Reflections on freelancing: It's all in the approach
Get out there and make it happen
Hey reader,
Back at it this week after a couple-week hiatus due to childcare snafus. This week’s essay is a sprucing up of a blog post I wrote in 2017. Earlier this week I was updating my portfolio website and got sidetracked by re-reading some of the old posts I’d written for the site’s blog, which has long since been taken down.
A few were cringeworthy. But others retained their value and even inspired me enough that I decided to share a conglomeration of points here. They’re written to hard-working freelancers and self-employed professionals.
Community shoutouts
Welcome to the two dozen new subscribers since the last dispatch! Whatever you’re doing professionally, I hope your location independence provides the inspiration to keep going.
Shamelessly shouting out myself this week for the publication of an article I wrote about my snowboard trip to Kyrgyzstan. The trip was a big undertaking — it required months of training and caused a good deal of stress in the weeks leading up to it. It was incredible, but I’m glad it’s in the rearview mirror.
Finally, I will be in Mexico City next week — if you’re around, let’s grab a beer! Shout me a response to this email.
Now, let’s get inspired.
Reflections on freelancing: It's all in the approach
Here I’ll lay out the things I’ve found that work for me, some advice I’ve received along the way, and dispel a few pining notions that many of us writers seem to have as we enter the business. This list is primarily meant to serve as a daily reminder to myself and is far from complete, but hey, that’s the beauty of blog posts – I don’t have to impress an editor and the list can be addended later.
For you, dear reader, perhaps this list can provide a bit of an attitude adjustment during the inevitable down cycles of self-employed remote work. Sometimes, looking at your situation from a new vantage point can help turn a fearfully slow and unproductive week into one of hope, self-appraisal, and reconciliation.
First and foremost, look at the real value of assignments.
Let me be loud and clear about my support for the ‘freelance isn’t free’ argument. We all need to make a living. But one of the catch 22s of this line of work is that many assignments and contracts offer value far beyond the financial reach of the work. I learned quickly that sometimes, especially as a newbie, a byline in a credible publication or a hefty dose of networking is equally as valuable as the crappy-to-mediocre article rates offered by most online pubs.
For me, one of the steepest learning curves of self-employment has been honing in on the long-term value in a piece of work before deciding whether or not it’s worth my time. A $200 stipend for an article based on a trip I took definitely isn’t reimbursing my cost, but if I play my cards right, having the editor on my contact list and the byline in my portfolio will pay off down the line.
Whether that’s better pay for a long-form feature down the line or a referral to an assignment for someone else, keeping the work train moving is an absolute necessity if you’re going to stay afloat working from your laptop. Freelancing is a case study in trickle-up economics -- work your ass off, strive to get better at what you do, and good things will follow.
Tip: Finding work can be tough when you’re starting out. But among the one-off press releases and 300-word listicle gigs I found myself – sometimes – landing, I managed to secure a contract with a small travel website that I found through the Matador Creators Marketplace. While the pay was crap (only 1 cent per word), the publisher came through when I needed an assignment letter to land a press trip and couldn’t get one elsewhere. They’re also pretty lax about what I write about, and it in those early days i benefitted me more than once to be able to tell a PR rep ‘Yes, I can guarantee coverage.’
Maintain your contacts.
Let’s go further on the last point. The people you know, work with, and who respect and trust you professionally are going to make your career. Do what you say you’re going to do. Meet deadlines. Finish what you start. Stay in touch with people you meet on press trips, at conferences, and through email. It will pay off!
Tip: At the beginning of each quarter, I reach out to the clients I have worked with the most over the past three months and a few I haven’t heard from in a while just to let them know that I appreciate their business and am always looking to get more involved. The return percentage on this is actually quite impressive – I generate at least one extra assignment from more than half of the reach outs and have on one occasion landed a better (and more profitable) contract.
Get enough sleep.
If there is one thing I absolutely have to have in order to do my best work, it’s sleep (and avoiding mid-week hangovers). This isn’t a mindless clock-in-clock-out-collect-paycheck type of job. If I can’t stay motivated I’ll end up taking a nap, won’t get anything done, and won’t make any money. Even with the freelance lifestyle, having a routine is key.
