Top 12 Mistakes I’ve Made in My Career

Being a freelance writer is a tough gig. Not because of the writing, though that has its own difficulties, but because of the business side of things. Through the many years I’ve been doing this, I have learned some tough lessons. Here are my top 12:

Listening to a Client About Not Needing a Contract
Sounds crazy, right? Of course you need a contract. But what happens when a good friend introduces you to someone who needs a writer and it’s an intriguing project you want to do? Well, in my case, I listened to my friend who said the client didn’t do contracts. I worked my tail off. Now cut to me several months later sending invoice after invoice into the ether. The director/client had disappeared and I was left not only without a paycheck but holding receipts for expenses he had not reimbursed. Lesson learned. I was out several thousands of dollars and a boatload of time. I insist on contracts every time and have had cause to enforce them in similar situations. Always get a contract. If a client balks, walk away. That is a huge red flag and one you should never ignore.

Not Asking for Enough Pay
When I started, I wanted the work. I let clients lowball me. Heck, I undervalued my own skills. I did some investigating and found the market range for rates in my area. Since I had come from a corporate background and then been a Director of Communications for a national association, I had more than enough skills to command a higher market rate. I changed my rates and not only did I earn more per hour, but I got better clients. Do your research. Find out what people with your level of skills (be honest—don’t demand high rates if you are just starting out) are making and charge a similar rate. This will depend on your location, of course. Metropolitan areas are typically higher than more rural ones.

Not Calling the Attorney Soon Enough
Every business needs legal help and not only when times get rough. It helps to ask an attorney how to set up a legal business and get your paperwork in order. I thought I could do it on my own and save some money. I read books and asked consultants (the free ones at the Small Business Development Center, which was one of the best things I did), but an attorney would have refined my contracts and terms. It doesn’t cost that much to do a consultation. You don’t need a ton of time, just guidance and paperwork review. Trust me, it will help when you have a client go into bankruptcy like I did. Or when signing a contract with a publisher or magazine or major corporate client. It never hurts to have someone looking out for your interests.

Staying with a Bad Client
It’s easy to say bye to bad clients with bad work or clients who don’t need your services too often. My mistake was sticking with a terrible client (I’m talking awful here) because I liked the other people I worked with on the projects and the work itself. It was interesting and fun. But after dealing with the chauvinistic, rude and unhygienic environment (trust me, you don’t want to know), I called it quits. It made a huge dent in my billable hours and cash flow, but I no longer felt dirty or abused. I stayed too long and put up with too much. These days, I don’t put up with bad clients. For more details on this topic, read How to Fire a Client with tips for identifying bad clients and how to get rid of them professionally.

Not Limiting Edits
My first freelance contract didn’t specify how many rounds of edits I would do for the specified rate. Since most of my work is large-scale, I typically offer flat-rate contacts. It is absolutely essential you specify how many rounds of edits you will do in that flat rate. After a shocking 21 rounds for one project (that ultimately reverted to my first draft!), I added in a three round limit. Anything above that requires additional fees paid per hour. I won’t work without this in place these days. Three rounds allows you to fix any issues with the approach and concept (though these are typically handled in the treatment phase), adjust any miscommunication or misunderstandings, and fine tune the copy. Anything more is usually a sign the client doesn’t know what he wants. It is rare for me to do more than three rounds these days.

Not Hiring an Accountant Soon Enough
I hate doing taxes and books. I did not go into writing because I loved numbers. But when I first started (and for many years afterward), I did my own finances. When I did hire someone, I realized I had been missing out on deductions I could have taken. A good accountant is invaluable. Plus it means I don’t have to do it, which is a win for me.

Not Networking Effectively
I’m an introvert and do not enjoy networking. Oh, I joined groups and even volunteered for positions on the boards, but I didn’t take advantage of the networking opportunities. I showed up and thought that was enough. I did the work, because that was easy. I knew how to work. Schmoozing is another matter. I’m still not good at it, but I have gotten better. It’s still a weakness I need to overcome.

Not Recognizing My Weaknesses and Not Getting Help
In the past, I tried to do everything myself, even those things I am not particular good at, like finances or technology. I muddled through. But if I had admitted my weaknesses earlier I could have gotten help. I’d have learned computer tricks and time-saving techniques. I’d have saved money on taxes. I’d have built a better network. Just because you are an independent writer does not mean you need to do it all alone. Take a hard look at your weaknesses and find ways to strengthen those areas, whether by hiring someone to help you or by taking classes to boost your skills.

Not Backing Up
Okay, this one was a painful lesson and one I am still feeling. As I mentioned above, I am not the most technical person. I’m good at certain things (like running programs) and rubbish at others (like anything related to how a computer runs). One of my big weaknesses is not backing up. I realized this was an issue and decided a few years back to get better at it. I plugged in a hard drive and copied my files. Then I bought a new computer and set up my new files and backed them up, or thought I did. This is when disaster struck. My old computer, which was acting as an archive, died. All the files were gone. No problem, I pulled out the external hard drive I’d back up to and it was empty. Apparently, I had done something wrong. I lost ten years of work in one day. No samples. No archive. Nothing. I am still mourning that loss. I can’t say this enough: Learn how to back up and do it properly. Then store those files in a way they cannot be deleted. Trust me. It’s not hard to lose files these days with the cloud, but I am now paranoid about missing files. Get a system and be consistent.

Not Protecting My Samples
This is a similar issue. My storage room is in the basement beneath a bathroom. Do I need to say anymore? All of my hard copies were ruined too. Well, almost all of my hard files. Not every single one was lost, but way too many were. Waterproof containers. That’s all I have to say about that lesson. Waterproof containers. Firesafe wouldn’t be a bad idea either.

Not Pursuing Opportunities
There are a lot of writing opportunities out there in the world. But I find the biggest obstacle to getting those jobs is me. I hold myself back, thinking I don’t have the right background or the right samples (which given the stories above, is sometimes true) or that I am not the right fit. The biggest mistake I’ve made is not going for it. Not trying for jobs because I rule myself out before I try. Now I do. I throw caution to the wind and try. The worst thing that can happen is that I get rejected. So what? That’s going to happen anyway. This business is all about rejection. Might as well try. All you need is one person to say yes. The funny thing is that I feel like I was more aggressive about opportunities before I had my business. Once I started working for myself, I got more timid. It took awhile to adjust. Now I embrace my old attitude and go for it.

Wanting It to Be Perfect
The last mistake for this blog is not sending things out until they are perfect. The problem with this is that perfect doesn’t exist. If I’m waiting on perfect, I am going to be waiting a long time. These days, I do my best and get my work to a place I can accept and then send it out. If no one picks it up and I need to reassess, that’s fine, but at least I am trying. This is true for pitches, queries, manuscripts, and client presentations, whatever.

What lessons have you learned?