A Few Things I Learned While Planning Five Million Weddings
In my final week as Vice President of Product at The Knot, a thoughtful colleague of mine asked, “Knowing what you know now, what advice would you give your 30-year-old self?”
By this point, I was already deep in the well of self-reflection, but my friend’s prompt shook loose some thoughts and feelings I was grateful to explore anew.
But first, some context around what I’ve been doing these past few years.
Each year, more than 80% of the estimated two million couples in America trust The Knot to help them plan their wedding. They read articles, curate photos, search dress + tuxedo styles, plan with the checklist, personalize their wedding website, and book local vendors — all to bring that one, magical day to life.
I joined The Knot as a product and UX consultant in late 2013, and I was hired full-time in May 2014 as VP of Product. I spent the next couple years alongside a brilliant, creative, and thoughtful team, exploring the depths and breadth of product development. We built a CMS, optimized landing pages, launched a transactional marketplace, redesigned a 10-year-old WYSIWYG website editor, invested heavily in mobile, established user-research methodologies, and, in 2015, rearchitected and redesigned the whole damned site.
But what about this claim that I planned five million weddings?
Well, there’s a story about President Kennedy visiting NASA in 1962. While touring the facility, he approached an old man holding a broom and asked what his job was. He replied:
“I’m helping to put a man on the moon.”
Like most anecdotes about Kennedy, this one’s as dubious as it is delightful — but being a sucker for sentimentality, I’ll buy it.
So, in a sense, yes: by working on the team who built the company’s website and mobile apps — which generated a majority of XO’s revenue and kept the ship afloat — and helping steer the company’s business and organizational strategy, I in turn helped millions of couples plan their weddings. Pretty cool, right?
And I can say without hesitation that it was the best experience in my professional life — not because of what I did, but rather what I learned in those three-plus amazing years.
So harking back to my friend’s question about my advice for a younger me, I’ve (barely) narrowed it down to what my 30-year-old self would understand and appreciate — deliberately leaving out a few things that’ll be important for him to learn on his own (sorry, bud).
Note: the use of “you” in the piece is directed at that younger me, and not the reader. I don’t purport to know what’s good for anybody else — only what’s worked for me.
Define Your Own Value
Bernard Hopkins — a great boxing champion and a personal inspiration— said in an interview a few years back:
“If you don’t know your own value, somebody will tell you your value, and it’ll be less than you’re worth.”
While serving an 18-year prison sentence, Hopkins learned how to box. He got out in five, and immediately defined his own value by straightening out and becoming a professional fighter.
Like the warden who told Hopkins, “see you again when you wind up back in here,” too many others would consider an ex-con just a future-con-in-waiting. Or, at best, they’d sell him some ersatz American dream and hope he’d just disappear.
But instead, Hopkins fought his way to fame, winning the middleweight title and holding it for a record-setting ten years. Much later, he became the oldest world champion in boxing history — at an unfathomable 49 years old. He also became a manager and mentor to many young fighters who struggled to define their own value.
What I learned the past few years — and from Hopkins — is that the path laid out before me is not actually mine. It belongs to the people who came before me, a carbon copy of their path, a mere simulacrum of success. It was not created with me in mind.
As I wrote about in “Redefining Ambition,” managers and mentors and leaders will encourage you to follow their path. Managers make Senior Managers make Directors make Vice Presidents, who tell their followers: you could have my job someday. It’s not malice or selfishness, it’s just what they know. And after all, they’re successful, so what worked for them would work for you, right?
Well, not if their values don’t align with yours.
Too often, managers will define your career by easy-to-grasp milestones: title and seniority and ownership and direct reports and exposure and compensation. At best, these are just objects: things you want but that don’t address any real need. Titles are arbitrary and seniority is relative, and no salary can offset that awful, disjointed feeling of being unfulfilled.
At worst, they’re tricks devised to distract you from seeing the things that do matter — like (for me) creating, writing, playing music, reading, and learning.
What makes your path so special is that it’s unique to you — and that it’s undefined. Don’t be bamboozled by the ever-inclining treadmill of corporate rewards. And don’t let anybody else — regardless of their intentions — point at some foreign future and tell you it’s yours.
Only you can identify that path, and you’ll know it when you set foot on it.
And when that time comes, set your compass on true north and go! go! go!
Being Right Is Overrated
Bad news, hombre: you don’t know shit.
A year ago, you convinced a 40-person startup to hire you as their head of product with little more than a resume and a smile. You picked up some nomenclature from conferences and books, touted some vanity metrics, then made a decent case for building an iPhone app (after all, this was 2009). Boom! Hired!
