work + Life
after 3 years of trial and error
by Brittany Taylor
published September 20, 2018
¶ Running your own business is hard in a lot of different ways. Some are predictable (think: finding your first clients). Others aren’t. For me, one of those “others” has always been settling into and sticking with a daily routine.
I don’t know why. Maybe it’s the free-ness of freelance life. Maybe it’s my brain, leaping toward a half-dozen ideas at any given moment. Maybe it’s sheer lack of willpower. Maybe it’s the come-and-go throws of anxiety and depression. Maybe it’s a combination of all these disparate elements.
For whatever reason, I’ve yet to make a daily routine stick—not since I went out on my own.
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Not being able to stick with a daily routine sounds like a silly thing to feel guilty about, but I do. It seems so easy! Create a plan. Stick with it. That’s all there is to it, right?
Looking through social media, my fellow online bosses seem to manage it without a problem. Wake up with the sun. Shower, brush teeth, eat some sort of acai smoothie granola fruit bowl thing. Empty inbox. Social media. Client calls, client work. Rinse, repeat.
So, what’s wrong with me? Why can’t I manage a daily routine, too? Why can’t I get myself to follow a productive schedule?
I ask myself those questions every time a newly shaped routine bites the dust. And every time I shrug and sigh, unable to come up with any definitive answers, I feel it. I feel the guilt.
One of the perks of the freelance lifestyle is that you’re free to do whatever you want, whenever you want to do it. Well, sort of: You have to finance it. To do that, you need to be productive. As Forbes and Business Insider are perpetually happy to tell you, successful people attribute their productivity to their routines.
I get their point. I was a successful student. I nailed the school routine. It was after graduation that my routine began to crumble.
What happened? The responsibilities I shouldered at The Magazine created a never-ending to-do list. The first 3 months, I was OK. Once I mastered the basics, though, and my workload increased, I was in a situation where the work was never done.
Back in school, the work was finite. There were classes. There was homework. And that was it.
At work, at both The Magazine and as a freelancer, I could always be plugging away at a project. It’s like I’m always on a boat in the middle of the ocean, trying to get to shore. The mindset becomes: What’s the point of paddling for another 5 hours today if I’m not going to see any forward progress tomorrow? There are so many steps, so many tasks to accomplish, that I begin to lose track. I can’t remember how to put one foot in front of the other.
That’s where the routines start to fail, and that’s where the guilt creeps in. You know there’s work to do, but you can’t motivate yourself to do it because...why bother? Or, you know there’s something to do, something you’re forgetting, but amid the mess of must-do’s in your brain, there’s no way to sort out which ball is about to be dropped.
That’s what it feels like for me, anyway. I become overwhelmed. I lose motivation. I start to flounder.
Guilt. Guilt. Guilt.
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When the work is never done and you’re losing control of the one thing that keeps a roof over your head, you need to find a way to dig yourself out. For me, that meant building a ladder—creating structure, even though one thing I adore about freelance life is that it is structure-less.
I tried block scheduling, where you have activities doled out to different chunks of time.
I tried batch scheduling, where you complete a bunch of one activity in one long marathon.
I tried time tracking, where I logged how many hours and minutes I allocated to every task.
I tried setting alarms. I tried the Pomodoro technique. I tried waking up early, and I tried working late into the night. I tried challenges. I tried bullet journaling and sticker charts and reward systems.
I tried and I tried and I tried for 3 years. Three years! That’s how long I’ve been chipping away at this downward spiral that is my schedule dilemma.
And you know what? After all that trial-and-error, I’ve come up with a few things that I like. I’ve discovered a few systems that improve my productivity and keep me on track as I work to accomplish my goals, step by step.
The thing is, I wouldn’t be where I am now without every single experiment. That’s the hard part about it. There’s no one right way out of a downward spiral. You have to try and fail before you start scrabbling up and out of the hole.
I’m not 100-percent there yet. Sometimes, I still slip back into my old, bad habits. But I’m doing better—and better is always my goal.
Here’s what I’ve learned so far:
And my routines make a difference on my emotions, too. I naturally move through periods of high anxiety, depression, and obsession, all of which impact my work and my willpower in different ways. When I’m feeling super high, I’m less focused, and when I’m feeling super low, I’m less motivated.
However, no matter how I’m feeling at a given moment, when I get myself to sit down and move through the motions of my routine, I tend to even out and work productively. Win-win.
I find that my most useful systems—the one that I stick with—are created with goals in mind. In the beginning, when my routines failed, I was trying to dictate a routine based on what I thought I should be spending my time doing (and what other people were spending their time doing).
When that didn’t help, though, I realized I was going about it wrong. I needed to design my routines purposefully. I needed to use them to solve a problem. The problem wasn’t the work. For me, the problem was my mindset. I needed to change my frame of my mind from play or sleep or lunch, to work. Once I did that, I’d have the momentum I needed to push through my to-do list.
Some things don’t come naturally to me, like waking up early. Sometimes, I have to do those things anyway. But when I don’t have to, I’ve learned that I shouldn’t force it. Instead, I should lean in to what works so that I can create the conditions that best foster creativity and productivity for me.
That means waking up naturally, often 11 a.m. That means eating lunch 2 or 3 hours after I get up. That means doing more rote tasks earlier in the day and saving late afternoon and evening for more intensive work, like brainstorming, strategizing, and writing.
Before I pull back the curtain on my modest morning-ish routine, I want underscore one fact: this is my routine, crafted for me based on my needs and my goals and my likes and my dislikes. I’m not emphasizing that it’s mine because I don’t want you to try it. Try it if you want to! But I want you to remember that what works for me at this moment in time might not work for you. And that’s OK.
Wake up naturally, usually between 10:30 a.m. and noon
Quickly scan email, texts, and voicemails to see if there are any fires to put out
Go to the bathroom
If I feel bad, climb back into bed, possibly with a few Tylenol. I’ll almost always think about my day, find my focus and motivation, and get back up 10 minutes later. If I don’t, I fall asleep and feel better when I do get up.
Brush my teeth and wash my face while listening to a podcast
Make my bed, put away stray clothes, and open the curtains
Sit down at my desk, in my pajamas, with the to-do list I made the night before
Answer emails and respond to any new inquiries and direct comments or messages on social media platforms
Complete daily social media tasks, including posting a daily writing prompt on Instagram and pinning manually
Complete any quick client or personal tasks, like website maintenance or edits
And that’s it. After lunch, I move on to larger projects, usually only one or two in an afternoon. Sometimes, I’ll write my own blog posts, but right now, I’m focusing on client work and squeezing in my own content creation at the end of the work day when I can.
I mentioned guilt earlier. I hate guilt. Guilt drags me into depression. I start blaming myself and making excuses and avoiding the work I need to do, which triggers more guilt.
So, one essential element of my routine is the fine print. It’s a footnote that says my daily routine isn’t a daily must-do. Sometimes, I have to wake up, brush my teeth, and walk out the door. Sometimes, I have to wake up and take the dog to the vet. Sometimes, I have to wake up and play tech support to my parents.
What I’m starting to love about freelancing is that it lets me be flexible with my routines. Sure, I can wake up and start the daily routine and go about the work day as normal. But I can also start it later. I can do it when I can and shrug it off when I can’t.
And that feels good, friends. It’s not perfect, but it’s better.
My name is Brittany, but my friends and clients call me "Britt." Online small business owners hire me to create content strategies and write their blog posts, email newsletters, and social media updates. I work with bosses around the world from the marshes of Charleston, S.C.