Vox Fortis Communications

First, a hearty thank you to all of you who asked where I have been. The last few months have been a blur, and something had to give with my time, which unfortunately wound up being my beloved blog.

The good news is, the dust has settled, and I have managed to budget my time in such a way that I can get back to this here thang.

Freelancing has been hard for me the past few months. I had one great month, followed by a scary-skimpy month in April. I cried. I felt like a failure. I actually started applying to full-time jobs, momentarily seduced by words like “steady paycheck” and “benefits.”

Here’s the reality, and to keep with the theme of my writings here, I’ll put it into internet marketing context.

If Google was indexing my life and my thoughts, and I punched in certain search phrases, none of them would return with “full-time job.” None. Well, except for “reliable pay” but that’s the only one. My keywwords would be things like:

Freedom to choose my work
Freedom to choose my clients
Ability to work from anywhere
Never working set hours

And many other things of the like. And you know what? Not one returned search term would refer to a full-time job. Even despite my frenzy for a few weeks, I couldn’t escape the thoughts that crept in…the ones that reminded me of all the reasons why I ditched my corporate job to begin with. Those keywords look something like this:
Cubicles
Micromangement
Petty, corporate sharks
Busywork
Glass ceiling

Which keywords do I want applied to my career? That answer is easy, even if sometimes the path isn’t. I had to let go of a client that just wasn’t working. It was a conglomeration of things, but suffice it to say that it was income that was hard to let go of. It made my April pretty paltry, which is what launched me into a “why am I putting myself through this” phase.

But I remembered why. I landed a gig last week that I’m rather excited about, should bring some steady income, with really fun people. It smacked me upside the head as I did some work this past weekend and took an hour off this afternoon to watch some TV. All those little things that I know I’d absolutely ache for if I was back to sitting in a car and commuting every day, sitting in a windowless cubicle and being beat over the head by upper management. I just don’t miss any of that, even if I miss the steady paycheck at times.

So, I’m back and re-rooting myself in the decision that being an independent contractor is best for me. Here I am, I’m digging my heels back into my blog and hitting “go.” The good news is, having a few months like this has refreshed the wealth of things for me to write about here, so I’m optimistically saying there will be no shortage of information, and no shortage of me hanging onto those keywords that got me here in the first place.   

I don’t know about all of you, but I never get to read all the stuff that’s in my RSS every day. It’s too crazy how often Lifehacker updates. I can keep up with the once a day posters, but my BoingBoing feed is a lost cause. I’d love to find some new blogs about small business, but I have no clue when I’d squeeze that into my day…somewhere between my phone calls where I’m simultaneously answering emails, maybe? Yeah. Not ideal.

A few weeks ago, Shane was all, “Pssst. I’m working on something cool.” So of course I’m all, “Your wife is pregnant?” Well, no. But until the human baby makes an appearance, he’d been putting intense work into another baby: Sproutwire.

I shamelessly love the Shane and Peter blog as it is, so I was intrigued to hear there was another project in the works. And it’s so genius, and created by a group that specializes in UI anyway, I’m just geekily excited to be in on the beta. The site is called Sproutwire, and it will serve as a hub for articles related to small business, vetted and served up to you on a gorgeous Sproutwire silver-platter-like-designed site every single day.

For people like us that can’t get enough reading about small business, this is a Godsend.

You know what else is a Godsend? ME. (I’ve always wanted to be able to say that.) As a reader of my blog, and because Shane is one of my blogosphere homeboys, you can get a sneak peek at the beta launch as well. Follow this link, input your email and you’re in line for when they lift the veil on the beta version this Friday.

See? You knew there was a reason you came here. So go. Now. Do I need to say it again? Go sign up for Sproutwire beta, fool!

Before we get to the second lesson in the puppy SEO series, I had an epiphany while I was traveling this past week about creature comforts.

I am pathetically addicted to electronics. Save for a novel of some sort, when I travel there are some items guaranteed to be in my carry-on bag (which won’t include anything liquid related thanks to the brain children of Homeland Security…I use expensive crap on my hair and already learned that lesson the hard way): ye olde Nintendo DS (with a copy of Yoshi’s Island or a Kirby title, since you’re curious about the levels of my immaturity), the iPod, and my laptop.

