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10 Mistakes I Made While Freelancing

I screwed up. Big time.

About five years ago, I took on my first freelance client as a sophomore design student at Drexel University in Philly. I made so many mistakes. Lets face it. I had no idea what I was doing.

What happened since?

I continued freelancing through school to gain more experience and when I graduated in 2012, I moved to New York to find better opportunities and keep freelancing at Scratch where I had done an internship. I enjoyed making my own schedule and I couldn't find a salaried design job anyway, so I just kept freelancing and learning as I went. 

These few years were incredibly formative for me and I wouldn’t trade it for the world. But to be honest, I made a lot of rookie mistakes with my clients along the way, and had to learn from them the hard way.

After the apartment fire (one year ago), I needed some stability in my life. I took a full time position at MKG, one of the agencies where I had been contracting. For the last year, I've been working there to save money, get more experience on big budget projects and make more connections. My current goal is to break back out on my own as a freelance lettering artist.

This weekend I am starting fresh in a new apartment and home studio in Brooklyn. This is a big leap forward, since I have not had a dedicated workspace ever since I lost my old apartment. I figured it was a good time to take inventory of what I've learned over the years. I originally wrote this more as a letter to myself, but I hope you will get something out of it too.

Here’s a list of 10 biggest mistakes I made while freelancing. I hope they are helpful to you if you do freelance work or want to make the jump.

1. Working for free

After graduating college, I was eager to get my work out there and build my portfolio. A good friend started a new company with a great mission, and he needed some basic branding. As a friend, I was happy to help him out. Nothing wrong with that, right?

The key mistake was that I didn't communicate the value of my work.

He had no concept of what my design (or my time) was worth, so he kept asking for more and more as if it was just a fun hobby of mine. In the end I felt taken advantage of.

Looking back, I realize it was all my fault. I should have communicated to him that each piece of the project was worth $XXXX and that he was going to get them for free. I've done this on more recent pro bono projects and it led to mutual respect and much more appreciation for the work.

There's nothing wrong with doing little favors for people (especially if it's for your mom). But after a certain point it becomes a real project. If you want to do it for free, make sure they know how much value they are getting.

2. Not using a contract

I also I didn't use any kind of written freelance agreement for that project, or any other ones that entire year.

"But the project was pro-bono. Why would you need a contract?"

Contracts are not just about getting paid. They also cover the project scope, ownership of the finished work and many other important things.

Use a contract for every project. 

Actual clients expect a level of professionalism, otherwise they won't take you seriously. I'll get more into the specifics later.

3. Not getting paid up front

One of first paid projects was creating type-based environmental graphics for an exhibit at my college. When the brief came in, I was so excited about the project that I started working on it the very same night. I hadn't discussed the specifics of the payment structure, and it took over 90 days (90 DAYS!?!) from the completion of the project for me to get paid anything.

At least I got paid, right? Well, I've learned since then that it's an industry standard to get paid half up front.

Don't be afraid to ask for a 50% deposit before doing any design work.

Recently I've taken it a step further by presenting low res images of the finished work at the end, and sending the final files after I receive the last payment.

4. Chasing clients instead of attracting them

When I didn't have work coming in, I would go on Craigslist and search for gigs in the Art/Media/Design section. I'm not embarassed.

Here's the thing: I was desperate. I was looking for the work – whatever I could get, really. The problem with this is that when people agreed to work with me, it was like they were doing me a favor, so they were in control of the situation. Ideally you want to be approached by the client. This way, you are in the position to walk away at any time. It's much harder to say no if you are the one who reached out in the first place.

What if no one is reaching out to me for projects?  

Here's a way of thinking about it that I wish I knew when I was starting: Think about what kinds of clients you want to work for. Learn their language, make good work that will attract them, and put them where they will see them. Be patient. People will hire you.

4. Working with anyone and everyone

Most people out there want everything to be good, cheap and fast and they don't care about what goes into it. They don't see design as an investment in their brand, but just another expense they want to keep down.

I've worked with too many of these people before, and they will try and take advantage every time. You can get by and make a living without being selective, and it seems like that's the only option when you don't have a lot of demand (Spoiler alert: it's not the only option). I realized later on that it's just not a sustainable way to run a design business.

Unprofessional work leads to more unprofessional work.

You have to be selective. Look out for red flags in each prospective client. If an alarm goes off, don't ignore it. Take a gut check and evaluate if this might be more of a headache than it's really worth. Some people are just not worth your time.

