Hallie Bagley

Before you start your coaching work, bring all of your humanity to the moment. Get centered and then really open up your heart to the person in front of you.


Hallie Gay Bagley was born into a thoroughbred horse breeding family in a small town in the Bluegrass, Kentucky. From her first English class, she immediately knew that writing and thinking about the craft of writing and different styles of the written word were “her thing”. At 11, she entered a Seventeen Magazine “short story” contest and thus began her love of the short story.

Heading to Dartmouth College, an Ivy League college in the northeast from Kentucky, she majored in English Literature, even studying the Renaissance Poets such as John Donne for a semester in London, England. One London night, while needing to produce a gigantic paper on the work of John Donne’s poetry, she felt totally paralyzed, and this memory later helped her connect with the compassion she has for her SmartWriting students, how to write when you have a “writing block.”

Later after graduating magna cum laude from Dartmouth, she was Managing Editor of The Paris Review in NYC, and then got her Juris Doctorate from Columbia University School of Law. 6 years of editing work at The Paris Review where true creative work was blooming, plus her memory of that long night trying to produce a John Donne paper helped her birth her essay coaching business SmartWriting.

The goal of SmartWriting is to stand beside young students who are navigating this important transition and to provide a sounding board with strong written word expertise to support them in their written work.

Where did the idea for SmartWriting come from?

In one month I had a call from two different people who knew I was an English major and good writer, they both asked me to “edit” their student’s admissions personal statements. After spending the whole day with the first one, a 17 year old who was applying to college, coaching him in the best ideas he or I could bring to the table, and writing about and helping him with tone, I called my husband on the way home and said, “This is what I was created to do.” My husband then said, “Then go do it.”

What does your typical day look like and how do you make it productive?

In the college admissions essay season from August 1 through about Thanksgiving, my typical day starts early with a cup of coffee and shower. Then I light those wonderful Bed Bath and Bodyworks 3 wick candles, ones like Balsam, in the back room, the SmartWriting office. Next at 8am we start, we, the student and I, sit on a huge (at least 9’ long) bright yellow tufted Chesterfield sofa, each of us at opposite ends, and we brainstorm, I coach, and they write the whole day until 11pm when we each go to bed. Sometimes we’ll take the laptop to an outside restaurant just for a change of scenery, and always we keep the light of inspiration burning in those Balsam 3 wick candles!

How do you bring ideas to life?

I’ve found that ideas come from all sorts of places. Like quotes or images or Apple News. I love the New Yorker profiles. Those profiles are fantastic for ideas. And I love reading book reviews for ideas too.

What’s one trend that excites you?

A trend that excites me is reversing modern trends. For instance, I would like to start a trend of FACE TO FACE meetings rather than Skype or virtual. In fact I’ve built my whole business around the amazing and incredible momentum of creative output that comes from face to face connecting across uninterrupted long blocks of time. Cal .

What is one habit of yours that makes you more productive as an entrepreneur?

I believe that the habit that makes me more productive as an entrepreneur is cultivating a love for people. This helps me talk to anyone I meet and a few times, it has turned into a wonderful student sitting on my SmartWriting couch. I love listening to podcasts and taking very long walks while listening. There I think, ponder and meditate, this recharging makes me more brave as an entrepreneur.

What advice would you give your younger self?

Relax. Pick people around you who relax and are relaxed. Don’t overreact.

Tell us something that’s true that almost nobody agrees with you on.

That family and relationships really matter. More than anything else!

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I tell people, I tell anyone who will listen, about my college admissions process with rising high school seniors to help them get through the terrible college admissions essay process. I also get up early and work till very late. That is called a good work ethic

What is one strategy that has helped you grow your business?

I think the main strategy that has helped me grown my business has been excellent customer service. Doing more for your student than other people do. I also think part of good customer service is really really listening to your customers (their parents).

What is one failure you had as an entrepreneur, and how did you overcome it?

One of my weaknesses is a casualness about making sure I have a signed contract. A couple of times, this has bitten me in the rear because when the final payment came due, people have a way of disappearing. Another failure has been that I’ve tried to do everything myself. Recently though, I hired a bookkeeper.

What is one business idea that you’re willing to give away to our readers?

An actual idea for a business is a speaking company: you will collect wonderful speakers and take a fee from placing them as speaker. As for business advice, Always start writing the hardest ideas first. The most words and the most difficult pieces. Never do the easiest first, this will make your business, whatever it is, succeed if you tackle the most difficult things first.

What is the best $100 you recently spent? What and why?

The best hundred dollars I recently spent was a ticket to David Byrne’s American Utopia at the Hudson Theatre in NYC. It will be a blend of gig, dance and a huge flatbed truck full of his prior hits. A great way to bring energy and creativity back to the SmartWriting coaching job. I also just spent $100 on a great Balsam 3 wick candle sale at Bed Bath and Beyond. It helps the Smartwriting yellow sofa crowd relax and be happy while we tackle the famous Common App personal statement essays.

What is one piece of software or a web service that helps you be productive?

I love my 15” MacBook Pro and along with that Pages, its Doc software, because without Pages none of my essay coaching students would be able to reach for their college placement aspirations. Excel is pretty terrific too because it keeps payables and receipts straight.

What is the one book that you recommend our community should read and why?

I recommend Truman Capote’s A Christmas Memory the short story of an aging spinster aunt and her young nephew (Truman as a boy) and their close relationship when he was a child. Just thinking of that relationship can make me pause with a soft spot in my throat. I love how their intense and loving bond is revealed, one that spans generations all over a rough-hewn kitchen table while making fruitcakes or heading with a grocery cart to buy supplies. It is good writing at its finest.

What is your favorite quote?

“We’re all just walking each other home.”
I love this because at SmartWriting that is what I try to do for each young student. To walk beside them and walk them home to themselves so that they can put “who they are” (no one else could have written their essays) onto paper. A parent has called me a sherpa because I walk beside them to bring them through the long hard college admissions process.

Key Learnings:

• Before you start your coaching work, bring all of your humanity to the moment. Get centered and then really open up your heart to the person in front of you.

• Always remember moments where you too struggled or had moments of true joy, and bring that empathy to your essay coaching. Listen beneath the surface of the words. This means always ask a lot of questions and always strive to connect through shared experiences. Even if you are a elder stateswoman like I am and they are 17.

• Read Cal Newport’s Deep Work, a book that makes the point that deep work is High-Quality Work Produced = (Time Spent) x (Intensity of Focus). Instead of focusing on multiple things at once, focus on one thing for large periods of time because that’s how to produce high-quality work. Furthermore, if you switch tasks repeatedly, then you will not produce high quality work, because something called “attention residue” will go into effect. The mind will still be stuck thinking about both tasks simultaneously, limiting the effectiveness of the mind. The point here is that High-Quality Work Produced = (Time Spent) x (Intensity of Focus).
• Practice awareness and trust your instincts. Often I brainstorm with students until there is a “click” the click of instinct recognizing a good idea. I try to wait until that “click” happens to coach the student to their best idea. Each time this click has happened, the result, the final essays have been pure dynamite.

• Pay attention to the power of choice. You can more efficiently manage your time by making it known to your brain that you have the choice to do work, and you will choose to do it.

• Don’t stop and start your work. By segmenting your day into blocks of time and working on tasks in order of importance without interruption, you’ll not only stay organized and refreshed, but you’ll also get more done.