How to Take PTO Like a Boss

I spent some time thinking how I can improve my approach to PTO to avoid vacation guilt. So I jotted down some thoughts and tried to consciously apply them during my recent vacay at the beach. Let’s take a look at how it went…

It’s July. Summer is in full effect. Tomorrow is Freedom Day. Yay for summer living!

I have a much different perspective on time off now, both as a manager and a father of two boys. As a developer, my job was to take documented inputs and create desired outputs. As a manager, my goal is to take lots of chaos and hopefully generate…less chaos. Rarely is there no chaos. This makes me a bit apprehensive about leaving for extended times.

The goal, of course, is to grow in my career and take on more responsibility. But balance is important and I don’t want to sacrifice time off that I earned like so many Americans do. I spent some time thinking how I can improve my approach to PTO to avoid vacation guilt. So I jotted down some thoughts and tried to consciously apply them during my recent vacay at the beach. Let’s take a look at how it went…

Before I Left

  • Treat preparation like a deliverable

    As PTO nears, it’s easy to get lost trying to just simply accomplish the day-to-day tasks. They tend to pile up and I start to feel uncomfortable leaving things in unfinished states. But neglecting to clearly layout the plan would likely haunt me on my return.  I delegated where I could and made sure I checked off my full PTO Coverage checklist.

  • Create a PTO Coverage Document

    Building a document helps me think through the expectations for my team. This also helps me ride out into the sunset knowing that I have at least put it down in a format that my team can reference if they start to forget what I’ve said. My document covered escalation paths, milestones and who’s doing what as well as potential risks that may arise during my absence. I made sure to meet with the whole team to walk through this document to reinforce it further. And, to give credit where credit is due, I totally stole this idea from my counterpart on most of my projects.  🙂

  • Don’t forget to configure tools accordingly

    Anything that pulls you back into reality is disruptive during vacation. I canceled/declined all calendar meetings/events, turned off email and set clear direction/explanation in my Out of Office auto-message. Never hop on a meeting when you are out. Ever.  Trust me, people want you to be fully undisturbed during your break because they want you to recharge and they don’t want the same expectation to apply to them when they’re out.

While I Was Out

  • Make memories

    Family vacations can be…chaotic. I’m still a parent, apparently, so I have to parent when all I want to say is “I can’t parent anymore.” But…this time is equally precious. Work can dominate our lives and sap our energy when we do have that bit of family time. I knew the time would fly by, so I took as many mental snapshots as I could, remembering the way the sand felt beneath my toes and what made my kids laugh. The more I was actively in the moment, the slower time felt.

  • Meditate and disconnect

    I wanted to make sure I found some time for me and only me. I made sure to give my wife some time as well.  She’s amazing, by the way. Anyway, during this time, I tried to not think and rest my weary soul. I was lucky enough to have a little private back porch connected to our room, perfect for sipping on iced tea whilst successfully accomplishing nothing at all.

  • Dream about your future

    As I enjoyed time with the family and time for myself, I found myself capable of imagining the future. I try to walk each day to think ahead, but oftentimes there’s just too many other things bouncing around in my head that prevent me from really dreaming of the future. I remember my trip to Hawaii a few years ago. I left there feeling very confident about growing my family and nearly a year later, we introduced our second boy to the world.

    And I still have my childhood dreams.  I continue to pursue them and trips like these help reinvigorate those passions.

  • Capture in a journal

    As slow as I try to make it go, vacation is but a blip on the radar of time. It’s very easy to look at it as not enough time. So I wrote everything I could remember, both small observations and memorable events, in a journal (aka, Google Drive document). Re-reading it, I felt pretty accomplished in all we got to do. And this journal can spark those memories again later on when I need to think back, reliving some moments that pictures can’t quite do as well.

  • Prepare for your return

    The worst thing that can happen is feeling burnt out quickly after having a chance to recharge. Whenever I go to vacation, I try to tack on a mini-staycation at the end. I want to mentally shift gears from vacation-mode back to the day-to-day mode. This also allows me to knock off a few side projects that I’ve been stalling on as well. The day before I went back to work, I took an hour to scan through emails to get a feel for what could potentially be the hot item on my return.

On My Return

  • Be glad to be back

    You just got to have a vacation, ideally you should be appreciative and recharged. When you’re gone for a while, people notice and will likely ask, “how was your trip?” I didn’t want to say “not long enough” or “back to the grind”, I made a conscious effort to say a quick summary and cap it with “I’m glad to be back!” The truth is, I do love my job and I’m glad to do it, but just to make sure to squash any subconsciously lingering feelings of not readiness, stating this simple phrase helped me feel excited to take on the challenges already heading my way.

