking steps back to think about the big picture and what helps me get there. That kind of work can’t follow a strict schedule or set of rules.

How do you distinguish the target audiences for each brand? Or does it seem like they naturally mesh together?

My target audience is like a venn diagram. You’ve got traits and behaviors that distinguish each brand, but some core values (real, raw, and relatable) that align with Gabrielle the person that exist in that middle space and ensure continuity. I often feel like I’m all over the place in my work and branding because I do a lot and sometimes it feels like each project speaks to very different sides of myself and people as a result. It can be hard bringing all of myself to the forefront of my work, which is something I’m always striving to do.

I’m giving you snarky, sexy, sappy, sassy, shady, smarts, shy, and sometimes silence on different days or all in one. Each of those characteristics speak to different brands, but they are all adjectives I would use to describe myself. I want my brand to always have some sass and sex, but also be incredibly smart and make space for sappy. With EightyTwo NinetySix, a podcast I co-host, we have been really clear that our show is witty, smart, creative and fun because that is authentic and honest for us. The episodes feel like a creative therapy session — that’s not always going to speak to everyone that my brand speaks to. My personal writing, ‘sunny.,’ and freelance work can be any of those things and again, won’t always speak to the other two perfectly. I’m often trying to explore ideas and feelings that need more space or don’t fit quite right in my other brands through my personal writing projects.

And, I believe I get to be myself, whatever that looks like. I believe the world needs more women, especially Black women who show up and show off every side of themselves. That’s me. I’m learning to worry less about specifically targeting certain people. If I’m creating work that speaks to some side of me, it will speak to some side of someone else as well and I just hope they can take what they need and be blessed by it.

My target audience is myself.

“I believe the world needs more women, especially Black women who show up and show off every side of themselves.”

Have you found it easy to delegate or do you feel the need to have your hands on everything?

I hate being micromanaged so I make a conscious effort not to micromanage others. As long as I’m getting updates and can get questions answered as I have them, I’m perfectly happy to delegate. There’s nothing I feel I’m above doing, but as things grow when you’re the head of something, it’s helpful to be able to delegate to others you trust and know will get things done right. When everyone is on the same page about vision, voice, and then execution, it makes delegating easy. It’s just up to me to set that vision and voice. Execution — I’m flexible. My way isn’t always the best or most expeditious so, as long as it gets done and done well, I’m open and I’m happy. I want people to learn, grow, and for whatever experience they have with me to be useful. How can they if I’m doing everything?

Girl, we see you living on the gram! How do you make time for travel as you work on your brands?

I gamed the system by moving abroad. I’ve been traveling my entire life and on my own since 16, so it’s as natural to me as breathing. I work really hard when I’m not on trips so that when I am, I can put an OOO on and set a really clear boundary of, “I’m not working right now beyond, making sure to document and notate my experiences in case I want to do something with them later.” But, that’s also where having an amazing team and general support system comes in as well. I know the world won’t end if I’m in Marrakech or Bali for a week. Content can still get pushed out. Merch can still get shipped out. Pertinent emails can still be handled. I’m nothing without the people standing beside me.

Practically though, I just keep a flight booked. Experiencing the world is a priority for me, and I build my life around wherever I’m going next. It’s a priority for me so I move accordingly.

Do ever feel guilty taking time for yourself? How do you combat that feeling?

I used to really struggle with this and still feel pangs of guilt occasionally now, but much less than before. You have to do some living in order to have anything to write about or create from. I remind myself of that and I talk to my therapist. I’m in a season of taking my time and prioritizing myself without it being tied to a precise output. It’s jarring and uncomfortable at times because for most of my life, I’ve tied my understanding of myself and beliefs about why I’m worthy to my accomplishments and output. It got to be exhausting.

“You have to do some living in order to have anything to write about or create from.”

I’m combating the feeling by doing the work. My therapist tells me to nurture myself and just let myself explore. I’m feeling my way through that homework and finding my footing. I’m getting to know Gabrielle when she isn’t running at the speed of light and knee deep in the production of something. I’m slowing and shutting it down to just be for a sec. And when I’m comfortable with just being, and know myself without my resume being a justification for everything, then I’ll know I can ramp it back up again.

I’m giving myself space — space and grace to explore.

“You have to do some living in order to have anything to write about or create from.”

