7 “Seasoned” Remote Workers Share Their Working Wisdom

7 “Seasoned” Remote Workers Share Their Working Wisdom

When I first started this blog, I received a lot of so-called ‘work at home advice’. Seemed like everyone had something to say.

In the beginning, I was receptive to this advice.  I was constantly on the lookout for fresh work at home job leads, ones that I thought I was good enough for.  It was an exhaustive search. It seemed the jobs weren’t around when I wanted them and when I did come across some, so did everyone else. So I latched onto all the advice I heard concerning remote jobs.

And I made a lot of mistakes.  I even had times when I wasn’t making any money.

But I learned from my mistakes.  I also learned from other people – successful people – who’ve been working from home longer than me.  Like my friend Stacey, who works 20 hours a week as a freelance photographer.  She told me to” just go for it. It’ll suck at first, but just go for it.  What have you got to lose?”.

Guess what ?  She was right. It DID suck.  But I was so glad to have her in my corner.

So one day I set out to interview a few seasoned work-at-homers, those who have been at it for more than 4 years, to see how they became successful with the whole “remote work lifestyle”.  Each one of them has their own story but the most interesting thing about each one is how they conquered this lifestyle.

Today, I’m sharing their stories. Great insight from 7 remote workers who have been able to raise a family, get through life, and work a remote job.

I hope they’re as valuable to you as they have been for me.


Julie works remotely

Julie “Start with what you know”

6 years working remotely

Job: Customer Concierge at Hilton

Julie used to work as a receptionist at the local Comfort Inn. She saw people every day, answering questions, answering phones and doing check-ins/check-outs. She was always busy. She started this job right after graduating High School, with no other experience under her belt. Her job was all about customer service, which she became very good at.

She continued working at Comfort Inn while her boys were little, with a good portion of her paycheck going to babysitters. When her youngest, Kenny, was 11, she was laid off and forced to find something else.

After about 8 months of trying just about anything legal to make money, Julie got a work at home job with Hilton, in their Hhonors division. The skills she picked up at Comfort Inn seemed to be just what they wanted in an employee. Julie works around 30 hours a week, makes just over $15.00 an hour, and the job includes a few benefits. The best part of her day: she gets to work at home.

Her Advice To Remote Workers:

I wish I started with what I knew. When I first got laid off from Comfort Inn, I applied to just about any job I thought I could do. Big waste of time.  I wound up bouncing from one so-called home job to another. Then one day I realized I really liked what I did at Comfort Inn so what was the point of a career change? Hilton has been pretty flexible in the schedule I wanted. At first it was kinda hard, when the kids were younger. I had to have a dedicated office and all the right equipment but that was the easy part. Keeping the kids quiet while on the phone was hard. I bought a good set of noise-canceling head phones and a huge supply of art supplies. I sometimes leaned on my friend, who also had a son, to take the kids for an hour or so. All in all, things worked out great.


Sammi works from home

Sammi “Get to know them…inside and out…”

5 Years Working Remotely

Job: Customer Service Specialist at Buffer

Sammi joined Buffer as a Customer Service Specialist a little over a year ago. She had worked a few work at home side gigs over the years, so she knew what it was like to be a working nomad, but nothing stuck. She knew she wanted to do something that didn’t require a lot of education and wasn’t all phone based. Her introverted personality made sure of that.

When she got her job with Buffer she was filled with excitement – then anxiety. How was she going to make this job work for her ? She had absolutely NO previous experience doing customer service except for her stint as a waitress at Denny’s. And she had no one to turn to for work at home advice.

Her Advice To Remote Workers:

When Buffer hired me I almost peed my pants. I was that excited. I had been looking for a work at home job for a while and was just about to give up. We needed the second income and I was just about to start looking for work at the mall. The thought of that really sucked.

When I first found the job at Buffer, I learned about the company THOROUGHLY. I mean, I devoured EVERYTHING ! I got to know them inside and out. Their blog, their Twitter and Facebook profiles. All of it. I wanted to know this company. Also, the job description was full of information that I used to my benefit. I learned what tools they use, what type of person they were looking for, and which qualities they want in an employee. I made sure I had a good resume for a remote job and that it matched what they were looking for. It paid off.


