Why Freelance: Andrew Karpie’s Freelancing Story

When it comes to why we freelance—in other words, why freelancing has become a more and more popular choice across the country—I cannot answer for everyone. As someone who has worked as a research analyst at Staffing Industry Analysts (“the global advisors on contingent work”), I should know better than to broadly generalize.

The fact is, there are many different reasons why people freelance. Some of these reasons include flexibility; work specialization; finding one’s optimal trade-off between money and other non-pecuniary values; even “sticking it to the man.”

Deciding to go freelance is a very personal decision (one, I believe, that a freelancer makes almost every day). Therefore, I can only really speak about myself and my own journey into freelancing. So here it goes.

Why me?

Some of it is in my DNA.

  • I like consistency, but not bureaucracy. There can be amazing benefits to working as an employee of an organization—but for me, the bureaucratic side of organizations can become a tremendous distraction and even a downer. Being buried in bureaucracy is not for me.
  • I tend to be more project-oriented than job-oriented. I’ve always liked to get absorbed in projects and not get distracted. In a job, there are always many different demands on your time and concentration. Few jobs allow one to choose and sustain focus.

Some of it has to do with practicality.

  • When I was an employee, I could only engage in what was circumscribed by my employer’s business. I found I wanted to do things that were natural extensions of my work, but did not fit the business model of my employer. The answer: become a freelancer (not an employee).
  • My employer was willing to work with me to determine a way for me to transition from employee to freelancer. Many freelancers get started with this practical path, which is often beneficial for both parties.

Lots of freelancers are driven by an entrepreneurial streak—and when they are, I think this is a very positive motive that can lead to truly great things. Though I am fiercely independent, I do not have the DNA of an entrepreneur, and I find that my primary reason for freelancing is simply to be able to work in the way that I work best, in a structure that suits me.

So how’s that working for you?

I often get this question, and I find it difficult to answer in detail. My usual response is “pretty well,” and that does truthfully sum up all of the pluses and minuses, without having to speak to each of the items on either side of the ledger. But this post is an opportunity to go a little bit deeper, so here’s how I do my reckoning of some of the top items.

On the plus side:

  • As an analyst, I am now completely free to roam and graze wherever I please and on the terms I see fit. This is incredibly beneficial if your job is finding out what is going on, and analyzing and synthesizing that information into industry perspectives.
  • I (pretty much) only need to do projects that are related to what I am specializing in, so I don’t get distracted by other areas of work (or by bureaucracy, or its ugly cousin—office politics).
  • I find the flexibility advantageous. My hours are my hours; I can take on a heavy workload or keep it restricted to a lower level when I need to.

On the negative side, there are issues, but they can be mitigated:

  • Uneven cash flow is a perennial issue for freelancers, even if there is plenty of work. Working through a platform with an escrow system can help this a lot. In addition, accepting a client’s offer to be paid by a third party as a W2 worker (including withholding taxes) is nothing to be ashamed of—you are still a freelancer (and payments will be less of an ordeal).
  • If most of your work is done remote/offsite, I find there are number of issues to contend with:
    • What I call “Remotitis.” I mean, I love my dog and his companionship. But remote work can lead to this freelancer malady, which is caused by insufficient human contact and interaction. The cure is easy though: mix up your schedule with outings, outside meetings, trips to the gym (ok, bring your tablet), errands, etc.
    • If you thrive on collaboration, like I do, then remote work can be a bit limiting. Yes, it is free of distractions, but it doesn’t really maximize collaboration and its benefits. I know, though, that collaboration platforms and tools are on the rise, and I suspect that their support of real collaboration will improve over time.

On the whole, I almost always feel like I net positive, though I think no freelancer can expect to have their cake and eat it too. On the freelancer journey, there is no free lunch—you eat what you kill.

At this time in my life, I choose to be a freelancer and not to be an employee, because that seems to allow me to do the work that I want to do. There are other challenges and barriers to getting the work done, but they come from the terrain itself—not from an organization that is mapped to a different purpose and set of objectives.

I always come back to the well-known quote from Andrew Carnegie: “My heart is in the work.” That is why I freelance.

Your turn: Why do you freelance? Share your experience in the comments section below!