Freelancing & Me, We’re Meant To Be

This post was last updated on 2019 November 17

I’ve had this aching feeling ever since I entered the professional workforce 9 years ago that the typical 9-5 office job just wasn’t for me. Committing to spending my weekday daylight hours at a desk surrounded by others who have agreed to the same sentence feels completely unnatural and inefficient to me.

I’ve worked office jobs on both sides of the spectrum: some where I and most everyone around me were woefully underutilized and unfulfilled, and would take extended lunch breaks undetected and conspire to look busy and kill time til 5:00; others where we all had never-ending to do lists and were expected to answer work messages after hours. Every office job I’ve had has ended the same way: with me quitting to take some time to myself to travel, pursue other interests, and do some soul searching. I’ve never left a job having another job lined up.

Clearly this lifestyle isn’t sustainable. I don’t want to spend my life suffering through a job for 1-2 years at a time, biding time before my bullshit threshold is reached and I quit in exasperation, repeating this cycle forever and ever amen. I want to live a well-balanced life that flows and allows for freedom and growth.

Great Ocean Road
Torquay, Great Ocean Road

Seeking An Alternate Path

Look, the world needs people who are happy to work those 9-5 office jobs. What it doesn’t need is for others (like me) to work those jobs when they aren’t suited for it. Everyone suffers when that happens.

The amazing thing is that we’re now living in an age where we have other options to make a living, with more and more people opting out of a typical office environment. Anything other than following the traditional path towards achieving the American Dream was unheard of when I made the regrettable decision 13 years ago to throw down money I didn’t have on a degree I didn’t know I wouldn’t need. Still, I am so incredibly glad that today I have a choice – I’m able to walk away from the life that was all set up for me to cruise through on autopilot, and instead choose a new path that makes me feel alive every day with all its struggles and wins.

Freelancing as a digital nomad
Temporary home office while house sitting in Melbourne, Australia

To Start A Business, Or Not

Up until recently, I thought that starting my own business would be the ultimate way to freedom. I actually had a wedding photography business that I ran part-time for 5 years in NYC alongside my office job – I thought I’d work hard to build up my business, then quit my office job once I felt like I’d make enough money solely by shooting weddings.

Spoiler alert: that never happened, but I quit my job anyway.

I believe that if I really wanted to be a wedding photographer, and if it were truly what I was meant to pursue as a career, then I would have made it happen. There are thousands of others out there who have done it, and with my skills and discipline there’s no reason why I can’t do it too.

The thing about being a business owner is that you’re responsible for EVERYTHING. Whether you outsource certain tasks or take everything on yourself, it all rides on you. There is always something more you could be doing to build your business, and often it’s very difficult to draw the line between your work and your personal life. I’ve seen a lot of business owners take on insane work hours at the expense of other aspects of their life (and also a few who have struck an ideal balance, but they’re unicorns). Maybe they thrive under pressure, are addicted to the feeling of accomplishment, or have gotten themselves in way over their head – whatever their motivation, I’m not judging, I just don’t happen to share it.

I’ve realized that at this point in my life, small business ownership just isn’t my style. I highly value the work-life balance and vastly prefer focusing on a few specific tasks or projects and then wiping my hands clean and moving on to the next. I don’t want to worry about bookkeeping AND sales AND marketing AND customer service AND product/service delivery, nor can I be arsed to outsource most of it and then have the burden of overseeing everything. Simply put, I have way too many other interests and hobbies that I’d rather focus on – I am not my work.

Digital nomad freelancing

Behold, Secret Option C: Freelancing!

I don’t think I fully understood what freelancing was, exactly, until I threw myself into some work-like projects in a frantic attempt to start making money late last year, and then sort of woke up one day and was like: waiiiiiit a second, am I a freelancer?

If I had, I totally would have gone down this path a lot sooner because it turns out that freelancing is an amazing fit for me, for all of the following reasons (and more that I probably can’t think of at the moment):

  • I get to wake up at whatever time feels right to me and enjoy the start of my day savoring a cup of homemade coffee and catching up on posts on my Feedly and various social media feeds. Or I might set my alarm in time for the 9:30am yoga class. I’ve never been a morning person, and I don’t see why I should have to be in order to get my work done.
  • I don’t have to start my workday til the afternoon once I’m back from yoga, showered, and fed (or at all, if I feel like taking the day off).
  • I don’t have to wait for a table with the weekend brunch-goers ‘cause I can do brunch on any day of the week.
  • I can take a break from working whenever I want and for as long as I want, go for a bike ride or late afternoon yoga class to get the blood flowing, then resume work a few hours later feeling refreshed and ready to work more effectively.
  • I’m able to work in the evening, which suits me well ‘cause I’m a night owl and can work on full blast til about 10pm.
  • My schedule is almost always completely flexible, which means I’m the easiest to make plans with.
  • I can work from anywhere, as long as there’s internet. This includes, but is not limited to: coffee shops, my bed, someone else’s bed, the couch, the dining room table, porches, balconies, the park, poolside, the train, a tent, hostels, tropical islands, other countries (yes, I’ve worked from all of these).
  • I’m not limited to X vacation days per year and can go away whenever I please, for any length of time. AND, because I can work from anywhere, I’m able to stay away longer and combine work days with play days.
  • If a cheap flight pops up, or a gratuitous travel opportunity presents itself, I can go for it without asking anyone’s permission.
  • I don’t have to deal with the drama, pointless meetings, ass kissers, imbeciles, and hierarchical bullshit that inevitably accompany any office job.
  • I get to choose which projects I want to take on, and how many hours I want to work. This ensures I never let anything job-related skew my precious work-life balance, and never take on a project that doesn’t excite me.
  • I can utilize a variety of skills and work on all sorts of different projects without being confined to a rigid job title. I’m not *just* a photographer, or writer, or SEO specialist, or Salesforce consultant – I’m all of these and more.
  • I get to set my own wages.
  • I only have to worry about kicking ass on the projects I’ve taken on, nothing more.

That all sounds idyllic, but there are plenty of downsides to freelancing as well: namely lack of benefits and stability. It’s definitely not for someone who needs security and routine.

But if you’re on Team GSD (Get-Shit-Done) like I am, just want to work hard on a project on your own time and terms without all the nonsense that wastes your time and energy during a typical day at the office, and have some profitable skills that lend themselves well to working independently and remotely, freelancing just might be your ticket to work-life happiness.

Do you have any tips or resources you can share on how to make it as a freelancer? (I’d love to share them in a follow-up post!)