Don’t Miss This Amazing Deal for Writers

My friends over at The Write Life have packaged together 12 courses and tools on earning money as a freelance writer. 

It’s called The Writer’s Bundle, and it’s one of the best learning opportunities for freelance writers you’ll see this year.

Wherever you are in your freelancing journey, this bundle will help you move faster and smarter.

You’ll recognize many of the creators of these products, including Stephanie Land, Elna Cain, Andrea Guevara, Yuwanda Black, Carol Tice and more.

The 12 resources available through this year’s bundle normally retail for $2,000+. But through this deal, you can get your hands on ALL of them for just $99. 

The catch? The bundle is only available until Wednesday, Sept. 16 at 11:59 p.m. PST. That means if you want it, you should check it out NOW.

Here’s what you get when you download The Writer’s Bundle: Freelance Writing Edition

✴️ Kickstart Your Freelance Writing Career, from Stephanie Land and Andrea Guevara (course value: $49)

✴️ Freelance Blogging in a Weekend, from Elna Cain (course value: $95)

✴️ How to Make Money Self Publishing Non Fiction, from Yuwanda Black (course value: $397)

✴️ Master Self-Editing, from Bryan Collins (course value: $297)

✴️ Breaking Into Media Q&A, from Kristin Wong and Alex Webb (event value: $99)

✴️ 38 Tips for Expert Writers on Medium, from Dave Schools (course value: $49)

✴️ ProwritingAid license, valid one year (editing tool value: $79) 

✴️ Pitching 101: How Writers Find Better Client Leads, from Carol Tice (course value: $97)

✴️ Turn Content Into Cash, from Heather Lloyd Martin (course value: $297)

✴️ 30 Days to Freelance Freedom, from Craig Cannings / FreelanceU (course value: $147) 

✴️ The Social Media Starter Kit, from Andréa Jones (course value: $297)

✴️ Productivity Power for Writers, from Tim Leffel (course value: $99)

If any of those courses sound like they could help you build your freelance career, go check out The Writer’s Bundle.

If you’re all “that sounds great but money is super-tight right now,” go check out all of the free tools and resources available at The Write Life, many of which were written by me.

P.S. If you purchase the bundle through my link, I earn an affiliate commission… but you already knew that. You also know that I’m only recommending this because I’ve worked with The Write Life for years and I know their training programs are some of the best tools in the industry. (I mean, I literally helped write some of them.) Sooooooo… go! Learn! Grow! Be the best freelance writer you can be!

Mid-Career Freelance Advice: The Slot System

Here comes some more MID-CAREER FREELANCE ADVICE, as requested!

Today we’re going to look at the Slot System.


So… when you’re an early-career freelancer, your “workflow management system” should be something along the lines of “send out as many pitches as you can and complete everything that gets accepted.”

At this point, you probably don’t know how much time it will take you to complete any of these assignments—first because you don’t know your own research-and-writing speed yet, second because you haven’t optimized your research-and-writing speed yet, and third because you don’t yet know which clients are likely to request a revision pass (or how to write the type of work that doesn’t require a revision pass).

You also don’t yet know how to time your workflow effectively. Some types of pieces go faster if you break them up into smaller chunks (today, I’ll write the summaries of each credit card on my list; tomorrow, I’ll write the section comparing the credit cards; Friday, I’ll write my introduction and conclusion). Other types of pieces go faster if you can write them all at once without any interruption.

Essentially, you start your freelancing career not knowing how long it takes to get stuff done.

And then, after a couple years of work, you do.

Which means you can start employing the Slot System.

I’ve referenced this particular organization tool in nearly all of my freelancing classes as well as in previous articles I’ve written for The Write Life and Lifehacker, but I haven’t framed it in exactly this way yet, so… here we go.

Every freelance workday has a certain number of Work Slots.

You can simplify this whole thing by having 1 Work Slot=1 hour, but as you’ll quickly learn, some hours generate more work than others. I can toggle very quickly between projects in the morning, for example, but tend to only be able to focus on a single project in the afternoon—and if I have an hour left over after I complete my work on that project, I don’t have the energy to start a new one.

