Confessions of a (kinda) lonely freelancer

Balancing freedom and structure in a disconnected world

Lately, I’ve been spending a lot of time thinking about work.

Many are flocking to remote gigs and freelancing. There’s a strong allure of “being your own boss”. Yet burnout is on the rise, there’s an epidemic of loneliness, and workers across the globe seem to have less freedom than ever before. Our current way of working seems to be broken.

We aren’t exactly thriving — and I know I’m not alone in feeling this way.

Is the answer sending us all back to the office? Or do we need to take time to reconsider our relationship with work?

I do my best work when I’m consumed by it; when I have the time and freedom to briefly obsess over what I’m working on.

I thrive on hyper-focusing, diving deep into topics. It’s fun, engaging, and oh-so-exciting.

But at the same time, I don’t think my brain works how society expects it to. I can’t seem to force myself neatly into any one box. I feel weird calling myself an entrepreneur, but I’m pretty sure I’m not cut out for a 9–5. I work in strange ways, but if not for comparison with others, I wouldn’t see anything wrong with my quirks.

Some of my best work comes from brief, intense engagements with it. And this doesn’t always have to mean I’m racing against the clock, fighting to finish an assignment fueled by adrenaline and a ticking clock.

But the more I force myself towards the “normal” structured baseline, the harder it is to find my flow state.

Take my blog posts, for instance. The ones that get published happen in one inspired attempt.

Similarly, in school, I remember having to submit a rough draft for an assignment. I’d hyperfocus, finish the entire paper, and then reverse engineer a ‘rough draft’ with just enough minor spelling errors in order to fit the expected timeline.

This pattern of work seems to follow me in life, from school to the workplace. But is it really such a horrible thing?

Back when I was selling wristbands in high school, I had what felt like the perfect structure. School filled my days with intellectual stimulation, but I was done by 2pm most days, then it was side hustle mode.

I loved setting up online sales posts on Friday nights, packing orders by hand. It wasn’t all work with no play, though. In addition to earning money, I had time to date, make friends, and join clubs. My life felt busier than ever before, yet extremely balanced and fulfilling. Meaningful, even.

I had plenty of responsibilities, commitments, and stress, of course — but my free time was all mine.

I could aggressively hustle and make $1,500 in sales one weekend, but then go ahead and practically close up shop come finals week. I chose when and where I wanted to work, and all I had to worry about was making my customers happy.

I was my own boss (and not in the MLM #girlboss kind of way).

I kept up with this semi-successful business all throughout high school and college, and I reached six figures in total profit without sacrificing my GPA. It was so much fun, and I learned more than my classes in school could have ever taught me.

But soon after graduation, sales slowed, and I started looking for something more meaningful.

Plus, now that I was out of school, I needed to get out of the house and start interacting with other humans again.

I couldn’t really see myself working at some random cafe post-grad, so I quickly decided to start looking for “real” jobs. I had already convinced myself it would be alright to work in an office, even if just for the social aspect.

I played around with the side hustle thing, but now it was time to join the real working world. That’s what society, and my friends, and my old professors said. I accepted my fate.

The job market, however, had other plans.

I finished my four-year degree right in time for COVID-19 to usher us into a world of remote work.

A once-promising job offer at my alma mater vanished out of COVID-caution, like many others, and it seemed every other “real job” I had in mind was heading toward remote work anyway.

I considered going back to school and starting a master’s program, but Zoom University didn’t seem that appealing at full sticker price.

Freelancing began to look attractive, promising flexibility, freedom, and autonomy.

I spoke to a few friends who had tried freelancing and other forms of remote work, and they seemed to be making a decent living with flexible hours.

I’d already made money on the internet before, but selling services was a lot more flexible than selling physical goods.

Scrolling through YouTube led me to the life of digital nomads, that traveled the world, lived on the road, and worked flexible jobs from practically anywhere.

I envisioned myself as a digital nomad, coconut in one hand, laptop in the other, surrounded by palm trees. Or something like that.

So, I did the thing, embraced the hustle, bought a website domain, formed an LLC, and started working as a freelance marketer and content writer.

I had the freedom to choose my clients and my working hours — and even my rates. I loved my clients and enjoyed the work — and I still do! I had a chance to create while helping people — and getting paid for it.

