On the Topic of Structure and Schedule

When asked, I oftentimes tell people that I fell into this career as a self-employed freelance writer, editor and blogger “accidentally on purpose.” By that, I mean that I never really had any real intention of going into business for myself. After graduating with my bachelor’s degree, I figured I was going to join the traditional workforce like everyone else. And I did… for about four months. I think that’s still longer than however long John was traditionally employed.

While at my first “real job” after university, I applied for a freelance writing gig on Craigslist, almost on a whim. I figured it might be a good opportunity to earn a little money on the side, all while working on my portfolio and expanding my writing experience. Applying for this gig was definitely “on purpose,” but leveraging it as a launching off point for my freelance career was not something I had fully anticipated.

Work When You Want To

Long story short, I’ve been doing this for well over a decade at this point — including my blogging duties here on John Chow dot Com; “If you want something done right, let Michael Kwan do it,” John once proclaimed — and I have no intention of shifting away from this “work from home” lifestyle any time soon. But my attitudes and approaches toward how I go about living my “work from home” lifestyle have shifted over time.

You have to understand that one of the greatest appeals of running an online business and working from home is the time flexibility. I valued that tremendously in the beginning and I continue to value it tremendously today. It meant that, on many days, I wouldn’t even get started until some time after noon. If I wanted to sleep in — I do love my sleep — I could. If I felt like firing up the computer after dinner to bust out some articles, I could usually do that too.

This level of flexibility — I still had some daily duties along the way, so it wasn’t 100 percent flexible — meant that I could take extra long lunches or do my grocery shopping in the middle of a Wednesday afternoon when everyone else was at work. It meant that I could attend trade shows and events, like CES in Las Vegas and Computex in Taipei, so long as I planned it out in advance. In this way, I didn’t really have any sort of set schedule. I worked when I could, so long as the work got done.

Clearing the Mental Space

But, as the years went on, my attitude toward a more predictable schedule started to change. I started to find that because I could work at any time, I’d feel obligated to work all the time. Whenever I had a few spare moments, I felt like I should be doing something productive. If I decided to watch TV or play video games instead, a lingering guilt developed in the back of my head. This has only gotten worse since becoming a dad a few years ago. There’s always more to be done.

I get that a big part of the reason why I decided to get into freelancing in the first place was because it required no set schedule. There’s no set commute to the office. There’s no clocking in at precisely 9 a.m. and clocking out at exactly 5 p.m. But herein lies the paradox. As I have no schedule, I start to crave that structure. And so, particularly now that my daughter is in kindergarten with a traditional Monday to Friday school schedule, I’ve made the conscious decision not to work on Saturday and Sunday. Or at least work as little as possible.

It’s a marked shift and one that flies in the face of what Chelsea Fagan from The Financial Diet said in an interview. While it’s true that we “escape” the 9-to-5, we’ve almost come to embrace the 24/7. At this point in her career, she still values the flexibility greatly and this means that instead of strictly taking Saturday and Sunday off as a rule, or strictly adhering to a daily schedule, she takes her breaks throughout the week and throughout the day. This is by choice, flexing that flexibility for all that it is worth.

Whatever Works for You

When it comes to structure and schedule, you really just have to choose the system that works best for you. Imposing a bit of arbitrary schedule on yourself can provide structure and reduce the guilt associated with not working when you technically can work. By choosing to leaving it more open provides you with the wiggle room you might need to accommodate other life priorities. What’s your choice?