In my case, mornings include four Work Slots (three project-based, one admin) and afternoons include two Work Slots (one project-based, one admin). The afternoon Work Slot is the longest of the six.

Each slot can include one unique type of work:

  • Drafting a piece
  • Revising a piece
  • Researching a piece
  • Conducting interviews for a piece
  • Email management
  • Invoice management
  • Etc.

My goal as a freelancer is to fill every available Work Slot without going over. This includes setting aside one afternoon Work Slot every week for slack/overflow work—the project that takes longer than expected, the interview that needs to be rescheduled, etc.

If I know in advance that a certain type of piece will take multiple Work Slots to complete, I need to assign it multiple Work Slots. This is why this system is more of a mid-career freelance thing than an early-career freelance thing; knowing how long it takes to get your work done is an extremely useful skillset to develop. That said, you can start using this system at any time. (Today, for example! It’ll probably take one Work Slot to set the whole thing up.)

If I have a bunch of unassigned Work Slots, it’s time to hustle up some more work. If most of my Work Slots are full, it’s time to start saying no to projects—or telling clients that I’d be happy to complete the project if I can turn in the draft on [DATE ASSOCIATED WITH MY NEXT CHUNK OF OPEN WORK SLOTS].

Right now, my September freelance schedule includes one unassigned Work Slot. (Yesterday, there were four unassigned Work Slots; then I got a request to complete a piece that I knew would take up three of those slots.)

This means that I can take on one additional project—if it can be completed in a single Work Slot—next month.

Let’s see if I end up sticking to that plan, or if I tell myself that I can totally take on a little more work, I’ll just squeeze everything into the overflow Work Slots, that’s why they’re there!

But that’s how you end up working an unsustainable freelance schedule—and as a mid-career freelancer, I should know better.

So… that’s the Slot System! Let me know if you have any questions, or if you use similar systems to organize your own freelance work. ❤️

Getting Some Slack Back Into My Schedule

So that big chunk of work that I needed to get done is now complete, and I finally have a little more slack in my freelance schedule.

This means, essentially, that I don’t have to be productive every minute of my workday.

That I have space for an assignment to take more time than anticipated.

That I have space for me, if I need to take more time than anticipated. (The assignment itself may take the two hours I’ve blocked off for it, but if I didn’t sleep well the night before and only want to give it an hour’s worth of work today, I can.)

That my evenings can include stuff besides “work” or “resting from work with books/TV/video games.” I’ve been putting off phonebanking for Andrew Yang, for example, because I haven’t had the energy to deal with phones and conversations.

I’ll also be able to go back to my regular YMCA routine—like, I never stopped going to the YMCA, but I did decrease my workouts by around 20 percent (in both frequency and intensity), and that decrease affected some of the other metrics my Fitbit and Exist apps track, and although I know WE ARE NOT OUR METRICS, or maybe WE ARE MORE THAN OUR METRICS, it’s interesting to see the ripple effects from all of these changes.

I mean, I think this recent freelance sprint was worth it. I’m now connected to two new clients who are offering recurring work, I got a bunch of bylines, I got to test an electric shock bracelet, and I’ll be getting some nice paychecks over the next month or so.

And, probably, the next time this kind of thing happens, it’ll be worth it again.

But I am very glad to get some slack back into my schedule. ❤️

Use Today’s Date As Your Freelance Invoice Number

I heard you wanted mid-career freelance advice, so here comes some VERY EXCELLENT MID-CAREER FREELANCE ADVICE.

Do not spend any of your precious freelance minutes keeping track of what invoice number you’re up to with each client.

Yes, I used to do this—because each client required a unique invoice, which meant a unique invoice number, which meant having a spreadsheet column where I noted that I was up to Invoice 15 with one client and Invoice 95 with another client.




I know you’re probably thinking “what about the FreshBooks and the QuickBooks and the BookBooks and all of those invoicing softwares I hear about on the podcasts? Won’t they, like, take care of that for me?