I saved money by working out of my parent’s basement, loosely inspired by the FIRE movement.

But I felt stuck, and often uninspired. I’d occasionally venture out to a local coffee shop, and sometimes, the gym — but that was it. Four years post-graduation, I kept up with my new way of work — and I couldn’t see myself going back and working in an office.

Over time, the harsh social distancing restrictions started to let up.

Yet, I still found myself tethered to my basement desk, traveling less.

I stayed isolated, beating myself up for not hitting the overly-aspirational goals I had all day — week — month to work on.

While others with traditional 9–5 jobs could unplug on vacations, I brought work along with me, perpetuating a cycle of guilt and unfulfillment, never truly free. Oops.

I realized that I simply could’ve worked regularly during the week and enjoyed my weekends offline, communicating my availability to clients.

Instead, I self-imposed stricter limits than any boss, leading to a blend of work and life into a continuous, unproductive dread.

But still, I couldn’t really complain. Right? My friends and family worked much harder jobs with much less freedom.

I could literally work from anywhere — wasn’t I already living the dream?

After weeks and months of bleak, blegh days passing me by, I started to see the need to disconnect from overstimulated-anxious-work-mode — at least occasionally.

I had the illusion of flexibility. But it meant nothing if I didn’t know how to use it.

I turned down conferences, travel, and networking opportunities in favor of hunkering down at home.

Whatever free time I had seemed useless as it didn’t sync up with the free time or vacation schedules of the loved ones around me.

What good is “flexibility” if looming deadlines make me feel like I don’t have time for the gym? Or if poorly timed client calls rob me of small pleasures like stopping by my grandma’s house for lunch?

I know, I know — the grass is always greener on the other side.

But I can’t help but think this isn’t the right way for me to be working. And maybe it’s because of societal pressure and shifting norms.

Or maybe, it’s all my fault.

Either way, it’s my responsibility to make a change when it comes to my own work-life balance.

While freelancing, I could do anything, yet I felt paralyzed by choices and deadlines and every “client crisis” or last-minute request.

I realized that optimizing my life for more free time and less responsibility wasn’t the best solution, because the lack of structure left me in constant chaos.

There’s a delicate balance required of structure and freedom, especially when it comes to the separation of life and work that must exist.

Being in a structured environment like school sets you up to work best in an equally structured world. But not everyone wants their lives to have the rigid structure of an assembly line.

Sure, on paper, my educational journey might seem impressive; I started college when I was 14, graduating with my four-year degree before even finishing high school. Looking from the outside in, you might even think the structure helped me excel. But I’d disagree. I found I worked best when going against the grain, testing out experimental programs like dual enrollment to find the right amount of difficulty and flexibility to learn and grow.

I’m not sure that the intended structure of school ever fit the way I work and learn — and that’s okay. I’m the only one that’s going to be able to advocate for what I need. I can’t expect colleges to mold their one-size-fits-all approach to my whims and unique interests.

So, how can I stay true to my natural inclinations and way of working while staying motivated?

I’ve tried a few different things, but nothing has completely solved my problem yet. Even as I add responsibilities to my plate, like going back to grad school this year, I don’t really feel all that fulfilled. I don’t even have a proper work-life balance in school, even if it’s my only commitment.

I’m still lonely.
I don’t leave the house enough.
I use my phone too much.
I’m not a perfect human, and I don’t make it to the gym every day.
I still feel like I don’t have time for anything.
There’s a low level of anxiety weighing on me constantly, and I never feel productive enough.
I know, I could be doing more.

I have been trying so hard to emulate that after-school-side-hustle feeling in another way, thinking that if I had enough free time, I could figure out my perfect flow again.

But then I worry about having too much free time. Being unproductive if maybe one Monday I end up chilling in a coffee shop instead of working in an office and “paying my dues” like my peers.

I don’t want to be lazy.

But what’s the point in pushing so hard when there’s nothing to look forward to after completing the next task? When I still feel lonely after the work is done?

This time around, I just feel bogged down by school work instead of work-work. And maybe it’s just a me problem — a me-needing-to-find-meaning problem. But I hope there’s a solution out there somewhere. Because I cannot imagine many more years of this lonely hamster wheel of fluctuating motivation and a constantly moving goalpost — working for what exactly?

