The Juggle turns one: shit, we built a company!

Woo! We’re celebrating our one-year anniversary here at The Juggle. We took some time to reflect on what starting a company and developing a side hustle means to each of us. Here are our reflections.

Alyssa

Since starting The Juggle, I moved from Austin to New York City, worked on three start-up ideas and started a new full-time job. This past year has been full of change and loneliness. Through it all, The Juggle has been constant and reliable; it has given me a sense of connection to Sarah, Jen and Amy, while pushing me to have vulnerable, real and honest conversations. Building a company with three incredibly different women can be frustrating, rewarding, time-consuming and enriching — sometimes in the same breath. A few things I have learned this year:

• Writing is hard and TAKES TIME. Not just for me, but for everyone. Good writing takes a million edits, including some ego-crushing moments when I knew my editor was right but I didn’t want to admit it.
• Listening to my energy levels is important to survival. There are some weeks when I am in a groove and working on The Juggle feels like exactly what I need to be doing. Other weeks, I can barely muster the energy to repost an article on social media. I have learned that even with a side hustle I need to take breaks AND it’s okay to slack off when my energy isn’t there.
• Being organized matters. My entire Juggle life lives in Trello and Slack. I sometimes pooh-pooh project management, but when I’m busy with a million things going on, a clear organized system and direct communication is key to my sanity.

I had two favorite articles this year:  1)Tales of the chronically late and neurotically early. I enjoyed collaborating with Jen on this one and I think it’s funny. And 2) When to leave your job. This one was tough for me to write; it felt deeply personal to share with the world that I was “quitting” something. For most of my life, I have valued perseverance and never quitting, so admitting that I needed to leave my job felt like admitting failure to all of the internet. I couldn’t be more happy about the decision to this day, but writing the article was painful. 

Sarah

The thing I am most proud of about The Juggle is simple: that we did it. So many people talk about wanting to do or make something, and we actually put in the work to make the thing we dreamed of. 

The other thing I’m proud of is our relationship with each other. Building something almost entirely remotely (we don’t see each other in person very much) requires very efficient and direct communication. We learned quickly that if we didn’t speak up when something wasn’t working or something had hurt our feelings, we wouldn’t be able to move forward with the speed and agility needed to do what we do. Getting more comfortable with totally honest and unfiltered communication has made me a better and braver person.

Other learnings:

• Starting a creative side project like this requires SO. MUCH. WORK. It is not something you can just work on when you feel like it. I cut a lot out of my life to make room for The Juggle and I don’t regret it.
• Writing about my personal life isn’t as scary as I thought it would be. When we started, I was dead set on NOT talking about my personal life. But I quickly realized that our articles would be dry and boring without an acknowledgment of the fullness of our lives. Since then, I’ve realized that the things I didn’t want to write about (insecurity, anxiety, negative self-talk) were things I felt ashamed of. Pushing past shame and putting these things out into the world took away their power. Plus, the articles where we are most vulnerable are often the ones readers connect with most.
• Hearing from our readers is the most rewarding and exciting thing ever.

My favorite article of the year was Jen and Sarah spill their guts on insecurity because Jen and I pushed our comfort boundaries, talked about something that everyone deals with and tried out a cool new back-and-forth format. My inbox and phone were full of messages from people this article resonated with after we published.

Jen

I love what we’ve created with The Juggle — a vulnerable, relatable safe space for success, insecurity and humor. I love that it gives me a personal venue to work on improving my writing and challenging myself in new ways. And it is definitely a challenge. The article Sarah said was her favorite is one I haven’t been able to re-read to this day. Sometimes putting everything out there — both emotionally and creatively — is fucking terrifying.

My favorite thing I wrote this year was “I’m trying to be more positive, and it actually seems to be working.” Positivity continues to be a work in progress for me, one I have varying degrees of success with depending on the day. I’ll also agree with Alyssa about “Tales of the chronically late and neurotically early” — it was really fun to write and I think we succeeded at what we were trying to do, shedding light on our own tendencies that are foreign to each other and getting to understand where the other person was coming from. 

Amy

We launched The Juggle when my daughter was six months old. I was about a month into a new job and had never started a company before, let alone worked full-time while caring for another human being. So it’s hard to divorce my reflections on launching The Juggle from my reflections on stepping into a caregiver role while working and contributing to a side hustle. It’s one big awesome messy jumble. 

My biggest takeaways from this year are the friendships I’ve built with Sarah, Alyssa and Jen. These women are now some of my closest friends, and I’ve only met Jen in person once! 

Other highlights and lessons from the year include:

• Editing and writing are related but distinct skill sets, and you need both to create high-quality unique content. My editing skills are stronger than my writing skills at the moment, and I’m constantly learning from the writing of my fellow founders and our guest contributors.  
• Giving and receiving constructive feedback is difficult, period. Giving and receiving constructive feedback on an unpaid, side-hustling, distributed team can be even more delicate and fraught. We’re frank with each other (we don’t have time to dance around issues!), which is not something that comes naturally to me, and I’m slowly getting better at communicating more directly. In this sense, The Juggle has provided a space for me to practice behaviors and skills that I’ve had difficulty cultivating in personal and other work relationships, like asking for what I need in terms of communication. 
• Dr. James P. Comer once said, “No significant learning can occur without a significant relationship.” Building meaningful relationships with each other has been key to our growth and sustainability. Our “hey girl, hey” check-ins, Zoom video calls and in-person retreats have helped us be honest and vulnerable with each other. The remote and part-time nature of our work makes the sense of connection and trust between us that much more important.

My favorite article of the year was Talk to your parents about their will TODAY because it allowed me to create something good out of a bleak and irredeemable experience. I learned and was able to share how critical it is for your parents to document their estate and end-of-life wishes. I’ve received a lot of encouraging messages from friends and other readers who initiated conversations with their parents after reading the article. (Thank you.)

Dearest readers: we’d love to hear what The Juggle means to you and what you’d like to see more of. Everyone who comments on this article will be entered to win the chance to select a topic for an upcoming article.

Written by:

Alyssa Jethani, Sarah Overmyer, Jennifer Harlan, Amy Madore

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