The Little Freelance Handbook

On creativity, dealing with clients, and the nuts and bolts of freelancing.

By Andy Newman


A little over a year ago, in late 2013, this started as an ebook. I sold a few copies at $1.99, but never enough to collect a commission from Amazon.

Truthfully, putting this together was never about making money. Pitching a short book to a niche community like freelancers who have various levels of success—and therefore, various levels of income—was never a solid business plan.

The idea of a book was really just about delivering in a way that made sense. Today, this seems to make more sense. You can take it, leave it, or bookmark it for later. It can grow, expand, and contract as it makes sense.

This is a short collection of lessons I’ve learned as a freelancer. In many cases, I refer specifically to my primary area of expertise — filmmaking and online video production — but in most cases, where you see the word film or video, you can simply replace it with photography or design or writing. Even with the unique skills we each possess to become an expert at something, it turns out that a lot of the lessons you learn as a creative are universal.

The Little Freelance Handbook assumes you’ve already made the decision to become a freelancer. Only you can decide if it’s right for you, your family, and career. You’ll be making a lot of stressful decisions as a freelancer, and hopefully this can serve as a second perspective and set of experiences for you to reflect on when you need a fresh look at a situation.

It’s written in a way that you can jump around to whatever topic you’re interested in at the time. There is no overarching narrative other than the freelance journey itself. Share something you find interesting with a fellow freelancer. If you ever have questions or comments, you can reach me on Twitter at @andynewman or here.


A positive customer experience is key.

The first thing you should be focusing on as a freelancer is providing an outstanding customer experience.

It’s simple.

Listen to your customer.

Even if they don’t think they know what they want, they will tell you everything you need to know.

It can be tempting to talk a lot during the early stages of a project. A prospective client who doesn’t know what they want or need — what better way to sell your services than to show off your knowledge.

That’s the worst thing you can do. In most cases, your words will sound like gibberish. In other cases, it will actively make the client feel stupid or overwhelmed. They’re coming to you because you know this stuff — because you’re the expert — not for a weekend course on the topic.

Just listen.

When you need to, gently nudge the client in the direction they need to go. Give them options when you can. This is where you can start explaining the options in more detail, now that they know what they’re looking at.

And keep in mind that sometimes the right answer is that the client doesn’t actually need your services at this time. If you don’t sell them on something they don’t need, they’ll often come back to you when they do need it.


Got it. So, what should I charge for freelance work?

Everyone’s first question is some form of the following:

What should I charge?

What am I worth?

How do I begin to figure this out?

(You’ll continue asking yourself those questions for years to come.)

If you’ve done any research, you’ve realized that there’s not one right answer. A combination of what you do, your skill level, and your client all make up an ideal rate for a project. That’s going to be true as long as you’re a freelancer.

Start by thinking about an ideal hourly rate.

Maybe this is where you’re stuck. That’s ok—we’ll work through it. Start by considering this: How much would you like to reasonably make?

If you’re just beginning, follow your gut. It may sound counterintuitive, but it’s true. If you’re happy with the amount of money you’re bringing in, that’s a wonderful start.

If $50 an hour seems too high for the work you can deliver, maybe it is. If $30 an hour seems a little low, again, it probably is. You have to consider this—you’re no longer getting health benefits; you’re not guaranteed 40 hours a week; no sick pay or vacation time. And don’t forget taxes, which as a self-employed person, you now have to pay more—possibly around a third of your income.

What is your bottom dollar? If someone hires you for $20 an hour, booking 50 hours of your time will only cost them $1000. Charging too little will sink you. You’ll get bad jobs that will take up too much time. If you’re dedicating all that time to one underpaying client, you won’t be able to pursue other work, take on new projects, or have any time away from work.

Any number you land on should serve as your baseline. Once you get a feel for how much time you’re putting into work and how much money you’re coming away with each month is when you can make a truly informed decision on how much you should charge.


If you’re consistently getting work and you’ve improved along the way, don’t be afraid to increase your rate. After a year, give yourself a raise just like any other job. If you’ve stuck with freelancing for a year, you’ve definitely learned a ton of lessons and become more skilled at your craft.

Now seems like a good time to mention this: You might make some mistakes on your first few projects. We all do. You may charge too little, or they may just not turn out very good. That’s nothing to be afraid of—it happens. But on the other hand, if it feels like you are being taken advantage of, you probably are. The best advice I can give in those situations is to wrap up any projects and go your separate ways.


Next, think about your skill level.

This is the big question mark, especially when starting out.

How good am I?

Can I do what they want?

You should have some idea of what you are capable of and what you can deliver. Like I said, you will make mistakes—but you should also be learning new things along the way. You will have some projects that won’t go as well as you had hoped, but hopefully that’s a very small number in comparison to the bigger picture.

Your skill level is the single biggest factor that will increase your rates. If you don’t feel like you possess a high level of skill yet: Go make something.

If you’re a web designer, come up with some personal projects you want to pursue, or make a website for a friend or family member. If you’re a videographer, make a short film with your friends, or go find someone interesting and film an interview. If you’re a photographer, you have no excuse to not be taking pictures every single day. Make mistakes on these projects so you’ll make fewer on the big ones.

When you start doing that, you’re able to put better projects in your portfolio, and by extension your value becomes more obvious. Sprinkle your personal projects in with some client work and you’ll soon have an impressive body of work.

Bigger companies and opportunities will come calling.

If you’re not sure you’re ready for freelance work or don’t feel like you can charge a fair rate yet, personal projects are even more important. Do as much as you can to improve your skills. Read. Consume work from those that inspire you. Get involved in communities built around your craft.

