Analyzing the situation

When I found myself unemployed and looking for options, I had a few things on my side and a few unique problems on the horizon. On the plus side, I had an employed wife and a few thousand dollars in the bank. I also had this blog, which generates enough income to provide some cushion, but not enough to pay all of my bills.

What I did not have was a single freelance client. For a while, I had balanced freelancing with my last job, but when my job grew more demanding I stopped freelancing. Additionally, although my wife was employed at the time, she had already made plans to take the next year off to finish her Master’s Degree. This meant I only had about two months before our income took another major hit.

Establishing an income with easy sources

As you know, there are some low-paying but easy-to-land opportunities on the web. I’m not going to discuss which service I used, but I found an online content provider and started churning our quick, moneymaking content for them. It wasn’t particularly enjoyable work, but I was able to start earning again within days of losing my job. I made about $2500 over the course of two months. It allowed me to feel productive while I looked for more lucrative opportunities. It was also a steady freelance gig that I could quit at any time without repercussions.

Cutting expenses

Like most people faced with a major cut in pay, my wife and I started to cut expenses. We dropped our premium cable package. We minimized our mobile phone plan. We deferred my student loans. We went out less and shopped much more carefully. Some expenses just naturally faded away. I was no longer commuting 130 miles round trip to work and eating out with my co-workers. My wife and I also went down to one car. That last expense cut wasn’t entirely voluntary; our minivan caught on fire.

Using my social network

Once I had some money coming in, I concentrated on improving my presence on the web. I upgraded my online portfolio site. I updated my resume on sites such as Monster, Dice and LinkedIn. I let my friends on FaceBook know I was looking for work. I also had lunch with friends and former colleagues, some of whom were also out of work.

Because I did this, I got a few leads. One of these was at a company I had interviewed with before. The interviews had gone well, but they had been unable to offer me a full-time position due to budget cuts. I contacted them and let them know I was available as a freelancer.  They had a project for me and we started working together. One project led to another and I maintained them as a steady source of income for almost six months.

Expanding my base

I have yet to find another client that provides me with the steady work of the first big client, but nine months after losing my regular job, I have a number of smaller clients that are keeping me afloat. In many ways I prefer these smaller clients, because they provide more variety and stability than focusing on one big client for all of my income. Concentrating on one big client is almost the same as having a regular job. You become reliant, and that is dangerous. My one big client knows I’m there if they need me again, and I stay in contact.

Moving on

My goal now is steady expansion. Because I also have my blog, I am not entirely reliant on freelancing for my income, but I am entirely self-employed. My wife and I are able to pay our bills, but I want to do more than just get by and stay afloat. We’re a two car family again, but we are still shopping carefully and avoiding major purchases that we would love to make. My wife will graduate in another two months and probably return to her old employer. This will ease some burdens, but it also means that student loans will once again be in the picture. I have my own number in mind for how much I need to make, and I will keep pushing until I reach that number.

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Print media is in trouble

Now, as we enter a new decade, print media is in genuine trouble. Newspapers have long been in decline and magazines are following, sunk not only by the speed of online information, but by the rising costs of mail delivery. Book publishing is also making rapid changes. Bestsellers are still bestsellers, but for the first time, online books are starting to make real headway. The iPad and the Kindle are now solid sources for books. This has made self-publishing and small press publishing more viable than they have been in years. When you can search for what you want online, the press to get on shelves at stores is lessened somewhat. It becomes more important to be the book that people search for, rather than the book that publishers promote.

You are not as ready as you think

If you are on the cusp of the technological wave, don’t pat yourself on the back just yet. Sure, blogs are more popular, but a livable income as a blogger is still a challenge. The same goes for podcasting and social media. You hear about the people who make money at it, but you hear about them because they are the exception rather than the rule. People are more immune to advertising than ever before, and if they aren’t buying something, you aren’t going to make much money.

There is no roadmap

Change is in motion, and accelerating. The financial landscape of publishing and media in general is in the midst of a major transition, and there is no definitive idea of where it will end up. This makes picking a career, especially in the writing field, a tricky matter. We currently live in a crowded publishing world. Anyone who wants to publish can. That brings great freedom, but it pushes the level of competition through the roof. When media was controlled by a few gatekeepers, the goal was to get past the gate. Now, the big gatekeepers are still there, and can still offer a measure of success, but your true competition is the crowd. When everyone can be heard, it becomes increasingly difficult to stand out. When someone else is offering what you have for free, it is very hard to charge.

