Communication Work

The Babysitter Club (How To Be A Responsible Adult)

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Dear Children,

You’ll never believe this, but recently, I had an idea (okay, I had four hundred ideas, but here’s one):

The Babysitter Club.

It’s an E-course on how grown-ass men and women — particularly contractors, clients, and rock stars — can finally learn how to be as responsible as one might (wrongly) assume they would be after all of the years accumulated between the birth canal and their fully-adult selves.

It includes such hit lessons as:

  • Step One: Set an Alarm
  • Step Two: Wake Up
  • Step Three: At Least Try to Pretend That You Have a Job to Do
  • Step Four: At Least Try to Pretend That You Know How to Use a Calendar
  • Step Five: Clock Yourself In
  • Step Six: Open Your Email

Okay, so I didn’t actually create The Babysitter Club, and sure, it’s a facetious list. But like an acquaintance of mine, Propaganda, says…

“Sarcasm is really the only time people tell the truth.”

I’ve written about coaching quite a few times during this season so far — whether it was my pursuit of an official (and eventually, forfeit) certification at a firm for My One Thing or the announcement that I’d be moving into more of an “executive coach’s” role at XXXchurch. The reality, though, is that I’ve been coaching people, albeit unofficially, for years now.

As a dad, one of the best roles I’ve ever played was as a coach for my kids’ soccer leagues. Throughout ten consecutive seasons, I coached teams that both of my children were on (and even led three of them as undefeated, thank you very much). I’m the guy who printed “Undefeated Champion” T-shirts before we played our final game. Some people find that abrasive. I say it’s confidence.

(In reality, I admit, it’s probably both. Nevertheless, I mean… we did make the win, so…)

As a professional, though, the majority of my coaching has developed naturally out of the relationships I’ve built with subcontractors who have helped me and my teams bring our goals to life, and particularly with artists.

I won’t lie: I have a love/hate relationship with most creatives (and, to be fair, given the fact that most people who create don’t like to be called “creatives,” I’m sure the sentiment goes both ways).

Most of the time, it’s like pulling teeth to get an artist’s work delivered on time. But it’s not just the artist — it’s the work-for-yourself crowd. It’s the I’ll get to it when I get to it mentality. The “fluid workspace” which is much less a nontraditional parameter for most people than it is a complete lack of any boundaries, whatsoever.

Many of the creatives (humor the noun) who have done or are doing consistent work for me, though, enjoy having me as a client. I finally realized why, and it circles around to the same epiphanous realization I keep coming back to: I’m also their coach. They like working with me because I push them, drive them, remind them, keep them on task and — often — deal with the day-to-day logistics that they hate (but need).

That’s all well and good — and I am a more natural-born leader who isn’t as bogged down by logistics — but often (and all of my guys know this, so don’t damn me as passive-aggressive), it can be exhausting.

Babysitting is a tiresome chore, and I’m continually trying to figure out how to impart some of my strengths as a self-starter to others who have very little of that trait as intrinsic to their own personality. Simultaneously — lest one assume that I view myself as only and ever the teacher — I’ve learned much about the benefits that patience brings to a final product.

Nevertheless, deadlines are deadlines, so whether they’re past due or agreeably stretched, the main question I have is:

How do you work for yourself?

A layer beneath: How do you do deep work for yourself?

It’s not like I haven’t had to answer the same question. Ever since I sold baseball cards as a fourteen-year-old, each of my jobs has been an entrepreneurial endeavor. I value working for myself, as do most of my clients, but self-employment necessitates a certain level of discipline that must often be built — like one might build a muscle — if it is to be a strong enough foundation to hold up a life.

And when I say “hold up a life,” I really do mean a life — not just a paycheck. Many a self-employed person deposits substantial numbers but does very little beyond the work it takes to accumulate them.

We’ve got to think lifestyle over revenue. I learned that lesson from a wealthy man who is richer in relationships than his bank statements will ever account for, and I agree with him.

We all traded our parents’ Nine-to-Five for what we thought was freedom, but in reality: half of us are working 24/7 with no boundaries or breaks, and the other half feels like they’re working just as much — always “on” and mentally exhausted — without ever accomplishing anything for lack of personal boundaries or working systems.

Without parameters, everything bleeds into the next, until all things become no things.

Without boundaries, you might be there, but everyone knows you’re not present.

Without figuring out how to get your work under control, your work will always control you.

I’ve spent a lot of years talking about how difficult it is to rewire neural pathways in the brain. When it comes to addiction, change is as difficult in work as it is in porn as it is in eating habits as it is in whatever other rut you might’ve been digging for the past however-many years.

