Hold ’em or Fold ’em

It matters not how strait the gate,
How charged with punishments the scroll.
I am the master of my fate:
I am the captain of my soul.

~ William Ernest Henley

The final four lines from W.E. Henley’s poem, “Invictus,” will ring true for most freelancers.

We choose this career path because we feel a need to be the captain of our own ship. And even though we work for our clients, we still maintain ultimate control over who we choose to work with.

Part of what makes being a freelancer so much fun is that we have an opportunity to work with a wide variety of great clients. As much as it’s nice to think we’re the ones helping our clients, I am the first to admit that I learn something new from each entrepreneur I work with. It can be a mutually beneficial relationship if you keep an open mind.

Growing your business involves learning which clients you should be working with and which ones you might consider steering clear of. When we first start our business, we have no filter. Anybody who comes along looking for help with a few bucks in their pocket meets our criteria for a good client.

But that wears off pretty quickly. We learn that in order to grow, we’ll have to stop doing discounted work for relatives and people whose conversations begin with “can you give me a good deal?”

When To Hold ‘Em

We’re here to serve our clients. As a freelancer, whether you’re a writer, developer, photographer or translator you attract new clients and retain existing ones by doing the following:

  • Providing value
  • Building a relationship
  • Working hard
  • Going the extra mile

None of these things are difficult and there is no excuse to overlook any of them. If you’re landing some work and struggling to grow your business, other than improving your exposure, those are the first four things I would take a closer look at.

I wrote a whole post on this over at Horkey HandBook and as much as “Customer Service” seems to be a simple topic, it’s often overlooked.

Assuming you’re living up to your end of the bargain and doing a great job, there will likely come a time when you question the value of continuing to work for a particular client. It can happen for a variety of reasons and you’ll be in a position of having to decide: hold ’em or fold ’em.

We can’t just work for money–there has to be a greater purpose which you’ll need to discover on your own. For me, it’s helping other people be successful. As silly as it sounds, I get excited when I help a client with their digital marketing and see it translate into actual results. Knowing that I can play a role (even a small one) in helping someone else grow their business is a pretty cool concept.

A Great Connection

There are lots of reasons that make it worth maintaining a client relationship despite the occasional bumps that occur along the way.  Sometimes it’s as simple as connecting really well on a personal level. I’ve had many interesting conversations with clients that have absolutely nothing to do with business. We end up talking about kids, families, CrossFit, whatever comes up. These conversations don’t happen with everyone so when they do, take note.

Some clients are just enjoyable to work with and that alone can make them worth their weight in gold. As freelancers, we spend a lot of time working alone and having a relationship with a client that flows makes work more fun.

Future Potential

Maybe you see potential in a client who has a new business. If you’re willing to work with a start-up, it can provide an opportunity to grow together. Just make sure you establish some guidelines. Outline a start-up rate with the understanding that as they get busier and give you more work, you rates will slowly increase. These scenarios can provide a win-win opportunity.

They Pay You Well

Of course, I would be remiss if I didn’t discuss income. Even if we love the work we do, there are bills to be paid. When I first started, like many freelancers, I worked for very little–sometimes even free. I did this to build a portfolio and get some experience under my belt. At some point, you need to stop the free work and start making a living. I worked for free for way too long and I’m still paying the consequences.

If you’re still in the position of working at a discount or worse yet for free, STOP! No, seriously, stop reading this and grab a piece of paper and a pen.

You’re back? Excellent. Now write on that piece of paper a firm date, sometime in the next 30 days, that you will cease doing free or discounted work. Here’s why:

Good clients, even the ones who are friends will pay you what you’re worth. As long as you are providing them with value, you deserve to be paid.

They’re a Good Client

In my experience, the vast majority of clients are awesome. It comes down to finding a balance between your needs and theirs.  If your gut feeling about a client is positive and they are happy with the work you are doing, then things are good. A lot can be said about loyalty–both providing and receiving. A few of the clients I work with have never seen an increase in their rates because that’s what I promised them. They don’t pay enough for the value they receive, but I’m ok with that because they stood by me when I was getting started. Their loyalty carries a high value.

On the other hand, not every client (or freelancer for that matter) is a winner. If you start feeling like the imbalance between the value provided and value received is too great, it might be time to move on.

When To Fold ‘Em

Being a Freelancer can be a little like working in a rose garden. It’s a beautiful thing but every once in a while we end up with a thorn in our side.

Not all client relationships are a match made in heaven and there can come a time when we need to cut ties. I always advocate for the idea that if we need to end a relationship with a client, it should be done with honesty and on a positive note.

Cutting a client loose is always a decision that I find to be a little more cut and dry. You’ll know when the time is right–it’s like drawing a line in the sand that you just won’t let people cross.

Spotting red flags early on becomes easier with experience. But sometimes we miss the warning signs or a situation changes mid-project. If you’re currently working with a client and things are not going smoothly, there are a few reasons to consider moving on:


This one is pretty straight forward. Nothing stings more that working hard to deliver the value you promised and then not getting paid for it. It’s just as bad when you have to fight for your money. I have more patience for people who chronically pay late than those who don’t pay at all but that can become a problem too. There are lots of creative ways to collect your outstanding bill but once that’s taken care of, it’s time to move on.

All Take, No Give

Nobody likes a one-sided relationship and that goes for the business world as well. There are many different facets to a healthy business relationship and what works for you might not work for the next person.

The longer you work with a client where things are out of balance, the more you will begin to resent the whole situation. But how do you know whether a problem might exist? It’s easier than you might think: Just pay attention to how you feel when your client sends you an email or calls. If you find yourself dreading the interaction, you’ve got a problem.

Black Holes

Google defines a black hole as “a mathematically defined region of spacetime exhibiting such a strong gravitational pull that no particle or electromagnetic radiation can escape from it.” Some clients are like that too. They suck massive amounts of your time and energy into a dark void. Never to be recovered or compensated for.

It’s not always intentional. I once had a client who was so long-winded in his emails that I dreaded every interaction. Ironically, he was a writer, and a good one at that–an extremely nice person. But the moment I received an email from him, I broke into a cold sweat. The though of having to read 1000 eloquently composed words to discover a single important point became a long term problem that I could no longer deal with.

If a client takes up so much time (and I’m referring to unpaid time here), that it begins to have a negative effect on your other work, move on, if the problem can’t be resolved. Respect your time and respect your clients time.

Some Final Thoughts

Managing client relationships can be a challenge sometimes. Truthfully, real problems are few and far between and as freelancers we need to roll with the punches. Every good relationship has its ups and downs. It’s important to look at clients both individually and as a portfolio. Work hard to keep them happy and if a bad one comes along every now and then, be quick to pull the plug.

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