#AFreelancersLife: Jess Lander, Writer & Social Media Specialist

Here's why I started #AFreelancersLife: To highlight different freelancers every month from all sorts of backgrounds and pick their brains about what they do and how they do it. Check out all previously featured freelancers right here. If you would like to be featured just drop me a line and let me know! Today's post features Jess, a writer and social media specialist who gets to live in breathtakingly beautiful Napa Valley, has several local wineries among her clients and is basically leaving THE LIFE. Wanna trade for a bit, Jess?

How long have you been a freelancer and what exactly is it that you do?

In February I celebrated two years of full-time freelancing, though I’ve always freelanced on the side. I’m a journalist, writing articles on everything from sports to business to dating and relationships, but the bulk of my work comes from managing the social media channels of my clients, who span across a variety of industries, like fitness, wine and medical. Additionally, I do email marketing, copy writing, PR and any number of digital marketing initiatives.

How does your typical workday look like, if there is one at all?

When I wake up in the morning, I grab my laptop and do my first hour or two of work from bed! Later, I relocate to either the couch or my home office. I always take some time out of the day to workout, and sometimes to treat myself with a pedicure, massage or pool time. I meet with clients usually a couple times a week, and try to make lunch or happy hour dates with friends once or twice too. If I don’t get out of the house often enough, I get stir crazy!

What does your freelancing work entail regarding activities and duties?

For social media, I develop a strategy for each client based on their goals and things like content and posting cadence, and then I help them create and post content, manage their Facebook, Twitter, Instagram and Pinterest accounts, and create and manage any social media advertising. Many of my clients also hire me for other marketing initiatives like writing website and blog copy, creating and sending emails and newsletters, PR outreach, etc. As a freelance journalist, I interview subjects and write articles for newspapers and magazines on topics of sports, sex, dating and relationships, business, lifestyle and more.

What has been your biggest highlight so far as a freelancer?

In 2015, I went on vacation nine times, totaling 52 days. One of the biggest reasons I went freelance was for the flexibility and unlimited vacation days, and I make sure never to take that for granted. Last year I went to weddings, brithdays, visited my family and friends all over the country, took a road trip with my boyfriend, etc. The best part was being able to take my work with me and not lose out on any business! So far I have seven trips planned for 2016.

How does your previous education & experience tie in with your current freelancer work?

I went to school for journalism and then spent two years working in a newsroom, in addition to freelancing for several publications on the side. I left the newspaper industry for a cushier marketing job, where I gained the bulk of my content writing and social media experience working for a large start-up. When I got fed up with the 9-5 world, I realized I had a wealth of knowledge and skills, a big portfolio and a lot of contacts to help me start my freelance business. It probably would have been much for difficult to land clients and get my business off the ground without all of that.

Do you sometimes have motivational lows, and if so, what do you do to get out of your low?

Yes, and they usually come during slow periods. I’m much more productive when I’m drowning in projects. But unless I have some big, important deadlines to make, I allow myself to get a little lazy every once in a while and spend most of the day binge watching bad TV or something. I’ll usually bounce back in the next day or so. Friends are always asking me how I stay motivated and I tell them I’m actually more motivated than I ever was at my 9-5, where I was guaranteed a paycheck every two weeks. The reason? As a freelancer, if I don’t work, I don’t get paid and I can’t pay the bills. My time is also much more valuable now that I’m not required to sit at a desk for eight hours, so I don’t mess around watching videos on the Internet as much as I used to.

What do you love about being a freelancer? What do you hate?

I love almost everything: Being my own boss, making my own hours, working in my underwear, the flexibility, the potential to make as much money as I want, working from home—the list is endless. There’s also a lot of perks, for example, I have a free gym membership and I get to drink a lot of wine from working with several Napa Valley wineries.  

I wouldn’t even go so far to use the word hate, but my least favorite parts of freelancing are handling my own accounting and buying my own (terrible) health insurance. I pay several hundred a month and I have a $4,500 deductible! I also find that while I have a really flexible schedule, it’s really difficult to ever completely unplug, even on vacation. It’s just me, so if a client needs something, I feel the pressure to be available.

How do you structure your day: When are you taking breaks, when are you working, when are doing which tasks in particular?

The first things I address when I wake up (without an alarm) are emails. Then I do a run through of all of the social media accounts I manage. I take a break around lunchtime for either lunch or a workout (or both), and errands if I have any. I use a few hours in the afternoon to work on bigger, non-social media related projects, and my own blog if I have time. I’ll do another sweep of social media before I close up for the day, usually around 5. I try not to work too much at night so that I can spend quality time with my fiancé once he gets home from work, but every once in a while I will if I know it’ll help me sleep better. I’m always reminding myself that I went freelance so that I could have a better work/life balance, which means I shouldn’t be working late or overtime!

Which are your favorite 3 websites or apps you’re using on a regular basis regarding your freelance work?

My new favorite app is Word Swag, which is great for social media. It lets you take a quote and make it super visually pleasing. It’s not an app, but I live by my iPhone’s Personal Hotspot, so that I can literally work from anywhere I have cell service. I’m also on Facebook all day, every day because I manage the accounts of about a dozen brands.

Tell us about an exciting project you have worked on which made you proud.

The best freelance project I ever had was to write two chapters for a book about my favorite baseball team, the Boston Red Sox. I wrote more than 20,000 words in one month and it ended up amounting to 60 pages. It’s the first and only time I’ve been published in a book and it’s fun to find copies of it on the shelves every time I go back and visit Boston. 


If you want to keep in touch with Jess and her work, make sure to follow her on Twitter or check out her website.


Thanks for taking the time to read this! I'm Melinda and I offer creative and strategic coaching for passionate solopreneurs and freelancers. Connect with me on Twitter or sign up for my bi-weekly newsletters for more information and resources on #AFreelancersLife.