7 Freelance Productivity Lessons from an Incurable Slacker (Me)

May 19, 2017
Freelance productivity is a lonely uphill battle. Let's talk about how to win it.

Freelance productivity continues to be an uphill battle for me. If you feel the same way, this article might help. Image credit: Jared Erondu via Unsplash

Before launching Smart Freelancer, I’ve asked a lot of people what I should write about. Freelance productivity came up quite a few times. How do you manage time? How do you work to meet tight deadlines? How do you break down a big freelance project? And so on.

Those are all important. And I would love to help you. There’s only one problem:

I’m just about the least productive person you will ever meet.

Yes, I’ve hit every freelance deadline I’ve been given in the past two years. Yes, the clients and PMs I work with now say things like “Oleg is so reliable, he is never late with a draft.” Yes, I manage to get something done for my clients every day.

But don’t be fooled. I’m the last person you should listen to about freelance productivity.

In fact, here’s a much better article you should read: How To Be More Productive by Working Less by Mark Manson. It’s probably the best thing I’ve ever read on the subject. Go read that instead. Seriously, I mean it. I won’t even be mad when you do.

Still here, are you?

OK, tell you what. While I don’t have straight-up “tips” or advice for you, I will share some productivity lessons I learned. Lessons born out of a life-long battle with my laziness, shitty work ethic, neuroses, and general jackassery. Lessons born out of necessity, because it was either learn to work like an adult or starve. Lessons that keep me (mostly) sane and high-functioning… even though I’m still every bit as bad at this whole “freelance productivity” thing as I’ve ever been.

They may or may not work for you. You’ve been warned.

Hey, it’s still not too late to go back and read that good article I linked above!

No? OK, let’s go.

Lesson #1. Use 2-3 interim deadlines, and enforce them

Here’s what my freelance work routine used to look like, back in those early, highly irresponsible days:

Step 1. Land a new project

Step 2. Goof off until the deadline is 24 hours away or less

Step 3. Receive a horrifying epiphany that this project is actually huge

Step 4. Do this:

Freelance productivity -- the Oleg Starko Edition

Suffice to say, I did not do my best work in those days.

Step 5. Finish the project late, or let it go down to the wire

In other words, I behaved like the embodiment of an unreliable freelancer. You know the type. From stories that go like this:

Client gives an assignment. Freelancer falls off the grid. On the day the work is due (if the client is lucky), freelancer emerges with subpar work.

But you know what?

For most clients and most freelancers, this kind of approach works just fine. They would never admit this to you, but it’s true. I know I was content with this soul-destroying vicious cycle because I couldn’t bear to invest too much time and energy in low-paying work. So in my head, it was fine to do what I did.

But we’re not here to do “fine”. We’re here to be better than 99% of schmucks who think that the ability to pester random strangers for money means they can freelance.

This kind of work ethic is fine for $5/hr. At $100+/hr, clients would (rightly) vanish into thin fucking air the second I pulled shit like that. Which is exactly what happened soon after I raised my rates. So I found myself with a choice:

A. Come back to my miserable rates just because I’m a mess who couldn’t hold a deadline (screw that).

B. Clean up my act and run my business like an adult, so I could actually survive on what I earned.

And, because at some point, one gets tired of cheap alcohol and eating rice and beans for every meal (what a diva, right?), option B it was. I started trying to do what the cool kids did…

I tried pacing myself. I tried doing most of the work upfront. I tried padding the final deadline by an extra 2-3 days, to give myself time.

These well-intentioned changes did fuck all. But here’s what ended up actually working:

For every project, I would split it up into meaningful chunks. For instance:

Bulleted list of ideas -> outline -> first draft -> second draft -> final draft

Then, I would assign an interim deadline to each of said chunks. And I would communicate that schedule to my client. This last part is critical, by the way.

Lo and behold: after I did this, it became impossible to goof off. At any given time, a deadline was looming, and a client was waiting for me to deliver. It hiked my freelance productivity waaay up: by keeping me accountable and on my toes, instead of farting around and complacent.

Lesson #2. Commit to one thing, and ONLY one thing, per day

I know.

Here you are, thinking about sending this email, and bidding on that job, and catching up on three different projects, and possibly updating your website, and checking ten more random items off your to-do list…

…and here’s this Ukrainian dickhead, a self-described procrastinator, and slacker, telling you to “just take it one thing at a time, maaan!” *takes a long drag on his imaginary joint*

Let’s all take a page from The Dude’s book.

