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barefootWriter
Celebrating 12 Years of Helping People Find Freedom Through Well-Paid Writing
Issue 146  October 2023
Side Hustle Nation founder Nick Loper reveals exactly what 
it takes to make extra money and build a business you love
in this issue
FEATURES
 5 Living the Writer's Life 
 Dave Sharpe and Jen Phillips April escaped the same 
 problem with vastly different takes on writing
 9 Interview with a Barefoot Writer 
 Nick Loper reveals the secret to claiming lasting control 
 over your time
17 Featured Essay 
 The Rat Race, Defined
23 Barefoot Writing Opportunity 
 The Best Writing-Based Side Hustles for Extra Money 
 in Your Pocket
DEPARTMENTS
 3 What You’ll Learn In This Issue 
 Window Through the Box
28 Glicken 
 5 Tips for Enjoying Fun and Profitable ‘Workations’ All 
 Over the World
31 Mobile Freelancer 
 Living the Barefoot Writer’s Life in the Tropics
33 Become a Better Writer 
 8 Simple Steps to Crafting the Perfect Sales Letter
36 Ask AWAI 
 How to make meaningful connections with other writers, 
 and which social media channels to invest your time in… 
 Rebecca and Katie answer your questions
37 The Barefoot Writing Challenge 
 Describe what your city or town looks like during the 
 month of October
ABOUT OUR COVER: 
Nick Loper is the founder of 
Side Hustle Nation and host 
of the award-winning Side 
Hustle Show. In his quest for 
both control over his life and 
financial freedom, he built the 
Side Hustle Nation community 
by sharing stories about his 
experiments along the way to 
successful entrepreneurship.
barefootWriter • Page 2 • October 2023
what you’ll learn this month
Window Through the Box
There’s a famous sales letter for International Magazine that begins 
with this: “You look out your window, past your gardener, who is 
busily pruning the lemon, cherry, and fig trees… amidst the splendor of 
gardenias, hibiscus, and hollyhocks.”
It goes on to paint the glorious picture of living in a paradise that is 
about half the price of what it probably costs you to stay in your own 
home right now.
Far-fetched? Not at all. In fact, this entire issue of Barefoot Writer is 
devoted to showing you how others have used writing to achieve this 
type of paradise-laden living. Jen Phillips April (p. 7) and Jason Gaspero 
(p. 28) have made this kind of move permanent.
But then there’s also the other side, which is that you don’t have to 
relocate to a tropical beach to enjoy a superb lifestyle. Dave Sharpe (p. 5) 
shows us how he’s achieved contentment while staying put in his long-
term home. 
And then Featured Interviewee Nick Loper (p. 9) brings us the best of 
both worlds with his devotion to the art of the side hustle and his de-
piction of how he takes advantage of the benefits by traveling far and 
wide and for long stretches. 
The thing all these stories have in common is that they started as side 
gigs, stemming from the somewhat common feeling among adults of 
being underwhelmed and underfinanced by their work. But rather than 
stay confined to the box that made them miserable, they cut a window 
and let the light of possibility stream through — and then followed that 
light to writing for a living. 
To help you do the same so your own escape to happiness is quickly 
achievable, we’ve rounded up the top five writing side hustles so you 
can get started on this trajectory toward greater long-term satisfaction 
(p. 23). Choose one and go with it. Based on the real-life stories in these 
pages, you won’t regret it!
Thanks for being part of this world with me,
Mindy McHorse
Executive Editor, Barefoot Writer
mindy@barefootwriter.com
Barefoot Writer Executive Editor 
Mindy McHorse
Published by:
American Writers & Artists Institute
220 George Bush Blvd Ste D
Delray Beach, FL 33444
Publishers: 
Katie Yeakle and Rebecca Matter
Executive Editor: 
Mindy McHorse
Layout:
Mike Klassen
Copy Editor:
Laurel Robinson
Questions? 
Contact Member Services: 
www.awai.com/contact
866-879-2924 or 561-278-5557
© American Writers & Artists 
Institute, 2023. 
All rights reserved. 
Protected by copyright laws 
of the United States and 
international treaties.
Selected photos from 
Bigstock, Fotolia, iStock
barefootWriter • Page 3 • October 2023
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featured contributors
Challenge Prompt: Describe what your city or town 
looks like during the month of October.
When people ask Jason Gaspero (“5 Tips for Enjoying Fun and Profitable ‘Workations’ 
All Over the World”) “Where are you from?,” he has a bit of trouble answering the ques-
tion. That’s because Jason, a self-confessed vagabond, has lived in eight states and 11 
countries. Today, he calls the idyllic tropical island of Koh Phangan, Thailand, home. 
When Jason isn’t writing copy or studying digital marketing, he enjoys photographing 
the island’s exotic wildlife, feeding the local street dogs treats, and practicing his Thai 
cooking skills.
It’s still “monsoon season” on Koh Phangan in October, so there are often 
torrential downpours and massive puddles to deal with!
Jen Phillips April (“Living the Barefoot Writer’s Life in the Tropics”) was a museum 
educator at Pennsylvania’s historic sites for seven years. When budget cuts ended her 
role, she launched her copywriting business. Her portable income inspired her to move 
to Mexico’s Caribbean in 2017. Now she offers content strategy and writing for global 
B2B clients. In her off hours, she loves searching for the best tacos.
It’s the tropics, so October means a few degrees cooler than the sweltering 
summer heat. Toward the end of the month, you can see marigolds and family 
photos at area altars to remember the ancestors in honor of the upcoming Day 
of the Dead.
Craig Grossman (“8 Simple Steps to Crafting the Perfect Sales Letter”) is a StoryBrand 
Marketing Guide. He loves helping his clients by creating brand narrative strategies, 
compelling website content, and sales copy for local and national companies. His favor-
ite niches include financial planners, accounting firms, B2B, and professional services. 
Check out his “StoryBranded” website. Craig and his partner, Hope, have a home and 
large vegetable garden in Spokane, Washington, and love to hike, ski, and paddleboard.
Spokane really shines in October! Although our native forests are full of 
evergreens (ponderosa pines and Douglas firs), our city streets and parks are 
filled with a variety of old deciduous trees that turn into vibrant colors all 
October long.
barefootWriter • Page 4 • October 2023
https://fabulouscopy.com
living the writer’s life
Mindy McHorse Talks to 
Barefoot Writers From All 
Walks Of Life
Bored, ‘Bad Employee’ Becomes Calm, 
In-Control Writer
Self-professed “bad employee” Dave Sharpe desired nothing more than control within his 
own life. When a piece of sales content caught his eye, he discovered how writing might 
be the key to his escape. Read on to learn how he transitioned from always wanting more to 
being the head of his own writing agency in a trajectory that’s changed not only his life but 
the lives of those closest to him.
Take me back to life before writing. 
I’ve worked in a wide variety of jobs, and I was a bad employee in almost all of them. 
I had too many ideas, and I couldn’t stay focused on the mundane part of my job. I 
wanted to have more control over my time and income. I 
wanted to be the boss. I wanted the flexibility to choose 
when I wanted to work and when I wanted to pursue my 
other interests.
You’ve hit on the major pain points most Barefoot 
Writers feel before they make the leap. How did that 
lead you to become a writer?
I was working with an import-export catalog company. 
One day I saw a product that we were marketing. I looked 
at the sales letter and I said, “Oh, I can do better than that.”
So I started picking away at it, and about halfway through 
I realized, “No, I can’t do better than that.” I discovered I 
was gettingto 
program and use our DualMode Automated Forklifts? 
Let’s schedule an online demo — where you can learn 
how the automation features work and get your ques-
tions answered by Troy Nickerson, our product engineer.
Or, if you’re convinced that our DualMode Automated 
Forklift is precisely what your warehouse needs to save 
money and increase efficiency, go to our order page, 
where you can view pricing options and place your order.
6. Paint a picture of success: Show them what their life could look like if they bought 
your product. Not only will they overcome their problems, but they’ll be happier.
Imagine how delighted your management team will be when they see the payroll sav-
ings created by “employing” your new DualMode Automated Forklifts. And you’ll become 
the “hero,” with forklifts that are involved in fewer accidents on your warehouse floor.
7. Repeat the call to action: Use the same CTA you included earlier in the sales let-
ter. To spice it up, you could add some failure language describing what happens if 
they don’t buy your product. In other words, completing this CTA can lead to pain 
avoidance.
So, your choice is clear. You could continue “business as usual” and spend a lot of dough 
on forklift operators.
