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The Entrepreneur Resume and Cover Letter: What to Include?

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If you need to get a job after running your own business for a while, creating the perfect entrepreneur resume and cover letter can be a delicate issue. How do you convey your entrepreneurial activities to a potential employer, and are there times when it is just best to leave them out?

The Entrepreneur Resume and Cover Letter: What to Include?The truth is if you approach your self-employment in the wrong way, it can end up being a red flag that may make your potential employer think you are trying to cover a negative job experience or an unexplainable gap in work. But, if you go in to the process with the right attitude and spend a little time researching your options, you can turn almost any period of entrepreneurship or self-employment into a plus that will make your resume positively stand out among the rest.

Why Entrepreneurs Struggle to Write an Effective Resume

A brief look at what some headhunters, recruiters, and business owners have say about how you should handle your self-employment on a resume may leave you scratching your head in utter confusion.

On one hand, some claim that seeing self-employment and entrepreneurial activity on a resume or cover letter is a plus, since it can be a sign of initiative, resilience, and the ability to manage time. People who have run a successful small business will also know how to network, find creative solutions to problems, and generally develop a deep, practical knowledge of the industry they were serving.

On the other hand, others strongly discourage the mention of self-employment or freelance work since just seeing 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. Plus, some job seekers falsely claim that they were self-employed in order to cover up long periods of unemployment. They do this because entrepreneurship is difficult to verify, and it just looks better than a large, unexplainable gap between jobs.

Of course, what you should end up doing really depends on the circumstances of your situation. But, if you already have a future job in mind, it will be much easier to figure out if and how to list your self-employment on your resume.

Tips for Creating a Killer Entrepreneur Resume and Cover Letter

That said, here are a few points to consider before you send out your resume or cover letter to potential employers. At the end of this post, I have included several free resources to help you write the most effective entrepreneur resume and cover letter possible:

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. So, you want to ensure that any mention of entrepreneurial 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?

Say, for example, 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 significantly adds to your level of experience or qualifications in your field. Ask yourself: what did you learn or gain from working directly with clients that would be of value to your potential employer?

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. Again, you want to highlight the things you gained from your self-employed work experience that qualify you as a perfect candidate for the position you are currently seeking.

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:

  • 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. You can see and download some sample resumes and cover letters for entrepreneurs at the end of this post. Alternatively, there is a nice collection of how-to articles, guides, and  sample resumes over at About.com.

Get some help creating and formatting your resume and cover letter.

Since it may be hard for you to pick out any mistakes, ambiguity, or weaknesses in your own resume or cover letter, it’s really a good idea to have other people take a look at it. You should show a draft version of your resume and cover letter to those who you can trust to give you honest feedback- especially if they have experience working in the same field you are trying to get a job in. You could alternatively ask the advice of a professional job search consultant or career counselor- whether directly or through a platform such as Quora.

Don’t be a afraid to be yourself.

Though many job search experts 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 you are seeking, you may actually stand a better chance of landing the job by letting more of yourself and your personal accomplishments shine through. Get those creative juices flowing!

Free Entrepreneur Resume Examples and Sample Cover Letters

Here are several sample resumes and cover letters for entrepreneurs and the self employed that you can download and adapt:

Sample Functional Resume 2 (17.0 KiB)

Sample Functional Resume1 (43.0 KiB)

Sample Functional Cover Letter 1 (13.0 KiB)

Cover Letter Template (13.0 KiB)

Reverse Chron Resume 1 (15.5 KiB)

Reverse Chron Resume 2 (19.5 KiB)

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