Well… maybe. But a lot of clients want you to invoice through their proprietary system, or through a third-party system like Kalo or Bill Dot Com, which means you have to log in to their system to invoice instead of using whatever tool the podcast recommended, and those systems do not automatically generate a fresh, unique invoice number with each invoice.

Instead, you’ll fill out your invoice and get the entire thing rejected because you already had an “Invoice 15” in the system, and then you have to do it all over again and that takes TIME, WHICH IS ALSO MONEY, I TELL YOU.

And then I was like “I’m just putting the current date on every invoice from now on.”

So if I were to invoice a client today, it would be Invoice #073019.

If I were to invoice two different clients today, they’d both get Invoice #073019, because it doesn’t matter if you send the same invoice number to two different clients. It only matters if you send the same invoice number to the same client twice, because then you will get an email from accounting if the invoicing software doesn’t reject you outright.

This system is also helpful because you can tell, at a glance, how long an invoice has been unpaid. If it gets to be October and you still haven’t received payment on Invoice #073019, well… time for accounting to get an email from you.

(Honestly, client-based invoicing softwares have pretty much eliminated late payments, so this isn’t something I worry much about anymore. But it’s still a good tip.)

So there’s your MID-CAREER FREELANCE ADVICE for the day, as requested.

If you have additional requests for advice, let me know. ❤️

On Integrating New Clients Into a Full Freelance Workload

I did a bunch of freelance work this weekend for the first time in, like, years.

In general, I try not to work on the weekends—and by “general” I mean “I can’t remember the last time I did”—but I ended up getting a pile of assignments this month and choosing to accept them all even though I knew I’d probably be taking on more work than I could complete in a 40-hour workweek.

This isn’t just because I’m trying to earn money while the earning’s good, though that’s part of it. I got approached by a couple of new clients this month, and I wanted to build relationships with them, so I said yes to the work they were offering (and agreed to start the work right away instead of, like, a month from now).

A long-term client is worth the occasional weekend project, just like a long-term anything you want is worth the extra work.

But your choices limit your choices, so it’s also important to ask yourself if what you’re working towards is worth what you’re giving up.

And in this case I said yes to the trade-off.

I had a request for more posts about mid-career freelancing, and I suspect these kinds of trade-offs are part of it. In my early freelancing days I took any assignment I could get because I needed the cash; now that I can afford to be more choosy, I choose assignments based on where they might take me in the future. Does this gig open me up to a new readership or allow me to establish/expand my areas of expertise? Does it connect me to editors whom I’d like to work with, and so on? Is there value in saying yes right away and getting those relationships started, instead of saying “well, I might have room for you in August…”

So yes, I worked this weekend, and I suspect I’ll do some freelance work over the next two weekends as well.

After that I should be able to move forward with a more balanced schedule — that is, spreading out my assignments instead of trying to do them all at once, since most of these new clients will want occasional work instead of daily/weekly stuff — and the benefits of new professional relationships and readers. ❤️

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.

How Do We Know When We’re Doing Our Best Work?

My NEXT BOOK draft currently stands at 14,526 words, and I wouldn’t consider any of those words my “best work.”

Not even the 310 words I shared with you last Friday.

It’s some of my most interesting work, and I think the plot is by far my best plot, and the questions it addresses are particularly immediate and relevant to the group of people whom I envision as its ideal readers*, but it’s not my best writing.


Which means it’s time to bring up the question that I promised I’d explore at some point: how do we know when we’re doing our best work?

I know that NEXT BOOK is not yet my best work because it doesn’t yet communicate what I want it to communicate to an audience.

That is: I know that NEXT BOOK is never going to be the story I felt inside my head, all at once, when I climbed the stairs of the Brucemore Mansion. That was kind of like… well, I’d been digging at this potential novel about Mars that wasn’t going anywhere, and my mom and I went to tour Brucemore over Christmas because they had all the decorations up, and I saw a staircase that reminded me of the staircase in this mansion that I dream about on the reg, a big old house with a bunch of secret doors and secret rooms, and I was all I want to write about a big old house with a bunch of secret doors and one of the doors leads to another world and the person who knows that has to decide whether she’s going to go.

