Ruth, our puppy, keeping me company while I do some work.
For nearly nine years, Shubox has been a part of my life. It started as
a passion project — a SaaS product that I dreamed might one day stand
on its own. At the time, success, to me, meant autonomy. The more users,
more revenue, the more viability, meant that maybe it could replace my
day job. That was the vision.
(Does that story sound familiar? Work a full time job? Create a side-hustle
that pops, concentrate on that full-time? Yes. It does sound familiar.)
But over time, my definition of success evolved. These days, success
looks a lot more like balance: meaningful work at my full-time job, more
time with my family, and projects that bring me energy rather than drain
it. In that light, keeping Shubox running just didn’t fit anymore. This
is why I made the decision to send an email out last week to customers,
colleagues, friends, supporters, and advisors, that I would be shutting
it down by the end of the year. Emails have been sent out. People have
been notified. I will start the 3 month process of shutting all moving
parts down.
It wasn’t a single dramatic event that led me here, but rather a quiet
repetition: the voice in my head saying, “I should really work on Shubox.”
I heard it one (maybe ten) too many times, often when I’d rather be fully
present with my family. That’s when it clicked — instead of energizing
me, Shubox had become a weight.
I’d had some conversations with friends about it (shout-out to Ben who
in a catch-up conversation made me think really hard about this).
Additionally, my CPA would, like clockwork, remind me every year that we
could wind down all corporate considerations to make the yearly conversation
reduce by one (shout-out Peter! 🐐️). The thought had been bouncing around
in there for a while and when met with the experience above, I think I knew
it was time.
The decision to walk away from Shubox has also changed how I think about
these personal projects. What is “success”? Success isn’t just about longevity
or profitability or autonomy. It’s about how well a project will fit into my
life and whether it adds more than it takes. A successful side project might
be small, fun, and light — not necessarily something that has to “make it big.”
I don’t think anyone would ask me for advice. But, if you’re wrestling with
whether to shut down a project of your own, here’s what I’d say:
Listen to that inner voice; it’s usually telling you the truth.
Don’t measure yourself against other people’s expectations. Only you know whether a project is worth your time.
Letting go doesn’t mean failure. Sometimes it’s the most thoughtful, mature decision you can make.
You’re not giving up on creativity; you’re just making space for projects that actually fit your life.
In closing, Shubox will always mean a lot to me. It taught me about building,
maintaining, and, eventually, letting go. More importantly, it taught me
about myself. While Shubox is coming to an end, my creativity and my desire
to build isn’t. It’s just shifting into something lighter, more sustainable,
and more aligned with where I am today. I’m sure I’ll have something else to
share in the not too distant future.
One of the gifts for my son this past holiday season was that we would bring
him to Fenway Park for the first “Fenway Fest”. Typically the Red Sox have
a “Winter Weekend” but this year moved it home, which is … much more
convenient? For us, at least.
Of course getting to meet the players and get some autographs and cards signed
was the highlight, but the absolute cherry on top of the entire event was the
ability to be in Fenway Park in the middle of a beautiful snow storm.
Fenway. Snow. (animated)
"Carl Yastrzemski" welcoming us to Fenway Park.
The Ted Williams statue outside of Gate B.
FENWAY 2025.
The entrance to Fenway dusted with snow, with the Green Monster in the distance.
The mini-est of snowmen.
Center and right field bleacher seats covered with snow.
New Balance.
As cliché and corny as this may be, still: tend to your career like a garden.
Preface
When I say “no one teaches you”, I mean that there are life lessons that are
not among the typical curriculum provided to young adults as they begin
navigating their ADULT adult lives. Not from their schools, their first jobs,
and not from their parents. This post is a reflection on life
lessons you may have to learn the hard way - like I did.
No one is paying attention to you at work. (Like, really seeing you perform
at that high level.)
Well, mostly. Maybe if you’re some wunderkind? Or 10x unicorn? Maybe.
But no, mostly. Nope.
Sorry.
