Freelance Writing: Expert Insights on Getting Started from Freelance Pro Blair Sharp

Written by Monica Shaw

In this post I am delighted to introduce you to the inspiring and generous freelance writer, Blair Sharp. Blair is a serious pro when it comes to the freelance world. And like of all of us, she has a story. Blair found her freelance success through her relatable, clear content that speaks directly to the hearts of her readers. This also involved a lot of hard - but worthwhile - work. I'm so grateful to Blair for allowing me this interview where she opens up about her initial steps into the freelance writing world, sharing the pivotal moments and strategies that shaped her path to success. From her early challenges to the triumphs that have led her to contribute to renowned platforms and support fellow freelancers through "Hey Freelancer!", this post is a treasure trove of inspiration for anyone looking to start their freelance writing adventure.

What motivated you to go freelance in the first place? Any memorable moments from those early days?

In 2019, I started writing for a local parenting resource on a voluntary basis. Until then, I had no public writing experience and had done very little creative work since I was a teenager. 

I remember when my first piece was accepted to a “big name” publication; it was an op-ed for Scary Mommy. My jaw dropped when I got the email, and I immediately ran into my coworker’s office—I was thrilled! It was validating, and it motivated me to keep pitching.

Over the next year, I dove into everything freelance writing, including where to find clients and how to pitch, and even built my own website with no experience! As my bylines and income grew, I gradually reduced my hours at work and went part-time in October 2023. 

How did you build out your portfolio when you were just starting out - any tips for new freelance writers looking to showcase their skills?

When I decided to get serious about freelancing, I already had published bylines from that local blog. My portfolio is very basic—just hyperlinked titles and publication names in list form. 

If you have no experience or no writing samples, look for guest posting or volunteer writing opportunities. Reach out to smaller publications to increase your chances of getting accepted. You could also put your writing on a platform like Medium or Substack. Remember, you don’t need big names to prove you can write—your writing should speak for itself. 

If you have writing samples, consider what kind of writing you want to do and for whom. Tailor your portfolio for your ideal client and showcase your best work. Don’t forget to ask for testimonials—social proof works!

Every new freelance writer faces the challenge of securing their first paid writing gigs. How did you turn this challenge into a valuable learning experience and ultimately gain your first clients? 

When I began freelancing, I had 16K+ followers on my alcohol-free Instagram account. I landed my first client through a DM and still write for them today. 

To increase my chances of acquiring clients, I do a little bit of everything: cold and warm outreach, creating content on social media, networking with other freelance writers and people in similar industries for referrals, subscribing to all the job newsletters, checking job boards, joining online groups….the list goes on. 

I see a lot of new freelance writers out there trying to get gigs on tools like Fiverr and Upwork, but frustrated with the low pay and heavy competition. How do you rate these platforms and is there a better way for new writers to compete in this increasingly competitive field? 

When I started looking for clients, I looked into freelance marketplaces, but the process didn’t work for me. They’re extremely saturated, and I’ve secured clients in other ways and with less work. 

I believe in the power of personal branding. If you’re trying to get work online, it only makes sense to show up there. Your online presence allows you to stand out. Think of your LinkedIn profile as another landing page. You show your personality and add more social proof by posting and engaging regularly. 

Can you recommend any resources, courses, links, etc that you found particularly beneficial in honing your writing skills and succeeding as a freelancer?

You, like many freelancers, have a lot on your plate and other responsibilities - e.g., you’re a mom and part-time psychometrist (which sounds super interesting!) - any tips for balancing multiple jobs/responsibilities? 

This is something I’m always working to improve. It’s not easy, and it requires intentional maintenance every week! The short answer is that you just have to make it work. 

Try not to compare yourself to others because everyone’s circumstances are different. I’m thankful for my supportive husband, who understands that sometimes I need to work on weekends or go to bed early.

Figure out when you do your best work. I work at my day job on Mondays and Tuesdays, so I might respond to emails, engage on LinkedIn, or chip away at some admin stuff, but I know there won’t be any deep creative work done those days.

Try not to overload yourself in any area. I chose freelancing because I love the freedom and control it gives me. But all the things, work and personal, can take over my brain if I’m not careful. Taking care of myself has been key to my success. I see a noticeable creativity and productivity boost when I’m on top of my self-care. It’s wild what getting good sleep and moving your body can do for your mental health!

Another piece of advice that many freelancers struggle with is figuring out what is “enough.” This drives everything in your business. How much income do you need to live comfortably, pay your bills, and afford your needs AND your wants?

Work backward from that number. How many clients and at what rate do you get to that amount? Then, consider how long each project takes and how long you must work each day to complete those projects. 

Finally, you are a self-acclaimed cheese lover (so am I!). If you were to create a cheese board consisting of three cheeses, which cheeses would you choose? 

Only three!?! How will I ever choose? I don’t discriminate between cheese, but if you’re forcing me, I’d probably go with brie, one with a little kick—like pepper jack, and a basic cheddar. Ugh…that was challenging!

Monica Shaw

I founded Writer's Residence alongside my own journey as a professional writer in 2008. Today, I continue to work as a writer among other side hustles that contribute towards my freelance lifestyle. I write for other businesses - white papers, research reports, web content, and other forms of copywriting - as well as for pleasure on my own personal websites, and

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