Maybe it's the millennial in me, or because I live in a city where just about everyone I know and associate with is "self-employed", but I genuinely believe the traditional 9-5 grind is on its way to becoming a thing of the past.

Welcome to 2019, a booming, technology-driven, transitional period in time where the generations before us are employed at the same company they've been with for the last 20 years, waiting on their hard-earned pension. While the younger generations find themselves making money in their sleep with social media and Google Adsense; leveraging the internet to sell their art/services/resources; virtually employed by companies on the other side of the globe. 

It's flipping mind-blowing.

Yet, there's still this connotation of people who freelance being a "starving artist,” who never make real money or forever search for a paycheck? Hmmm? Well, tell that to my influencer friend who made half million last year, Baby Boomers. Times have ch-ch-changed!

But there’s also this tricky "startup" phase freelancers go through where we can't seem to nail all the self-employed logistics. Yes, things like landing a steady paycheck, finding your own healthcare, or figuring out your God-forsaken taxes are, without question, essential to keep the IRS from pounding on your door. But on top of that boring crap, there's a logistic side of freelancing that — to be frank — you should nail before anything else, and that is figuring out your "why," "what," "how," etc.

It didn't occur to me when I was 18-years-old declaring my Journalism major, that the traditional writing career path would probably require extensive periods of sitting in a desk. At 22, I gave that lifestyle two big middle fingers, began traveling the world, writing, pitching, snapping, editing, finding every sort of loophole to avoid a desk job (read: electric chair) at all costs.

I promised myself that I'd drive for Uber, work abroad, wait tables, sell my eggs, or clean houses before I sat my ass in a desk for eight hours per day working on someone else's goals/dreams.

It took a while, and my "startup" phase was frantic, confusing, and flat out exhausting to a point where I actually told myself, "Maybe this just isn't in the cards for me." But after writing for exposure, writing for pennies, writing for assholes, and writing for impossible deadlines just to prove myself; I can finally say I've built myself to a point where my freelance career is developing at overwhelming speeds where I'm not only having to turn potential clients down due to massive projects already on my plate but, wait for it…I no longer consider selling my eggs for cash! What a relief, right?!

I'm joking (kind of)…

So here's the in's and out's of how I managed to work to live passionately and fully, and not live for soul-sucking, tireless work. NOTE: Every individual is different, and what you are about to read is strictly based on my own experience unique to a freelance writer. I don't have ALL the answers. But I do know what worked for me. So here we go…

Talk to yourself

Who the hell are you? What are your passions? What are you good at? What makes you stand out from the competition? What do you enjoy building/creating/doing? Is your craft marketable or even needed? Are you ready to dust your hats off to be your own bookkeeper, project manager, salesperson, accountant? Do you have the self-discipline? Are you willing to sacrifice things you didn't think you'd have to sacrifice for this lifestyle? Are you just romanticizing the idea of freelancing? Or do you believe that you have what it takes?

If you don't know the answers to these questions, you'll have a hard time convincing someone to hire you. If by some stroke of luck you are hired, you'll probably struggle with producing the work asked of you if you don't enjoy it, or you don't know what you're doing. Trust me when I say, freelancing will introduce you to a level of yourself that you haven't met before. It's a wild ride, and it starts with a long conversation with yourself before anything else. 

My own internal conversation (or my "why") was an overwhelming desire for a higher quality of life and ache to write things I was passionate about. Maybe it's the traveler in me, but the thought of going into the same building, sitting at the same desk, and working with the same people, doing the same assignments every single day was suicidal to me. I didn't even care if that meant I'd be financially comfortable or "respected" within societal norms. What's money in the bank if you're spending your precious days under fluorescent lights, having monotonous water cooler chats, and staring at a computer screen for eight hours a day? If that’s “societal acceptance” or “living” or “just how it goes” well, I want no part in it.

Pay attention

When I first started as a freelance writer, my "niche" was travel. At the time, I was hopping from country to country writing for travel magazines, hotels, and tourism boards of the like. Despite travel being a trillion dollar industry, it wasn't creating a sustainable income for me. But I felt the need to stay with it because I was (and still am!) so passionate about travel, I was constantly on the go, and I had some damn good stories to tell (mugged in Mongolia, cat-fished in Hong Kong, nearly kicked out of Spain, etc.).

Visiting some of the most pristine and pure places in the world made me want to, desperately, do better for it. Experiencing how my body and mind reacted to vastly different environments, foods, cultures and what I feed both of these things with, made me second guess everything. And after living in a blanket of pollution in places like Hong Kong and Seoul, to witnessing the stunning beaches of Bali, Sri Lanka, the Caribbean, and Hawaii covered in waste and plastic — my niche began to transition from travel to health/wellness and sustainability. 

Looking back, it's almost comical that I didn't notice how my days on the road were centered around doing healthy activities (yoga, hiking, swimming, surfing) in foreign places, rather than the foreign places themselves. Or that my knowledge of wellness and nutrition (I have a small background in healthcare) was keeping me from collapsing on long, heavy travel days. Or that I was digesting more "health/yoga related" content and information during my free time than I was "travel-related".

Shit, I could go on and on about the ways I was subconsciously ignoring the signs of where I should have focused my attention. My money-making, happiness-creating niche was there — I was just too caught up in working towards something that wasn't meant to be to notice. 

When I found myself starting my next chapter in LA, the mecca of health, wellness, and yoga — everything fell into place. High paying jobs, projects, opportunities knocked on my door that were so far from my original travel niche, I found it crazy that I had even landed them.

