Give Me Liberty or Give Me Some Liberty But Maybe Not Too Much!

I vacate my full-time job to freelance. I travel, work in coffee shops, wake up whenever I want. The freedom is a dream for about seven months. That’s when baristas start learning my name. With every new Starbucks I enter, I can feel the tile beneath my feet unearth. My work is getting worse too.

So I reverse course. I take a new full-time gig across the city. To get there, I must ride the train. Every day, I bike to the train station. My bike is a seen-too-much Schwinn whose tires must be reinflated weekly. I wear a helmet but because I get helmet hair, I bring hair product in my backpack to put on in the office bathroom. I must leave the house by 8:08AM in order to get to my 9AM meeting, which is always so redundant it nearly puts me asleep. The whole routine is long, specific, and rigid.

After only three months, I’m struck by feelings of sameness. I feel burdened by the structure I actively created for myself.

Who the hell am I, and what the hell do I want?!

Creatives are lucky. Our industry allows wavering between the freedom of freelancing and the satisfaction of a salary. And this isn’t even about money – many creatives will say they make more freelancing. But decisions don’t come without fatigue. If you’re struggling with vacillation in your career right now, here are some guiding questions that might be helpful in determining your (current) relationship with structure:

1. Think of your favorite work activity this week. Was it part of your normal routine or out of the ordinary?

a. Normal routine. I do this thing every week.
You might prefer structure, at least right now. Keep infusing your work with fresh creativity, but don’t move to Europe quite yet.

b. Out of the ordinary. Nothing like that had happened before.
You might want less structure. Find ways to change your daily routine to allow for more spontaneity, or make a big change.

2. Think of your meetings with your managers or clients. Are they jam-packed or stunted?

a. Jam-packed.
Your structure might be providing a lot of momentum for you right now. Consider staying in your structure, and finding ways to relieve stress instead.

b. Stilted
Your structure might be inhibiting your creativity. Try signing on for projects that are unlike any you’ve done recently.

3. Are you meeting good people?

a. Yes!
Whatever structure you’ve established is probably working right now. Use your relationships to tweak other elements of work that are annoying you.

b. Not really.
You might need to change your structure. If you’re locked in with a team that bores you, consider creating a self-led project that can expose you to others. If you’re freelancing and feeling lost at sea, consider setting more regular appointments with colleagues.

4. Think about your social life, your family life, and your community. Are things chaotic or fine?

a. Chaotic.
Structure might be advantageous right now. Creating a routine will help minimize the space work is taking up in your life, allowing you to nurture the other elements of your lifestyle.

b. Fine!
It might be a good time to shake things up. Venturing out from a structured environment, or even changing your day-to-day schedule will have its impact on other parts of your life. This might be a good time to risk it!

5. Think about your best creative work in the last year. Was the assignment highly structured or open-ended? [Try to avoid thinking about school, as it is inherently structured]

a. Structure has somehow sparked my best creativity.
It’s hard for a creative to admit, but you might like to keep things consistent. You know what they say, parameters might be the best thing for your creativity.

b. Open-ended prompts bring out my brilliance!
Don’t let yourself fall into too many routines! Even if you love your full-time job right now, be on the hunt for ways to change the rhythm of your workdays, and the types of work you produce. You were probably hired to do just that.

One more thing I’ve learned — there’s structure to be found in freelancing, and there’s freedom to be found in full-time employment. If you’re feeling the itch to shift your career, it might be good to take on small, iterative fixes before making big changes. Think about your commute, think about the times of day you write, think about who you’ve been spending most of your time with in the office.

Your career is yours to box and unbox at your leisure. If you spend some time defining your ideal working parameters, you might face fewer existential crises.

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