Of course, all of these things require electricity. And you know what? No friggin’ airline has the same way of providing power, if at all. I considered getting this, but then read up on the airline I was taking only to find out that basically….you get no power to your seat, fool. You will be confined to a 5-6 hour cross-country flight, sweating as your battery meters peters out to nothingness.

What does this have to do with anything, other than me being a high-maintenance nerd? I’ll tell you what.

Earlier in the week I met with a new group that has presented a really awesome partnership opportunity for me. Ironically, the president and I are alums from the same company, though at different times. He’s refreshingly together (you deal with enough business owners who have no clue what’s going on or what they want, and you appreciate the ones who have their act together) but at one point he said something like, “I’m sorry, I know I’m structured, it’s left over from corporate America.”

I never expect clients to do anything differently than what they’re comfortable with. It’s the creature comfort factor. Maybe I’m a flexible person by nature, but I’ve heard some horror stories come from clients about freelancers they’ve worked with. Yes, we all need to set boundaries from freaky extremists to keep our lives sane, but part of being in business for yourself means giving clients what they need and what they’re comfortable with. It’s a fine line, and you will certainly find employers/clients that will push the boundary.

Be reasonable. Don’t force feed clients things they’re obviously not comfortable with. Working with a lot of freelancers can make people who need your expertise feel like me when trying to find an airline power source: no two are ever the same, and they don’t want to spend money on something if it’s not gonna work. Being flexible and reasonable is something that takes practice and negotiation. Hopping a cross-country flight isn’t exactly part of my normal day, and it came sooner than I thought it would, but the bottom line was that a group I work with needed me to do it. It’s a group I thoroughly enjoy working with and am already learning so much from, so that’s a movable boundary in my world. They’re knee deep into a campaign, and didn’t want to run outta juice for their DS.

So, that was my mini-epiphany for the week as I grumbled my way through the headache that the world of travel has become. That, and in general, flying sucks…but I can’t think of a snappy way to equate to working for yourself, so this is what you get.

For more on being what your clients need, check out this entry. And if you still are liking what you see, subscribe to me.

I got in the car yesterday to go to the post office. As a regular community member over at BookMooch, I had a moocher who was waiting on a novel I’d recently finished. I live in an wee town in Virginia on the skirts of a metro area. This should not be any kind of production whatsoever…less than 5 minutes to the post office, tops. (Plus, I’m an impatient person, so…there’s that.)

I turned out of my development onto the main road where they were doing road work. Nothing big, one of those little buggy deals that punches squares into the asphalt (or is it concrete?) so they can insert the reflectors along the dividing line.

I sat and waited, and I started to get edgy. I watched the Highly Unnecessary Eighty Point Turn of the buggy, orchestrated by a construction guy who had originally stopped me by doing a hand wave while not even turned in my direction. He also had a walkie-talkie that didn’t appear to be getting any use.

Finally, I go on my way. On the way back, it was another annoying experience, but for a different reason.

As I drove toward the site, there was another guy there, but I saw a ray of hope in the situation because he had one of those tall signs. You know the kind “slow” on one side, “stop” on the other.

That’s where the hope ended, as I drove closer and could see him better. I was, by the way, driving closer because his sign had the “slow” turned towards my little car. Then I noticed his hand waving, indicating a stop….while not looking at me.

I stopped, utterly confused. Could I go? Was this a test? Was there a hidden camera looking to see how many citizens would just blow by? I looked around for an answer from the pine trees on either side of me. I looked back at the guy.

No eye contact, no nothing. I didn’t even know if he realized I was there. Maybe he wanted me to go but has a hand tic and I was going to make him feel bad by responding to that and not the friggin’ HUGE orange sign he appeared to be in control of.

As you can see, this was turning into a borderline existential crisis for someone that overthinks things as much as I do.

It’s also a really, really good example of your role with the clients.

You are the conductor.

Your client audience is looking to you for direction. They want a confident recommendation based on the expertise they’re working with you for. Don’t overwhelm them with choices or decisions on services they don’t know anything about. The best way to avoid that is to ask questions initially, and ask a lot of them. The key is to not ask questions about whether they want an email campaign or not. The key is to ask, overall, what they don’t have that they know they need. What struggles are they having? Don’t add to their pain, find out what it is and cure it.

Conductors serve more than just an audience.