If I’m not intentional about creating a schedule, locking it into a calendar and then sticking to it, what should have been an eight-hour workday will double to sixteen before I’ve even realized it happened. I can almost guarantee you, though: it will not have equated to another full day’s worth of accomplishments. Instead, it will become a frenzied and anxiety-inducing afternoon/evening, full of short-tempered impatience toward myself and my family, before I have to do it all over again.

Maybe you know what I’m talking about.

I’ve had to get extremely practical when it comes to creating a schedule, and I’ve had to ask for help. Recently, I hired a personal assistant. I gave my wife control of my calendar, and then I started using Calendly to schedule meetings where time slots remained available so that — instead of arbitrary work meetings interrupting family dinner — I can both plan for their start and look forward to their end.

I’ll say this, as well: many a self-employed person experiences compounding misery atop his or her already-unkempt calendar due to the vague-yet-constant feelings of urgency that our world’s unrelenting interconnectedness impresses (or, oppresses) upon them.

Here, too, putting in the work to develop a working schedule is helpful. If you’ve already allotted time — an hour, perhaps — for catching up on whatever you might miss throughout the day, then you don’t need to worry about following every tangential beep and notification tempting to pull you away from work at hand. Chances are, you’re not missing anything. But if, in fact, you are, then you can come back to it, and schedule it in when you’ve got the time to focus on only that thing, rather than succumbing to the overwhelming lie that all things must be happening all at once.

Also, to reiterate a favorite and familiar lesson: turn your damn phone off. Silence your notifications. Do Not Disturb is your best friend. It’s no wonder we’re all so scatterbrained, and so late on our deliverables, while incessantly bombarded with distraction. A few years ago, a study on “digital distraction” came out of UC Irvine, concluding that it takes a person about twenty-five minutes, on average, to return to her original task after having attention diverted by some dinging device.

Finally — and especially because so many of the people I work with and I want to grow and scale our endeavors — there is a massive difference between working in something and working on something.

In the beginning, especially, almost everyone has to spend time in the weeds. Eventually, though, we need an overhead view to get a clear perspective of all that we’ve been tangled up in. At some point, it might be time to delegate tasks that would have otherwise swallowed up your time to continue developing your vision.

My question for you — grown-ass-adult that you are — is: whether or not you’ve got a job that affords you the privilege of choosing your employer… are you capable of being a reliable employee?

Can you hit a deadline (without having to be chased down)?

Can you be counted upon to reach a goal?

Are you disciplined enough to create your own?

Do you need some sort of junior-level assistant who might be able to take on the grunt work that’s bogging you down so that you can scale your business?

Do you need to give your wife your calendar?

Do you need to bust out a dictionary and check out what a calendar is?

It is possible to be a responsible adult. To set an alarm and get out of bed before you’ve hit snooze for a full hour.

I joke about The Babysitter Club for “contractors, clients, and rock stars” because they’re/we’re often the ones who know the least about creating healthy rhythms in and from which to function. Frankly, no matter how put together or enviable those folks might look on Instagram, they’re often the most disorganized and least satisfied with the chaos of life, yet with little to no clue about how to change their circumstance, or get out of the ruts that have become Grand Canyons.

Levi likes to tease and call me “dad.” Well, son, let me run with that analogy (since I’ve spent plenty of time babysitting you, too)…

It might’ve been easy to piss into your diapers for so many years, but it was also uncomfortable, and unless someone helped you out, or you pulled them off, yourself, you’d have just walked around in your own private urine pool all day long.

Potty training sucks, but once you learn how to aim, you’re free from what used to be a trap of your own making.

Taking responsibility is kind of like that. You’re happier, and I’m done changing diapers.

  • Step One: Set an Alarm
  • Step Two: Wake Up
  • Step Three: At Least Try to Pretend That You Have a Job to Do
  • Step Four: At Least Try to Pretend That You Know How to Use a Calendar
  • Step Five: Clock Yourself In
  • Step Six: Open Your Email

And don’t forget to clock out. Your mind needs it, and so does your family (and so — for that matter — does whoever you call “boss” for the sake of the fresh, creative mind he hired you for).

It’ll take some work to work better, but dammit ya little baby, it’s possible and worth it.

With Love,
A Grown Up

P.S. David Allen has a pretty amazing book on productivity, task, and work-life management called Getting Things Done. In reality, it’s more a methodology than anything else. Its subtitle is, “The Art of Stress-Free Productivity,” and he provides pragmatic offerings for how one might go about organizing not just a day, but a brain, into orderly and actionable steps so that you can uh…get things done.

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  • Melissa Rodgers Williams

    Great stuff that all we ‘work from homers’ can identify with, I’m sure. Of course, I was pulled to this article by a ding on my phone, but for once, the interruption was worthy of my attention. Now I’m going to use that do not disturb feature and increase my productivity by 200% at least.