Dear Freelancer: Everything is Possible

Dear Freelancer: Everything is Possible

Freelancers are faced with seemingly insurmountable challenges daily. Yet, we keep doing it… and we’re still not sure exactly how. Here’s my story of becoming truly free.


“I’m not a digital nomad yet,” the petite German woman standing in front of me was explaining, “But I want to start. For example, I want to sell an eBook. How do I do that? But, I don’t feel comfortable teaching, since I’m pretty new myself. How did you get started? What blogs do you read? Inspire me!”

She thrust her hands out in front of her, palms upward, as if to catch the answers that followed.

Unfortunately, she was already starting off on the wrong foot. You don’t need to read a special blog, have thousands of email subscribers, or be the best at anything to succeed as a freelancer.

The uncomfortable truth, is that you simply must do what it is you’re trying to do. The rest will follow.

This may sound easy, but ‘easy’ is far from the word I would use to describe the freelance lifestyle.

Today, I’m going to share with you my personal freelance story: addressing motivation, financial struggles, and the philosophy that still drives me to pursue whatever I can dream up next no matter how badly I messed up on the last round.

Disclaimer: I have made some terrible mistakes, and numerous financially unsound choices. I do not recommend using my life as a roadmap per say, but I’ve certainly made it this far… so maybe it’s worth taking some notes.

Digging Into Freelancer Characteristics

My mom always told me I was special. I chose to take that idea and run with it. In fact, I took it on a marathon journey and never came back.

Thankfully, my interpretation was that I could succeed at anything I put my mind to. Like Disney always told you: when you believe in your dreams, they come true.

Well, not quite like that. Let me tell you a story.

I’ve been an enterprising entrepreneur since the ripe old age of, oh, say 7 years old. For the life of me, I can’t tell you why I was inspired to create flyers advertising my dog and house sitting services, and then spread them far and wide around our suburban San Diego neighborhood. All I know, is that I did.

Lo and behold, I got clients.

Anne Dorko as a toddler
Imagine entrusting your house to this kid, just slightly older.

…I still need to ask my mom how big of a role she played in this, because I find it difficult to believe that real adults handed their house keys to a 7 or 8 year old, trusting that child to not kill their Dalmatians or set everything on fire while they traveled for business or vacation. I did once drown a giant spider on their counter with Windex and left the carcass there, but that’s a story for a different time.

Throughout the following years, my freelance efforts became bigger and more wide spread. I created an “In Your House” pet washing service (complete with a self printed, branded T-shirt), offered photography for senior year portraits, and generally took on any kind of work I could find that people would hire me for.

The oddest part of these endeavors was that the money itself was never my motivating factor. There was something about freelancing that I couldn’t get enough of, and to this day I cannot pinpoint one single element that it might be.

Another phenomenon was that no matter how old I was, how little experience I had, or how off-beat my ideas were – I always managed to find clients and make something work in my favor.

Now that you’ve suffered with me through my childhood, here are the basic characteristics that I’ve found prepare you for the life of a freelancer.

1) Intrinsic Motivation

If you’re not motivated by something deep inside of you that draws you into the freelance lifestyle every day, even in the face of the unknown, freelance may not be for you. “Living the dream” only counts if it’s actually your dream.

This isn’t something that’s learned, it just is.

Freelancing may sometimes entail sipping cocktails while working from your laptop on a remote and exotic beach, but you’ve also forsaken most of the benefits that come from having a salary, straight-forward taxes, and your tasks managed for you. The freelance lifestyle has its perks, but if it were all feet kicked up in a hammock, everyone would be doing it.

2) Faith In Yourself

Learning to trust that you can succeed is probably the biggest psychological barrier to freelance.

No matter how new or inexperienced you are at something, the only way to turn it into your freelance life, is to pursue it as such. Most people simply don’t. It’s scary to say “Hey, you should pay me for XYZ” with confidence, when you’re just getting started.

Yet, sometimes, asking is all it takes. Seriously. It can be that simple.

Trust yourself to succeed. Have a little faith.

3) Separation of Failures and Self Worth

Of course, not everything pans out the way you expected or hoped that it would.

I’ve always evangelized the power of accepting that everything is temporary, and that especially applies here. Every endeavor you make, every business plan that you attempt, every client you work with – these are all steps towards whatever comes next. Life is always changing, and experiences are just that.

I can say with 99.99% confidence that you have tripped, fallen, or otherwise fumbled in your daily life before. (If you haven’t, please contact me. I want to meet you.) Of course, some situations are more embarrassing than others, but you got up and moved on with your life.

The same goes for your freelancing efforts. You cannot allow a project to become the sole evaluation for your self worth.

Part of what makes freelancing so difficult is that it’s sewn into our souls. We’re working and living our passions. It’s vital that you learn to disassociate individual projects with who you are as a person.