They serve the musicians.

Whether it’s a client’s web page, their seo, their copy (or maybe all three) you will be directing the orchestrations that will make things happen. You’re the person that will stand there, conduct, and then turn to face the audience of your clientele, and it had better to be thunderous applause. If it’s not, it’s your fault. You can’t turn around, shrug, and say, “That tuba player sucks.”

The tuba player might suck, but it’s your job to keep that from the client and make him play better. That, or find another tuba player.

Don’t mix signals. In either direction.

Like my friend who had the “slow” sign in one hand the “c’mon, move it along” in the other, don’t confuse your clients. No matter what’s going on with the orchestrations behind the curtain of their project, convey what’s important for them to know. Give a reliable quote for the services they need (which goes along with the question asking I just kicked your tush over). If you assume they understand what everything includes, you’re in for trouble. Nickel and diming over things will confuse your client and could make them feel like you’re putting one over on them. Things like “Oh, I thought I was just writing your copy…it didn’t include any revisions or editing.” I don’t mean major, huge project scope changes, but things that should naturally come with any package. Deliver consistency so people will buy tickets for repeat showings.

Don’t overwhelm while trying to show off.

Although this is probably more apt to match with bands infamous for long, drawn out jam sessions that make some of us weep with boredom, I’m sticking to my analogy, dangit.

Remember, they hired you to do something they couldn’t. The more complicated you make it seem, the more horror you’ll see on their faces. Sure, if they ask to see the sheet music then show it to them. But don’t conduct, try and teach them how to conduct, make revisions to the sheet music…you get the point.

Keep practicing.

You’ll stumble. I guarantee you will. You’ll eat some costs and time you didn’t account for, you’ll work with bad contractors who are handling pieces of projects, and you’ll probably wind up firing that tuba player.

The good thing is, most people weren’t born like Beethoven. You won’t wave that baton and get perfection at first, but you will get more efficient every time you do it and will eventually be on the way to creating your own little masterpiece of a business.

In honor of the complete and utter neglect of my poor blog, I give you a photo of a jackass. That would be me. My promise to myself to stay updated got seriously sidetracked by some seriously crazy days leading up to the holidays and something had to give. Unfortunately, it was the task that doesn’t pay me money, which is coincidentally the one that can’t fire me if it’s neglected.Still, I’m a jackass for falling so far behind.That said, it’s time to get back on track. I spent the morning invoicing and catching up on also-neglected admin work. (Which um…I just got done saying my blog doesn’t pay me. My clients won’t either, if I don’t invoice them, but I managed to slack off on that too.)

To be fair, I haven’t taken days off in a long time. I went straight from corporate burnout to freelancing full-time, so I was bound to crash from the adrenaline of it all. Suffice it to say, I relaxed fully, enjoyed my holidays, but am totally ready to start getting my brain working again. Part of wiping the cobwebs off my brain included looking at where I’m at from a client and payment perspective.

I made the decision I seem to make a few times a year where I say, “Well, I’ll go ahead and cancel my membership at Guru.com.” Like clockwork, it gave me a reason not to. Let me first say that I recognize most people don’t have great things to say about freelancing sites. I’m in another camp, but I also think I use it differently. The people I see getting most frustrated are the ones that try and pin their freelance money-making entirely on sites like Elance.com and Guru.com. When Elance overhauled its structure last month, a lot of contractors were rightfully very upset because really, no matter how Elance wants to spin it, the providers were getting screwed and not the buyers. (Catalyst Blogger’s update can also be read here. I have to give shouts to a fellow Philly-native, of course.) I personally never had luck with Elance, so I’m in the Guru camp, but I can completely understand why they’re upset.I use freelancing sites for specific reasons, and I think they’re beneficial if you apply the tenets we all know as freelancers. I see these tenets get suspended when it comes to these sites, but they have to be treated like any other marketing channel. Here’s what I mean:  

Don’t put all your eggs in one basket. 

This is common advice among freelancers, business owners, and contractors. Do not tie yourself too heavily to one client, because if they go out of business, guess what? You might, too. Keep a constant and spread-out roster so you are self-sustaining. Places like Guru.com and Elance.com are no different.”But Susan,” you say, “I attract many clients by using that one site.” No, you really don’t unless you’re evolving them into longer-term relationships that can stand on their own outside of that site. The best illustration of that is the changes Elance made. You might have 100 potential clients on there, but because Elance changed, now you might not if you don’t want to pony up what I believe is a ridiculous amount of dough. In that way, you are putting your eggs in one basket because you’re relying on a single conduit to get you in front of those clients.

