Women Who Work: Creative Business Support, Jess Cook

Jessica Cook helps small business owners focus on the heart and soul of their businesses. She has run her own successful business for four years, and has worked with other small business owners to to help their businesses grow and thrive. She’s the problem solver you may need on your side!

How did you make the leap to your current role?
I have been working with creative business owners for over four years now; when I started I worked as a Virtual Assistant, performing administrative tasks and some content writing. I eventually grew my skills to the point where I was serving my clients by creating their entire content for them, managing all their projects and teams, and helping with strategy brainstorming sessions and consulting. So I upgraded my role to take on these larger scale duties and I have since then also taken on new clients.

When you were a kid, what did you want to be when you grew up?
A Muppeteer. I still very much believe in the Muppet philosophy and am a huge Muppet fanatic.

What was your first job ever? Did it help you in your current role?
My first professional career was working as a high school teacher. I actually have two graduate degrees in Education, and I use that knowledge and experience all the time in my current role as I help my clients create educational content like blog posts, newsletters, ebooks and online courses.

What made you want to start your business? What or who inspired you to do so?
I have been able to work with several amazing creative business owners over the past four years, and my favorite part of my client work has been consulting with my clients to help them plan their next big project or map out their goals. I also have just always loved to teach, so I decided to start a website where I could put my teaching skills and experience to work for more creative business owners, because I can only work 1:1 with a few people.

My clients are the ones who inspire me – they are all working so hard to put amazing things out into the world. I think the world needs more amazing things, and it’s a privilege for me to be able to help them do their work.

What does your job entail? How do you explain what you do to others?
Task-wise, I do a lot of different things, including proofreading, creating original content for blogs and emails, managing people and projects, and consulting/brainstorming. I think the most important thing I do for my clients, though, is to let them know that they’re not in this alone. They have someone in their corner (me), and I’m always cheering for them and supporting them as they grow their empires; I’ve always got their back.

I like to tell people that I’m the Spock to your Kirk, the Hermione to your Harry, the Tyrion to your Daenerys, the Leo to your Bartlet.

What is a day for you like? What is your routine?
Right now that’s a bit all over the place, because I’ve been home-schooling my three kids, and it’s summer so they’re all home, every day. In general, though, I get up and start working pretty early (by 7:00 AM). I start with the projects that help me move my own business forward (like professional development, taking online classes, reading books, and working on my website or creating my content), because that way I can prioritize my own goals and growth. Then I start in on my client work, which is usually a few hours each day. I try really hard to batch my client work so that they don’t lose any time to context switching from project to project, so I’ll “log in” for one particular client and keep working until my work for her is done, and then sign off for her and log in for another client. I keep doing that until I’ve finished everyone’s work for the day.

My plan for the coming months is to be working while my kids are in school (they’re going back to public school in August), and to be able to be finished for the day by the time they come home.

How do you end your work day?
Generally I just double-check my planner to make sure I’ve done everything I needed to do for the day. If I have extra time in my day, I’ll add on a few more tasks from my own business goals list, to get further ahead on those projects. Other times I have to stop early because one of the kids has an appointment, or something like that. So it’s a little bit different each day.

How did you go about starting your business? What were some of your initial steps that you took?
I started by building my website and starting my e-mail list, so that I’d have an outlet for open communication with people who might become clients down the road, or who weren’t in a place to hire me for 1:1 work right now but could still benefit from my help. I’m still very much in the early stages, so right now my goal is to get consistent with posting to my blog, sending emails once a week to my subscribers, and posting consistently on Facebook and Instagram.

I’m doing that because I know that I won’t be able to sell anything (like digital downloads or online courses) if I don’t have an engaged audience to sell to, so that’s where I need to start.

What are you biggest responsibilities as an entrepreneur?
I have built up a really strong rapport with all of my clients, to the point where they trust me to do my job and they rarely double-check my work. This means that I’m responsible for making sure that their message gets out into the world and looks polished and professional, and goes through without any glitches. It’s a responsibility, yes, but it’s also a privilege to be trusted with some of the operations of these amazing businesses.

What has been the hardest part of your transition?
Right now I’m struggling to grow my email list. I feel like when I talk to people 1:1 in a consulting session, or give them feedback in a Facebook group, they always tell me how much they appreciate my advice. But somehow it’s hard to translate that to a digital interaction – to convey that helpfulness on my website and get it in front of people who need my help so that I can get them on my list. That’s why I’m working on posting consistently, so I can have a solid foundation of content to use to make my connections on these other platforms.

What has been the easiest part of your transition?
Coming up with things to write about comes really easily to me – I know this is an area where a lot of business owners struggle, but for me I’ve got a whole list of ideas to write about in the future. So that’s the good part about my current goal – it won’t be any problem for me to come up with the content that I want to post; it’s finding the time to put it all out there that’s harder.

What keeps you motivated?
It’s easy to stay motivated when you work with amazing people. Seeing the cool stuff my clients come up with makes me want to work harder to make sure that more people have access to that stuff, and that I’m doing everything I can to help them run and grow their businesses.

On the personal side, I’m very motivated by my family – I want to not only provide for our actual needs but be able to pay for fun things (like a vacation) with my income.

How do you define success now?
I feel I’m successful because:
- I’m doing a job I really love, and I get to put my talents to work every day. My husband hates Mondays but I look forward to them because I can hit the ground running on my own goals and my clients’ goals.
- I work from home, and I get to map out a schedule that allows me to be there for my kids when they need me. (Though a component of this is that I’d like to grow my side hustle to the point where I can take more time off from working to be with them.)
- I’m able to cover my expenses for the business and provide for some of my family’s needs.
Of course I have goals to grow this thing to the point where I have even MORE success, but for now I’m really happy with the progress I’ve made.

