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 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 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.

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.

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 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.)

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.

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.

Justin Searls

Person An icon of a human figure Status
Double Agent
Hash An icon of a hash sign Code Name
Agent 002
Location An icon of a map marker Location
Orlando, FL