 Don’t bid on a job. Quote it.

This is a mentality thing that you might have to work at. I read a lot of “when I bid on a project” talk. Yes, in the site’s world, you’re bidding against others. But the minute you do that, you’ll start to lose. You cannot worry about what other people are bidding, because all it does it tempt you to get into a price war.

Don’t think of it as bidding on a job. Think of it as providing a quote to someone who is interested in your services. Every job quote I provide is what I’d quote anyone for copywriting or marketing…it isn’t less because of the medium I do it through. Sure, I probably don’t get a lot of jobs because of my price compared to someone in a third world country but I don’t want the job anyway if it’s not going to pay me my going rate. I don’t go on there and bid on every job. I’m selective, and trust me, you can usually tell on the job posting if it’s worth trying or not. Apply the same standards you would to any job you’re interested in.

Build repeat business.

When I was first starting out freelancing, I accepted small, one-off jobs because it was just supplemental income anyway. Nowadays, I scan through latest postings quickly if I have some time I could fill, and I only quote a job if it’s obviously something that could lead to a longer-term relationship.

Two of my favorite clients are groups I found on Guru. The one plainly said it would be a long-standing project management role. The other was for blog writing, but the client and I get along so well that he’s giving me a HUGE project that he trusts me with. He gives me stuff every week, and is one of the easiest people to get along with I’ve ever met. My project management client that I mentioned now trusts me to do more hours, and has started letting me flex my muscles in the area of SEO reporting and PPC as well. It’s amazing what can come from working consistently with people you like.

These are the basic things I apply to any client, no matter if they come from a site where you pay to gain access to job listings or not. Obviously, it’s worth the $80 or so per quarter to find that one diamond in the rough for me, because I get way more business from them than pays for the membership there. I also get invited to quote many projects thanks to my rating and portfolio information on there. (I rarely accept those, but occasionally I’ll throw my hat in the ring.) It was a good reminder to me the other day when I came on a writing listing for a company that looked promising. I quoted my hourly fee, and they responded with wonderful examples of what they’d need, and the fixed price was way more than fair for the work involved. They were polite, buttoned up, and obviously concerned with quality and not getting the cheapest person they possibly could. It was a good reminder that it’s a viable marketing avenue for me.

But, it’s not the only one. And it shouldn’t be your sole avenue of jobs, either.   

As much as I love my gadgets, I think it’s time to admit that I’m really old school when it comes to planners. There’s something about paper for me. The ability to easily flip through pages, erase, and see myself writing down a task that sticks in my brain, maybe.

Sometimes it’s not easy to come to these conclusions. They come at random moments, where you have these epiphanies at 1am, your tongue slightly sticking out of the side of your mouth, gripping your mouse and squinting at the screen to get the little appointment box to drag to the right time on your calendar, for instance.

Not that I’d know anything about this.

Working for yourself and managing your time is more challenging for some than others. I always get my stuff done, but I know I could do it more efficiently. Enter the paper planner crutch. Things like that you can control, but no matter how much you like to think you’re completely master of your own schedule as a freelancer, your days do have some pull over what gets done when.

How can you make this work for you without ripping your hair out?

1. Be honest with yourself.

There’s nothing wrong with admitting you totally suck at time management. There’s also nothing wrong with bragging if you’re great at it. Either way, this is a conversation you only have to have with yourself. (Not out loud. At least not with others present. Those that abandon the corporate route tend to get enough funny looks as it is.)

You need to figure out where you are when it comes to strengths and weaknesses in time management, and sometimes that takes a little pain. Take stock every so often of where you’re at, if possible. Are you sweating at 2am every other night of the week to hit a deadline? Are you finding that your days feel like a lot of reacting without a lot getting accomplished? This is the bigger picture, but once you start noticing your own patterns it will tell you a lot about where you’re dropping the ball. Maybe you have no clue how to say no to someone. Maybe you are always regretting the two hours you spent on your Xbox 360 instead of getting the x,y,z done. Odds are good that whatever gets you into time crunches, it has a consistent root cause.

