Why Every Self-Starter Needs This Kind of Friendship

Maybe it’s my inner Leo talking, but I really value my personal and professional connections. Ever since becoming a full-time freelancer, I’ve realized just how important these unconditional, have-your-back relationships are. Being your own boss can be lonely. You don’t have colleagues or a work wife who can help you brainstorm or empower you during a hard week. No matter what industry you’re in, it’s important to have people in your life who can cheer you on (and vice versa). I’m so thrilled to chat with Hannah about ambition, her books, and the unapologetically supportive relationship I think everyone (especially self-starters) should have.

Ever since we met in 2013, we’ve had an insanely supportive friendship. Why do you think that is?

Hannah Orenstein: This might sound mushy, but I truly care about all parts of your life (work included), and I know you feel the same way about me. I think a good chunk of our friendship has always revolved around discussing our careers because we both care a lot about what we do, and we work in the same industry so we very much get what the other is going through. I love knowing that when I have an urgent question about work (or the latest true crime doc on Netflix), I can text you for advice and get feedback I trust.

If I can brag about you for a sec: When you needed to replace your e-reader, you bought one in the perfect shade of yellow to match my book cover so that your Instagram promoting my book launch would look extra cute. (And this was just a few months after we huddled over paint samples at a bar to choose the shade together!) I am unbelievably lucky to have that kind of next-level support from a friend.

Why do you think it’s important to have these supportive, creative friendships when you’re pursuing a passion project?

Hannah: When you’re working on a project by yourself, a friend who can serve as a sounding board is so valuable. That might mean helping in practical or technical ways (like sharing their work with your friends and followers, or offering advice on a problem), or it might mean being there for emotional support. I know that I can sometimes get in my own head — like, if I feel daunted by writing a challenging scene or fixing a tricky plot hole, I can spiral about it for days. But I know you have a superpower for giving the world’s best pep talks, and if I hear you say that I’ll be able to figure this out, I’m likely to believe you. One of the most effective ways to support a friend, I think, is to simply remind them how great they are.

When you have friends who are also self-starters (or working in a similar industry), it can be so easy to compare yourself to them — and even get a little jealous. What are your tips for combating that?

Hannah: Unless you’re literally competing for the same exact job, someone else’s success doesn’t take away from your own. I like to remember that no two careers are going to look exactly alike, and that there’s no sole path to success. When I feel twinges of jealousy, it’s usually because I really admire what someone is doing and would like to do something similar. I’ve learned to lean into that feeling and support the person — whether that means sharing something they’ve written on Twitter or buying their books. Sometimes, I’m lucky enough that it sparks a friendship.

Regardless of your plot, your books never fail to highlight strong, female friendships. Can you tell me more about that creative decision?

Hannah: Friendship has made my life so much richer and I want to celebrate that in my fiction. A lot of the friendship scenes in my books mirror my own friendships pretty closely: There are a lot of scenes where friends go out to order cheese plates and glasses of wine, and discuss their careers and relationships. I’ve made all my best life decisions after discussing them in detail with friends over wine and cheese. It’s an important part of the decision-making process!

Finding a genuinely supportive friendship is easier said than done. What tips do you have for subscribers who are looking to build that community of self-starters?

Hannah: Right before the pandemic, I went on a string of friend dates with women I’ve interacted with on social media but had never met IRL. We had so much fun and it felt like such a natural place to start a friendship because we had already followed each other and DMed a bit. Conversation was easy because we already knew bits and pieces of each other’s lives thanks to Instagram. So, if there’s someone who seems super cool online, I’d suggest sending them a DM and inviting them for a Zoom happy hour.

Hustler of the Week: Hannah Orenstein

Congratulations on Head Over Heels. It truly is my favorite book of the year! What inspired you to write this novel?

Thank you! I spent 15 years of my childhood as a gymnast and have always wanted to write a book that celebrated the sport. It’s taught me (and millions of other people!) so much: Discipline, dedication, confidence. The idea for this novel — about a former elite gymnast who coaches an aspiring Olympian amid a scandal that rocks the sport — fell into place about a year after Larry Nassar, the disgraced sports medicine doctor, was sentenced to prison. I had been following coverage of the story closely, and it helped me understand the lens through which this book needed to be told: I couldn’t write a celebration of gymnastics without also exploring the myriad ways the sport systematically fails girls and young women. The book contains both.

What I find so interesting about your career as an editor and author is that both are fueled by creativity. How do you keep the creativity flowing?

For me, it comes down to routines. I have a few routines that I stick to with my work at Elite Daily (i.e. a daily brainstorming session, staying organized with spreadsheets, weekly check-ins with my boss) and a few that I find helpful with my fiction (i.e. dedicating weekend mornings — when I have the most energy — to writing, setting word count goals, holding myself publicly accountable to those goals). It might sound rigid, but I think when you subconsciously know what to expect from your day or your work session, it’s easier to get into the groove. I also take a lot of notes on my phone so I don’t forget any ideas that pop up when I’m away from my desk.

You’re also working on another side hustle! What can you tell Office Hours readers?

Later this year, I’ll be launching a guide to using Instagram for authors. It’ll be packed with insider tips about growing your following and using social media to sell books. It’s not ready yet, but if you’d like to receive an update when it’s live, sign up here.

Give Hannah some love by following her on Instagram and buying her books: Playing with Matches, Love at First Like, and Head Over Heels.

Like what you see? Subscribe to “Office Hours with Kelsey Mulvey” here.

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