One of my favorite television shows of all time is The Office.
If you’ve never seen it, it has all the fixings of the stock corporate workplace: drab decor, underwhelmed employees, bland work, and a cringey-yet-lovable manchild as a boss.
It was a show that spoke to those in cubicleland.
Part of what made people fall in love with The Office was not just its ability to portray touching moments in a mundane setting, but also its documentary-like film style that allowed characters to speak directly to the audience about their lives in this all-too-familiar setting.
In one of the recurring moments of the show, main character and effortlessly cool Jim Halpert helplessly glances at the camera during particularly painful, awkward, or ridiculous moments, as if to say, “Seriously, can you believe this?”
I didn’t know when I watched The Office as a high schooler that, in a few years, I would find myself feeling the same way as Jim did about the modern American workplace.
Before any of my former employers set virtual fire to my LinkedIn page, I want to be clear: in my first several years out of college, I had the opportunity to work for and with impressive organizations, including two nonprofits and a social enterprise.
Given that I started my career as an educator, I also didn’t have many of the average trials and tribulations of the average office bee. My job allowed me to move around, interact with people all the time, and be genuinely creative while sparking positive changes in the lives of others.
What more could I want?
Turns out, there was something I wanted that even my slightly atypical work environment couldn’t give me: freedom.
I found myself balking at specific arrival and departure times from work, regular and lengthy meetings, and high levels of control and oversight of my work. I started to feel constricted and frustrated that my time, energy, and salary had to completely submit to a higher authority… to The Man.
It bothered me, but it was the path I (like so many others) thought I had to take — just put my head down and work.
So I did.
After a while, the restrictions started to suffocate me. Confining elements of work I once reluctantly accepted became regular agitations, so much so that on Sunday nights my stomach would become a festering pit of apprehension and discontent.
After working at a few different places, I realized it wasn’t a particular company’s shortcomings (like I said, I worked for some great ones), but it was the traditional work structure in and of itself.
The whole notion of sitting at a desk, or just showing up at an office for eight (or more) hours straight, wasn’t going to be sustainable for an ornery, stubborn, contrarian soul like myself.
Eventually, I started looking for a way out.
While working as an ESL teacher in Santiago, Chile, I began freelancing on the side to have extra pesos for Happy Hour beers… erm… I mean… educational activities.
Guess where I landed?
A cool little place called Craft Your Content as a proofreader and copy editor.
In case you didn’t already know, CYC works with a lot of entrepreneurial folks, from Taylor Pearson, to Matt Paulson, to the folks at Empire Flippers and Eventbrite, to name but a few.
So, when I wasn’t at my full-time job, I read about business owners who had successfully grown side gigs into full-time, thriving businesses. In the pages of their stories, I found familiar frustrations and similar questioning of “how work should be.”
You mean other people feel this way, too? Even people much older than me? (I thought maybe I was just another millennial punk.) They left their jobs to run their own show? That can actually work?
Every time I got excited about the idea of entrepreneurship as my future, my annoying yet necessary roadblock of rationalism reared its left-brained head, whispering things like:
But even amidst these negative thoughts, I found other ones popping up, too — ones that reminded me of how hard I’m willing to work for something I want, how in the end it doesn’t really matter what other people think, and how I’ll regret it if I never try.
Through the conversations in my head, I started becoming more convinced that I could do this.
But even for a self-labeled control freak like myself, the idea of total freedom and self-reliance had drawbacks. After all, I did appreciate steady paychecks — with them came peace of mind that I would be able to feed myself regularly.
Logical and practical planner that I am, I formed a path that seemed low-risk and reasonable, to appease the rationalism and fears, but which would also allow me to start venturing toward entrepreneurship in the future.
The plan started to form:
“…Maybe I’ll start freelancing on the side to build up some clients and experience, and eventually transition to running a standalone business…”
“…Perhaps I’ll also start a blog to gain an audience whom I could develop into customers… “
“…After that, I could continuously grow my ‘side gigs’ into something more substantial that could one day become full-time… “
What if this could work… for me?