Or — click on our order page and order our new DualMode Automated Forklifts and 
lower your payroll costs today!
barefootWriter • Page 34 • October 2023
become a better writer (continued…)
Don’t worry: You’ll receive a three-year warranty too. If anything goes wrong, we’ll fix 
your DualMode Forklifts at no charge.
8. Include a P.S.: Use this space to include a limited-time offer after your signature. You 
will achieve higher conversion rates if there is an expiration date on the offer.
P.S. If you order a DualMode Automated Forklift in the next 10 days, you’ll receive FREE 
TRAINING for your team. So don’t procrastinate — order today!
Feel free to move the sections around to make them work better for your client’s 
specific product or service. Or even leave out some sections if it will make the letter 
stronger.
If you use this sales letter formula to increase your client company’s sales, not only will 
it help your client, but you’re also likely to get repeat business from your clients and 
more referrals. ¢
Free Live Training!
The 3-Phase Blueprint for Building a Thriving, 
ZERO-CLIENT Writing Business 
(And Making a TON of Money as Your Own Client)
** October 12, 2023, at 2 p.m. Eastern Time **
As a copywriter, you have a financially valuable skill that can be used to make money in 
numerous ways for the rest of your life. 
Some of the money comes from clients, but a far greater amount (we’re talking seven 
figures!) can come from clientless revenue streams that don’t require your hours in 
exchange for dollars. 
Join AWAI Learning Chief Pam Foster and AWAI President, Rebecca Matter for a power-
ful training that will show you the three-phase blueprint for building an asset that 
will pay you for years to come… all with zero clients. 
Click Here to Save Your Spot
barefootWriter • Page 35 • October 2023
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ask AWAI
As managing partners of AWAI, Katie Yeakle and 
Rebecca Matter have guided, motivated, and 
celebrated thousands of Barefoot Writers over 
the years. Got a question for them? 
Send it here: info@barefootwriter.com
Q: How can I make meaningful connections with other writers? I keep hearing 
that’s going to be my best support network, but I don’t know how to make 
it happen. 
Rebecca Matter: Showing up as yourself, authentically and vulnerably, is 
the most powerful way to make connections with other writers. Be curious, 
ask questions, and show interest in what others are sharing online during 
Zoom webinars, on Facebook, and on any other social media platforms. 
Also make sure you’re doing your part to contribute too… sharing your 
experiences, taking the time to answer questions when you can, applauding 
other writers’ successes, and offering support where appropriate. 
As far as where to go, your best bet is the Barefoot Writer Member Facebook group, 
since it’s private and limited to fellow writers who share your aspirations. I encourage 
you to post and comment regularly there. 
In addition, AWAI hosts Zoom webinars almost every week where writers are invited to 
contribute or ask questions. (You can see the full calendar here.) Any time you get the 
chance to speak and share, take it. Odds are, someone else will start seeing your name 
regularly and you’ll see theirs, and you’ll forge an organic connection — which are the 
best, most long-lasting kind in this business.
barefootWriter • Page 36 • October 2023
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ask AWAI (continued…)
Q: How important is it to be on all the different social media channels now 
that I’m working to be seen as an “online professional” through my writing 
business?
Katie Yeakle: That really depends on two things: whether you want to be on 
a social media channel, and whether a specific social media channel is rel-
evant to the industry you’re writing for. That said, it’s smart to set up a basic 
LinkedIn profile no matter what industry you write in. It’s free, and it really 
stands as a proof piece and resume for your professional writing skills.
As for the rest of the social media channels, consider where your potential 
clients hang out. If you want to write for the B2B market, stick with LinkedIn. If 
you’re targeting the self-help market, a lot of those companies have a large presence on 
Facebook. Tech companies have historically been based on X, formerly known as Twit-
ter. Lots of beauty and fashion companies are using TikTok. 
Once you figure out which channel makes the most sense for you, set up a profile there 
and interact with the brands and clients you’d most like to write for. Let the other chan-
nels go so you don’t spread yourself thin and lessen your impact. ¢
the barefoot writing challenge
Describe what your city or town looks like during the month of 
October. 
A check for $100 will be awarded for the winning essay!
Send entries to contest@barefootwriter.com by midnight ET on October 18. 
Please submit entries as a Microsoft Word attachment and limit your essay to 500 words or fewer.
Congratulations to Mary E. Ryan for winning the September Barefoot Writing Challenge! Here’s a 
glimpse at her essay:
My golden birthday was when I turned 23. I was in the middle of a Saudi 
Arabian desert, serving in the United States Army. We were caught in a 
once-a-century flash flood, and I spent the day digging trenches to drain 
the desert. Perhaps not the most fun birthday — definitely not like the 
year I turned 6 and my parents threw me a surprise birthday party — but 
certainly a very memorable birthday.
That year went on with highs and lows. A most notable high was return-
ing stateside to be reunited with my husband on our first anniversary! 
A notable low was returning with lung damage that ended my military 
career.
Click here to go to the Barefoot Writing Winners Page and read her inspiring copy. 
barefootWriter • Page 37 • October 2023
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	in this issue
	what you’ll learn in this issue
	featured contributors
	living the writer's life
	interview with a barefoot writer
	featured essay
	barefoot writing opportunity
	glicken
	mobile freelancer
	become a better writer
	ask AWAI
	the barefoot writing challenge
	PWAan education as I was writing, trying to im-
prove this sales letter. From there I wrote catalog copy and 
miscellaneous copy for articles and ads. 
What do your writing projects look like now?
I do a lot of business communications process writing, as I 
call it. I’m also managing an agency, so I don’t get to write 
much stuff for clients now. Instead, I write proposals for 
Dave was invited to an international 
conference in South Korea to give 
presentations on SEO and copywriting.
barefootWriter • Page 5 • October 2023
living the writer’s life (continued…)
landing clients. I write proposals for landing donors for nonprofit organizations. I write 
standard operating procedures. I get to do a little bit of training writing. Yesterday I 
wrote a prompt-writing training session for my writers for AI.
How did you come to be in charge of an agency? 
After I started learning direct-response copywriting, I picked up the Circle of Success 
membership. This was about 2010, and I was starting to work my way through a bunch 
of the courses. I answered an ad for a writer, and the guy that I ended up working with 
owned a midsize company. I was talking to him about some of the content marketing 
gaps that he had, and I did a site audit for his website. He liked it so much that it actu-
ally turned into a content development contract and $100,000 a year to write content 
for the website. 
That was going so well that we decided to launch an 
agency to provide these services to other businesses. 
Now I’ve got 30 team members and they’re scattered all 
over the world. We provide SEO and content marketing 
services for clients.
You went from a tiny interest in writing to running 
your own agency. What was your biggest challenge 
in getting there?
I really struggled with the idea that writing would work 
for me. And moving from that point to taking action was 
really difficult. I poked at this with a stick. I would do a 
little job here and a little job there, and I’d barter a little 
bit, but I didn’t ever really think I could take it beyond 
that point. Believing that it would work for me was prob-
ably the biggest challenge. I’d tell writers new to this 
world to put the stick down. Quit poking it with a stick 
and just get busy.
How has working for yourself and writing for a living 
changed your life? 
It’s changed my ability to support my family and worthy causes. My income has tripled 
since I started this path 11 years ago. And as a result, my wife was able to quit her job 
and homeschool our son. When her father was diagnosed with a terminal illness, we 
moved across the country and helped with his care, and we didn’t have to worry about 
getting jobs when we relocated. Recently my wife was able to go to Europe for two 
weeks. My son’s in university, and we’re able to provide the education and the extra-
curricular, supplemental types of things he needs.
If the car happens to break down, I don’t have to worry about it now. There’s responsi-
bility that you have to keep in mind, but it is not the dramatic crisis that it used to be.
Dave reports that his desk is “mostly cleaned off” 
on a really good day. 😊
barefootWriter • Page 6 • October 2023
living the writer’s life (continued…)
From Frigid Winters to the Caribbean 
Shoreline
When I spoke to her from her writing office in Playa del Carmen, where she’s been for 
six years, Jen Phillips April looked refreshed and sun-kissed. But that wasn’t always 
the story… Discover how she decided she’d had her fill of Pennsylvania winters and what 
brought about the glorious new writer’s life in the tropics that she’s enjoying now.
Before you found the writer’s life, what was it you were trying to get away from?
I had just finished my graduate degree in museum studies. I am a history nerd. I have a 
background in working in historic sites, and I was doing that while living in the suburbs 
of Philadelphia, where it is winter six months a year. I’m originally from South Carolina. 
I misgauged that. Somehow I ended up in that winter place. I was doing the commute 
and really hating life. I mean, I enjoyed my job well enough, but who likes commuting? 
