We started unschooling in 2005, right when we moved to TN. Oh, I suppose we had done some unschooly things before then, but I don't think we had a name for it, or had done any real research or anything until we ended up in Nashville. I was working for Dell at the time, and doing well. But unschooling is nothing if not an intense, personal journey, and unschooling was causing me to rethink the definition of success, and what my fundamental philosophies and joys were as a person, partner, parent, and worker. I was beginning to see and feel myself changing in subtle ways: I was less of a Type A at work, more thoughtful, more interested in process and experience than in outcome.

In the summer of 2006, shortly before our first conference (L&L in Albuquerque), Dell offered me a management position that would set me on a high-trajectory career path. It meant more money, more responsibility, more visibility, more . . . everything, I guess. It also included more scrutiny, more hours, and more travel, but at the time I thought all of that would be worth it to achieve my "goals". With some reservation, I accepted the job. And from the first day, I didn't like it; it just did not suit me, it was hard on my family, and I was struggling a bit.

A few weeks later we went to the conference, and I was beginning to rethink many things, including whether or not I wanted this new job. It many ways it was too late - I was in the job, my new team was relying on me, I had been promoted and given a raise. I didn't see a way to get out of it. But it was fundamentally at odds with my new world view, which was enhanced by unschooling. I was really struggling with making the transition from Corporate Executive to Unschooling Dad. More critically for my job, as time passed I was having an even harder time making the transition from Unschooling Dad to Corporate Executive. While we were at the conference, I raised some of these concerns at my first SSUDs meeting, and the general response was something like "You never should have accepted the job in the first place - get out." That made sense to me; I just didn't see how I could.

A month or two later I was with my new team in Texas, going through some team building exercises with a larger group. In one of the exercises, we were put in a scenario in which we were survivors of a plane crash. We had a list of 20 supplies that we had to put in rank order of their importance to our survival. The intent of the exercise is two-fold: it's designed to get the participants talking, evaluating options, and agreeing, but it's also designed to evaluate how well the leader (me, in this case) is managing to the "right" outcome. Now, I had done this exercise before, pre-unschooling, and had always used my leadership abilities to take charge and lead the team to the right answers, and we had always finished first - the quickest process, the best answers, all one team with one mission.

But this time, my own metamorphosis caused me to look at the exercise through an unschooling lens. I decided to take a less active role, and let the team come up with their own perspective, their own way to solve the problem - and their own answers. I made no attempt to change their mind, or influence their recommendations. I didn't disagree, or debate. What I did do was listen, support, answer questions when asked, and give my opinions. We took a long time to complete the exercise, and our answers were so far from "right" that we finished last. But you know what happened at the next break? We celebrated! We celebrated that we learned, and experienced, and shared, and listened. They actually thanked me for letting them experience the activity that way. It was an amazingly positive experience, and we all became much tighter after that.

Of course, the next day my boss told me how amazed he was at "my performance" - how amazingly bad it was, what a poor leader I had been, how disappointed he was that I had not taken charge and lead my team to victory. At one point, he said that if I wasn't going to focus on winning, then he would have to rethink his decision to put me in that job.

Talk about a defining moment. I could have fought him, explained that I was doing it to prove a point to my team that they needed a strong leader, told him I'd do better, something. What I wanted to do was tell him to go fuck himself while laughing demonically. What I actually did, though, is say this:

"I am at a point in my life where I have to decide if I am going to remake myself to fit a corporate culture, or change my company to fit my personality and passions. For now, I think you are right, with one small change: it's not that I am the wrong man for this job, it's that this is the wrong job for me. I do not care about winning, Dale - I care about playing. I care about learning, and growing, and trying, and living without fear, and doing what feels right, and listening to my heart, and coaching, and facilitating - but I could care less if I win, or if my team wins. I simply want them to value the experience of being. I have a different definition of what is important than you do. It's important to me that you are happy, and if you're not happy with me, I hope you do something about that."

Needless to say, I was removed from my position on the spot, but I was not fired. On the contrary, I was given projects that fed my passions - and I stayed at Dell until I found another company that valued the same things I do.

