freelancing

a streamlining check-in.

Earlier this summer, I committed to streamlining.

To give you some context, here’s a little #flashbackfriday action from my May/June monthly goals post

… she gave me some great advice. “You can’t keep adding and adding and adding,” she said. “At a certain point, you need to subtract a few things. It sounds like you’re scared to do that.” And she’s right. I am! It took me so long to establish myself as a writer and to get my income up to a place where it rivals what I was making in my corporate job that I can’t help but feel some innate sense of failure at the mere thought of unloading any one of my gigs… even if doing so will make room for bigger and better opportunities. These are some seriously tough calls, friends.

In the weeks and months since I shared that, I’ve been making those tough calls. I stopped writing on a weekly basis for one outlet, in particular — an outlet that had given me great, consistent work and had afforded me the opportunity to rack up lots of fun bylines, but that demanded a more structured system based on hours instead of stories. The system had put on a strain on my freelancing flow from the beginning, but I went with it, anyway… until I realized that I was no longer feeling challenged by the work. By the time I made that realization, I had brought on some other clients that helped beef up my regular monthly income and had made plans for the podcast — a project l knew would only take up more of my time going forward. I had also more or less stopped working on my book entirely, and had barely been pitching to new editors and outlets because the schedule was so restrictive and I had to spend so much time scrambling to meet my existing commitments.

When I read all of this back, I realize just how right I was in making the decision to stop writing regularly for this outlet when I did (even though the team was awesome and I miss them!).

Still, I’m not a quitter, and it was hard for me not to think of streamlining as simply giving up.

It’s been a few weeks since I made this major change to my schedule, and I thought I’d share a bit more about how the transition has been going. If you’re like me and have trouble saying “no” to things or offloading commitments, here’s what you can expect…

First, I felt overwhelmed by, well, change. Change isn’t always the easiest thing for me to deal with, and any time I have to make a major adjustment to my schedule, it shakes me up a little. I launched The SSR Podcast the week after I quit working for the outlet I mentioned above, so all at once, I had a lot of newly free hours on my hands and was also trying to figure out how the heck to simultaneously produce and promote a show of my own! After spending so many months as a new freelancer trying to fill those hours productively, it was unsettling to feel like I was back at square one again… even though I knew wasn’t really.

Still, I knew it had been the right decision. If it hadn’t been for the looming podcast launch, I probably wouldn’t have chosen to streamline, even though I knew I would eventually need to make some major changes to my workload so I could free up time to challenge myself with new writing opportunities. Since I had a new project to throw myself into at that moment, I didn’t have to stress as much about whether or not it was the “right time” for me to pivot. The podcast was taking up so much of my time (especially in those early weeks, when I had almost no idea what I was doing!), that I couldn’t even imagine juggling it with all the work I’d been doing for the outlet I’d quit. It was satisfying to realize that trusting my instincts had been the right call.

I realized that I could be proud of myself… for a few reasons. First of all, when I stepped back from the self-imposed guilt I was feeling about “giving up” any part of my writing workload, I saw that it was actually pretty cool that I’d reached a point in my freelancing career where I had the ability — financially, primarily — to make some decisions. When I first started in this world, I was hungry for work and didn’t have the luxury to discriminate or turn down opportunities. I hope that I maintain some of that hunger always (I definitely still feel it!), but when I figured out that the choice to streamline was something I’d earned, I allowed myself a quick pat on the back. I was also proud that I’d finally said “no” to something, because it’s not something I do often in my work!

I worked my butt off. I had no problem filling in those extra hours. For a few weeks in the middle of this summer, I was working 12- and 13-hour days every day. At that point, it was genuinely unclear how I’d had anything else on my plate previously.

Now, I’m giving myself some space to figure out what happens next. I’m now a month beyond the launch of the podcast, and the tasks that were taking me so long to complete early on are starting to become more routine. I’ve figured out a workflow and rhythm for the SSR-related work, as well as how to slot it in around my freelancing jobs. Now, I’m seeing some of that time free up again, and I’m trying to be patient with myself as I figure out how to spend it. I’m already back in a better pattern of working on my book and pitching new projects, so what happens next? Do I focus on up-leveling the podcast? Do I put my head down and try to churn out the first draft of my novel (finally)? Do I get even more relentless about seeking new writing opportunities? Honestly, I’m not quite sure yet how it’s all going to work, and while I’ve had moments over the last week or so when that’s felt weird, I’m trying to remind myself that it doesn’t need to get figured out all at once. I’m still busy, I’m still earning a steady income, and it’s summer! Which means most other people out there aren’t making big decisions, either : )

I’m heading to the beach with family for a few days this weekend, but I’ll be right back here Monday to announce the winner of the July giveaway! The prize is a $25 gift card to BaubleBar! All you have to do to enter to win is comment on my last post here. There are just a few days left, so don’t miss out.

