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The Most Productive Month Of My Life

Can a disorganized freelancer and night-owl stand-up comic transform her productivity in 30 days? Find out.

The Most Productive Month Of My Life
[Photo: Epoxydude/Getty Images]

There are two kinds of people: Those who thrive when things are in order, and people like me, who thrive in a state of chaos.

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I’m a freelance writer and stand-up comic, which means I juggle two separate lives: Day Lindsay and Night Lindsay. There’s a lot of task juggling—producing comedy shows, filing freelance stories, keeping up with the endless flow of direct messages, Facebook status updates, Slack messages and emails.

My workflow has as much order a game of junior high dodgeball. It’s not my fault. For years I worked in a newsroom where I was not in control of my workflow. When you work in breaking news, everything is priority. There was even a sick pride in getting things done just under the wire–the messier and more work it took, the more badass it felt. This was not a good model for professional life.

When I left full-time journalism, I took a job in a more corporate environment and was soon stymied by the very idea of prioritization and productivity. The only speed I knew was extremely fast and all at once. It took me months to figure out what was really priority and what could be left until later in the day or week.

But lately, I’d let things slide. I’ve gone from carefully ordered lists to handling my tasks as they come, forgoing order and re-embracing lunacy. Could my creative and haphazard task juggling be improved by extreme order? To find out, I committed a month to being my most productive self. For 30 days, I would put each of the 15 productivity habits featured in the November issue of Fast Company into practice. Here’s how it went:

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Productivity Habit No. 1: Carve Out And Ruthlessly Protect Just 90 Minutes—20% Of An Eight-Hour Day—For The Most Important Tasks

Success or Failure? Success!

To accomplish this, I went back to a system I learned from my brief period working for a corporate PR firm. I dubbed it the Axis of Evil: Every day I made a chart, dividing my tasks into quadrants labeled Do Now, Do at Noon, Do This Week and Misc. Life Stuff. I crossed off tasks as they were completed, and made notes on progress. I felt immediately more productive and felt better about spending the last hour of my day agonizing over what jokes to tell at a comedy show that night.

Productivity Habit No. 2: Declutter Your Desk

Success or Failure? Grudging success.

Like Linus from Peanuts, my desk clutter is my professional security blanket. I am a desk hoarder. I like to surround myself with papers, empty coffee cups and water bottles, napkins, notebooks, gum wrappers, and books. Every day, I add more trash to my Fort Awesome. It’s where I make the genius happen! For some reason, I’ve always been skeptical of colleagues with too-clean desks. To me, a desk overflowing with detritus was clear evidence that Serious Work Was Being Done.

At the beginning of the month’s challenge, I cleared away all the accumulated scraps of paper, notebooks, and other random things that had landed on my workspace and stayed. This was quite humbling for me. I felt a bit ashamed once I began hauling papers and old coffee cups to the trash. During the month, I managed to keep my office desk space much cleaner, much to the joy of my colleagues who had been politely tolerating my creative mess. My home office was tougher to maintain. Clutter kept piling up, and eventually I moved onto my couch to work. Despite my prejudice against a tidy desk, there was no denying it. A clean desk made me calmer and gave me more room to think and be creative with my thoughts. Working at a tidy desk also eliminated visual distractions and allowed me to focus on tasks.

Productivity Habit No. 3: Don’t Work More Than 49 Hours A Week–It Makes You Less Productive

Success or Failure? Sadly, a failure.

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This started out as a smashing success. At the beginning of the month, I was starting my Day Lindsay work early, knocking out tasks quickly and finishing up early. At the halfway point in the month, it got complicated. More tasks that couldn’t be put off began to come in midday, and I found my Day Lindsay work creeping later and later in the afternoon. I’m part of a small team, so I wasn’t able to delegate tasks without worrying I was adding work onto a colleague’s plate. I found myself longing for the early days of the month when things more organized. When you work for a startup, it’s hard to “work less” when there’s always more to do. It’s a great idea and it works–when you know and feel confident that your agenda won’t change over the course of the day.

Productivity Habit No. 4: Turn Off Your Smartphone

Success or Failure? Small success, bigger fail.

This may be the saddest phrase ever uttered by a human, but my phone is my life. Work assignments come in via email, comedy dates come in via messenger, and I get texts all day long from my friends and family. My phone is also the bane of my existence—it keeps me up at night, I’m always checking Facebook or one of my three Twitter accounts. I call it “phonework”—it makes you feel busy, but really, you’re utterly unproductive.