The idea of Winning, especially in business, is pervasive; businesses that do not focus on winning or trying to win do not stay around for very long, and that is bad for many people - customers, investors, and employees. But in many companies, somehow the need to win at all times and all costs has filtered down to every level of the organization. Almost everything in a company is measured in some way - yes or no, good or bad, on target or off target, in control or out of control. Employees are measured on if they win, not how they win - and only very rarely on how they play.

While this makes for profitable companies in the short term, I think it creates damage in the long term. As employees begin to be treated like numbers and rewarded only for winning, they become robotic and jaded, which eliminates the creativity and connection to the work so critical to real, lasting success. There is an underlying assumption that once you join the workforce, you do not need to continue to hone your ability to think, to expand, to learn, to experience, to fail - you are just supposed to perform.

I understand that, but it just doesn't really work for me. As a leader in my current company, I do all I can to create a different environment for everyone I come into contact with. I try to challenge people to to actually think about how they are achieving results, how they approach problems, to focus on the process instead of the outcome - in short, to think about playing, not winning. At the end of the day, companies have to win - it's the only way to provide for their customers and employees, which is why companies exist, I suppose. But their people are happier if they are treated with respect, allowed to fail and energized to learn. Real, true leaders recognize that, and create that kind of environment for their teams - and protect their teams when the company runs out of patience for learning.

At home, we have numerous opportunities to play, which means there are numerous opportunities to win and lose. My sons can certainly get competitive, no matter the game - street hockey, or Sorry, or a Wii game, or poker, or running - you name it. But there is a huge difference between being competitive and being maniacally focused on Winning. To us, competitive means practicing, trying your best, getting better; through the way that we interact with each other as a family, we've developed a spirit of trying, striving - but most of all enjoying. Some of this is because of the way we've modeled the sheer enjoyment of playing. But some of it also comes from the boys. Think about it - a kid can play the same video game over and over and over, "losing" each time but never stopping. They can play WoW for days on end, with no ultimate goal in mind. They can drag their bike up a hill 30 times on a hot day so they can have the sheer joy of riding down again. For the most part, they could care less about Winning; the very act of playing is fun in and of itself. They learn without trying to learn, just from showing up and experiencing things. They don't define the world through good and bad, win and lose; they just "do". Our role as a parent, often, is just to get the hell out of the way, put our own issues aside, and see the world through the eyes of our children - because although they do not try to teach us, we learn from them all the same.


  1. I really enjoyed this post Jeff. Thank you.

  2. Jeff, very well said. I've struggled with that since my first job out of college. Well before I was married or unschooling. Since getting involved in unschooling and truly indoctrinated by you and others at L&L this past fall I've really come to understand how my life has been lived that way for years. I dive into things and learn and then move on when I'm ready. I bleed with the spirit of an entrepreneur and live for the day I can make my own path and make my own living doing whatever it is that seems like fun at the time. The time is drawing nearer as we speak.

  3. Thank you. I love the "drag the bike up the hill 30 times on a hot day" analogy. I hadn't thought of it quite this way. The joy of riding down, over and over. Very nice, and it brings back GOOD memories. I can remember doing this and I remember the ride, I really can't remember all the hard work of getting back to the top of the hill. Interesting.

  4. Great post. I really liked the note you shared with your boss. Question, though: At that point in time, were you worried about the financial ramifications of saying what you felt? I think my husband feels a lot of the same things you do/did, but I also think he feels trapped, b/c by speaking up, he runs the very real chance (esp. in this economy) that they could say, nice, but you're on your own, buddy.


  5. Jenny, you raise a great point. The current state of the economy obviously makes it nearly impossible (not to mention potentially stupid and irresponsible) to flip off your job and walk out. In my case, though, I had to make a choice - I could stay in a job that made me miserable and affected every part of my life (except my bank account) in a negative way, risking my family and my mental and physical health. Or, I could trust that if I am happy and true to myself, and able to be the best parent and partner that I could be at all times, that it would all turn out okay. The worst case scenario for us was that I got fired, couldn't find another job, we lost the house, went bankrupt, and had to go on welfare and then move in with my parents. Really, if someone told me that I could have peace and happiness in exchange for financial ruin, I would take it. That's me; it's not everybody. More critically, I have a partner that is on board with that. The bottom line is that I had to trust that it would work out, and that the additional strength and perspective I got from going through that would make me a force to be reckoned with. Make sense?