Myths About Freelancing

Making the jump from an in-house role to full-time freelancer can be terrifying. I will not deny you of that truth. But once you get through the initial scare and get rolling, you’ll realize that the security you felt working for a company full-time is actually a bit of an illusion…

Getting let go at a job (a commonplace scenario at quickly growing-and-contracting startups), can happen in the blink of an eye. If you’re freelancing and working for several clients at a time, even if one client drops off, you’ll still have a portfolio of clients to service.

In this sense, isn’t it sort of crazy that full-time roles seem more secure than being self-employed?

Here are a few other myths about freelance life that could be holding you back from taking the plunge into the clear, blue pool of your future career as an independent.

1. Instead of having one boss (when working in-house), you have several bosses.

If you have healthy relationships with your clients, they end up being more like partners than bosses. Yes, you will be held accountable for your work, your clients are continually giving you feedback (that’s a good thing!), and there are expectations associated with what you do; But it’s definitely not like you have a Rolodex of managers who are breathing down your neck. The fact that you were brought in means you are a specialist of some sort and your clients appreciate that you have the guts to do your own thing. (They’re not thinking about ways they can micro-manage you remotely.)

2. You don’t get to see an intimate picture of a company because you’re outsourced.

Again, not the case. As a freelancer, you see the company through a different lens than in-house employees and it’s valuable. As a vendor or freelancer, you intimately understand how outsourced talent is managed (an indicator of company culture internally) and you can provide customer-like insights to your client given your distance from internal affairs.

You can also gather a lot about a place just by being inquisitive. I’m constantly asking clients about how things work internally and they’re often excited to share with someone who can provide an external perspective or share their own experiences from “how things worked” at other companies.

3. You can’t have frank conversations with clients.

When you work on an in-house team, you have such close relationships with so many colleagues that if something’s not right, you talk about it (hopefully). There’s an illusion that if you have an issue with a client, you can’t talk to them about it. They’re your paying client so you don’t want to rock the boat, right? Wrong. It’s all about approach.

If you disagree with a certain strategy and feel meek about speaking up, remember that one of the reasons you’re getting paid is so that you can help define that strategy. Sure, there are a lot of freelance projects landed on sites like Fiverr or Thumbtack that are assignment-based, but most long-term clients want your opinion and welcome alternative perspectives. Respectful communication is key to any healthy relationship (said my wise fiancé).

4. You have to hustle far more than if you work in-house.

This can be true at times, but if you are priced correctly, work diligently during normal office hours, and stay focused on production for clients versus giving into the temptation of working on personal projects during biz time, you can work hours comparable to what you’d work at a 9-to-5 job.

I was moonlighting during my time at my last full-time job. I worked Monday through Friday at the day job, and my weekday nights and Sundays were filled with freelance work until I built up enough clients to leave that full-time role and start my own business. When I started my own business, I got my Sundays back, though I do occasionally need to hustle a few hours on the weekends to accommodate urgent projects.

5. That doing your taxes quarterly is extremely difficult.

FreshBooks is my savior for this very purpose. I use its app to snap photos of my expense receipts and it allows me to easily generate P&L reports which help with paying quarterly tax estimates. It’s sort of like my sidekick.

Even more importantly, I have an awesome tax guy named Josh who helps me figure “everything taxes” out. He is well worth the money, answers my questions, and has taught me the basics of filing taxes as a self-employed person.

Yes, there is a learning curve, but it’s no more difficult than cooking in someone else’s kitchen; Once you find the tools you need, it’s easy to get cookin’.

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