Recently, I began asking new subscribers to this blog to tell me their top obstacles as freelance writers right now.

The responses have been interesting, and in some cases surprising.

Quite a few of them are like this one:

“I enjoy your blog & I find it informative, but I’m still left with questions or uncertainty. I can’t afford your mentoring program, Freelance Writers Den, or even to hire/create a website (for now).

I would like guidance, so I can be sure I’m doing well in starting my business, as well as have any questions answered. I want to start off on the right foot, so to speak. How can I connect with other successful freelance writers & ask them to mentor/help me?”–Kay

So. This is awkward.

I have bad news for Kay. Even if there was a mythical free awesome professional writing coach who’d take her on as a charity case, and she got the mentoring she wants, her freelance writing business would still fail.

Why? Kay lacks an important — no, critical — thing you simply must have to launch a freelance business, of any kind.

I’m going to tell you what it is…even though I know it may make some writers hopping mad.

I don’t know if I’ve ever seen this uncomfortable issue discussed on a freelance-oriented website before.

But I think it’s not fair to delude writers who have no chance of making it as freelancers.

It’s going to be a dream-crusher for some. I apologize in advance.

Here’s the thing you need to know if you’re embarking on a freelance career:

What’s in your wallet?

To start a freelance business — or any kind of business, really — you need money.

But you wouldn’t know it to read most websites about writing, or freelancing, or building an Internet business.

There’s a disease going around about this right now that I’m going to call “no cost syndrome.”

The popular myth is that running an Internet-based business — a blog, or a freelance business — doesn’t cost anything.

Chris Guillebeau’s $100 Startup book is only the most recent tome to promote this idea.

Writers keep trying to start a freelance or Internet-based business…not on a shoestring, but on flat nuthin’. And then wondering, why they failed to make it work and had to give up and find a day job.

Here’s the reality: Ramping a startup business until it pays your bills — especially, making it take off quickly — takes money.

Whether it’s opening a shop on Main Street or putting out a shingle as a freelance writer, you have to invest in your business to make it succeed.

I get the sense it must be bad manners to mention this. Everyone wants to hear that freelancing is the awesome, magical business that defies all laws of ordinary commerce. And that you can start dead broke and you’ll skyrocket to amazing riches.

But boil it down, and freelancing is like any other business — it takes money to make money.

And meanwhile, your rent is still coming due.

How to be a freelance success

At this point in the 21st Century, if you want to present yourself as a professional freelancer to any reputable publication, website, company, or nonprofit, you need a decent-looking website. For starters.

If you’re really smart and want to stand out and get some quality clients right away, you may want to do some creative marketing, like a direct-mail campaign that costs money to produce.

You should have a professional outfit to wear in case an in-town client meeting comes up.

And of course you need a computer, an email provider, paid Internet, a web host, a printer, paper, toner, paper, pens, business cards, and more. Each dollar you put in will hopefully be repaid many times over, as  you get great clients because you seem so pro.

But the uncomfortable truth is, it all costs money.

The corrollary: As soon as your newborn freelance business starts making money, if you really want to build a solid income, the first thing you need to do is plow a lot of that initial money right back into your startup.

That initial money is not for paying your light bill. It’s for building your business.

You’ll improve your website. Join professional organizations and networking groups. Get on a plane and attend conferences.

Meanwhile, you need some other money to live on.

Why your no-money launch will fail

Beyond the realities of needing to invest in your business to make it thrive, there’s yet another harsh financial truth of freelancing.

The freelance life is often plagued with cash-flow problems:

• The computer hard drive dies and you need to buy a new one. Immediately. So you don’t miss deadlines and lose clients.
• Your client stops returning your calls and takes an extra month or two to send the check.
• Your pants rip and you need a new professional outfit to wear to meetings.
• Your car breaks down.
• You have an unexpected health issue, which your private insurance’s high deductible leaves you mostly on the hook for.

And so on. You get the picture.

As a freelancer, you are responsible for a lot of costs you didn’t have as an employee. Also, starter clients new freelancers tend to get are often the very type that give you the b.s. about how the check is in the mail, and leave you hanging for months.

Meanwhile, how will you eat?

I’m going to say the unspeakable: If you have no resources at all, you are too broke to make freelancing work.

You will get caught in a desperation cycle of taking any crappy client you find on Craigslist. Then, of being even more broke and desperate when that client screws you over, as lowball clients often will.

You could easily end up homeless. I know writers where it’s happened.