Fortune favors the adaptable

My point is that if you want to have a career as a writer, be prepared for change. Be prepared for an entire world of competition, but also a world of possible readers. Understand that the way you make money writing today may soon change and that you will have to adapt to that change. We see this most in the freelance world, but don’t be surprised if corporate writing world follows. No one is immune to change.

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Despite the situation, freelancing was still my choice. I could have devoted all of my time to finding another regular job. I could have taken a lesser job, or at least tried to find one. I could have just sat on the couch and watched TV, waiting for circumstances to change. That last one may not seem like much of an option, but I have seen plenty of people give it a try.

Here are some questions you should ask yourself before jumping into full-time freelancing:

Are you dissatisfied with what you are doing now?

Most people contemplate freelance writing because they are dissatisfied with their current situation. They don’t like their job or they don’t like how little time their job leaves for them to write. They think they are meant for better things and freelance writing comes to mind.

Dissatisfaction is a reason to try freelance writing, but it is not a good indicator of success. Dissatisfaction with a regular job is common and freelance writing is no picnic, especially for a poorly motivated worker. Often times, when a person thinks time is the reason they aren’t writing, it turns out that they weren’t really going to write no matter how much time they had. There is a difference between a pleasant sounding alternative and reality. Dissatisfaction is a start though.

Have you tried freelance writing part-time?

Jumping from a 40-hour-a-week job to full-time freelance writing is not one smooth step. If you aren’t actively freelancing while employed, you are going to have a hard time transitioning to full-time freelancing. There is a learning curve to any job, and starting freelancing from square one without an income is difficult. You will want some ongoing clients or at minimum some experience with freelance writing before you try to make the jump to full-time. Prove to yourself that the career is important enough for you to sacrifice some time in the present before you decide to make it a profession in the future.

Have you saved up money?

It is important to have money set aside when you start freelancing full-time. Starting with enough money in savings to pay all of your bills for six months is a good start. Having a year or two years worth of money is an even better start. A good way to start saving for a full-time freelance career is to put all of your part-time freelancing money into a savings account, living only off your regular income until you are ready to make the leap.

Have you done your research?

There are several things you need to know when you strike out to be a full-time freelancer. The first is what your income requirements are. What will it take to pay your bills? Figure out just how many clients you are going to have to land and what you will have to charge if you want to be self-sufficient. Remember as well that you will have to find a way to take care of things such as medical and dental expenses, as well as other bills that only crop up sporadically but are bound to show up eventually. Office equipment needs replacing and upgrading. Cars need fixing. Houses need repairs. Christmas comes along once a year. Be realistic about what you are going to spend.

Once you know what you need, you have to figure out how you are going to meet that number. This means that you decide what areas you want to focus on (writing type, client type, locale) and have a marketing plan in place for reaching the people you want as clients. In fact, you will want to do more than research those markets, you will want to already be approaching your potential clients before you quit your job. Don’t leave it all until the day you finally stop working your regular job.

Do you have self discipline?

The final piece in the puzzle is to think long and hard about whether or not you have the discipline for self employment. Life without a boss sounds great, but it means that you have to be the one to push yourself to achieve. You not only have to be able to complete the assignments that come your way, you have to work hard when you don’t have any assignments. You have to market yourself and land new jobs. You have to make yourself sit in the office and work when it is a beautiful day and no one would complain if you put everything off until tomorrow.

A full-time freelance writing career is not for everyone, but for the people who can handle it, freelancing can be a great way to make a living. If you feel confident about your answers to these questions, they you are probably ready to make the leap to full-time freelancing.

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How do you want to spend your energy?

There is only so much time in the day, and that means you have to be careful about the jobs you take. You don’t want a job that is going to make it impossible for you to write outside of work. That is why some people take jobs far from the writing field. Some jobs only require presence and a little attention. Working as a security guard, for example, allows you to spend most of your time standing around watching people. For some writers, this is a great opportunity to observe, and get paid to do it. It isn’t difficult work, and it won’t leave you intellectually drained at the end of the day.

Working as a technical writer or as an editor gives you a chance to improve your writing skills as you earn a paycheck (and a bigger paycheck than a security guard). The downside is that you may use up all of your intellectual energy reading documents and attending meetings. A construction job is an example of a third option, one that works your body more than your mind, and gets you out into the daylight instead of stranding you in an office building. It is up to you to decide what works best for you, but if at the end of the day you don’t feel like writing, that’s a clue that you made the wrong choice.

