Behind the Glamour - Top 5 Challenges of Remote Freelance Work

Oooh yay, pretty coffee shops and working in my pajamas, phone calls in bed, yoga classes in the middle of the day because I can, slow mornings and busy afternoons one day but the opposite the next day, I get to decide… Freelance remote working is pure, bliss.

Quietly looks around for validation…

It’s bliss, right??

It’s the dream that I’ve had for about the past two years. Location independence. Freedom from a brick and mortar job. The ability to work from wherever, whenever I want. Being my own boss. I wanted this because I was struggling to find the free time to fill my days with meaningful, fulfilling activities besides my job, while still maintaining my mental health. I figured remote work would give me an income stream while allowing me to choose where I wanted to live and how I wanted to spend my days, whether that meant part-time on the boats or simply no boats at all.

I wanted to wake up and have complete freedom to determine the schedule of my day. I didn’t want to force myself to exercise first thing in the morning just because that was the only time that made sense for my workflow. I wanted to have a slow morning with coffee and tea and lemon water and journaling and meditation, and move on to work when I was ready. I wanted to say yes to invitations from friends to visit their nooks around the world because life is short and so is time. I didn’t want to have to plan my trips around meager “vacation days.” I wanted to be able to go home for an extended period of time to hang with my parents, enjoy their company, and actually get to know them as individuals and develop our adult relationship, while still making money. They’re getting older. I am too.

My family and me

And I want to make memories. This remote work life is not an uncommon dream. Nor is it an unobtainable dream. But as dreams start to come to fruition, there’s that ego, that human nature, that is quietly whispering in your ear…is this it? You got what you wanted…why aren’t you happy?

I have always been terrified of working just to work. I know plenty of people do it, and having a job is a blessing, a gift, something to cherish. But too often, we sacrifice our own dreams and happiness without trusting the “flow” of everything to lead us to where we need to be.

I always want to find fulfillment in my work, and when it comes to working remotely, it takes time to find meaningful projects that will still pay the bills. I’ve been pretty busy working full-on seasonal jobs the last several years, so my dream of remote online work has always taken a spot on the back burner. It would spark back to life on the weekends, when I would spend way too much time scrolling through Upwork freelance job postings and trying desperately to get traffic to my blog.

So I made the decision to take a season off and spend the holidays with my family. I realized that spending a winter in Idaho hanging out with my family could be relaxing and good for self-care but would also provide me with some headspace and (ideally) clarity to explore remote work a little bit further. I was presented with the perfect opportunity to dive a little bit deeper into this dream of mine.

And it is definitely slow going at first. I’ve brainstormed and applied and networked and researched and scrolled, scrolled, scrolled. I’m also learning some lessons along the way, and I wanted to share the challenges I’m facing, because I know I can’t be alone in all of this.

the challenges - what no one tells you about remote work

1) You have to pull motivation out of freakin’ nowhere

When you’re daydreaming about remote work, all you think about is what you’ll do with the free time you’ll have, how many cute coffee shops you’ll get to work from, how great it will be to cuddle with your cat while you work from home.

Well, shit, friends, nobody told me how hard it would be to pull yourself out of bed, get dressed, and get to work. I’d find myself lolly-gagging around until oh crap, it’s 9:30 a.m., I’m still in my pajamas eating breakfast and watching my cat sleeping…guess that means no money for me today…

So you have to come up with your own motivation, and sometimes you just have to really, really fake it. Remote freelance work can be a reality, but you need to be your own biggest cheerleader.

2) The income is very inconsistent

Every book or blog that I’ve read about freelancing and remote work has warned me about inconsistent income, so I should’ve been ready. But it becomes even more frustrating when you’re actually trying to live with that nonexistent paycheck. I’ve been fortunate to stay with family and friends while I’ve been “starting out,” which has made it a bit easier financially, but I keep thinking, whoa, if I was living in Maui right now doing this, my finances would NOT BE WORKING. Like, they’d be broken.

So I’ve had to revamp my thought process, look for ways to diversify my income, and realize that all the time I spend networking will hopefully pay off in the future. I’m teaching English online now, writing articles for local magazines, designing websites for a few clients, juggling my blog, and…my paychecks are TINY.

I hope I can look back on this post in the future and giggle fondly at my newbie freelancer self…

3) You get frickin’ lonely

I’ve always loved being by myself, but at the same time, I’ve often felt extremely lonely at the same time. I can’t explain this trait about myself, and I know that I am an introvert. But there’s something about sitting alone in the house or apartment, typing away, thinking about all the people having coffee at work or making jokes with colleagues in office buildings down the street, that makes me a little wistful. Remote freelance work doesn’t provide that same camaraderie.

Grass is always greener, eh?

I’ve been balancing it by trying to make phone calls to friends and family, and unfortunately, by spending more time on social media. To buck that habit I’ve been trying the time management Pomodoro technique, and I’m hoping that will encourage me to stay off the apps.

4) Time management is a mega struggle

When you’re charging by the hour and not getting that pretty salary dropped right into your bank account, every minute counts in remote freelance work. Can you justify spending 20 minutes getting ready/walking to your favorite coffee shop when you could spend that 20 minutes at home at your desk, finishing up that next blog post?

I’m figuring out what does and doesn’t work for me, and I know I am more productive in coffee shops. I love the vibes and the energy from the people around me that are also working, chatting, meeting up, and that makes me light up a little bit and motivate me to crank my stuff out.

When I’m at home, I realize that you can’t just stop every five minutes and make tea, pet the cat, check your emails, because stuff won’t get done. Come on Pomodoro technique!

5) Applying for jobs takes more time than the jobs themselves

I’m imagining that lining up freelance jobs becomes a bit easier as your network gets bigger, you deliver more quality work, you make the right connections. I’d love to get to a place where magazines are reaching out and begging me to write the next piece for them! But instead, I’ve been spending hours sending out pitches for one article that’s going to earn me $65…whoa. Watch out bank account, you literally won’t know what hit you…

Starting out is hard in the remote freelance work world. I get that. It’s just hard to maintain positivity and know how to spend your time most productively.

so how do I stay upbeat and remain hopeful?

FAKE IT TIL YOU MAKE IT. That’s been my motto for a little bit now, and I’m hoping it rings true. Just keep going, know that the beginning of anything is temporary, and let your energy and your work speak for itself.

I also spend a lot of time pumping myself up with dancing, yoga classes, runs, working out, good coffee, and quality conversations. Journaling has become more crucial for me now than ever before.

So even as some jobs start trickling in and remote work is becoming a tiny bit more tangible…it is not a fairytale, yet. But I will keep manifesting the future I want, and pretend it already exists, and then keep living like everything is just as it should be. Because it is.

Tell me about your remote work struggles! I’d love to hear more about the challenges, or your victories, or words of encouragement. We’re here to lift each other up!

XX,

Lolly

Nice wrinkly shirt, Lolz…

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