Otherwise, you’ll fall and refuse to get up.

4) Intentional Naivety

There’s a certain amount of naivety that keeps a freelancer going.

When what you want most in life doesn’t seem possible on paper, sometimes, you have to do it anyways. Everything is impossible, until it isn’t.

Waking up and doing the impossible every day can only be your reality if you allow yourself the naivety to not know that it shouldn’t be possible in the first place.

Believing you can do something doesn’t mean you can, but believing you can’t does mean you can’t. Don’t shoot yourself down before you even get started.

On (And Off) the Career Path

Back to my freelancer backstory.

My societally acceptable career path began when I tested out of high school to begin college at 16 years old. “You must be a genius!” people gush. Trust me, that’s far from the case. My most serviceable strength is playing to my strengths.

Thanks to a specialized college I had found when I was 12 years old scouting out my future on the internet, I was able pack four years worth of an education in graphic design, web design, and film editing into the next two years of my life. At the bright young age of 18, I graduated with a Bachelor of Science and was already working within the industry as an entry-level Ruby programmer and web designer. What a shiny bright future I had ahead of me!

Engagement photography by Anne Dorko in 2011
Daily d'aww.

Naturally, my freelance work had already adjusted to match my newly found skills. I built websites for lawyers, fitness instructors, you name it. My side photography gig was shooting to new heights as I worked weddings and engagements.

I was making relatively good money for an 18 year old, but I had no idea who I was or what I wanted to do with my life. As it turns out that my foundational motivations are far from financial, I wasn’t particularly inspired to do anything dramatic or useful with the money I was making.

Unfortunately, this part of my life was occurring around at the same time that the global economy was hitting rock bottom between 2008 and 2010. The amazing startup I worked for ended up being dissolved and the assets sold to Qualcomm.

Long story short, I spent the next year and a half trying to find a job that fit me. Nothing quite seemed a match, and that aside, being laid off more than once starts to get to you.

Anne Dorko squishing her coworkers head in a photo
This was titled 'Cubicle Craziness' in my old files. Thrilling times!

I should mention that I had already gotten myself in and out of $10k worth of credit card debt. I kept one card after that because everyone said it would maintain my credit score over the years. I hadn’t been too worried about its relatively small balance since I was making $45k a year.

Then, without any savings to my name, I quit my last office job at the end of 2011 out of frustration with the management.

I had experienced complete disillusionment about job satisfaction and security. I wanted nothing to do with it any more.

Here are a few of the conclusions I arrived to.

1) A Job is Usually Just That

There’s an overly used phrase saying, “If you love what you do, you never work a day of your life.”

For the kind of person who finds their calling in the heart of freelancing, a normal job is never going to cut it. Even on my best days, I was waking up 2-3 hours before commuting every day to sit in Panera and work on my own pursuits, trying to build something that was unique to me, my visions, and my goals.

No job was going to give that to me.

2) Typical Job Benefits Don’t Motivate

A regular job comes with a lot of perks.

Decent money, set boundaries, community, assigned projects, infrastructure, support, health insurance, set hours, training, and much more all come with a normal career job.

While I understand the appeal of these things for others, the way it was delivered didn’t feel valuable enough for me to want to stay.

I felt I could still find what I needed in the way of community, training, and projects without the overhead and control of working for a company. It irked me that I had to play into bureaucracy and stroke egos to have any of my ideas considered or for my work to have merit.

Freelancing isn’t always a fun process either, but I get to control which compromises I make and choose exactly who I’m willing to work with.

Freelancing Is Knowing Yourself

This brings our story to my 22nd year of life.

In review, I had already spent over four years in the web development and software engineering industry, and was completely jaded. I began questioning why I had wanted to grow up so quickly. What was the point of college and a career if this was all it amounted to?

The grown-up world sucked.

I had two options:

  1. Go full freelance and hope for the best, or
  2. find another job.

It was already in my head to get in the car and drive away to experience new and glorious things that I had never seen before.

I was pulling in decent money on a successful Fiverr gig writing and recording short songs. Of course, I had to turn down some requests, such as the song about Fiasco, the monkey with a foot fetish. But mostly, business was good.

Other than that, I could usually find the odd web design job here and there. It wasn’t much, but I figured that should be good enough to get me through whatever came next.

So I packed my stuff, hopped in the car with my girlfriend at the time, and we drove off with the goal of not returning until we’d hit the 48 contiguous states.

It took seven months, but we pulled it off.

Thus began my insatiable travel lust and the beginning of a long and strange journey which ultimately brings us to my current status of settling down in Cologne, Germany as a freelancer today.

I’ll go back and fill in that giant blank in just a moment, but right now I’d like to discuss how much freelancing has to do with getting to know yourself on a seriously intense level.

1) Without a Reason, It’s All Pointless

Freelancing is hard.