As you get better, people will start noticing your work. Maybe a successful freelancer will bring you on to help out with their project when they get too busy or need more help. I’ve done this and it’s how I got my start. This creates relationships and suddenly you have someone you can trust who you can just ask: “Hey, what should I be charging for this stuff?”

Finally, think about charging a flat rate.

When I do freelance work, I like to book projects at a flat rate rather than hourly. This can be a rate per day or for the entire project—usually that’s your call, but sometimes the client may have a preference.

One reason I prefer flat rates is that it’s much simpler. As you take on more work, you’ll get a better idea of how long it takes you to complete a task. You’ll also get better as you repeat those tasks and come up with systems for your work. You shouldn’t be punished for working quickly—after all, your client should be paying for your experience as much as the labor of your services.

How do you charge a flat rate? Estimate how long you expect a project to take, including things like meeting times, travel, and revisions. Come up with a number based on your comfortable hourly rate multiplied by the total time you expect to take. Add a little cushion in for unexpected costs (and you can refund this if you don’t need it—that will impress your client).

If you do this, suddenly you’re no longer tracking every minute in a spreadsheet or on paper. There aren’t questions about whether or not phone calls are charged by the hour, or charged at all. A 15 minute phone call might not seem like it’s worth charging for at first. If your client makes six 15 minute phone calls over the course of a project, that’s suddenly an hour and a half of your time that went uncompensated.

Another advantage of flat rates: It’s easier to manage your schedule. If someone hires you for 20 hours of your time, they may need two hours a day for the next 10 days. Or, you could say 20 hours is two full days or four half days, and that you’ll exclusively work on their project between these times.

I’ve found this approach to be really helpful during the revision process. When I say, “Ok, I’ve blocked off 10 hours on Tuesday to make any necessary changes, I’ll need all your feedback by then,” things are much more organized. The alternative can be ugly: Adding one bit of feedback on Friday, get more on Monday, add it, more on Wednesday, and so on.

In the end, you might be making what you made if you charged hourly. Occasionally, you’ll make less. This can suck, but it happens. The lesson here is to be very clear up front about your services and terms. Usually this happens when tasks continue to be added to the project, it wasn’t represented correctly, or you just miscalculated. The first two issues can be resolved with a clear contract. The third, you’ll just have to learn for the next time. To avoid this as much as you can, be clear not only about the terms, but also what any extra charges may be if, for instance, there is an extra set of revisions. As long as the reasons for another round of revisions aren’t your fault, the client should understand that it’s outside of your original agreement and be ok with paying you for the extra time.

The magic with charging a flat rate, though, is that on some projects, you may make more than your normal hourly rate because things went smoothly. That’s great, because if things went well that means the client should be thrilled. Guess what? They no longer care if they just paid you above your average hourly rate. You totally wowed them.

So, what to charge?

Sadly, there is still no exact answer. Hopefully I’ve brought up points you didn’t consider, or maybe didn’t consider strongly enough. Like with all areas of freelancing and creative work, a large part of it is following your gut and listening to your head.

You already know more about freelancing than you think.

If you keep thinking you should be making more money, you probably should. If you’re afraid you can’t offer good value, you may want to proceed with caution.


So, to sum it up:
Figure out a good hourly number. How many hours do you want to work to make a living? Figure out how many projects you can reasonably take on, and be smart about scheduling out your time. Improve your skills, hone your craft, and maybe even focus in on a niche market. As you can better serve your clients, you can ask for more money. It’s a process, and with some practice, you’ll figure out what works for you.

Disclaimer: I shouldn’t have to say this, but here it is anyway. If you need financial or legal advice, you should always seek out a trusted, professional financial advisor or lawyer. I am neither. I am simply sharing some practices that have worked for me as a freelancer.


Thoughts on inspiration and creativity.

One of the unique challenges of freelancing is the requirement that you must always be creative.

Whether starting a new project or dealing with a client that wants to see multiple options or concepts, you have to be able to ideate at the drop of a hat. Perhaps the area where this is most commonly noticed (though it happens in every field) is with writing. The dreaded “writer’s block.”

Some theories say that there’s no such thing as writer’s block. Writing anything, even nonsensical gibberish, will allow you to eventually push through anything that may block your path. Whether that “advice” is actually helpful to you or not is questionable, but there’s one piece of actionable advice that I’ve found works wonders for me.

When writing a screenplay for a film, it’s very easy to get stuck. You’re creating characters, a world, and a story, all to communicate some message you have in your head. The advice I heard that’s stuck with me most is: Write the worst possible scene you can think of, then keep writing. It may sound simple, or silly, but it works. It’s harder than it sounds to write a truly terrible scene; even casual movie-goers have better taste than they give themselves credit for. But it keeps you going. You build momentum. And throughout the rest of the process, you start thinking of little ideas that make that bad scene better. You, in effect, push through it.

Creativity is no different.


Inspiration is everywhere. Sometimes it takes awhile for the dots to connect, but if you keep consuming, if you keep your momentum, those dots will connect.
Often when you least expect it.
Keep a notepad handy.

Is that why creativity is expensive?

The following section is more for your clients than for you. I’m including it because it may help you contextualize or verbalize certain points when a prospective client pushes back on price.

In short, don’t discount your prices—learn how to better communicate your value.


Creativity isn’t expensive. Including when companies spend a million dollars on a thirty second commercial. It’s all about value. If you don’t consider value as your top priority (or as the producer can’t communicate value), the numbers really don’t matter. Value can be had for $1,000 or $1,000,000 depending on your situation and perspective.

But to talk about some details for a minute, video production is very similar to photography. Especially in today’s world where many videographers often shoot video on a DSLR, a lot of the equipment and costs are the same.