That was just not my thing. So I was looking for something different. 
It was the early 2000s, and the internet was 
just sort of coming into being and blossom-
ing into something. And I started poking 
around online and learned about direct-
response copywriting and this whole world 
of digital marketing. And I was like, “I want to 
know more.”
How did you go from working in the mu-
seum to writing for pay?
I started a website about dog treats specifi-
cally in 2005. I learned SEO and affiliate mar-
keting, and I grew a list. I grew that website 
to 87,000 visitors a month. And I kept it for 
seven years, but I would just work on it at 
night or on the weekends. So it became really 
valuable.
Then I lost my job in 2010, which was basically 
the tail end of the fallout in 2008. We lost our 
funding and we closed. And it was January, 
the cold of winter. At this point, I had discov-
ered AWAI and was trying to figure this thing 
out. I remember sitting there in the corner of 
my room with my computer and going, “How 
will I make this work?” I mean, I was on unem-
ployment, nobody was hiring. It was a terrible 
time. The economy was in the dumps, and I’m 
Jen often heads down to the beach in the afternoon 
once her writing projects are complete.
barefootWriter • Page 7 • October 2023
living the writer’s life (continued…)
like, “Okay, this is my time. The universe has 
granted me this. What do I do next?”
That summer I started going to local network-
ing events, and I found out that I was a genius 
at internet marketing when I talked to local 
people, because they knew nothing about 
what I was talking about and I had all this 
experience from writing for the website seven 
years. I ended up working with local people, 
and that was kind of my first taste of it.
Fast-forward 10 years, what kind of writ-
ing do you do now?
I still work in the pet niche to some degree. 
I’ve written for Chewy and lots of pet insur-
ance companies and big names. But also in 
the last few years, I’ve started working a lot 
with B2B tech companies. I’m writing content 
and success stories about different software 
products. And I have been going deeper and 
deeper into the hospitality tech space, which 
is really interesting and fun. 
What was the biggest challenge in getting 
started, both with the pet site and your 
new niches? 
Having the confidence that you actually can 
do this, because there’s no one waving a 
magic wand. You just have to say, “Yes, I’m 
ready. I can do this.”
What is life like for you today as an expat? 
Being three blocks from the Caribbean Sea, I can just go to the ocean for an hour. And 
I go back to visit my family in South Carolina for extended time periods. A while back 
I went to New Orleans for five weeks to stay with my sister. And my partner and I just 
came back from pet sitting on the west coast of Mexico in this tiny town north of Sayu-
lita for six weeks at the most beautiful oceanfront property. All we have to do is pack 
up our computers and put them in a laptop and go. It’s possible to kind of create your 
life the way you want it to be. ¢
 
This coconut stand is a common sight 
on Jen’s walk to the beach.
barefootWriter • Page 8 • October 2023
interview with a barefoot writer
“An entrepreneur in motion 
stays in motion.” 
— Nick Loper, Writer and Founder of Side 
Hustle Nation 
By Mindy McHorse
Nick Loper was an entrepreneur from the start, from as early as Boy Scout candy 
sales to college house-painting jobs. So when he took the traditional route of get-
ting a safe, secure job with a giant corporation, it never felt quite right. 
That experience prompted Nick to reclaim his freedom, which began with a series of 
online marketing experiments. Through several twists and turns, that led him to found 
Side Hustle Nation, where today heserves as Chief Side Hustler and connects the 
growing community for aspiring and part-time entrepreneurs through the hundreds of 
paths he’s discovered that lead to job-free income streams. 
Nick has since authored The Side Hustle: How to Turn Your Spare Time into $1000 a Month 
or More as well as $1,000 100 Ways: How Real People Make Real Money on the Side (And 
How You Can Too), among other books. He also runs the award-winning Side Hustle 
Show and regularly connects with and encourages fellow writers and creators.
I spoke with Nick from his home in Issaquah, Washington, where he was just coming 
off a busy summer season of spending ample time outdoors with his family, thanks to 
a career that supports that flexibility. You’re bound to enjoy his explanation of “side 
hustle physics” and the importance of what he calls “the three Cs in life and business,” 
among loads of other wisdom nuggets.
barefootWriter • Page 9 • October 2023
interview with a barefoot writer (continued…)
Let’s go back to when you were first working for Ford Motors. You had the salary, 
you had the reliability, you even had a company car. Why did you want out?
I just never saw myself being the person to climb the corporate ladder, whether it was 
with Ford or with any other company. I always had in my mind that I wanted to do my 
own thing and just was not sure what that thing was going to be. But I knew there had 
to be an alternative path.
It was really about having control over my own time. I remember I first started the gig 
in June and it was this realization of never having summer break again. They moved me 
across the country. It was exciting, but at the same time, I thought, Oh, this is what it’s 
like to be a grown-up now.
Not what you thought it would be.
Exactly. I thought, This isn’t all that cool. I was on the East Coast and all my friends and 
family were on the West Coast, and I only had five days off because I started halfway 
through the year. And having to ask my boss for permission felt very juvenile. Teacher, 
can I go to the bathroom? He was never the person to say no. It wasn’t a tyrannical situa-
tion where we’d need to come in and work weekends and all that stuff. But at the same 
time it felt weird. I wanted to be in control of the calendar.
Did you spend your time saving up before you took the leap, or are you the type 
to thrive on pressure?
Yeah, the naivete of a 25-year-old or something. You’ve probably heard the quote — I 
think it’s a Reid Hoffman, founder of LinkedIn: “An entrepreneur is somebody who 
jumps out of the airplane and figures out how to build their parachute on the way 
down” or some variation of that. To me, that 
sounds terrifying, and some people need that. 
Burn the ships. I’m going to quit the job. I’m going 
to figure it out. Figure out how to make rent next 
month. Cool, if you need that pressure, fine. But 
I wanted to have a track record of revenue from 
a side business, which in my case was a compari-
son-shopping site for footwear. 
That was your first foray into the entrepre-
neurial world.
Yes, so that was the original side hustle. It pulled 
the catalog from Zappos, from Amazon, from all 
these other footwear retailers online and told 
you where to find the best price on your next 
pair of shoes. And I would earn a referral com-
mission for every sale that was referred through 
the site.
I wanted to get to where even if it wasn’t fully 
Side Hustle Nation was born out of Nick’s desire 
to take charge of his own time every day.
barefootWriter • Page 10 • October 2023
interview with a barefoot writer (continued…)
replacing the day job salary, it was at least covering my monthly expenses, my portion 
of the rent or my portion of the mortgage and all the utilities and the groceries and 
stuff. I had a little bit of a savings nest egg where, if everything blew up, we’d be okay. 
We wouldn’t have to take on credit card debt or anything like that for the next few 
months, but it was having a way to soften that landing or reduce the height of that cliff 
you’re jumping off, so to speak.
You had a plan to back your way systematically out of your 
day job without fully taking the leap.
Luckily for me, they weren’t paying me a ton and I was only two 
or three years into it. So I was like, Well I’m not married to this. I 
don’t want to climb this corporate ladder anyway, so here we go. 
It was still nerve racking to make the leap and to wonder, Can I 
really cut my own paycheck? Let’s see if this thing has legs, see if this 
works. I should add, too, the farther along you are in your career, 
the harder that is, because the salary increases, the connections 
build, and just the personal identity that you have wrapped 
up in that career, it all gets stronger and stronger. It becomes 
harder to walk away from. 
Your shoe comparison site was quite successful, but you 
also started a few other side hustles online, and many of 
them never took off. Where did you find the motivation to 
keep trying new things in the face of disappointment?
I feel like an entrepreneur in motion stays in motion. It’s like 
some level of side hustle physics where once you see an idea, 
you’re trying to spin off the next thing. I had a podcast guest de-
scribe it as, “Opportunities become visible once you’re already 
in motion.” So really the most important thing is taking that first 
step, because even if you don’t really know if that’s something you’d want to be doing 
long term, it’s the ideas that that sparks. It’s the conversations that you have along the 
way. That was what was true of all the other side projects on the side from the shoe 
business. 
One was a handbag and luggage site because a lot of the advertisers that I was work-
ing with for shoes, for footwear, already sold those. It was kind of a similar set of part-
ners to work with, but it didn’t go anywhere.
Then I started a sandal site to get even more niched down. My original theory was, 
Well, if I have shoes in the title of the website, it will appear to be more relevant for some-
body looking specifically for a shoe product. So more people would click on that than a 
broader link. That was the hypothesis to test. I was like, Well, what if I did sandals? That 
would be even more relevant than shoes. But I soon discovered it was a super-seasonal 
product, and at a lower price point, typically, than shoes and boots.
