Working as a freelancer requires the self-discipline to sit down and work when adventure calls.
As much as I would love to call myself “retired at 50,” I’m not. Yes, I’ve planned ahead and prepared ourselves for this adventure by setting aside a little money to cover our basic living expenses. I intend to continue to work as a freelance writer while we travel.
Fortunately, I’ve trained for this. Over the last several years, living in a Colorado mountain paradise – birds, chipmunks, and deer frequently distracted me. Sorry, but when a herd of 32 mule deer wanders into your yard, all work comes to a screeching halt.
The key is learning to prioritize your time, set daily goals, and mind your task list, so when nature or adventure calls, you don’t feel guilty taking a break.
Prioritize Your Time, But Go With the Flow
Personally, I’m a morning person. I love the wee morning hours before the rest of the world wakes up. It’s quiet. It’s peaceful. But I also know I can’t write anything until my brain wakes up and gets inspired by something. So, rather than wake up and try to jump straight into writing something, I read first.
I read today’s news, maybe a few blogs on Medium, and I scroll through social media for a little while until something triggers an idea. (These days, it usually doesn’t take long.) While traveling, maybe I’ll read my notes from the previous day’s excursion, or spend some time looking ahead to find our next destination.
The moral of the story is this… pay attention to what works for you. Don’t set your schedule based on some article you read about some random celebrity’s idea of a perfect day. Do what works for you. Maybe you’re a night owl who doesn’t really get inspired until the moon comes up and can’t imagine waking up at 5 am every day. It doesn’t matter what your preference is, but learn to use your time so that it works best for you.
Set Achievable Daily Goals
Show of hands – who’s a lister? I’m a lister, and I blame my mother. She left lists of things for me to do while she was at work in the summer, and it stuck.
But for years, I was doing it wrong. If you have more than 10 items on your daily to-do list, you’re doing it wrong, too. I would create lists of completely unattainable proportions or so vague that the item was never really complete. Thus, I felt like I never accomplished anything.
Now, I write many of my blogs on the fly. I can write 1,000 words in an hour or less when I’m inspired, triggered, or otherwise emotionally motivated.
But for larger projects, client work, or research projects, finishing a little each day trains your brain to trust the process—and that’s where true self-discipline is built.
Break It Down
Break your lists into small, achievable chunks. Take your big tasks and break them down into little tasks. Not sure how to break a project down into daily chunks? Ask ChatGPT to help. (Yes, I’m a writer—and yes, I use ChatGPT like an office assistant and mentor.)
By breaking down a writing assignment into daily, bite-sized tasks, you can avoid overwhelm, build momentum, and actually enjoy the process. Here’s an example of how a 1,200 to 1,500-word article can be completed in five focused days without overwhelm, anxiety, or procrastination:
- Day 1: Brainstorm, define your audience, and create an outline
- Day 2: Draft your introduction and first section
- Day 3: Write the body sections and develop your core examples
- Day 4: Wrap it up with a conclusion and complete a rough edit
- Day 5: Final polish, format for submission, and hit publish
Even the biggest, most insurmountable projects can be accomplished by simply hacking away at them, chunk by chunk. As long as you’re making progress, you’re moving forward, and that’s all that matters.
A Few Listing Hacks to Build Self-Discipline
For me, listing isn’t just about getting shit done. It’s the mental preparation for planning the day, maximizing my time, and allowing myself a little guilt-free downtime. You see, as a child in my house, I was taught that rest and recreation are rewards for a hard day’s work.
So, my little list of crossed-off items was my ticket to freedom. Whether freedom meant a day at the pool or a night at the local skating rink, those scribbles equaled cash, even to a 10-year-old.
Forty years of listing later, there are a few things I’ve learned to make my lists more effective.
Categorize Your List by Energy Level
Let’s get human for a second, shall we? Some days, you wake up ready to conquer the world. Other days, you’re lucky to conquer your inbox. One trick I’ve learned to stay disciplined without burning out is to group my to-do items by the amount of energy or brainpower they require.
Here’s how it works:
- High Energy Tasks – writing, graphic design, recording, editing (mornings)
- Medium & Low Energy Tasks – admin work, social media, emails, website maintenance (evenings)
Labeling your list this way lets you match your energy to the task instead of fighting your body or brain. It’s still self-discipline, but it’s self-discipline with compassion—because burnout doesn’t serve your long game. Plus, notice how I’ve focused my tasks for morning or evening? That’s so I can prioritize “play time,” such as exploring, hiking, or doing whatever during the day.
Keep the List Visible
I’m a tech geek, but as much as I’ve tried, digital to-do lists and apps simply don’t work for me. Don’t get me wrong, they’re fantastic, and I’ve tried dozens of them. The functionality in many of these apps is phenomenal.
But here’s my mental dysfunction – if it’s out of sight, it’s out of mind. If I have to pull up an app, a tab, or a separate window to look at my to-do list, it will get overlooked.
I require paper, where my to-do list is always physically visible. A good ol’ whiteboard works well, too – if you have the room to hang one. Obviously, RV living makes whiteboarding a little more challenging.
Use Your List to Make Tomorrow’s List
Now, here’s the kicker. ALWAYS make item #10 on your daily to-do list, “Create tomorrow’s to-do list.” By the time you make it to the last item on your list, you’ve prepared tomorrow’s list and you’re already ahead of the game.
No matter how you slice it, accomplishing 10 productive tasks toward your goal is called “progress.”
This item is critical, because one – it triggers that moment in your brain when you can lean back in your chair, and mentally disconnect – “Ahhhh, my list is done.” Plus, it also mentally prepares you for tomorrow.
Self-Discipline Is Freedom in Disguise
At first glance, self-discipline feels like a buzzkill. It sounds like structure, rigidity, and saying “no” when you’d rather say, “Hell yes.” But once you reframe it—as I have over years of freelancing, mountain living, and now RV life—you realize that discipline isn’t the opposite of freedom.
It’s the path to it.
When you master your time, your energy, and your workflow, you get to earn those mid-day hikes, those long lunches, those spontaneous adventures. And even better? You enjoy them without that nagging feeling that you “should be working.”
Whether you’re freelancing from a campground in the desert or the corner booth of a café with a view, your best work will come from a place of alignment—where your habits support your goals, and your lists are tickets to the life you want to live.
So don’t strive for perfection. Strive for progress. One focused day, one finished task, one guilt-free break at a time.
