If you’re hoping for any deep thoughts on the true meaning of freedom or that kind of thing, you’d probably like having a heads up that today we’re talking about something super frivolous: hair.
But, also maybe how hair can teach us about the true meaning of freedom. Or something.
Actually, maybe this post has more to do with freedom than any post I’ve ever written!
You decide.
But first, some back story.
Waaaaay back in our initial early retirement planning, Mark and I made a list of some of the things we wanted to do in our mythical, future next life.
And some of those things we’re already starting on! Some, not so much.
But notice what is in the very top position:
Being able to have weird hair felt like peak freedom to us. (“Freedom” in the small sense, not in the big sense, as this post illustrates.) In our careers as consultants to clients, we always had to convey a level of professionalism that goes beyond what a lot of jobs require, in that we had to – to put it crudely – look worth the money clients were spending. (No one ever said that to us, but you understand these things.)
So when my hair stylist in LA suggested several years ago that I try a “sexy mullet,” that was an immediate hard pass, for a bunch of reasons. (Let’s be honest.) Anything beyond a few highlights was not on the table, and the idea of having total control over our hairstyles felt to Mark and me like an important symbol that our retirement would be real.
And then a few years passed, we pulled the plug and leave our careers, and a few months in, we’d still done nothing on the hair front. As of two days ago, we looked pretty much like our profile picture, except that my hair got a lot longer because I hadn’t paid to get it cut.
I’d thought about it plenty. But there was always some reason why it wasn’t yet the right time. “I’m talking at Google next month and should probably look respectable.” “FinCon is coming up, and I’m speaking at that, too.” Etc. Etc. Etc.
And then a marvelous thing happened: I screwed something up.
Here’s how that expensive mistake ended up being exactly the nudge I need to grab a hold of the freedom I’d always dreamed of.
As I suspect many of my frugal friends are, I’m an aficionado of drugstore hair color. Though I’ve stuck to tamer colors in recent years, I’ve made the rounds through every product, and did all the more daring stuff back in college and high school.
And I’d done some boxed color a few months ago, to go redder, and while that was fun, I wasn’t totally feeling that look and decided to change it again.
Well, turns out I should have done more homework, because instead of going lighter all over as I’d intended, I ended up keeping the red but lightening the two inches of roots at the top of my head. Because, as every stylist apparently knows, and which I didn’t know yesterday, red doesn’t budge.
I happened to have a hair cut scheduled for the next day, so I went in with my tail between my legs, asking for forgiveness and also help, not wanting my hair to grow out with red at the bottom, a dark blonde horizontal stripe and brunette (and gray) roots.
See. You can be smart at some things and dumb at others. This week I was dumb at hair.
My stylist Melissa and I talked about the options, and there weren’t any good ones unless I wanted to go reeeeeaaaallllllly dark, which I did not. I finally accepted that the answer was what I’d feared: bleach. It would be imperfect bleach, too, because if we lightened my roots more, then that would look even lighter than the other hair, and I’d still have the weird horizontal stripe problem. So it was to be bleach with roots and some color on top to camouflage it for a while.
I thought about it for a moment, took a breath and said, “Let’s do it.”
And that, friends, is how I ended up dropping a bunch of unplanned money at the salon, but also how I accidentally forced myself to do what I’d always wanted but was scared to do when it came down to it.
The rest of the day went something like this:
And now I look like this!
Fun fact: that pink is not real hair color, it’s color depositing shampoo that will wash out completely. We live in the future, y’all. That also means I’ll probably be purple next week.
The Moral of the Story (It’s Not Really About Hair)
I won’t keep this particular look forever, but I feel strangely thankful that the bandaid has now officially been ripped off, for good I hope. There’s no undoing bleached hair, and I’m now pot committed to doing the kinds of things I’d always planned to do with my hair.
And, of course, it’s making me think about everything else I’ve always dreamed of doing but am not actually taking action on, either because I’m letting other things get in the way, or because I’m just straight up scared. We like to put people in one column in the other and call them either brave or weak, not some of both, and while I may have been brave in leaving my career and embarking on a different kind of life, that doesn’t mean I’m equally brave in all things, or at least not right away.
But the hair change is inspiring me to be better. Not just for the sake of being better, but for me. For the dreams I’ve already put off long enough. After all, you can’t really go quietly through life when you have FREAKING BRIGHT PINK HAIR. ;-)
What Nudge Do You Need?
Most of us are putting something off that we could do today, often including those big dreams or the small dreams that carry lots of symbolic weight. What is that for you? What is the nudge you need? How could you give yourself that nudge? Let’s talk about it in the comments!
Psst! We’re off to Coachella (#Beychella!), so no post on Monday. Back at you next Wednesday, and I commit to responding to all outstanding comments by then!

