Pros and Cons of Freelancing

Holly A. Sheriff, MSLS, MCC, CCC, PCC, LPCC, CPP • September 2, 2021

Originally published on 08/30/2009 Updated: 08/30/2011 Latest Updated: 09/01/2021

No part of this publication may be reproduced, distributed, or transmitted by any means without prior written permission or without using the sharing widgets provided, if any. Copyright 2009 Holly A. Sheriff. All rights reserved.


Many paralegals dream of freelancing, but they allow mind viruses, limiting beliefs, and other fears stop them from cultivating their dream into a reality. I could waste your time and give you stats regarding “the state of freelancing and list of boring stats that prove why you should go for it.” But, why? You already know you want to freelance, and you already know the benefits you want to achieve. So, why waste your time? I am not going to waste your time. What I am going to tell you is the hard truth:


Freelancing is not  a cookie cutter job. There are many pros, cons, and other variables that make a great choice for some paralegals and not such a wonderful choice for others.  The journey is different for everyone.

PROS CONS
Flexible work schedule Inconsistent income or pay
Acquisition of the new skills you want No traditional job security
Quality and type of work is up to you Nobody covers your benefits
Work from anyway (you’re in control) Increased overhead | tax disadvantages
Tax advantages (write off and dedications) No set hours (Depending on your personal discipline)
Ability to be your own boss Family & Friends have difficulty with distinguishing work hours vs. personal time
You don’t have to commute — it’s your choice There is considerable amount of financial investment – unless you’re independently wealthy this is a concern for most paralegals.
You get to be creative You have to learn how to market yourself

In all honesty the pros and cons can vary from person to person. Although most freelancer regardless of industry have the same pros and cons depending on their personal discipline with working from home or for themselves. As you can see from this list above there can be a pro for one and the same thing be a con for another person.

Final Words: "Friends don't let friends freelance alone.™"


Making the decision to go into freelance is a big decision. It can also be overwhelming, scary, and frustrating. BVP coaches can help. If you found this blog post a helpful roadmap but you need a cheerleader, give us a call – we would love to help you! 

Live Your Best Life

Holly A. Sheriff, MSLS, MCC, CCC, PCC, LPCC, CPP is an experienced, seasoned paralegal and certified empowered action coach specializing in accountability, focused action, and goal achievement. Holly’s holistic approach brings clarity, direction, and positive support for her clients. She helps clients live their best life, by filling the gap between where they are now and where they want to be.

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