The Conundrum of Flextime

I found this to be an interesting read – Steve Whitehill

A lot has been written about different ways to manage employees and their time at work—probably too much.

But managers will always consume that writing, because managing other human beings will never cease to be one of the most difficult professional undertakings a person can take on.

If you’ve ever managed a team, you’re probably familiar with some of the rhetoric surrounding people management. To quote Peter Drucker:

“Management is doing things right; leadership is doing the right things.” 

Product-oriented versus process-oriented approaches. I could write circles around that alone, but I’ll spare you.

On the other hand, entrepreneur Paul Hawken had this to say—a bit reminiscent of a parent cleverly gamifying the weekly chores:

“Good management is the art of making problems so interesting and their solutions so constructive that everyone wants to get to work and deal with them.” 

Obviously, different jobs require different methods of management—from traditional “clocking in” to the new-economy freedom worker who can work whenever, however, and wherever they want. We have WiFi and laptops to thank for the workflow revolution that our parents and grandparents never could have imagined in their wildest dreams. But of course, nothing is ever as simple as it seems.

This brings up one central question for me: What if you’re the boss?

Shouldn’t the boss be able to benefit from the flexibility that modern technology affords to the business world, working and taking off whenever they want? At its core, isn’t that the whole point of being the boss—the freedom that accompanies the undertaking of working for oneself? Only, it’s not that cut and dried.

The problem for most of us—and I’m speaking for most of my entrepreneur clients, for that matter—boils down to one persistent problem:

Working whenever you wants slowly turns into working all the time.

While I try to be better about being available during “traditional” work hours to attend school events or other family/personal occasions, my Jewish guilt (yes, that is very much a real thing) inevitably builds up and prevents me from ever really leaving the office, no matter where I am. In my head, I can’t help but think, “I should be working right now.” Could, becomes should, becomes must.

It doesn’t matter how much I’ve already worked that day or how much is left on my plate for the remainder of the week. I don’t clock in and out, and nobody tracks my hours—my own productivity is all on me and only me. And while I may have been up since 4 AM that morning plugging away at my dining room table (my doctor wife has taken our home office), I still feel that inescapable pull to get back to firing off emails or returning phone calls as soon as I possibly can. The entrepreneurial gravitational force at work.

I am actively trying to be better, taking time out and being present outside of work. I know unequivocally that I am a better leader and manager when I’m able to truly step away at the end of the day—not to mention a better dad and husband.

But while it has come naturally to me to manage my other team members in this manner, focusing on the results and what’s gotten done versus the hours worked, it’s more complicated when it comes to my own time. I can always do more. And it muddles things that there’s always more to be done.

As many of you know, I feel like this is my second shot at true entrepreneurialism, and I want to do better this time around. I want to get it right. I have tried to take advantage of the supposed “freedom” that comes with working for oneself, doing things like going for a run at 9 AM on a Tuesday morning. But last week, I took an actual leap:

I snuck out for two whole days, during the week, to go climbing in Colorado.

And guess what? To my shock, the world did not fall apart. My company did not crumble. In fact, we had a great week and did a record number of fundings. Talk about a pleasant surprise.

And just like that, I am quickly learning that as much as my ego may want to disagree with me on this, I am not that important, at least when it comes to day-to-day operation. I can trust my team—they’re my team for a reason. On top of that, I also discovered that I was significantly more productive in the few days leading up to my hooky days—and I enjoyed them more. Never underestimate the value of having something to look forward to, especially when it feels like it has to be earned.

So, all of this to say, I’ve made a decision for how I’m going to operate differently moving forward: Simply put, I’m going to keep doing it—stepping away, reserving time for the other parts of my life that have nothing to do with numbers or spreadsheets or conference calls. I’m also going to actively encourage my clients and my team members to do the same for themselves.

Now here’s my challenge for you: Pick a couple days within the next few weeks coming up, get some extra work done beforehand (or not), and reward yourself for being a business owner or valuable team member.

Whether you believe it or not as you’re reading this right now, you can spare it, you deserve it, and you and your team will be better for it.

Let me know how it goes.