Kris, a remote worker

Kris “Never stop looking for that perfect job”

5 and a Half Years Working Remotely

Job: Social Media Strategist with HotJar

Kris has been a social media junkie since the days of MySpace. She also has an analytical mind so sorting through details comes naturally to her. When she found herself wanting a career change (she was a bookkeeper for a home builder in Michigan) she decided to give a try at freelancing her social media skills. She got a few clients, earned a few bucks, and was able to pay the bills. Most importantly, she could stay at home with her daughter.

But trying to find clients was not Kris’s thing. And trying to use Upwork (elance when Kris used it) wasn’t the best option because it seemed only the lowest bidders got the gigs. So it was time for Kris to move on.

After finding some jobs, applying for a few, and being rejected by most, Kris resorted to trying some of the side-gigs to make extra money.  After all, the bills kept coming in. Kris finally landed a position with HotJar. It literally took her 11 months of non-stop looking.  This job came just in time for her.

Her Advice To Remote Workers:

Never stop looking for the perfect job. Don’t become complacent because then you’ll never find the job that makes you really happy. I knew I didn’t want a job that didn’t suit my expertise but I needed to start making money. I could do one thing, and one thing well: social media. And because this is a relatively new kind of job, they don’t come up very often. So, to make ends meet…kind of…I continued freelancing. I also did some of those ‘get-paid-to’ sites just to be able to buy groceries. So when this job came up, it had my name all over it.


Quinn works at home

Quinn “Don’t let discouragement get the best of you”

7 Years Working Remotely

Job: Captioning with Rev

Quinn started her working life waitressing at a few different diners. The pay was minimum wage and the tips were ho-hum. But for a single young woman with virtually no debt, waitressing was a great way to make a living.

When she got pregnant, Quinn and her husband knew she had to go back to work as soon as possible.  But she would soon face the reality that many moms face: wanting to be there for the kids. She wanted to work at home but she had no idea what she wanted to do, especially with the few skills she had. So she searched everywhere for something that might interest her. And, after about 2 years of looking at hundreds of jobs, she started working for Rev, first as a transcriptionist then later doing online captioning. She has been doing this job for 4 years and loves the flexibility she has.

Her Advice For Remote Workers:

There are so many jobs out there, on the internet, but I have found most of them to be the same old stuff. Some things sounded interesting at first glance, but when I applied for the job I either never heard from them or was told the job was filled. And in a lot of cases, the pay was crap. I had a baby to think of, for pete’s sake.

It’s hard not to get discouraged but you can’t quit looking. Because I didn’t have any skills that transferred to an online job, my options were limited. And being a mom who wanted to spend time with my baby made finding the right job super hard. I wasn’t interested in going to school because I didn’t want (what I call) a “formal career”. I just wanted a job that kept me busy and paid some bills. I got discouraged early in my job search, thinking an online job for me just wasn’t out there. I mean, I looked at just about EVERY remote job. Transcription was on my radar, and I knew this was something that beginners could do, but I didn’t think it was for me. But after a while of getting nowhere in my search, I decided to give it a go. I got a job with Rev pretty quickly after the application/test process and after a year of transcription under my belt I moved into a better paying captioning position.  I’m so glad I did it !


Keving works remotely

Kevin “Think of different ways to do what interests you”

4.5 Years Working Remotely

Job: Content Marketing Analyst with Animalz

Kevin worked in marketing since graduating college. It was a good job but it was stressful and he wanted out. Kevin wanted to do something that let him work wherever and whenever he wanted to but still have a touch of marketing to it. After all, that was all he knew.

Ten years ago, that dream was a hard one to accomplish. So Kevin stuck it out – stayed in his marketing job until 2013 when a Content Writing job landed in his lap.

Now, Kevin works for Animalz writing articles for their client’s blogs. At first, he wasn’t the best writer (that’s what he tells us 🙂 ) but it didn’t take him long to “find his voice”. And because he writes content for a company that provides a service he is interested in, he loves his job.

