My dad, a brilliant man, once said that he didn’t know how to help me in a particular situation because it was the first time he had a child with this particular problem. I was, after all, the first 26-year-old  daughter he had. It’s one more way that the old adage “we learn something new every day” seems to ring true.

I now understand as I have never had to raise a 16-year-old. The only thing I can say for certain is that, well, he’s definitely not the same little boy he was 10 years ago. Back then, my decisions were red Power Ranger sheets or blue, the big class with the good teacher or the smaller class with the bad teacher, broccoli because it is good for him or corn because he liked it.

The decisions today don’t seem to be as easy. Now I have to learn to let him go, let him grow on his own, trust him to start making decisions without undue influence. Some of those decisions include the tremendous technological growing pains the world has faced in recent years. His first email account, his first cell phone with texting capabilities, his first Facebook page and so on.

There was some fun – the very thought of letting my kid loose on the internet in a public forum.  Facebook has rules prohibiting children under the age of 13 having their own pages and at thirteen my son was, well, let’s just say not ready for Facebook… nor was Facebook ready for him.

At 16 though, I finally relented. For this birthday, I had created an account for him, invited friends for him, and hoped for the best, though in all honesty, I was not completely altruistic with my  “pre-friending” choices.

In the real world, I’ve worked hard to create a support system for my family. My children are aware of the adopted family members who have stepped forward without a second thought in times of need, when actual relatives have been unable to do so. We have had extensive conversations about good friend choices versus bad, and each of my children has told the other when a bad friend choice has been made.

Whether you believe in the whole ‘it takes a village’ line of thinking, for a single parent, at the very least, having extra support that cares, is a definite plus. At the top of my head I can count a Godfather, two adopted aunts, a faux cousin and two life-forged sisters who have stood beside me over the years. Having known that kind of support, it is fortifying to know that my kids also have the same.

I was my son’s friend on Facebook for the first few months but have quietly unfriended him, counting on those others I’ve trusted to be there for him, to continue to do so even online, all while letting him have his fun without his ‘mom’ watching.  I won’t lie, as bad habits go, one of the hardest to break is being a hovering parent. While some may frown on it, I also spot check text messages, randomly view emails, and consider it the modern day version of letting him play in the backyard. We never let them play for hours at a time without checking in on them, and he’s 16 not 26, therefore it is still my job.

Not as easy as Facebook will be the next big hurdle in raising a teenager – driving.  Only the lack of a certified birth certificate kept him from getting his permit this week. Every hospital show, teenage driving instructional video, and my sixteen years perfecting my status as an overprotective parent have jaded me against letting him even consider this next milestone.

Yet, his texts have been polite, his emails appropriate, his Facebook… well… he’s a teenager on Facebook. That being said, I have to trust that I have raised a good man. I worry about him driving, just as I worried about his Facebook, and the first time he learned to ride a bike, and the first time he learned to walk and so on. You get where I’m going, don’t you?

It would seem that while I continue to learn something new every day, I also learn that no amount of hovering will stop my children from continuing to grow.

So help a single mother out; how does one learn to “let go”? Does it get easier as they get older or are the challenges bigger and scarier? What did you do with your own kids?

More from Wendy

All Alone And I LIKE It

Who’s Standing In Your Corner

Yes Son, I AM Coming To School With You, Part 2

Wendy Syler Woodward, 37, has been a single parent for 10 years, with two boys ages 11 and 16.  Originally from southern California, Wendy moved her family seven years ago to Phoenix where she manages a law firm for work, writes for fun, and is preparing to go back to college before the end of the year. Follow her on Twitter at @WendySyler.