I decided to start with what I knew.
I reached out to the owner here at CYC, Elisa Doucette, to see what other potential work opportunities might be on the horizon, and if I might be able to be a part of them somehow.
As it so happened, she was looking for someone who could take on more of CYC’s operations and day-to-day management so that she could better focus her energies on growing the company and moving it forward.
In a few months, she said, there would be a Managing Editor position opening up — a full-time gig with virtual independent contractor status.
At the time, I wasn’t sure what that meant, but I soon learned that it would be the first and most important step in my entrepreneurial journey.
Essentially, I would have substantial and steady work so as to have an income with which I could count on feeding myself (important), but also the freedom to live and work wherever and whenever I chose.
I could manage my work the way I saw fit and also learn about running an online business through my methodology of choice: doing.
Oh, and I would also have enough free time to devote to my own projects and side gigs.
Was I dreaming?
The left brain continued poking, inquiring if wading into this completely new territory was such a good idea.
In January, I told it to shut up and took the plunge.
You may at this point be wondering what my tale of professional frustration and indecision has to do with you.
Well, as I am a few months into this curious journey, I have bumbled through my own slew of
mistakes learning opportunities and subsequent discoveries — knowledge that might help you along your freelance or entrepreneurial road, should you choose it.
That said, I’m not here to sell you on this lifestyle or convince you that I’ve somehow unlocked the mystical way to truly “live life to the fullest” while the rest of you dorks are wallowing away in an office somewhere.
I don’t subscribe to that holier-than-thou brand of self-employment.
All I know is what I have experienced as a fiercely independent yet anxious individual who has always wanted to do her own thing, and has finally found a way — her way — to do it, and has already learned a lot along the way.
If it turns out to be your thing, too, you’ll find your way. I don’t need to tell you how — lots of much more experienced people can, though.
Instead, I’ll hit you with four of the biggest cool and contradictory experiences and realizations I’ve had while professionally off-roading, and offer you some guidance to navigate similar bumps in your own journey.
Alarm clock sounds — my head pops off the pillow in a panic. Where am I supposed to be?
It’s late January, several days into my position as Managing Editor at CYC, but my neurotic brain hasn’t forgotten that the last four years have been governed by schedules set by others.
Prior to my starting this position, I taught classes all around the city of Santiago, Chile. This meant ripping myself out of bed early, showering hastily, scarfing down coffee and breakfast, and peeling off on my rattletrap bike, praying I wouldn’t be late.
Every morning brought stress, and every evening ushered in a slight touch of anxiety about the next day. I probably should have known by those emotions alone that I was working a job that wasn’t a good fit for me, but I continued on.
When I started my new position at CYC, something miraculous happened: the bad feelings went away.
Although I continued to have a full-time schedule, I also had the flexibility to arrange my working hours, rather than adhering to those set by someone else.
No running, no rushing, no commute.
I relaxed, knowing that I could simply open my laptop and “be at work.”
Once I no longer dreaded my alarm clock, mornings became enjoyable. I went to bed and woke up in accordance with my more natural sleep schedule, enjoyed my morning coffee, began doing morning yoga sequences, and taking some time for myself to write and reflect.
By the time I began working, I felt calm and alert, having taken some much-needed personal time before getting down to business.
I carved out a little space in my apartment designated for “work” and wore clothes that made me feel comfortable and relaxed.
I can work in my pajamas.
I can work in my bed.
I can work at two in the morning.
All good. Well… mostly, until I realized…
I’m working in my pajamas. (Where are my pants?)
I’m working in my bed. (Have I gotten out of bed?)
I’m working at 2 a.m. (Wait, where did the day go?)
Time becomes a much more relative concept, as does location and dress code.
As I adjusted to this different world, I quickly realized that if I didn’t create routines and rules for myself and my behavior, not only would I not be as productive as I wanted to be, but also I would feel like I never stopped working. And possibly wouldn’t ever put on pants or leave my house.
The quick and dirty way to combat this common work-from-home tendency is to make yourself morning and evening rituals (like my coffee and yoga), to get going or wind down every day. (More on this and other words for the wise down below.)
