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.
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.