Victoria Jackson

Victoria Jackson is a Houston-based PR & marketing consultant. She’s also the founder of Reinvented Marketing, a creative marketing studio helping small business build remarkable brands. An advocate for self-care, positive thinking, and designing a life you love, she chronicles her story as a millennial creative navigating multiple businesses, brand building, and the beauty of life through her personal blog.

When she’s not working with clients or creating content for the web, you can find her brunching across Houston, binge watching Netflix originals, or planning a new vacation.

What are your favorite tools and resources that help you keep everything in order?

Trello is my #1 lifesaver. I use it to manage my internal business processes, client projects, campaigns, my day to day schedule, and even personal things like making my grocery lists. I use the Planner Pro app on my iPhone to save meetings, appointments, and important dates. To keep track of finances, I use Wave for accounting/bookkeeping, and I use the Mint app to track my personal bills.

What does your daily schedule look like?

I wake up in the morning around 6am, and I dedicate the first hour to self development. I pray, meditate, journal, set intentions, read my affirmations, and listen to something spiritual like T.D. Jakes and Abraham Hicks or something motivational like Eric Thomas.

Then, I start work around 8am until around 6pm. If I’m really busy, I’ll work later but I try to keep a “traditional” work schedule as much as I can. I’ll either work from home or go to a local coffee shop for the day.

I batch my days to maximize my time:

  • I use Mondays to get organized, do administrative tasks, and work on multiple businesses development.
  • Tuesday through Thursday is dedicated to client work and major tasks – the main things that need to get done that week.
  • On Fridays, I spend most of the day scheduling the next week’s content for both myself and my clients, including social media, email newsletters, campaigns etc. so they’re all ready to go for the next week.
  • On the weekends, I focus on passion projects or just take the day off and relax.

I’m still tweaking my daily schedule, but this is what’s working for me right now.

Let’s get a little personal, does running your businesses take time away from you being able to build relationships with others?

It’s hard sometimes because everyone doesn’t always understand what goes into growing your own businesses full-time. If I can’t hang out as much because I’m swamped with client work or I can’t take a trip because I have to pay my multiple businesses coach, some people take it personally.

There are benefits on the flip side though. In my previous relationship, he was super supportive, we brought our laptops to dates (lol), and we bonded over our mutual passion for multiple businesses. That’s why it’s important to me to build friendships and relationships with other entrepreneurs and people who just “get it.”

Do you think a personal brand is imperative to be successful within your other businesses?

I do think it’s extremely helpful to build your personal brand as a business owner. The barrier to entry for starting amultiple businesses is so low nowadays, your unique personality, expertise, and insight is what helps you stand out in the noisy, crowded marketplace, especially online. I think that’s why influencer marketing has taken over the advertising industry because people connect with other people, not products or services. People buy from who they like, so they have to know you.

I got my first freelance clients and other great opportunities from my “personal brand” and by sharing my knowledge on my social media platforms. It’s what’s allowed me to build my agency today.

Because I do run multiple businesses, they don’t all fit under my personal brand “umbrella” so I won’t say it’s absolutely necessary for everything I’m doing but, having an established audience and online identity will definitely help promote all that I do when it’s necessary.

You recently decided to take a huge step back on social media and mainly engage via your business pages, has it helped your productivity and growth offline?

Taking a break from my personal social media has been AMAZING for my productivity. I never realized how much time I wasted scrolling on Instagram and Twitter everyday. More importantly, I’m no longer distracted by what other people are doing, nor do I live life “for the gram anymore.” It feels great to go out, have fun, and not feel the need to put it on my IG story.

It’s also forced me to get out of my comfort zone and start taking in-person networking, local marketing, inbound marketing, and pitching way more seriously. I never want my business’s success to rely solely on social media because you don’t own it.

Does being offline still further your bottom line? If so, what tips do you have for business owners looking to spend less time online?

Being offline does still further my bottom line because I can focus more energy on building real life connections, getting out and finding my target clients instead of waiting for them to come to me, and leveraging my existing network and referrals. It’s easy to forget that people were building billion dollar multiple businesses before social media even existed. While I’ve gained lots of clients from platforms like Twitter and Instagram, it’s good to know it’s not my only option.

I won’t lie though, social media is still a huge source of lead generation, and I’ll definitely keep using it in the future, in addition to traditional marketing.