Here are some things to consider when budgeting a project.

The camera. That’s the most important thing, right? A quality, professional camera is going to cost, at minimum, $2,000–3,000. Many production companies and individuals who can afford it are moving to high-end Canon or RED cameras. They can cost the equivalent of a new Honda Civic (or more).

You can get by on less. I did for awhile. Eventually it will catch up to you, usually at the worst possible moment.

The lights. Lighting is the single most important thing in making a video look great. To get a professional kit, you’re looking at another $2,000 or more. There are lights for photography that can cost over $10,000 a piece. Crazy, huh?

The audio. This is actually the most important thing to a great video. Wait, did I just say the camera, lights, and audio are all the most important things to a great video? (Yes.)

A basic audio setup with a professional grade microphone and recorder is another $1,000. If you want to get wild, well, the sky is the limit.

The people. The people! They are the ones you’ve hired, now that you mention it. It’s their years of experience that you’re relying on, the mistakes they’ve made in the past that they won’t make again, their efficiency, resources, quality, and creativity. They’re the real secret sauce!

But before they can even walk in the door, they need that experience, and all the equipment listed above. And batteries, memory cards, lenses… you get the idea.

The time. The big multiplier in the equation. A small production can take a team a half day. Other productions may require much more time. And what if there’s travel? Then equipment and people need to be shipped all over the place in safe little containers like Pelican bags and airplanes.

After the production is complete, on to post-production. The editor can spend anywhere from a single day to weeks importing, organizing, syncing, editing, color grading, adding graphics, exporting, revising, exporting, revising, and exporting again. All on a computer powerful enough to render high definition video and software ranging from hundreds to thousands of dollars.

This isn’t to say a good video needs to cost $20,000. Quite the contrary. The point is those budgets exist, and are often totally justified. The key is to recognize and respect all the components that go into a production to determine its true value.

If the goal is to attract new customers with your video or to remember your wedding day forever, consider the true value that represents to you. If you expect or hope to increase your revenue by $100,000 by creating a great video campaign, maybe it’s worth investing $10,000 or more into the project. If you want a wedding video to show your grandkids in 40 years, don’t you want something you’ll be proud to share? Your flowers and cake will be long gone by that point.

To prospective clients: Don’t be surprised if you contact someone and their rates are much higher than expected. They wouldn’t be asking that much if they weren’t confident in their abilities. They know the value they have provided previous clients. Chances are, if you want to hire them, a lot of other people do, too.

We also won’t be offended if your budget just doesn’t match our rates. Just don’t ask us to sacrifice the quality of our work in order to get a discount. And never ask someone to work for free. We value our time as much as you value your own.

The point here isn’t to talk down to anyone. It’s also not about trying to nickel and dime a client. The point is that there is fair value for everything. What you can afford may not match up, so it’s a matter of determining what is most important to you.


Feedback isn’t always fun, but it’s important.


Whether you work as a freelancer or not, dealing with feedback is required. This is how I deal with what many consider to be the worst part of the job.

  • Read the feedback, then take a break. It’s not easy to be directly critiqued for work you poured your heart and soul into.
  • Distill the feedback down to the most important five or six pieces. That’s not necessarily, “Clean up the audio at 0:34.” I’m talking more like, “Replace the music.” Important in the sense that your average viewer would notice the change. If you need to make more than a handful of substantial changes, something else is probably wrong.
  • Rewrite the feedback in your own words. Now, when implementing any changes, you’re not re-reading any tone or attitude the client may have had because their lunch order was messed up that day. You also don’t have to be reminded of a minor suggestion that doesn’t actually need to be followed.
  • Remember that the truth usually lies in the middle. What you originally created wasn’t perfect. Even Hollywood screenplays and films go through multiple stages of edits and revisions. Take what you saw from the original vision, the feedback you have received, and then decide what’s important. That’s really where your value lies.

You make decisions that will be the best for the project—not because the client said so, or because you made it that way and you like it.


Remember: Take everything with a grain of salt, realize that your work isn’t perfect, the client isn’t perfect either, and use your expertise to make the best decisions for the project.


Please, don’t compete with fellow creatives when there’s no need.

Why is there so much needless competition amongst creatives?

I always try to bring new people on, much as I wish more people would have done with me when I was starting out. If I can’t (or don’t want to) do a project, I always pass on at least one referral.

It’s frustrating when—and this has happened to me multiple times—fellow creatives pull the rug out from under you by offering free work. I would have gladly brought this person on as a paid assistant or let them hang out at any shoot they wanted. Instead, they chose to be my competitor.

And when I am too busy to tackle a project myself, will I ever work with this person or pass a referral off to them? Nope. I’ve made friends I can share work with, not competitors.

The client, while briefly feeling great about their free work, ultimately was short changed in the quality of what they put out to represent their brand.

There is a time and a place to offer free work, and I know how tempting it can be to “build your portfolio.” Don’t do it. Anyone worth your time and your expertise should be willing to pay you. And not with exposure. If you’re looking to build your portfolio, work on your own projects. Build your own website, make a short film, photograph some friends. Offering free work as a “professional” only brings down those around you, and people do notice. You’re either pissing off other creatives or making businessmen and women salivate at the idea of taking advantage of your talents.

Back in 2012, I put together a list of freelancers I recommended in Columbus, Ohio and shared it on my blog. The list included other videographers. Trust me, I get more work from being these people’s friends and trusted ally than I would by trying to snipe their projects. It’s not worth it. Be kind.


First year of freelancing

I wrote this essay exactly one year after I started freelancing.


I officially started taking on paid video work in September, 2011. I was working freelance on a part-time basis, mostly editing projects. In February, I made the jump, quit my full-time job and started freelancing full-time.

