Life is funny like that.
I went from a hot pool and frozen alcoholic mango drinks in the Poconos, to seeing “a plan come together” (twice), to almost losing my DuoLingo streak (btw my Spanish is still terrible), to spending yet another quarter day delayed in an airport (America, please — get it together!), to a harsh snap back to reality at Saturday morning before sunrise.
I guess that’s what I should expect, my life is a human story after all. I often wonder, though, how this particular iteration of my personal the Monte Carlo simulation all ends.
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If you’re still? working in the world of Tech then those “day in the life” vlogs of a Software Engineer where you stroll in at 10 am, go to the gym, grab a free lunch, have a meeting, grab a coffee, code for an hour and go out for drinks with the team are truly over. To be clear, they were never my reality but for many of those that were it’s quite likely they’re now looking for a job.
Photo by Julia Joppien on Unsplash
…monday
After what seemed like a short weekend filled with pools, arcade claw machines, and insatiable kids (it was 11pm I couldn’t catch a Labubu or Princess Peach if I wanted to!), I woke up at 3am on Monday to take a weary early morning trip to the airport. Frankly before that I barely slept — anxiety and insomnia almost always hit whenever I have to leave early or be away from loved ones.
Anyway, the plan for this week was simple: fly to Chicago, connect with the team, onboard a new hire, continue the transformation of my teams from waterfall to agile, present progress to leadership, fly back home, and wrap up the week with a bug-free release, some retrospectives and perhaps an interview.
The reality was always going to be challenging. Leadership is by definition not for everyone; it’s not all coffee and sharp suits or tech hoodies & cool sneakers.
Leadership: the ability to influence and guide a group of people toward a common goal by providing direction, motivating team members, and fostering collaboration
Day to day I lead leaders (software development managers) and motivate and collaborate with individual contributors, product owners, support and infrastructure engineers, sales teams, client services groups, and other leaders.
Who motivates me? That needs to come from within—sleep, energy, or mood be damned—forget your mood, stick to the plan! There were no cheerleaders waiting for me at the airport just a neo soul soundtrack playing on my noise cancelling Sony headphones which I’ve found of late centers and grounds me in a way that the 140–170bpm music I used to code to never did. After all, it’s not just focus I need this week—it’s clarity and calm.
In this role I’m not just invited to the party but I’m encouraged to dance, refreshing to be seen as an equal—it’s not always been this way.
Arriving in an Uber just in time to see one of my team shine in a group setting was a great way to start the week. Individuals that just need good soil, a bit of water and for you to just shine a light and they take care of the rest are a pleasure to coach.
I took our new recruit out to lunch with the team, kicked-off a 30/60/90 day onboarding plan, had a one-on-one with the boss, started prepping for our date with leadership.
The night ended after I checked in with a door-dashed meal at the hotel and falling to sleep during my FaceTime home.
…tuesday
I was up by 4am on Tuesday, we may have “fallen back” on the East Coast on the weekend but I was living in a different timezone and unfortunately no-one had informed my body clock; so would continue my sleep debt.
I was at work bright and early around 7am with one or two of the usual suspects in the office just before me. It was a good opportunity to finally try the coffee shop downstairs so I grabbed an iced coffee with oat milk (because: lactose) and a croissant. I’d asked for an almond croissant but it turned out they only had pistachio—I wasn’t disappointed, in fact — it was damn good. Pistachio was about to become the theme of the week.
Anyway, between a one-on-one with our new recruit, dropping in on some scrum calls—context is King in my role (execution is the currency — you need to be able to impact execution meaningfully), a surprise “ask me anything” — where I would I would be put on the spot by one of my own engineers (where’s the loyalty?), a few agile sprint planning calls, an operational review with our client services and infra partners and a hiring standup, it was a fairly busy but effectively what I would call “light work”.
I had a ton of one-on-ones in the calendar this week but I had a feeling that sticking to the plan would be impossible; I had to kick a few to Wednesday — it’s always a little unfortunate to have to do that when you’re trying to get face time with individuals to influence, guide, and encourage but also a few high stakes meetings on the calendar.
