I start my day early, with a run. (I’m up to four miles now!) Then I proceed through my typical morning routine: meditate, read, journal, and drink the beautiful coffee. This peaceful time is punctuated by kids wandering in, asking questions about breakfast (Yes, you have to eat it, same as every day) and chores (Yes, you have to do them) and school (Yes, you have to go) and friends (No, you can’t invite five friends for a sleepover…ever).

The last step of my morning routine is to to plan my day and do a quick check-in. Around 7:30, I flip to the next blank page in my notebook and list the day’s top three tasks. I review my calendar and weekly to-do list, noting anything that must be done today to stay on schedule. If there are appointments, calls, or scheduled events—or little to-do items like “pick up cat food” or “call Dad”—those go on my list, too.

Then I check email and Slack, respond to anything that takes only a couple of minutes, and note any pertinent updates.

After a quick breakfast with the kids, we all pile in the car. I get dropped off at the library or a shared office space, and Joe takes the kids to school. I plug in my music and get cranking. A few hours later, I emerge into the sunlit tropical world, blink, and decide where I’ll eat. Sometimes I get a to-go lunch and sit on the beach. Sometimes I meet a friend. Sometimes I eat in a cafe and read. If I’m running tight deadlines, I’ll grab some almonds and a sparkling water and get back to work.

Around 3, I start wrapping up. I send off any emails, respond to clients, make notes on anything I need to remember for the next day, update my calendar and to-do list, then pack up my bag. I either walk home (it’s about 3 miles, a great way to shake off computer-brain and reconnect with my body and physical reality) or get picked up by Joe, on his way back from picking up our kids. Or we might meet up at a nearby beach or at the local skatepark.

The rest of the day, and evening, is for family, friends, and fun stuff. Sometimes I work on my own projects during the evening. Some afternoons I have to crank out a few more hours of client work, but that’s rare.

When our kids have field trips, I’ll work an extra-long day or two and take off to go with them. They have amazing field trips.

I tell that story to illustrate the primary “pro” of freelancing, for me: absolute autonomy over the work I choose to do, and over how and when I do that work.

For me, this essential quality of freelancing outweights all the cons. But that’s not going to be true for everyone. Whether the pros of freelancing outweigh the cons is entirely personal. It depends on your highest values.

I value autonomy, a flexible schedule, freedom to pursue my own interests and manage my own projects, location independence, and fresh new challenges. Freelancing works well for me, because it supports what I value.

However, if I valued security, a predictable income, a steady work routine, feedback, collaborative teamwork, paid vacation, and benefits like health insurance and a retirement plan, it would be a different story. I wouldn’t be able to live according to my highest values with freelancing. So freelancing would be much less attractive, more stressful, less satisfying, and ultimately unsustainable for me.

The #1 pro of freelancing, for me, is absolute control over my work, how/when/where I do that work, and, thus, my entire lifestyle.

The #1 con of freelancing, for me, is that there’s no one to pass the buck to. When freelancing sucks (and it can definitely suck), it’s all on me. I’m the one responsible, and I’m the only one who’s going to fix it. Sometimes I don’t know how to fix it, and that’s frustrating. Those are the times when I curse my need for autonomy, but I get over it. Plus, I’m learning to get help when I need it. Freelancing doesn’t mean you have to do everything yourself, or have all the answer. But it does mean that it’s up to you to identify when you need help and then take action so you get that help.

I’d like to contrast my “typical freelance workday,” as described above, with a typical freelance workday from about 10 years ago.

10 years ago, I had an infant, a 2 year old, and a 3 1/2 year old. I worked from home. My neighbors didn’t understand that I actually worked from home, so they frequently showed up for long chats or sent their kids to my house to play. I dealt with this and set boundaries, but it took time and energy to do so and it was stressful. I frequently woke up at 4am to get a few things written before the kids woke up and demanded my attention. I worked during their naptime. I worked while I sat on the bench at the playground. I worked in the McDonald’s playplace. I  scanned job boards while I nursed the baby.  By the time I gave birth to our fourth child, I could afford a babysitter two afternoons a week. I would go out, exhausted, to sit in a cafe and do as much work as possible in that 4-hour window of quiet. Sometimes I would sit in the car and nap for 20 minutes just so I could stay awake and focus long enough to finish something. I struggled to find clients. I struggled to get writing gigs. I struggled to articulate what I had to offer. I doubted my own skills and qualifications. I freaked out a lot. I started a lot of things I couldn’t finish, had impossibly high standards for myself, and felt guilty all the time for the stuff I wasn’t doing.

Freelancing, especially when you’re starting out, is not easy. It doesn’t have to be as difficult as I made it on myself (pro tip: don’t have four kids in five years and try to build a freelancing business at the same time unless you have serious masochistic tendencies which, apparently, I have). But it does require dedication, focus, hard work, and time. It’s easy to become disillusioned if you have expectations of ease. You don’t float in on a freelance cloud of high-paying gigs and eager clients. You have to do the work and do it consistently. It takes time and it can be discouraging when you don’t see progress.

However, if you—like me—value autonomy highly, want control over the kind of work you do and how you do it, and want to create a lifestyle that suits you (rather than settling for the best you can get), freelancing is a possible path and a worthwhile effort.


Photo by Ferenc Horvath on Unsplash

August 21, 2019