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Only you can give meaning to your career
How to mark moments that matter by planting a flag
An icon of a clock Publish Date
January 2, 2024
An icon of a human figure Authors
[10]Justin Searls
I have, for whatever reason, live-blogged my career. Posting technical
tips I’ve learned. Complaining about bugs I’ve uncovered. Elaborating
on struggles my teams have faced. Mixed in with the substantive stuff
has been plenty of vain ephemera that many would rightly describe as
“over-sharing.” My brother sent me [11]this last week and I felt
personally attacked:
Everyone is fighting a battle you don’t know about. Except for me. I
am complaining loudly about my battle. Everybody knows about it.
So if you’ve borne witness to how much of my life I have spewed
indiscriminately onto the Internet: first, I’m sorry. And second,
please know that my vocation as a limelight enthusiast is emphatically
not what I’m encouraging when I say this: I really wish more people
took the time to reflect on the moments that mattered most in their
careers and did more to memorialize them.
Ask yourself: what experience in the Spring of 2019 had the greatest
impact on how you go about your work today? Or 2017… what was 2017 all
about? Think about the project you’re focused on right now. What will
you remember about it a decade from now? In what ways are you reaching
(or being stretched) beyond your comfort zone? If Walter Isaacson were
writing a bullshit hagiography about your life instead of some
[12]other schmuck, what would he have to say about you in your current
chapter?
How does it feel to be asked these questions?
Early in my career, being asked those questions would have felt like a
personal attack. But why? I had the tremendous privilege to have a job
that paid me to use my mind instead of my hands, that afforded me the
comfort of working behind a desk instead of out in a field, and that
saw value in my continued growth instead of viewing me as a resource to
be extracted and consumed. Those relative luxuries signaled that (by
some definitions) I had “made it,” but nevertheless there I was:
working overtime and shedding hair to deliver projects that meant
nothing to me. As the years passed, I knew I was accomplishing
something and growing somehow, but I found myself totally unable to
articulate what or how.
Not unrelatedly, I grew to hate answering “what do you do?” at parties.
People tend to spend about a third of their lifespan at work, and
that’s assuming they’re fortunate enough to retire at some point.
That’s a big chunk of life to be rendered meaningless! So I decided to
be someone whose work mattered—to myself, if no one else.
Deciding to take ownership over the meaning of my work has
unquestionably changed my life for the better. This post is the first
time I’ve shared my process publicly, and my hope is that others will
benefit from reading it. Given how dissatisfied most people seem to be
with their careers, maybe that’s you.
[13]Periodically plant a flag
Despite the fact that I live in Florida and I’m typing this sentence
poolside in shorts and a t-shirt in mid-December, I conceptualize time
with the passage of seasons. There are seasons when my life demands a
lot from me and my career is forced to take a back seat. There are
seasons when my work is particularly engaging and my life falls into a
pleasant-but-unremarkable routine. There are, of course, seasons when
both are challenging simultaneously, but hopefully not too many.
Whatever the case, I find myself pausing every three or four months and
pondering, “what from the last season of my life is worth remembering?”
It’s not like I have a reminder scheduled or anything. I don’t gather
my colleagues and family for a standing meeting to review my
achievements from the prior quarter. It’s more like an itch I’ve
trained my brain to scratch whenever I go more than a few months
without examining where my time has gone and what I have to show for
it.
I often refer to this regular act of reflection as “planting a flag” to
symbolize whatever I want to stand out when I look back on a period of
my life. In my case, these flags usually take the form of creative work
like a blog post, a conference talk, or an open source library, but
however you choose to imbue meaning into your experiences is entirely
up to you. The most important thing is that you sit with them long
enough to associate your memories of those experiences with why they
mattered. When useful artifacts shake out of my process that can help
others along in their own journeys, that’s a happy accident as far as
I’m concerned.
[14]How to plant a flag
So, how does one actually assign meaning to a heretofore meaningless
experience? This is the process I’ve settled into over the years to
identify and commemorate my life’s watershed moments:
1. Reflect: spend some unstructured time—maybe on a walk or with a
notebook—and let your mind wander through the previous season of
your life. A lesson you learned. Feedback that encouraged you. An
interaction that left an impact. A moment that inspired you. I’m
especially drawn to memories where emotions ran high—maybe I was
really worried before a hard conversation or relieved after a
colleague helped me solve a hard problem. If I draw a blank, I scan
my e-mail and calendar to jog my memory. If, nothing stands out
after all that, I don’t force it; I’ll give the exercise a rest and
come back to it a few days later
2. Collect: considering the experiences that came to mind when
reflecting, which ones were distinct and new to you? Anything new
you learned is, by definition, novel, and would obviously qualify.
It’s naturally harder to identify familiar-seeming experiences as
novel, but perhaps there was something unique and interesting
hiding in the otherwise banal UI control you shipped last month.
