It only took six months after college graduation for me to realize that I hated cubicles. The fake privacy that they represent. The feeling that the half-walls are going to close in on you.

Cubicles just aren’t built for a physical and psychological claustrophobe like me.

The truth: I didn’t want to work for anybody. It was more genetics than personal choice. My father suffers from the same fate. He is going to be his own boss, no matter what.

I wanted to be an independent something (at that time, it was writer, but as I eventually learned, most independents have to expand beyond their intended passion in order to secure the necessary multiple streams of income).

When I first struck out on my own—meaning, left a safe, comfortable job with benefits and a consistent, bi-weekly check—I felt free. Whose world is this? It’s mine, it’s mine, it’s mine.

I shared my lofty news with an older woman, a freelance publicist.

“Are you sure that was a good idea?” she asked me. I jerked my head back at her inquiry. Was I sure? Hell yeah. This is what I knew:

I had much bigger ambitions than any 9-5 could ever offer me.

I didn’t want a cap on my income. I figured, if I worked for myself, I could make as much money as I wanted—it just depended on how hard I worked (at that point I didn’t know the difference between working hard and working smart). But if I stayed at my 9-5, the not-promised five percent salary raise wasn’t going to cut it.

So when she asked me that question, I had strong ammo to shoot her down.

And I did.

“I’m just saying, prepare first,” she countered. “When I started, I just jumped out there with no plan or clue about what I should have been doing and I had to pay for it, literally.” She then went on to warn me about the mistakes that bright-eyed newbies make.

Fast-forward six years and here I am. Independent. Still. I started and shut down one business. I recently started another. I even threw in the towel once and took a 9-5. That didn’t last long.

Throughout it all, some things never changed:

Freelancing, working for yourself, going independent, becoming an entrepreneur, whatever you call it, ain’t easy. It’s not for everyone. I repeat: it’s not for everyone. Not everyone is built for this lifestyle, because at the end of the day, it’s more than just a career choice.

Sure it looks glamorous. Taking meetings in pajamas, as I so often do. Concluding my day at 1:00 pm if I like. Early happy hours. Traveling without putting in for vacation. Not having to take orders from an incompetent boss. Best of all: pursuing my life’s passion without apology.

But that reality, more often than not, also includes the following:

Non-Paying / Slow-Paying Clients
I wish I could say that this just sucks. But it’s deeper than that. Non-paying or slow-paying clients affect your ability to eat, your livelihood. And unfortunately, they are so damn prevalent. Big clients (it can take them forever to process contracts and other paperwork) and small ones alike. Sometimes you have to put in extra work to compensate for the slow income and to account for the fact that there’s:

No Such Thing as Sick Days
For most people with traditional jobs that offer benefits, when you don’t show up, you still get paid. Call in sick; those eight hours will still be on your check.

For many independents on the other hand, when we get sick, work stops. And usually, there’s no one to pick up the slack. And if work stops, so do the checks. Clients don’t really care that you have strep throat; they want their projects finished on time. So many of us work through our sicknesses (often because we don’t have health insurance, but that’s a discussion for another day), not really giving ourselves time to get better, which leads to:

Burn Out / Lack of Balance
Too many entrepreneurs don’t take care of themselves the way we should. We work. Work. Work some more and then work again. We skip vacations. We neglect the other parts of our lives—hobbies, family, friends, relationships—until we burn out. This is not good on the mind or the body and is usually the result of an intense pressure to always practice:

There is no boss telling you when to do something or even what needs to be done. Ultimately, you’re responsible for everything.

Time is the entrepreneur’s most valuable asset. If we don’t spend it correctly, we don’t eat. Period. So we have to be (or feel we have to be) super productive at all times.

Unlike when I used to work at a traditional 9-5. Some days I just didn’t feel like working even though I showed up at the office. So I didn’t. But guess what? I still got paid.

When the self-employed don’t show up, things fall apart, because you’re probably:

Doing Everything Yourself
I mean everything. Marketing. Accounting. Finance. Business Development.

All the while trying to do your real work too.

I used to be so grateful that I didn’t work in accounting at any of my jobs. It seemed like such a tedious department that I was happy to send invoices to and have them processed without any further action from me.

