Online Options for Daily Gratitude Journaling: Resources for Those Who Prefer Keyboards to Pens

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My best friend has the most beautiful handwriting.  It’s flowy and pretty and easy to read.  She loves to send cards and letters the old fashioned way, so for years I’ve been the lucky recipient of some of the most beautifully penned thoughts and sentiments.

I used to have beautiful handwriting.  But somewhere between grade school and college my handwriting slipped from award-winning to mediocre to hieroglyphic symbols.

“It’s like my brain moves too fast for my hand,” I say half-apologetically to the cashier as I furiously scribble out my check. “Believe it or not, I used to win penmanship awards in grade school.”

Sure, my horrible handwriting has had some consequences:

Text from irritated husband: “I can’t make out the grocery list. You want eggs, milk and what?”

Me (equally irritated):  “Bread, honey.  It says bread.”

But for the most part, the only person this flaw has affected is me, and in pretty minor ways.

Recently, though, I’ve been hearing more and more about the benefits of daily journaling.  Research ‘morning rituals of successful people’ and you’ll likely find that most of them incorporate some form of journaling in their daily routine (whether it be morning pages, gratitude entries or just a free flow of thoughts).  The following are some of the most commonly reported reasons for keeping a journal:

  • to clarify thoughts
  • to dream big
  • to set goals and intentions
  • to track and monitor progress
  • to become self-aware (through honest reflection)
  • to preserve mental energy (by expelling ideas and thoughts onto paper)
  • to express gratitude
  • to improve writing skills through the daily exercise of writing

(I highly recommend this article on Medium: How I Use My Journal to Create My Future and Achieve Goals by Benjamin Hardy)

It didn’t take me long to see the benefits, and I soon began drooling over which moleskin journal I would select to start chronicling my journey to success.  I imagined myself in a coffee shop writing life-changing affirmations in bold, black ink, reminding myself of who I am and who I’m working to become.

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And then I remembered my handwriting.

Rather than be stymied, I did what any self-respecting writer and former paralegal would do, I hit up Google:

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Fortunately, Google also serves as my spelling and grammar police:
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Why, yes.  Yes, I did.

Google’s corrected search produced the following page one results:

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My personal favorite:
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Now, I’m a huge self-improvement advocate, but I’m not gonna lie, my handwriting is not on my list of Top 10 things to work on right now.

So I did some more research and found several online journaling resources. Here are a few, including brief descriptions of each in their own words:

Penzu
“Whether you’re looking for a tool to record your daily emotions and activities in a reflective journal, keep track of milestones in a food diary or pregnancy journal, or even record your dreams in a dream journal, Penzu has you covered. Penzu gives you all the tools you need to focus on the ideas you want to preserve, rather than the process of writing itself.”

JRNL
“JRNL offers a unique and enjoyable journaling experience while providing innovative tools that you are going to love.”

Online Journal
“Online Journal gives you a very private and free place to record your thoughts, feelings and ideas. We have tons of journal topics to help you get started. You can use it as frequently or infrequently as you would like.”

Five Minute Journal App
“There are plenty of benefits to journaling, whether you take time to write out your full thoughts or just spend a few minutes jotting down the things you’re most grateful for every day or lessons you’ve learned. The Five Minute Journal app makes this process easy enough to do on the go.”

All of the above are ways to record your thoughts online in a private way.  Of course, you can simply create a private blog.

You don’t need anything fancy.

In fact, my current online journal is simply a running Google doc in Google Drive.  Here’s the beginning of an entry from last week:

2018-09-14 Post - Snippet 5 (gratitude)

Nothing fancy.  It’s simple and uncomplicated.  I’m not limited in length.  I can copy and paste quotes, pictures, meaningful e-mails.  I can access it from anywhere.  I can print it off whenever I want to — even when it’s 300 pages long.  I don’t have to worry about losing it, or not having it when I want to journal. I can create a back-up or copy with ease.  And, most importantly, I can look back at my entries and actually read them.

I wasted weeks thinking about journaling, but once I convinced myself that it wasn’t “fake” journaling to type my thoughts into the computer, I started journaling right away and have been doing so almost every day since.

There is still something so beautiful and classic about manually penning your thoughts and dreams into the pages of a notebook or journal.  After all, it’s been the primary means of expression for hundreds of years.  I suppose I’ll have to comfort myself with the knowledge that methods of self-expression have evolved since the beginning of time, and the importance is less in the mode, but in the expression itself.