It’s been great, mostly. I’m deeply grateful for everyone I’ve had the chance to work with — good and bad. I’ve grown more than I can put into words and learned a lot about myself, business, and my passion.

But I want this to be about more than just how great everything is, because it’s not all sunshine and candy. Working from home and being your own boss comes with as much bad as it does good, and I want to reflect that.

I’m not trying to scare anyone away from chasing their dreams, in fact, the opposite. Overall, this has been one of the best decisions I’ve ever made, I’m much happier, and I’m getting paid to do what I love.

In the end, I believe successful freelancing comes down to one thing: Balance. It’s just as important to respect and learn from the bad things as it is to put all your energy into the fun parts of the job. These are some of the lessons I’ve learned, and some things I even need to remind myself from time to time.

The good and bad of working from home.

The hours you work are totally up to you… mostly. Until you get a client that’s a morning person and calls at 8 am, and have another that’s a night person and respond to your email at 1 am. The important thing here is to clearly set boundaries as to what works for you early on and stick by it. I don’t care when someone contacts me, as long as they understand to expect a reply during my general working hours. Depending on your field, your hours may fluctuate. A photographer might shoot all day on a Saturday, or a night owl web designer might prefer to get work done when the house is quiet. Either way, it’s critical to communicate when and how you can generally be reached.

Working from home can be lonely. For me, that’s actually been a good thing. I love my alone time, as I’m an introvert by nature. Not answering to anyone else or having someone stare over my shoulder while I work allows me to work in the way that best suits me (in my pajamas). But when you stop showing up to the same building everyday to work on the front lines with your co-workers, you will almost inevitably drift apart, no matter how hard you try. Setting your own hours is great until you try to meet up with old friends and realize their lunch break is at an odd hour.

Overall, this freedom has been an amazing break and change of pace for me. Some days you might put in 14 hours of work, and others you get to schedule a half day of work to spend more time with your family.


It’s all about balance.


Dealing with clients.

You have to have healthy lines of communication. Every project I’ve worked on that has had issues has been because of poor communication or poor planning. Usually the two are related.

If you can’t have an open dialogue with the client, be prepared to simply be seen as a worker bee that is expected to do what you’re told. Even in this case—assuming you’re in a situation like subcontracting for another freelancer or design studio—you need to be completely comfortable that the person managing the project on your side has your back. Project scopes change all the time, but don’t let someone take advantage of your work or your time. Speak up.

Be patient, but be direct. I once made a comment that I occasionally like to have my “Steve Jobs moment” and be brutally direct when dealing with an issue. If you balance this with being the most helpful and timely person they’ve worked with, they’ll respect you for it. Trust me. It’s not about being mean, but being honest and getting to the point.

A healthy working relationship, good feedback from both sides, and fun projects will lead to your work getting consistently better, and clients will love it.

Be clear with everything and have it in writing. This sounds so simple, but it’s the single most important thing when doing business.

I hate to say that I’ve lost a friend over poor communication, but I have. Long story short, I was told, “Do whatever you think is best,” which I took to mean, “Do whatever is best.” What it really meant was, “Please read my mind and deliver everything I want, even though I’m being extremely vague.” At the end of the project, when I turned in what I thought was good based on my available resources and budget (I was taking a discount for a friend, after all), I was told that it was all wrong, that my attitude for not being more available for the project made it seem like I didn’t care, and that he wasn’t going to pay me. I responded by saying that I didn’t want him to pay me if he wasn’t happy, and that I fully accepted my half of the blame for our poor communication. His reply? Summarized, “It’s 100% your fault, you were overcharging us to begin with, and no, I won’t be paying you.” After reflecting on it, I think his partner was upset with both of us, so he wanted to shift all the blame to me rather than chalk it up as a learning experience and share the blame.

Why am I sharing this? So you don’t make the same mistakes I have.

Which leads to…


Don’t work for free.

(Seriously.)


This is the hardest piece of advice to follow for so many young freelancers. There are exceptions to every rule, and I will list some below. The bottom line is this: If you’re freelancing to earn a living and someone comes asking for free or discounted work, say no. It’s scary at first, but I promise you’ll get better at it.

A portfolio doesn’t pay rent.

Low- or no-paying jobs generally just aren’t worth it. You won’t be as invested with the project. At some point, the extra workload will become a drain both of your time and emotionally. Your client won’t see the value in what you’re providing and your influence over making the right decisions for the project will be muddied. You want them to respect you for the time you’re giving them, but also the time you’ve spent becoming one of the best in your field. Saying no in the right cases will make your life better.

But money is money, right? Why would I turn down a paycheck? You are going to succeed if you find the right fit of clients that respect you as much as you respect them. If someone doesn’t respect your time up front, it’s not going to magically get better when you’re 15 hours into a project. If you don’t have a healthy relationship with your client, you’re going to be taken advantage of, get sick of the work, and the end result is whatever you’re putting out there will suffer.

Consider all the costs. Saying you charge $30 an hour sounds awesome when you first start thinking about freelancing. After all, even many great full-time jobs start around, what, $20 an hour? Then you need to consider all the additional costs. Equipment (computers, cameras, software) is not cheap. I have well over $10,000 worth of equipment that gets used to some degree on every project.

That’s not to mention benefits, taxes (which are higher if you’re self-employed), and other costs that are a necessity. Telling a client you can’t provide a service because you can’t afford the software is not going to win you new jobs.

