We recently connected with Alyssa Greenfield and have shared our conversation below.

Alright, Alyssa thanks for taking the time to share your stories and insights with us today. Let’s talk about social media – do you manage your own or do you have someone or a company that handles it for you? Why did you make the choice you did?

As a business owner who helps founders with their own social media content, you’d think I’d have an easy time figuring out what to share on my own social media. Well, not exactly! In fact, the work I do means I spent a lot of time overthinking what I share.

Am I sharing things that are too personal? Am I talking to the right audience? Do I sound like I know what I’m talking about?

But I’m committed to managing it myself because I learn so much in the process. And then I can pass on what I learn to my clients! Over the years, I’ve found ways to take some of the pressure off my posting strategy. I don’t worry about doing things that are “algorithm-friendly,” I focus on having real conversations with other people in my industry, and I don’t stress about posting every day. It took a while to get here, but I’d rather have a post really resonate with five people than get dozens of passive “likes” from people who won’t remember it in 30 seconds.

Alyssa, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I team up with B2B startup founders on storytelling and thought leadership projects that support their fundraising, customer acquisition, and hiring goals. Through content strategy and done-for-you content, we focus on telling stories and sharing ideas that resonate with the right audiences — and get them to take action.

I’ve been putting my journalism degree to good use throughout my career, working with growth-stage startups, Fortune 500 companies, and award-winning content agencies. I’ve produced content for IBM, Ernst & Young, Capital One, Lockheed Martin, John Deere and other brands you’ve definitely heard of before. And my writing has appeared in TechCrunch, Entrepreneur, Inc., Quartz and more.

Can you share a story from your journey that illustrates your resilience?

I was laid off from my very first job: a magazine in New York City. I didn’t see it coming at all.

I was mid-way through a lease on an apartment in Brooklyn with a salary that didn’t allow me to build up much of a safety net the past nine months. Thankfully, I was told I could stay on board for two more months. I immediately switched into “job search” mode. I had to. I let everyone in my network know what was happening. I applied to things furiously.

I wasn’t making progress on my search. But one day, a friend mentioned she knew someone that was about to leave her job. A job that was perfect for me because, well, it was basically the exact same job I’d been doing. It paid a little more, too. I interviewed, and before long, I had a job offer in hand — about a month shy of what would’ve been my last day at the magazine. I gave my notice and started fresh. It felt like nothing short of a miracle that I landed on my feet without a gap in employment.

Years later, I was applying to a new job. An amazing opportunity that I wasn’t sure I was qualified for. In my cover letter, I wrote about that layoff. I figured it might catch the attention of the hiring manager (it did) and show I was resilient (it did). I got that first interview, then a second, and then I landed a brand-new job in a brand-new industry. A job that laid the foundation for so much of the work I do today. Looking back, my career path has been a windy one to say the least. But I love that it’s one filled with resourcefulness, trying new things, and a whole lot of resilience.

Any insights you can share with us about how you built up your social media presence?

My two priorities for social media are: 1) Keep it real
2. Be as helpful as possible

For anyone just starting out, it’s easy to feel stuck. One of the best pieces of advice I’ve heard is to go through your photos and make notes of all the stories that come up. One by one, sit down and write about each experience , what you learned, or how it changed you. In the beginning, aim to answer and post just one a week. The goal is to get comfortable and build a habit. You’ll have plenty of time to think about strategy later…

Contact Info:

• Website: https://owlstreetcontent.com/
• Linkedin: https://www.linkedin.com/in/alyssa-greenfield/
• Other: Newsletter: https://mailchi.mp/owlstreetcontent/leading-out-loud