What I’ve Learned in 4 Years of Freelance Writing

Date Posted: January 29, 2019
Posted in: Freelance Writing

What I've Learned in 4 Years of Freelance Writing

I have been full-time freelance writing for four years now, which is also the longest time I’ve spent in any single job in my life! It’s amazing how quickly time can pass. It is also incredible how slowly certain days can seem to drag on. I’ve learned an incredible amount from these years of freelancing, including the following valuable lessons…

Freelancing is Effing Hard

Freelance writers have learned to use equipment like laptop stands to work from home

Look. If you look at my life and think it’s all sunshine and roses, you’re mostly right. I am incredibly privileged and lucky. But I also bust my ass for the lifestyle that we choose to have. I have a great many advantages that allowed me to get to this starting point; I am grateful for that. But freelancing is freaking hard.

Being self-employed means I need to pay additional taxes and run all aspects of a business by myself. But freelancing means all that, plus I don’t even have steady work.

I prefer long-term clients, which is a way of creating steady work for myself. But that isn’t always the way it works out as a freelancer.

The variety of work is fascinating and challenging and fun.

Working as a freelance writer with a glass of wine

The variations in income can be incredibly stressful as you stare at bills and expenses that you simply can’t pay.

It’s a constant hustle because nobody else will pick up that slack. But it’s also the most rewarding work when you get to look back and realize that everything you accomplished professionally was entirely due to your hard work. Nobody else helped, nobody else contributed…there were no group projects or team efforts here. So taking a moment to self-congratulate is vitally important.

Working Remotely Has Pros and Cons

Working alone requires self-discipline and immense effort. You need to create your own opportunities in every aspect of life. That includes everything from your now-limited social interactions to your professional networking. Working from home can be marvelous, but it does not suit everyone.

I have ebbed and flowed on my adoration for working from home. When I have a comfortable space plus easy access to cafes and libraries for alternative options, I have my best combination of preferred work environments.

One of the best parts of freelance writing is working with a cat in your lap

When I work from home and feel otherwise isolated, it gets weird. In Ireland, I pretty much only talked to the horses, sheep, and the dog we looked after for a while. It was not ideal.

But when we lived in Malta and I could work at home after walking to the sea and taking a morning swim, I was lighthearted and happy. I could also pop out to any of the plethora of cafes or bars to get more work done when I wanted a change of scenery. I felt alive and excited!

Freelance writers also often work from cafes

Freelancing is a constant hustle and it might require constant changes and incredible flexibility. But you’ll sure as hell learn a lot about yourself in the process!

Freelancing Allows for Flexibility

Working remotely and without set office hours allows for much greater flexibility in how and where you choose to work.

Freelance writing means you can work from a pub with a beer

I’ve written on trains and planes; I most often start working while still in my pajamas, but I also like to bring my laptop along for a day out in the city where I can write for a bit and wander for a bit, too.

When you work on your own schedule, you learn about your preferences and your strengths. The main things I’ve learned:

  1. I am not a morning person. Trying to write in the mornings takes me approximately twice as long to accomplish a similar task later in the day. So I use my mornings to relax, read the news, and catch up with my friends and family who are 5 hours behind me and inevitably left me multiple messages while I slept.
  2. Cats love laps and laptops. We’ve done lots of house and pet sitting with TrustedHousesitters (and for friends!) in various countries. It is a universal truth that cats love laptops and sitting on the laps of humans with laptops. It’s just a thing, and I’m in love with it! It certainly makes for a fun workday…all offices should have office cats, IMO.
  3. Coffee is fuel. Cafes, therefore, make for great places to work! However, not all cafes are equal. I love supporting local, family-run businesses. But I also realize that I’m not offering much support by taking a table for 5 hours while paying for just 2 lattes. So if I plan to park at a cafe for a while, I go to the big chains where the WiFi is often more reliable, where outlets are plentiful, and where I have zero impact on their bottom line if I camp out.
  4. Wine is also fuel. As is beer. I love working at a bar or pub! The energy is fun and too much coffee gives everyone the jitters anyway. Finding a good bar to work at is also an art…but I find at least one in every country!
  5. I am deadline-driven. When I have tons of time to work on something, I will still wait until it is due. It’s not procrastination as much as it is time management. If I have five hours to work on something, I’ll finish it in five hours. If I have five weeks, I will still finish it in five hours. Starting it five weeks in advance simply means I will dawdle over it and distract myself from other projects I could be doing instead.
  6. I am also cold-averse. It is not unheard of for me to type blindly from underneath a blanket…or to use fingerless gloves…or to type with one hand while the other holds a hand warmer. “Give me liberty sunshine or give me…” awkward work habits?
American expat blogger Amanda Walkins working on her computer in a cold room