So be honest about it. Don’t kick your own ass over it, but acknowledge it and figure out how to co-exist with it.

2. Figure out a solution.

For me, I sometimes have a hard time figuring out when things can get done by. I originally used my planner for scheduled calls and things of that nature. But, you know what? There were a lot of blocks being unused. I’m training myself to pencil in time for each project’s tasks (thanks to the life-saving to-dos and milestones I set up in Basecamp) so if someone says, “When can I have this?” I can easily glance and see how much time is already blocked off for other stuff.

Whether I actually work on it during that time, I’m finding is irrelevant, at least for me. I adhere to it as best as possible, but I’m finding it immensely helpful just to have a visual of what time is already committed to stuff.

Whatever your weak point is, accept that. It’s ok if you can’t change it, just figure out how to co-exist with it peacefully so it’s not obstructing your productivity or your client’s happiness.

3. Implement.

It’s hard to break a habit. It’s hard to start new ones sometimes, but critical to your success is your ability to manage YOU. Working for yourself will teach you things you never knew, but that doesn’t mean squat if you don’t grow and become a better professional for it. Put on your big-person dungaroos and go for it. Your clients, stress level, and coffeepot will thank you.

The past week taught me something, but I didn’t realize what it was until I was drinking coffee this morning. (Has anyone noticed this is where a lot of my entry ideas are spawned from? This is no accident.) The coffee wasn’t our usual brand, a fact I only mildly noticed while I was grinding it and muttering to myself.

Earlier this week, one of my clients and I realized we really needed to get some more resources on board. As her project manager, this was obviously something I was all for, because the squeeze was on our resources big time and I was sweating looking at the to-dos that had no contractor to call home until their completion. We put up two ads, one for a copywriter and one for an SEO person. Being on the “employer” side of that spectrum taught me a lot of things. These things have probably been mentioned a lot by other bloggers, but I didn’t get it until I saw it for myself. That said, here are things that hit me in the head like a two by four. (Which may be related to the caffeine headache, as the coffee is still brewing.) Granted, finding and applying for gigs can feel like a battlefield, but while you’re donning your helmet and kevlar vest, here are some magic bullets that I learned being the side of the place that needed a person and posted the ad.

Form letters are horrific.

These things really suck. Don’t use them. Please. First, it’s obvious that you didn’t remotely read the job description. You cut and pasted the same thing you sent to everyone else and hit “send.” Why would I want to get in touch with you? I know it saves you time, but as a contractor, you’re really in a service industry so it’s not about YOU. It’s about THEM. Don’t be the Paris Hilton of job ad response.

Get to the point, already.

This is actually a huge thing I noticed with the form letters. Long responses. I mean…scrolling and scrolling. Maybe this depends on the employer, but I can tell you that there’s no way I’m reading that. I’m glad you have a lot of experience, that’s very valuable. But it’s not valuable to list that you worked with Microsoft and then also mention you did SEO for Al’s Auto Parts. Who cares? If you worked with Microsoft, that matters. Al’s, though I’m sure was a great client, doesn’t matter under the shadow of a bigger company.

And if you’re writing 5 pages and it’s a form letter, you’re toast. It’s obvious in the intro that you didn’t read the job ad to begin with, yet you’re expecting me to read 5 pages about your glory? Mmmm….don’t think so.

Oh, and…just because you insert our name in the “Dear blah blah blah” opening and have things like “We would be pleased to speak with you about your [job ad need].” and then go one to talk about stuff not remotely relevant…that’s a form letter. I don’t care that you read enough of the ad to put in a name and what we were requesting. You don’t get partial credit for that.

What does the employer care about?

Ok, some job ads really don’t answer this well, at least in any obvious way. Some have a neon sign that screams, “Cheap person who doesn’t care about skill.” Unless you’re desperate for money, and some of us are around the holidays, keep moving. Potential clients aren’t going to show their hand in the job ad, but you can look for clues.

Did they ask for samples? Did they ask for references? If so, they care that you’ve done what they’re asking for. Pick two solid examples (Microsoft examples, not Al examples) and blow them out.

