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When does the side hustle become the full hustle?

When does the side hustle become the full hustle?

A couple of weeks ago, I wrote an article right here on the Polywork blog about how I built a six-figure side income – with some suggestions on how you might build yours, too. I was flattered at the response from many of you, who felt the tips were helpful or my own experience could be a guidepost towards becoming the polymath that I think we all truly want to be.

A question arose from many friends after I wrote the article that went something like this: if you’re making six figures at your side income, why not just make that the whole thing?

It’s a fair question, and I’m not money hungry by nature so the answer isn’t “just make as much money as I possibly can.” If that were the case, I would have gone into finance after college. I would break it down into three categories: resiliency, growing my network (and not in the shmoozey way), and getting better.

1. Resiliency

I have previously written about getting laid off in the first month of the pandemic, and I don’t want to understate how traumatic that was. I had never been let go before and I was living in an expensive studio apartment in one of the most expensive cities in America with little to do but think about how I was ruined. If I had not given 80 hours a week to that job and instead given it the appropriate 40, and used maybe 10 additional hours to freelance on the side, I would not have felt as destitute. As corny as it may sound, I developed a mantra at that time that was simply this: I will never hustle towards someone else’s dreams.

I developed a mantra at that time that was simply this: I will never hustle towards someone else’s dreams.

I was one of the lucky ones that found employment less than two months later, but I found fractional employment even sooner than that. Within three weeks, I locked in my first freelance contract. And then a few weeks later, I locked in another. When I finally got an offer for a full-time job, I wasn’t even sure I wanted to take it because the freelance side was growing quickly and organically, but ultimately decided that the opportunity was so good that I could figure out a way to do both. After all, I was used to working the 80 and that’s when there were actual things to do outside of my apartment, not in the throes of a global pandemic.

If I had gotten let go from that second job, I would have been fine right out the gate. Sure, there’s the emotional toll of a layoff, but the financial anxiety wouldn’t have been there because I would have had enough money saved from my year of freelancing, and ongoing from that side income. The practicalities of that are one thing, but the cognitive burden is another.

The resiliency that this side income has given me has allowed me to remove any scarcity mindset I have around my work. I’m not clinging to a job anymore, and I can be much more objective about when I’m doing great and when I need to improve.

The resiliency that this side income has given me has allowed me to remove any scarcity mindset I have around my work. I’m not clinging to a job anymore, and I can be much more objective about when I’m doing great and when I need to improve. Every last piece of my job doesn’t feel personal, because it isn’t my only thing. Rather, picking up work and work-based self-esteem (we’ll get to that later) has offered me independence and the opportunity to truly know that I can make it work – come hell, high water, or a global pandemic.

2. Growing my network

I always bristle at the term “network” because I’m not confident there’s a way to say it without sounding a little smarmy. When I say “network” I don’t mean sliding into someone’s LinkedIn DMs that you are four connections away from and introducing yourself with a sales pitch. I mean doing great work for people, and in turn those people turn around and introduce you to other people who need your great work.

The network effect of my side income experience has been huge. Even before I built this out to a six-figure business, it had me in rooms and on calls with Emmy-winning directors and new entrepreneurs, enthusiastic mid-career pivoters, and eccentric creatives. I’ve coveted every one of those experiences because they have come organically from my network, and because I generally operate around the idea that good people beget good people. Be good to work with, work with others who are good to work with, and then they will put you in circles with other good people who can grow your work or simply just be a fun time to work with.

Here’s a quick story about the advantages of building (and engaging with) your network:

As an aside, I have a separate side hustle in that I am an aspiring screenwriter. Many years ago, I was working in PR but on nights and weekends, I would write treatments for an Executive Producer and her directors as they were bidding jobs. Within a few months of that year (2013) I won a short film contest and we premiered a branded content short around the world, and off the back of that, I wrote a movie with a friend of mine.

I knew this EP fairly well by this time, and asked her if any directors in her roster would be interested in reading. She sent it to two, and one of those took our film into development. This had absolutely nothing to do with my day job in PR, but was just a byproduct of my hustle, my work being not terrible, and this EP following the “good people” model outlined above. There’s more to that story, but that’s for over a drink!

The point is you never know where building out your network can help you – whether it’s just in a solid gig right now or living out your dream job in the long run. I’m the kind of person who gets energized by working with new people (particularly creatives), because it unlocks ideas and new perspectives and stories. If that’s not you, maybe just having one income or a steady freelance retainer with one client is a better fit. But I’d encourage you to stay curious to new people and opportunities as you think about growing your career in a more multi-hyphenate way.

3. Getting better

The counterintuitive part of growing a side income and diverting attention away from my main job is that it has actually made me better at my full-time gig. No, I’m not giving my main job the hours that I could if I didn’t have projects on the side, but more hours doesn’t yield better work. In fact, I’d argue that it doesn’t. Parkinson’s Law is worth citing here, which suggests that work will fill all the time you give it – whether it’s four hours or forty.

Every freelance opportunity offers new context and content to delve into, and different ways to use my superpowers. It also puts me in touch with new experts who can share their insights that I otherwise would never have known. For instance:

  • My SEO acumen has gotten leaps and bounds better by working with a freelance client where SEO wasn’t in my purview, but I needed to consult with their in-house SEO expert in order to successfully complete my work.

  • So much of how we work at work is done through osmosis, and remote work has made that a little more difficult (I still fully endorse remote work and would never go back to an office, but that’s another article for another day!). By taking on these myriad jobs, I can create more opportunities for that osmosis to happen from a variety of places.

The other ways I’m getting better have emerged through the softer skills:

  • I used to be terrible with time management, but having a few side gigs as well as a full-time job has forced me to become amazing at balancing my time. I’ve also improved my communication skills because it is so important to be clear with your clients about if and when you can meet their expectations, and when you need to say no or deprioritize certain work.

  • And to the earlier point of building resiliency, my freelance work has given me space to build confidence in myself as a worker. I have clients refer me to other clients and share praise with me (when it’s warranted). Of course we can get that from our jobs, but that’s one stream of feedback. It only follows suit that when you hear nice things from multiple places, it builds up your confidence that much more.

The “getting better” principle goes in both ways. Having a day job where I have access to tools and a whip-smart team makes me better in my side hustle. I’ve had several jobs in the startup space over the last decade, and every one has taught me something new that I can apply to some of the scrappier places I tend to freelance with. So it’s a win for the client, a win for my work, and a win for me!

Amy Jacobowitz is the Head of Brand & Content at Polywork. She's always open to talking about side projects, freelancing, and more. See what she's up to on her Polywork.