Why I Started Freelancing

Blog Post 1 Why I Started Freelancing (Canva)

After over a decade in the legal field, I realized I was stuck, both professionally and personally.

I was essentially a passenger in my own life.

I started researching ways to earn income from home and quickly discovered the limitless potential of the freelance marketplace. I loved the thought of earning money on my own time, on my own terms. What really hooked me, though, was the idea that my earnings potential was only limited by how much time and effort I was willing to invest–there was no pre-fixed salary that would cap how much I could bring in.

After looking at some options, I jumped in and quickly learned…

Freelancing is hard.

My first freelance jobs were in transcription. I had years of experience doing dictation and thought this would be a natural foray into the freelance world. I started bidding on transcription jobs on content mills and soon spent hours transcribing audio files.

At first, I loved it. I’ve always loved learning new things, and transcription gave me inside access to a whole host of fascinating topics like tech, digital marketing, growing web-based businesses, the military, patent law, start-ups and entrepreneurship, and on and on. The transcription process itself was tedious, but I was getting to learn things well beyond my normal realm.

Freelancing was amazing.

The down side? I was literally spending hours and hours hunched over a computer desk with my headset and foot pedal struggling to complete assignments that, in the end, only brought in piddly money.

I looked for ways to make the transcription biz more profitable. I watched video after video to learn inside tips for becoming a faster transcriber. After awhile, I noticed something interesting. Many videos were set to run with closed captioning. I didn’t give this much thought until the day I came across closed captioning that was so chock-full of errors it was like witnessing a bad-lip reading parody. It was so distracting I spent more time reading the closed captions than listening to the tutorial.

After that, I couldn’t help but check the closed captioning on videos. After seeing an amazing amount of error-filled transcripts, I decided to review political campaign videos to see what ‘correct’ closed captioning should look like. Surely campaign videos would have accurate closed captions for their older and hard of hearing constituents who use closed captioning on a regular basis. I was shocked to find video after video of downright embarrassing automatic translation errors, many of which ran completely counter to the candidate’s platform (imagine the words ‘racism’ and ‘Nazi’ popping up in a candidate’s closed caption transcript without their knowledge).

Seeing the potential market for correcting error-filled YouTube transcripts, I learned the process of correcting (in some cases, creating) closed captions, and added video closed captioning to my list of services.

Soon I started getting requests to caption SEO/data analytics tutorials, podcasts, webinars, etc.

Freelancing was empowering.

I had pinpointed a need, researched the market, learned the skills and software necessary to produce clean, uploadable transcripts, and figured out how to pitch and market my services.

Clients were soon seeking me out.

Unfortunately, while video captioning was better money, it took twice as long to complete. Not only was I transcribing word-for-word, I then had to go back and time-sync the transcript to match the audio. I soon learned one of the most important business lessons of all time:

Services must be scalable for a business to grow and become profitable.

Competition in the transcription and video captioning field is pretty fierce. Individual transcriptionists and captioners are not only competing against their global counterparts, but big-volume businesses.

After six months of working endless hours for minimal profit, I returned to the bricks-and-mortar workforce.

Although the return to a regular paycheck was wonderful (getting paid every week was like Christmas), I never let go of the dream of working from home.

It’s all about marketing.

One day it dawned on me that I had been marketing myself all wrong.

A paralegal’s bread and butter is researching complex issues and using that knowledge to write compelling arguments on behalf of clients.

I had been so focused on looking for freelance opportunities with my minimal skillset (typing, proofing, editing) that I failed to see that all along I should have been marketing my high-value skillset: research and persuasive writing. I updated my online profiles to include freelance copywriting and other writing services.

This time I will not burn the ships.

Some advocate the “burn the ships at the shore” method of freelancing, i.e., eliminating all potential avenues for retreat so you are forced to take action toward your objective.

This was the method I chose in my first foray into freelancing. I did not, however, have a fiscally responsible plan in place.

It was nearly disastrous.