I’m realizing at this point I’m going to have to reduce how regularly I’ll be able to connect with individuals if I’m going to be more effective driving horizontals like hiring, productivity, and generative AI adoption across the wider group.
The evening ended with dinner with a few in the leadership team—Mediterranean food (another theme for the week), red wine, and pastries with (you guessed it?) pistachios.
I got to the hotel that night not tipsy but enthused—working with people who are both excellent at what they do but also care deeply about team culture, respect, excellence, and finding personal and common ground and what it takes to scale and grow an organization fills the cup.
I am left motivated.
FaceTime — my son has a new stop motion animation he’s posted to YouTube and it’s pretty cool. He took my advice to make it a little bit longer.
Sleep.
…wednesday
A drink or two the night before means I sleep a little longer but honestly not by much. The darkness I get in the hotel means I tend to sleep generally well enough but not for long. I’m at the office by around 745am but not before I’ve gone via Starbucks to get myself a trademark Iced Brown Sugar Oatmilk Espresso. (Who needs to self-motivate when you can infuse yourself with sugar and caffeine?)
I chose a hotel this week was just far enough that I’d be able to take a little walk but not too much, after all it’s Fall in Chicago. On the way into the office — I took a look at the calendar: no less than seven one-on-ones, three stand-ups, and a leadership meeting prep call that turned out to be very much like a deposition from Suits—it turns out that it’s not enough to just make statements — every vector and every scalar needs to be backed by supporting data and you need to be able to speak to that data and present a plan, a “North Star” for the future direction of travel. Some of my data was inherited, so it was becoming clear I was going to have to draw supporting data myself to have the confidence to present and stand by it.
The one-on-ones went well for the most part. Folks are generally happy. We’re making the right moves and changing the right things. Agile has some growing pains, but I get it—this isn’t my first time transforming from “Wild West” to “Tamed West”—individuals and interactions over processes and tools.
They’re engineers, though, they’re want to spend more time coding, less time in meetings, more time refining, less time talking about refining.
As I interact with the team, though, I’m reminded that experience isn’t something that can be skipped, great theory and intelligence only gets you so far.
I’ve been the engineer that hates meetings.
I’ve been the engineer that gets perfectionist procrastination.
I’ve been the engineer that thought only performance mattered and failed to realize presence and perception need to go with it.
I’ve been the engineering manager that struggled to delegate.
I’ve been the engineering manager that missed coding and spent too much time in the woods to meaningfully impact the bigger picture.
At each stage of my career I’ve been refined both by experience and learning from the good, the bad, the ugly of others. I’ve learned to treat individuals as individuals with their own desires and needs.
Turned out by the evening my needs were old-fashioned cocktail and fish and chips (well, poutine — for gravy’s sake) and some good conversation.
Hotel.
I adjusted our presentation to use numbers I could stand by and drew up my talking points—things are coming together.
FaceTime—my daughter got all A’s in her exams and was pretty proud. So was I! Like father like daughter? Perhaps more true than I thought: there was one exception to those A’s: Spanish! That night, I also forgot to do my DuoLingo.
Lo siento.
Sleep.
…thursday
Today was the day to present out progress as an Engineering organization to executive leadership but also the day to fly out back to New York Metro via Newark (EWR), the chances were pretty high that one of those things were not going to go well. I’ve learned to put myself in a place to succeed when there are outcomes I can control (the former) and be largely at peace with those I cannot (the latter).
Early into the office, this time with a peppermint mocha with an almond milk. I have started the day with a sore throat and chesty cough but of course I do because I’d need to talk today, starting with a one-on-one.
Next up I three way choice between three stand-ups, a reporting alignment call, and a sync up with our support group. I picked the middle one this time.
Following that would be an “all hands” technology call where we all got together for executive leadership to discuss with the engineering team we’re going, how we’re doing, and what up next. All very impressive, technical issues of the day aside (between Zoom, Teams, Windsurf, and Jira the tools did not have the best week).
