Why Freelancing is the Best Career Choice I’ve Made (So Far)
September 12, 2015

Why Freelancing is the Best Career Choice I’ve Made (So Far)

Being a freelancer isn’t easy. Let’s be real.

It can be a lonely, isolating existence. There’s no such thing as job security, ever. And tax season is pretty much a nightmare.

But for all its frustrations and challenges, I love it. I don’t want to say I’ll never go back to the corporate world, because I’ve learned to never say never. But working for myself as a freelancer has, without a doubt, been one of the best career choices I could have made for myself.

I recently hit the three-year mark since I said goodbye to my steady paycheck, my health benefits, and my 401(k) employer match. It’s been a winding road, paved with plenty of tears, sleepless nights, and debilitating self-doubt, but I wouldn’t trade any of it for all those cushy benefits I gave up. Here’s why.

I get to do what I love, on my terms.

Okay, so stay with me here. This isn’t the part where I launch into some cliché motivational speech about how you should just quit your day job and ‘follow your passion,’ and then your life will be perfect, and you can thank me later.

I certainly didn’t just up and decide one day to follow my passion, and then life was sunshine and daisies from then on. There was no 4 a.m. epiphany – no “Who’s coming with me?!” moment, à la Jerry Maguire (although that would have made things a lot more interesting).

I just knew for a long time that something didn’t feel right with my past jobs. I felt creatively stifled and uninspired with my work. Finally, I reached a point when I knew it was time for a change. A big one.

Working as a freelance marketer and photographer has allowed me the freedom to explore what aspects of my work I truly love, and what I don’t — a luxury I didn’t have in past roles that were more rigidly defined.

It’s also illuminated my strengths and weaknesses in ways that no other job ever has for me. This has helped to guide me when deciding what projects I take on, whether it’s related to photography or marketing or both, so I’m able to do more of what I enjoy and what I do best — and ultimately, feel a whole lot happier.

Amanda Mathson, Freelance Photographer

The early days when I was still exploring photography as a hobby - Photo by Mike Lee, Focus97.com

It’s taught me to be more self-reliant.

When someone hires you as a consultant, whether it’s in marketing or something else, they expect you to provide them with answers. If you don’t know the answers, you need to be able to find them. If you can’t find the answers, you need to have a good reason why. Otherwise, there’s a chance you might not hang onto that client relationship for the long haul.

This can be scary, obviously. I’ve had so many moments since going it alone when I’ve needed a clear answer where there is none; there’s no one who can tell me exactly what I should do. It’s all up to me.

Sure, you can’t step onto Muni in San Francisco without awkwardly rubbing shoulders with another marketer, so I’m literally surrounded by potential resources. And of course, there are networking groups and tons of online resources as well, including my best friend, Google.

But no matter what advice I get from anybody else — at the end of the day, the responsibility to decide what to do with any project (or my business, for that matter) is mine, and mine alone.

Being in such a position of constant self-reliance has not only strengthened my confidence in my own skills, but it’s forced me to learn more on my own. And on that note…

I’ve learned more, faster.

“I am always doing that which I cannot do, in order that I may learn how to do it.” – Pablo Picasso

In order to stay competitive and keep up with the pace of Silicon Valley, I’m required to keep my skills sharp and learn more about my crafts whenever I have the opportunity. I’m always learning new things and trying to do so as quickly as possible, so I can continually become better at what I do.

It’s not uncommon for me to have to absorb a large amount of information in a painfully short period of time. Like, a ‘why-the-hell-do-I-put-myself-through-this’ period of time.

As a result, the trajectory of my skill development, which had crept along at a gradual incline during most of my career, hit a sudden spike once I went out on my own because of the rate at which I was suddenly learning a lot of new things.

The amount of information out there for me to take in has at times been overwhelming, but mostly it’s incredibly exhilarating. There’s always something more I can learn and new ways for me to grow. Obviously, this is true for anybody — but in my role as a freelancer, I feel the motivation and excitement to learn more is stronger than ever. 

In short, it’s all been worth it.

Being a freelancer isn’t for everyone, to be sure. It can be damn hard. I still have moments that creep up on me when I wonder whether I should opt for more stability and just get a steady job working for somebody else.

But through all the ups and downs of my freelance career so far, dare I say I’m becoming stronger at what I do at what seems to be an accelerated pace, and I’m also learning more about myself on a personal level. Even better, I’m continually excited and inspired to learn more. So, is it all worth it? I’m inclined to think yes, definitely.

So, what about you? Do you work for yourself? What’s been your experience?

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