Now this isn’t exactly bad because (mini-lesson right here) everyone else is making it up, too.
It’s only bad if believe your own bullshit.
In about a year, you’ll realize that your job isn’t to the know the answer, but to find it. This is the vital difference between Waterfall and Agile: rather than embark on a project with a pre-set answer, you’re follow a process that reveals the truth along the way.
This realization happened long ago for me, but until I joined The Knot it didn’t occur to me that I could apply this philosophy to how I think, act, communicate, and treat others.
Start here: admit to yourself that you’re probably wrong. It’s ok, you can’t possibly know everything, or even half as much as you pretend to. And even if you’re right, you’d be stupid not to take every opportunity to get smarter.
Listen to yourself in a meeting, acting like you know what people are talking about because you’re afraid of looking dumb. Recently, someone asked if you’d ever done any multivariate testing. Not knowing what it was, you answered, “We’ve done all kinds of testing,” and you sounded super dumb saying it. This is a terrible habit and needs to be broken.
Not sure where to start? Ok, repeat after me: “Wow, that’s a good idea. I hadn’t thought of that. Tell me more.”
And now: “I’m not familiar with that. Can you help me understand it a bit more?”
Or, simply: “What do you mean by that?”
And if you’re really struggling with it, try: “This is really interesting, but it’s totally different from what I had in mind. Can I think about this and get back to you tomorrow?”
These are all simple ways to admit that you don’t have an answer or, if you do, that you’re open to a better one. It doesn’t make you look dumb or weak or acquiescent— it makes you look like a reasonable human being who is smart enough to know he’s still got a lot to learn.
(And perhaps most importantly — another mini lesson — it shows that you value and respect your colleagues’ intelligence. What a nice feeling to give somebody!)
Believe me, I’m still not great at this. Film and TV and movies glamorize the quick-witted guy with the answer. There are no role models to follow in media and politics — no compromise or conciliation found there. We romanticize the bombastic mic-drop moment and imagine ourselves leaving our audience in stunned silence thinking, Who was that masked man?
But that’s not reality. You have to keep learning or you’ll atrophy — you have to be willing to be vulnerable, to be wrong.
Believe me, you don’t get better by having the answer, but by becoming an expert at finding it.
Trust Your “No” Instincts
I’ll admit, they’re pretty good. More than once over the years, you sought a second opinion on a potential new-hire, thinking, “They’re good, but something’s…off.” And each time, it eventually turned out that s/he was not right for the job (in one case, disastrously so).
Ditto that for a product that just didn’t feel ready for primetime. But it was so late in the process, and people were getting impatient, and to put the brakes on now…well, let’s just push it live and see.
And did disaster strike again? You bet your ass it did.
This doesn’t mean act impulsively on your instincts. I mean that if something gives you pause, then don’t proceed without more information. Don’t just sleep on it, seek a second opinion. Then seek a third one. Figure out what data is missing for you to feel confident moving forward, and go get it.
As a PM, you’ve developed a kind of Residual Circuit Device — that pair of red and black buttons on the wall socket that breaks the circuit when it thinks the radio’s fallen into the tub. Sure, it’s a little bit of a pain in the ass to have to remove an iPhone charger and reset the interruptor each time. But I’d much rather the RCD sometimes triggers on a false alarm then have it not trigger when it really needs to.
Share What You’ve Learned
As an avid rock climber, I always map out a route before I start. I sit on the floor compulsively chalking up my hands and imagining the sequence of movements that will get me to the top. But because it’s hard, from afar, to anticipate variables like weight and center of gravity, or to account for every inch of my (limited) reach, I’ll invariably arrive at a move that is not at all what it seemed from down below.
And that’s the moment I become a better climber.
For product and design philosophies, though, there’s not always practical application that allows for that kind of exploration — that is, except for teaching.
One of the ways I’ve gotten better at my core skills is by educating others on how to do them as well. Though often seen as purely altruistic, teaching is not limited to that: it can also be an opportunity to put an idea into practice, and to improve upon it.
Calling back a familiar theme here: sharing knowledge is important not because you’re right, but because you’re at least a little bit wrong.
The moment I say something out loud, it becomes malleable, communal — as though it’s not my idea but now our idea. There’s always the chance someone says, “That’s cool, but I read about this other way of doing that.” Or “Yes, and have you considered….?”
When I held knowledge tight to my chest as though sharing would cause some irreversible erosion, it never evolved and I never improved. Like calculating a climbing route from below but never actually trying to send it.
So I learned to be generous with what I knew, sharing as much as I could, and keeping myself always open to the same kind of generosity of others.