The good news is that when I hid my phone, I didn’t actually miss it that much. The bad news is that since I have a MacBook, it syncs everything with my iPhone. So all my texts came through via iChat and I still received Gchat beeps. And while I wasn’t looking at Twitter or Facebook on my phone, I still checked it on my laptop—not helpful for productivity.

Productivity Habit No. 5: Forward Incoming Emails To Your Phone To Check Later

Success or Failure? Immediate failure.

Ignoring emails is just not an option for me. I’m consulting with a company that’s based in Stockholm, and the time difference means I need to be around to answer emails when they arrive in my inbox. Besides, I’m constantly receiving alerts on Slack, which is just as distracting as email. At least emails can usually sit for a few minutes in your inbox—Slack messages have the expectation that they will be answered right away. Also, I’ve realized that when it comes to my personal email, I need to answer things right away, or I forget to answer them at all. It’s hard to maintain work-life balance when your friends stop speaking to you because you forgot to RSVP to their baby showers. This could be a great idea for workers that have strict barriers between their work and personal email. For me, they’re one and the same. I just couldn’t risk missing an email.

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Productivity Habit No. 6: Focus On High-Value Activities

Success or Failure? Mostly a failure.

I found this concept hard to put into practice. Do you value the project that’s going to make you the most money over the project that makes you the happiest? Also, when you’re a freelancer, there’s simply no one to delegate to. You’re a one-man band. However, this challenge did inspire me to email my supervisor for task and role clarification so that I felt confident that I was working on the most important tasks for the company, so I won’t call it a complete failure.

Productivity Habit No. 7: Have Better Meetings By Making An Agenda, Banishing Distractions, And Making People Move Around

Success or Failure? Success, success, fail.

There’s nothing I hate more than boring small talk and little jokey asides on conference calls. Team calls are huge time sucks in which no one is having any fun. When you work remotely, it’s essential to have an agenda on a call so everyone can prep and arrive to the call with answers and next steps. My colleagues at my day job work on Trello, which serves as our agenda for our morning call. During the month, I made an effort to look through the board before the call and to own all the tasks that I’d completed and offer insights on next steps. This definitely made meetings go faster. I also felt ahead of the curve and gave my team the impression that I was on top of my game and ready to move.

This also made the parking-lot idea easy to implement: I felt more comfortable telling my team to move less urgent tasks to the next day or week. The team seemed to be having its own productivity challenge–whenever someone had an idea that wasn’t going to be able to be addressed on the call, we put it on Trello for the following week, when we had more data or thoughts on why it was or wasn’t a good idea. Calls ended early, everyone got back to work faster. Success.

But when it comes to walking around while on team calls, it can be easier said than done. Easy when dialed into a phone line, tough when you’re on Skype. I want my colleagues to think I’m professional, not making an attempt to imitate the camera work in a Spike Lee movie.

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Productivity Habit No. 8: Sleep On The Job

Success or Failure? Epic Fail.

Attempts to nap in my shared workplace made me too self-conscious. What if someone needed to use the couch and there I am, napping like a vagrant? Putting my head in my arms to sleep on my desk just made me feel like I was back in kindergarten—and I couldn’t even nap then! On days when I worked from home, “power naps” became two-hour “epic sleep marathons.” I woke up groggy, confused, and feeling the opposite of productive.

Productivity Habit No. 9: Avoid The Biggest Productivity Killers Like Social Media And Texting

Success or Failure? Mostly an enormous fail.

This was the part of the challenge where I stumbled the most. While I was able to put away my phone, so much of my life happens on social media that it was incredibly difficult to ignore alerts. For example, most of my standup comedy bookings come to me via Facebook Messenger. If I ignore it, they might offer the spot to someone else. Emails also come with offers of freelance opportunities, so they’re hard to ignore.

I’m on Twitter, following breaking news, and I often click on articles that interest me, totally derailing my workflow. When it comes to gossip, I did okay, but only because I have only single colleagues at my share space. Gossip has been a big problem for me in the past. It’s so easy to get sucked in, and not only is much of it destructive to group morale, it’s also a huge waste of time. I don’t miss the negativity of working in a traditional office for this very reason.

Productivity Habit No. 10: Prioritize Your Everyday Choices

Success or Failure? Big Success!

