Myths About Freelancing

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Making the jump from an in-house role to full-time freelancer can be terrifying. But once you get through the initial scare and get rolling, you’ll realize the security you felt working for a company full-time is actually a bit of an illusion.

Working for a startup, for example, can be a risk. As the company quickly grows, often with shifts in management, it can be somewhat commonplace to cut or replace roles. But if you’re freelancing or consulting and working with several clients at a time, even if one no longer requires support from a contractor, you’ll still have a portfolio of clients to service. In this sense, it’s a bit of an illusion that full-time roles are more secure than being self-employed. (One egg in basket v. several — you do the math.)

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. (If you haven't heard, the contingent workforce is a pillar of the future of work... )

Myth 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 not as if you have a Rolodex of managers breathing down your neck; it’s quite the opposite. The fact that you were brought in means you are a specialist of some sort, and your clients trust you to do your own thing. They aren’t on a mission to slow you down with unnecessary micro-management.

Myth 2: You don’t get an intimate picture of the companies you work with because you’re not in-house.

Again, not the case. As a freelancer, you see the company through a different lens than in-house employees, and that's valuable. As a freelancer, you intimately understand how outside talent is managed (often an indicator of company culture internally) and you can provide customer-like insights to your clients given your distance from internal affairs. For example, I was asked to beta test a new feature for one of my clients and they appreciated my “one-step away” perspective.

You can also gather a lot about a place just by being inquisitive. I’m constantly asking clients about how things work internally to gain a deeper understanding of what’s important to the business. They’re usually excited to share.

Myth 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 are your paying client after all, so you don’t want to rock the boat, right? Not the case, in my opinion. It’s all about approach.

If you disagree with a certain strategy and feel meek about speaking up, remember that one of the reasons your client is paying you is so you can provide your specific area of expertise. Sure, there are a lot of freelance projects that are assignment-based, but most long-term clients want your opinion and welcome varied perspectives. Respectful, open communication is key to any healthy relationship.

Myth 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 business hours (I typically work 9 a.m. to 6 p.m.), and stay focused on production for clients versus giving into the temptation of working on personal projects during business hours, you can work hours comparable to what you’d work in an in-house role.

I was moonlighting during 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. After I was up and running, I got my Sundays back, though I do occasionally hustle on the weekends to accommodate tight deadlines.

Myth 5: Doing your taxes quarterly is difficult and annoying.

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.

Even more importantly, I have a CPA I trust who has helped me navigate paying taxes as a self-employed business owner. He is well worth the money and quickly answers my questions whenever I have them. You’ll know you’ve found a great CPA if they are continually working to educate you, so you can make more informed decisions pertaining to your business finances on your own.

Yes, there is a learning curve with freelancing, 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 cooking.

Considering freelancing? Here are six signs you’re ready.