And then I had to work out the rest of the story, because that’s really only the exposition. The decision process can’t take much more than the first third of the book, because you can’t really dangle a portal fantasy in front of your reader without eventually having your protagonist go through the portal.

So that’s what I did during the rest of the Brucemore tour, in a very general “this is what I want it to feel like” way, and I also figured out who my three main characters were and what they wanted, and then I went to the Maggie Stiefvater Portraits and Dreams seminar and started studying plot and made everything a lot more specific.

But it’s still not specific enough. With this draft, I’m putting down all the little pencil markings you do before you trace over the markings you want with ink. I’m literally writing down three different ways of describing something and telling myself I’ll pick one later.

(This probably means my actual word count, of “words that form the story and don’t just explore different ways of writing something,” is closer to 14,000.)

So… NEXT BOOK is not my best work (yet), and part of that is because I still have a lot of work left to do.

What about my freelance writing?

I still think that it all comes down to “does this communicate what it set out to communicate,” which in freelancing often includes “does this piece fulfill the client’s specs?” Did I successfully write a 1,000-word article that helps readers decide whether to sign up with Hilton Honors or Marriott Bonvoy?

When I was writing for The Billfold, I got instant feedback on whether my writing communicated what it was supposed to communicate — because if it didn’t, I got dozens of comments either asking questions about the piece or informing me of something I’d neglected to consider. I also had access to the back end analytics stuff, which meant I could see which articles were getting the most views. (This usually means you’ve got a headline that communicates what it’s supposed to communicate, i.e. “HERE’S WHY YOU SHOULD READ ME!”)

I don’t get that kind of detailed analytic information from my current freelance clients, and many sites have stopped doing comments altogether, so it’s harder to tell whether my current posts are doing what they’re supposed to do. Luckily, by this point I’ve had a lot of practice at this kind of writing. Plus, I have a new metric: am I still getting hired? Are my current clients asking me to contribute more work, and are new clients reaching out to me?

At this point, you might be asking “what about, like, beautiful prose?” I enjoy a well-turned phrase as much as the next person, but I stand by my initial assessment that it’s only beautiful if it’s understandable. Even nonliteral writing — our poets, our James Joyces, etc. — is understandable in the sense that it evokes an emotional response in the reader and by doing so communicates what it was intended to communicate.

We get Jabberwocky, even though Lewis Carroll made half the words up.

If we don’t get it, maybe it’s not for us. Maybe we’re not the ideal audience, e.g. “Pixar’s ‘Bao’ Draws Mixed Reactions From White Peeps Who Don’t Get Asian Culture.”

If nobody gets it, maybe it’s not for anybody. Maybe the writer was writing just for themselves and not for an audience. Maybe it wasn’t the writer’s best work.

One more note before I finish this up: when I teach my How to Freelance class, I ask my students to draft short posts “to spec,” and many of them use this assignment as an opportunity to show off the most beautiful and/or clever phrases they can come up with. The problem? Online writing favors clear, simple sentences. I’ve worked with clients that have required me to submit text at no higher than a seventh-grade reading level, because they want to make sure it can be understood by as many people as possible.

In this case your definition of “best work” may be different than your client’s definition — so go with theirs, and find an hour every day to write the glorious, elegant, delightful, quippy little phrases that may someday end up in your novel or memoir or poetry collection.

Make sure you write down every one that pops into your head, so you can go back and choose your favorites when you edit the draft. ❤️

*Ideal reader for NEXT BOOK: the Millennial who totally wishes they could go to a fantasy world if they had the chance, but might not actually say yes if it were offered because they’ve, like, got responsibilities. (Or, more specifically: readers between ages 23-38 who loved Narnia and Harry Potter and The Magicians and want a book where a grown adult in a time period a lot like our own gets the opportunity to travel to a magical kingdom.)