If I could give any words of advice for those desperate to quit their 9–5 to start freelancing now: BUDGET, PAY DOWN DEBT, and SAVE before making the leap.

Otherwise, your moments of euphoric freedom will quickly turn to panic and financial despair.

I’m all for gritting things out, eating Ramen, and grinding away. That’s great when you’re single with no kids. But when you have a family depending on your income for basic necessities, things get real super quick.

My freelance goals

I have serious goals for freelancing, but this time I plan to pursue them responsibly.

I plan to stay in a “real” job (synonym: steady paycheck) until I bring in a specific dollar amount per month. Doing so will allow me to stay solvent while I prospect, build my online portfolio and grow my business.

Financial goals

They say those who write down their goals and share them publicly are much more likely to achieve them. So, here goes:

I want to build a nest egg of $10,000 in savings (to start), pay down debt, save for home repairs and renovation, and really start socking away for my kids’ college tuition.

And while I’m building my business, I want to set aside money to travel with loved ones so my ‘someday’ bucket list items don’t get relegated to only when I retire.

My short-term goal is to bring in $2,000/month extra income from part-time freelance work by Christmas (five months away).

My long-term goal is to regularly generate $5,000/month or more from part-time freelance writing. To achieve this goal, I will need to find ways to generate passive income that makes sense for me, and through means that aren’t already oversaturated.

Can anyone really be a freelance writer?

I think so, but:

It will take focused, dedicated effort, day-in and day-out, week after week, month after month, year after year.

It will also take the most grit and determination that I’ve ever had in order to succeed.

The power of persistence.

Throughout my journey, I will be channeling these words of wisdom from NPR’s Ira Glass on the importance of persistence for those just starting out in creative work:

“…[The] thing that I would just like to say to you with all my heart is that most everybody I know who does interesting, creative work…went through a phase of years where they had really good taste and they could tell what they were making wasn’t as good as they wanted it to be. They knew it fell short. It didn’t have the special thing that we wanted it to have.

The thing is…everybody goes through that. And for you to go through that…you gotta know it’s totally normal and the most important possible thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline so that every week or every month you know you’re going to finish one story.

It’s only by actually going through a volume of work that you’re actually going to catch up and close that gap, and the work you’re making is going to be as good as your ambitions…

It takes a while. It’s going to take you a while. It’s normal to take a while.

And you just have to fight your way through that.”

Ira Glass, 2009

Interview Excerpt by Current TV

“Ira Glass on Storytelling Part 3”

Public Radio International


And that’s how Eleanor and Jane came to be. Named for two strong, independent women, Eleanor Roosevelt and Jane Austen, I created this blog to hold myself accountable to my lofty goals and to share my ups and downs as I move forward.

Next up for Eleanor and Jane

I will continue to blog here not only to hone my writing skills but to learn how to produce valuable, engaging content on a consistent basis.

Because the focus of this blog is building a successful and sustainable freelance career, I plan to include posts on self care and personal development as well.

Finally, starting in September, I will share a monthly income report with profits/losses to show how well I’m progressing. The figures may be slow going at first, but I know this is a long-haul journey. I am looking forward to Christmas when I can look back and see how far I’ve come in just five months!

If you’re working toward a dream of your own, or maybe have a question or comment, I’d love to hear from you.

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2 thoughts on “Why I Started Freelancing

  1. We are so proud of you, sister. Your article was so well written and delivered a powerful message that we can all share. You WILL achieve all that you strive for. You are tenacious in your strive to be the woman you wish to be. You have hit upon a need we seniors have for accurate transcription for closed captioning. I am fortunate to still have some hearing but use the closed captioning quite a bit. It is sometimes dreadful what appears on the screen and I shudder what those who rely on it to read what the speaker is saying. Many times it is just distracting on live broadcasts. There is no excuse for errors on canned series shows or movies. Many times the CC is not in sync with the dialogue. I know this because I still have some hearing and the CC is of no use at all out of sync.

    God bless you for your work. You are a beautiful woman and soul.

    Liked by 1 person

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