Takeaway:  If your handwriting isn’t the best, or if you simply prefer typing to handwriting, check out some of these online journals, start a private blog, or just open a new Google doc and start journaling today.

Ditch any feelings that you’re not “doing it right”.

You’re 100 times more likely to stick with something if you choose a method that works for you.

Resources:

How I Use My Journal to Create My Future and Achieve Goals by Benjamin Hardy
Source: Medium (9/16/17)

Five of the Best Sites for Creating an Online Journal or Diary
Source: Blogging.org (1/18/18)

The 10 Best Journaling Apps for 2018 by Melanie Pinola
Source: Zapier Blog (1/4/18)

8 Reasons Keeping a Journal Can Help You Reach Your Goals by Joshua Becker
Source: Becoming Minimalist Blog

How to Become Ridiculously Self-Aware in 20 Minutes by Tom Kuegler
Source: Medium (5/29/18)

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Your Thoughts Will Make You or Break You

Post 8 - Your Thoughts Will Make You or Break You (Blog)Starting a freelance business is both exciting and terrifying at the same time.

I’m not talking about one foot in and one foot out– I’m talking full commitment, like ready to do whatever it takes to make this thing happen.

When you’re at this point, you will find quickly find that it’s your thoughts and your thoughts alone that will ultimately make you or break you.

You will ride highs – my website is up! my first post! my first follower!

You will ride lows – what was I thinking? what if I can’t get clients? what if I get a client?

And every hill and valley in between.

You will start reading and watching everything you can get your hands on to help you succeed.

Despite all you’ve learned, you will occasionally despair over all you still don’t know.

In the past, my thoughts were always my downfall — not my skill level, not my ability to learn and master new skills — but my own self-limiting thoughts.

While it’s common and normal to have moments of hesitation or fear, or even self-doubt, that’s not what we’re talking about here.

It’s the toxic ruminating and globalizing. It’s the endless cycle of telling yourself you’re not good enough. It’s the not letting yourself get too excited because maybe you’ve tried and failed in the past.

If this is you right now, take heed:

We are more than the sum of our past failures.

These are some things I do to keep the negative thoughts at bay:

  1. Post here honestly and regularly.
  2. Reach out and connect with other amazing people who happen to be writers.
  3. Do at least one measurable thing a day toward my freelance writing goals.
  4. Ask for help if I need it.
  5. Give myself permission to pursue my dream.
  6. Study the success paths of a few people in the business whom I admire and can relate to.
  7. Remind myself of number 5 often.
  8. Picture myself a year from now.
  9. Picture myself a month from now.
  10. Picture myself when I’m 50.
  11. Picture myself telling my kids their dreams are possible if they’re willing to gut it out and do the work – and them believing it because they’ve seen me do it.
  12. Invest in myself by taking courses like this one with someone who’s been in my shoes so I can make money as a freelance writer faster.
  13. Read time-tested books on writing and copywriting so I can improve my technique.
  14. Listen to educational and motivational podcasts on anything I find inspiring: writing, entrepreneurship, taking action, rising from failures, psychology of success, self-love, making the most of this one life, etc. (I’ve compiled a list of my favorite podcasts here)
  15. Tell myself repeatedly that reading and listening is no substitute for doing.
  16. Let myself have fun in the process.

Your turn.

Do you sometimes battle with negative self-talk? What kind of things have helped you move past these thoughts and stay focused on your goals?

Prioritizing the Actions that Will Lead to Your Goals

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Does this sound familiar?

You’re putting in a ton of hours to get your freelance business up and running, clocking in time before and after your day job, jotting down business ideas during lunch, maybe even getting out of bed in the middle of the night to tackle just one more thing on your to-do list.  You’re tired, but you feel good — as you should.  You’ve set your sights on big dreams and have been working like a boss to get things in motion.

But are you any closer to your goals?

For example, when I officially started this blog in July, I put my dream out into the universe: to make a full-time living as a freelance writer in a creative and sustainable way.  I started this blog to hold myself accountable.  In my first blog post, I set two very specific short-term income goals:

  • Milestone 1:  Hit $2,000/month by Christmas 2018.
  • Milestone 2:  Hit $5,000/month by one year (July 2019).

Because my goals are income-based, I should be focusing on income-generating actions. When you’re wearing multiple hats, though, it’s sometimes challenging to know which right action you should choose to do next.

