There are two words that can make any freelancers’ heart skip a beat:

Guaranteed. Income.

(Did you feel that little flutter? Me too.)

However, for many freelancers, there are only two reliable ways to make those sweet words a working reality: by signing clients for long-term projects, or retainer contracts.

While it sounds easy enough, projects like those can be hard to come by. Most clientele outside of agencies just don’t have the cash flow, or enough necessary work for consistent 4- or 5-figure contracts.

That’s why, when a hard-working freelancer is given the opportunity to go long-term, most of us jump at the chance.

There’s just one problem:

“Massive projects come with challenges equal in size.”

One of my favorite quotes from ‘product guy’ Justin Jackson is about the hardest parts of a project being the first and last 10%. But there’s a whole lotta work between those two points.

What about when you hit 70% and all you want to do is stick a fork in it and call it done? How do you keep up your momentum for a project after 3 months? Or 6? Or a year? How do you keep coming up with fresh ideas when you’ve been immersed in the same brand day in, day out?

In the last year, I’ve set up my business to work almost exclusively with clients over long-term contracts.

It’s an adventure I don’t regret embarking on, but it’s also opened my eyes to the ways those sweet, sweet guaranteed income projects can turn real sour, real quick.

Taking on a long-term client is like entering a long-term relationship. The secret to success comes down to choosing carefully, communicating well, keeping things spicy, and refreshing your dedication when you need to.

However you begin, begin with caution

Veteran creatives will tell you over and over: “Don’t chase the money”.

It’s solid advice. Until a client is offering you $5k/month to join their team. Sure, they’re not your favorite, but when you see that dollar figure, you wonder: How can I say no?

The short answer? Of course you can say no.

But the long answer starts with an important reminder: If you’re going to do this, you need to decide how much your sanity is really worth to you.

For example, the first retainer contract I ever signed was an absolute nightmare. While this particular client was genuinely lovely and wanted to help people, they also had no idea what they were doing.

They showed up to our first meeting — at a very nice restaurant — wearing basically pyjamas. They were clearly unfamiliar with basic content strategy, and were extremely young in a field that required significantly more life experience than they had. I also sensed the work would bore me to tears.

But when I found out how much she was willing to pay me I said “Yes” without hesitation. I really, really needed the money.

As you might expect, for 3 months of my life chaos reigned. I struggled through drafts and calls and every other step along the way. But while I stuck it out till the end of the contract term, I never took another project from them after that.

Nowadays, I’ve created very specific criteria for long-term clientele:

They absolutely must be established in their fields and we must complete one short-term project before committing

They must have a trained team and project manager behind them

They must have concepts, projects, and messages that really mean something to me

I also make it a point to align myself with clients who put me to work doing what I want to do. Pinpointing the projects you’re passionate about is a huge part of developing your niche.

Ultimately, procrastination and motivation come down to our connection to the work and the value we get out of it (beyond the money!). So developing a niche that you enjoy working on can help ensure that you don’t end up in those slumps in the first place.

While this list of ‘must have’ criteria may look different for you, I highly encourage you to outline one, and stick to it. No matter how much cash is on the table, there is nothing more precious than your psychological health and happiness.

(Of course, you can test that theory. But I can almost guarantee you’ll come to the same conclusion).

When you’re in the throes of long-term work, communication is key

In order for this long-term project to stay a positive, mutually beneficial experience, you have to be clear about how you’re going to make things happen from day 1.

This includes setting boundaries, outlining typical project timelines, and making sure your clients are crystal clear about your overall processes.

Just like the beginning of a romantic relationship, you and your client will need to learn to ‘speak each other’s language’, and uncover your preferred ways to communicate.

Train them on the processes that work for you, such as the best ways to give you ideas, offer feedback, etc …

For example, do you prefer to get an outline of a project at the beginning of the week, and then hand in your work the following Friday? How quickly will you need your questions answered? Are critiques coming in fast enough for you to hit your deadline?

For me, the best way to avoid total communication breakdown is to get on the phone with the client as often as I can — which may be every week, or every two weeks, depending. That’s because the longer I go without speaking to a live human, the more removed I feel from the project.

Test the waters and find out what works for you.

Project routine getting too… routine? Be prepared to spice things up.

Finding the right client and the right flow is one thing, but once you’re elbow deep in a project, what processes will help you inject inspiration back into it?

“When you feel the motivation slipping, you need to get that initial streak of enthusiasm back, and fast.”

To do this, I recommend a twofold approach:

Cultivate your interpersonal relationship with your client, so you can call on them just to chat about the project in an unstructured fashion when you need to (this will help you refresh your ideas and angles)

Use some of your favorite tools at your disposal so your clients can keep feeding you fresh, candid information

If a draft has me nodding off at my desk, that means there’s a gap somewhere. I find the best way to wake up is to get some new questions about the project answers.

In my case, that means sending a quarterly survey with questions about where they are in their business, how they’re doing with the project, what they want to see change for themselves and their audience in the future, how they feel about the solution they offer, and what’s about to happen next for them.

But there are no limits to this approach or ways you can use it! If you’re a designer, you might invite your clients to create a quarterly ‘inspo board’, or send you a playlist of their favorite current tracks so you can get more of a feel for their current vibe.

In general, I invite my long-termers to send me any additional stuff they like: images that inspire them, stream of consciousness emails (in accordance with a specific timeline so you’re not overloaded with these), etc… at will.

It helps me stay engaged, interested, and asking the right questions.

But wait: when you hit that last 10%, how do you stay dedicated to the final push across the finish line?

Great creative work shares a common element: devotion.

Devotion to the deadline, devotion to the idea, and devotion to the project you’re in charge of helping shape.

“Always remember: Sanity first. Work second. Money, last.”

But devotion takes hard work and a ton of energy to sustain, and is incredibly hard to ‘play catchup’ on. So in order to keep your focus fresh, and make that final sprint, prepare yourself ahead of time with everything you need to look back, get new ideas, and stay motivated (a.k.a. have the strategies we just discussed in place!)

Choose your clients carefully, so you know you’ll be able to make it through even the most challenging moments

Be honest about what you enjoy, so you don’t want to poke your own eyes out when crunch time is in full force

Have clear systems for client expectations, feedback, and finalization ready to go

Have a solid rapport, and tools in place so you can keep the extra ‘push’ inspiration coming in when you need it

And lastly, never forget: your talent is a precious commodity. Act accordingly.

While it may seem appealing to seek out long-term clients ASAP, this is not a process that should be rushed — for your sake, and your clients’.

Instead, take it one step at a time.

Find ideal clients by playing close attention to the people who you do short term projects for. Who might need you long term in a year? Who’s already in need of a bigger team, and your expertise? Who really believes in you and the investment they make in you?

Then, when you’re ready, approach them with a long-term proposition.

Give your instincts credit. If you lock in, you’re contractually it for the long haul. So if you’ve got a good feeling, Gear it out. Seeing red flags? Trust yourself.

Never chase the money for the sake of it. Even if you get an offer — if it’s not a fit yet, wait it out. You can slowly build your retainer list while still taking on short-term projects and ease into the retainer-only system when you’re ready (if that’s what you’re going for).

And always remember: Sanity first. Work second. Money, last.

Image credit: Eric Huang