Next was the engineering review presentation to executive leadership. Wish me luck?
Luck is when happens when preparation meets opportunity.
The presentation we had went, well, well? I mean, there’s certainly work to be done and a few takeaways, we can and do need to do better in multiple areas, but our direction of travel is the right one. I realized need to do more on the numbers, this is something we were aware of — those I presented I was confident of but also cognizant of where and how we could improve them as well as the steps we’ve taken so far to get where we are.
Another plan had come together.
How about the plan to leave at lunch-time so I could guarantee I’d fly back in the late evening? Fail. Utter failure. The plane didn’t leave the tarmac until 945pm, landing at almost 1230ish am, so I wouldn’t get home until just before 2am. I’ve flown a lot this year, I was at peace with it—I could offload my thoughts during our mad, sad, glad sprint retrospectives on Friday.
Whilst stranded, I wrapped up some documentation for the team and a couple of calls I had expected to miss, scrolled through some Sora Disney animation brain rot, discovered Plur1bus (an excellent sci-fi btw—”Pluribus: out of many, one”) and settled for cranberry juice on the plane.
FaceTime, no. Face time? No. Everyone was either asleep or too sleepy—I was mentally and physically spent and greeted with a message to pick something up on the way home. [-_-]
The highlight was a talkative Uber driver. Talking at the end of a day as long as this is usually something I want to avoid, especially for a hour-long journey past midnight. To be fair, though, I had encouraged it—I was completed drained but I could see that he wanted to talk. After all, his day job was software engineering and Uber driving got him from under his desk— we talked GenAI, social media, screen time, and life in New York vs New Jersey—building character vs building family.
3am. Sleep.
…friday
I was greeted by my youngest around 7am with 100s of kisses and hugs all of which I had to accept largely with my eyes still closed. I admit, it was good to feel the love.
On Friday I needed to be in my first meeting by 830am, had a release call, a sprint review, three sprint retrospectives and sprint approval calls, and had an interview which had just “appeared” in the calendar amongst them all. Frankly the interview had to go—mentally, I was barely available, there was no coffee at home, and we didn’t need two of us for a screening interview, anyway.
I made it through our sprint review and sprint retrospective marathon—it was good to see the team collaborating and even those who were generally quiet raising points and working well together with others and coming up with solutions. The general reaction to agile being introduced was positive. Their pain points were expected. Growing pains.
Engineers hate meetings.
By evening I was now well and truly spent, barely able to keep my eyes open.
I ate some Thai food and waited for everyone to get arrive home.
Face time? I tried, I really did but I was ready for tomorrow yesterday.
Sleep.
…saturday
At just past 3am I could hear all hell breaking loose, the youngest was sick, the oldest was up and my other half was fielding the drama without me—clearly unhappy as a result.
I couldn’t physically move.
Mentally I also knew getting up at that point would render me useless for the whole of the day. I’d likely have a migraine the whole weekend.
This is where the realization dawned that my successes are often intertwined with my failures and limitations.
It wasn’t going to be a DuoLingo-like “perfect week”. So I just… slept.
I am human.
Instead, I got up in the by 830ish in the morning used my Streak Freeze—taking myself to Starbucks and buying the family, and myself a Starbucks breakfast.
Now here I am, hitting reset, re-centering, listening to neo soul, writing.
Do you ever feel a bit lost in here? Too busy tracking hours to appreciate the flowers your growing? I do…
So here I am — a little tired, a little lost, but still wading through. Some weeks feel like a grind: a blur of daily stand-ups, sprint calls, delayed or canceled flights, and cold coffee, and yet, somewhere within all of that noise, things are growing.
Teams, ideas, the kids, me. I catch myself tracking hours, chasing plans, trying to make everything align — maybe that’s okay, maybe that’s what all of us are doing. Maybe the trick isn’t to slow everything down, but to notice the flowers even as I’m running past them.
Progress and peace don’t always arrive together, but they do eventually meet.
I know where I want to be. I just have to make sure I’m still chasing my dream, not someone else’s.
Just musing…
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