Tip: If appropriate, add an equipment fee into a budget or project rate. This is generally appropriate if the client wants or needs something in the project that would add a considerable expense to you — such as an underwater shot in a video. If you need to rent or acquire equipment to successfully pull off the task, that’s usually an expense the client should cover. Have a dialogue with the client to see what works best for them. Sometimes the answer is to scale back the concept.

Furthermore, the lower you start, the harder it is to raise your rates to fair market value. If you’re charging someone $30 an hour to make a website, and the relationship continues on for months, how can you ask that client to start paying you $60 an hour if you later determine that to be a fair price?

You can certainly ask for it, but they don’t need to accept it, so be prepared for that.

I’ve picked up a lot of new skills and experience over the last year, allowing me to be both more efficient and provide more to my clients. I shouldn’t be punished by working faster (if charging hourly) while providing them more for their money. Set up a schedule and give yourself an appropriate raise, just like at any other job. Announce it in advance to prepare the people paying your invoices. Be prepared to eventually become too expensive for some clients. That’s the goal, right?

But I did say there are some cases where you might work for free. Or maybe you’re not comfortable charging a fair price, or don’t have the experience or portfolio to back it up. What should you do?

Come up with your own projects. Find a friend that needs help with setting up a website, wants to be in your video, or doesn’t mind modeling for a photo shoot. We all got into this because we love it, didn’t we? Presumably, these are the things we would be doing anyway. A number of my personal projects that I put up on my website are what initially got me noticed and in the door. Now I’m building a portfolio of paid clients that is taking my work to the next level. It all comes with time.

I have about four people in this world that I will work on passion projects or for free with. If you’re one of those people, you should know who you are (I hope). These projects quite literally lead to all of my paid freelancing work in the first few months.


The fear of making the jump.

This was the hardest part. You’re never sure if it’s the right time to make the jump. There’s always fear, uncertainty, and doubt. Even successful people can still feel like frauds.

It’s always going to be easier said than done, and only you can decide if it’s right for you. It’s scary, and you’ll second guess it all the time. It never gets easier not knowing where your next paycheck is going to come from. But if you’re doing what you love, you’ll make it work. If you have talent, people will (eventually) notice.

Keep putting the hours in, keep being positive, and you’ll get there.


Why I often say no.

I generally pass on coffee meetings. Frequently, I find people that want to meet for coffee without anything specific to talk about. Maybe they want to pick my brain or we share a common interest. Maybe it’s even for business.

Every time I’ve had a meeting, or even a phone call, without a specific agenda, it’s been a waste of time. Nothing gets accomplished. When it is business, it’s usually just to kick the tires and to price shop. When I ask for an agenda or a clearly defined topic of discussion, a large portion of the time I don’t receive a reply.

I once had someone ask for a meeting without even knowing where I was located. They had no idea how much time it might take out of my day to meet with them. After they eventually agreed to a phone call, we had a five minute conversation in which they couldn’t answer most of my questions.

What was the meeting supposed to be for again?

The time investment is real, and especially as a freelancer, you have to protect your time at all costs. It’s more valuable now than you ever imagined as a full-time employee. And as an introvert by nature, when I get involved with a project, I fully commit and put all my energy into it. That can be really draining when the other person just wants to chat.

Perhaps most importantly, I want to be a doer, not a talker. When you imagine some of the great visionaries and artistic minds of the last century, you may think of Steve Jobs or Stanley Kubrick. Early in their careers before they honed their craft, what set them apart wasn’t just intelligence or vision. It was that they took their ideas and created something.


We equate great ideas to great success, but in reality it lies in the execution.

Talking about ideas makes us all excited and warm and fuzzy, but without acting on those ideas, they will never amount to more than a warm, fuzzy feeling. I would rather try and fail than only ever talk about trying.

My intent is not to offend by turning down unnecessary meetings. My intent is to focus precisely on what interests me most. My intent is to invest 100% of my energy into what is real rather than what is theoretical. I want to do something.

If you feel you need to ask someone for a meeting, maybe you need feedback or a mentor, don’t ask to “pick their brain.” It’s too vague. Show that person the value you can provide them. Show them why you’re worth knowing.

Then ask for help.


And then, there are the things they don’t tell you about freelancing.


There are a lot of things people don’t like to talk about when it comes to freelancing. One such topic is the concept of “feast or famine.” One month, you’ll have more work than you can handle, the next month, it’s gone. The good freelancers are the ones that can outlast this, they say.

People who write about freelance experiences often just cover the positives, or at best gloss over the negatives. I get to work from home. I set my own hours. That’s all great. But what about: Where’s my next paycheck going to come from? It’s something any successful freelancer will go through at least once, even if just for a couple weeks.

I did pretty much everything by the book. I worked full-time while starting my freelance career. From September 2011 through the beginning of February 2012, I was pulling some crazy hours. This happened more than once: Working at my job from 3 pm to midnight, then working on a freelance project until 6 am. I also once stayed up from the night before because I had to leave by 5 am to catch a sunrise for a shoot. I figured I’d be better on no sleep than a couple hours of sleep.

But it was worth it. I was, for the first time, getting the chance to do what I loved and starting to make a living out of it. I was happier than I had ever been. Someone finally gave me a chance. I was going to make the most of it.

I worked as hard as I could during those 5 months to get everything in order, and finally in February, I made the jump. Full-time freelance. Happiness.

Things were great. I was getting a ton of work. I had a couple ongoing relationships that meant I didn’t need to actively advertise for work, but even still I had a ton of in-bound inquiries (for a newly started freelancer without a huge network in Columbus, Ohio). I took much of what came my way for the experience and opportunity. The only thing I really avoided was low or no-pay work because, hey, I respect my time.

During this time I was getting to travel around the country, too. California, Texas, New York. Was this the perfect life or what?

I thought I could do this forever.

