The Flipside of Flexibility

Too much freedom can backfire

Today’s edition of Wishful Working is a 3 minute read.

In October 2021, my life turned upside down. 

I quit my job, sold my car, stored all of my worldly possessions in my parents’ basement, moved out of my rental house, got married, and moved to my new husband’s hometown in rural Saskatchewan — all within a matter of weeks.

In retrospect, I’m not sure I recommend changing your employment status, marital status, and immigration status all at the exact same time. 😅 It was a whirlwind. And stressful.

On the other hand, it also ended up being an opportunity to take some time off. I needed to recover from burnout, and I needed time to settle into a new place, a new home, and a new lifestyle. I rested, did a million house projects, and planned my next steps.

In March 2022, I officially launched my freelance business.

And I had no idea what I was doing 😂

I had some early wins, but I also had some *ahem* learning experiences:

  • Because I didn’t know where else to look for freelance projects, I spent hours wading through spammy listings on Upwork.

  • I took on a few projects I knew weren’t a good fit because I felt I needed them.

  • I did entire projects without a contract. 😬

And one of my biggest learning experiences was in how I organize my workday and manage my workload. 

Here are a few things I learned the hard way:

Structure was never the enemy

At previous jobs, I grew to resent the strict structure of my day. I didn’t like the rigid 9-to-5 schedule, the daily stand-up meetings, or the lack of control over my tasks.

When I started freelancing, I threw it all out in pursuit of full independence, creativity, and flexibility. I embraced a fluid schedule where I worked based on my energy levels and inspiration.

It didn’t take long to realize that structure was never the issue — it was expectations put on me by others and arbitrary “standard” processes that really stifled my autonomy. I slowly added bits of structure and routine into my freelance work, and I was much more relaxed and happier.

Having control over my own destiny is everything.

It’s okay to ignore advice

Especially at the start, the different freelance advice I encountered was overwhelming. Tips from different freelancers would contradict each other, and lots of it contradicted what I felt was best for me. But, desperate to do things the “right” way, I felt torn.

Spoiler alert: For most things, there is no “right” way.

There is no one-size-fits-all approach to freelancing. You can test things out to see what works for you, and you can also outright reject advice that may be “good” for some people but not for you.

Deadlines can be deceptive

When I first started freelancing, my main project management technique was keeping track of deadlines. This worked — sort of. I turned things in on time, but I was always stressed. I was planning when to finish projects, but not when to actually do the work. 

I now use a combination of time-blocking and time-tracking to organize my workload and figure out when I’m going to work on which project.

(Coincidentally, time-tracking and time-blocking are two often-recommended approaches that work for some people and not for others. I share this to be informative, not prescriptive — find what works for you!)

Ultimately, I realized that in rejecting the dysfunctional aspects of a traditional job, I had thrown the proverbial baby out with the bathwater. 

While it is incredibly important to dismantle and reject the norms of traditional employment when you become a freelancer, it’s equally important to then rebuild a new system using the elements of structure, routine, and productivity that work for you.

Next week, I’ll share more about the systems I use to manage my freelance business, along with some approaches I tried and rejected. Woo!

See you then,

Kara