“It’s easy to forget that people were building billion dollar businesses before social media even existed. ”

My tips for business owners who want to spend less time online:
  • Streamline your processes for social media marketing. You can still have an active presence without it consuming your day by dedicating one day a week (or month) to planning and scheduling all of your social media posts and promotions in advance. Then limit your active engagement to a certain time limit.
  • Build an inbound marketing funnel for your business. Create evergreen content that can be found via search engine and optimize your website to convert visitors on its own. Think about how you can remove yourself from your business and still make it work.
  • Do what I did and delete your social media apps for a little while completely. It will force you to be creative, be proactive, and think smarter.
How are you redefining your relationship with hustling?

I’m redefining my relationship with hustling by focusing on what makes me happy, not what others are doing. I’m staying in my own lane, running my own race in my own time. Taking time away from my personal social media feeds helped me see I was being influenced by too many sources. I’m more confident now because I’m making decisions based on my own intuition rather than society’s standards.

Jasmine Smith

Jasmine Katrina is the Founder and CEO of Pure Communications & Company (Pure Comm. & Co.), a small boutique digital marketing and communications firm located in the Washington D.C., area. At Pure Comm, Jasmine works with small businesses, entrepreneurs on digital marketing, social media management and website development.

When she’s not working with client projects, she is blogging on life, career, style and faith at As a blogger, she uses her words to, as she says: inspire to empower women, connect to build with them. She pens her experiences of faith in all things style, career and life.

Do you feel like purpose and entrepreneurship are intertwined?

Not necessarily. I think if you’ve found your purpose and believe you know what God is calling you to do – you have to think about where he’s calling you to do that. While running my own business and blog, I also work full-time, and I love it. I get to reach more women in multiple spaces because I work full-time, blog and run a business. Purpose and entrepreneurship can be intertwined when you’re doing the work God has called you to do.

What are your favorite tools and resources that help you keep everything in order?

Truthfully, I love a physical planner. I write everything down in there first – then I move it over to my Google Calendar. I also use apps that allow me to keep a running list of ideas, notes, etc., like EverNote and Google Docs.

Have you learned any lessons in business that also played out in your personal life? How did you move forward?

Absolutely. I think the biggest lesson I’ve learned – and am still learning – is that it’s important to master a few things rather than juggle a lot. I would be so eager to land new clients that I’d overload myself with work to the point of mismanaging time, resources and money. It left me with frustrated clients, lack of sleep and beating myself up for not being “good enough” to handle everything. And that’s simply not true. I’m learning to say no to the short-term in order to make room for the things I want long-term.

“I’m learning to say no to the short-term in order to make room for the things I want long-term.”

Do you think you’ll always have more than one business going at the same time or is this short term for you?

I’m not sure what the future holds, but I love the balancing act that I currently have. My blog is important to me, as well as multiple businesses and full-time career. I don’t plan to limit myself to just one thing, but if that day comes, then I welcome it with open arms.

Did you launch them at the exact same time?

No. First, I launched my blog while in college, back in 2012/13. After college and in my first job right after, I launched my business in 2016.

When job hunting, do you feel like your multiple businesses are an addition to your resume or a possible hindrance?

It’s a definite addition! That’s why I love multiple businessess and full-time career. There are skills I’ve been able to develop that I can specifically apply into my full-time job. On the flip side, there are resources and issues I see that I can tailor my business content to be able to help with. It’s a beautiful blend of both and I make sure to include my business on my resume and bring it up as additional experience.

How are you redefining your relationship with hustling?

Ah, “hustling” gives me a love/hate feeling. I love the grit, grind and focus that I have when hustling. However, the fallacy of “no sleep until you’re dead” or other weird mantras like that perpetuate that all hustle with no rest is the key to success — and it’s not. It’s carving out time to rest, to hustle, to laugh, to be with friends and create a well-rounded life is the #majorkey.  

We would like to send a major “thank you” to Gabrielle, Victoria and Jasmine for sharing their thoughts with us! You can follow Gabrielle on Instagram and Twitter @gabbyhickmon, @thereignxy, @eighty2ninety6, Victoria is online @thecaptialV and @reinventedmarketing, Jasmine is also online @jkatrinasmith and @purecommco.

If any of their tips or insight stirred something within you, feel free to leave us a comment below so we can chat about it.


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2020 the bronze hustle