What I’ve Learned From 40 Years of Freelancing

Stephen Kennedy creates photography that can’t be ignored. His portfolio includes clients like Wells Fargo, Ford, and Johnson & Johnson. His career is founded on four defining principles: simplicity, commitment, experience, and trust.

In August I’ll start my 40th year as a freelancer. If you’re wondering what has changed since 1980, the answer is almost nothing. In a business based on relationships and demonstrable skills, it’s the same as it ever was.

Even after all these years, it’s not any easier or harder. I don’t have to hustle any less. Luckily, there are far more ups than downs. From the very first day until now, I continue the ongoing labor of love: get work, and strive to stay relevant.

Like a lot of creatives for hire, I thought getting work and getting noticed would get easier as time passed. As with my childhood dreams of flying cars, robot butlers and teleportation, most of what I had hoped for was a fantasy.

There’s a natural progression for most freelancers that goes like this: pitch yourself, get considered, get the gig, do the gig, deliver the work, and wait for the process to start again.

Early on, I was under the impression that mere excellence alone would mean that the phone would ring every day. What I didn’t understand was that I existed on a spectrum of problem solvers and that every problem didn’t need me as the solution. Part of this has to do with being a specialist in my field. That reduced an already small marketplace for my work but it also allowed me to charge more for my expertise.

The other part of it has to do with the human nature of people who hire freelancers. Nobody wants the same thing every time. Variety is the spice of life. Just like you don’t eat at the same restaurant every time you dine out, you’re not going to get hired for every assignment.

The logical way around this is to simply find more people who are willing to pay for what you do. This will require a substantial effort at networking. It will also require marketing and promoting yourself for as long as you want to keep working. This is daunting to even the most experienced freelancers but it really works.

The good news is that much of the heavy lifting can be systemized, though you’ll always need to keep your hand on the wheel. My business is sustained by a small group of people who have very specific needs that I’ve proven capable to fulfill. The members of this list hear from me every five weeks in the form of a mailed letter, phone call, or face to face meetings. The letters I mail are hand signed and contain a signed artist’s proof that I printed myself. I make sure that meetings and phone calls are brief and efficient.

This is exactly how I have always promoted myself. Certainly, it’s easier now then it was when I first started. Much of the ease has to do with improved office technology. Things like my dual tray laser printer, digital contact data, word processor templates, and the ability to make fine art prints for less than the cost of an espresso.

I know a lot of freelancers that think mass email blasts and social media posts negate the need for my traditional marketing strategy. I believe that’s simply not true. As long as people still open postal mail, still allow me to meet with them, and still like personalized communications, I’ll keep it up.

There are many paths to the same creative destination of making a living as a freelancer. Here are a few things that have worked for me and for my most successful friends and industry peers.

Conduct yourself in a way that makes it easy for someone to send the next project your way. Remember the first time you used Netflix and realized that you’d never ever have to pay another Blockbuster late fee? That’s what I’m talking about.

A little discipline goes a long way. This applies to both art and craft. Freelancers can’t wait around for inspiration to strike. That’s why it’s so important to work on systemizing your creativity. This means doing something pertaining to your career every day.

Be yourself. This might be the hardest thing to embrace. Once you’re over the hump with this one, your life will get a lot easier.  

Standardize your creative output. People who hire you based on your portfolio or previous projects don’t want something different, let alone a surprise from left field. The exception to this is delivering exactly was expected and also including a little something extra that might be just the thing that the client never knew she needed.  

Use the belt and suspenders method. An experienced freelancer will always have a backup of every mission-critical tool or process needed to deliver an assignment.

People that hire you are not like you. They are employees and you are a hired gun. They aren’t spending their own money. They measure success using different metrics. Don’t forget that all of your clients secretly want to be you!

No news is good news. If you’re waiting for adulation for what you just delivered, you’re doing it wrong. Assume that your delivered work is just fine unless specifically told otherwise. I promise you that if the work didn’t measure up, you’ll hear about it right away.

There are many ways to prosper as a freelancer and these suggestions are intended to make it just a little easier. Of course, things are constantly changing. For me as a photographer, there was a profound change in the early 2000s with the shift to digital. But that’s simply an improvement in the craft and efficiency of delivery. The same goes for cloud services, Photoshop, email, and mobile phones. They’re not entirely new things, just updated versions of file cabinets, airbrushing, postal mail, and two-way radios.

A photographer like me still has to “be there” to create or capture. That’ll always be the case regardless of technology.

Real change is rare. I still go to my assignments in a car. My main tool is still a camera with interchangeable lenses. I still use a reporter’s notebook to store my notes and I still use a golf pencil to write because even today pens can leak in pockets.

Sticking with what works when your reputation is on the line is never a bad idea. It’s also worth noting that your client’s reputation is on the line every time you get the gig.

Focusing on relationships and having a business model that mimics The Golden Rule will take you almost anywhere you want to go in the freelance world.

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