Managing Your Time When You Have Too Many Things You Want To Do

2,423 Words. Plan about 11 minute(s) to read this.

A friend of mine asked me the following.

“How did you manage your time and schedule for 5 years with everything you wanted and needed to do?”

Here’s the context for that question. For about 5 years, I had a full-time job as a global network engineer for an e-learning company. Later, I transitioned to a similar role for a medical startup, again full-time. At the same time I was employed in those roles, I was blogging and podcasting as the Packet Pushers community grew.

As Packet Pushers ramped up, it turned into a second full-time job, a state I maintained until I was able to transition to working for myself exclusively.

Managing time and schedule.

Let’s get into the meat. How did I manage my schedule with ever so much to do?

First off, I had understanding employers that let me blog and podcast during traditional work hours, as long as it did not interfere with my regular work duties. I was always upfront about this. I never snuck off during the day to work on my side business. My boss always knew exactly what was up.

This translated roughly to flexible hours. There was also the understanding that I was always going to be available to jump in and get things handled that were time-sensitive, or react to a system-down event requiring my particular set of skills.

Focus. I would (and do) set my mind on one task at a time and see that through to completion, then work on the next thing with as little interruption as possible during each task.

That’s a bit idealistic, of course. For example, I tended to react to instant messages and HipChat quickly because people generally needed me right that moment if they were pinging me. On the other hand, I ignored e-mail for 24 or more hours. Urgent messages rarely came through e-mail. This strategy reduced interruptions, and allowed me to be highly productive when I stuck to the strategy.

This issue of focus and productivity is still true today, and I still struggle with it mightily. Inbox and Twitter are my primary distractions and can cause me to be busy without accomplishing the important things on my task list. I use a Mac app called Anti-Social to help break the habit of checking social media when the temptation to distract myself is too great.

My wife has always been supportive of my projects going all the way back to my very earliest Novell and Microsoft certs back in the 90s. I also do my best to keep up with her. She knows more about IT companies and industry acronyms than she should really be burdened with, because I try to make sure she understands what’s weighing down my mind–why I’m stressed or happy or sad or elated or tired.

I also try to prioritize spending time together that’s unfettered by all the stuff I have to do. More on spouses later, as it’s a critical topic for ambitious, career-minded people in IT. But in summary, I get to put on my schedule what I put on it when she’s supportive of those things.

I had a goal in mind. Initially, the goal was a bit of extra cash, as we always seemed to need a bit more. I’ve almost always had a second job consulting, running a small SaaS operation out of my basement before it was called SaaS, and later on writing articles and reports for media publications or public speaking at conferences. Those things all happened because of some skill I had acquired previously that I could later turn into extra dollars.

When the podcast took off, and Greg and I figured out that there was money there, the goal shifted from “extra cash” to “doing it full time.” We both wanted a break after 20+ years in the corporate world, and so we worked on our personal finances to get to a point of having de-risked working on Packet Pushers full-time.

Therefore, on those days where the day job just ended after a stressful 12 hours of planning for a major data center cutover, I’d still find a little motivation to work on Packet Pushers. To blog something. To reach out to a guest about show scheduling. To write a script. To edit a show.

The goal was to get to having one full-time job instead of two, and get some of my life back. That helped prioritize the calendar.

I worked from home as much as possible. Commuting ate 2+ hours a day, as I live in central NH where it’s relatively cheap, but over my career tended to work in towns on the Massachusetts border where there were a lot more tech jobs for someone like me.

I ended up phasing in WFH about 4 days a week at the e-learning company with support from my boss. Then when I worked for the medical startup, I worked from home all the time, since they were located in Columbus, Ohio. I traveled to Columbus once a quarter or so, but generally lived in HipChat to communicate with the team. Lots of video discussions. This worked well.

Of course, this also won me back some time in the day. I used that time to be more productive than burning fuel up and down the highway just to get to a cubicle.

On the other hand, some days you don’t get it all done, and that’s okay. There is too much to do, and not enough time to complete everything.

Even with focus, organization, and planning, things don’t always go the way you want. You don’t get to write that post. You have to re-schedule that podcast recording. Or maybe the day job just really, really needs you to get them over some hump, or dig deeply into packet captures to help narrow down why the SIP transaction is acting so oddly.

In that case, on those days, it’s all about priorities. Know what they are, stick to them, and recognize that sometimes the lower priorities are going to be the ones that get neglected.

The hierarchy of priorities.

For me, I have always made decisions, or at least tried to make decisions, based on the following hierarchy of priorities.

Family, my wife especially. If she wasn’t 100% on board without reservation deep down inside, I would be very unlikely to take on whatever it was. I value her and our relationship above all else in my life. I realize it’s different for different couples, but the way I see it, if that relationship is compromised, the rest of my life is at risk. I view my marriage as the foundation upon which whatever personal accomplishments I can look back on were built. If you’ve followed my writing over the years, this is not a new idea you’ve heard from me.

I also made consideration for my kids. My commitment was, simply, to be around. To be predictable. To be a steady influence in their lives they could count on. To be approachable and reachable, which for a lot of pre-mobile phone and FaceTime years, meant being physically around. For this reason when they were younger, I turned down jobs where I would have been expected to travel a lot.

All of this to say that there are more important things in life than career objectives, at least for me. Even so, I know MANY people who are divorced, separated, or otherwise unhappy in their relationships because they gave everything to their IT career, leaving nothing for their family. It’s a choice we all have to make, and it’s hard to get completely right even when trying to.

