Going all-in on the cult of productivity

Falling into the abyss, figuring out what freelance writers actually need and finding my way back to reality.

Devon Delfino
Feb 24, 2018 · 8 min read

I’m a writer, and that means I’m supposed to thrive on creative chaos. But after a couple months of freelancing, I found myself floundering. So I started reading the articles I’d written off in the past.

You know the ones: “This productivity hack will save you X hours a day.” Or “The one thing you’re not doing that’s stopping you from greatness.” Or “I changed my morning routine and I’m never going back.”

I figured some of the advice had to be worth a shot. But I don’t like to do anything halfway. One-off articles weren’t going to cut it, I decided. I needed to go method.

So I immersed myself in that world.

I read every article, scientific study and blog post that came my way. I signed up for newsletters. I attended webinars. I took notes, processed all the information, reevaluated how it would apply to freelance writing, restructured and reshaped it to my current needs and tried to plan ahead for my future needs. I made spreadsheets. I set alarms on my phone.

I was all-in, and I was ready for anything.

And after all that, I discovered something unexpected: I loved it. I loved celebrating every tiny victory with an equally tiny reward. I loved creating color-coded systems. And most of all, I loved spreadsheets.

Yes, spreadsheets.

It all started with one dedicated to tracking my pitches. It had so much information crammed into it: when and where I sent each pitch, if and how I followed up, suggested headlines, the editor’s name, the proposed word count, potential pay and general notes. It was ridiculously thorough but 100% necessary, at least according to my research.

But one tab couldn’t be the answer to all of my problems, could it? If that were the case, that information wouldn’t be scattered across the internet, like puzzle pieces waiting to be found.

So I added another tab for editors at the publications I was pitching. That one took a couple of days to fill out because I had to first compile a list of publications to pitch (which ended up being close to 100). And researching email addresses took way more time than it should have. But at least it meant that my carefully crafted pitches wouldn’t be buried in unmonitored, general inboxes, never to be seen again.

Should I have stopped there? Could I have stopped there?

No. Because I soon realized that I needed a high-level view of my business. I was a business-owner now, and I needed a seriously robust spreadsheet to succeed.

One spreadsheet to rule them all.

My current methods just weren’t cutting it, not if I wanted to be a “real” freelancer. (Or so I read.) I needed to break down my goals into bite-sized steps. I needed to set long-term goals. I needed to create a detailed weekly schedule. And I needed to establish rewards for meeting self-imposed deadlines (because those are the hardest to meet).

Then I found out that I had been neglecting my marketing obligations. (“Thou shalt do 5 marketing-related activites per day,” apparently.) So I made up another spreadsheet for that. But I gave it rainbow-gradient columns, so that made it fun, right? (Ok, kind of.)

I kept finding reasons to add new sheets, columns and tabs to meet my ever-expanding needs.

That’s how my two-tab spreadsheet turned into a behemoth that I nicknamed “Eagle Eye.” It was massive, untenable. And it took my computer forever to load (ok, 10 to 15 seconds).

But how else would I ensure that I was on track with my goals if I wasn’t constantly checking in? I was the only person who cared if I stuck to my schedule and met self-imposed deadlines, and accomplished my goals. That makes it easy to let bad habits get the best of you, and I couldn’t let that happen. But I still wasn’t satisfied with my progress.

Maybe I’m being too single-minded. Maybe I should track financial goals and other non-work related goals. I mean, self-improvement should transcend work, right?

Dear god, what was I doing to myself?

Not only was I adding new tabs, I was expanding each individual sheet to make it more expansive and detailed. I was adding categories and trying to plan for every possible scenario. It didn’t matter if it was realistic or not, I wanted to be prepared for everything.

And if I’d learned anything during the recon stage of this experiment, it was that the details would make or break you. So I repeated the goal-setting exercise for my income, health, self-reflection, wellness and social goals, planning out milestones for the next six months.

And before I knew I knew it, there went yet another day, sacrificed to appease the productivity gods.

But I could see that my systems and spreadsheets were getting in the way of my actual work. I wasn’t writing as much as I wanted to. I wasn’t meeting all of my goals. And that carefully crafted schedule just wasn’t matching up to what I was doing.

So I started tracking how much time I spent updating everything.

