Mentoring and Homeschool Leadership Retreats

From May 9th through May 23rd I worked on the inaugural trip of Homeschool Leadership Retreats, led by my friend Blake Boles. It went splendidly; even more than splendidly. We had 7 campers total – 4 girls and 3 boys ages 14-18. They spent the two weeks getting to know Ashland, Oregon; they created internships, audited college classes, conducted interviews, got certifications, and many other wonderful things, all on their own. We also took them to a ropes course, on PCT hikes, to plays at the Oregon Shakespeare Festival, a tango lesson, etc. In the evenings, Blake taught workshops on many aspects of self-directed learning and creating opportunities for oneself in the world.

In the end, I was able to see the campers walk away with copious amounts of confidence, direction, and tools to go out and achieve their dreams. It was a great experience, both for campers and staff. I will certainly never forget it. Here’s a photo album of some of the highlights of the retreat: HLR Spring Retreat Photos.

During the retreat, a friend contacted me and asked if I could write up something on Homeschool Leadership Retreats and my thoughts on mentorship (especially in the context of the aforementioned HLR) for a speech she was planning to give at the LIFE is Good unschooling conference last weekend. I did, and I thought I would post what I wrote up here as well.

Oftentimes when I think of the word “mentorship,” I see some old yogi master walking through some Eden-esque garden with his little follower, philosophizing about the universe and speaking in proverbs. However, these past few months I have come to realize that the word, in this day and age, has a completely different meaning, that is simply all too wonderful.

Mentors lead and challenge; but they also listen and understand. A mentorship can consist of two people of any age difference. It can be intentional or accidental, or anything in between.

When I was first asked to be on staff for Homeschool Leadership Retreats, I was excited solely that I would get to “learn to work with ‘kids’ more, and people in general,” as that, besides “working on camps,” was one of my many vague, ill-defined goals. As the spring retreat approached, this intention got rather lost in the hubbub of getting ready to leave and the traveling I did beforehand, but that was good to sort of clear my mind and give me a fresh outlook once the retreat started.

It was the first night the campers got there that I more fully realized why I was there. These kids – really not much younger than I am – needed and wanted direction and confidence. And I was in the position to both show and give those things to them in the course of the retreat. Suddenly – click! – there was my purpose, there was my reason for being in Ashland, Oregon on May 9th. To give of myself in these areas in the same way others have given of themselves to guide me before (and who continue to do so).

Of course, I will throw a dictionary definition in here for good measure. Merriam-Webster Dictionary Online defines a mentor as “a trusted counselor or guide” (italics mine). I see mentorship as something which centers on trust; it can’t function without it. I can say “oh, I want to be this great leader-person who sets good examples all the time and gives a crap ton of good advice”; or, as someone being mentored, I can say, “I want to be shown the ways of the world through this wise persons’ eyes and have a strong leader with good advice.” Well, those are great and all, but they really mean nothing if a trusting relationship between the two people in the mentorship has not been established. However, trust isn’t something that really consciously happens, though; and forcing it is not really a good idea.

Trust is a two-way street. Not only does the person I am mentoring need to trust me, but I need to trust them as well. For me, trust is built from being personable; being real, being true, etc. A mentor can admit to making mistakes. I used to think that was a bad thing to do – after all, I am supposed to set a good example, right? Therefore, admitting I screwed up somehow or another is simply out of the question, correct? No; I’ve found it to be the opposite. I can trust the person with the good and the bad. When I first discovered this, I was telling a younger friend about a big no-no I had done – afraid I would lose her respect forever. But, to my surprise, a big grin grew on her face when I was done telling what had happened, and she said “Wow… I just want you to know, Jessica, that I look up to you so, so much!” And she helped me feel respect for myself again, despite feeling like I had really screwed my life over.

Mentorship starts with friendship. Basically, mentorship is more of something that grows rather than something that just starts. Not to say that doesn’t happen; and if it does, friendship then grows out of mentorship. It’s really more of a cycle. It can begin with a single conversation, or an activity done together. Those sorts of things are inextricably conducive to building that essential trust – because trust is built from sharing… again, on both ends, not just the mentor getting a bunch of information out of the student (or whatever the “mentoree” should be called) so he can give advice, and not just the mentor pouring out copious wise words and quoting adages. Like I said, it is essentially a friendship, and friendships are developed with exchange of stories, thoughts, advice, musings, and shared activity.

Mentorship is such a wonderful gift for both the mentor and the one being mentored. They trust each other; they help each other along; there is a mutual respect; encouragement is exchanged. It is special, it is important, it is a lovely and wonderful thing. And being on Blake’s leadership retreat as a volunteer mentor/participant/dishwasher has really taught me so much about it that I do not think I would be able to understand before now.

On the note of Life Without College, I think mentorship is very important at this age – both to have a mentor, as well as being a mentor of some sort. It’s like teaching; they say when you teach something to someone else, you learn it better yourself. I’ve found it is the same with mentorship. Leading and guiding another person, whether you are doing so consciously and intentionally, or unconsciously and unintentionally, helps you guide yourself and understand yourself better, which, in turn, helps you be a better mentor.

What are your thoughts on mentorship? Have you ever mentored someone, or been mentored? What sorts of experiences have you had?



2 responses to “Mentoring and Homeschool Leadership Retreats

  1. While I can’t say I’ve had much experience with mentoring/being mentored as a whole, the one time I’ve ever been involved in a class setting was martial arts (Aikido, if anyone’s curious).
    In our particular dojo at least, all the students were encouraged to pick a mentor after around three months; the mentor could be anyone 4th Kyu and up (that’s about the third rank, and not too hard to achieve). I’ve been both mentee and mentor in that situation, and while for the most part there was always someone around to help anyone out, it was always nice to have a mentor around looking out for you, giving you a heads-up on your next rank testing requirements (and as a mentor, it was always an incredibly proud moment to watch one of your mentees just totally nail everything on his/her rank tests).

    …and I don’t know if “mentee” is the technical term for it, but it’s what we all used. (Firefox spellcheck tells me mentee isn’t a word, but it also says spellcheck isn’t a word.)

    On another note, I’m curious about something; the one downside I’ve always run into with my homeschooling/unschooling is the lack of a large social setting to get involved in, so I’m even now still on the lookout for like-minded people I can socialize with.
    How do you (you being Jess, or anyone who feels like replying) feel about it all? These HLRs seem like a great experience, and I’d imagine there’s a lot of other options out there as well. I’m curious mostly about how other homeschoolers deal with the “downside”.

  2. Geo – that sounds like a great situation. I like that the “mentees” had to pick the mentor – taking the initiative. That’s pretty awesome.

    Spellcheck is overrated. 😉

    Actually, I have to admit that I have never really had that social setting downside. Admittedly, I grew up in the largest homeschool community in North Carolina, so that would explain it.

    However, I know that there are tons of teenagers in the same sort of situation as you. There is actually a “hidden” “underground” entire unschooling community across America, and even around the world. There is at least one symposium of unschoolers basically every month, somewhere in the US; and there are tons of camps, etc., like HLR. Blake has been compiling a list of these here:

    Not Back To School Camp, run by Grace Llewellyn (, is the biggest “unschooling social setting.” While I have never been myself, I know tons of people who have, and so many lifelong connections are made through it; I have heard it is wonderful.

    This sparks another idea for a more detailed post about finding social structures of unschoolers/homeschoolers. I know people who have moved to large unschooler hubs, like Seattle and Portland. I definitely want to blog about this more, so if you (or anyone else) have any more questions on this type of thing, let me know.

    Does anybody else have any thoughts on unschooler/homeschooler communities?

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