The common wisdom that any decision can be assessed via a simple pro/con list has always appealed to me. For one thing, it involves writing, and heaven knows I’m always up for writing down things pertaining to my tender, delicate feeeeelings. For another, it just seems… tidy. Concrete. No matter the situation, being able to lay out the pros and cons in black and white can help just about anyone gain new perspective, I’ve found.

When people ask me how I like working from home, I’m effusive in my praise for the convenience of it. Truly, I worked in a variety of places for many, many years before turning to freelancing, and I do love having a home office and the freedoms that come along with it. But in thinking over all of the realities, lately, I realize that my standard disclaimer of “it’s not for everyone” is a kind of warning. If I lay it out logically, I’m not sure it makes sense.

Let’s take a look. Surely ye olde pro/con list will help me out, here. Quick and dirty, off the top of my head… no editing.
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My least favorite part of freelancing is that it feels—more than any office job I ever had—like a moving target. I’m not even referring to the goals of the job; there’s always new gigs to pursue, changes in existing work, progress of the field as a whole, etc. I’m referring to the balance between work and home, the school year and the summer, and my family’s changing needs.

Nearly a decade into this, I’m still dealing with the jarring shift in my days every single summer when the school year ends. I feel ridiculous, saying that. It’s not as though I’m unaware that school will let out and my kids will be around. It’s not as though it’s different every year. It’s just that, somehow, it is different every year, as the kids grow and their needs change. What worked the year before is never quite right for the current year, and so every year we have to rethink, readjust, find what works all over again.

When I started homeschooling my youngest, that was a huge shift (and our most difficult one yet). I was sure I couldn’t do it. Surely I would end up short-changing both him and my career. And yet… somehow, we’re making it work. We made changes after the first year. Now we’re making more changes, after the second year. But I feel/felt good about our progress.

I was unprepared for this year’s wrench in the works.
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I used to write here quite a bit about the value of attending conferences—I traveled regularly and spoke at conference events a few times a year, and I think it can be an invaluable way to sort of improve your freelancing career on all fronts. Just by attending an event where you’re likely to meet potential clients and/or have time to brainstorm with colleagues, you’re increasing your own knowledge base and network of potential jobs. And if you speak at one of these events, you’re honing your presentation skills, adding to your resume, and hopefully becoming more comfortable as a leader in your field. And all of this is aside from the fact that a lot of us freelancers lead fairly solitary work existences, and it’s just a good idea to get out and spend some time with other people in a work environment now and then.

In short, there’s tons of good reasons to go to conferences, present at conferences, and just generally place value on getting dressed up every so often to face the world.

I had a good rhythm going there, for a while, and then I had to take some time away from work and tend to other things, and somehow it’s now been years since I went to a conference. It wasn’t entirely intentional. I just got away from it and then it felt hard to get back to planning for and carrying out the travel and such. But I’m finally getting back on that particular horse, next month.
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When my kids were little—when they truly needed near-constant supervision—the only summer option that allowed me to continue working was some sort of care arrangement that covered school hours. They could go to camp, or I could hire a sitter, but there had to be something. As they’ve grown, summer has changed; we’ve gone from constant, full-day care to fewer scheduled activities, and now that they’re both teens, I don’t have to schedule them for anything at all. Let’s face it, they can feed themselves and keep themselves alive without much help. They’ve even reached that magical age where I never hear “I’m booooooooored!”

So the good news is that I can work as much as I need to and I don’t have to worry that my children are going to wander off or set the house on fire or anything. We sat down as a family and discussed the summer, a few months back, and this was the first year where I was really able to say to both kids, “Tell me what you think will work best for you.” My son was really looking forward to doing a whole lot of not much, and maybe spending more time with friends than we generally manage during the school year. My daughter, on the other hand, wanted to take a class and some lessons. They had different desires but we wanted to make it work, and so far it seems like it is.

The interesting thing, for me, is how keeping the kids on a workable schedule is actually helping me make my summer schedule more productive.
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