So that one didn’t work either, but a couple of the projects did have some traction. 
One of Nick’s goals early on in life 
was to “reclaim summer vacation.” 
He’s shown here kayaking in 
Washington state with his son.
barefootWriter • Page 11 • October 2023
interview with a barefoot writer (continued…)
One was a virtual assistant directory and review platform. It was called Virtualassistant.
com. Started in 2011, really born out of my own questions and curiosity and pain points 
around making some virtual hires. I was running the shoe business at that time, looking 
for some help to grow and scale it. 
Which really goes to show that a lot of great companies are born from experienc-
ing a need and working out the answer to it. 
Exactly. And it was a lot of fun to have a front row seat as that industry grew a ton over 
the next decade. Then the Side Hustle Nation project came a couple of years after that, 
which was kind of the transition of a personal blog that no one ever read because there 
was no cohesive message or theme to it. The podcast started at that same time. It was 
interesting because the podcast really got traction. I use the term “traction” pretty 
loosely, but it grew a little bit faster than the blog side, which was surprising to me 
because I thought of myself as a writer first and foremost.
In the TEDx Livermore talk that you gave, you 
spoke about how being engaged and inspired 
at work is something that an average of only 
about 30% of people get to experience. Do you 
think, post-pandemic, that people are giving 
more weight to needing that satisfaction?I think you’re definitely onto something with the 
rise of happiness research and positive psychology 
and this whole movement. On paper we should 
be pretty happy with what we’ve got, but why do 
we kind of default to this hedonic adaptation and 
the treadmill of keeping up with the Joneses and 
everything else? It’s a mystery. I think the three 
ingredients we kind of touched on are love or 
relationships, a feeling of closeness and belonging, 
and community in the work. Are we doing work 
that lights us up? Are we doing work that we care 
about? Then you might need a sense of progress. 
Am I working toward mastery? Am I doing some-
thing that I care about either personally or profes-
sionally? Do I have the sense that tomorrow’s going 
to be better than today? Without those ingredients, 
it’s really tough to wake up excited in the morning.
In terms of all the side hustles out there, is there any single promising opportuni-
ty that you see right now for people to create their own work, especially some-
body who’s a writer?
Writing is a fascinating one because it’s such a universally valuable skill that it’s hard 
to come by in a way. But side hustles for writers, a couple come to mind that are really 
Nick was a TEDx speaker in 2014 in Livermore, California, 
and presented on “The Entrepreneurial Generation.”
barefootWriter • Page 12 • October 2023
interview with a barefoot writer (continued…)
exciting: One would be a curated newsletter type of business model where we’ve seen 
some really high-profile newsletter businesses where they’re not necessarily creat-
ing original content, they’re just 
finding interesting stories and 
then summarizing or putting your 
own unique spin on them. One 
was Morning Brew, which sold 
for, I want to say $70 million or 
something.
The Hustle is another example. It 
was not your dad’s business news. 
It was like, “Hey, we’re going to 
build Wall Street Journal for the 
next generation and we’re going 
to put our own unique spin on it.” 
But what made it stand out was 
that the quality of the writing real-
ly was excellent. So you could kind 
of pivot that model to whatever 
niche or industry you’re interested 
in. Maybe it’s gardening, maybe 
it’s parenting, maybe it’s home of-
fice decor. There are lots of differ-
ent opportunities in that space. 
The other opportunity on the writing side that I think might be compelling is creating a 
done-for-you managed service to create Twitter [now known as X] threads or LinkedIn 
posts or for Instagram. We’ve seen some people build really significant audiences on 
these platforms starting essentially from nothing.
It’s kind of playing the viral lottery in a way where it’s like, I wrote a thread every day 
and nine of them over the course of a year accounted for 80% of my growth. It’s just 
putting in the reps but finding the right hook. There’s definitely a formula to it and po-
tentially AI assisted at this point. But I think helping creators take long-form content or 
even businesses take long-form content and turn it into compelling content that looks 
native on those platforms could really be an opportunity to start some sort of agency 
or service.
You nailed it there, because it’s really about putting in the reps. Then that first 
time you’re paid for something you created out of your own head really brings 
the confidence.
A little bit like alchemy, creating something out of nothing. I play the SEO game in a 
lot of the Side Hustle Nation writing where it’s like, to take something from blank page 
Nick enjoyed a full summer hiking season with his family, including visiting 
places like Coal Creek Falls, Mount Washington, Teneriffe Falls, Snow Lake, 
Garfield Ledges, and other sites within the state of Washington.
barefootWriter • Page 13 • October 2023
interview with a barefoot writer (continued…)
and have it post and stick on the first page of Google where it can earn traffic and rev-
enue and email sign-ups sometimes for years, it feels pretty magical.
Are there any other side hustles you’d recommend specifically to writers?
The side hustle where we’ve seen the biggest outsize results where you’re building 
cash flow on a monthly basis but you’re also building equity in a business is creating a 
website. It’s creating a helpful resource 
destination online that is monetized 
with advertising and with affiliate re-
lationships. A recent example is Shelly 
Marmor, who built travelMexicosolo.
com, and it’s all about travel tips to 
Mexico and targeting kind of what she 
called long tail keywords. Best hotels in 
Tulum with kids, with pets, for couples.
Maybe they’re not the most exciting 
things to crank out, but she got affiliate 
commissions from the hotels on the 
back end of those, or tour ideas, affili-
ate commissions from these different 
tour groups and stuff that was going 
on. When we spoke a couple months 
ago this summer, she was doing 50 
grand a month from this portfolio of 
different travel sites.
Now, a lot of this freedom and extra income doesn’t matter if you’re working 
yourself to the bone. You manage a huge company now with a lot going on 
behind the scenes. What’s your favorite timesaving technique for being super 
productive?
For me, it starts with a time audit. Being honest with where my 168 hours in a week 
is actually going, because oftentimes you’ll find this is stuff that doesn’t need to get 
done, doesn’t need to get done now, or doesn’t need to get done by me. There are 
opportunities to eliminate, automate, delegate inside of that time audit. Do this for 
a week or two and be super honest with yourself. That’s one of the most common 
excuses that I hear from Side Hustle Show listeners: “Yeah, it all sounds great, but I don’t 
have enough time.”
Well, we’re all dealt the same 24 hours in a day, and we vote on our priorities with how 
we spend our time. Because I still find myself guilty, I try to be more honest and say, 
“Well, I prioritize something else.” That’s the more honest way of phrasing that. What 
I try to do is itemize out my top three priorities for the next day the night before, so I 
know exactly what to work on and in what order, hopefully before diving into reactive 
Taking time off to have fun with family is one of the many perks Nick 
enjoys thanks to choosing an entrepreneurial lifestyle.
barefootWriter • Page 14 • October 2023
interview with a barefoot writer (continued…)
mode of email and social media. I want to move my own agenda forward before re-
sponding to somebody else’s, if that makes sense.
On the freelancer or copywriter side, what is the time spent on the searching for work, 
like the client outreach and the discovery calls versus the billable hours, time behind 
the keyboard writing? I think that would be an interesting breakdown, and you can’t 
necessarily neglect the marketing and sales side otherwise. Maybe you only spend half 
your time writing, so you need to adjust that upward to pay for all of this marketing and 
admin time.
Given your attention to where your time and energy are really going, I assume 
that does give you the freedom that you aspired to when you first made this leap. 
How do you make the most of that freedom and downtime? 
We’re coming off the end of summer break here, and I’m very grateful to have redis-
covered summer break as an adult, especially since we’ve got young kids in elementary 
school. Being able to take a bunch of time off over the summer with them to go hiking, 
biking, hit the lake, hit the pool in the neighborhood — that’s been super rewarding, 
and I’m very grateful to be able to do that. It’s going hiking with Dad, it’s going golfing 
with Dad. It’s the stuff that he really wasn’t able to do during his working years, and so I 
feel very grateful.
It’s weird: I don’t make money while I’m working so I can make money while I’m not 
working. It’s a weird paradigm shift to try to set up these little digital assets on the in-
ternet in most cases, and hopefully some of thosestick and can pay dividends for years, 
but it’s not necessarily billing any hours while I’m sitting at the desk. Super grateful to 
have that time.
You’ve come full circle and re-
claimed summer vacation. Now, I’ve 
heard you talk about the three Cs: 
creation, connection, and contribu-
tion. As writers, how can we put 
these into practice?
Well, you get the creation part down. 
That’s what you do all day every day. 
It’s like going from a blank page to a 
finished piece and feeling that satis-
faction of, Hey, I made something. This 
is going to help somebody sell more of 
their product or service. This is going to 
attract more visitors to their website. 