Why? Because everyone is also trying to make their way, get by, keep their
head above water, or get to the end of the day or week. Being an adult is hard,
and most of us are just tired.
Of course there are always exceptions to the rule. People around you may care,
and may be trying to do what they can to help you excel and get that promotion,
but at the end of the day that responsibility ends up at your feet. The
responsibility to prove that you are doing everything you need to do to move up
that ladder, is ultimately on you.
For an interesting read on what it’s like navigating advancement of a career
in “BIG TECH” (scare quotes!), there is this post from Michael Lynch -
“Why I Quite Google to Work for Myself”. This post has stuck with
me for months, so I couldn’t write my own thoughts without sharing his.
Now, here’s where some of those exceptions kick in - if you’re lucky, you work
at a company that has a tried and true process for showcasing the impact you
have delivered to the business. Perhaps that’s a set of documents that serve as
a framework for advancement, or the company uses something like Lattice to good
effect, or your manager is constantly on your ass to document everything. But
that’s a lot o’ “buts” and “maybes”.
But … most don’t.
So don’t expect that the people in charge of making decisions will just know.
They won’t.1
With that cynicism laced with realism—or vice-versa—out of the way,
what now?
Keep receipts. Document what you’ve delivered month-over-month. What were your
personal initiatives? Where have you delivered against your goals and promises?
Who have you helped improve, and are you able to state how and why? Be direct
on what you intend to do. What are your plans? Look at your organization’s
leveling rubrics and not only track where you meet the expectations, but can
exhibit how you have internalized those skills and have burned into muscle
memory.
I want to be clear on something - I suck at this! I am often so focused on the
day and week at hand, that I neglect to suitably prioritize the documentation
of slow and steady growth. This is as much a reminder for me as it is for
anyone I might have a similar conversation with. I wish I’d more people in my
orbit over the years to beat this into my brain. Alas, I did not. C’est la vie.
(Again, not their problem.)
So if you’re reading this, consider the above. Good luck. Look out for #1.
Keep your receipts. And let me know how it goes.
I worked at this consultancy several lifetimes ago. I was doing good work (as far as I knew) and had several people telling me as much. The challenge at the time was that the department we were in skewed more towards the design/IA/UX side of work at a digital agency, but as a specialist in front-end technology I, and others, were on the fringes and met with an apples vs. oranges, compare-and-contrast, problem. I was not equipped at that time to make the case for myself and outline where my personal value and the role’s trajectory (from a larger digital evolutionary perspective) was. My memory recalls that I eventually did get that promotion, but the glacial turn towards getting there burned me out enough to leave when I could. To be clear, most of that was a product of my inaction and the inability to realize this. ↩
When I say “no one teaches you”, I mean that there are life lessons that are
not among the typical curriculum provided to young adults as they begin
navigating their ADULT adult lives. Not from their schools, their first jobs,
and not from their parents. This post is a reflection on life
lessons you may have to learn the hard way - like I did.
When I graduated high school I decided to stay relatively close to home and
attend the University of Hartford, a medium-sized liberal arts school in CT
known for their arts programs. Theater, ballet, music, illustration, art
history, graphic design - all well represented by the programs at UHA. That
first year I chose my major, art with a concentration on illustration. I spent
most of it in art history classes and foundational 100 level classes, figure
drawing and the like. I enjoyed some of it1. However, I quickly ran into
something that would put a hard stop to my dreams of drawing superheroes for
Marvel or DC2.
“Crits”. Critiques. Criticism.
I couldn’t do it. Could not handle it. (I was a sensitive kid3.) After so
many years of people complimenting my doodles, my art class projects, the comic
strips for the school paper, I was just not ready for the heavy dose of real
criticism.
Reframing Criticism
Looking back now, I wonder what would have happened if I’d had the proper
framing—the framing that “criticism” was a coaching device, not a vessel
for insult and derision4. If I had known these professors were there to
break things down in order to rebuild better and bolder, would I have stayed?
Perhaps.