When you work for yourself, just starting out, you are your accounting department. And if you don’t stay on top of invoicing and accounts receivable, guess what? Yep, you got it. You don’t get paid. You don’t eat. But what’s probably more important to ensure is that you pay your:

Ah, the bane of the independent’s existence. See, for the most part, we’re W-9ers. Clients pay us without deducting taxes. Oh the checks are lovely! But only to you. Uncle Sam still wants his money.

And unfortunately, some of us forget this. Or it seems, at the time, that we just can’t afford to put away a specific percentage of each check to account for taxes. When it’s time to pay up, the money is gone and Uncle Sam hits you with a nice tax bill with extraordinary penalty fees. Of course though none of this matters if you’re not making money, an act that requires:

While there are dreams of spending all your time dedicated to your passion, the truth is, much of your time is dedicated to hustling for work, for clients. You’ll feel a difference in your business, the moment you stop pursuing opportunity.

Trust, this by no means an attempt to talk you out of going independent. I champion people to be their own boss, to start businesses.

What I didn’t realize six years ago is that the O.G. was right. Preparation is important. Part of preparation must include knowledge gathering and understanding the full face of working for yourself.

And once you do that, I think (and this opinion may change a year from now) that the major key to entrepreneurial success is iron discipline. A discipline that allows you to say no to projects that don’t make sense, a discipline that forces you to stop working and spend time with family. A discipline that accounts for the time that you need to take to rest, rejuvenate, and do nothing. A discipline that ensures you put away money from each check to pay your taxes and that you maintain a significant savings cushion.

For me, I know I can’t have it any other way. I’m just like my father. Cubicles still scare me. I enjoy the freedom of working for myself—choosing the projects that I will take on. Pursuing my passion with full force and without apology.

I just had to stop romanticizing the life I’ve chosen in order to fully embrace it, love it, and be successful in it.

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  • This is a great article that puts a very honest and clear focus on what it means to freelance. Well appreciated.

  • Cali

    I wish I’d read an article like this before I started freelancing – it wouldn’t have deterred me at all, just helped me understand what was to come (especially the TAXES!!). THANK YOU for this article, I totally relate. Been freelancing for quite a few years now, I still don’t sleep well when I’m in between jobs but I’m trying to get used to the rollercoaster – it all seems to work out somehow in the end. & I agree on the loneliness angle someone brought up, it’s very true – because of my hours (nights) I meet less people, men in particular. All of it would be easier to handle if I was contributing to a shared income & knew someone had my back, but that’s another story ain’t it?? LOL

  • Nice read, my first business yielded $500 for the year!!! I was so hurt, thought I would be doing it big, humbling would have been a step up from dejected! But I picked up what was left of my pride and kept on, keeping on….

    People only see the glamour, not the thorns.

    However….with that said I would not trade my “job” for anything in the world. Sure it is hard, there are days I go hang out at Starbuck to chit- chat and other days, I wake up and say “I ain’t doing a damn thing today”

    On the flip side, with all the projects I have on the board, I will make more money than I have EVA made in my life in 2012! It took me 12 years to get to that point, there is something to be said about being consistant.

    Some tips, learn to save 30/50% of what you make, there is nothing like a war chest to keep doubt and fear at bay, about you “life” choice. If this means getting a “roomie” do it, your dream is bigger than have your own space, if you are real about it.

    Write down your goals, I attribute this one thing to 90% of my success!

    Get all the credit you think you will need in life before you quit your job!!! Make sure all balances are $0! After 3-5 years, the applying for credit will not be an issue, unless you get pre-approvals it can be tricky!

    Realize all money is not good money! Every job is not worth accepting, you sell yourself short, you will regret it! This is not to be confused with being realistic about your value in the marketplace. Just know some of the clients you give the best deals to , will be the biggest PIA you ever encountered!

    Join an group of like minded self employed folks and if you can’t find one , create one! Having a peer group can be invaluable and it might even get your more business.

    Start investing, I don’t care if it is only $25 dollars a month, build the habit, so when the long money comes in you will do the right thing!

    Most important remember to have FUN!!!

  • I completely agree with all the points. I recently completed my first year as a freelancer. It has been nothing but a year of life, I mean business lessons. I recommend that anyone wanting to start a business stay in corporate America as long as you can bear it. Everything is about who you know, make those contacts and do as much professional development as you can on someone else’s time/dime.

  • This is my predicament NOW!! Luckily I have savings (that I of course don’t want to touch) and am willing to take on a part-time gig til “my thing” pays off…

    Great read!