Part-time solutions

Part-time work is yet another option. You draw a somewhat smaller paycheck, but you get back more of your time. Working two days a week at a store in the mall probably won’t pay all of your bills, but it may be enough to get you by in the weeks between freelance payments. It will also remind you of why you want to work hard as a freelancer, so that you don’t have to hold a job like that anymore.

Temporary solutions

Another option beyond part-time work is temporary work. You work full-time or even overtime hours for several months, banking your paychecks so that you can then have money in reserve to support your time freelancing for the next few months. The benefit of this, beyond the money, is the additional motivation to do well. You won’t have to get a regular job again until you run out of money. That gives you extra incentive to work hard and get paid as a freelance writer so that you don’t have to go back to a regular job. The danger is that you won’t know when to quit. Months can quickly turn into years, especially if you don’t save your money well.

The important thing to remember is that you do have choices as a freelance writer. When the freelance market gets slow, a job will provide you with another source of income and security. Just remember that your primary goal is to make a living from your freelance writing.

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Make a list of tasks

The first step in task organization is to make a thorough list of all the tasks that you need to accomplish, want to accomplish, and hope to accomplish. It will be large list so don’t be frightened. Almost everyone has more tasks on their list then they can reasonably accomplish. You can achieve anything you want to achieve, as the saying goes, but you can’t achieve everything you want to achieve.

Set task priorities

After you have the list developed, you should go through and prioritize the list. There are plenty of ways to set priorities. You can list them as 1, 2, 3 or high priority / low priority, for example. What I do is break the list down into categories:

• Tasks I absolutely have to do
• Tasks I want to do and have the time and resources to do
• Tasks I should do soon
• Tasks I want to do but don’t have the time to do
• Tasks I am willing to put aside
• Tasks I am waiting for other people to do

You can pick your own categories, but it is important to have at least one list of things you aren’t going to do for now. This will get them off your mind as long as you make an agreement with yourself to review the list regularly.

Break tasks down into steps

Once you have your list, take the items that are your top priority and review them to figure out the steps you need to accomplish each task. Sometimes you can map out the whole process. Sometimes you need to settle for just listing the next step. Whatever the case, get clear on what you need to do or have in order to proceed. Be sure to keep special track of time sensitive tasks. Task management is different from time management, but it is still important to recognize that some things need to be done within a limited time span.

Pick tasks that are appropriate

Once you have your list completed, pick the item that you are most ready to do and proceed. Try to pick things that are appropriate for your available time and energy levels. If a step can’t be completed in the time allotted, you either need to break that step down into smaller steps, or pick something more appropriate for the time you have available.

Work through problems

Keep your list handy and review it as often as needed. Mark off your completed tasks and move on. If you find yourself avoiding a particular task for longer than you should, evaluate the task again. Chances are you’ve left out an essential step or requirement and are unsure of how to proceed. Some tasks, of course, are just plain unpleasant, but they are on your list for a reason.

Celebrate your accomplishments

As you complete the high priority tasks on your list, allow yourself to feel a sense of accomplishment. Don’t fret the fact that there are still more items on your list. There always will be. If you ever got close to finishing, you would think up more things to do anyway. Focus on what you do accomplish rather than what you don’t. Evaluate regularly and keep moving forward.

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You sell a product

If you are a writer, then your writing is your product. You have to sell that product if you want to make a living. This means that you need to learn about sales. Take a class in marketing or at least get yourself a basic book on sales. Whatever your end product is, from articles to poems to short stories, you can only make a living if you make sales.

You are a product

Beyond your writing, you have to sell another product. That product is you. Whether you are trying to land an assignment, a contract, or a job, you need to sell people on the concept of you. They have to believe that you are the right person for the job. They have to believe that you will not let them down. They even need to like you. You have to make people want to do business with you.

You have to do things you don’t love

With any luck, you got into writing because you love to write. If you didn’t, you should seriously find another profession, because there are plenty of better paying and less stressful careers out there. If you do love to write though, you also need to learn how to do things such as desktop publishing, bookkeeping, taxes, promotion, research, attending meetings, networking, project planning and customer service. They are all part of the business and you ignore them at your own peril.