Did they ask for specific skills? It amazed me how absolutely clear I made the job description, yet people didn’t respond with experience at all related to it. Touch on the specifics of what they asked for. If you’re just ITCHING to tell them about something else, go ahead, but do not forfeit responding to their specific needs just scratch your own itch. If they want keyword research, give examples….and if you happen to write SEO content, YES mention that. But don’t talk about writing content without telling them you can do what they actually asked for in the first place. This was rampant in the results I saw. I had to get in touch and ask specific questions….questions which were, by the way, in the job ad to begin with.

What does this have to do with coffee?

My coffee this morning was great. It wasn’t the usual brand, but I didn’t notice. Know why? Because all I cared about what that it was halfway decent and stripped away the Ultimate Grouch Aura I have first thing in the morning.

Employers want what they want, and some things matter more than others. They might not care if you’re Starbucks or Folgers, but they want you to work in their coffee maker. Others might totally care if you’re Starbucks, and they’d be willing to pay for it. Figure out what they want and appeal to that. Don’t spend your time screaming about how you’re Folgers if their job ad made it clear they don’t care. You’re wasting your time, and you’re showing the employer that you don’t care what they need, just about what you can provide.

And in the end, you still won’t have helped their Ultimate Grouch Aura.

I’m non-grouchy 99.9% of the time. Subscribe and you can see for yourself.

One of the benefits of being entrepreneur is that you can decide how much or how little you want to work. You are the lucky dog who has a modicum of control over how much you’re making. (Assuming you’re landing jobs, of course.) But there is a huge limitation that us workaholics actually get visibly irate about: there are only so many hours in a day.

I can work 18 hours straight, because what I do rarely feels like work. I love it, I enjoy it, and all that huggy yummy stuff. Since I don’t want to make you feel motion sick, we won’t dwell on the yummies. Instead, let’s focus on those people who have managed to ride their entrepreneurial rollercoaster, and finally get over that huge, slow, crawl to finally hit the peak and take off rushing at a million miles an hour. This has been all around me recently, mostly notably with my friend Naomi who has now exploded onto the freelance scene thanks to her entry that pitched a tent on the front page of Digg.

As much as I love my work, there are only so many hours in the day, like I said. If you’re doing well, you can fill those, but how do you get to that next level? How do you manage to grow your deserted island into a little village full of natives? (Not like the ones in King Kong. If those are your natives, you need to consider exile.)

People that have managed to step off their island and grow it into a village have one of two ways they’ve managed to do this, aside from the fruity drinks with the little umbrella. (Those never hurt, but you’re more likely to get tourists than villagers that way.)

Way of the Solo Warrior #1: They are good at multiple things.

I fall into this category at the moment. My mind makes connections to stuff, especially business capability. I started in sales, and got interested in consumer behavior, so I landed in marketing. I always loved writing, so I took a job writing for consumer experience, which just so happened to be in the e-commerce division of a major retailer. That environment immersed me in how things work in the web world, and being an organized and pretty focused person, my skill set grew in things like managing projects and campaigns. I started digesting online marketing information and it made sense to me, so I grew into an online marketing role.

Here’s my point. Maybe having skills in underwater basket weaving and survival skills in the desert aren’t going to be a solid offering. But, if you can find related areas to what you do that you’re naturally good at, you’re increasing your skillset. The clients I work may only have little ol’ me, but I can write, market, do analytics, and manage projects and campaign strategy. Having that combo has proved to be pretty great, which is something I never would have thought. I read so many things about how you have to focus, capitalize on the whole Long Tail thing, and mostly wound up feeling like a scattered person who wasn’t sure what to offer.

I started offering up all things I was good at, and it’s worked well. I haven’t hit that all-important pinnacle on my roller-coaster ride yet. I’m still climbing up, but I think if keep plugging at it I’ll be plunging forth and looping upside down in no time. And, I do offer the fruity umbrella drinks, but the natives that seem keen to hang on my island for awhile stay anyway, so that’s kinda nice of them.

Way of the Solo Warrior #2: They have people that can do what they don’t.

Let’s say you’re really only good at one thing, and you know that. That’s absolutely awesome. I love to have people around that know one thing, but they know it so well that in my mind there’s no other resource on Earth who can possibly have half their knowledge in their puny little brains. Plenty of people make a great living doing this one thing they’re good at. The people with the grass village on the deserted island tend to have a network.