But I mean it. To feel productive — and actually make progress — on most days, all you need is to do one big thing. And here’s the thing about big things:

They are much easier to accomplish when there isn’t a ton of other stuff on your plate.

Besides, when you knock off your most important item in the first couple of hour of your day, it’s the best feeling. It feels like a warm hug. In a bath. While eating chocolate (thank you for this phrase, Megan).

After that, you can either placate your lazy side and “kick dicks” for the rest of your day (an actual thing we say here in Russia)… or get the unimportant stuff done that much faster and guilt-free.

My personal “big rocks” vary day to day, but usually, they fall into 3 categories:

  • “Creative” client work, like writing a 1st draft.
  • Editing, because I hate doing it.
  • Pitching clients and writing proposals.

Everything else takes a back seat. If I can make progress on at least one task in one of those categories, I chalk it up as a win.

Who’s unambitious? You’re unambitious!

Lesson #3. Use the 2-minute rule to do a shit ton of freelance work (even if you don’t feel like it)

This is a simple rule that helps me write 10-15,000 words per week on the regular, even when I don’t feel like it. It could have been its own post, but I think James Clear has already written about it 1,000 times better than I ever will.

Here’s the gist:

Whenever you’re facing a big task, think about a tiny chunk that you can do in 2 minutes or less — and do it right then and there. For example, for this article (2,000+ words) I just wanted to write one paragraph to start with.

If it’s a small task you’ve been avoiding — hello, pile of laundry that’s been my cat’s makeshift bed for 3 days now! — commit to doing it for 2 minutes straight, with no interruptions. Time yourself if you need to.

Here’s what usually happens:

By the time the 2 minutes are up, you are done with the small task, or the small chunk of the big task. But 9 times out of 10 you feel like you can do more.

So you do more.

And then you’re like…

That’s how one paragraph of this post turned into 1,000+ words before I knew it. Because the truth is, you are seldom, if ever, so incapacitated by laziness that you can’t do any work at all. All it takes is to start the ball rolling, and allow the momentum to carry you further.

I used to apply the Pomodoro technique to achieve a similar goal, but committing to 2 minutes works much better for me. Possibly because working for 2 minutes sounds much less intimidating to my inner lazy bastard, as opposed to doing a hyper-focused 25-minute chunk of freelance work.

Lesson #4. Put your monkey brain on a tight leash

Can I tell you a secret?

Right now, writing this blog post is the last thing I want to do. Sometimes you just wake up with an inexorable desire to take your to-do list, crumple it up, and toss it into an active volcano.

But one thing keeps me typing away:

I didn’t give myself any choice.

From 9 am until 3 pm, I’ve blocked all distracting websites and apps on my laptop. And I locked myself out from making any changes to this routine for the next month.

So I can’t go on twitter to scroll through the billionth thread about how the entire world sucks now…

Or lose myself on TV Tropes reading about anime and manga featuring batshit crazy angels

Or go on YouTube and binge-watch videos of people playing video games…

Or succumb to the black hole of Netflix, where you blink — and suddenly it’s 6 am, and your eyes have shriveled up like 200-year-old raisins…

(Those are all real things I used to do when procrastinating, by the way. The part about raisins is an exaggeration, though. My peepers are appropriately moisturized and blue-ish green. Greenish blue. Whatever.)

Since I can’t do any of the above, I have a lot fewer distractions to grapple with — might as well do something useful, right?

To keep my monkey brain in check, I use two things:

  1. For day-to-day work: Cold Turkey. There are other apps and browser plugins that get the job done, but I like this one. It’s the only one I’ve stuck with for over a year now.
  2. For when things get all-caps BAD: Cold Turkey Writer. Once you set a word count goal or a time goal, it won’t let you quit. Literally. I love it and hate it at the same time. I don’t rely on it nearly as much as I used to. It’s a “last resort” kind of thing.

Lesson #5. For maximum freelance productivity, automate your next day

Blocking the temptations is a great first step, but it isn’t enough.

Sorry, Temptations. You're a threat to my freelance productivity.

I don’t know if I’m incredibly proud of this visual pun, deeply ashamed of it, or both.

If I don’t have my work laid out before me when I sit down at my desk, I will just twiddle my thumbs, read, or randomly surf the internet looking for excitement (I’m an edgy dude like that).

