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[1]Test Double The Test Double logo
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[9] Blog [10] Posts
Only you can give meaning to your career
How to mark moments that matter by planting a flag
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January 2, 2024
An icon of a clock Publish Date
January 2, 2024
An icon of a human figure Authors
[11]Justin Searls
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[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 [12]this last week and I felt personally attacked:
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.
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.
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 [13]other schmuck, what would he have to say about you in
your current chapter?
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?
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.
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.
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.
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.
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.
[14]Periodically plant a flag
[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?”
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.
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.
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.
[15]How to plant a flag
[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:
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
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 [16]Etch A Sketch portraiture
That’s it! Reflect, collect, connect, and protect.
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.)
(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
[17]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.
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.
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.
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.
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!
[18]Who, me? Yes, you!
There’s just one last thing to talk about: you, and why you don’t
already do this.
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
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:
But if it’s so obvious, why don’t more people do this?
1. Work really damn hard
2. Occasionally gather highlights
3. Commemorate them somehow
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.
But if it’s so obvious, why don’t more people do this?
This line of thinking is reasonable, but it’s based on an assumption
that doesn’t always hold.
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.
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.
This line of thinking is reasonable, but it’s based on an assumption that
doesn’t always hold.
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.
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.
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.
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.
[18]Justin Searls
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.
An icon of a human figure Status
Double Agent
[002]
An icon of a hash sign Code Name
Agent 002
[19] Justin Searls
An icon of a map marker Location
Orlando, FL
An icon of a human figure Status
Double Agent
An icon of a hash sign Code Name
Agent 002
An icon of a map marker Location
Orlando, FL
[19]Twitter [20]Mastodon [21]Github [22]LinkedIn [23]Website
[20] Twitter [21] Mastodon [22] Github [23] LinkedIn [24] Website
Related posts:
[24]16 things you believe about software
[25] 16 things you believe about software
Over 6 years ago, I made up an unscientific personality quiz as a
joke…and people can't help themselves—they're still filling it out!
Here's what they think
Over 6 years ago, I made up an unscientific personality quiz as a joke…and
people can't help themselves—they're still filling it out! Here's what they
think
An icon of a clock Publish Date
October 10, 2023
An icon of a clock Publish Date
October 10, 2023
An icon of a human figure Authors
[26]Justin Searls
An icon of a paper organzier Categories
[27]Community
An icon of a human figure Authors
[25]Justin Searls
[28] Shared values can make the difference for your engineering team
An icon of a paper organzier Categories
[26]Community
Ever feel challenged in how to level up your engineering team's effectiveness?
Apply values in day-to-day work. That's how you build great software and great
teams. Here's how Test Double does that.
[27]Shared values can make the difference for your engineering team
Ever feel challenged in how to level up your engineering team's
effectiveness? Apply values in day-to-day work. That's how you build
great software and great teams. Here's how Test Double does that.
An icon of a clock Publish Date
February 20, 2023
An icon of a human figure Authors
[28]Cathy Colliver
An icon of a paper organzier Categories
[29]Leadership
[30]Teams
[31]Our Company
An icon of a clock Publish Date
February 20, 2023
An icon of a human figure Authors
[29]Cathy Colliver
An icon of a paper organzier Categories
[30]Leadership
[31]Teams
[32]Our Company
Looking for developers? Work with people who care about what you care about.
We level up teams striving to ship great code.
[32]Let's talk
[33] Let's talk
[34]Home [35]Agency [36]Services [37]Careers [38]Blog [39]Contact
[40] Mastodon [41] GitHub [42] LinkedIn [43] Twitter
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[44] 614.349.4279
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Founded in Columbus, OH
[47] Test Double
[39]Mastodon [40]GitHub [41]LinkedIn [42]Twitter
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Founded in Columbus, OH
References:
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References
1. https://testdouble.com/
2. https://testdouble.com/
3. https://testdouble.com/agency
4. https://testdouble.com/services
5. https://testdouble.com/careers
6. https://blog.testdouble.com/
7. https://testdouble.com/contact
8. https://blog.testdouble.com/
9. https://blog.testdouble.com/posts/
10. https://blog.testdouble.com/authors/justin-searls/
11. https://x.com/TheAndrewNadeau/status/1647622603698257921
12. https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281
13. https://blog.testdouble.com/posts/2024-01-02-plant-your-flag-career-advice/#periodically-plant-a-flag
14. https://blog.testdouble.com/posts/2024-01-02-plant-your-flag-career-advice/#how-to-plant-a-flag
15. https://www.etsy.com/shop/PrincessEtch
16. https://blog.testdouble.com/posts/2024-01-02-plant-your-flag-career-advice/#this-all-happens-in-hindsight
17. https://blog.testdouble.com/posts/2024-01-02-plant-your-flag-career-advice/#who-me-yes-you
18. https://blog.testdouble.com/authors/justin-searls/
19. https://twitter.com/searls
20. https://mastodon.social/@searls
21. https://github.com/searls
22. https://linkedin.com/in/searls
23. https://justin.searls.co/
24. https://blog.testdouble.com/posts/2023-10-10-16-things-you-believe-about-software/
25. https://blog.testdouble.com/authors/justin-searls/
26. https://blog.testdouble.com/categories/community
27. https://blog.testdouble.com/posts/2023-02-20-shared-values-make-the-difference/
28. https://blog.testdouble.com/authors/cathy-colliver/
29. https://blog.testdouble.com/categories/leadership
30. https://blog.testdouble.com/categories/teams
31. https://blog.testdouble.com/categories/our-company
32. https://link.testdouble.com/blog-cta-sales
33. https://testdouble.com/
34. https://testdouble.com/agency
35. https://testdouble.com/services
36. https://testdouble.com/careers
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