How do you prevent burn out?
Derek Sivers says that if you hear about a new opportunity and you don’t immediately think, “Hell yes!” then you need to turn it down. I really struggle with this because I’m tempted to say yes to every paying gig just because I want to feel financially secure, but I have had too many experiences in the past where I started working with a client and it wasn’t a good fit, so I started to dread the work (and then of course I wasn’t giving that client my best, either). So I try to remind myself to look for more “hell yes!” opportunities, and to let go of anything that doesn’t make me feel that level of enthusiasm, because if I get burned out it’s no good for me OR for my clients. I’m still working on that one, though – it’s definitely easier said than done.

What do you think is the most important characteristic to have for someone who wants to take a similar career route to yours?
Always look for opportunities to learn new things. The absolute most valuable skill you can have in a service-based position (whether you’re working as a VA or a consultant, a content manager or a coach), is to always learn new things and then apply those skills to the work you do with other people. I have a lot of confidence in myself as a learner, and that has really helped me in this job because if someone asks me if I can do something, I almost always say YES. Even if I don’t know how to do that thing right now, I know I can research it, figure it out, and teach myself how to do it. Every minute that I spend learning new skills to help my own business, I can also put those skills to work for my clients, so it’s a win-win.

What do you wish you knew before starting out on your own path?
I wish I knew that it would be hard to defend this whole freelance thing to other people. I think, after the past 7+ years of me working in some freelance capacity or another, my husband is finally comfortable with it. But it has taken a while! He just has a hard time seeing past the traditional idea of what a career should look like, and he’s definitely not the only one. It’s hard to have confidence in yourself and set really big goals when the people around you don’t even realize those big goals are possible.

Did anyone help you in developing your own business?
Oh yes! My clients (here I go again, but it’s so true)! They refer me to their friends who own businesses, and connect me with new opportunities all the time. As much as I support them, they definitely return the favor.

Do you have a work idol? Is there a working woman or man out there that you admire?
Jim Henson and Walt Disney (it’s a tie). I love how they built careers out of such intense creativity, and a desire to bring joy and whimsy to people’s lives.

What is your favorite thing about the industry you work in?
I love being able to “talk shop” with other creative people. It’s great when the people you work with not only understand your business, but also your hobbies. The fact that I’m a knitter, spinner, crocheter, quilter, and sewist is actually a huge asset in my career, because it means I’m well-versed in those languages and can help people building businesses in those industries. I have met so many amazing people in my life just because we all love yarn (or fabric), and that’s really cool.

What are some tools that you can’t live without?
1. I always have to have a paper planner. It’s how I keep track of my appointments, goals, To Do lists, and even the hours I work for my clients. Right now I’m using the Passion Planner, and it’s pretty good, but I think next year I’m actually going to create an Agendio planner for myself because I want to really be able to customize my planner for exactly what I need.
2. I love Asana for communicating with my clients about our projects and making sure everyone on the team knows what they need to be working on. Plus it’s free, which is really awesome! I’ve used several different project management apps and this is by far my favorite.
3. I couldn’t live without email marketing software in my own business (or my clients’ businesses since I help all of them with their emails in some way). Right now I’m using MailerLite for my business because it’s the best free option I’ve found, and I also really love Active Campaign for anyone who wants to pay for a more robust option.
4. I’m also just a huge fan of fancy notebooks, because I like to keep all my notes from the online classes I take in a notebook (I write all that stuff out by hand, it really helps me with my thought process).
5. Dropbox is a life-saver for me. I use it to store all my own important files and to share files with all of my clients. I pay $9.99/month for a TB of storage because I have a lot of shared files, but you can use it on a free plan.
6. I also love Google Drive, which is free and awesome. I love the comments feature for when I want to go back and forth with a client while we craft a piece of content together or plan out a project.

What do you have on your desk or working space right now?
I always have my laptop, my planner, my study notebook, and a variety of pens and pencils. Usually there’s also a water bottle and probably the bracelets I took off while I was working because it bugs me to wear them when I type. Right now my desk is a little messier than usual so it also has some bills on it, the latest issue of a magazine I work for, my most recent sewing project and a pair of socks I’m knitting.

What do you want other women in similar situations to know about your chosen career path?
It is totally possible to build a business using your talents and your own personal weirdness. You can carve out a career for yourself doing the things that you really love to do – I always tell people that mindsight is way more than half the battle. If you believe you can do it, you’ll find a way. Conversely, if you don’t believe it’s possible, you’ll find excuses not to make it happen. Sometimes I get a little bossy (ahem), so I would *like* to tell people to suck it up, put on your big girl pants, and get to work. You can keep hanging onto your excuses or you can get to work finding opportunities – it’s up to you.

Any last thoughts?
I feel like a lot of creative business owners think they can’t afford to hire someone to help in their business, and sometimes that just isn’t true at all. The thing is, yes – there’s a cost to hiring someone. But what you gain in terms of time to grow your business and focus YOUR efforts on your most effective tasks is priceless. So if you’re feeling like you can’t afford to hire someone or you’re completely overwhelmed and don’t even know where to start looking for help, shoot me a message. I’ll help you sort it out and figure out what’s possible. You don’t have to have a six-figure business to get some help!

Look for Jess Cook on her website! Follow her on Instagram, Twitter, and Facebook.