from self employed to dream employed

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.


  1. says


    Great post.
    I recently revamped my resume and included my blog/freelance work on my resume. Intially I was reluctant to do so, and after talking with a friend, who also happens to be a recruiter, I worked with her and created a new resume. And also included my blog in it.

  2. head_exposed says

    This is a very informative post for the increasing population of freelance and self-employed workers. I for one, agree that self-employment and freelance work should be put in the resume because these endeavors tell the employer that you are a talented and driven worker. More employers should see it that way. Self-employed and freelancers are self starters. Wouldn’t you want them in your company?

  3. says

    This post really hits home for me. I have made a living on websiites and blogging for the past ten years, but now that times are tough I don’t even know how to approach the real world jobs because it seems like all of the 9 to 5 jobs aren’t interested in what you’ve done online.

    At least that’s the feeling I get where I live. Employers are more interested in advanced degrees than they are in experience.

  4. Adam Gottlieb says

    One on hand, it’s very much an “employer’s market” these days- so many qualified people looking for jobs and hiring is still pretty weak.

    But, in many cases a job applicant’s attitude can really make a difference, regardless of formal, traditional training and experience.

    For example, if you have actually been able to make a living for ten years blogging and managing websites, then that’a a pretty amazing thing right there, and may have come with many skills and experiences that employers crave: time management, discipline, networking abilities, critical thinking, hard worker. It’s all in how you package it.

  5. Adam Gottlieb says

    I definitely agree with you… But understand from the employer’s perspective they may be afraid to hire someone who has focused on freelance work because these employees may be more likely to leave (a freelancer is by necessity and definition a bit of a nomad), and if employees leave then they take with them all of the time and money the employer invested to train them. If you sense that a potential employer is hesitant to hire you because of this issue, yet you intend on staying with the job, then you have to make a point of reassuring the employer in this area.

    Really, it all boils down to how you give over (read: sell) your freelance/ self-employed work and what kind of job/employer you are considering.

  6. Adam Gottlieb says

    Smart move. It will add a lot of dimension to your credentials… It takes a lot of work to have a successful and growing blog- especially in personal finance, which is a very saturated, competitive topic.

    Good luck.

  7. says

    I do agree with you that PF blogging is quite saturated, but I enjoy it. The learning curve on money is equally as good, so that’s something that really has no price, but tons of value.

  8. says

    In my experience working with job seekers, if you freelance regularly, for relatively long periods of time, or have ever owned your own business, than it is generally a good idea to indicate that experience on both your resume and cover letter.

  9. Jennifer says

    How should a person, who left mid-level corporate life 14 years ago to raise children, but who has done Independent Consulting work off and on for six of those years, list those past 14 years on a resume? One assignment lasted 3 years while others were anywhere from 9 months to two days.

    I have been warned not to put Full Time parent (a sure thing to get your resume trashed I’m told), but almost feel like I am being deceptive if I put Self Employed. Also, in today’s times is it preferrable to put Self Employed or Entrepreneur?

  10. Adam Gottlieb says

    First off, I don’t think calling yourself “self-employed” is being deceptive unless you give explicit indication that you were working (unfortunately most employers won’t recognize all the house work) during all those 14 years. I don’t think you should say that you are an “entrepreneur” unless you really feel that you are.

    Second, in your case, it’s probably best to go with a functional style resume- ie list and highlight your skill set and experience first while under-emphasizing your actual chronological employment. The following link is for a free functional resume builder. I suggest you play around with it, and then have someone knowledgeable in hiring or career counseling look it over. Good luck!

  11. Brant Kurelko says

    This is a really good article on how to put freelance work on a resume. The point about attitude is very important. Recruiters are looking for people who feel confident about their experience and their ability to use it to do the job.

  12. Alexandria Bogner says

    It’s a good time to start making some plans for the future. I’m glad I read this post. I didn’t realize how important my freelance jobs could be.

  13. Dave says

    Thank you for this blog and I’m going to ask you for an opinion on my situation. Even though you deny being a “job-search expert” you know more than many.

    A summary of my situation is:
    late 70′s and early 80′s: I was a programmer and department manager
    mid 80′s: I had to take a medical leave from traditional jobs and tried to make it freelancing
    early 90′s: Freelancing wasn’t working so I got on disability
    early 2000′s: I had surgery and went to school to get an AS in CS.
    Mid 2000′s the economy crashed and I had to move inland and restarted freelancing with no portfolio
    early 2010′s I got a business license and started developing and selling Drupal based web-sites, trying to make freelancing a little more formal.

    Besides the problems you mention I’m running into the fact that people are naturally uncomfortable supervising someone twice their age.
    I have less experience than someone 30.
    My work habits are not as well established as most 50+ year old workers.
    On a traditional job application you see something suspicious, I’ve had people think I was in jail for 20+ years.
    I don’t fit on automated resume builders (linkedin’s experience section for example) since I was not on W-4′s for traditional jobs.

    I have the skills, but I have problems proving them.

