How to Include Self-Employment & Freelance Work on Your Resume & Cover Letter

With the unemployment rate still soaring throughout America, many recent college graduates in addition to seasoned professionals have turned to entrepreneurial pursuits and freelance positions. Even of those who still have a job, running a “gig” on the side is pretty common these days.

But this raises a question: how do you convey your entrepreneurial activities to a potential employer, and are there times when it is just best to leave them out?  

from self employed to dream employed

A brief look at what some headhunters, recruiters, and business owners have say about how you should handle your self-employment or freelance work may leave you scratching your head in utter confusion. Some claim that seeing self-employment or other entrepreneurial activity on a resume or cover letter is a plus as it will be seen as a sign of good work ethic, resilience, creativity, and time management among other things. Others, however, strongly discourage mentioning most self-employment or freelance work since just sseeing that you are currently self-employed is a red flag to headhunters and business recruiters that you are likely to pack up and leave at whim.

The solution, of course, is that it really depends on the unique circumstances of your situation. That said, here are a few points to consider before you send out your resume or cover letter. At the end of this post I have included several free resources to help you write the most effective resume and cover letter. You can also use an online resume builder which can help you creating a professional looking resume.

What are the circumstances of your self-employment?

Taking on a new employee is not a simple matter; it represents a significant investment of time and money especially for smaller companies. Thus, you want to ensure that any mention of entrepreneurial or freelance-type work adds undisputed value rather than a red flag for some perceived inadequacy. You have to look at your self-employment situation as someone on the outside would. Is it something you are currently doing as a temporary stint between positions or do you have a longer term strategy? Is it an addition to a full time job and therefore might point to a possible conflict of interest or priorities? What is your current and future level of engagement? If you take up freelance projects infrequently and do not intend on making freelancing your full time career, then it may be better to omit them from your resume. The only time you should really list occasional freelance work is if it allows you to cover any gaps in your professional career.

On the other hand, if you freelance regularly, for relatively long periods of time, or have ever owned your own business, than it may be a good idea to indicate that experience on both your resume and cover letter. Highlight those attributes of your self-employed work experience that qualify you as a perfect candidate for the position you are currently seeking.

from self employed to dream employed

Before writing your resume, pay attention to your own attitude.

How do you personally feel about your entrepreneurial or freelance work? This is important because your attitude will come through in the way you present your employment situation and anything that you may have gained from it. If you yourself value certain aspects of your self-employment, even if you are not in love with everything that you do, then you will be in a better position to convince employers of that same value. Moreover, the fact is that employers will either love or hate your entrepreneurial and/or freelance experience. You’ll probably want to work for the ones that value it—the others will take themselves out of the picture by not contacting you.

Choose your resume format carefully.

The way you choose to structure your resume will depend on several factors, namely:

  • The nature and duration of your freelance or entrepreneurial work
  • The amount and quality of your “traditional” work experiences
  • The needs and culture of the company to you are seeking to work for
  • Overall trends shaping the industry you want to work in

Resumes generally fall into one of two formats. They are either reverse-chronological, listing all your experience from the most to least current or functional, highlighting various skills and accomplishments within given categories. If the majority of your work experience includes a series of freelance projects, you may want to consider a functional format. A functional resume places more emphasis on your qualifications and expertise for a particular position rather than where you worked and how long you were there. So, if you were applying for a position in sales management, with a functional resume you might choose a category such as “Sales Experience”, as opposed to a title like “Sales Manager at XYZ Company.” A functional resume is also a good option for covering up any glaring gaps in your employment.

Get some help creating and formatting your job search documents.

Since it may be hard for you to pick out any mistakes, ambiguity, or weaknesses in your own resume or cover letter, it definitely pays to at least show these documents to any acquaintances who you can trust to give you honest feedback. You could alternatively ask the advice of a professional job search consultant or career counselor. Finally, there are many sites offering tools, templates, and other information that provide small business owners and the self-employed with the resources needed to create professional, attention-grabbing resumes and cover letters.

Below is a list of some quality resources that you may find helpful:

from self employed to dream employed

If any of you know of some other good resume-building resources then please let us know in the comment section below.

And in closing, my opinionated, non-job search expert two cents….

Though many experts and even the samples listed above suggest the use of standard structures, phrases and “action words”within your resume and cover letter, don’t be afraid to let your own voice come through (as long as you aren’t too far on the side of casual, and the documents are grammatically correct and spell-checked). Depending on the job, some decision makers may be literally sitting in front of dozens or even hundreds of resumes and cover letters that all say, ” I have the skills and experience needed…” These “cookie-cutter” phrases may actually cause the reader to just move on to the next applicant.

In other words, at a time when the competition may be fierce for the position(s) you are seeking, you may actually stand a better chance of landing the job by letting more of yourself shine out and by letting some of your creative juices (if you have any) flow.