It doesn’t help that the world feels so disconnected.

I’m a hard worker when I need to be. But I also crave new experiences, and travel, and social interaction with friends, family, and even strangers.

Deep down, I know that toggling from my home office to a local coffee shop isn’t enough of a change in scenery to refuel my heart. But not even going back to school did it for me. I spend my days in the same classroom with the same people and I don’t know if I’ve ever felt more alone.

I sit in my apartment knowing the assignments that need to get done but when I think of what future career I will use it in, I worry that the future career will have the same lonely, disconnected heaviness to it. What’s the point? Where’s the meaning? I need inspiration. I need connection. I need more.

This is where I wonder if maybe it is a problem with society as a whole.

I have a good feeling I could map out my own version of a productive life and schedule, and it’s something I’m trying to do now, but I also can’t do it alone.

Maybe I need to find others whose brains are wired like mine. And maybe putting out a post like this into the world will help me find my tribe.

If I had to choose my ideal work mode, it would resemble my ecommerce hustle — structured yet flexible, with the ability to work in short bursts when motivation — or inspiration — strikes.

I recently read a tweet about high performers posted on X by Laura Wendel, a startup founder and software engineer. It made me realize that maybe I shouldn’t be so hard on myself about the way I work best.

This tweet on X speaks to the strange working quirks of high performers, and it sparked something in me; maybe I shouldn’t fight too hard against my natural inclinations.

I think that if my life was designed more like one of those limited-edition-product-drops (and less like a typical 40-hour work week structure), I’d do okay.

Having my productivity directly correlated with output and earnings feels great to me, and having the ability to step away from my work for days at a time without losing progress or falling disastrously behind is a nice plus.

Maybe some of my beliefs are rooted in how my family used to make a living — with seasonal ebbs and flows.

Growing up, my grandparents ran a landscaping business and a Christmas tree farm. There was no such thing as steady work.

Money made from landscaping in warmer weather had to last them through winter, up until Christmas — which came with another spurt of work to be done. Then, the money from Christmas tree sales had to last them throughout cold Ohio winters, with not much of a market for landscaping in the snow. And the following year, the cycle repeated.

Work was never steady. It couldn’t be. It was work hard, all hands on deck for a period of time, then stop, rest, and recover, before preparing to do it all over again.

Interestingly, this pattern mirrors what I’ve seen in the entertainment industry as well.

As a movie extra and stand-in, I’ve observed rush and thrill of a movie filming in town, with exhausting 12–15 hour days on set, and weeks with little sleep from the production team, followed by periods of quiet, and a long wait for the finished film.

A recurring theme seems to be that a proper log-off is needed sometimes, especially after such intense bursts of work and focus.

It’s a world of extremes, but much like a Christmas tree farm, it’s also kinda magical.

So at least I know I’m not completely crazy for being drawn to non-traditional work. Maybe I’m not alone, and maybe I’m not wrong, either.

I need to be the one in charge of making sure I’m working in a way that’s right for me. I also need to make time to rest, even if it means putting it in my schedule — especially after particularly long or stressful projects.

I know that with enough effort, I can structure a routine that allows for — and maybe even encourages — that sweet, sweet flow state. A distraction-free time for thinking and creativity.

Working in a different way doesn’t mean getting rid of all structure, though. That’s just chaos.

There’s a special kind of excitement in preparing to have free time without accounting for every spare minute. Like booking a vacation that isn’t filled with activities from sundown to sunset. To allow time to explore without expectations. To worry a little less about feeling productive. To allow time to get swept up into the special moments as they arrive on the spur of the moment. To not tune out the ebbs and flows of life for the sake of a routine.

What is productivity, anyway? What does success mean? And to whom? Is it worth denying your nature to chase structure and stability? Will I ever reach the ever-moving goalpost of success, to be accepted and loved and deemed worthy and productive?

As I embrace the new year ahead of me, I’m ready to make some changes to the way I structure my days.

I’m ready to let go of guilt and expectations. To finally embrace the way I work without trying to fit myself into a box that’s not made for me. One that doesn’t work how I do and that most likely never will.

Cheers to making more time for the unexpected,

-Adrianna