Who’s paying me. If I’m getting paid by $dayjob, then clearly $dayjob demands my loyalty. Not $sidejob. I’ve given $dayjob an implied promise that they give me money, and in exchange, I give them a reasonable amount of work, for some definition of reasonable. Given a choice between making sure $dayjob is happy vs. $sidejob, $dayjob would win every time.

Cheating $dayjob to work on $sidejob isn’t ethical. See my first point about employers who are understanding and being upfront with them. This means that sometimes, you just don’t have the time to work on the things you want to work on. You have to keep up with your commitments, honoring where the money is coming from.

What do I have time left to do that’s important to me? When prioritizing $dayjob, that got first cut at my calendar, along with the ability to preempt any sort of $sidejob events I had scheduled. When there was time leftover, I would fill in with blogging, podcasting, and so on. Most weeks, there was enough time.

As a side note, I’ve struggled off and on with scheduling every hour of the day or not. At this time, I don’t schedule every hour. I find my workflow doesn’t map well to every hour being blocked in that manner. However, if I find that I have a 4 or 6 hour block that’s unscheduled, I might reserve it for myself. This gives me a block of contiguous time to make something–a blog post, a podcast, a book chapter, a presentation, etc. From there, the trick goes back to focus.

Personal time. I have found, especially as I’m getting older, that I need downtime. For me, that’s a mix of gaming, anime, movies, dramas, music, exercise, and backpacking in the mountains.

Needing downtime perhaps sounds like laziness or a cop-out, at least it does to me when I ponder it. However, I’ve learned the hard way that it’s not laziness at all. Rather, I have to have regular, even frequent, times where I am completely disconnected from responsibilities, or I’ll have minor breakdowns.

I recall a few times where I’ve had so many things to do that my brain sort of locked up–that’s the best way I can think to describe it. My hands were hovering above the keyboard and trackpad, shaking. I didn’t know what to do next. I couldn’t prioritize. I couldn’t handle all the inputs fed to me by my screens competing with my task list and the pressure of deadlines.

That’s a very odd feeling to be locked up and shaking like that, especially if you’re a person who is typically in complete control and has all the answers. Those locked up experiences have been wake-up moments for me, where I realized that I was broken inside, that I was the one who broke me, and that some changes needed to be made.

In retrospect, I should have moved “personal time” higher in the hierarchy. For many years, I prioritized myself last, and I believe that was a mistake. Counterintuitively, I think that, had I allowed myself a bit more personal time, that I might have actually gotten MORE things accomplished. At least, that’s my current experience as I limit the number of hours I work each day, spending them highly focused, but then leaving the workspace after those hours are through.

Saying no is your superpower.

Which leads me to my last point. When you are a very busy person trying to do very many things, you have to learn when to say no. The more “many things” you do, the more opportunities that will come your way. It’s a snowball-to-avalanche effect, and you can’t outrun the avalanche.

At $dayjob, you raise your hand to lead some project. The project is successful. Now you’re in charge of the end product forever, so that gets added to what you do. The business remembers how extraordinary you were at that project, and asks you to head up the next project with brand new, big spending, Super Important Customer, and somehow that’s a thing you own. And of course, you’ve been contributing to the wiki at work, and Sue, who you’ve never met but works in the Toronto office, read an entry you wrote, and wonders if you could spend a couple of hours explaining a few things.

In $sidejob, you got a good reaction to the article you submitted to Major Tech Publication, and now the editor wants you to maybe do a longer write up for this report they are publishing in a couple of months, and would you like to take that on because the money’s not bad and you wouldn’t have to do much research? And then a vendor notices that you’re an influencer, and wonders if you’d like to attend their conference, all expenses paid to lovely Las Vegas or San Francisco? And then a book publisher gets wind that you’re a strong technical writer, and wonders if you’d like to be the author of a book they’d like to publish?

And on and on it goes. The more you do, the opportunities you have. If you aim to please, it’s hard to say no. If you’re greedy for attention, it’s hard to say no. If you can use the money, it’s hard to say no. The temptation is to say yes to everything, and so you do.

Because you say yes to everything in both $dayjob and $sidejob, you overcommit yourself to the point of frantic activity, trying to stay ahead of the avalanche behind you. You think you have balance, and that you have everything under control. You’ll write in the air over flyover country. You’ll work on the weekends. You’ll do a few sprints to knock out some of the projects. You’ll hold meetings while waiting to board the plane. You’ll take advantage of the time zone differential while you travel. You’ll skip breakfast today, and maybe lunch.

You’ll go insane. That’s what you’ll do.

Knowing what to say no to is your superpower, and the only way that you’ll get done the things that are truly important to you. Saying yes is very often filling your schedule with things that are important to other people, and NOT things that are important to YOU.

Every opportunity must be accepted or rejected in light of your goals and priorities. How does this opportunity meet them? If it doesn’t, politely declining is not only wise, it’s utterly necessary. Otherwise, the avalanche runs you down.

Beyond that, saying no is the only way that you’ll have enough holes in your schedule for personal time–that recuperative time that you need to stay fresh, creative, and able to focus when it’s time to work.

You are the most important part of this entire equation–the thing that must be preserved. Don’t lose sight of that. Martyrdom is not a winning strategy.



Ethan Banks writes & podcasts about IT, new media, and personal tech.
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