I realize it behooves me as someone who earns some of their living helping writers learn how to freelance to tell everybody, “Hey, you can do it!”

But I won’t.

You shouldn’t try to freelance if you are teetering on the financial brink. I won’t pretend that’s going to fly.

How to freelance when you’re broke

OK. So that was harsh. But some truths of the freelance life that need to be acknowledged.

Onward to the big question: If your bank account is empty, do you have to give up your freelance writing dream?

Not necessarily.

There are several ways you can overcome this “I’m too broke” problem and create the cash reserves you need to build a thriving freelance business:

• Get a side gig. I’ve known writers who pumped gas, worked as a bar back, sold Avon, and more when they started out. I worked as a legal secretary for years, to support my songwriting habit. Stop buying the starving artist mystique and figure out how to put aside some money to support you as you transition into freelancing.
• Get a full-time day job — for now. It’s also feasible to freelance on the side of a full-time gig. Takes a lot of discipline, but it can allow you to pick and choose good clients and build a quality portfolio a lot faster.
• Find a sponsor. Maybe your spouse’s day gig will cover the bills and give you some ramp-up cash to work with.
• Lower your expenses. Take a look at your costs — could you live in a cheaper dwelling? Take on a roommate? Stop buying lattes? Cut out cable? Most of us have optional expenditures we make and could lower our basic monthly costs if we got creative.
• Fill the gap with credit cards. I once had a screenwriter friend who would calmly charge her groceries between gigs, confident she’d soon be writing for another TV show. If you have a high risk tolerance, this might work for you, too.
• Liquidate assets. Got a second car you could live without? Some collectibles you could sell on eBay? You might be able to turn some possessions into cash.

If you’re not willing to do any of this to get a cash cushion you could use to bankroll your freelance writing startup, then I have a question to ask you:

Do you really want to do this?

Reaching for dreams usually involves sacrifice — read any fairy tale you like.

What are you willing to give up to never have a boss again?

If you can’t make any sacrifices to find some cash to get started freelancing, then it’s probably not going to happen. Even with the best writing mentor in the world.

What do you think — can you start freelancing with no money? Leave a comment and give us your take.

Do you find yourself unable to get focused on your writing?

It’s a pretty common problem among writers. Among all freelancers, really.

Let’s face it — distractions are everywhere for the home-based, self-employed person.

There’s laundry to do, neighbors who stop by, and of course online there are distractions our grandparents couldn’t have dreamt of.

We all get distracted sometimes, or just want to goof off — after all, that’s one of the perks of being a freelancer!

But what if you can’t ever seem to focus on writing?

That’s bad news.

When procrastination takes over

Take this question I recently got from a writer and new mom who wanted to know if I’d accept her into my one-on-one mentoring program:

“I have a real issue that I can see killing my career really quickly if I don’t do something about it now. So far, getting gigs has not been a problem at all. I seem to get them with relative ease. My issue is the follow through.

I’m a stay-at-home mom with a 13-month-old, so I have that working against me. The problem is, when I should be working, I end up frittering away my time on Facebook, Twitter, checking email, even lurking around on Freelance Writers Den. The rest of the time, I’ve got my daughter to attend to, and before I know it, the day is over and I’ve done nothing. I’ve tried holding myself accountable to my husband, my mom, an accountability partner from the Den, and motivating myself by dreaming up ways to spend the money. I’ve tried programs that bar you from certain sites, but I always find something else to waste time on. So I think the issue is much deeper.

What I really need is someone to put the fear of God in me, because I’m not able to do that myself. I think my problem is a combination of self-confidence, lack of motivation, and poor productivity. I’m just not sure how great a role each one of those plays or how to get to the root of my problem.

I’d like to discuss the possibilities of mentoring with you as I think you’ll be able to help me out of this rut and get me on my way.–Tiffany

I turned her down for mentoring…because this isn’t the sort of thing that a writing coach or business mentor can really help you with.

In my mentoring, I help writers create goals and a marketing plan for reaching those goals, based on their specific experience and interests…and then if you’re this sort of writer, you’re going to procrastinate and never execute on that plan.

So that’s no help.

How can this writer snap out of her funk and get writing? Here are the possible causes of massive procrastination that I raised with her:

Bone-crushing fear. You may do the less threatening things because you’re scared to turn in that assignment. If you’re circumventing Freedom or whatever social media-blocking site you use and still timewasting, there’s definitely an emotional reason. This is something you really need to talk to a therapist about. Hypnosis, positive affirmations, and other techniques might help you break this fear down.

