Interested in starting your own entrepreneurial journey in freelancing but unsure what to expect? Then read up on our interview with Jennifer Henry, a marketer, publicist, and content creator based in Boston, MA, USA.

What's your business, and who are your customers?

At my core, I'm a writer and integrated marketing generalist who specializes in public relations and media strategy. I do everything from fully integrated strategic plans, brand identity, and development to creating content for blogs or social channels for campaign optimization, coordinating nonprofit partnerships, crafting press releases, pitching media, managing accounts, editing, writing original articles, and more. I've been really lucky to work with a variety of wonderful clients in a range of industries: beer, nutritional therapy, biotech, entertainment, interiors, finance, venture capital, retail, and consumer healthcare, among others. Sometimes I work directly with brands or agencies looking to scale up to support larger-scale projects. It's super fun, and I feel fortunate to know lots of great creatives and brand folks.

Tell us about yourself

Currently residing near my hometown outside of Boston, MA, after years in Vermont, I am an equal parts city slicker and country life lover. I've been doing freelance writing for a little over three years now, but in the industry for close to a decade, with former years-long in-house tenures at Boston Beer and MIT, plus a stint at an NYC marketing agency. I also attend a graduate program at the Bread Loaf School of English at Middlebury part-time. I have spent summers at their Santa Fe, NM, and Ripton, VT campuses, with sights set on graduating next summer from their campus at Oxford University. My academic interests lie in climate fiction and the intersectionality of environmentalism and anti-colonialism. I am someone who likes to push the limits, believes in both working hard and deep rest, and doesn't conform easily. This is part of what drew me into being my own boss, which I saw a few of my friends successfully doing, particularly women, who found more flexibility and less of that hierarchical burden working for themselves. They were working on super cool projects, and I wanted to be in that world. I am definitely driven by continuing to learn about a broad number of things, meeting new people, not niching myself down into one subject or specialty, and expanding my expertise into various industries. Cliche, I know, but variety is the spice of life! And after all, we contain multitudes (which also happens to be the name of my brand new Substack: containmultitudes.substack.com).

I've also been working with Julia Cameron's The Artist's Way, which is sort of a guidebook to boost creativity, and encourages three pages of journaling each morning which totally grounds me, clears the docket, and optimizes my creative juices for the day. The author also insists on solo dates with your creative self, where I will head to the museum, go for a long walk at the beach or get offline to go analog for the day with my journal. Boredom breeds creativity. As Austin Kleon says, "Creative people need time to just sit around and do nothing."

What's your biggest accomplishment as a business owner?

I'm not sure I have a singular big accomplishment; it has felt more like a series of small wins and lessons being integrated towards something bigger. I think starting to branch off on my own, casting aside imposter syndrome to start a side hustle three years ago, and continuing to grow has been a tremendous series of accomplishments. Continuing to get business through referrals and collaborating with great people and brands, all while pursuing new opportunities. It has taught me so much about finding purpose, setting boundaries, and developing a healthy work/life balance. As much as I would love to win an award for my copy someday, being able to make your client beam with happiness, then clock out when you want to go take a hike with your dog is a pretty great accomplishment.

What's one of the hardest things that comes with being a business owner?

We all have our challenges, but I think the biggest one is developing a solid community to lean on, vent to, and have the understanding that your "competitors" are actually your allies. I think, especially as a woman in business, we are taught to see each other as competition instead of a support system, unlike the way men operate in business. This is not our fault; it's a manifestation of our culture and society, which has raised us this way with media, stories, and patriarchal structures that pit us against each other. It's getting better, and I feel really lucky to have found lots of little corners of people that not only don't see me as a competition but make more space at the table, offer resources and refer me for jobs – and I them. Within these circles, I've joined Slack channels, coworking sessions, and group texts to socialize as we would around a corporate water cooler which is so important to feel part of a group.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Don't be so hard on yourself, as cliche (full of them) as it sounds: anything worthy of your time takes patience. As Mary Oliver said: "Keep some room in your heart for the unimaginable." And the more practical ones:
  2. Get everything in writing, i.e. business plan, contracts with clients, and business log.
  3. Most importantly, secure the bag: educate yourself on reasonable rates, especially if you are a woman, Black, or a person of color who has historically experienced wage gaps.

Where can people find you and your business?

Website: https://www.jenniferhenry.me/
Facebook: https://www.facebook.com/jennifer.henry.1650
Instagram: https://www.instagram.com/itsjenniferhenry/
Twitter: https://twitter.com/itsjenry
LinkedIn: https://www.linkedin.com/in/jennifer-henry-/


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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