Then leading up to Thanksgiving that year, work slowed down. Work slowed way down. But work always slows down around the holidays and the end of the year. People are on vacation, companies are getting their budgets ready for next year, or they’re just too busy with their customers during the holidays. It happens. It happened the year before. No big deal.

I continued to follow up on leads, as well as develop my next film project. My goal was to keep working every day on something I was passionate about. Even if the money wasn’t coming in, I was getting better at writing and putting a project together.

Prior to this, some streams of my steady flow of work dried up. One company moved all their creative production to New York City. Another company re-focused their energy on taking fewer projects, while they had expanded their network the year before when they were busting at the seams—meaning they now had less work for more people. Another company just turned out to not be a good fit for the way I work, and I wasn’t able to meet their needs in the way they wanted.

But it had to get better after the new year, right? That’s what everyone told me. All signs pointed to me continuing to do the right things. And I’ve been lucky beyond words to have an extremely supportive and awesome wife who has been by my side during this entire journey.

Except by February 28th of the new year, I was still stuck. I had brought in a couple small projects since the beginning of November. The easiest way to not get new work is to not be actively producing new work. What a conundrum.

So there I was.

Do I keep running my freelance business?

Do I become another statistic?

Let me just say it: Having my own business was never my short-term ambition. I have always wanted to work for a company in some type of media or communication capacity. I want to help contribute to a team and a company that reaches a lot of people and makes a difference in their market. I want to help build campaigns, whether production or concepts. I could see myself building my own business or working as an independent director or cinematographer maybe 5 or 10 years down the line.

But this was the situation I found myself in.

I wish I had some sage advice at this point, but I’m still not sure I do. I’ve still had ups and downs even after recovering from this drought.

Telling you to “weather the storm” is awful advice because it doesn’t actually tell you anything. Yet, I don’t know that I did anything but weather the storm. I tried new methods. Contacted most of the people in my address book. Put up a Craigslist post and tried out various forms of online advertising. Offered discounts (don’t do this — it rarely works and it just devalues your time).

Sharing this story isn’t an attempt to educate you on how to avoid the feast or famine cycle. It’s inevitable. But hopefully this story lets you know you’re not alone.


Thoughts on filmmaking


I’ve realized that my passion is directing and producing video projects. While I love the technical aspects—learning how to use new equipment, and having my hands directly on how something looks or sounds—I most enjoy bringing a team of people together and working on a project. It allows me to focus on the overall vision while building a relationship with people who are extremely talented in their areas of expertise. In the end, the product is much richer and greater than the sum of its parts. Hopefully I’ll be able to continue down this path and bring even bigger projects and teams together. That’s the plan, anyway.

Bringing a team together is an exciting and challenging experience, especially in the realm no-budget filmmaking. These are people who are passionate about their craft and like your idea enough to dedicate all of their energy to it. Magic is the only way to describe it. As the director, you have to be conscious of providing your team something challenging enough that will be rewarding and valuable to them, but being mindful of the fact that they’re providing their time for little or no money.


Any person that creates something, whether a movie, a song, or an iPhone app does so because they want to connect with people. They have a talent and they want to use that talent. They want people to get something of value from what they’ve created, whether it’s a deeper meaning behind the song they’ve written that helps them get through a difficult time, or spending a few minutes of their day watching their short film and enjoying the ride.


In 2012, I made a 25-minute documentary on photography, Portrait. It was an incredible experience. I considered the option to enter it into film festivals, and I may still decide to do that, at least for ones that don’t mind if your film is already available freely online. At 25 minutes, Portrait was at an interesting crossroads. It was too long to really be considered a “short” film (though by definition, it is), and it was far too short to be a feature-length documentary. But at 25 minutes, it was exactly as long as I felt it needed to be. I felt everything in the film had its place, and I did not want to destroy that to satisfy some qualifications of a film festival that Portrait may not be accepted to screen.

It was also risky, though, to release a 25 minute film online, considering the attention deficit disorder inducing nature of the internet.

Working as a freelance videographer, you fight for videos for be shorter and shorter. When a client says a video needs to be “about 10 minutes,” you die a little inside. And it’s true, if a video is longer than a few minutes, many people won’t watch it. Others will bookmark it for later and may come back, or may not. Certainly, if it doesn’t appeal to them in the first minute or so, they won’t bother to watch the remaining 24.

But people watched and loved it. In the first week, over 30,000 people watched it. After the first month, it was just a hair under 50,000 views. Multiple people said it was the perfect length, that it let the film have room to build naturally and not be rushed. I can only recall two comments that said it was too long, and of them, they only said it could have been “about five minutes shorter.” Not twenty.

Today, I‘m able to have a better understanding of a filmmaker like Peter Jackson who dares to make most of his movies three hours long. For one, it’s incredibly hard to cut things you love, and I now appreciate that more. But two—more importantly—is that people have a longer attention span than we give them credit for. It’s just a matter of telling a story worth sharing.

All of this is to say that filmmaking is an intensely passionate and personal thing. You make a film because an idea or a subject takes hold in your mind that you can’t shake. A story you want to tell or a topic you want to explore.

This time, for me, it was looking at the creative process through the lens of photography, and how different people with different objectives approach it. Decisions I made, with respect to resources, budget, time, and scope, were ultimately personal decisions.

I put Portrait online, for free, because I wanted as many people to watch it as possible. I am happy and proud beyond words to sit here today, knowing that over 80,000 people have watched Portrait, with Michael Zhang of PetaPixel.com describing it as “…a beautifully shot documentary that may remind many of you of why you fell in love with the art in the first place.”