If you work remotely for yourself with no set hours, that flexibility can grant you the flexibility to optimize your time. By figuring out how and when you work best, you increase your productivity and maximize your energy. This isn’t an option with regular office hours, so I revel in the flexibility my freelancing offers!

This is a New Way to Work

My grandfather worked until he was 83 years old, entirely by choice. He loved his job and he was damn good at it so he carried on well past the typical retirement age.

Perhaps it was his example or perhaps it is the changing times, but I do not foresee retirement as an end goal to reach before life can begin. I actually consider myself retired already!

Benefits of freelance writing include warm cats as coworkers

I did the office job for a few years, loved it, but opted to let it go in lieu of a different lifestyle.

By now, I have been living that lifestyle for longer than I’ve done any other job in my life thus far and have zero regrets about the decision.

I think sometimes it’s tough for older generations to see some of us striking out and breaking the mold so carefully crafted for us. But our futures do not look like theirs. Retirement is not a given for us. We cannot rely on the comfortable life that a steady 9-5 office job for 40 years once offered.

Clocking-in and clocking-out while buying a house on a single income faded away into history. We also can’t “have it all” – whatever that is supposed to actually mean.

Freelance writing on a train

Rather, we’re creating a new working world, where we can work remotely and therefore live wherever suits our preferences, eliminating the commute and the economic crush of housing deficiencies seen in many urban areas.

We can freelance, or contract, or become entrepreneurs or digital nomads or whatever other moniker we select because our options have increased multi-fold.

Yet, within those options, many of us also understand that the “hustle” and the “grind” is the only mainstay to such a professional existence. Alas, balance in all things, and I have enjoyed choosing the flexibility of location and daily life over the commute and fluorescent lights.

Being Your Own Boss is Badass

Freelance writers can work outside and enjoy the sunshine

My days vary and I am in charge of my own schedule. This is magical but also puts all the pressure on me to ensure that every deadline is met, every project is organized, and every client is happy.

I have nobody looking over my shoulder, which is wonderful! But I also have nobody who can help me out, which can be isolating and challenging.

Luckily, there are so many groups and collaborative efforts among freelancers online that I’m never truly alone. Whether it’s just to vent frustration or to ask for advice, the interwebs have offered us lonely work-from-home types so many options.

That being said, at the end of the day the entire business is on my shoulders.

Don’t do the work, don’t get paid.

Don’t do the work while also highlighting the previous work to build your profile while also searching for, pitching, and negotiating the next project…don’t get paid.

Freelancing is all about self-discipline. If I’m perfectly honest, I’ve written this whole post while procrastinating paid work that’s due for a client. Sometimes, taking my mind off of that work and delving into another topic altogether helps. Other times, I’m just pushing off the inevitable. And it’s just going to kick my butt in the end!

Working remotely means you can work from anywhere

Alas, off I go for more SEO content writing…I’ve procrastinated enough for today!

Time to go be a boss lady. Because I’m in charge and I love it!


Liked this post? Pin it!

With four years of freelance writing under her belt, American expat blogger Amanda Walkins shares what she's learned so far.

If you’re new here, feel free to check out my many former homes in  HondurasEcuador, SpainScotlandIreland, and the Mediterranean island of Malta.

We also housesit and petsit our way around the world. You can learn all about TrustedHousesitters (our preferred housesitting website) here.

You can follow along on our adventures by subscribing to my newsletter below, and join me on social media, too! I’m on FacebookInstagramTwitter, and Pinterest. See you there!