Why do this? Because by filtering out everything you’ve seen and
done before, whatever flag you plant will stand taller, and you
won’t risk mistaking this moment and its meaning for another. If
this step filters everything out because nothing seems sufficiently
novel, widen the aperture a bit—surely something interesting
happened in the last few months. And, try as you might, if you go
long enough with nothing to show for it, the meaning you’re
searching for may be that it’s time to make a change
3. Connect: for each of the experiences you’ve collected, try to
understand how they might connect to future situations. A new tool
or technique might empower you to do something you couldn’t
accomplish otherwise. A painful mistake might warn your future self
to avoid try a different approach next time. Since I can’t see the
future, I imagine what impact each such insight might have had if
applied to experiences from my past. “If I’d had learned this years
ago, how would it have changed other events in my life?” If I can
think of several moments in my life that would have played out
differently, that’s as good of evidence as any that it has the
potential to make an impact on you going forward
4. Protect: memory is fleeting, and the work you do to identify
moments that matter will quickly fade away if you don’t do
something to mark the occasion. Memories thrive in novelty and
wither in predictability, so the only wrong answer would be to
enshrine every life lesson in the exact same way. Because creative
endeavors necessarily result in the creation of something new,
they’re a great way to clarify meaning and cement memories. My
go-to creative outlets are essays, videos, and code, but yours
might be songs, recipes, or [15]Etch A Sketch portraiture
That’s it! Reflect, collect, connect, and protect.
(See what I did there? How all the steps rhyme. That’s the kind of
thing you’ll be able to pull off with a decade of practice doing this.)
[16]This all happens in hindsight
If you’ve ever had a job that encouraged you to make quarterly or
annual goals for yourself, you may have noticed that a lot of those
goals go unfinished. By the time performance reviews roll around,
people often feel forced to justify why they didn’t achieve this or
that goal. Regardless of the reason—maybe learning some skill was no
longer relevant or the business’s strategic priorities shifted—the
failure to meet a goal is often rooted in a failure to predict the
future. I’m sure managers hope people will feel inspired and
accountable to pursue their goals creatively, but in my experience they
more often instill procrastination and anxiety. If there’s any
creativity exhibited in annual goal rituals, it’s usually when people
feel forced to weave a narrative that kinda-sorta connects a stated
objective to whatever mostly-unrelated work they actually did.
To wit, I’ve never accomplished anything I felt proud of by setting a
goal. In fact, the surest way to ensure I don’t do something is to set
a goal. When asked to set goals for myself, I’ve found that expressing
the goal (as opposed to achieving it) becomes my overriding objective.
The moment a manager approved my list of goals, I felt that I had
completed the work asked of me and I would instantly lose all
motivation to pursue the goals themselves.
This explains why planting flags can succeed where goal-setting fails.
If what I’m searching for is meaning in my work, setting a goal creates
an expectation of where, when, and how my future self should find that
meaning. High pressure. Focusing on doing my job well and reflecting on
whatever I did in retrospect, however, has allowed me to sift through
my experiences, identify patterns, and give meaning to them. Low
pressure.
Instead of studying something you think you might need in the future,
wait for the need to arise and then immerse yourself in learning it.
Instead of feeling stressed and distracted by the fear that you’ll run
out of time before hitting an annual goal, do your work diligently and
look forward to the next opportunity to reflect on the things you’ll
achieve. Instead of reducing your existence at work into a series of
boxes to check in a prescribed career plan, focus on being truly
present and intentional at work and open to wherever that might lead
you.
[17]Who, me? Yes, you!
There’s just one last thing to talk about: you, and why you don’t
already do this.
It’s not like this retrospective process of imbuing meaning into one’s
work is particularly clever or insightful. I don’t think I’m a genius
for arriving at the following three-step formula to having a deeply
meaningful career and leaving a memorable legacy:
1. Work really damn hard
2. Occasionally gather highlights
3. Commemorate them somehow
But if it’s so obvious, why don’t more people do this?
I wonder if it’s because everything above might seem like the exclusive
domain of the Thoughtleader™ class. “I don’t have (or necessarily want)
an audience to read my blog posts or watch me speak, so this ain’t for
me!” you might be thinking.
This line of thinking is reasonable, but it’s based on an assumption
that doesn’t always hold.
It’s true: if you believe the purpose of creating something borne out
of your career experience is for other people to see and appreciate it,
then maybe it makes no sense for you to bother. Not everyone craves
attention. Building a following inevitably attracts a certain number of
trolls. And if you build it, odds are people won’t come. I can’t
guarantee anyone will run your code, read your blog, or watch your
talk.
But here’s the thing: I create these things for me and me alone. When a
bunch of people read something I wrote or show up to one of my talks,
do I find it encouraging and validating? Sure. But it’s not what drives
me. I started creating things to punctuate my life’s sentences long
before anybody took an interest in me and I wouldn’t stop even if
everyone loses interest in me.
What’s more, a lot of (ugh) content creators are the same way. In the
course of my travels, I’ve gotten to meet many of my heroes, and while
a few have disappointed me spectacularly (don’t meet your heroes!),
I’ve found that a surprising number of them got into the
thought-leading racket for the same selfish reason I did. They create
stuff to scratch their own intrinsic creative itches and to give
meaning to their careers. If other people’s attention factors in at
all, it’s usually to justify the time they spend making stuff.
[18]Justin Searls
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Double Agent
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Agent 002
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Orlando, FL
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[24]16 things you believe about software
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joke…and people can't help themselves—they're still filling it out!
Here's what they think
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[25]Justin Searls
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[27]Shared values can make the difference for your engineering team
Ever feel challenged in how to level up your engineering team's
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References
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11. https://x.com/TheAndrewNadeau/status/1647622603698257921
12. https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281
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15. https://www.etsy.com/shop/PrincessEtch
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27. file:///posts/2023-02-20-shared-values-make-the-difference/
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32. https://link.testdouble.com/blog-cta-sales
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38. https://testdouble.com/contact
39. https://mastodon.social/@testdouble
40. https://github.com/testdouble
41. https://www.linkedin.com/company/testdouble
42. https://twitter.com/testdouble
43. tel:+16143494279
44. mailto:hello@testdouble.com
45. file://testdouble.com/privacy-policy
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