Creative Insights: Jennifer Hail

Creative Insights, Freelance, Jennifer Hail

You guys, I’m SO excited Creative Insights is back this week after taking a short break last week. This week I’m happy to have Jennifer Hail answering my questions about her creative journey so far. I stumbled upon her portfolio a little while back and instantly fell in love with her work. Her creative style is clean, timeless, and absolutely beautiful. Plus her calligraphy skills are on point. Be prepared to fall into a soothing, eye candy interview with some really amazing advice and a look into her daily life. 


Tell us a little bit about your business and what it means to you

I recently finished my BFA in design over winter break, so I’m just now devoting solid time and planning to start my freelance design business, Pine. This is the fun part–being able to map out exactly what my dream job looks like, figuring out how I can offer those services to clients, and how I want to present my business to the world. I want Pine to be a studio that partners with passionate creatives, whether they only have an idea, or are already making something amazing, and helps them make their vision a reality through art direction, photography, branding, and crafting a beautiful web presence. To me, this means living each day doing something that I love, even when I have to do the hard work that isn’t so fun.


What is one daily ritual you can’t live without?

Although I can live without it, I absolutely love making a pourover coffee every morning. I use a kitchen scale to measure 21 grams of beans, drop them into my grinder, and fill my electric kettle up with filtered water. When everything is ready to go, I start the timer on my iPhone and slowly pour the hot water in circles until I’ve reached 350 grams. It’s a precise process that I learned while I was a barista at my local coffee shop (I’ll mention that later), but I find it so calming.

When you’re not creating where can we find you?

You can find me reading articles about running a business, playing with my fluffy white cat, Theodore, or spending time with my boyfriend.


What do you struggle with most when it comes to running your own business?

I struggle the most with the transition from college to dictating my own schedule and sticking to it. I have never been a morning person, but I truly hope to change that this year. There are so many benefits to getting started earlier in the day, and I think this is the key to maintaining a regular schedule. The article Meagen linked to has a lot of great ideas that I’m going to start implementing.

What’s one business goal you hope to achieve in 2015?

Since I am just starting a real, registered with the state, tax-paying business, I have a ton of goals, but I don’t want to put a huge amount of pressure on myself to achieve everything I have set out to do. I know that freelancing usually starts out as a side business for most people, so I want to focus on laying a solid foundation and slowly growing the number of projects I work on and the income I’m generating. I currently have one freelance client, so working with more people would be a blessing.


How do you treat yourself?

I indulge in my all-time-favorite ice cream: Graeter’s Chocolate Chip Cookie Dough. Their excellent vanilla ice cream is the key to everything, and I have seriously considered serving it at my future wedding.

Any tips for staying organized? Do you have any project management tools you can’t live without?

Staying organized is one of my favorite things, so I use and love these tools every day.

Password is an app that I don’t know how I ever lived without. It stores all of my passwords into vaults and helps me generate hard-to-break new ones. Luckily, I was able to snag the iPhone app when it was free for a day, so I don’t have to worry about being away from my computer, or reading my passwords and trying to type them in one character at a time.

Workflowy is my go to app for storing everything in a list. I’m a natural list maker with paper and pen, but I’ve found that I want to save things for later and doing so with lots of PostIts just adds clutter. With Workflowy, my lists start with five main categories: Freelance, Personal, Work, Portfolio, and Job Search, and grow infinitely larger from there, but the amazing thing is that I can select one little bullet point and only view that sublist. Mega list-making coupled with insane simplicity. You need to check it out.

I recently started using the Cushion App designed and created by Jonnie Hallman, a designer/developer living in Brooklyn who freelances out of Studiomates. The design is really simple and it helps me to clearly see what projects I have going on, how long the project lasts on average, how quickly (or slowly) a client pays their invoices, and more. Cushion is currently in beta, so you can help suggest things to make it better before it launches.

I’ve recently started to embrace the Calendar on the Mac to schedule in blocks of time for my projects, part-time job, meals, and other things that I deem important. I really like seeing how I’m spending my time, so it helps to keep my accountable while still staying flexible if I need to move things around. My goal is to start scheduling a day in advance and then move to a general idea for the coming week.

Last, but not least is my favorite Moleskine squared notebook. I use it to write daily tasks because I love the satisfaction of crossing things off when they’re finished. I also love the sound that pages make when you’ve written on them front-and-back with pen. Anyone else?


Favourite part of living in Bowling Green & Louisville? Any favourite coffee shops / restaurants?

I’m actually about to move from Bowling Green to Louisville in the next two weeks, but my favorite thing has been how close I am to everything. I can be downtown in less than a five minute walk here, but now I’m getting excited to explore a new city!

My favorite coffee shop in Bowling Green is Spencer’s Coffeehouse, one of the few besides Starbucks. I actually worked there as a barista and later as a baker a few years ago, so I’m a little biased, but they really do make the best coffee around. For Louisville, Quill’s has the best coffee and The Irish Rover is my favorite restaurant! I always order the fish and chips.

I also have to mention Nord’s Bakery because they make the best doughnuts in the world (and my boyfriend currently works there). If you’re ever in the city, making a stop is a must!


A genie grants you 3 wishes for your business, what are they?

01– A new MacBook Pro! I bought my current MacBook back in 2008 when Apple first started making the aluminum models, so things have gotten a bit slower over time. Plus, having a lighter computer would be nice for traveling and taking my backpack to coffee shops.

02– A mentor, like Kathleen Shannon from Braid, who has experience starting a business and can help guide me along the way.

03– Dream clients who are on a waitlist to work with me! That would be so wonderful for financial peace-of-mind, although I would miss out on the struggle of earning my way into the biz.


Do you have any tips for someone wanting to get into the graphic design field?

For anyone wanting to become a designer, my advice is to soak in as much about design as you can. Become familiar with designers in the industry and figure out what you’re drawn to. Start using Twitter to share what you love and connect with other people. It may not make sense now, but making friends with your “competition” can help you find work or a new job, and will help create your community of fellow designers.  I absolutely love this quote by Ira Glass and find it to be 100% correct.

“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.”


Make sure to check out Jennifer’s accounts below!