You need to manage yourself

You have faults, I know I do, and some of these are going to get in your way as a writer. You may be shy, awkward, lazy, scatterbrained, argumentative, easily distracted, bad at math, prone to depression, a perfectionist, etc. You need to be honest about whatever your deficits are and find ways to keep them from damaging your writing career. Whether you need to get a friend or hire an assistant to keep you on task, or hire an accounting service to keep track of your money, you need to be sure that the important things are being taken care of, either by you or by someone you trust. You need to keep yourself working.

You need money

You can’t make a living without an income. That means you may need to write about subjects because they will make you money, or take on additional non-writing work to keep you afloat. This is the reality of having a writing career. You don’t always get to do exactly what you want. You need to think in terms of how much money you need, and how you are going to get it. Sometimes that means taking on assignments you don’t love. Sometimes it means simplifying your life and giving up luxuries or even some basics so that you need less money. Whatever the case, your income matters and you have to find a way to live on the money you make or make more money.

Think like a businessperson

You are free to write like an artist, but you have to think like a businessperson at times. It is a good idea to take business classes, organization classes, and marketing classes. Once you know something about business, it will be easier for you to think of new projects in terms of how you can make them work for your career so that you can keep writing.

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Your life and your career start to meld

As a freelance writer, there is no moment when you are suddenly at work or off work, especially if you work out of your home. There is nobody to tell you when you are done working for the day, and if you sleep in and miss a couple of hours in the morning, there is no one standing over you telling you to get to work or to keep working into the evening to make up for it. This leads to a perpetual feeling that you really should be doing something other than what you are actually doing, whether you are working or relaxing.

Your are responsible for your own goals

In a job you may have been able to blame your boss or the company for your lack of career advancement or your low pay. As a freelance writer, your career is entirely your responsibility. You make the decisions and you live with the consequences. Instead of negotiating with one boss, you have to negotiate with multiple clients and each one may have their quirks or issues. Some may even be hoping to rip you off. That is the reality of the business. It isn’t as safe as a regular paycheck and it isn’t for people who are afraid to make decisions.

You create your own network

As a freelance writer, you don’t get to meet coworkers in the lunch room or gossip over cubicle walls. If you want allies and friends, you have to forge the connections and keep them active. It can be lonely sitting in a home office all day with only the cat for company. A feeling of isolation is common. Social tools such as Facebook and Twitter can help you feel connected, but there is no replacement for face-to-face contact.

Life becomes deductible

As a writer, you have to manage your own taxes. That means paying the government out of your own account once a quarter to cover both income tax and social security (in the USA). It also means that anything in your life that legitimately helps you write becomes a deductible expense. Some of the typical deductible expenses are books, classes, Internet access, phone, office supplies, business cards, and computer equipment. Depending on what you write about though, other things become deductible. Someone who writes about exercise might deduct their shoes and gym membership. Someone who writes about travel might deduct their vacation expenses. This is why it is important to track all of your expenses and make sure you can justify any deduction you take. It may be smart to consult a tax accountant.

Your income relies on your output

If you get nothing done all day at a regular job, you still get a paycheck. Some people manage to survive in corporate America for years without accomplishing anything. As a freelance writer you don’t have that luxury. If you don’t do the work to land new clients and produce new writing, you don’t make money. Everyone has an off day once in a while, but if your off days start to stack up it can seriously endanger your financial stability. This is especially hard for freelance writers because people respect your time less than they do if you work a regular job. The friend or relative who would never call you at work won’t hesitate to call you at home. If you give in to these distractions, you have no one to blame but yourself. You are your boss.

Think about these realities before you jump into a freelance writing career. Full-time freelance writing is not for everyone.

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Sit down at the beginning of each day and look at your current assignments. If you don’t have any assignments, make marketing your assignment for the day. Make a list of the three things that you most want or need to move forward on that day and decide what steps you are going to take. Tackle those items as soon as possible, before the day gets in your way.

Make a daily don’t do list

Make a list of the things that you aren’t going to do that day. This is for your peace of mind. Write down any of those nagging tasks that you think you need to do but know you won’t do. Get those items on paper and off of your mind.

Throw away everything you don’t need

By throw away I mean throw it in the trash, recycle it or give it to someone else. Everything in your office that you don’t need is a potential distraction. Yes, you are welcome to have art and other things that aren’t entirely necessary but make life better. Just get rid of the junk, and realize that most of the things in your office are probably  junk.

Keep track of the ways that you waste time

If you stop working to log on to Facebook and read your messages or play Viking Clan, write it down. If you stop to check your email, write it down. Make yourself list all the ways that you waste time. It will keep you honest.

