By the time you read this post, I will be lounging on a beach by the Mediterranean, or toasting my younger daughter (who just chose the college she’ll attend) with a glass of sangria while watching a colorful sunset. For this holiday – as with every other time that I’ve traveled for more than a week by plane and train, I hauled out my trusty, 30-something backpack – a relic from my college years – to accompany me on the journey. My backpack always reminds me of the days when I was young and carefree when all I needed to think about was when the next train was departing; more recently, it brings back memories of the last, joyful family vacation overseas when we were a family of four instead of three.

When I first began traveling after college, I’d always see hundreds of other backpack-laden young people like myself in train stations and at popular tourist destinations. Three years ago, when I was overseas, at least half of the backpacks had been replaced by wheeled-suitcases – and on this journey, I’ve spotted only two other travelers with their belongings on their back. Moreover, I’m not sure whether advancing age has caused me to be overly cautious and pack more, or just diminished my strength, but it’s no longer as effortless as it once was for me to toss on my backpack and trot off. In fact, once or twice, I succumbed to allowing a porter or cabdriver to lift up my pack so that I can slip into the straps. And so I’ve come to the realization that after this trip, it’s probably time to retire the old backpack.

My experience with my backpack over the years got me thinking about why many lawyers – particularly those twenty years into practice or more – aren’t as keen on law technology as we’d expect. Sure, there are the lawyers who will always be luddites fearful of technology, and those who have one foot out the door anyway, and lack any interest in, or energy to upgrade their practice.

But there are also a good number of lawyers who back in the day were tech-savvy, and who were as cool as I was as a college-kid with my backpack thirty years ago. Many of these lawyers still use WordPerfect or server-based versions of TimeMatters or Abacus because they work alright, and because that’s what they’ve always done.  Yet my backpack made me realize that “how we’ve always done it” doesn’t always reflect a curmudgeonly, anti-change attitude. Sometimes – as is the case with me and my backpack – we hang on to the past because of nostalgia. So that Wordperfect program brings back memories of the first brief that you filed in your own practice without the help of a secretary; the TimeMatters practice management system reminds us of the first time you had enough cash to invest in your practice and even hire a consultant.

As I now know with my backpack, nostalgia isn’t enough of a reason to keep an obsolete tool around. In the time it takes me to struggle into my backpack and get myself buckled, my daughters are already scurrying off with their wheeled bags, ready to board the train. And while my backpack still hasn’t caused me any back pain, I suspect that somewhere in the not-so-far distant future, if I keep carrying a pack, I’ll be hobbling around with aches unable to keep up on tours or hikes.

The same is true for lawyers wedded to old technology – even if it’s purely for the sake of nostalgia. At some point, the love affair with tools that are now obsolete may compromise your ability to represent clients if a program breaks down right before deadline and you can’t find anyone who knows how to fix it. Or if you use a word processing program that’s not compatible with opposing counsel and clients, so you can’t easily edit documents. Or, you may ultimately lose the value of your investment in your firm, because you  can’t transfer or sell it because your files and client lists are tied up in obsolete technology that younger lawyers don’t know how to use .

So as I said before, after this trip I’m likely to retire my old backpack and replace her with a newer travel bag with sleek, speedy wheels. Of course, I’ll keep her around – maybe hanging on my wall, or in the corner of my bedroom as a reminder of the time when an unknown future, bright and full of promise beckoned – because it still does.

When will you do the same?