This is going to go viral on social media. 
That creation piece I think comes easy 
for anybody who is in a creative field. 
The connection part is that marketing 
Here’s Nick with his son at Poo Poo Point, a hiking area in King County, 
Washington, that includes a launch point for paragliders.
barefootWriter • Page 15 • October 2023
interview with a barefoot writer (continued…)
piece, which can sometimes be a little more difficult. How do I sell myself? How do I find 
myself inserted into a sales process or find somebody who’s looking for the skills that I have? 
Maybe that’s on a freelance marketplace or a job board, or maybe that’s through a 
series of recurring clients and word-of-mouth relationships.
Then the contribution piece is like, What good does it do? What’s the impact that work 
is going to have for the client’s business or for your own personal satisfaction? Ideally 
both. If you can make an impact and feel good about doing it, you’ve checked that box.
What’s the number one piece of advice you could offer someone who wants to 
create and also reap rewards in the form of both money and freedom?
You’ve got to position it as an experiment in your mind and put on that scientist hat. 
Give yourself 30, 60, 90 days, whatever time frame makes sense for you. Say, “Look, I’m 
going to give this a shot. I’m going to see what works. I’m going to see what doesn’t 
work. I’m going to see if I like doing it, see if it’s worthwhile, see if I’m getting traction 
on this.” Not even really letting yourself reevaluate until that 30-, 60-, 90-day window 
is up, because you have to give yourself a little bit of time, getting some reps, to see, 
“Okay, this is something that is worthwhile to do.”
Then I think positioning it as an 
experiment is super important be-
cause it gives you permission to fail. 
The scientist in the lab, the test tube 
blows up in her face, she says, “Okay, 
hypothesis disproved, on to the next 
thing,” versus “Oh, I’m an abject 
failure. This is never going to work.” 
I think it’s the same with all of these 
different projects that I started, 
including the ones that failed miser-
ably. It’s like, “Well, it was an experi-
ment. I gave it a shot. Didn’t happen 
to work that time, but we’ll take the 
lessons learned from that and apply 
that to the next thing.” Writers can 
do that too, especially with side 
hustles. ¢
Catching baseball games with his kids is a 
favorite summer activity of Nick’s.
barefootWriter • Page 16 • October 2023
featured essay
The Rat Race, 
Defined
By Nick Loper
The term “rat race” means different things to different people, but let’s see if I can 
paint a picture.
You might feel like you’re stuck in the rat race if you’re
 l commuting in traffic,
 l to a job you don’t love,
 l to barely get by.
There’s a certain circular rhythm to your days, weeks, or even years. You’re spinning 
your wheels but not getting anywhere. You perform tasks, go through the motions, 
and sometimes even get rewarded for your efforts… but you still feel trapped.
A friend put it this way: “We work jobs we don’t like, to buy stuff we don’t need, to impress 
people we don’t know.”
Is this what adulting is supposed to be like?
There’s got to be more to life, right?
The 3 Most Common Paths to Getting Out of the Rat Race
Now, part of escaping the rat race means having non-job income that exceeds your 
monthly expenses.
The three most common ways to generate that income are
1. traditional investments,
2. real estate, and
3. entrepreneurship.
These are in contrast to — and far more realistic than — other paths some people bank 
on, like
 l an unexpected inheritance,
 l a lonely Nigerian prince, and
 l winning the lottery.
barefootWriter • Page 17 • October 2023
featured essay (continued…)
Figure Out Your Spending
Living frugally — or at least spending with intention — is an important part of your rat 
race escape plan. The less you spend, the less income you’ll need to break free.
If you’ve never calculated how much you actually spend on a monthly basis, it’s worth 
taking a minute to figure it out.
Do you spend $3,000 a month? Do you spend $10,000 a month?
How much does your lifestyle cost?
This is the income you need to generate — this is your Rat Race Freedom Number.
So how do real people achieve it?
1. Save Your Way Out with Traditional Investments
The most commonly prescribed path to escape the 
rat race is through traditional investments, like
 l stocks,
 l bonds, and
 lmutual funds/ETFs.
How Traditional Investing Works to Escape the 
Rat Race
This is how “retirement” has worked for generations: 
Amass a big enough nest egg during your working 
years, and then slowly draw down on those savings 
after you stop working.
At that point, you’re literally getting paid to do nothing… but the problem is, you prob-
ably don’t want to wait decades until you’ve saved enough!
The FIRE (financial independence/retire early) movement has an alternative for you, 
and argues that retirement isn’t an age, but rather a number. According to the oft-
cited Trinity study, once you accumulate 25x your annual expenses, you’re free.
Spend $40,000 a year? You could theoretically leave the rat race behind with $1 mil-
lion in traditional investments, and live off dividends and share price appreciation for 
decades.
Spend $100,000 a year? You’d need $2.5 million.
Advantages of Traditional Investing
These so-called “paper assets” are accessible to just about everyone.
Stocks, bonds, and mutual funds and ETFs are also highly liquid, meaning you can buy 
and sell them quickly.
And over the long run, they’ve historically performed very well. Projecting 7–9% an-
nualized returns would be realistic.
barefootWriter • Page 18 • October 2023
https://en.wikipedia.org/wiki/Trinity_study
https://en.wikipedia.org/wiki/Trinity_study
featured essay (continued…)
Disadvantages of Traditional Investing
The big drawback is that trying to get out of the rat race with traditional investing 
takes either a lot of time or a lot of money. 
Despite enthusiasm from the FIRE community, the truth is that unless you have a wide 
margin in your personal finances — the gap between what you earn and what you 
spend — there’s no real way to shortcut building up that nest egg.
Plus, should unexpected expenses pop up during retirement, your withdrawal rates 
and assumptions can go out the window.
Which brings us to option two…
2. Beat the Rat Race with Real Estate
The next common rat race escape path is real estate, 
and for the sake of this post, I’ll focus on rental prop-
erty investing.
How Real Estate Works to Escape the Rat Race
Real estate is appealing for its easy-to-understand 
business model:
Buy a house, rent it out, and pocket the difference 
between that rent and your monthly expenses.
Lather, rinse, and repeat until you’ve got enough 
monthly cash flow to quit your job.
Invest with that monthly cash flow in mind, and use it to slowly start chipping away at 
your own living expenses.
Advantages of Real Estate
Rental property investing can accelerate your climb to financial independence in sev-
eral important ways.
First, you can take advantage of leverage — borrowing money. In contrast to tradi-
tional stock market investing described above, where $20,000 buys you $20,000 worth 
of stocks,that same $20,000 could be used as a down payment to buy $100,000 or 
more worth of real estate.
Then you can pay down that loan balance from the rental income you receive over the 
next 30 years.
The next big advantage of real estate is appreciation. As you know, houses tend to 
cost more today than they did a generation ago.
By owning those properties, you can capture this appreciation when you sell — or bor-
row against the equity in your houses to fund future acquisitions.
Third, being a landlord comes with several tax benefits, including the ability to write 
off your mortgage interest and even take depreciation on the buildings you own.
barefootWriter • Page 19 • October 2023
https://www.fool.com/millionacres/taxes/real-estate-tax-deductions/top-5-tax-advantages-real-estate-investing/
featured essay (continued…)
And finally, real estate can be a very passive income stream once you have your tenants 
and other relevant team members in place. There’s an upfront time investment, but no 
trading hours for dollars down the road.
Disadvantages of Real Estate
Home prices don’t fluctuate as wildly as the stock market, but investing in physical as-
sets takes more legwork and also means your cash isn’t as liquid. 
(You can’t exactly just press a button on your phone and sell a house when you need 
cash.)
And although there are some creative ways to buy houses for no money down, real 
estate is usually a “takes money to make money” option.
As a landlord, you’ll also face vacancies, repairs and maintenance, unexpected ex-
penses, and tenant issues. On top of that, your local real estate market might not be a 
great place to invest, so you’ll be dealing with all this remotely or through a third-party 
property management service.
Still, there’s another rat race escape path you need to know about…
3. Escape the Rat Race with Entrepreneurship
The third way to get out of the rat race is to build your own business.
If you look at the Forbes 400 list of the richest peo-
ple in America, one thing should stand out: Most 
built their wealth through entrepreneurship.
And even if you have no aspirations to build the 
next Amazon or Facebook (I certainly don’t!), build-
ing a business is a realistic way to break out of the 
9–5 grind.
It’s how I was able to walk away from corporate 
America years before starting Side Hustle Nation. 