Log your thoughts and ideas

Keep an open text file, a notebook, a smartphone or an audio recorder. Whenever you have a thought that seems valuable or won’t get out of your head, record it for later. You can review these thoughts at the end of the day to determine their value and any ways that you want to move forward.

Apply the 80/20 rule

The 80/20 rule, which applies to so much of life, is simply this. Twenty percent of effort results in eighty percent of results and benefits. Review your time and your projects and determine the most valuable way to use your time. What do you do that actually results in income, and what do you do that doesn’t result in income.

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If you do want to explore a new area in depth, there are ways to do this that will make approaching a new subject easier. There are many ways to start. Some people learn by reading. Some people learn by listening and watching. Some people learn by actively doing the thing they want to learn about. While any of these approaches can work when you want to learn a little about a subject, you will need to embrace all three if you want to develop a deep understanding of a subject.

Write as you learn

The important thing to do, as a writer, is to write about your learning process. Take notes about what you read and what you do. Record your story or book ideas. Express your thoughts as you go through the learning process. Doing so will put you ahead of the game when you start to try to make a living writing about the new area. Preparation always pays off in the end.

The reading approach

The quick and cheap way to start is with the web. Find blogs and other web sites that discuss the subject and read what they have to say. After that, you should invest in one or two well-regarded books on the subject. An introductory textbook is always useful, and they can often be found used through sites such as Amazon.com. See if the subject has any dedicated magazines, and subscribe to the most useful ones.

The watching and listening approach

Some people prefer to learn by watching and listening to others. People who like to learn this way should consider taking classes or purchasing video and audio guides such as documentaries and lectures. Apple’s iTunes store has a section called iTunes U which is filled with college level lectures on hundreds of topics. You can watch and listen to podcasts that are, for the most part, free. Another option available to writers is the interview. Find knowledgeable people in the area you want to learn about and interview them. This is a way to write and sell articles while you are still learning about the subject and will allow you to make valuable contacts in the area.

The action approach

The action approach is simple and direct. You learn by doing the thing you want to learn about. In many cases, this is the only way to truly get a feel for a subject. If you have never snowboarded, then all the reading, listening and watching in the world won’t make you a snowboarder. You have to actually go out and do it. If you want to write about something, you shouldn’t just do it. You should join groups of other people who do the same thing. Make connections within the community of people with similar interests. Embrace the activity.

Put them all together

To move beyond the basics, you need to use all of these approaches. Read about the subject. Interview people. Take classes. Listen to lectures. Join groups. Go out and get active. Just remember to write about it as you go.

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Focusing on your projects and your days

When you track projects as a freelance writer, you need to keep your eye on both the big picture and the details. On one end you have to keep track of deadlines and milestones. You must be able to report your progress to a concerned client or editor, and you must feel comfortable with your own progress. On the other side, you need to set your tasks each day, making sure that you are setting aside the proper amounts of time per day to keep moving forward on those tasks.

Setting an Editorial Calendar

On the big picture end, you should set up an editorial calendar. Your editorial calendar tracks all of your projects, both for clients and for yourself, on a weekly/monthly/yearly basis. For smaller tasks such as short articles or brochures, you may only need to track the due date and put a reminder to work on it for a date that is somewhat ahead of that deadline. For long articles, books, reports or web sites, you may need to break up the editorial deadline with milestones on which you intend to accomplish certain tasks such as a draft, a section or a chapter. The editorial calendar isn’t meant to tell you what you should accomplish every day. It is simply there to keep you apprised of the big picture.

Setting Daily Goals

On a daily basis, you need to set your short-term goals. These short-term goals can be managed by time or by task. If you use a time management approach, you might set a goal to spend four hours on Project A, two hours on Project B and two hours on Project C. If you use a task management approach, you might set a goal of 1500 words on Project A, write draft of second chapter on Project B and finish article for Project C. Either method works. A task approach makes it easier to set specific goals, but an hourly approach might work best for projects that pay by the hour.

Setting Priorities

It is a good idea to start the day with your highest-priority item. Distractions can come up no matter how organized you are, so try to get the important things done before any distractions have time to present themselves. At the end of the day, assess your progress and make adjustments to your schedule. Some days are better than others and you may find yourself ahead or behind schedule on a particular project. Reviewing your editorial calendar daily is a good way to keep yourself on track.

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