If you’re not into working numbers, it’s especially difficult to make yourself focus on the financial side of things, which can really bite you in the ass.

That means you’re going to have moments where you’d like to eat lunch, grab coffee, or hang out at the bar but you simply can’t. You simply don’t have anything in your bank account. It’s not only frustrating, but embarrassing.

If you don’t have sufficient motivation to deal with difficult times, you’re going to go crazy. You need to know your reason for doing this. You need to know why it’s worth it.

Which brings us to…

2) There Are Huge Sacrifices

For me, being successful means I can do what I want.

Most people interpret this as a direct fiscal number that translates into the average cost of whatever their goals are. For me, it’s a little different.

In my experience, doing the the things the way you’re supposed to is a trap. The world is setup as a giant sales market, and I find that that to be terrible. While I appreciate having a padded budget and full bank account because that lets me eat and enjoy life, I don’t actually like dealing with money.

That’s why my philosophy is that you simply do what it is you want. You find a way for it to work. Because of this I do a lot of trade, and it’s the only way I’ve gotten to partake in amazing experiences, from riding in a helicopter over glaciers in New Zealand to taking intensive German language courses for 3 months.

I let go of everything in my life that isn’t of utmost importance, as often as possible. Freelance is the key for me to achieve that.

The less I require in overhead, the less money, time, and everything I need to get what I want and live how I want. If you’re willing to put everything that isn’t important to you on the back burner, you can make freelancing work for you. It’s almost a guarantee.

You need so much less than you think to be happy. For me, freelancing isn’t just my job, it’s my way of life.

The thing is, none of this works if you don’t know what it is about yourself that drives you.

3) You Spend a Lot of Time Alone

By nature, you’re working solo on a lot of projects as a freelancer.

You have to build your own community, seek out events and groups to join, and that can take a lot of energy if you’re not a natural extrovert. If you’re in a small town, it’s that much harder to find the right group.

Spending a lot of alone time means getting stuck in your thoughts. You’re going to be up there, you might as well make friends with yourself and learn what works for you (and what doesn’t).

It’s Not Always Freelance

Here’s the thing about freelance – you don’t always have to do your normal freelance work to make money. You’ve got the time and availability to take on odd jobs whenever you want.

For me, that means interesting gigs and seasonal work.

Let’s go back to the part where I finished my seven month road trip around the states and review what work I did over the next four years, all the while keeping up some form or another of my freelancing.

  • 2012, San Diego: Taught PHP & JavaScript at Platt College
  • 2013, Austin: Car saleswoman, Bicycle assembler, Brand ambassador
  • 2014, Worldwide: Assistant photographer to a traveling art model
  • 2015, Yellowstone: Server at a resort

Not exactly your normal resume, is it?

Most of these jobs came from curiosity. You hear about car salesman, but have you tried selling cars before? Probably not. Have you ever gotten in a van full of strangers at 5:30am to drive 2 hours to a remote Walmart and assemble bicycles in the back all day? I have. It was a very unique experience.

Each of these has their own stories and characters, with different invaluable lessons I learned while I was there.

My freelancing allowed me to try new and interesting things that any normal job wouldn’t have. When you realize that in a serious pinch, you can go serve tables and earn $8k+ over the summer while spending most of your time relaxing in a world-renowned National Park… well, freelance doesn’t sound so scary anymore.

“That’s not being a freelancer! That’s cheating!” you may be thinking. Sure. Maybe. But that’s why you have to know what’s important to you and put that first. For me, traveling and having interesting experiences is always first and foremost.

I’m not going to forgo intriguing opportunities for the sake of being a purist freelancer.

Hairy coo looking shocked in the Scottish Highlands
And frankly, my friend here and I are shocked that you'd suggest it.

There are many more details to this story: how I found these jobs, how I got in and out of $10k a second time, how I took a month off to cycle from San Diego to Salt Lake City, and more… but there just isn’t enough time to cover that right now.

Where Does That Leave Us?

I really hope the German woman I met asking for advice at the Digital Nomads MeetUp.com event goes on to write her eBook and find her success. She deserves it as much as anyone.

Most people want to become a freelancer because of the freedom it provides.

I’m here to tell you that there’s no one right way to be a freelancer, and if you’re willing to live outside the box, you can do more than you realize is possible.

Going off the beaten path is hard and lonely sometimes, but that’s why I’m always connecting with people who feel the way I do so we can help each other through the rough patches.

I’m not a raging success in the eyes of any business model, but my personal life is rich and I am happy. My work supports me the way I need it to, and the more I understand what’s important to me, the better I am able to wield it. I can honestly say I do not regret any of the choices I’ve made that led me here.

Ultimately, isn’t that why people look at work alternatives such as freelancing? So that they can feel that way, too?

So, I’m curious to hear your questions, thoughts, and stories in the comments below. And if my story resonated with you, I encourage you to share it with a friend.