It’s so easy to get hung up on all the little details you think are necessary to start and run a new business.  As a solopreneur, you do it all: building and maintaining your website, networking, marketing, and, of course, your paid client work.

The lesson I’m learning time and again, though, is the critical importance of prioritizing (and completing) actions that will help you reach your goals, and fitting in the rest of your to-do list when you can.

I mentioned in a previous post that my social platforms of choice were Twitter, Medium and Pinterest. I have been prioritizing my Pinterest graphics and boards because I know Pinterest marketing, if properly done, can be instrumental in driving traffic to my blog. So even though I know I should update and optimize my LinkedIn profile, it will have to wait until my Pinterest business account is fully set up and ready to go.

While tying content creation to Pinterest marketing is a long term traffic generation goal, I should also be prioritizing actions that will lead to income generation now.  I should be actively looking for leads and pitching ways I can help on a daily basis.

If pitching is a numbers game, then submitting ‘x’ number of pitches should yield ‘x’ number of projects (on average). Conversely, submitting no pitches at all will almost guarantee a yield of no income.

Bottom line: if I want to achieve my income goals, I need to prioritize the things that will generate income.

Being accountable may require uncomfortable reflection.

Sometimes you find yourself concentrating on everything other than the items you know will move the needle toward your goals, and then you find yourself over-justifying your choices.

When I find myself over-rationalizing something I’ve done or not done, it’s often a sign that I’m letting myself off the hook for something important, and it’s likely rooted in fear.

That’s the time to break out your journal and start working things through until you get to the source of your behavior.  It would be easy to keep justifying and rationalizing why you’re not doing the hard thing you need to do, but doing so solves nothing and just prevents you from moving forward.

As we all know, inaction is where dreams go to die.

I’ve gone this route before.  It’s a lonely, soul-sucking, confidence-killing journey, and to think it could have been prevented by just taking action.

2018-09-03 Post (Photo #2) rawpixel-303966-unsplashSo when you get that familiar sensation that something’s off, or that you’re spinning in circles, trust your gut.  Step back for a minute and assess your actions objectively, with honesty and compassion — as you would for a friend. Then hold yourself accountable.

Accountability to yourself is as much about self-honesty as it is staying laser-focused on your goals.

Ask for help.

To a person building what seems an intangible dream, it’s sometimes easy to miss the forest for the trees. And sometimes if you’re too far gone, you can’t see your actions for what they really are.

Having someone you trust and respect check you and hold you accountable during these times is invaluable.  

Fortunately, I have people in my life who’ve been exactly in my shoes and get what it is I’m working hard to achieve.  And because they’re further along in their journey than me, they can sense the spinning when they see it.

Sometimes the quickest way over a stumbling block or setback is to seek outside help.  Reach out to a supportive online community like this one or hire a business coach you trust.

Whatever you do, recognize your fear-based behavior for what it is, and take action to move past it.  Every time you do, you’ll gain confidence in your ability to face the next obstacle.

Some help if you’re paralyzed by inaction

Sometimes you listen to something so powerful that you just want to share it with everyone.  I recently started listening to Amy Porterfield’s Online Marketing Made Easy podcast (highly recommended by Heather Deveaux of The Freelance Writing School), and I was blown away by this episode below:

If you can listen to the podcast, great.  I think you’ll learn a ton of valuable stuff — likely about yourself.  If you can’t listen but would love to know more, Amy posts a condensed summary of each episode (show notes) on her website. The show notes for the above episode can be found here.  She also includes downloadable transcripts of each episode at the end of her show notes.

For those of you who don’t know, Brooke Castillo is a world renown life coach expert and has hosted her own podcast (The Life Coach School Podcast) for years.  She talks about the power of mindset, and how changing how you think can help you achieve different results.  Interesting fact: Brooke launched her podcast several years ago. The title of her very first episode? Why You Aren’t Taking Action

If you need more motivation…

We can always learn from those who’ve gone before us.  I’ll leave you with these quotes from two people I greatly admire and respect:

Nelson Mandela: “It always seems impossible until it’s done.”

Eleanor Roosevelt: “You gain strength, courage and confidence by every experience in which you really stop to look fear in the face…You must do the thing you think you cannot do.”

Photos via Unsplash

How Podcasts Can Help With Mindset and Productivity [Including My Top Recommendations]

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I’ve written about my love of podcasts here, here and here.

They enable you to continue your career and self-development journeys and tackle the non-business things that need to get done in real life.