Entrepreneurship has helped hundreds (maybe 
even thousands now!) of friends, Side Hustle Nation 
readers, and Side Hustle Show listeners do the same!
How Entrepreneurship Works to Escape the Rat Race
We tend to overcomplicate entrepreneurship, but I’ll try to break it down here.
A business is simply a system that solves a problem in exchange for money. It’s a 
problem-solving machine.
That means to come up with a business idea, you really need to come up with a prob-
lem. Think of
 l what frustrates you,
 l the headaches or challenges you’ve overcome, and
 l what other people complain about.
barefootWriter • Page 20 • October 2023
featured essay (continued…)
It’s important to 
start small, minimize 
your expenses, and 
grow at a pace you’re 
comfortable with.
On the other side of those problems, there might be a business idea.
The solution usually takes one of three forms:
1. A service that makes that problem go away. Dirty house? You can hire a cleaning 
service.
2. A product that makes that problem go away. Dirty house? You can buy cleaning 
products.
3. “Content” that makes that problem go away. Dirty house? You can watch YouTube 
videos about how to organize and optimize your space.
And when the money from your solution starts to exceed your living expenses, it’s au 
revoir, rat race :)
Advantages of Entrepreneurship
Building a business is unique in that your primary invest-
ment is “sweat equity.” These days, you can get an enter-
prise off the ground for a very low startup cost.
On top of that, starting a business is a way to work on 
something you care about. Bringing an idea into the 
world is exciting and rewarding in a way that collecting 
stock dividend payments just isn’t.
And in contrast to the stock market or real estate market, 
you have considerably more control over the success 
and failure of a business you own (and the speed at which 
that can happen).
Plus, if you intentionally build something with scale, you’ll find entrepreneurship to be 
time leveraged. By that I mean that your earning power — or effective hourly rate — 
improves as your business grows.
Disadvantages of Entrepreneurship
With job security in question and the shift toward a freelance workforce, it’s hard for 
me to see the downsides in learning an entrepreneurial skill set.
Still, the fact remains that 50% of small businesses fail in their first five years. For that 
reason, it’s important to start small, minimize your expenses, and grow at a pace you’re 
comfortable with.
Building a business can be labor intensive, and many entrepreneurs find themselves in 
a trap of working in the business rather than on it. They feel like they’ve built themselves 
a job… only one with a really demanding boss that’s even harder to walk away from.
Who Is Entrepreneurship Best For?
I believe entrepreneurship is the most realistic rat race escape path for most people, 
but especially those who
 l don’t have the “golden handcuffs” of a great-paying job,
barefootWriter • Page 21 • October 2023
featured essay (continued…)
 l aren’t afraid of failure, and
 l are a little impatient.
Entrepreneurship appealed to me because I couldn’t fathom the reality of working a 
corporate job for the next 30 years. There had to be a better way!
And there was.
Why Do You Want to Escape the Rat Race?
What’s beyond the walls of the rat maze for you?
While “escape” can be a powerful motivator, I think it’s helpful to know what you’re 
escaping to. If you weren’t tied to your job for income, what would you do instead?
Motivations include
 l a location-independent lifestyle — 
not being restricted to one part of 
the world,
 l early retirement,
 l less stress,
 l working from home, and
 l leaving the big city for a slower 
pace of life.
For me, my driving force was to gain 
freedom over how I spent my days.
When I worked a corporate job, it just 
rubbed me the wrong way that I had 
to ask someone else (my boss) if I could 
take vacation on certain days.
I also wanted to see the direct impact of my work on my bottom line — something I 
didn’t get at the day job. Whether I did great or did poorly, my paycheck remained the 
same.
Not super motivating.
With my side hustle, on the other hand, the harder I worked, the more I made.
For me, getting out of the rat race wasn’t about never working again. I just wanted 
more flexibility, control, and earning power from my work. ¢
Editor’s Note: Reprinted from this site with permission from the author; lightly edited 
for clarity and style.
barefootWriter • Page 22 • October 2023
https://www.sidehustlenation.com/rat-race/
barefoot writing opportunity
The Best Writing-Based Side 
Hustles for Extra Money in 
Your Pocket
By Mindy McHorse
What would you do with an extra $810 every single month? It’s money in your 
pocket even after you’ve paid those bills, stocked the refrigerator, and finally had 
the repairman fix your heater before the autumn chill really settles in.
Turns out, $810 is the average amount earned each month by folks who hustle… well, 
actually… who side hustle!
A side hustle is simply a way to earn money outside of your traditional job. Think of gigs 
like dog walking, Uber driving, or setting up an Etsy business to sell those crafts you 
enjoy making in your spare time.
In short, a side hustle isn’t usually a ticket to wild riches. Instead, it’s a way to take control 
of your own financial health and well-being. A way to earn some extra cash that gets 
you through tight times or sets you up for those extra fun things you’d like to do or buy.
These days, more and more people are turning to sidehustles to earn some extra 
income. A 2023 Bankrate survey of 2,505 adults found that 53% of Gen Zers, half of all 
millennials, and 40% of Gen Xers have side hustles.
And guess what? A side hustle isn’t limited to dog walking and Etsy crafts… 
In fact, content and copywriting both present some perfect opportunities to build a 
writing side hustle that helps you earn that $810 per month… and then leave that num-
ber in the dust!
barefootWriter • Page 23 • October 2023
barefoot writing opportunity (continued…)
A Writer Who ‘Side Hustled’ His Way to Freedom
Want an example? Just look at writer Steve Maurer. He’s a beloved member of our AWAI 
community, and it’s likely you’ve seen him featured in these pages from time to time. 
What you might not know is that Steve worked 
for years… well, actually decades… as the “go-to” 
mechanic at a food processing plant in his home of 
Fayetteville, Arkansas. As Steve said, “I was the guy 
everyone called at 2 a.m. when stuff didn’t run.”
Back in 2009, the plant cut his hours and Steve de-
cided to start his own writing side hustle to bring 
in some extra income. He kept his full-time job, but 
used his spare time in the early mornings, eve-
nings, or weekends to write articles about a topic 
he knew inside and out… industrial mechanics!
Once he sharpened his writing skills using the programs in AWAI, Steve was able to 
grow his little writing side hustle enough to boost his overall annual income by 50%. 
Then, he started earning around $200 per hour for his writing (still done “on the side”!).
By the time he finally quit his day job, Steve’s writing side hustle was earning him more 
money each year than his full-time employment! Now, that’s what we call some serious 
hustle!
So, as you can see, a writing side hustle doesn’t need to have limits. Sure, you can 
achieve that average of $810 extra cash each month. Or, you can use that spare-time 
writing habit to grow and grow your service until your side hustle becomes your main 
source of income.
Ready to get started? Here are our top seven writing side hustles you can start this 
season!
#1: Write About a Topic You Love
What better place to start than with the side hustle Steve used to quit his day job… 
blog writing!
These days, most companies post regular articles on their websites to help readers 
learn about topics, solve problems, find inspiration, or make important buying deci-
sions. That’s why there’s a constant need for writers who can craft interesting and fresh 
new content for these blogs. Each article helps a company raise awareness for their 
brand and build trust with their audiences. 
And, this is big… these blog articles are about a huge range of topics. It doesn’t matter 
if you love outdoor camping, gardening, dentistry, teaching, football, heavy metal, pot-
tery, or industrial mechanics. Chances are you can find a company online that needs a 
blog writer to help them create that content!
As a blog writer, you can connect with companies who need regular content written 
barefootWriter • Page 24 • October 2023
barefoot writing opportunity (continued…)
about their specific industry or topic. These articles are short and usually fall 
between 300 and 1,200 words. And you’ll typically earn between $200 and 
$500 for each blog post.
Best of all, blogs are an ongoing source of work. That’s because companies 
understand the power of posting regular content each month, each week, 
or sometimes each day! Once they find a blog writer who can nail the voice 
of the company, they’ll happily ask that writer to write more and more blog 
posts each month. Note that you can learn more about this type of side 
hustle through How to Write Blogs for Yourself and Clients: A Step-by-Step 
Guide to Blogging Success.
Speaking of ongoing work…
#2: Get Paid to Write Notes to ‘Friends’
This next side hustle is one you’re probably already doing every single day.
Yup… writing emails!
Every time you sit down at your computer to write a friendly email to a friend, you’re 
using skills nearly identical to those that some writers use to earn hundreds or thou-
sands every month.
Why the big payouts? Well, in 2020, 306 billion emails were sent and received daily. And 
many of those emails were sent by companies who want to keep in touch with their 
customers and share news about exciting offers and promotions.