The alternative was to go the festival route and try to sell it. I could have made a few bucks that way, and maybe even gained more “acclaim” if it had been accepted to festivals. If it had won awards, I guess I could call it my “award-winning” documentary. But how many people would have seen it? 1,000? 5,000? Maybe. Probably not. And I’m guessing not 80,000.

I took a chance, and it was the right choice for this project. Portrait is about creation in a digital age, and what better way to share it than to embrace the internet’s ultimate equalizer: Freedom. Portrait is free to all with internet access and a web browser. It can help someone on their journey or be thought-provoking. Or they can not watch it at all.

That’s the scary part of this, particularly when you’re also trying to make a living doing what you love. Maybe one day I’ll make something that one million people watch. Or, more likely, maybe my next video will get under 100 views.

As I was approaching the end of post-production for Portrait and preparing for its release, I started focusing on what my next major project would be. I just recently finished the first draft of a script for a film. I sent the first draft to a couple friends to read, and then I started thinking: What if no one likes this idea? What if I put all this time and effort into it and it goes nowhere?


I guess that’s the nature of filmmaking. And all creative pursuits, really. To block out both rational and irrational fears. To follow your gut and know that if you push forward through the uncertainty, good things will happen.


“The blank page of any project — writing, exercising, making, learning, doing — is paralyzing. It’s the weight of great expectations and unmet aspiration. It’s the fear of finding out that you’re no good, of failing, of looking stupid. It’s laziness. It’s the specter of busyness that looms over your shoulder saying you don’t have the time and energy for this, to do it “right” — and you listen.”
Janet Choi

Writing, or more specifically starting to write, can be paralyzing. Working on a narrative feature-length script, knowing that it’s on me to come up with interesting ideas and to tell a compelling story is, at times, pretty frightening. I never have any idea if what was in my head came out on paper in the way I had hoped.

Writing is a process. Doing is the most important thing of all. Write, write, write. If it’s not good, you can delete it. But every idea is worth writing down. You never know when you’ll come back to it. I have also found that the more I write, the more ideas tend to come to me. Once I start writing, I sometimes can’t write the ideas down fast enough.

That’s the great thing about writing. It’s organic, and it can be whatever you want. Creativity is nothing more than taking your ideas and actually making something from them. Writing, photography, film… it only takes true skill and talent to become great. It takes very little skill to get started.

“The combination of clarity and freedom is what makes work a joy; one without the other is where you find frustration. When you have great freedom, but an incomplete understanding of the goal, you’re likely to invest hours of effort in a futile attempt to hit a target you can’t see.”
Brian Bailey

If I am going to be a director, I need to understand what qualities I do and do not like in a leader. I need a better understanding of how to continue to foster creativity, passion, and enjoyment towards these projects as my teams and budgets (hopefully) grow.

Be thoughtful in what you say, but don’t regret saying what needs to be said.

There’s being mean and then there’s being truthful. Some people will interpret truthiness as meanness. Generally they have a very narrow perspective. This is both true when talking about being a leader and being led. Vague instruction or direction leads to confusion, lack of inspiration, and lack of trust.

It can be scary, but do it.

This relates both to the point above and to working as a creative in general. It never really gets less scary. As you get better, the stakes just get higher. It’s not always easy to say what needs to be said, or to try a project and potentially fail, but if you’re following some combination of your brain, heart, and gut, you’ll do ok.

“The hero and the coward both feel the same thing, but the hero uses his fear, projects it onto his opponent, while the coward runs. It’s the same thing, fear, but it’s what you do with it that matters.”
Cus D’Amato

If you say what needs to be said and follow your heart, people will respect you.

People will respect you and your principles. If they don’t respect you speaking up, if they try to take advantage of you, or only care about themselves—you don’t want to work with them. Everyone is programmed to look out for themselves first, and that’s ok. But as someone trying to get their start or to build a business or an idea into reality, you can’t lose sight of that fact, either. Don’t let someone take advantage of you and convince yourself that it’s all in the name of “progress.”

As long as you are being reasonable, there are no consequences to speaking your mind.


You may find out, however, that certain people don’t want to work with you when they realize they can’t walk all over you. Be proud of that fact. If you consider losing that relationship or that work a consequence, then so be it. You shouldn’t want to work with someone that doesn’t value open communication.


Follow through with what you say.

The most frustrating part of being on a team is when someone else doesn’t follow through.

“Things will be different next time.” … “We’re working on changes and improvements.” … “You’ll get more responsibility in the next round of projects.”

If those promises don’t see the light of day after 6 months, start looking at your options, and really consider if you want to continue down this road.

These are the types of people or projects where the promise of the future is always better than the present. This is a major reason why I don’t take free or discounted work, even if it will purportedly “lead to more paid work in the future.” I also don’t ask people to work for free if they’re going to work for me. The rare exception is when there is a mutually beneficial end goal or if someone offers to volunteer their time. Ultimately, if you’re not invested, you’re going to lose interest. If you’re not taking steps towards the next progressions in your career, you’ll get burnt out.


The feeling that the floor is always about to fall out from under you… does it ever go away? I don’t think so, and it probably shouldn’t. It is what keeps you moving. If you sit and think about it too long, you’ll think you can’t handle it. If you just keep moving, everything keeps working.


Ben Affleck was a so-so actor. Some hits, some big misses. He’s an incredible director. His movies, Gone Baby Gone, The Town, and Argo have been huge successes and excellent films in the minds of critics and fans. He’s cast himself as the lead in two of his three movies. When asked why, he responded that he never knows if this might be his last chance. He’s going to cast himself because he doesn’t know if anyone else will.