Those career-inspiring stories you’ve spent hours reading on your laptop?  You can catch those on podcasts.  Those writing and marketing posts you’ve been devouring?  Yep, there’s a podcast for that.

With over 500,000 podcasts on Apple Podcasts alone, there’s literally a podcast for everybody, in every genre.

Chances are, some of your favorite bloggers and writers have their own podcasts, or at the very least have been interviewed on one.

Another plus? The podcast medium is more flexible, which means those motivational interviews and stories can get really deep.

So while sometimes I’d love to have just another hour or two on the computer, a forced break can be rejuvenating.  Plus:

Podcasts help me get things done.

→  While folding laundry, I can learn exactly how to start a freelance writing business.

→  While whipping up a stir-fry, I can learn ways to overcome fear and self-doubt.

→  While doing dishes, I can listen to empowering stories of every day people like you and me who’ve pushed past great obstacles to create the lives they love.

When I’m cooking or cleaning, I like to connect my phone or iPad to this portable bluetooth speaker. That way I can hear the podcast over the sounds of cooking (or my kids) and, if needed, carry the speaker with me from room to room.

What’s more, when I return to my computer, I can resume my work with a feeling of accomplishment and a freer conscience.

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I use travel time for self-development as well.

I’m in my car for about an hour a day.  If I’m driving alone or just waiting for my kids, I’ll look for podcasts that address my specific needs or worries at the time, whether it be online marketing, social media, or help with SEO.

If I’m in my car, I’ll put my phone on speaker and place it in the cupholder or on the console so I can listen hands-free. Some people like to pair their phones to their cars via Bluetooth so they can listen through the car speakers.

Cool tip: Don’t have a portable speaker? Try sticking your phone inside a large cup or bowl. While not as good as a speaker, you’ll be amazed at the boost in volume. Placing the phone speaker sound down allows the audio to bounce off the bottom. For other cool DIY speaker tips, read this article from Cnet.com.

Need a break from self-improvement?

Maybe you want to use the time away from the screen to break free from work-related topics or self-development.  Maybe you’d like to laugh, listen to sports talk, or find out what’s in the news.

There’s a podcast for that, too.

If you’re new to podcasts or maybe don’t exactly know what’s out there, Concordia University-St. Paul created this really interesting infographic called the The Podcast ExplosionIt gives great insight as to the demographics of the listenership, how and why people listen, and what they’re listening to.

View the It’s a Podcast Explosion infographic from Concordia University St. Paul Online
Source: Concordia University- St. Paul

But the most important reason I listen to podcasts?

Mindset, pure and simple.

They remind me to embrace growth mindset versus perfection.

They remind me to use failure as a stepping stone.

They remind me that true success means sharing– that rising tides lift all boats.

They remind me that all success stories begin with that first courageous action.

They remind me that everyone is afraid–no one feels they always know what they’re doing.

They remind me that nothing is scarier than a lifetime of regret.

Your turn.

Would you like to try a podcast, but aren’t sure where to start?  I created a tab called Podcasts I Love with a list of my favorites.

If you’re already a podcast fan, what are some of your favorites?  Recommendations from colleagues are some of the best ways to learn about amazing new resources.

Podcast Spotlight: The Freelance Writing School Podcast with Heather Deveaux

Post - Podcast Spotlight - Freelance Writing School with Heather DeveauxNow that I’ve made the decision to seriously pursue a freelance writer career, I need to set up my shingle, so to speak.

I know I can write, but establishing a business framework and prospecting for clients is not yet in my wheelhouse.

I want to give myself the best chance for success, so I’ve been doing a ton of research on the steps I need to take to launch my business professionally, and as quickly as possible.

There are a gazillion online courses out there offering to teach these very steps.  Many are fair to modestly priced, but some can be pretty cost-prohibitive for those just starting out.

I bookmarked one such writing course for the future.  While the $197 price tag is well below others I’ve seen, it’s more than I’m comfortable spending right now on self-development.  I know it will be worth every penny, though, so I’ve decided to use it as an incentive.  I will only purchase the course with funds earned from writing, and only after hitting the $1,000.00 mark.

Until then, I’ve been taking advantage of the wealth of knowledge shared freely in the podcast world.  I listen to podcasts on self-improvement, motivation, entrepreneurship, and freelance writing, just to name a few.  It’s like having front row seats to networking or marketing conferences I can’t yet afford.