Tip: I segment my day into categories. Tougher or higher-paying work is done first thing, followed by a gym break or lunch meeting, and then tying up any loose ends or working on smaller projects. Any reach outs that need to happen get taken care of late in the afternoon, because it helps me end the day with some sort of hopeful intuition that I’ll find something good in my inbox the next morning.
Invest in your career. And, work your ass off to make things happen.
A year after I graduated college, I justified my restaurant job by telling myself that it takes a Master’s Degree to make it as a writer or journalist these days. I specifically remember saying that to a co-worker as I stood sweating in the kitchen, placing two pieces of bacon on top of a burger.
I knew this was a lie. The reason I worked in a kitchen was because I expected my English degree to easily land me a job with little to no effort on my part. When that didn’t happen, I resigned to excuses and a prolonged continuation of college-level partying. Two years later, I finally pulled it together after having an anxiety attack while pumping gas at 7-11.
It was time to get my shit together and do something with my degree. So I went on Craigslist. After several failed attempts, I landed a $50 per-week gig writing a music column for a local website. Alright, that’s something! That turned into me chasing down the publisher of a music magazine at an event I knew he’d be at, and drinking with him until I knew he’d remember me when I emailed him the following Monday. Six months and a couple dozen articles later and I had myself a job as an Associate Editor. Alright!
The point is, in the freelance world, nobody is going to give you anything. You have to scratch and claw for every dollar, every job, every byline. It’s never easy, but after a while, it becomes a routine. Stuff that may sound overplayed, like signing up for a writing course (and actually taking it seriously) and going to networking events often lead to opportunities you never knew existed.
Be flexible, and look at the bright side.
People love to complain. Freelancers are no different, myself included. Every now and then, I have to take a step back and remind myself how stoked I am to be working for myself, traveling on my own terms, and making my own schedule. This line of work has its headaches and is always going to be a roller coaster with peaks and valleys. I’ve learned to be open-minded about client feedback and have come to understand that different clients work differently.
Posting a snarky comment on social media when a contract is cut short, or a payment doesn’t come in before the end of the month, isn’t doing anything other than making me look unprofessional. Instead, I try to remember that there’s no boss looking over my shoulder telling me not to crack an afternoon beer to take the edge off.
Tip: There are going to be slow weeks. I try to fill the time by doing reach outs, generating lists of story ideas to pitch, and going snowboarding or camping. In order to stay afloat during these times, I opened a business savings account that does two things for me: 1. Holds money for taxes. 2. Holds money for slow periods.
The power of coming together is driving location independence
This sounds like an oxymoron. But what are the biggest factors that contribute to a successful entrepreneur or freelancer? It’s not locking themselves away in a home office.
For those who’ve left the time clock behind, the need to network and be amongst like minds is stronger than ever. Subscription member communities, co-working spaces, conferences, and even local happy hours are among the most popular methods for connecting location-independent entrepreneurs.
Sure, you can park behind a MacBook and land some clients without leaving the house. But to really grow, face-to-face contact is essential. This has resulted in a massive boom in mountain town coworking spaces and in small tech districts located far from Silicon Valley (like the one in Grand Junction where my coworking space, Alt Space, is located.
This morning I chatted with a guy I see regularly at the space about how the cost of membership more than pays itself back simply in being surrounded by others experiencing the same struggles, and being able to help each other out.
For more on my obsession with coworking spaces, read this February 2022 edition of Mountain Remote.
Remind yourself that it took a wide variety of skills to get to where you are
Many (I’d venture to say most) of us didn’t have remote work on a laptop as our top priority when we entered the workforce. Personally, I just never seemed to fit in in a typical work environment.
The road to location independence is a long and winding path that ultimately results from a desire to break away from the traditional concept of what a career is. Etching out a living independently requires a diverse collection of skills not learned in a cubicle.
A bit of business savvy, the ability to live on next to nothing, and a fine-tuned level of self-discipline are essentials. But you may just find yourself using the sweet-talking skills you picked up working as a restaurant server to put the closing touches on a new copywriting contract.
What skills have you picked up over the years that helped (or can help) you build a location independent lifestyle?
Mountain Remote news and further reading
Forbes broke down why feedback skills are so important in remote workplaces.
If the current banking crisis pushes us towards a recession, the effect on remote work could actually be positive, according to Psychology Today. Not that we’re rooting for a recession, though.
New Atlas broke down 111 resources, idea starters, and opportunities for people who can “work from anywhere.”
That’s all this week, see you next time!