I have been full-time freelance writing for four years now, which is also the longest time I’ve spent in any single job in my life! It’s amazing how quickly time can pass. It is also incredible how slowly certain days can seem to drag on. I’ve learned an incredible amount from these years of freelancing, including the following valuable lessons…

Freelancing is Effing Hard

Freelance writers have learned to use equipment like laptop stands to work from home

Look. If you look at my life and think it’s all sunshine and roses, you’re mostly right. I am incredibly privileged and lucky. But I also bust my ass for the lifestyle that we choose to have. I have a great many advantages that allowed me to get to this starting point; I am grateful for that. But freelancing is freaking hard.

Being self-employed means I need to pay additional taxes and run all aspects of a business by myself. But freelancing means all that, plus I don’t even have steady work.

I prefer long-term clients, which is a way of creating steady work for myself. But that isn’t always the way it works out as a freelancer.

The variety of work is fascinating and challenging and fun.

Working as a freelance writer with a glass of wine

The variations in income can be incredibly stressful as you stare at bills and expenses that you simply can’t pay.

It’s a constant hustle because nobody else will pick up that slack. But it’s also the most rewarding work when you get to look back and realize that everything you accomplished professionally was entirely due to your hard work. Nobody else helped, nobody else contributed…there were no group projects or team efforts here. So taking a moment to self-congratulate is vitally important.

Working Remotely Has Pros and Cons

Working alone requires self-discipline and immense effort. You need to create your own opportunities in every aspect of life. That includes everything from your now-limited social interactions to your professional networking. Working from home can be marvelous, but it does not suit everyone.

I have ebbed and flowed on my adoration for working from home. When I have a comfortable space plus easy access to cafes and libraries for alternative options, I have my best combination of preferred work environments.

One of the best parts of freelance writing is working with a cat in your lap

When I work from home and feel otherwise isolated, it gets weird. In Ireland, I pretty much only talked to the horses, sheep, and the dog we looked after for a while. It was not ideal.

But when we lived in Malta and I could work at home after walking to the sea and taking a morning swim, I was lighthearted and happy. I could also pop out to any of the plethora of cafes or bars to get more work done when I wanted a change of scenery. I felt alive and excited!

Freelance writers also often work from cafes

Freelancing is a constant hustle and it might require constant changes and incredible flexibility. But you’ll sure as hell learn a lot about yourself in the process!

Freelancing Allows for Flexibility

Working remotely and without set office hours allows for much greater flexibility in how and where you choose to work.

Freelance writing means you can work from a pub with a beer

I’ve written on trains and planes; I most often start working while still in my pajamas, but I also like to bring my laptop along for a day out in the city where I can write for a bit and wander for a bit, too.

When you work on your own schedule, you learn about your preferences and your strengths. The main things I’ve learned:

  1. I am not a morning person. Trying to write in the mornings takes me approximately twice as long to accomplish a similar task later in the day. So I use my mornings to relax, read the news, and catch up with my friends and family who are 5 hours behind me and inevitably left me multiple messages while I slept.
  2. Cats love laps and laptops. We’ve done lots of house and pet sitting with TrustedHousesitters (and for friends!) in various countries. It is a universal truth that cats love laptops and sitting on the laps of humans with laptops. It’s just a thing, and I’m in love with it! It certainly makes for a fun workday…all offices should have office cats, IMO.
  3. Coffee is fuel. Cafes, therefore, make for great places to work! However, not all cafes are equal. I love supporting local, family-run businesses. But I also realize that I’m not offering much support by taking a table for 5 hours while paying for just 2 lattes. So if I plan to park at a cafe for a while, I go to the big chains where the WiFi is often more reliable, where outlets are plentiful, and where I have zero impact on their bottom line if I camp out.
  4. Wine is also fuel. As is beer. I love working at a bar or pub! The energy is fun and too much coffee gives everyone the jitters anyway. Finding a good bar to work at is also an art…but I find at least one in every country!
  5. I am deadline-driven. When I have tons of time to work on something, I will still wait until it is due. It’s not procrastination as much as it is time management. If I have five hours to work on something, I’ll finish it in five hours. If I have five weeks, I will still finish it in five hours. Starting it five weeks in advance simply means I will dawdle over it and distract myself from other projects I could be doing instead.
  6. I am also cold-averse. It is not unheard of for me to type blindly from underneath a blanket…or to use fingerless gloves…or to type with one hand while the other holds a hand warmer. “Give me liberty sunshine or give me…” awkward work habits?
American expat blogger Amanda Walkins working on her computer in a cold room

