Freelancers and independent contractors, are faced with wearing many hats. Most of which I was proud to wear, or at least try on. But I always managed to avoid facing legal tasks despite the fact that the life of a freelancer is filled with a constant execution and renegotiation of contracts.

Yet I never seriously considered getting legal advice. I would just draw up my own contracts, throw in some legalese like “herein” and “thereafter” and hope it was sound. When you work in a company of one (or even two and three), writing these kinds of documents and agreements can be an incredible time suck. Sound familiar?

Let’s face it, legal “anything” is expensive and wrought with jargon that I’d rather not spend time untangling. Furthermore, finding a lawyer that I felt understood what I was doing and that could work within my sensitive budget was impossible. I do not exactly fall into a category of business owners which lawyers line up to help.  I don’t exactly feel the love from attorneys, if you know what I mean.

It’s not like these lawyers did not want to help me, but it was more of a pain than a benefit. Like so many freelancers and small businesses, my concerns were typically short lived and I was extremely sensitive about my bill.

As business grew and time went on, I used these documents dozens of times. Every time I had to grab one of my homemade templates for an agreement or SOW, I cringed at the sight of my poor language and weak protection. I wondered what would have happened if something went wrong.

I’m not going to tell you the story about how I got sued by a client, or when one of my relationships went awry. Luckily, I never had that experience. Of course, it was entirely possible.  The fact is, I still needed legal guidance beyond just a form document – even just a little bit – to make sure I was pointed in the right direction and not royally screwing myself. At a minimum I needed to know what to look out for and avoid. In the area of software development this can be more complex than a generic website can provide.

Be honest with yourself and get a little legal guidance.  The resources and lawyers are out there, although we are making it easier to access.  If you need help finding a lawyer for your freelancing business or some good legal resources, let us know at  We are serious about this.  We, the founders of UpCounsel, will personally help you find what you need.

This is a post by UpCounsel CTO, Mason Blake. Mason has served as lead engineer at several companies and growing startups. He has also been an independent contractor at various times in his career and faced many of the frustrations that so many startups and small businesses face when it comes to legal and tax advice help. If you’re a company hiring an independent contractor, or an independent contractor needing documents and insights, see our previous post on this topic.

About the author

Mason Blake

Mason Blake

Mason is the co-founder of UpCounsel. Mason is an experienced technologist and excited about the future of employment. He is responsible for all product, engineering, data and technology teams at UpCounsel. Before founding UpCounsel, Mason served as the lead engineer for several startups throughout his 15+ year career and then went on to form his own consulting company.

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