Turns out, these emails do a really great job at making sales! The Direct Marketing 
Association found that for every $1 spent on email, businesses earn an incredible $38 
back from their customers!
Online companies know that email works, and they love having writers who can help 
them write fun, short, and simple messages that match their brand style and voice.
A typical email is only a few hundred words and will often pay between $200 and $400. 
Or, email writers can write a whole sequence of emails for $3,500. This is just a set of 
three to 10 emails all about the same topic sent out in sequential order to the same 
audience.
Other companies ask for regular email newsletters to inform their readers of impor-
tant news and company updates. These newsletters might go out every week or every 
month.
Email writing is fun, easy — and, once you get started with a handful of clients — quite 
lucrative! It’s a great side hustle for writers who want a consistent, ongoing source of 
extra cash month to month. The go-to training for this side hustle is here: How to Write 
High Impact Emails.
Now let’s move on to the next side hustle… This one is great for people with an eye for 
detail!
barefootWriter • Page 25 • October 2023
http://www.awai.com/blg/barefootwriter
http://www.awai.com/blg/barefootwriter
https://www.awai.com/ema/barefoot/
https://www.awai.com/ema/barefoot/
barefoot writing opportunity (continued…)
#3: Get Paid to Look for Typos
Have you ever been asked to look for typos?
Maybe a friend needed you to check over a text before they hit “send.” Maybe a co-
worker asked you to review an email before it was broadcast to the entire company. Or, 
maybe your teen asked you to review their homework before they submitted it to their 
teacher.
That’s when you use your critical eye and look over the writing carefully to check for 
factual errors, typos, misspellings, and parts that don’t make sense.
Guess what? You just did copyediting! It’s our next side hustle opportunity — and it’s 
one that perfectly complements your work as a writer.
All sorts of companies need copyeditors to review their writing before it’s published 
online. That’s because these companies know they’ll see better results and stronger 
sales when their copy is free from errors.
People who use copyediting as a side hustle can choose how they’d like to get paid. 
Some prefer a retainer relationship with their clients. This is where they promise to save 
time for that client’s work every month for a set amount of money. Others work on 
projects one at a time or even use an hourly rate.
When all is said and done, copyeditors can earn a median annual income of $59,000, 
according to the U.S. Bureau of Labor and Statistics. And the top 10% of copyeditors 
make more than $114,000 per year. If this sounds like something that would suit you 
well, check out How to Use Copyediting for Career Advancement and Side Profit.
Not bad when you consider how easy this skill is to learn!
#4: Review Websites for Companies
If editing individual pieces of writing feels easy and exciting, then you’ll love this next 
side hustle. That’s because you can lend your critical eye to an entire website!
Have you ever seen a website that needed some work?
Maybe the content wasn’t organized well or it was 
hard to follow. Or maybe the site was missing entire 
sections the visitor needed to understand the com-
pany’s message, culture, and brand.
As a website auditor, you can help companies 
analyze their sites and make improvements to 
the content and structure so it better serves their 
customers.
This work is actually prettyeasy. In fact, you’ll use a 
standard checklist to scan through a site while mak-
ing notes of elements that are missing or those that 
barefootWriter • Page 26 • October 2023
https://www.awai.com/edt/barefoot/
barefoot writing opportunity (continued…)
could be improved. Then, you’ll organize your results in an easy-to-understand format 
and present it to your grateful client.
This side hustle service easily pays you $1,000 to $2,500 per website for just a few short 
hours of work. And best of all? If the company decides to fix any of the content on their 
site, they’ll be looking for a writer who knows their content inside and out. 
Who will they call? Yes, you!
As a website auditor, you can actually get paid twice for a single client. You can com-
plete their site audit, share suggestions for improvement… and then charge a whole 
new fee to go back into the site and rewrite weak content. 
It’s a side hustle with the potential to grow into a very lucrative business. You can learn 
how to get started with Site Audits Made Simple. And finally, here’s one last side 
hustle to get you going this fall…
#5: Post on Facebook and Instagram
It’s another skill you may already be using on a daily basis. Be-
lieve it or not, you can actually earn money by helping compa-
nies create fun and engaging social media posts for their X (for-
merly known as Twitter), Facebook, and Instagram accounts.
These posts are a lot of fun to write and often very short — 
fewer than 100 words, in fact. As a social media writer, you can 
write batches of posts for a single client all at once and deliver 
them each and every month.
Many writers will spend just one to two hours per day, five days 
a week writing this interesting and engaging content and post-
ing it for their clients. They earn around $1,000 to $2,000 per 
month… just for one client!
As you can see, that average of $810 per month we mentioned earlier is definitely not a 
limit you need to stick to. The quickest way to get started? Check out AWAI’s program 
on How to Make Money as a Social Media Marketing Expert.
Learn the ‘Method’ for Getting Started
Regardless of which side hustle you choose, one thing remains true… 
You’ll need a basic foundation in strong writing to help you craft those messages, 
tackle those edits, and refine those posts. That’s why you’ll want to study the tried-and-
true fundamentals of copywriting and persuasion.
Here at Barefoot Writer, we’ve been teaching these skills for more than two decades. 
And we’ve decided to combine all of our core writing principles into one powerful 
resource — The AWAI Method™ for Becoming a Skilled, In-Demand Copywriter. This 
is the best place to gain the skills and knowledge you’ll need to put your writing side 
hustle into action. To wrap this up, I just have one quick question…
Are you ready to hustle? ¢
barefootWriter • Page 27 • October 2023
https://www.awai.com/sas/barefoot/
http://www.awaionline.com/sme/barefoot
https://www.awai.com/amc/barefoot/
glicken
5 Tips for Enjoying Fun and 
Profitable ‘Workations’ All 
Over the World
By Jason Gaspero
When I first got into freelance copywriting over two decades ago, I became ob-
sessed with the idea of making great money from anywhere in the world.
Thanks to AWAI’s flagship copywriting course, I landed my first major freelance copy-
writing client in the summer of 2005, moved to Paris, and launched my copywriting 
career.
I also began taking some of the most amazing “workations” imaginable, which I’ll share 
with you in just a moment. But first…
What’s a workation?
A workation is when you…
1. travel to a destination different from where you regularly work…
2. stay there for a few days, a few weeks, or perhaps even a few months…
3. spend part of your day (preferably the mornings) working remotely and getting 
things done, and…
4. take the rest of the day to enjoy the recreational activities, scenic beauty, great 
food, and friendly people your chosen location has to offer.
Some of my most cherished lifetime memories came from workations. In my first year 
of copywriting alone, my workations included…
 l running with the bulls at the Fiesta de San Fermin in Pamplona, Spain… 
 l going bar-hopping in Lagos, Portugal… 
 l dancing the night away while watching legendary DJ Carl Cox spin the decks at 
Space in Ibiza, Spain… 
barefootWriter • Page 28 • October 2023
glicken (continued…)
 l drinking huge steins of beer with millions of revelers at Oktoberfest in Munich, 
Germany… 
 l wearing a kilt in subzero temperatures while celebrating Hogmanay in Edinburgh, 
Scotland… 
 l and many more epic international adventures.
And I continue to enjoy workations to this very day.
Why Workations are The Best of all Worlds for Freelancers 
Not only do workations allow you to continue earning consistent income no matter 
where in the world you want to be…
But you can also enjoy the same kind of epic, memory-filled adventures all over the 
world (like I did and still do) that most people get to enjoy only for two short weeks per 
year on holiday… if they’re lucky.
One caveat, though, about workations.
I’ve learned through many, many years of hard-won trial and error that there are a few 
key things you must do to ensure your workations go smoothly and effectively.
Otherwise, you may put your productivity, your creativity, or perhaps even your career 
at risk.
Here are five of my best tips for enjoying fun-filled, highly profitable, and 100% 
guilt-free workations anywhere in the world:
1. Choose the right destination. I suggest using booking sites like Booking.com 
and joining Facebook expat and real estate rental groups to check out the places 
that interest you. Post any 
questions you may have. And 
make sure it’s a quiet place to 
work from (with air-condition-
ing in hotter locales). TIP: Be 
mindful of the time zone dif-
ference for conference calls. 
2. Secure proper workplace 
amenities. An ergonomic 
chair, a dedicated work desk, 
and an external monitor all 
really help. Check the photos 
online (ask if none are avail-
able) to see if the places that 
interest you offer these ame-
nities. Many do these days. 
TIP: Bring an HDMI cable. 
You may be able to plug your 
Here’s the work station Jason wrote this article from in a Bangkok hotel 
— complete with the HDMI cable he brought with him to connect to the 
external monitor in the room, his countdown timer app with 51 minutes left 
to go out of two hours (see Tip 5!), and Jason grinning at the mirror.
barefootWriter • Page 29 • October 2023
glicken (continued…)
laptop into an external monitor (if they have one), which makes a huge difference. 