Not enough drive. At the end of it, being a freelance writer is about you really wanting to DO this. People love to vent and blather all day about their big dream of quitting the boring day job and being their own boss…but in the end, we each make time in our lives for the things we really, truly want to do.

If you’re never making time for it, maybe it isn’t the driving passion you thought it was. Maybe what you really want is to wait until your child goes to preschool to do this. Not a crime to feel that way.

Employee syndrome. Ultimately, we’re our own bosses as freelancers…and I’ve found some people just can’t make that transition. They can’t MAKE themselves hustle the way a boss put the fire under them to get it done. It’s a different mindset. You can help build your “boss” muscle by reading books about entrepreneurship…but ultimately, some people don’t have this muscle.

Need a scene change. Some people are more productive if they can get out of the house — especially writers with young kids underfoot. Consider trying a coffeeshop or coworking place to break your procrastinating routine.

Self-limiting behavior. You say you’re getting clients — are you blowing their deadlines and angering them and failing to turn in your work? Or are you getting it done? If you’re still making the deadlines you have, it’s possible you’re not doing more because you don’t want any more work than this. If you’re blowing deadlines and losing clients, maybe you subconsciously want a lighter workload than you have and more mommy time.

Too much juggling. Are you trying to dabble in several different projects per day, all while also minding a toddler? That’s enough to rip your brain straight in half. Instead, focus on a single client per day — I tried that and found I was way more productive.

Unrealistic goals. You have a 13-month-old at home — do you have any child care, or are you imagining you can somehow magically write articles while you meet the insatiable needs of a toddler?

I think you’re probably doing little timewaster things because you don’t have any ‘heavy lifting’ time, as Mike Vardy would say, when it feels like you have a substantial, viable hunk of time in which to either write, interview, or market your business. So you keep doing a few little low-level tasks and never reach the main event — writing.

If you don’t have a sitter, know that a home business does not magically happen while you watch a baby full time. Total myth. If you have a sitter, you likely need more hours. Consider finding a co-op and trading hours with other moms — I did, when my first was a baby.

I know — you don’t want to miss a minute of these precious childhood years! Except that if you want to build a business, you’ll probably have to miss a bit of it. On the other hand, baby won’t be living under a freeway overpass if you can pay the bills, so it can be a positive tradeoff.

No goals. Are you setting goals? If so, then you can break those into smaller goals for this week and this day. Leave the office each day with your top three things you MUST do tomorrow sitting and waiting for you the next day. When you’re sleep fogged half the time with a baby, you need that, or you’ll easily waste the whole day trying to remember your priorities.

Have you got more advice for this procrastinating writer? Leave it in the comments.

I spend a lot of time on this blog helping writers figure out how to find more and better clients.

Today, let’s look at a problem on the other side of the spectrum.

One writer recently emailed me with her tale of woe — she is overloaded with work and falling out of love with writing:

“How do you handle extreme burnout in freelance writing? I am going through that now and am floundering with my writing. My quality of writing has gone way down. I have been fighting this with a purple passion, but my work is suffering.

“Another problem is that I lost my major client last Friday due to the economy and my boss’s subsequent layoff. I am so turned around I don’t know what to do. Any advice would clearly be appreciated. I don’t want to leave my writing, but I am so burned out that I am not providing quality work.”–Teresa

This is definitely a bad situation. Makes me wonder whether that layoff was really because of “the economy,” because we all know what happens when you’re burned out.

You get fired from some of your better gigs. Suddenly, instead of burnout being the worry, it’s starvation.

It’s become a tradition for me to throw at least one holiday-time mailbag question to my great readers to answer, so I’m turning this one over to you. I can’t wait to see your tips!

Can you help this writer avoid burnout? Leave your advice in the comments.

P.S. Congrats to Becca, who won a free ticket to the upcoming Freelance Writers Den bootcamp, How to Use Social Media to Get Freelance Gigs. Get details on this training by clicking below:

There’s a whole lot of freelance writing advice floating around the Internet. There’s a lot of it just on this blog.

Sometimes, writers tell me it’s overwhelming. Couldn’t I just boil it down?

One recent email from a reader brought this home to me. She wrote that she is an experienced writer but had never freelanced and needed to start making money fast.

Also, she couldn’t afford to spend anything on her career right now, not even $25 for a month in Freelance Writers Den.

