Hallie’s Story: Life in Chicago for a Small Business Owner

In 2012, Hallie Borden decided to take a big risk and quit her steady yet unfulfilling office job to pursue a lifelong dream of owning her own store. Hallie will be the first to say that working as an entrepreneur is not always an easy path, but she also shows that it is an achievable and rewarding path. Here’s life with Hallie…

Fighting her own doubts that she was “too young and inexperienced” to own her own business, Hallie has spent the last few years doing just that: taking a career leap into the unknown and paving her own path as the owner of a small, handmade clothing boutique. Hallie quelled her self doubt by eventually realizing that there would “never be a perfect time to take such a big risk, so ‘right now’ seemed as good a time as any.”

One of the aspects of Hallie’s story that I find so empowering is that she ventured into small business ownership as a solo endeavor—no team, no business partner—just “a lot of dreaming about what my store would look like, where it would be located, and what I would call it” and then, of course, a lot of work and persistence. Hallie chose to open her shop in the very community-oriented Chicago neighborhood of Andersonville and, when looking for her first condo—where she lives with her fiance and wonderfully sweet dog, Sauvie—she decided it was most important to live within a community she loves and walking distance to her shop. As a fellow daydreamer, it was truly inspiring to spend time with Hallie, someone who who is actively engaged in the work of making her dreams a reality.

• Name: Hallie Borden
• Location: Andersonville, Chicago
• Job: Owner of the boutique, Milk Handmade

• What brought you to Chicago? I’m originally from Chicago and have always been in love with the city. In 2012, I opened a clothing boutique, Milk Handmade, in the Andersonville neighborhood, and immediately felt at home in the community. It’s a warm, relaxed neighborhood packed with incredible restaurants and great shopping.
• What’s a typical work day? I like to go for a long walk every morning and listen to music. Then I drag Sauvie, my greyhound, to Milk. She is the laziest pup you’ll ever meet, so our six-block walk to work takes a lot of negotiating and bribery. She lounges on the couch while I return emails and work on accounting. The shop is usually slow in the mornings, so that’s when I take care of business. The rest of the day is spent chatting with customers, rearranging displays, and meeting with designers to pick out new merchandise.

• What’s one piece of advice you wish you would have known when you made the shift to working as an independent business owner? That even if you own your own business, you’re still not “the boss”. I report to my customers! If I’m running late in the morning, I don’t think, ‘Oh well, I can’t get fired,’ I think, ‘Oh crap! What if a customer is waiting?’

• How long have you lived in your condo? Since Fall 2013.
• How did you find your place? My mom is a real estate agent, so we kept it in the family. I wanted to live within walking distance of my shop, and there wasn’t a ton on the market. I actually hated this place at first. It was a beige box without a personality. My fiancé spun “beige box” into “blank canvas,” and I was sold.

• What do you like most about your living situation? I love the high ceilings, natural light, and open layout. I like that it’s always warm in the winter. And I really love the personal touches we’ve added, like the Hygge & West wallpaper. I loved the pattern, then I saw it was designed in Portland and printed in Chicago. My fiance is from Portland and I’m from Chicago, so I took that as a sign to snatch it up.

• What do you wish you could change about it? I cook a lot and it is majorly lacking in counter space. I prefer small spaces in general, but I could really use an enormous kitchen. Also, the master bathroom has a tiny, useless second shower where a linen closet should be. I need to send a photo to Good Questions so that the commenters can help me figure out what to do with it!
• A typical night in: I rotate evenings between dinner with friends, going to the movies, and sitting on the couch with my face in a bag of marshmallows watching reality TV. But an ideal evening in is a big pot of bolognese on the stove, a few friends over, and some wine!
• Any funny stories about life in your condo? I recently signed up for a race (even though I am a terrible runner). I like to break big tasks into small steps that I can check off one-at-a-time, so I decided to train by running around my block, over and over again, adding a lap every few days. The entire neighborhood thought I had lost it. People would stare out their windows, ask me if I was alright—one woman screamed “I feel like I’m in Groundhog Day!” The race is now over and the neighbors are relieved.

• Favorite belongings and the stories behind them: My Borden milk truck—it was a perfect gift from my cousin. My shop is named Milk Handmade because my last name is Borden, like the milk. This truck has tiny bottles of milk packed in tiny crates in the back. I play with it often.

• My wooden fisherman was purchased recently from a tacky gift shop in Hilton Head. Everything in the store was magenta and covered with bedazzled dolphins, except this guy. I don’t know how he got there, but he was in desperate need of rescue.

• Another favorite belonging is my animal head necklace rack. This was a gift from my fiancé many years ago. It was the moment I knew he truly understood me.

• HALLIE’S PARTY PLAYLIST: (As someone who spends a lot of time hosting the public, I was excited for Hallie to share a Spotify playlist and she was ready, able, and willing to deliver.)

• Bonus Sauvie Outtakes: As an extra little pick-me-up for all of us…