  • Catch up with coworkers

    While I knew there was undoubtedly chaos that I needed to assess, I wanted to make sure I spent time just talking with my coworkers about non-work related stuff. I often get stuck in professional mode that I forget to touch on the human side of my coworkers. I was pleasantly surprised at how much I enjoyed just chatting about trivial subjects with people I hadn’t seen in a couple weeks.

  • Work a normal day

    The worst thing you can do is take on too much upon your return. You want the “stress-free you” to remain as long as possible. There’s going to be a bit of a backlog to go through. It’s okay if it takes a few days to truly get caught up. I got in at a normal time and I left at a normal time and as I wrote this post, I still feel like my soul is in a good place and ready to handle the next few projects coming down the pipe.


Doing the above helped me appreciate my time off. It helped me maximize the effects of vacation without having me stress about maximizing the effects of my vacation. Maybe that sounds silly, but sometimes when life gives us lemons we try to make a Corporate Empire selling them. “Just do it” and “you only live once” are great tag lines, but I like to treat time off like “do and don’t do, both intended for you.” I should patent that. But whatever you do, make sure to take your hard-earned time off. If that comes back on you negatively in any way, it’s probably time to consider making a life change.

Happy 4th of July, readers! Let me know if you got any tips and/or tricks you do to make the most of your vacations/staycations in the comments section below!


Welcome to Mid-Career and Another Round of Imposter Syndrome

Mid-Career is a time frame that is a bit open to interpretation. It’s not like you wake up one day and say, “today is the day I start my Mid-Career.” And that’s exactly my point. You’ve become an experienced professional. There is no welcome, or if there was, it happened a while ago. You’re here, now what’s next?

You’re sitting in your vehicle, holding a warm cup of coffee in your favorite “#1 Dad” mug, staring at the office you go into every day.  And you think to yourself, “now…how did I get here again?”

It turns out, most of us work for a long time.  A really long time.  And we thought High School would never end.  Along the way, there’s a subtle, psychological evolution happening that may take a while before you realize.  We’re so focused on goals and life events ahead of us, we’ve lost sight of the trail we’ve blazed.  Pause for a second now and recount your post-school life.

Welcome to Mid-Career
It’s not quite the same thing as Middle Earth, but if that makes your life more intriguing to think of it that way, more power to ya!  Mid-Career is a time frame that is a bit open to interpretation.  It’s not like you wake up one day and say, “today is the day I start my Mid-Career.”  And that’s exactly my point.  You’ve become an experienced professional.  There is no welcome, or if there was, it happened a while ago.  You’re here, now what’s next?

You’re going to be here a long time.  Some will say, “if you’re bored, why not change it up?”  And those who get comfortable, often have the rug pulled out from underneath them.  Brace yourself, Life is coming.

Another Round of Imposter Syndrome
There are plenty of good articles about dealing with Imposter Syndrome.  There’s not much I can add to them.  What I did notice was that most of them don’t address the fact that you can deal with it multiple times over the course of a career.  Maybe it’s something you are constantly battling?

Thus far, of all the articles I’ve written this year, I’ve struggled with this one the most.  I’ve rewritten and modified it to go many different directions.  It was like I was experiencing a mini-bout of Imposter Syndrome as I wrote, feeling like my inability to string cohesive words together to make any kind of point would in fact prove that I shouldn’t be writing in the first place.  And this is what made me decide that, more than ever, I need to get this one out of my system.

I made a pivot a few years back when I decided not to pursue coding any further, taking on the role of a Technical Program Manager instead.  I dealt with the ghosts who shamed me, saying I clearly wasn’t good enough to be a top notch developer.  Then, came the ghosts who said I had no right in this new position because I had no training in management.  And, when I earned the senior moniker, these ghosts continued, “and exactly how are you any different than before?”

I seem to be going through a tug-of-war between confidence and doubt.  Considering I’m 10+ years into my professional career, I imagine that battle is no where near complete.

The Pursuit of Happiness
What a bleak article, eh?  But there are some simplified takeaways:

  • For most of us, our work/career spans the majority of our life.
  • Along the way, risks arise and can become issues.
  • Mentally, you can easily fall into a trap.

These are things to be aware of, whether you are early in your career, struggling though challenges now or dealing with the repercussions of a series of unfortunate events.  You might be simply going through the motions, unaware of how deep you might be in a rut.  The simplest question, and one to ask yourself often (pro-tip:  setup a regularly recurring reminder):  are you happy?

For me, the answer is Yes!, but I’m not satisfied.  I enjoy my role now and have found this blog to be a welcomed creative outlet that helps me tweak and tune how I approach my career and life.  In fact, I’m more motivated than ever to keep learning new things and perfecting other things.  This hunger propels me forward.  I do make mistakes (often!) and others might be judging me, but there’s too much I want to do to let that slow me down.  Bring it on, Life.

So…are you happy?  If not, ask yourself Why?  Take time in answering that.  Then start making a game plan.  It’s never too late to start pursuing happiness.