Often, I’ll set up a podcast on my phone and immerse myself in topics ranging from SEO, blogging, and Pinterest marketing, to the hard-fought paths to success of some of the most heralded entrepreneurs, all while running errands, washing dishes and folding laundry.

It was while searching for ‘freelance writing’ podcasts that I stumbled upon The Freelance Writing School Podcast (aptly named).

For those of you who have long nurtured a dream to make a living writing but have been too scared to start, I strongly encourage you to listen to The Freelance Writing School Podcast with Heather Deveaux.

It will inspire you to stop overthinking, push past your fears of failure and start moving toward your dream today.

I have listened to countless podcasts over the past year but never left a review — until now.  Below is my five star i-Tunes review of The Freelance Writing School Podcast:

Want to stop procrastinating and actually create the career and life you’ve always dreamed of? If so, you have to listen to The Freelance Writing School Podcast with Heather Deveaux, read her blog at HeatherDeveaux.com and watch her You tube videos.

Heather is unabashedly transparent about her former life (endless starts but never finishes, being quick to quit when things got too real or uncomfortable).

But in 2016, she had enough and decided to take action to change her life. She set out to lose weight and has since lost and kept off 80 pounds. Just in the past year or so, she launched a full-time freelance writing career (earning more than her former desk job), a podcast and YouTube channel to share her incredible freelance journey with others, and The Freelance Writing School course to teach others step-by-step how to launch their own freelance writing careers.

Yes, her language is colorful, but that’s because she is being her true, authentic self. Her down-to-her bones passion is teaching and helping others move past their own self-limiting beliefs to achieve their own version of success.

The one takeaway from everything Heather teaches? “If I can do it, you can, too, if you’re willing to get out of your own way, do the work needed, and enjoy your failures and successes along the way.”

Be ready to really dig in, analyze what’s holding you back, and move confidently and fearlessly toward your dreams.

If you’re paralyzed with self-doubt, this podcast is for you.

If you feel your previous failures will hold you back, this podcast is for you.

If you’re tired of all the years you’ve wasted not living the life you’ve always wanted, this podcast is definitely for you.

Plenty of podcasts offer great advice on creating successful freelance writing businesses.  But I find many of us aren’t quite there yet.  It’s hard to focus on being even more successful if you’re still stuck on how do I just start.

That’s where The Freelance Writing School Podcast comes in.  If you’re the type who talks yourself out of your dream before you even start, or you’ve finally committed but are overwhelmed by the next steps, Heather Deveaux walks you through each phase.

She knows what we’re struggling with because she’s been exactly where we are. 

I was thrilled to learn that she had just launched a course (How to Confidently Start and Run a Freelance Writing Business), and that it was reasonably priced (only $75 U.S. dollars).

If you’re interested, I’ve included a link to her course description (see above).  Please know that I am not an affiliate, nor do I receive any compensation if you purchase her course.  I’m just a big fan.

These are some of the things you will learn from her course:

  • How to deep dive into mental barriers that may hinder your chance for success (and what to do when they arise)
  • Setting up your business (accounting needs, project management, e-mail marketing, etc.)
  • Identifying your niche market
  • Setting rates
  • Setting up your website and social media accounts
  • Creating writing samples, maximizing samples for SEO

I am currently working through the self-paced modules and have learned so much already.  The course is definitely worth every penny.

Even if you don’t purchase her course, be sure to check out her podcast, her YouTube videos and her personal blog at HeatherDeveaux.com.  She shares so much valuable information on how she makes money as a freelance writer, for free.  

Just as valuable, however, are her deep dives into her own self-improvement journey.  She is not afraid to lay herself bare as she tackles her own occasional self-limiting beliefs.

Which leads me to…

Why do I want to freelance? (Revisited)

I know I touched on this in my first blog post, but after working through the first steps of The Freelance Writing School course, How to Confidently Start and Run a Freelance Writing Business, I came up with a more substantive list:

  • To be able to work and travel – independently and with my family
  • To realize financial goals I never thought possible
  • To build a nest egg so I can facilitate my dream of traveling
  • To help people (still working through how I can best serve)
  • To inspire my girls to think outside the box and to never stop showing up in life
  • To know that if everything falls apart I have the wherewithal to build it all back up again
  • To be open and authentic
  • To spread hope and possibility to others
  • To learn the power of consistency and showing up daily in dogged pursuit of my goals.

Top 5 Reasons to Hire a New Freelance Writer

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Newbies are motivated to get started.