I can appreciate this sentiment even more after freelancing. To sum it up with a quote from David Fincher’s The Social Network:

“Yes. Everyone at Harvard’s inventing something. Harvard undergraduates believe that inventing a job is better than finding a job. So, I’ll suggest again that the two of you come up with a new new project.”

Larry Summers, as played by Douglas Urbanski

Today, that attitude is required. The process of creating a job for oneself is critical in the creative world. No one is just going to hand you a title or money to pursue a project. You have to convince people that you and your projects are worth something. Because that is a never-ending journey, you have to pursue what matters to you, and be willing to pass on what is not. If you keep taking on the same projects, you’ll never break out into what you really want to become.

Make time for side projects. I have two websites that are for fun. If I learn and grow from the experience—even in failure—it’s been worth it. If just one person gets something out of what I produce, it’s been a success in some way.

And don’t ignore that side projects can become your main projects. I may be wrong, but I believe this is the key is happiness.

Everyone has a lot of little things that make them happy. What if you could make a living out of it? Chances are, you probably can. You just need to be willing to work, learn, fail, and grow before you can succeed. Make the small steps everyday to progress on each of those goals. Eventually one or more will be successful.

Anyone who’s transitioned from a full-time job to freelance has done this. You take small steps, small projects, and eventually you can maintain a lifestyle from your work.

The even better part is that these things can change over time. Whether small, like my preference to direct projects instead of handling the cinematography, or huge, like deciding you don’t want to do web design and working towards becoming a professional photographer.

There is no single path. There is no one right answer. The key is to keep moving forward, through the good times and the bad. Take the time to learn from your progress, but don’t dwell on mistakes for too long. The lessons you learn from those mistakes will be put to task on your next project, or the one after that.

It all comes down to getting started, and if you take those first steps, you’ve already achieved more than most.

Don’t stop there.


Make them feel something.


One of the greatest sports quotes of all time belongs to Wayne Gretzky. It actually began as a lesson imparted to him by his father.

“I skate to where the puck is going to be, not where it has been.”
Wayne Gretzky

This could describe Steve Jobs and Apple. Steve wasn’t the type of person that just showed up to the party; he saw the potential in the idea and created the bigger, better party two blocks down the street.

Yet, even his own words contradict this to some degree.

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path; and that will make all the difference.”
Steve Jobs

This is life as a creative in a nutshell. Whether an artist or filmmaker or entrepreneur, every day is a contradiction.

I highly doubt Mark Zuckerberg’s original vision for Facebook was to get everyone in the world online. He just created a platform that allowed friends to connect. Eventually, he connected enough of the dots to realize the true potential of the website he started from his dorm room. From there, his story became more clear.

You can often feel like you don’t have a voice unless you have something brilliant to say. Sometimes, the stories that connect the dots are just that — stories. Sometimes, even co-founders can’t agree on the origin story of their product.

If you are compelled to create, then create. It’s ok if you don’t know what your end goal is from the outset. Maybe you don’t even know what a puck looks like, much less where it’s going to be. If you have something to say, your voice will develop. You will be able to connect to dots, eventually.

The important thing is that when you have a burning desire inside to create, others can feel it, too.

Creating is as complex as life itself. Take your ability to create, and say something you care about. That should be what fuels you, and is what will allow you to look back and see the big picture, the logic behind your choices. It doesn’t have to make sense at the time. Andrew O’Hagan put it best, “Responsible behavior in an artist is like modesty in a stripper: unbecoming, dispiriting and not at all what you signed up for.”

Don’t worry about your narrative, your brilliant story that will be a book, and later made into a movie.

Create. Make people feel something. You can connect the dots later.

“I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.”
Maya Angelou

Finally—the secret to freelancing.


There isn’t one.

The first thing a new freelancer needs to realize is that nothing is one-size fits all. Some projects (or budgets) won’t fit you and what you’re trying to do with your career. Maybe they’re above your head, or a step backwards. That’s ok. Likewise, not all advice will fit you.

This is the best advice I can give to a fellow freelancer:

That’s all. It’s up to you to figure out what specifics fit you best. Whether you like charging hourly or per project, and what rates you charge. What services you want to offer and what type of projects are best suited for you. Whether you prefer to meet in person or collaborate in other ways.

There’s a lot of information out there about what works and what doesn’t work. Some of it is true. But it really is up to you on how to approach things. I can tell you how I do things, but that doesn’t mean it will work for you.

So take it all in, digest the information, and figure out your own plan.

The important thing is this: Don’t waste time making mistakes other people have already made. That’s where the advice comes in handy. My goal has always been to share as much information as I can with anyone who wants it. But just remember, only you can decide what works best for you.


What now?

Because I wrote all of this throughout different stages of being a freelancer, it only feels appropriate to update you with where I am now. Today, I work full-time with the amazing people at Big Cartel and couldn’t be happier. I’ve been able to use my skills to contribute to a team that’s doing fun, cool things and supporting artists just like me. Through Big Cartel, I can reach far more people and have a far bigger impact on other creatives’ lives. It’s what I’ve always wanted to do.

That’s not to say my time as a freelancer was a failure. Anything but. I grew, I learned, I struggled, and I came out the other end better for it. I wouldn’t be at Big Cartel right now if I hadn’t taken risks and put myself out there. We first connected when they shared a project I made. Something I made for fun. In my spare time.


You can never be prepared for where freelancing can (and will) take you. You’ll have higher highs and lower lows than anything else you’ve ever done. Your work is you.

Just keep building, keep creating, keep working. Great things can (and will) follow. You never know when, you never know where, but if your heart is in it, someone will notice.



Thanks.

If you made it this far, I owe you.

Feel free to send me a tweet or an email — let you know what you thought, or what you’d like me to write about next.