Also, make a pact with yourself to put on outside clothes. It might be tempting to work every day in your jammies, but going through the process of showering and wearing clothes you wouldn’t mind being seen on the street in can help you to psychologically connect to “being at work” when you’re working. Then, when the pajamas come along, your mind and body will know it’s time to relax.
A similar phenomenon can happen with the place you work. While beds are comfy, they should be largely used for sleep. Too much time working on your bed and you might find it hard to fall asleep. Set a strict no laptop or tablet in bed rule to help get yourself into the habit of leaving your work at the (bedroom) door.
Flexible dress code and work location are just a couple of the looser professional elements that self-employed people enjoy, but others can be a bit puzzling at first.
For example, most virtual entrepreneurial ‘gurus’ love talking about “working whenever you want.”
Yet, such extremely open time management felt both freeing and disorienting to me.
Initially, I wasn’t sure how to structure my time so as to work the most productively and efficiently without falling into the traps my inner procrastinator threatened to set. I had flashbacks to college all-nighters and past against-the-deadline work frenzies, and knew I would need some semblance of a structure in order to stay productive and sane.
So I decided to set up a schedule for my work from home that looked a little similar to that of an office (about eight hours, starting in the morning and finishing in the evening), but punctuating bursts of work with breaks.
At first, when I paused for a phone call or text, coffee break, or bread run throughout the day, I felt strange.
In the back of my head, a persistent thought pinged: “Shouldn’t you be working?”
I was working — but with some time adjustments and bio breaks so as to stay as creative and alert as possible. It became clear to me that I did not do my best work when I forced myself to sit and focus for four or more hours on end.
I need pauses throughout my work day for physical activity, conversation, mental diversion, and snacks. Lots of snacks.
As I took on more responsibility at CYC, I tweaked my schedule to best fit the work I would be doing from day to day. After all, unlike a more typical freelance writer or editor, I wasn’t cranking out individual projects that were assigned to me here and there.
My role as Managing Editor includes ongoing communication with not only our team members, but also with clients, writers, and other professionals we work with, as well as managing multiple editorial calendars and schedules — apart from other individual projects either assigned to or created by me.
All tasks are not created equal, and so there is no single work style that can be used to tackle them all.
To that end, I started to develop a sense of which times of day I felt most keen to write and edit, and which worked better for communication, management, and organizational work.
I found during mornings I could throw my creative energy into going full hermit and editing a manuscript or writing a lengthy blog post for hours at a time. In the afternoon, I often opted to talk, Slack, Skype, email, or otherwise manage others to ensure our agency systems ran smoothly.
Like a newly-minted superhero (à la Spiderman) becoming aware of their powers, with time I began to better understand how to balance my personal strengths and preferences with my role as both a full-time manager and free-bird contractor, to create a schedule that served both functions.
Obviously, things change depending on what’s happening here at the agency, but developing those understandings of both myself and the work at hand helped me craft a schedule that made sense for me and helped me do my best work at the best time.
I’d be lying to you if I said it wasn’t tricky; I have had a few more facepalm moments than I’ll readily admit.
Luckily, I have patient mentorship through my twice-weekly calls with Elisa, where I not only learn about the ins and outs of what it takes to run an online agency (spoiler alert: it’s a lot), but also find words from the wise that might seem obvious to veteran entrepreneurs, but puzzling to me.
If you aren’t sure how to manage your time, try keeping a log for a week of your work. At the end of the day, write out what you did, when you did it, and how well you did it based on your energy level, mood, creativity, etc. Be honest with yourself about times of day you derailed into Facebook or multitasked while texting.
Look for patterns in your behavior to identify places you could make adjustments to your schedule so that you can work better.
At this point, we’ve looked at how you can better set yourself up for virtual work success by setting personal ground rules and structures around your work, including your dress, environment, and schedule.
But forming a balanced life while self-employed has as much to do with what you do when you’re not at work as it does with when you are.
For this element, we should quickly touch on what types of people tend to flock to this highly independent lifestyle.