I meet a lot of freelancers who struggle with finding their niche at the start. They know they love photography and can take stunning portrait shots, but their passion lies in shooting landscape. Or they get paid to model or act, but they'd rather be behind the camera (and vice versa). But I can't stress enough how important it is to pay attention to where your energy and focus gravitates towards. It makes a world of difference in your paycheck, your day-to-day, and your future. Be okay with the uncertainty, be willing to let go, be open to the shift, and watch things come to life for you. 

Sell yourself

And maybe your soul too? Kidding. The point of freelancing is to create soul-fulfilling work (hopefully from the comfort of your couch) and to do that…well, you need to know how to market yourself.

I'm not going to tell you that a resume isn't essential to have. But I will say this very website is the reason I get hired as it professionally lays out and defines my services, skills, writing abilities, past and current projects and clients, who I am, what I can do, etc.

But it doesn't stop with a website! Any creative will tell you that your creativity should begin and end with people. Reach out to your old contacts, university classmates, the girl/guy next to you also on her laptop at that busy cafe, your mom's friends, your friend's moms, your ex-boyfriend's new girlfriend who's IG page your stalking (kidding, don't do that). People have similar interests as you! They might buy what you're offering, or know someone who knows someone, who needs what you do and your skillset.

LinkedIn, your social media channels, sites like Craigslist and Upwork all play a massive role too, and are all a no-brainer to figure out for the average millennial. So spend time in sharpening and defining your skills on the appropriate platforms for whoever might be looking. And for the love of GOD, don't post pictures of your butt on social media, or spill your life story out on your captions/portfolio, or lie on your online resume. It will catch up with you! Keep it classy. 

Do your "adulting"

Alright, let's have (a brief) money, tax, insurance talk.

Think of your freelancing career as your own business. Starting a business requires money (spending and earning), tax payments, and relevant healthcare for your employees (i.e., YOU!). All that "adult" stuff, so to speak..

I highly recommend evaluating your current funds before pulling the ripcord on whatever current steady paying job you have. Starting up will require having some cash in the bank to fall back on, as well as start-up cash. Expect a well-done portfolio/website, and maybe whatever software programs your services require, to have monthly dues. You should invest in business cards, an Upwork subscription, new supplies/tools you'll need, etc.

Consider your bills, loans, lifestyle, and how much you'll be making or want to make. Then cut what you're making by about 30-40% for taxes (this one is important to keep the feds at bay). Are you breaking even? Trust me, that's not a place you want to be. Does that number leave you satisfied, or allow you to live comfortably?

The good news is you can write all your freelancing expenses (website dues, coffee meetings, airfare fees, software program fees, etc.) off on your taxes. The IRS deducts those expenses from the amount you owe quarterly (how I file), or yearly. It's all a matter of holding onto your receipts, dumping 'em onto your friends who work in accounting (love you guys!), and having them help you with all that scary tax stuff. If you're earning the big bucks, I'd strongly recommend filing an LLC (S-Corp) to back your butt up with all of this.

Unless you get your healthcare through a partner, parent or what have you, you'll need some independent health insurance. If you live in California as I do, there are dozens of companies that offer full coverage at standard to low rates depending on what you opt in for via Covered California. Keep in mind, if you're a freelancer without health insurance, odds of you getting penalized for it on your taxes are high so back your butt up with some health insurance too, friends! It's a good thing to have.

Work your ass off

Despite what those Baby Boomers think, or what the average millennial is posting on social media (floating breakfast platters in pools in Bali), freelancing is HARD. Like 60+ hours a week hard. Roughly 20 of those hours are spent sending pitches out for new/more work, or emailing past clients saying, "Hey, give me my money already!" It's ass-kicking, and I genuinely have never worked this hard in my life.

I mean sure, you can work from home still in your PJs at 1 pm on a Tuesday, but there's a lot more to it than that. You are basically "on" and "working" around the clock. For me, the notifications start going off for me at 6 am (I have a few clients based on the east coast), and they don't stop until about 11 pm (clients based in Bali). Emails, phone calls, text messages, calendar/event reminders — technology never ceases to amaze and infuriate me all at once. 

If you want to make it in the freelance world, you have to be willing to go the extra mile and do anything and everything to sharpen and refine your skills, learn more about your industry/craft, and grow. This means, collaborating with others, going to networking events, attending workshops, and reading anything you can get your hands on that will help your business.

If you prove to your clients that you're responsive, capable, and human (not just someone in their screen), more work, contacts, and opportunities will come your way. You get what you give. Always.

Don't be one of those cliche millennials who get by doing the bare minimum, with little ambition. It's embarrassing the rest of us who actually want to make something real of ourselves. Work your ass off, edit and re-edit, pitch and pitch some more, fall and get the hell back up, give every single milli-second of your work your all and then some. I promise the reward is that much more significant when you do get it (not if you get it), whatever that reward may be for you.

So there ya have it! My 2k+ word rant on how I made the “millennial dream” of working for myself come to life. Call it ambiguous, or take it with a grain of salt, or drown it out entirely if you wish. This is just my experience and what I am capable of sharing.

Finding and having your own experience is what this freelance dance is all about. It's not easy or comfortable. Shit, it can be incredibly confusing and daunting. But I promise it will be the greatest gift you ever give yourself. It will push you towards figuring out what your version of a career or happiness looks like, what drives and inspires you in this world, all while living on your terms. It allows you to become who you want to be, rather than the person someone else might tell you to be, and that's beautiful.

When it comes down to it, life is about finding happiness. And happiness starts with you.