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How One Mom Found Career Freedom in Freelancing

Long family vacations, time off for field trips, and working only while the kids are in school sounds like the dream schedule for any parent – and freelance writer Alli Hill was determined to make it her reality. After revenge-quitting her full-time day job, she jumped into a flexible freelance writing career that gave her a higher salary, fewer working hours, and more time for the things that mattered.

Since the age of four, Alli knew she wanted to write for a living. The adults in her life – parents, teachers, and mentors – supported her dream, telling her she had a natural way with words and that writing suited her. Several years after graduating college with a Bachelor of Science degree in Mass Communications, Alli couldn’t find the type of writing job that would give her the best combination of a high salary and flexible working hours – so she made her own. 

Three years after venturing out on her own, Alli launched FreelanceSpeak – a blog and brand dedicated to helping other freelancers find the same freedom she enjoys. Here’s how she turned her childhood dream of writing into a flexible, well-paid career.

About FreelanceSpeak

Alli started the FreelanceSpeak brand as a way to highlight her own journey into freelancing and to provide resources to other freelancers. 

Going into freelancing was a lonely road. She didn’t know anyone else who made a real living writing, nor did she know anyone who freelanced as a career. She taught herself most of what she needed to know, everything from pitching clients to handling payments and taxes. Overwhelmed at times, Alli searched online for other resources to answer her questions, but only found bits and pieces of the full freelancing puzzle. 

With FreelanceSpeak, Alli aims to build her own puzzle for freelancers – one that’s complete and all in the same place. 

“When I was building up my freelancing venture, I didn’t feel like I had great resources. I had been burned by expensive online ‘courses’ in the past that weren’t helpful. I knew how to use Google but I felt like the blogs I found were very incomplete. I didn’t know the right questions to ask. I hope I can change things for future freelancers.”

It started as a blog, offering free articles that each focused on a specific freelancing topic or challenge. She recently relaunched her website to include free and paid freelancing courses, one-on-one coaching sessions, and bookings for speaking opportunities. In addition, Alli plans on starting a podcast on freelancing as well as publishing a book in 2022. 

Along with her blog, Alli also welcomes guest blog posts. She believes other freelancers have great stories and tips to share, so she encourages other freelancers to publish their own insights under the FreelanceSpeak brand. In exchange for the blog content, Alli provides a by-line, bio, and backlink to help other freelancers build brand authority. 

Freelancers of all styles – writers, graphic designers, website builders, bookkeepers, career coaching, and so many more – can benefit from Alli’s insights via FreelanceSpeak. From beginners to seasoned solo professionals, she gears her business toward helping others fill their knowledge gaps and achieve career freedom – whatever that might look like to them.

Alli’s Story: How She Turned a Childhood Dream into a Six-Figure Salary

Even though Alli always knew she wanted to write for a living, she didn’t know what a career in writing could look like for her. She didn’t want to write novels or technical manuals, nor did she want to go into print journalism after college. So instead of using her degree immediately, she sat on it for a while as she explored life without a career. 

Turning a Nightmare Job into a Golden Opportunity

After having her first child, Alli planned on being a stay-at-home mom. But six months after the birth of her son, she found what she thought would be the writing career she had always dreamed of (with a little customer service on the side). It was a multi-duty role for a local marketing company, but since “writer” was part of the job title, she thought she was walking through the right door. And she was right – but she had to walk through a few more doors (and open them herself) first. 

She accepted the job with the idea that she’d be working 9 am to 5 pm, with an hour lunch and two 15-minute breaks. She also loved the idea of having all bank holidays off with pay. This gave her time to run errands during the day and enjoy a personal day every now and then. 

Just after a year, though, her boss reduced the number of paid holidays, demanded an earlier start time for the day, and slashed the lunch hour in half. What’s more, there was very little writing involved in her daily duties (almost none, in fact). It wasn’t the job she thought she signed up for, but having signed a contract, she felt stuck. 

“Staying at a job I hated paid off. My boss purchased an online content marketing course for me to take at work, hoping I could expand my duties even though expanding my pay never came up in these conversations. While taking this course, I started feeling envious of people who could come up with these courses for a living. It was something they could do from anywhere. And it got me thinking: could I create my own career and actually make money from it? I decided to at least try it.”