If you work remotely for yourself with no set hours, that flexibility can grant you the flexibility to optimize your time. By figuring out how and when you work best, you increase your productivity and maximize your energy. This isn’t an option with regular office hours, so I revel in the flexibility my freelancing offers!

This is a New Way to Work

My grandfather worked until he was 83 years old, entirely by choice. He loved his job and he was damn good at it so he carried on well past the typical retirement age.

Perhaps it was his example or perhaps it is the changing times, but I do not foresee retirement as an end goal to reach before life can begin. I actually consider myself retired already!

Benefits of freelance writing include warm cats as coworkers

I did the office job for a few years, loved it, but opted to let it go in lieu of a different lifestyle.

By now, I have been living that lifestyle for longer than I’ve done any other job in my life thus far and have zero regrets about the decision.

I think sometimes it’s tough for older generations to see some of us striking out and breaking the mold so carefully crafted for us. But our futures do not look like theirs. Retirement is not a given for us. We cannot rely on the comfortable life that a steady 9-5 office job for 40 years once offered.

Clocking-in and clocking-out while buying a house on a single income faded away into history. We also can’t “have it all” – whatever that is supposed to actually mean.

Freelance writing on a train

Rather, we’re creating a new working world, where we can work remotely and therefore live wherever suits our preferences, eliminating the commute and the economic crush of housing deficiencies seen in many urban areas.

We can freelance, or contract, or become entrepreneurs or digital nomads or whatever other moniker we select because our options have increased multi-fold.

Yet, within those options, many of us also understand that the “hustle” and the “grind” is the only mainstay to such a professional existence. Alas, balance in all things, and I have enjoyed choosing the flexibility of location and daily life over the commute and fluorescent lights.

Being Your Own Boss is Badass

Freelance writers can work outside and enjoy the sunshine

My days vary and I am in charge of my own schedule. This is magical but also puts all the pressure on me to ensure that every deadline is met, every project is organized, and every client is happy.

I have nobody looking over my shoulder, which is wonderful! But I also have nobody who can help me out, which can be isolating and challenging.

Luckily, there are so many groups and collaborative efforts among freelancers online that I’m never truly alone. Whether it’s just to vent frustration or to ask for advice, the interwebs have offered us lonely work-from-home types so many options.

That being said, at the end of the day the entire business is on my shoulders.

Don’t do the work, don’t get paid.

Don’t do the work while also highlighting the previous work to build your profile while also searching for, pitching, and negotiating the next project…don’t get paid.

Freelancing is all about self-discipline. If I’m perfectly honest, I’ve written this whole post while procrastinating paid work that’s due for a client. Sometimes, taking my mind off of that work and delving into another topic altogether helps. Other times, I’m just pushing off the inevitable. And it’s just going to kick my butt in the end!

Working remotely means you can work from anywhere

Alas, off I go for more SEO content writing…I’ve procrastinated enough for today!

Time to go be a boss lady. Because I’m in charge and I love it!


Liked this post? Pin it!

With four years of freelance writing under her belt, American expat blogger Amanda Walkins shares what she's learned so far.

If you’re new here, feel free to check out my many former homes in  HondurasEcuador, SpainScotlandIreland, and the Mediterranean island of Malta.

We also housesit and petsit our way around the world. You can learn all about TrustedHousesitters (our preferred housesitting website) here.

You can follow along on our adventures by subscribing to my newsletter below, and join me on social media, too! I’m on FacebookInstagramTwitter, and Pinterest. See you there!

About the author

Amanda Walkins

Serial expat Amanda Walkins is a freelance writer & blogger. She has lived in 7 countries, traveled to many more, and loves helping people explore the world through slow travel (like house and pet sitting!) and living overseas.