Jan 3, 2023

10 Planning Tips for Freelancers

Prepare to be Flexible

As a freelancer, every day is a fresh start. I feel the January-1st newness with different clients & projects at many points throughout the year. Time is a social construct...and yet as the calendar resets, months end & begin, or seasons roll into each other, I can't resist the urge to clean, organize, and reset. Setting concrete goals can organize an ever changing work lifestyle or overwhelm a perfectionist heart. This is how I've approached regimenting my ever changing calendar...

- Gill

1. Break everything into small steps

Looking at a project as a huge chunk, start to finish, feels impossible. So does looking at the whole year ahead. My road to success (whatever success means for you or I) has consisted of thousands of small steps, which is not far off from the hours, minutes and seconds that make up a year. When I start to spiral into a world of overwhelm, the only thing that helps is looking at my week in small chunks. These small chunks can be days within the week, meetings throughout a day, or a to-do list of small steps in a project.

"The reasons why we don't reach out goals is because we set them too far ahead of time." - Louisa Nicola, What's the Juice

2. Be flexible with big goals & diligent with small goals

I've done the giant gestures - two long weeks in Europe, cutting 6 inches off my hair, promising myself that I'd walk every day for an entire year...and all that got me was disappointed in myself when I felt unchanged or failed in my "goals". The things that have had huge impact on me were setting small goals that I can realistically commit to. Freelancers rarely know what they will be doing 6 weeks from now, let alone 6 months. I let my yearly plan be a rough sketch, centered around emotions. I want to be less stressed, I want to feel more fulfilled. The way to get there is by making the mundane things you do every day lead you to that goal. The big projects, ideas, or goals are a sum of all the small pieces. Conquering those will get you there in a sustainable & manageable fashion.

3. Constantly evaluate what is serving you & what doesn't

I am addicted to quitting things, but at the core of that is me exploring my relationship with everything in my life. Exercise, sleep, caffeine, rest, joy, pain, screen time, kale...the list goes on. I often find that by removing something from my life, I better understand what it was doing for me, whether that be negative or positive. Self-evaluation is a process, and sometimes in the act of unraveling a goal from the macro to micro, you may learn that getting out of bed at 5:30 gets you closer to your goal of journaling every morning or meal prepping before work. That unraveling may also show you that getting up at 5:30 makes you too tired to actually feel good throughout the day.

4. Don't be afraid to abandon goals that don't feel good anymore

We change, and as we do, so do our goals. It has been really hard for me to be ok with shifting priorities, especially for us perfectionist over-workers who self-identify with our goals, titles, and career aspirations. And yet the most compassionate and honest thing we can do is let our goals shift. It is unnatural to let previous versions of ourself decide our destiny. Letting go of an unachieved goal is not a failure, it is a shift in where you are putting your personal & professional energy.

"There is no such thing as wasted time...just things we needed to learn." - Just Break Up Podcast

5. Digitize your Systems

I had a paper planner my entire life. I swore I could never switch over to a digital system, and yet...it is the easiest way to keep up with your calendar & track your to-dos. I use TickTick & Apple Calendar to stay organized on the go. TickTick has to-dos that you can view as a list or on a calendar + a built in POMO timer to help with day-to-day focus & time management. Apple Calendar helps keep my schedule at my fingertips. If anyone asks me about my availability, I can back to them promptly. This makes it easy to throw meetings & dates on my calendar immediately so I never double book myself.

6. Make sure you set time aside each week or month to schedule

Scheduling takes time, but will ultimately save you time. I like to take a day every month or two to plan out what freelance projects I have going on with due dates + itemized lists of every single thing I have to do to complete that task. I do this while looking at my long term calendar, so I can adjust due dates based on book-out dates or other long projects that require full time attention. The hardest part about scheduling is sticking to your personal deadlines, but that does become easier with time. Making to-do lists more specific can also help by giving you bite-sized tasks that can be easily completed. It also is essential to...

7. Get ahead

The easiest way to remove pressure from yourself is getting ahead with projects. There are many elements of my career that are time sensitive or require me to be present to complete the task (short-form commercial productions, full studio days, etc) but a lot of my work can be planned & scheduled ahead of time. When I have down time, I try to get as far ahead as possible so that when I do have unexpected work arise or long weeks that I'm booked out, I don't fall behind or have to squeeze in freelance projects between full day bookings. This ultimately helps my scheduling because I have the flexibility to say hell yeah to last minute work since all of my routine projects are taken care of.

"We thrive when we have a positive goal to move toward, not just a negative state we’re trying to move away from." - Emily Nagoski

8. Remind yourself why you do what you do

When goals & plans feel hard, it could be because we don't know why we're doing what we do. This can be extremely true for self employed folks and creatives because we don't have a team of people setting our schedule, telling us metrics for how we should be achieving, or giving us a roadmap for the next few months. It is difficult to monetize your passion because that makes it work. There are days that you don't want to do the thing that you once loved doing, but tracing back your "why" really helps. You should also...

9. Put creativity & fun in your calendar

I feel extremely burnt out when I am not doing anything for me. Whether that be taking a day to work on my music, open up a story I've neglected, or exploring a new shop in my neighborhood, these things all refresh me. The one thing I struggle with is being sure it happens. As a freelancer, it is so easy to fill up your calendar with exciting projects and feel pressure to say no - especially when you are genuinely interested in all the work requests you are getting. Thats why scheduling time to unwind or be creative the same way you'd schedule work meetings can really help ensure you put the proper amount of time towards yourself. And...

10. Tap out before you burn out

It is easy to use caffeine to push past the exhaustion or use social media to compare your journey to others, but that will not prevent burn out. Listening to your body is the only way to know when you need a break. I have pushed myself past my limit many times & whenever that happens, it takes so long to recover. My body is exhausted and my nervous system feels so dysregulated that it takes a lot of work to get myself back to equilibrium. Avoiding this can be as simple as taking a day off when you can, sleeping in when you don't have an early morning meeting, and sticking to your scheduled me-time. I often find that burnout comes when I am consuming instead of creating or putting effort into everyone else's projects and neglecting my own. Taking the time when you need it will always help you from getting to a low point, but when it does happen, be kind to yourself. You can do it!


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Gill with the G

Gillian Pelkonen is a musician & audio engineer based in New York. She makes her own music and is always looking to collaborate. As an Audio Engineer, she helps people elevate their sound, and specializes in techniques that enhance natural vocal texture & dynamics (aka the best parts of your unique voice).