And therein lies a lesson: knowing the intent behind the feedback matters.
When we understand the why behind feedback, it transforms how we process and
respond to it. In hindsight, I see that feedback is not inherently
negative—it’s a tool for growth.
The link to ctocraft is one of the better distillations of many themes learned
from reading the soon-to-be-mentioned “Thanks for the Feedback”. If you’re
not interested in reading an entire book on the topic, just go read that blog
post. I wish I had written it.
Evaluation: Assessing your performance against a standard.
Appreciation: Recognition for your efforts or achievements.
There are also two sides to the feedback equation: giving and receiving.
Both are emotional intelligence (EQ) skills that require training and practice.
To give effective feedback, ask yourself:
Do you understand where the receiver is emotionally or mentally?
Have you considered how they prefer to receive feedback?
Do you know the context in which they like to receive praise or guidance?
To receive feedback effectively, reflect on the following:
What is the intent or motivation of the giver?
Can you temporarily set aside your ego or pride and compartmentalize?
Can you resist the urge to respond defensively and instead focus on
understanding the “why”?
How to Build Your Feedback Skills
How might you work on these things? The book “Thanks for the Feedback”
is an excellent resource for examining these things. I would recommend it to
anyone navigating a career in the corporate space. (Not to mention spouses.
And parents.) There’s much to learn in there that often no one will take the
time to explain or examine with you5.
I am grateful that the managers and peers at my day-job had us read this as
part of a work book club. It has been immensely helpful.
A Reflection on Art School and Beyond
Thinking back, I have wondered how my time in art school would have differed if
I’d been better equipped. What would my career trajectory look like? With the
crystal clear 20/20 hindsight I’m not too broken up that things went the way
they did. It all worked out pretty okay in the end.
At that time, if we’re talking “take it, or leave it” - the art history part I’d put in the “leave it” bucket, certainly not “take it”. My professor was dreadfully boring, the lectures were huge, and my ADD was having absolutely none of it. Although, I guess, I do still know what doric columns, flying buttresses, and the Venus of Willendorf are. ↩
Or Image. Or Valiant. This was the 90’s after all. ↩
Still am, just equipped with better coping mechanisms. ↩
To be fair, some of the professors absolutely did take joy in ripping things to shreds. Cruel? Maybe. (Probably.) But the emotional callouses may serve as armor in what is ostensibly a cruel world. ↩
An extra tidbit: if you have done some examination of the self and know how you prefer to give and receive feedback, tell people! Write a personal README! Share it with your manager and teammates! Wouldn’t it be helpful to tell people up front the cheat codes on how to work with you? For me, it’s been a tremendous help. ↩
“I’m experimenting wth Caddy as a replacement for Nginx.”
Right now, that’s an aspirational statement, and not entirely factual.
Because, I would need to get Caddy to run properly to actually experiment
with it.
Alright, haha – enough sarcasm.
In order for me to get Caddy to run with the following requirement - must have
a Caddy docker image that supports DNSimple’s TLS challenge. The stock Caddy
docker image you get from Dockerhub does not
have all of the DNS providers. As a result, you need to build your own image
containing the DNSimple module. How
might you do this?
Edit your Dockerfile.
FROM caddy:builder AS builder
# Set Go environment variables to fetch dependencies directly
ENV GO111MODULE=on
ENV GOPROXY=https://goproxy.io
ENV GOSUMDB=off
RUN xcaddy build --with github.com/caddy-dns/dnsimple
FROM caddy:latest
COPY --from=builder /usr/bin/caddy /usr/bin/caddy
When I attempted to build an image with the above, not containing the ENV’s
I would run into errors related to the proxies used to fetch the Go libraries.
The ENV’s above were helpful to get things to work, thanks to the comments
here in a Github issue.
An engineering manager in Boston. I write about my family, my (bull)dogs,
code and technology, and whatever projects I am currently obsessed with.
I occasionally post on Mastodon (@jayroh)
and at BlueSky (@jayroh.dev).