5. Not clearly explaining my process, or the terms in my contract

Once I finally started using contracts, I took the lazy route and just downloaded a template and filled in my information. I didn't really understand what it said. This left my clients (and myself) quite confused. It's probably the dumbest mistake I made.

No one understands your process like you do. If you don't have it written down anywhere, I would highly recommend doing that and sharing it on your site.

Once I started guiding my clients through how I work, and why I work that way, (like magic) they started to trust me more. They knew what was coming with each step of the project, and they felt better about working with me. I have case studies on my site that go through my process and how I arrived at the solution. 

Not everyone needs to learn every detail of how you work, but setting a few expectations goes a long way.

Now I use a service called Shake to generate and customize my contracts. Most of my clauses are in plain english. I briefly explain each section with the client over a call so we are on the same page. This has helped garner trust and lead to more successful working relationships.

6. Being a Jack of All Trades

I think it's safe to say that we all enjoy a bit of variety in our work. There is not one specific function that we can do for the rest of our lives. So why should we specialize?

I used to do all sorts of creative work for my clients – branding, web design, photography, retouching, even video. I wasn't gaining much traction because I wasn't known for anything.

For a little over 2 years now, I've only been sharing lettering work and the change has been incredible. It's not that I don't ever do other types of work. I just only share the lettering stuff, because that's what I want to be known for in this season of my career.

It's not easy to choose a direction when you have multiple passions, but the best thing you can do is to just pick one and move forward. You can always decide to change it.

7. Not updating my website

In this day and age, having a website is so necessary. There are so many great platforms you can make a website on. But once you have a site, the work isn't over.

I left my site up with a bunch of student work on it for way too long. It just looked unprofessional and it was giving the wrong impression.

Your website should be a living, breathing organism.

Even when you have a steady flow of work, it's important to keep putting up new content every month or two. It should never look stale.

If you don't have a website and don't know where to turn, I would recommend Squarespace for their ease of use, and Wordpress if you want more control.

8.  Waiting for the unicorn

What if I don't have any cool projects coming in? 

Go make some damn work that you're proud of! You don't need a dream brief to make something good. You can choose to make your best work, if you put in the time.

Stop wasting time on the BS, and make more personal projects that you enjoy. Putting those out there will attract more of that kind of work. Everyone wins.

9. People Pleasing

The client is always right, right? I disagree. We can't the make client happy in every situation.

Have some damn integrity.

Clients hire professionals to help them solve a problem. Sometimes it requires saying "No" to one of their requests. If the goals are clearly outlined up front like they should be, there should to be a reason why you chose that color.

I'm not saying you should always ignore what the client has to say, but if they are shooting them self in the foot, it's our job to let them know. 

10. My biggest mistake: Not covering the bills

This the biggest mistake I made, and it led to many of the other mistakes above.

I was living paycheck to paycheck.

I was in a mindset of scarcity, which resulted in stress, wasted time/energy and poor decisions. I was trying to start a freelance career (in New York City, of all places) and I didn’t set aside money for my bills! I had a little money in the bank just in case, but it was more of an emergency/savings fund than a real foundation.

Each month, I would hope to get enough freelance work to pay my rent without dipping into my emergency funds. I scraped by, but it was definitely tough.

I acknowledge that for some, not having money can be a great motivator to get to work. But it made me feel uneasy and it caused me to make poor decisions that were a serious detriment to my long term success.

You don’t have to go full time freelance right away. It's a lot of pressure. You can get a day job, (or a part-time job) and freelance on the off hours to see how you like it. It's certainly not an easy route and not everyone is cut out for it, but its infinitely more rewarding to be running your own show and be selective.

How much do I need to save up before I can make the jump to full time freelance?

I've talked with many other freelancers about this and unfortunately there isn't one clear answer. 

Everyone has a different capacity for risk.

For me, I need to have 6 months of bills saved up (on top of my emergency fund) and a steady stream of good projects coming in. 

Some like to save up a whole year worth of bills before they go rogue, just in case no one comes knocking at their door. And some people just go for it and hope for the best. I fall somewhere in the middle of this. I am confident that I can attract good, paying clients, but I also don’t want to fall back into that scarcity mode.

The good news is: with enough patience and persistence, you can pretty much do whatever you set your mind to.

If you are seriously thinking about going freelance and you are willing to put in the time, you have a better chance than most. Thinking about the long term goals has helped me realize and move past all of these mistakes.

Lastly I need to give a shoutout to the seanwes podcast. When I started listening in 2013, I began to realize all of these mistakes and take my business more seriously.

If you have any feedback on this article or questions about freelancing, I'd love to hear from you. Please don't hesitate to reach out.

Eric Friedensohn