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I tweaked my Axis of Work Evil to create a separate section for super-fast items I could cross off quickly. I did those at the beginning of the day, and felt a big weight being lifted off my workload in just 20 minutes.

Productivity Habit No. 11: Get Around 7.7 Hours Of Sleep A Night

Success or Failure? Success—mostly.

After a normal workday, it’s easy to slip into bed with book or a crossword puzzle at 11 p.m. and get around 7.5 hours of sleep. But after a stand-up comedy show? No way. I come home amped up, and I need at least another hour or two to wind down. But I need to be up and ready for morning calls by 8:30 a.m. at the absolute latest. So that means some nights, I’m running on four to five hours of sleep.

The first part of the month, I had relatively few comedy shows in the evening–sad for me, but good for sleeping. Waking up is always hard, but after two weeks of 7.7 hours of sleep each night, I felt pretty consistently okay throughout the day, only needing one cup of coffee to get through the day. As my comedy gigs began to pop up on my calendar, I started to get home later, and my average sleep time plummeted to under five hours. At first, I didn’t feel much of a difference since I had to be ready and alert for my morning call. But by the end of the month, I felt like I was dragging by midday. And worse, I couldn’t get to sleep at night, either. Having an inconsistent sleep schedule can definitely make you feel unproductive, especially if you’re already fantasizing about your pillow before lunch. I’ll definitely try harder to keep a consistent sleep schedule when I can, but on nights when I’m out telling jokes until midnight, it will remain a challenge.

Productivity Habit No. 12: Choose A Workspace With Natural Light

Success or Failure? Some success.

We cannot choose where management puts our desks. My spot in my share space is in the middle of a room, so my access to sunlight is limited. When I’m working from home, I try to sit near the window, and I find that the natural sunlight puts me in a slightly better frame of mind to get my work done than just marinating in florescent lighting. Natural light makes me feel more like a living organism and less like a human laptop accessory, so the benefits make sense to me.

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Productivity Habit No. 13: Give People Positive Feedback

Success or Failure? Success!

While I don’t have any subordinates to motivate, I did spend some extra time with a younger colleague and offered her extra cheering-on and assurances that she was doing a great job. She thanked me the next day and seemed happier to be at work and more excited to take on new challenges. Did this make me more productive? I can’t say, but it certainly made me feel good.

Productivity Habit No. 14: Frame Complaints With Potential Solutions

Success or Failure? Success!

Freelancing is a tricky balance of pleasing your client, but also making sure that you’re not doing more work than you’re getting paid to do. I had a situation on my hands where my tasks were growing, but my compensation wasn’t. I didn’t want to complain to my boss about being overworked since the whole team was pitching in and working hard. Plus, I knew that their budget was a concern. Instead, I flagged the situation to my boss and outlined all the tasks that I was being asked to do and showed him my original scope of work. I offered him two options: Either we could negotiate an hourly average rate, or he could take certain items off my plate and suggest other team members who had more time and resources. He appreciated that I was keeping costs in mind, and he agreed to reassign the tasks. I didn’t get a wage increase, but at least I was back to working my agreed-upon hours.

Productivity Habit No. 15: Get At Least 20 Minutes Of Exercise A Day

Success or Failure? Success, but with reservations.

I made a definite effort to hit the gym in order to break up the day during my challenge month. On days when I work from home, I’ve been getting up early, doing my client work, and then going to the gym during lunch. Then I come home, finish up, and then begin planning my evenings, which can include dinner with my husband or heading out the door for a standup comedy show. I’ve never felt better when I do this—the only thing is that it only works if I can do it in the middle of the day. Getting up early is out of the question, and going after work means I don’t get home until almost 8 p.m.

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So Was This The Most Productive Month Of My Life?

I was an unusual candidate for this challenge, because I’ve got two separate but distinct lives that complicate each other. It’s tough to be productive when you’ve got a day life and a night life, something that many freelancers can surely relate to. But many of these tips were helpful, especially keeping up my organized Axis of Evil, midday exercise when I can, and being encouraging to coworkers. Everyone needs kindness, even stand-up comics.

Want to try living the most productive month of your life? Here are all of the tips that Lindsay followed.

Lindsay Goldwert is a freelance journalist, stand-up comic, and ghostwriter. Her work has appeared in the New York Daily News, Slate and many others. She lives in Queens, New York.

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