Dear Boss…

In Advocate by El Rubio9 Comments

Get Your Boss to Let You Grow Your Hair Out

The most common barriers for men who wish to grow long hair are overcoming awkward stage hair, dealing with the naysayers, or a partner who isn’t down for the flow. All too often though, the chief barrier is employment. So how do you convince your boss to let you grow your hair out?

If the company you work for, or a company you’re seeking employment with, has a policy prohibiting long hair on men, or if the boss doesn’t like long hair, you might be forced to choose between your hair and a job.

A conflict.


For most people, your job is your livelihood, not something to be trifled with. But if there were an approach you could take that would give you the best chance at growing your hair out, with the blessing from your employer, would it be worth a try?

We thought so, which is why we penned this Dear Boss Letter. Stemming from this documented case where a young man secured his boss’ permission to grow his hair out, we’ve applied the same concepts in a letter format to be used by others.

It’s purpose is to ask for leniency in support of a good cause: growing to donate. The idea here is you take this letter, customize it as you see fit, and deliver it to your boss with a request to grow your hair out.

Specifically in this letter we are referencing The Great Cut, and if it works we must insist you follow-through with your commitment—we’ll be able to help with that.

Every company and every circumstance is different, so we can’t promise it will work for you. But with a graceful approach and a selfless purpose, what could it hurt to try? And what if it does work?? You’ll be mashing southbound on Mane Street halfway to Shoulder Alley.


The Letter

Here’s how to use it:

  1. Copy and paste the text into a document or email.
  2. Download as a pdf, customize the name, save, print, sign, scan, email, fax or however the hell you want to get it in your boss’ hands.

Either way we hope you’ll let us know: how did it go? How did you use the letter? How did your boss react? IS THE FLOW INTACT??!

If you are facing this issue but you decided not to try the letter, can you let us know why?

Without further introduction, Dear Boss...


Dear Boss,

I’m writing to ask for leniency with our company policy on long hair. My intent is to grow my hair out for a charity event aimed at breaking the Guinness World Record for the largest hair donation in history.

There are millions of children and young adults who can’t grow their own hair due to alopecia and other medical reasons, who face a loss of self-esteem, self-confidence, and social acceptance. This traumatic experience can impact a child’s entire life.

There are people doing something about this. A company called The Longhairs and their charity partners Children With Hair Loss are hosting an event called The Great Cut, where they are calling for 2,500 volunteers to donate their hair.

I would like to grow my hair to donate at this event. Given permission to grow my hair out:
  1. I’ll keep my hair neat and tidy in the process, maintaining a presentable appearance at work.
  2. I will represent our company with my participation in The Great Cut and report back on my experience.

I know we’re an organization that cares about people, and I hope to be an example of that by participating in The Great Cut. There are even opportunities for our company to sponsor this event if we want to do more.

May I have our company’s support? Thank you in advance.



Let us know when you use this letter and what your experience is like. Did it work?


  1. “If you grow it….people will cut it!”
    Ok, just a play on words from “Field Of Dreams”. But you get the idea.
    Great idea in the letter, but being a former stupidvisor and having spent many years as a “suite,” I can tell you the first thing I would say:

    Me: So when is the Great Cut?
    Employee: I don’t know yet. They haven’t announced the date.
    Me: When will they?
    Employee: They said soon
    Me: You know our policy, but it does sound like a good cause. If you can get, and show me a verifiable date within the next 45 days, then I’ll approve it. If you can’t, then you’ll need to get it cut or be forced to take a leave of absence until you have s confirmed date. Not to be a hard ass, but I need ensure the company grooming standards. When you get the date, I’ll even allow or announce the Great Cut to encourage the other guys and even the ladies in our (place of business) to participate as long as they follow certain guidelines I set up so hair length can be deemed acceptable by our customers and upper management. And to ensure the rules are followed, I’m going to put you in charge of communication on this throughput our (place of business)
    If it works out, perhaps you and I can present the outcome with photos for the company newsletter and to make a follow up presentation to upper management. Maybe we can focus on challenging our other locations and our local competitors to do this as well.
    Employee: Oh Boss…I don’t care what the other people around here say about you….you are one cool MoFo!!!
    Me: and to show I’m not the prick everyone thinks I am, for each employee who signs up to participate, I will buy them a set of hair ties of their choosing from the Long Hairs collection. And as the communications director of this Charitable event, you will work with HR to inform the other male members of the company that they must sign up for the Great Cut to be able to grow their hair out. If this works successfully, then it will become an HR initiative so you won’t have to organize in the future. We’ll even give new hires the option to sign up IF upper management approves. Thanks for bringing this worthy cause to my attention. Good luck.

  2. A noble cause and everybody wins, right?!!? I hereby pledge to grow my hair long for those who cannot and will happily donate my locks in the prescribed time.

    Longhair Larry

    1. Author

      Longhair Larry! We’re with ya man! See you in 2024, keep lettin it ride!

  3. Unfortunately, this letter ends with the promise to eventually cut ones hair, always for a “good cause”, (however contrived). Capitulation, in truth. Most “long -hairs” are rightfully committed to keeping their hair, for various reasons, as they should. Resist and don’t pander to the phoney establishment! Grow it long and strong!

    1. Author

      We understand your sentiment and praise your zeal, but I don’t know that ‘contrived’ or ‘capitulation’ are the right words here. You may be aware we did in fact donate our hair at The Great Cut in 2019, where many of us still kept shoulder-length hair. While I agree longhairs should have the right to keep their hair, realize not everyone has the luxury of growing unfettered. If donating can be used as a vehicle to circumvent antiquated grooming policies, should we not promote hair growth by any means available?

      Even so we can all agree…grow it long and strong! Thanks for the comment.

    2. Ellen, to a couple of gentlemen who responded to the Indisputable Reason article, I wrote a comment the condensed version of which is that a guy should donate his hair if, like most guys, terminal length doesn’t reach his waist, but if it does, he should let it grow all the way, keep it, and proudly let it ride.

  4. A great tool for those seeking an extra motivation not just to grow but to donate. I’m looking to move jobs, hopefully a higher paying one in a management position. I may consider submitting this letter to HR when I go in for interviews. I’ll report back on my experience.

    Always a pleasure to visit the blog. Keep it going. I’ll be buying some ties as soon as I can manage a tail.

    1. Awesome BOB8! For sure let us know how it goes, we are very interested.

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