Newbies know that nothing will kickstart their freelance career more quickly than a portfolio of solid writing clips. But how do newbies start building their portfolio if most places won’t hire without one?

Motivated newbies don’t let others dictate their future. They know they’ve got writing chops. Rather than wait to be hired, they find creative ways to get their work in front of prospective clients.

Newbies are eager to build their reputation.

Newbies didn’t just wake up one day and decide they want to be a freelance writer. Chances are, that’s a dream they’ve been nurturing for years. So when they finally do take the plunge, newbies are all in and eager to get their foot in the virtual door.

To showcase their talents, they will cover all sorts of topics, such as: ‘Why Your Teen is Obsessed with Snapchat and Tumblr’, ‘Why Completely Random Stock Photos Are Still Good for Your Traffic’, ‘What Fido is Trying to Tell You With His Tail’, ‘The Importance of Breastfeeding and Why It’s Still a Touchy Subject for New Moms’, ‘Raising Kids In a Politically Divided House: How to Engage in Appropriate and Respectful Debate When Your Spouse Insists on Supporting the Wrong Candidate’.

Newbies know that reputation is gold in the freelance world. You can bet they will hustle to establish themselves as valuable contributors by producing awesome, buzzworthy content.

Newbies are research hounds.

Newbies are not afraid of what they don’t know. The digital era has leveled the playing field, and they use it to their advantage. Blog posts, articles, web content, newsletters, books, podcasts, videos. The sheer vastness of the resources available can be overwhelming, but newbies are research ninjas. They are deft at cutting through the noise and finding just what they need to craft compelling, thoughtful content for your website or business.

Newbies are sometimes sea glass disguised as newbies.

I know, say what? Bear with me.

Newbies routinely sell themselves short, often without realizing it. Consider this pitch:

Hi, I’m Newbie. Although I’ve never written anything yet in the B2B field, I have years of experience working with lawyers and doctors in the medico-legal field. I’m confident I can pick up the lingo and write your B2B sales copy in a way that will help you get the results you’re looking for.

 Newbies are surprised when this pitching style does not ‘make it rain’ for them.

Let’s read between the lines:

The newbie** in the above example may not have actual B2B sales copy experience, but she did spend over a decade as a medical malpractice paralegal helping defend doctors and hospitals against all sorts of allegations: delays in diagnosis of cancer, loss of limb(s) due to compartment syndrome or diabetes, complications from necrotizing fasciitis, negligent spinal fusions, cerebral palsy and/or shoulder dystocia due to birth-related trauma.

** Based on author’s true story.

Was this newbie a doctor or nurse? No.

This newbie started in the mailroom of her law firm, worked her way up to legal secretary, and, within a year, was promoted to medical malpractice paralegal.

Did she have any special medical training? Surely she must’ve known about CPAP machines, tumor markers, fetal monitor strips, subdural hematomas, and lumbar laminectomies before diving into this position. Again, no.

 In fact, she had to look up the Merriam-Webster audio pronunciations of countless medical terms just so she could say them correctly in client meetings.

What made this newbie think that with absolutely no medical training or experience she could serve as the right arm to defense counsel defending complex, often life and death, medical issues? The better question might be, what made the attorney she worked for so confident she would succeed?

Determination and dogged research skills (and though the attorney would be too humble to say, the invaluable experience she received under his mentorship).

What this newbie lacked in experience, she more than made up for with her exhaustive research skills. She pored through industry journals, online resources and, yes, even Google, to bring herself quickly up to speed so she could write compelling (sales) arguments (copy) on behalf of her medical (B2B) clients.

In essence, this self-proclaimed newbie spent years writing copy in the medico-legal niche. And if she can excel in this complex field, she can use the same skills to excel in other niches.

Of course, in a textbook example of how we often subconsciously undermine our own value, none of this comes through in the newbie’s pitch.

If she reframes her expertise, prospective clients will see that she’s not a newbie at all, but sea glass — shaped and polished by years of experience into something of great value.

You were once a newbie, too.

The thing is, all experienced writers, marketers, entrepreneurs, etc., were once newbies. All anybodies were first newbies before hitting their stride: Steve Jobs, Warren Buffet, Shonda Rhimes, Richard Branson—even the President of the United States. To be clear, anyone making their first Presidential bid is asking voters to accept that their background and experience qualifies them to do something they’ve never done before.

While comparing freelance writing to running one of the largest democracies in the world may be a bit of a stretch, you get the idea.

Yes, I see that you do, because you were once a newbie, too.

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.