I’m using one in Bangkok right now as I write this!
3. Secure reliable internet access. Most places worldwide offer decent enough 
Wi-Fi these days, but not always. You can ask the landlord or property owner to 
send a screenshot of a “speed test” to check the Wi-Fi speed. TIP: Consider renting 
or buying a pocket Wi-Fi device and get a high-speed data SIM package for your 
destination. You can fall back on that if the Wi-Fi gets sketchy or the power goes 
out (see next tip).
4. Secure backup power. In many tropical destinations, the power often goes out 
during thunderstorms. However, if you have a large power bank or an uninterrupt-
ible power supply (UPS) at your place of work, you can continue working without 
stressing about your gadgets running out of juice. TIP: Find out which places near 
you (often the bigger hotels and resorts) have generators if you’re really in a pinch 
and need to plug in.
5. MOST IMPORTANT! Block 
out two uninterruptible 
hours in the morning to 
GET THINGS DONE! I can’t 
overstress the importance of 
this. It’s the only reason I’ve 
been able to enjoy all of my 
crazy workations over the 
years and grow my copywrit-
ing career at the same time. 
Here’s what I suggest you do, 
first thing in the morning, be-
fore “life gets in the way.” Let 
your friends and family knowyou won’t be available for 
two hours, no matter what. 
Lock your door. Put all your 
gadgets on airplane mode. 
Set your timer for two hours. 
Then, start your timer and 
bang out those two hours as 
if your life depends on it. 
Do this and you can get massive amounts of work done, provided you’re super fo-
cused. And once you’re done with your two uninterrupted hours of work, you’ll have 
the rest of the day to enjoy yourself guilt-free wherever in the world you choose to be… 
living the dream! ¢
This is Jason at a restaurant in Thong Nai Pan on the island of 
Koh Phangan, where he lives. He comes here in the afternoon 
every once in a while to relax, have a coffee, catch up on emails, 
do a bit of reading, and of course enjoy the view!
barefootWriter • Page 30 • October 2023
mobile freelancer
Living the Barefoot Writer’s 
Life in the Tropics
By Jen Phillips April
I step onto my balcony in the palm trees, coffee in hand, and greet the world. This 
routine is how I start most days in Playa del Carmen, Mexico. Sometimes, I wander the 
three blocks to the Caribbean Sea, and other mornings, I do a short yoga sequence on 
my balcony. 
By midmorning, I’m writing blog articles, emails, and other client work on my laptop.
One of my big reasons for starting my freelance writing business a decade ago was the 
portability factor. It may sound cliché, but I had envisioned working from “wherever” 
since my early 20s when I first read A Moveable Feast. Hemingway had to lug a giant 
typewriter and sheaves of paper around. Yet, he still received checks for his journalism 
work for U.S.-based clients. 
A laptop, Wi-Fi, and cloud storage make writing for clients much easier. 
Now I can live where I want and take extended trips because my office fits in my 
backpack. This summer, I spent two weeks in South Carolina with family. Then, my 
boyfriend and I spent six weeks on Mexico’s west coast, keeping a pair of cats company 
while their people were in the United States. 
The Great Move South
We had many reasons for leaving the cold, gray Philadelphia suburbs in 2017. Neither of 
us had any strong ties there. We were both self-employed and had already worked with 
clients around the world. We wanted warmer weather and affordable seaside living.
When my partner’s youngest daughter announced she was going to college three 
states away on a diving scholarship, it was time to put Operation “Move Somewhere 
Warmer” into action.
barefootWriter • Page 31 • October 2023
mobile freelancer (continued…)
Our criteria? Infrastructure, walkable, international commu-
nity, affordable, and easy access to the States. We looked 
at maps and YouTube videos. We visited my home state of 
South Carolina, but ultimately, Playa del Carmen, Mexico, 
ticked all the boxes. 
In the months leading up to our move, we sold or donated 
90% of our possessions and packed what was left in six suit-
cases. We nicknamed our cat Sombrero Kitty, and in Octo-
ber 2017, we flew to Playa del Carmen to start our new lives. 
A Walkable Paradise
Six years later, we’re still here. It’s a fabulous perk to pop 
down to the Caribbean Sea for a quick dip on a Wednesday 
afternoon. There’s beach yoga nearly every day, and even if 
it happens too early for my participation, I like knowing it’s 
there.
Because we live in the middle of the city, we can walk everywhere and don’t need a car. 
A supermarket is two blocks away and there are 300 restaurants within half a mile (we 
Googled it). We have friends from more than a dozen countries and an active social life.
A recent weekend included a rooftop pool party celebrating a friend’s anniversary. The 
night before, we enjoyed chiles en nogada, a traditional dish for Mexico’s Indepen-
dence Day, at a local restaurant. It consists of a poblano pepper filled with minced meat 
and dates or raisins, covered with a walnut cream sauce, and sprinkled with pomegran-
ate seeds. The colors represent the red, green, and white of the Mexican flag. 
There are as many variations on this dish as there are on Southern barbecue, and some 
people make a point of tasting as many as possible around town.
After dinner, we headed to the Plaza for Independence Day celebrations, where we en-
joyed an elaborate drone show before a famous Mexican band performed on the stage.
The Adventuring Hasn’t Stopped
Sombrero Kitty passed away in 2021 after spending three years enjoying favorite 
“building cat” status. He’d lie in the garden, luxuriating in the sun, and go door to door 
like a trick-or-treater — neighbors would tell us they had fed him a bit of shrimp. 
Now we pet-sit occasionally for friends and acquaintances. We get a pet “fix” and the 
chance to travel elsewhere and see what it’s like living there. Whether it’s across the 
country or three blocks away, it offers a fresh perspective, and we love exploring the 
nooks and crannies of our adopted country.
Workwise, I have a longtime niche writing for pet health and e-commerce companies. I 
also write emails, case studies, and blog content for B2B technology companies. While 
the laptop lifestyle looks different for everyone, my writer’s life in Playa del Carmen 
gives me the total flexibility I crave. ¢
Sombrero Kitty moved from 
Philadelphia to soak up more sun 
in Playa del Carmen with Jen.
barefootWriter • Page 32 • October 2023
become a better writer
8 Simple Steps to Crafting 
the Perfect Sales Letter
By Craig Grossman
Sales are the lifeblood of most businesses. Without them, an organization will die a
slow death.
That’s why you’ll be invaluable to your client’s organization if you can write a sales let-
ter (or even a sales email) that gets results.
Your 8-Step Sales Letter Formula with Examples
Note: Inside each section below are excerpts from a sales letter by the fictional business 
Advantage Warehouse Products for their DualMode Automated Forklifts. 
1. Start with the problem: A good sales letter begins with the primary issue your cus-
tomers are facing. Make sure this is a problem your client’s product will solve.
Dear Warehouse Operations Manager,
Have you noticed? Warehouse expenses are shooting up every year. One significant cost 
is having forklifts and their drivers available to move products around. If you have six 
forklift drivers, your payroll costs alone could be over $200,000 per year!
2. Identify the emotional or philosophical struggle: This is how the problem makes
the customer feel. You could also complete this sentence: “You shouldn’t have to deal
with _____.”
Seeing your hard-earned income pay for these wages gets frustrating! Maybe you’ve 
thought, Since they’re inventing automated cars, why not create automated forklifts, too?
barefootWriter • Page 33 • October 2023
become a better writer (continued…)
3. Explain your offer: Talk about how your product solves your customer’s issues us-
ing benefit-focused language (rather than just features).
Well, somebody has! Meet Advantage Warehouse Products’ new DualMode Automated 
Forklifts. These forklifts can be programmed to move products wherever needed — with-
out a driver! Or, operators can switch to driver mode for complex tasks.
You can now get more work done with fewer drivers. And with fewer accidents, too.
4. Insert a brief testimonial: Show how your product has solved this same problem 
for someone else, with a real-life example.
Joe Shogan, a Summit Warehousing manager in Huntsville, Alabama, told us, “We used 
to need 10 forklift drivers to move products from containers to storage. But since we’ve 
been using the DualMode Automated Forklifts from Advantage, we’ve reduced our 
needs to five drivers and retrained the rest for higher-value jobs.”
5. Add a call to action: Ask your client’s customer to 
buy your product clearly and directly. You can link your 
CTA to an order page. It can include the steps they need 
to take to simplify the buying process for a complex 
product or service.
Would you like to learn more about how easy it is