His Advice To Remote Workers:

If you’re interested in something, think of different ways to do it. I’ve done marketing for so long, it was hard to break it down into smaller parts of interest. But when I really put my mind to it, I realized I like writing about technical stuff. And I also realized that if I stepped outside my comfort zone, but stayed in the general area of interest, I had more opportunities.  If I liked to do SEO, I would consider looking for a job doing growth marketing. If I thought I would make a good English teacher, I might make a great ESL (English as a second language) teacher. If I was good at managing people, I might want to be a Virtual Assistant.  There are so many ways to look at your job interests.


Wendy is a work at home Virtual Assistant

Wendy “Learn all you can, then learn some more.”

4 Years Working Remotely

Job: Freelance Virtual Assistant

Wendy reminds me a lot of myself. She doesn’t have a college degree. She knows a little about a lot of things but she’s not an expert in anything. For a long time, she wasn’t sure what she really wanted to do, she just wanted to make money and be happy. Wendy has a background in Human Resources, bookkeeping, and office management. Every few years, she was able to seamlessly go from one job to another, sticking it out until something better came along.

One day, Wendy decided to give freelancing a try. She wanted to have more control of her day-to-day life. She knew it would be tough, but she was willing to give it a try. Her background gave her the opportunity to focus mostly on what she liked to do best so she thought she’d give it a go and become a Virtual Assistant.

Her Advice To Remote Workers:

I wasn’t really happy with the jobs I had in my past. Yeah, I picked up a lot of skills that I knew would transfer well somewhere but I didn’t have the freedom I wanted. So there I was: driving 30 miles to a job that was just ok trying to expand on the skills I already had. I did some online research and found a few Virtual Assistant companies that were hiring, Belay and Fancy Hands, but I could only work those jobs part time. I was too chicken to quit my day job.

After about 2 years, my friend talked me into joining Upwork (they used to be called elance). She thought I had what it took to be a freelance Virtual Assistant. Me…not so much. Until I got my first client. And that’s when I knew this was for me. So I read everything I could about becoming a Virtual Assistant. I mean, I took online courses, read e-books, studied what other freelancers offered and charged. I never stopped learning.  The more information I absorbed, the better I became and the more money I made.


Eric is a remote worker

Eric “Think like a remote worker, not a lazy worker”

Just Under 5 Years Working Remotely

Job: Content Creator at Aha!

As a creative writer, Eric knows he can get a job just about anywhere. Even if it’s writing his own blog.

He’s done some writing for greeting card companies and one-off projects he’s found on the Problogger.com job board. When he landed his current job, with Aha! he figured things couldn’t get any better. That was until he was told he would be working remotely. Talk about having a great job, decent pay, doing something he loved, and getting to work from home.

But he made some mistakes…

His Advice To Remote Workers:

When I first started working from home, I thought I could do whatever and whenever. That’s not always the case. Sure, I get a lot of freedom – especially with such a cool company. But the truth is, it took me a while to embrace the remote working lifestyle. I had to train myself to be disciplined in my hours, not only for the sake of getting things done on schedule but for my family. When I first started working remotely, I rolled out of bed whenever I felt like it and plopped myself in my chair and did as much work as I felt like doing. Which at first wasn’t much.

But I gotta tell ya, that kind of schedule was beginning to get to me. In all honestly, I was lazy. I was cutting it close to too many of my deadlines. And that was pretty stressful.

I had to make a change if I wanted to keep on working from home. I had to start thinking like a REMOTE WORKER, not a LAZY WORKER. So I made a few changes. I created a dedicated place to work (a humble corner in the living room) and set up a real office setting. I got up before the kids to get a little work done because I knew things could change every day and I might be the one to pick them up after school. I walk Jimby (my loveable little schnauzer) at the same time everyday. Which he loves. What I have found is I can work a great remote job AND still have a flexible schedule.  I just had to buckle-down.


Put This Wisdom To Work

It might take you a while to get the perfect remote job but don’t stop looking for it.  You’ll make a few mistakes, learn a few lessons, go through a few jobs but it will come to you.  Take this post as a bit of work at home advice that you can really use. Please feel free to leave a comment below to brag about your work at home job.



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