She wasn’t sure where to begin, and was hoping I could give her a snap answer that would make it happen:

“Please help me!  I know that I have the talent and skill – from past REALLY successful copywriting projects and jobs. I’ve done assignments for Fortune 500 companies and have even won awards. 

Could you at least give me the basic secrets for freelance writing success, to get me going?”

I don’t know how secret they are, but yes, I think there are a few basic things you must have, if you’re going to start earning as a freelance writer.

Here’s what they are:

1. A can-do attitude

Are you fired up and burning with a passion to make your living from writing and be your own boss? Are you confident about your skills and willing to put yourself out there?

Most of the writers I meet who aren’t earning are trapped by fears and low self-confidence. They think up excuses about why they can’t move forward — they need a journalism degree, for instance, or the economy’s too crummy to possibly make it as a freelancer today.

Trust me, you will not encounter any bigger challenge out in the marketplace than the negative tape you’re playing in your head.

When writers tell me they’re dead in the water because they can’t find an editor’s email address, or simply can’t manage to hit “send” on that query letter, I know they’re kidding themselves. They’re not doing it because they’re scared.

Pledge to be an unstoppable force until you have the clients you need to feed your family.

Be willing to get creative to solve the obstacles you encounter. Don’t take “no” for an answer. If the rules aren’t working for you, bend or break them or make up your own.

2. A writing habit

If you’re sitting home, waiting to get an assignment in order to write something, this isn’t going to work. Writing is a muscle that needs to be built up, like any other in your body. You need to be working it all the time.

Also, you ought to be writing because you love it. If you don’t love it, this probably isn’t the career for you.

So keep a journal, start a blog, write long letters to your grandma. Have a habit of writing. There is no substitute for writing in quantity and on a regular basis for growing your skills.

If you used to be a reporter like my reader above and now you want to get back into it, begin by writing again. Find pro bono clients who’ll let you do sample work — anything to get the words flowing again. If you’re brand new to writing, same thing — start writing. Then, keep writing.

I was a staff writer for 12 years, required to write at least three stories every single week, often more. If you looked at my writing the year I got that first job and my writing at the end of that time, it is like night and day. Huge amounts of writing will build your skills — and your confidence.

3. A willingness to market

This is the one that divides the women from the girls, as far as earning a living as a freelancer.

Every one-on-one mentee I have ever worked with, I start by asking them one key question. The conversation always goes like this:

Me: So, to begin why don’t you tell me what you are currently doing to market your freelance writing business, so we can talk about what else you might do.

Mentee: You know, I actually haven’t been doing any marketing.

Writers who understand they are running a business know they will need to make marketing a regular activity in their schedule. So understand. This is a business.

Put up a writer website. Get business cards and go to networking events. Get on LinkedIn and start working it there.

Expect to be marketing aggressively for 6-18 months to get your business afloat and build up your client base to where you have a steady flow of good-paying work. It’ll get a bit easier after that, but marketing never goes away.

If you don’t know how to market your business, subscribe here on the blog and get Marketing 101 for Freelance Writers. That ought to get you started.

4. Mentors

If you’d like this process to take ages, try to figure it all out yourself. If you’d like to move along faster, try to lasso an editor or two into critiquing your work on a regular basis.

This is actually how I learned all the basics. Two wonderful editors at two print publications thought my writing showed promise and were willing to be peppered with questions by me on why they changed my lede and cut the quote I loved, and all that. I’d probably still be getting $50 an article if it weren’t for these incredibly giving men.

When I started my blog, same thing. I connected with mentors through Twitter, and through networking groups I joined, who saved me a ton of time and aggravation. You probably wouldn’t be reading this now without them.

5. Writer friends

Finally, no writer is an island. This is lonely work, and your family and friends won’t understand the particular challenges you are grappling with. You need to meet other writers and hang out with them, both online and in person.

Personally, I’ve benefited greatly from going to Media Bistro’s live events…but check around in your town. Do a Google search for the key words you’re trying to rank on and see who tops that search. Then, ask them what writers’ groups are hot locally.

One of those local listservs brought me a lead that turned into a $60,000 client that ran for more than two years. It’s really worth asking around and knowing other writers, especially in your niche. Trust me.

–

Those to me are the nuts and bolts you need to get your freelance business rolling. If you’ve got questions about getting started in freelance writing, you should know I have vowed to answer 100 freelance writing questions on a recent blog post. Last time I checked, I hadn’t hit my limit yet, so feel free to add yours on there.

What other basic things should new freelance writers do to get started? I’d love it if some of my more experienced readers would add their tips in the comments here.