I’m gonna wager it’s a lot of Type A workaholics who really like control and honestly love working. You know, the kind of people who feel like when they aren’t working, they’re wasting their time. Maybe this sounds bonkers to you, but do you know anyone like that?
Well, that’s me.
While I initially envisioned my virtual work lifestyle as hyperproductive spurts of work followed by lavish relaxation — something else happened.
I started to get even more addicted to working. With my atypical schedule, I found I had enough energy in my spare time to take on personal projects and other opportunities that caught my eye. The time I would have been rushing around in the morning or commuting to work became newfound valuable moments that could be used more productively.
What could go wrong?
Well, instead of investing my spare time in activities that would help me recharge, engage socially, or otherwise just chill out, I took to projects that would support my career aspirations.
My hobbies became other entrepreneurial pursuits, like blogging and personal development — meaning more hours of “working” in front of a computer screen.
Now, at its core, being interested in developing side hustles and the like is not detrimental. Meaningful and creative work brings many people a lot of joy.
But if you try to productively use every minute of your every day, guess where you’re headed.
Here’s the thing, fellow aspiring Leslie Knopes of the world: you can’t do everything, all the time, always. You might think you can, but even with a thriving coffee addiction, there is only so much you can do in a day.
Until you finally do create that self-sustaining business where you can throw up your middle finger and answer to no one, as a freelancer, independent contractor, or full-time virtual employee, you cannot confuse a flexible schedule with the notion that you have all the time in the world (and that it should only be used for working).
Yes, you need to dedicate the largest chunk of your time to delivering the work for your client(s), period.
But once that has been set, determine how many of your remaining hours you would like to spend on personal projects or other side gigs, personal care, social and family interaction, and the like.
We all wish that there were more than 24 hours in the day, I know. Be honest and kind to yourself, accepting that there is only so much you can do in one day, so just do your best.
Although I am a self-diagnosed workaholic, who genuinely enjoys doing work and being as productive as possible, even I know that extreme workaholism is unsustainable, and will ultimately negatively affect you, not to mention the quality of work you produce.
Even though sometimes I would much rather spend my free time brainstorming new ideas, reading a book about creativity, or writing a bangin’ blog post, I also know how important it is to spend time doing things that don’t seem obviously productive, both for yourself and for those around you.
You never know when that party you reluctantly attend, coffee date you set, or stroll you take through the park will inspire something within you that you wouldn’t have stumbled across on your own.
If you’re the kind of person who could see themselves getting addicted to work to an unhealthy degree (not eating/eating too much, regularly foregoing sleep, exercise, or social interaction, constant notification checking, etc.), it is a serious factor to consider before you opt for this lifestyle.
Plan ahead to get a complete sense of how you might balance “play” with work. Set yourself some seemingly odd but necessary goals to make sure you’re making time for yourself outside of work a priority.
Before I started my position at CYC, I wrote out some ideas to encourage myself to better balance my time, and take care of myself:
You might use similar guidelines or come up with your own, but make sure you have several up your sleeve to ensure you don’t become a work robot.
Apart from enjoying your unique freedoms wisely, setting a form-follows-function schedule, and finding balance between work and play, the independent work life also hits you with weird and admittedly small but also “WTF” inconveniences.
Think of things that you would not have had to deal with if you were to have a traditional job at an office.
Disclaimer: these are not what I’d refer to as full-fledged problems worth whining about. But if you are potentially interested in signing on for this lifestyle, they are things you should take into account.
If you do indeed take the route of truly working from home, you’ll discover something quickly: distractions are everywhere.
And I’m not just talking about the bed that whispers to you on your groggiest of days to come on over and take a little power nap (Psst! You deserve it!).
Or the dishes that moan from the sink, yearning to be washed.
Or the to-do list of errands staring at you from the fridge.
I’m talking about the weird pop-up stuff that you never knew might be an issue and that you now have to deal with since you’re, well, at home. Like:
Some of these annoyances admittedly might be more common or typical of city dwellers like myself, but Murphy’s Law says that some way, somehow, they’ll happen to you, too.