Do you have anything fun planned for the weekend? Tell me all about it in the comments below!

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thoughts on how to support your freelancing + side hustlin’ + WFH friends.

I honestly don’t know how I would have made it through these first (almost) two years of freelancing and of working from home and for myself if I didn’t have the support of some pretty kick-butt people. I was reminded of how lucky I am to have such amazing humans in my corner more recently when I launched The SSR Podcast. This whole “nontraditional career” thing is no joke, and as much as I create structure and routine for myself, it can sometimes be the people in my life who provide me with what I really need to move forward with my writing — and now with the podcast, too.

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I’ve been thinking about writing a post like this for a while, but I found myself hesitating about it a few times over the last few months. I never wanted anyone to feel, when reading it, that they had done something “wrong” in approaching a friend who, like me, is pursuing a freelance or self-employed lifestyle or who is trying to launch a business or side hustle. The truth is that any effort you make to support a friend who’s doing this is meaningful, and I know I speak for all of us when I say THANK YOU THANK YOU THANK YOU for the love!

In the past two years, I’ve been on the receiving end of all kinds of efforts to support and understand what I do, and since freelancing and side hustles seem to be on the rise (at least, according to my editors!), I thought it might be interesting to organize some of my thoughts about the best ways to be there for people in those situations. I do think that there are a lot of misunderstandings out there about what it’s actually like to be your own boss or to work from home, and it’s easy for those of us who do it to be oversensitive about them. Hopefully, these tips will help you cut through those misunderstandings so you can (respectfully!) be the cheerleader I know you want to be : )

1. Ask questions. When I left my corporate job to pursue writing full-time in 2016, I’m sure that plenty of my friends felt confused about what I was doing. And I totally understood that! There were moments when everyone’s confusion made me question what I was doing, but what helped were the many great conversations that came from it. When people asked genuine, earnest questions, it gave me the opportunity to get more and more clear about where I was going. More importantly, it made me feel like they respected me enough to talk to me about my “work stuff,” even if they didn’t quite understand it right away. And that’s still true! Ask your freelance, WFH, and side hustle friends respectful questions about the work they do, just as you would anyone else. You’ll learn more about their world and you’ll boost their confidence by giving them a chance to demonstrate some of their expertise.

2. Minimize assumptions. Yes, working from home or running your own business can afford you flexibility when it comes to when and where you work. But that doesn’t mean that we freelancers or WFH-ers don’t have routines that are necessary in order for us to be productive! When people equate working from home or being your own boss to habitually sleeping in, taking long weekends, and blowing off work commitments in favor of last-minute fun, it can strike a nerve! While all of those things can happen, they’re the exception and not the rule for most of us.

3. Celebrate milestones. If one of your friends who worked in a more traditional career got a new job offer or earned a promotion, you’d probably congratulate them, right? You might buy them a drink or call them to hear more about the good news. Your friends who have side hustles or work in less traditional settings don’t have those clear milestones, and they probably struggle with that themselves! We’re taught to pursue logical checkpoints, to achieve things in a linear way — and as rewarding as it can be to be your own boss, that lack of a clear path can be a bit of a mind game, too. Look for opportunities to celebrate major professional moments for your freelancin’ and side hustlin’ pals, whether it be when they bring on a new client, launch a new project, or earn enough money to upgrade their workspace.

4. Stay engaged. It’s 2018, and if your friend has their own business, side hustle, or passion project, I’m willing to bet that there’s at least one way that you can engage with it online or via social media. Liking, commenting, following, or subscribing might seem like a small gesture to you, but that kind of engagement is quite literally the fuel that keeps these projects going. Take every opportunity to participate in these ways, and to encourage other people in your circle to do the same.

5. Play the role of a boss or colleague (when appropriate!). Whenever I’m feeling down on myself because a new project isn’t growing quite as quickly as I want it or or because I’m struggling to make connections with the editors I want to work with, one of my best friends reminds me that I’m in unchartered territory and that I’ve already made strides down an untraditional path. This advice is a great motivator because it helps me remember that I’ve already proven myself capable! After that, she helps me talk through small goals that will allow me to make progress. In the absence of a boss to have these conversations with, I do need my loved ones that much more. You know your friend well — what kinds of conversations do you think they might be missing from an office environment, and what kinds of conversations will help them do more and do better with their work? Consider how you can be the one to facilitate those conversations, then make sure they know you’re available to have them if — and only if! — you need them.

How do you support friends and loved ones who work in untraditional ways? If you’re a freelancer or have a side hustle yourself, what kinds of support do you look for? I’d love to hear your thoughts in the comments below. 

 

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