Recently I was asked to review a cover letter from a bookkeeper/accountant who for many years had been an independent contractor (IC), and who is now seeking a full time position. Luckily for her, she has had a number of very long-term clients, who have kept her very busy, and she has not been at a loss for work. While raising her family, being independent provided her the flexibility of time and scheduling that she needed as a parent. But now that her children are grown and on their own, she thinks having a regular job, with regular hours and predictable pay would be an appropriate use of her skills.
In the conclusion of her letter, as she was summing up her reasons for applying, she stated,  “I’ve been longing for a permanent full time position. I spend too much time marketing myself and would rather be doing what I do best, accounting.  Being part of a team is also something I miss as a consultant.”
Certainly her letter reflected her honest desire to work as an employee for someone else.  But in the process of conveying her desires to have a job, emotions like frustration, annoyance, maybe even desperation can too easily be interpreted from the tone of her letter.  Are these traits that will go over well with an HR person or potential employer?
How would a prospective employer interpret the use of the word “longing”?  Would an employer think: “Why did she stay self-employed if she was so unhappy?”  “Would this job be able to fulfill her needs?  “Just how long has she been looking?”  “She’s seems frustrated for a long time, and from her years of working independently she may be difficult to please.”
But her letter still states that she spends too much time looking for work rather than doing the work.  These are attitudes of frustration and annoyance, intended or not, and her comment sounds like she is complaining.  Sure, these attitudes and experiences are real and true, and common among the self employed who spend too much time trying to generate the work rather than doing the work they love, but these kinds of emotions do not convey a comfortable feeling to a prospective employer.
So to combat the possible erroneous interpretations of her needs and wants by the employers she is targeting, we agreed that it was OK for her to say she missed working as part of a team, but not to convey anything more emotional than that.  I stressed to her the importance of concisely stating what she can do for that employer, emphasizing the quality of her skills and up-to-date knowledge of accounting and bookkeeping practices, maintenance of documentation, etc. Then, when she gets called in to an interview, she can explain that being an IC satisfied her needs then, and stressing that a permanent position is what she is looking for now.
Honesty may be the best policy, but don’t tell ‘em accidentally how you really feel!  Not just in your cover letters, but in your interviewing and networking too.  Keep it all positive!