Plus, tons of other potential snafus I haven’t come across yet. (Universe, this is not a challenge.)
Unless you’re the kind of person who just really, really loves being at home, you’ll eventually get sick of staring at the walls of your house and want to venture into the wild world outside.
So, you’ll probably go to Starbucks or some equivalent café to get your daily cup of joe and settle in for some work.
Except it doesn’t always pan out that way.
What follows are some thoughts I have had while trying to get work done at a café:
Of course, cafés are not the only place you can set up shop. Any place with wifi will work. Depending on the amenities in your local area, you might consider getting a membership at a coworking space (dependable wifi and human interaction) or heading over to the library.
Or, you entrepreneurial lil’ soul you, you might consider starting your own pop-up coworking space.
Wherever you end up working, try to follow the Boy Scouts’ advice and be prepared.
Have backup offline work in case the internet fails. Charge your computer before leaving the house. Pack a lunch. You get the idea.
So, is the whole new world of working for yourself all that it’s cracked up to be?
For me? Honestly, yes.
It comes with its own weird characteristics and flaws, bonuses, and frustrations for sure — many of which I’m sure I’ve missed, haven’t experienced yet, or don’t apply to me. (I live abroad, I don’t have children, I don’t travel constantly, etc.)
That said, I hope at the very least I’ve given you a realistic glimpse of what the world of self-employed / freelance / entrepreneurial / creative work is like, from my perspective. I’m a new, but honest, poster child for what this lifestyle can be — if you choose.
Of course, it can also look very different. It’s your life, man.
Ultimately, although I find this work-lifestyle much more in tune with my personality, I also recognize that it’s not for everyone and actually takes a fair bit of fine-tuning to really turn it into the right fit.
In the interest of keeping you as a happy and healthy self-employed individual, I will touch back what we’ve covered and offer a few suggestions before we go about the most common challenges of the independent lifestyle:
Getting into the Biz: Start small. If you can’t make the leap to self-employment right away, do so in steps, starting with freelancing and building up until you can do it full-time. Side hustles or freelancing gigs can grow into unexpected opportunities.
Managing Your Time: Create a schedule for work time and playtime. Stick to it. Try out the Pomodoro technique, which emphasizes short bursts of activity followed by quick breaks.
Making Routines: Try to do the same thing every morning and evening, to give yourself some stability. Here’s mine:
Being Social: Set boundaries with friends and loved ones. Explain to them the importance of working during your work time and that working from home does not mean you are free all the time. On your end, make sure you’re not ditching your pals too frequently because you’re always “working overtime,” and make sure to be social sometimes, even when you’d rather be working.
Working With Others: Find a community; do not become a weirdo shut-in. (Looking at you, introverts.) Connect with others; it’s good for you. Consider getting a membership to a co-working space or becoming a dedicated patron of your local library.
Creating Space: Be cognizant of your notifications, and learn to prioritize their urgency. Turn most if not all of them off on your phone, so you have to manually update and can disconnect from work when you choose. Every day should have time set aside where you are 100% not at work.
No matter what you do, do not expect this lifestyle to magic wand away all your problems, making you loads happier, or otherwise radically altering your life in a positive direction.
Ultimately, if you are not happy and satisfied with yourself and your life internally, no amount of workplace or environment shift-ups are going to change that. (A good therapist can help with that, though.)
You may find that it actually isn’t what you thought you wanted.
You may find it is exactly what you wanted.
You may find that the self-employed life is one you’ll live for a while, but that you might eventually wind your way back to the cozy nest of traditional employment.
You may vow to be a work maverick forever.
Today might be the last day you go to work at an office. Don’t say I didn’t warn you.
Photo credit: AnnaTamila
Gina Edwards is an unapologetically snarky blogger with a love of parentheses (but who isn't?) and beer with funny names. She's currently be-bopping around Santiago, Chile on her bike, teaching her native language to fancy people. Her skills include making hilarious puns, no-bake cookies, and mountains out of molehills.