The irony is palpable, I know. But that extra bit of tracking actually did turn out to be useful. It showed me that my love of spreadsheets had grown a full-blown obsession. Of course I had a feeling that was the case, but it’s easy to deny the obvious when there’s no data to back it up.

One bizarre new behavior it revealed: Sometimes I’d open my master spreadsheet and stare at it for a few minutes. I didn’t need to update it, I just wanted to look at it.

I was spending time appreciating every micro-progression toward my goals because it felt good to have some form of validation at a time when it felt like I was constantly going up against a brick wall. At the end of the day, I was using the experiment to avoid the hard work of writing.

And when I discovered that almost a third of my time was dedicated to tracking my work, I knew something had to change.

The trouble with productivity exercises is that they feel like necessary work.

Freelancing can be rough. It’s all on you to get everything done and there’s no one there to whip you into shape when you start to slack or try to justify a five-day weekend with the old standby, “I’ve been working nonstop for what feels like forever. I deserve this.”

And even though a lot of successful freelancers will talk about their tough early days, it will never be enough to prepare you for the realities of the lifestyle.

So when someone tells you about a work-hack they’ve devised that’s guaranteed to make your life easier, it’s tempting to take them at their word and ignore your better judgement.

I mean, I was taking advice from people I didn’t know, who probably had very different habits, work-styles and personalities than myself. Of course their tried-and-true, too-good-to-fail methods weren’t right for me.

But I knew that I still needed some level of structure to keep me going.

So I took a look at what was actually working for me.

I found that there are really only a few lists I need to maintain to keep my work organized:

  1. Pitches: It’s useful to track the headline, send date and current status (sent/waiting/followed up once/followed up twice), but I don’t need much else to make this work for me.
  2. Editors/contacts at publications I want to pitch: This list is essential for me, even if it did require a lot of time to create as well as a bit of ongoing management. Here are the columns I found to be most effective:
  • Publication
  • Topic keywords (for easy searching when I have an idea for a story but I’m not sure what publication would be the best fit)
  • Name (I’d also include their job title here)
  • Email (I used the free version of Hunter in combination with LinkedIn to find the email addresses that weren’t available on the publication’s website. I also stuck to any email formats that I came across, like firstname.lastname@publication.com)
  • Response time (to help narrow down my options for timely pitches)
  • Notes/Source (this is where I keep links to submission guidelines as well as information about how I came across the publication or editor)

3. Payment information: Invoice date, current status, and taxes — because I’m the only one actually tracking that now and I don’t want to get audited.

4. Completed assignments: Publication, link, and topic (again, this makes for easy searching when I’m pitching a new publication and I need related clips to include in the email).

Lessons learned along the way

Here’s what I found works (or doesn’t work) for my particular brand of contradictory personality traits:

  1. My “creative process” needs an occasional dose of mindless distraction to function.
  2. I like to switch up the type of work I do every day. There are days when I pitch like crazy, and some days when I write nonstop, but then there are other days when I focus entirely on reading. I see no reason to force myself to do the activities that leave me feeling exhausted (read: pitching) every single day, just because it’s recommended by experts.
  3. Artificial deadlines and quotas only work for me if I’m 100% invested in them and optimistic I can meet them. For example: I made a “stretch” goal of sending out 7 pitches per week. But I didn’t have any basis for it other than it had turned up in my research. And, as I said before, pitching is exhausting. So every time I went to write a pitch email, I had this sense of dread. I turned to multi-tasking to make it more bearable. But that only made each pitch take longer to complete. That negative feedback loop made me abandon the goal altogether.
  4. Weekly goals are overkill. Enough said.
  5. I imagine pitch/response scripts can be useful for some people, but they just slow me down. Don’t get me wrong: It’s good that I have an idea of what I want to say in recurring situations (pitch/followup/response). But it’s better to create a new draft than try to work around one that isn’t quite right for the job. And it keeps me from sounding like a weird, humorless robot.

These are all great things to know. But I wish I’d been more thoughtful about this experiment from the get-go, instead of letting myself fall into the abyss.

I’m not going to stop trying new things and experimenting with ways to be more productive. But I will put a limit the amount of time I give each experiment and be mindful of how useful it actually is, how much effort it requires and weather or not it suits my personality and lifestyle.

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