Taking The Freelance Plunge: Crazy Idea?

Chris Varones

“I think that maybe inside any business, there is someone slowly going crazy.”


That was Walter Heller’s observation about entrepreneurism. And yet so many people consciously make the decision to go into business for themselves, assume risk, face uncertainty and live with sacrifice every year. To be sure, starting, owning and running a business is not for everyone. But those seriously thinking about doing so should reflect on five key questions to help them determine if they can and should hang out their own shingle:


Taking the Plunge: “When” is a big question for people thinking about going on their own. In most cases, a key life event becomes the trigger for someone to go on their own: you moved to a different location, you got laid-off, you got married/divorced; you cheated death or you retired. This doesn’t mean someone can’t consciously give up his/her job as an employee and take the big go-it-alone step; it most definitely happens. It just very rare. The key thing is to recognize a life-changing moment when it happens and do something about it. Key takeaway: Recognize a life moment when it happens and have a serious conversation with yourself and othersl


Start with Why: A new product, a brilliant idea, a fresh approach. These are the things that new enterprises are built on. But business-owners need more than a great idea to sustain themselves and thrive. They must have an over-riding, self-motivating passion not just for what they do, but why they do it. As author Simon Sinek notes, customers don’t buy what you do, they buy why you do. Key takeaway: Ask yourself why you want to do something before you ask yourself how, when, where and to whom to market to.


Managing the Work Week: The short answer here is your work week is up to you. If you want a 20-hour week so you can make time to ski in Vail, or 70 hours a week because you can’t say no, that’s up to you. The simple reality is that an independent contractor or entrepreneur assumes the responsibilities that were reserved for management-level employees or the back office when they were employees. That means longer (tedious) hours (i.e., servicing clients, attracting new ones, balancing the books, completing taxes, invoicing and filing expenses, etc.). Key takeaway: Determine many hours do you (and others you hire) need to work to maintain the lifestyle you want for yourself and your family.


Working vs. Growing: One of the biggest mistakes people on their own make is not knowing who they are (i.e., what kind of business they have). Independent contractors, for example, are people who eat what they kill. They work project-to-project and have minimal or no interest in growing. Entrepreneurs, on the other hand, always are thinking about tomorrow. They are freed up from most the day-to-day work because they hired someone else to do it. This allows them to network, meet new people, do public speaking, market themselves and, in a word, grow. Knowing who you are and playing to your identity will not only help ensure financial security, but help keep mental sanity. Key takeaway: Build your business and service your clients around the kind of business-owner you want to be.


Living with Failure: Are you willing to fail to succeed? That’s a question all people on their own face and deal with on a daily basis. But the people who achieved greatness almost always experienced failure in their lives. from Abraham Lincoln to J.K. Rowling; from Henry Ford to Oprah Winfrey, nearly everyone who achieved individual greatness hit the bottom and, in some cases, many times. But they never gave up. And because they didn’t, failure became merely a speed bump–a learning moment that was temporal and that didn’t hold them back. Key takeaway: When you make a mistake, write down its lessons and look it regularly so you can repeat what you do well and avoid where you faltered.


Chris Varones is founder and principal of Aesop Communications Group, a communications consulting firm dedicated to the idea that clients with good stories can do great things. Aesop specializes in reputation management, issues management, labor communications and public affairs. Chris can be reached at chris.varones@aesopgroup.com.

5 thoughts on “Taking The Freelance Plunge: Crazy Idea?

  1. Hi Ron, I stopped by your blog via the #EntryPR group on LinkedIn. Loved this post. I’ve been trying to find my way breaking into freelance consulting and this was very helpful.

  2. Hello Chris,

    It’s great to read more motivation to “go instead where there is no path and leave a trail”. Are there any web communities or educational programs that you suggest for a novice entrepreneur? What are a few precautions that can be overlooked from inexperience?

    Thank you,

    Jaclyn. A. Bisgard
    Southeast Missouri State University

  3. Jaclyn: I’d recommend signing up for Harvard Business Review and Smart Brief emails–lots of good stuff delivered every day for entrepreneurs and those who want to be one. Also, check out http://www.failureclub.com. Inexperience is not an entrepreneurs friend. An entrepreneur becomes successful by taking their experience to the next level. Bottom line: get experience and show that you can do it better. Good luck.

  4. I was wondering if you ever considered changing the structure of your website? Its very well written; I love what youve got to say. But maybe you could a little more in the way of content so people could connect with it better. Youve got an awful lot of text for only having 1 or 2 images. Maybe you could space it out better?

    1. Thanks for taking time to share your suggestions for improving my blog. You’re reading my mind. I do need to do some work on it. Hard to do when working full-time and keeping this blog going, now entering its 11th year of at least four posts a month. Only one slight change in those years, so you’ll motivate me to tackle this in the near future–or at least during my winter sabbatical.

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