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This past week I’ve been researching freelancing.

As of four days ago, I am unemployed, though I’ve known that end date for a month now. After spending many of those days crawling job crawlers and reaching out to a few people in my network, I became disheartened: I’ve submitted at least 40 applications by this point, and have only gotten one “let’s continue talking” response. And with this disheartening came a new stress: a vague, urgent fear.

But…fear of what? This unnamed fear catalyzed a reaction that I’m only accustomed to having at work, which I call solution scoping. I began to analytically pick apart my situation, examining its shape and components and teasing out a ‘problem statement’ whose solution I could begin to design. The problem I arrived at, to my mild surprise, was not, I’ve lost my job; it was, I’ve lost my source of income. And as soon as I shifted my perspective on my situation from needing a job replacement to needing enough money to sustain my partner and me, the fear lessened and I grew calmer. That problem feels more open-ended and thus gives me a certain amount of confidence that I can design a good-enough solution to it.

Freelancing is not something I’ve ever seriously investigated, but it came to mind immediately when I began ideating on possible approaches to regaining my lost income stream. And thus began my research.

do I need to start a business?

The question I began with was whether or not I needed a business in order to legally perform contract work. The answer is no, but after reading many articles from authorities I found at least shallowly trustworthy, I decided that founding a business would benefit me more than not. One of the less tangible benefits is peace of mind: I like to compartmentlize, and being able to wrap my “business things” up in a nice box with clean edges and a clear interface provides me with great comfort.

Further research lead me to take two actions: 1) found an LLC, and 2) use doola to do it. I chose to form an LLC because it offers me the legal weight and protections of a business without the red tape of a corporation, but without precluding me from morphing into a corporation later on if it makes sense. The choice of service for forming my company was less cut-and-dry: there were several contenders I ended up choosing from, and I boiled them down to doola and ZenBusiness. It was a tough choice; in the end I went with doola because part of their base offering includes a business mailing address and virtual mailbox, which is important to me since my location changes frequently.

I am now waiting for the state of Hawai’i to process my LLC formation paperwork; doola tells me this could take up to two weeks and is the only part of the process they can’t influence.

what is ‘freelancing’?

Amusingly, this was not my first question. I began with a confident, if vague, understanding of what ‘freelancing’ is, and so I didn’t immediately seek to define it in more concrete terms.

But when I did, the first thing I Google’d was its etymology. Classic me. And I had one of those moments in which I realized the common pronunciation of a word impedes me from intuiting its compound nature: freelance comes, literally, from free + lance and was originally used to describe mercenaries back in the day when people walked around with swords and (you guessed it) lances. They weren’t ‘free’ as in ‘beer’, they were ‘free’ as in ‘available’. Mystery solved.

I moved on to watching YouTube videos about real humans experiencing the life of a freelancer: I wanted to know if it was just as chaotic and unstable as I’ve always been afraid it would be.

And it seems like the answer to that is ‘yes.’ However, I take it with a pinch of salt: the people sharing their stories were all self-identified ‘hustlers’, which seems to mean they are not merely interested in maintaining a diverse income stream, but are also passionate about maximizing the income they generate, and thus are putting forth incredible amounts of effort (aka hustling). I am skeptical of how much that lifestyle will apply to me. Do I need to Always Be Hustling™️ just to make more than I spend each month? We’ll see. If it is, then I definitely don’t want to be a full-time freelancer: I don’t like to hustle.

how do I find work?

Once I’ve established my LLC and am ready to work, how do I actually do the thing? This is the biggest fuzzy point and thus point of stress for me about the whole freelancing idea. Will it be incredibly challenging to find work for myself when I need it?

I’m still focused on this question, but a friend of mine tipped me off about a platform called A.Team as a potential work source. I applied to join and was just accepted into their midst today, and from what I’ve learned about it, I’m quite excited. Essentially, A.Team has created a network of top-tier freelancers and acts as a talent sourcer for companies that have projects requiring too much work for just one individual. A.Team posts these ‘missions’ on their internal job board, and then puts together a bespoke team based the platform members that request to work on it; within a week or so, a contract is formed, and the teamwork begins.

This is a paradigm shift in the way freelancing works, and seems like it functions almost the way guilds work in the fantasy worlds I read about. I do not like working in isolation, and I didn’t realize how much that factored into my hesitation to freelance until I came across A.Team; I felt a huge surge of relief and excitement that I didn’t necessarily have to work alone. So we’ll see how this goes.

~ Daniel.
2 months ago