Finally Taking a Leap of Faith

It took Alli a month to complete the main content marketing course along with the free resources that came with it. After that, she started looking for freelance writing gigs online using job boards like Craigslist and ProBlogger. Just two weeks later, Alli landed her first freelance writing client. By the end of the month, she had four clients that kept her busy after her normal working hours. 

“I was coming home at 5:30 pm after working a full day. I had just a few hours in the evening to be a mom (dinner, bath time, snuggles, bedtime), then I hopped onto my husband’s ancient laptop computer and worked for 4-5 hours at night. Repeat the next day. I was staying up so late every night trying to get clients, working on client orders, and figuring out whether I could really sustain myself as a freelance writer.”

Alli didn’t want to quit her day job until she knew she wasn’t just having beginner’s luck. Nor did she want to invest a lot of money into her business until she knew she would see an ROI. She got a promising answer to both of these questions in less than a year.

“I started freelance writing in August of 2016. By May of 2017, I had my letter of resignation signed, sealed, and delivered.”

Alli was working nearly two full-time jobs by the time she was ready to quit. At that point, she was making more money writing than she was at her day job. And within three years, she had turned her income into a six-figure salary working under 40 hours a week. 

Overcoming 6+ Years of Freelancing Challenges

Alli specializes in freelance writing for digital channels, such as blogs, websites, and social media. While good content writing is in high demand, there are never any guarantees in freelancing.

One of the first challenges Alli faced after shifting to full-time freelancing was competition. Pitching via job boards could get exhausting, plus she was pitching the same prospects as hundreds of other freelance writers looking for work. Every pitch had to be tailored to the posting, and there were never any guarantees she would get a callback. 

She ditched the job boards within a year of freelancing in favor of online marketplaces, like Fiverr. Fiverr took more of an inbound approach, where clients would come to her and she could focus on fulfillment instead of marketing.

Another key challenge Alli experienced was building her personal brand. As an in-demand freelance writer, she preferred to spend more of her time serving clients, which left very little time for her to work on her own blog and brand. After launching FreelanceSpeak, Alli found it hard to keep up with regular postings and updates. She had to take a step back once COVID hit because her writing business got even busier. 

There was also the challenge of saying no to work. In the beginning, Alli’s only goal was to replace her full-time income with writing. She didn’t turn down work because she felt that every job was a step closer to her goal. Looking back, she realizes now that saying yes isn’t always in her best interest. “Some jobs are better suited to my skills than others, and I can better utilize my time when I accept only projects I’m interested in.”

Looking Forward to the Future

Despite the many challenges that come with freelancing, Alli believes there are more opportunities than risks. First and foremost, the chance to take full control over your career. 

“I didn’t want to punch someone else’s time clock. I didn’t want to ask permission to go on vacation with my family. I didn’t want people to miss me if I slipped out of the office for a bit to see my children’s school play. I needed more control over my schedule and the things that make life worth living. Working a traditional job just didn’t give me those things.”

For Alli, freelancing also gave her more control over her income. If she wanted a pay raise, she could decide whether to charge more for her services, work more hours, expand her services, or find other revenue streams, for example. She could also take full credit for her work and skills instead of having her name attached to someone else’s agency. With more control over the outcomes she gets for her clients, her own reputation improves, too.

Having been freelancing for six years and counting, Alli sees even more opportunities to grow her brand and business. From growing a team of writers and admins to adding new revenue streams, Alli is finding new ways to add value to her clients, her team, and the freelance community at large.

Alli’s Best Freelancing Advice to Aspiring Freelancers

Freelancing has been life-changing for Alli, and she knows that others who are stuck on the traditional employment hamster wheel can find career freedom with freelancing, too. She advises taking a similar approach she did so that you have a security net while building your dream.

“You can freelance and work full-time. You can freelance or work part-time. If you’re employed, I highly suggest testing the freelancing waters before you quit. This takes a lot of pressure out of learning and trying to figure out what you don’t know and what you really need to know. Once you start building up a client base and know you can sustain yourself even if you lose a client, feel free to hand in your notice.”

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