They mingle with other people that have a skill set that would complement theirs. There may be zero interest in learning what the other one knows, but when people know what they don’t know, they’re a force to be reckoned with. Seeking out those who know what you don’t is a valuable way to spend a little time each day. You never know when you’ll have a client that loves you so much they don’t want to use anyone else…even if they’re asking for things you don’t know how to do. Guess what? If you know someone who does, then you DO know how to do it by proxy. You have a person you can refer (if they’re not a jerk) or you can sub-contract out to (if their work doesn’t suck, no matter how much they know). You = rockstar to your client.

There are many other things that play into when and how your wee little business takes off, but these are the two I run into repeatedly. Feel free to share the others.

Speaking of building an island, feel free to join mine. We have frequent bonfires and roasted marshmallows.

I’ve been freelancing for years, but only have a few weeks under my belt doing it full-time. I started plugging away when I was a writer churning out stuff in a cube, at first for some extra income. After a few months I realized something crucial:

 I liked it.

I really liked writing newsletter content for dental practices one moment (so not kidding) and then helping devise e-mail strategies 5 minutes later. As an extreme multi-tasker who gets bored easily, having multiple clients was a natural fit for me. In the past year, things really started falling into place for me at a time where life was turning into a pressure cooker. New house, new job, finishing my MBA, and new freelance clients every other week. I could feel the squeeze, more and more every week. I knew something would have to give and I’d have to make a decision. That decision wound up happening suddenly a mere few weeks ago, and now that I’ve had time to reflect on pre-freelancing life and in-the-thick-of-it-pulling-up-by-my-bootstraps, I’ve come to some reflective conclusions.

Let me enlighten you as to what it’s like for me to make a decision about big things like this….it’s a humdinger of an experience. I’m an analytical person by nature, so first there’s the mental listing of every possible scenario. Then each of those has what ifs, which branch off into others and…you get the idea. Tailspin central. I’d look at freelancers that were doing it, and wonder, “How’d they KNOW?”

Here’s the thing, which is really freaky for any of you that think like me: You don’t know. It’s probability, not a proven science. There are certain factors that you weigh, and depending on whether the “yes” or “no” is heavier, you can use that. Which factors is probably the next question, and there are too many to list, even for me. But here are some biggies:

1. Do you have a client base built up?

If you’re mostly finding one-shot projects on bidding sites for peanuts, the heavier answer here for you is “no.” In that case, don’t quit your day job to sweat week-to-week. You’ll always sweat some as a freelancer, but steady clients are your deodarant.

2. Are you constantly underselling to land a gig?

If you weigh heavier on “yes,” then you need to stop it. Unless you’re totally without experience (and you shouldn’t even be considering making the jump if you’re in that camp anyway) don’t be cheap to land a gig. IttyBiz has a great explanation of why that I won’t even try and duplicate. If you’re finding clients that are paying a rate you’re not wincing over, you’re on more solid footing here.

3. Does it feel like your freelancing is getting in the way of your day job?

If the scales tip towards “yes,” then you might want to decide if freelancing full-time is what you want. If it feels like a nuisance and you have a problem being self-motivated, those are huge hurdles to overcome. This brings up the opposite, however…

4. Does it feel like your day job is getting in the way of your freelancing?

If so, maybe this is where your loyalty really lies. If you’re more interested and it doesn’t feel like work when you’re working on your clients’ projects…that should say something. ‘Nuff said.

5. Can you make enough to get by at first?

Even with a steady client base, you will struggle the first few months because you don’t get paid regularly. Plan for this. It’s feast or famine, and there’s not really any two ways around that. If you have the aforementioned steady clients each month, that certainly helps. If you’re not sure that you’d have enough for a can of beans and Saltines at the bare minimum, you have to crunch numbers. I know, it’s not fun, but you’ll thank yourself if you’re realistic. Try this calculator from Freelance Switch…it’s very eye-opening.

I was at the tipping point for my threshold of stress and work. Something had to give, and I had a lot of support in the decision which made it an easier one, but no less scary. You have to be intrepid, you have to be out there, and you have to be willing to take rejection and share your opinions and recommendations over and over again.

It was the best choice for me, and you’ll know if it’s something you really want. There’s no perfect moment, no matter how much you’d like to plan it…there’s just the probability of success. Stack the odds in your favor.