So the day before, I go through this checklist:

  • Set all the pages I need for work as my startup pages in Chrome — like so.
When it comes to freelance productivity, automation is key. Here's how I set my startup pages in Chrome.

As you’ve probably noticed, it helps a lot better with client work than it does with my blog.

  • Outline whatever writing I need to do, so I can just start typing and fill it out.
  • Write a simple to-do list for the next day (I use Productivity Planner, but a piece of paper will do just as well).
I hate to do lists, but this one keeps my freelance productivity at a decent level

The #1 item is my big one for the day, and the rest are usually optional (click to enlarge, if you need to)

  • If I feel like it, I might even queue up a work playlist, or write 250-500 words just to warm up.

Tip: to give your freelance productivity an extra kick up the pants the next day, finish work in the middle. For a copywriter, this might mean mid-sentence or mid-paragraph. For you, it might mean in the middle of coding something, or partway through a design. That way, you’ll have an easy time to pick up where you left off the following day. I stole this one from Josh Waitzkin’s Art of Learning, and I’m pretty sure he stole it from Ernest Hemingway. But it works, so who cares.

Lesson #6. Procrastination is your friend. Use it for good.

Not quite like this. Let me explain…

I don’t know if you’ve noticed this, but:

As a freelancer, only 10% of what you do involves actually sitting down at the computer and doing the work.

The other 90% is:

  • Learning about what needs to be done
  • Talking to the client about the project
  • Thinking about the best way to tackle it
  • Planning, ideation, and coming up with concepts

At least that’s the way it is for me. You might do a freelance project from start to finish in one sitting, in which case: kudos to you, why are you even here?

But I find that writing copy makes up a fraction of my total workload. So when I don’t feel like doing it just yet, I treat it as a cue from my brain that I haven’t thought this through enough and failed to prepare.

(Science backs me up on this, actually. Not that knowing this helps in any way.)

So I engage in something that Cal Newport calls productive meditation,” which is a fancy way of saying “thinking about work when you’re doing trivial shit” — like showering, walking the dog, doing the treadmill etc.

Surprisingly, it makes a difference. My best work comes when I look at the client’s brief in advance, let it stew in my head for a couple of days, and then sit down to write — sometimes on the day the first draft is due.

It can still be stressful, but this downtime gives me a critical buffer to learn how to do the job without slumming it. It might not work for you in the same way, though. Many freelancers I know only get comfortable with the project, and start to understand what it will look like, as they are working through it. Which is a 100% valid strategy.

Lesson #7. When all else fails, take a ride to Guilt Trip City

Paulo Coelho is a fascinating dude. Whether you love or hate his work (I kinda hate it), you gotta admit: he is crazy prolific and works hard. Which is why I was surprised to find out that his writing process depends on a weird spiral of self-loathing to work.

Every day, Paulo Coelho starts writing only after wasting 3 to 4 hours procrastinating. At which point he hates himself so much that he feels compelled to sit down and get to work. And once he gets started, he can write for 6 to 7 hours without taking a break.

This is amazing — and it runs in direct opposition to all the conventional advice on writing and productivity. Sure, the whole thing sounds a bit dysfunctional. But it works, as evidenced by approximately a fucktillion (that’s a technical term, you wouldn’t understand) of books Paulo Coelho has published.

Here’s why I am bringing this up:

Sometimes, I do the same thing. When I need to get some freelance work done, but my usual clunky, imperfect, idiosyncratic process is derailed,  the only way I manage to get back on track is by guilt-tripping myself and forcing myself to work through the night. Not even joking.

And, ironically, it works out (relatively) well. Some of my best-loved client work emerged in the wee hours of the morning: when I was too tired to care about being too sarcastic, or not making jokes, or sticking to conventional copywriting formulas. And that’s probably why I still do this to myself on occasion. 

I don’t endorse this particular freelance productivity lesson, by the way. It’s too masochistic, and not in a good way. I do it as a last resort, and you shouldn’t do this at all if you know what’s good for you.

What’s YOUR approach to freelance productivity?

And now I want to hear from you:

If, unlike me, you have an amazing work ethic and a great process in place to help you get things done, please leave a comment and let me know how on earth you manage it. And if you’re one of the unlucky ones, like yours truly, and you still struggle with being productive as a freelancer, I’d love to hear your perspective, too. Head down to the comments and let’s learn from each other.

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