    Resumes and coverletters have been my foe for years. Because of you I am going to look at mine once again

  14. Adam Gottlieb says

    So here’s my 2 cents…

    One of your biggest strengths is persistence… You came from disability leave and went back to school and persisted in freelancing even under difficult circumstances. Many younger workers these days are job hoppers. They’ll stay for a year or two and move on to something better or different- especially in the tech industry. Ironically, you want to be applying at companies that are specifically looking for people who will stick around for a while. They should also be open to hiring an older worker- don’t waste your time where this is not true.

    In terms of proving your skills, you didn’t mention if you have a portfolio of previous work or if you are getting recommendations from satisfied customers. This is important. You should also try to build connections (if you aren’t already doing this) via LinkedIn. Everyone and his grandmother advises people to use LinkedIn to build a network and get leads. But, if you use LinkedIn like the majority of the people there, then you won’t get very far. Do you want to know what will make you stand out? Get on there, find 3 groups to join, read people’s questions and really care about answering them or offering useful information. People will take notice, because you will be real, and it could open the door to your next job.

    Good luck!

  15. Anon says

    I have been unemployed now for almost 4 years due to severe medical issues. As of right now it is unknown if I will be able to return to work as my Dr’s have been putting me through MANY procedures and tests. I am currently applying for disability but SSI/SSD has been giving me hell. If I win my case, I will not return to work. If however I do not I will be forced to return to some kind of severely limited work and it will not be easy but one must get money for my medical bills ect. How does one update their linked in profile for their current job if you don’t know if you will be able to return to work? I was thinking of saying I was doing freelance work for self but I have read that may not be a good thing to do, as well, I do not want to put down that I have been sick ect.. Any suggestions? Thanks!

  16. Adam Gottlieb says

    Hi Anon,

    I don’t know what you do, but I would suggest building a blog or website around your particular area of expertise, monetizing it with Adsense, and then putting on your LinkedIn profile that you currently run this site as your latest “job”. You should also join three industry-specific LinkedIn groups and make contributions to them where you can. The reason for this is that you are keeping your LinkedIn profile active; it shows your still involved in the industry- even if only in a passive way.

    It doesn’t sound like your medical condition is something you can hide, and you shouldn’t. But you also shouldn’t blatantly stick it in front of a potential employer’s face.

    Good luck getting disability… You really have to be on top of them at the DDS or else you won’t get anywhere… and even then, you still may not get anywhere. I hope it works out for you.

  17. Will says

    Love the post and it was what i was looking for to get my resume going. But i still hits some walls when trying to finish it. I have a BS in Biology from a Great School and never work a 9-5 job. I started selling on ebay in College to get me that extra cash that college students always need, but when graduation time came i already obtained Top Rated and Power Seller status on ebay and business was booming (Last year 90K in sales). Almost two years have past since graduation and i want that retail experience. I’m in NYC job hunting specially for a retail part time job. I consider myself very successful in what i do, but employers may see me as one of those who not going to completely there on the job. I don’t want to be seem bragging and complementing myself on paper. How can i convince them to give me a interview?, that’s all i need


  18. Adam Gottlieb says

    Realize that you’ve got more real life “retail experience” than most applicants seeking those positions (even if they technically had a 9 to 5 retail job). All you have to do is basically say in your cover letter or email:

    “I have a BS in Biology from a Great School and never work a 9-5 job. I started selling on ebay in College to get me that extra cash that college students always need, but when graduation time came i already obtained Top Rated and Power Seller status on ebay and business was booming (Last year 90K in sales). Almost two years have past since graduation and i want that retail experience. I’m in NYC job hunting specially for a retail part time job. I consider myself very successful in what I do”

    And then STOP. Once you get to that “but” you’ve just lost the chance for an interview. Complementing yourself is NOT bragging. You’re just stating facts. You’re good at selling and running a business (which is what it is). You can prove it by the results you achieved. You persisted at it for 2 years, so you’re not by nature a flaky person who will suddenly up and leave. They’d be crazy not to at least give you an interview. Good luck :)

  19. Elise says

    Hi Adam,

    Thanks for writing the article. I’ve only just begun a based-at-home “internship” (in quotes because I’m doing what any assistant would do and am not receiving much direction). I’m looking for a full-time job and the gap since my last position has grown to about 2 months–when I apply to jobs should I put my “internship” as a “freelance” position or should I put it at all? At what point in an employment gap do employers begin to look for an explanation? Thank you in advance!

  20. Adam Gottlieb says

    Hi Elise,

    I think 2 months is still a small enough gap that you don’t need to mention your current position- especially if you have some solid previous job experience to highlight. If, however, your job search stretches out beyond 4 to 5 months, then you should mention it (whether or not you label it as “freelance” really depends on where you’re applying) and just highlight any key skills and responsibilities that would be relevant to the position you are applying for. You could also mention that it is a position in which you “took initiative” and was able to “work independently”… in other words, turn the position’s weakness into a strength.

    The other option would be to write up the functional resume mentioned in the post.

    Good luck.

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