And if it turned out I was right, that the idea was intrinsically valuable enough to share, then I’ve strengthened my relationship with my peers and given them a gift — at no cost to me whatsoever.
Over the past few years at The Knot, I directly managed about 15 different people — some for the duration of my tenure, others for barely a blink during a re-org. And for each of those people, a different product — from ad-supported content to AI-powered chatbots. In all of this, change was the constant: Asana to Pivotal. HipChat to Slack. Waterfall to Agile. M-dot to Responsive. Documentation-driven development to user-centric design. Never mind the change that comes from new management, or new hires, or shifting economics, and so on.
In such an ever-changing sea, I needed something consistent to cling to.
So I devised simple framework that could easily copy and paste to new people and new products — of which there seemed to be an endless rotation. I based it on three of my personal core values that best applied to the job: courage, discipline, and empathy.
But more than a mantra, it’s a “system” that I can repeat for each for each problem, product, or person I’m addressing. I evaluate the needs of the situation and then mentally plot a single point on this triangle, closest to the value(s) required for addressing it.
The output: I always know how to distribute my energy among being courageous — with some disregard for process or, if need be, feelings — empathetic — prioritizing the needs of users or stakeholders over all else — or disciplined — relying on rigorous process and data to find the answer.
In every case, it’s a lopsided combination of the three — usually a mid-point between two of them — but always with one value as the highest priority.(Equally important is acknowledging that you can’t be everything all the time — something’s gotta give.)
On many occasions, this has kept me focused on the right aspects of the problem, and consistent in my communication. I would say to myself, “Ok, remember, we need to be disciplined here — store up courage for another day.” To others, I’d say, “I’m over-emphasizing Discipline here — at the deliberate cost of Empathy — because we agreed this phase requires process and structure.” This shared language adds transparency to consistency, and made me more accessible and accountable to my colleagues.
And after applying this dozens (hundreds?) of times, I found myself assessing new problems more quickly, and more easily recognizing patterns among them.
Know What You Love
It’s common to be told to “just go do what you love,” but that’s such desultory advice that it’s almost dismissive.
Face it: it might not be possible for me to make a career out of (and to make money off of) doing what I love. Take, for example, rock climbing, ukulele, chess, and writing: unless I break into the top 0.1% of these fields, there’s no “career” to speak of.
So I’ve come to accept that some things belong on the fringe. But to ensure the right mix of work and passion in my life, I first had to really know what I loved, and deeply understand what about those things moved me.
Case in point: Barcelona.
I have a habit of falling in love with a city when I visit it for the first time. How could I not love Barcelona? Food, wine, beaches, museums, excellent weather, and an unmarked vermouth bar on a hidden side street where we sat at tables made from barrels. I never had to do laundry, or go grocery shopping, or commute to work in a subway car in which somebody definitely just farted.
But I couldn’t just come home and say, “Fuck it, we’re moving to Spain!” It’s forever away from my family and friends, there are no jobs, the health care sucks, and my Spanish is no bueno. However, I didn’t want to lose that magical feeling the place gave me.
So I redirected my thinking to: “How might I make my life in Brooklyn more like that visit to Barcelona?”
Since that trip last March, I’ve made a concerted effort to appreciate the restaurants, bars, bookstores, cultural centers, and parks of Brooklyn as though I’m here only for a few days. I make it a point to be grateful (see below) for what Brooklyn has to offer, and to let myself approach this little borough with wild-eyed wonder each day.
Similarly, if I’m not going to make a living strumming the ukulele, how do I better construct my life around this thing I love?
When the weather was nice, I experimented with bringing my uke to work. I’d fingerpick it on the subway ride in (so quietly that no one could hear it), and then I’d stop in a peaceful public place (like this little enclave) and play a few songs before heading to the office.
With barely an extra 15 minutes added to my morning commute, I scratched a creative itch — and didn’t disrupt my job at all.
So it wasn’t a matter of turning my passions into work, but retrofitting my work/life to allow for more deliberate moments of creativity and wonder. As an added benefit, it helped me examine and appreciate my job for what it was, as opposed to constantly blaming it for not being as creatively fulfilling as my hobbies.
This is everything. It’s easily the biggest single learning in my adult life, and it was largely inspired by the wonderful people with whom I spent the last ~9.5% of my life.
It’s far too easy to be cynical, or ironic, or snarky, or to complain or blame someone else. It’s the territory of lazy, mean, selfish, entitled people. It surrounds the spirit with scar tissue: not life-threatening enough to take seriously, but it causes pain, limits the range of motion, and leads to other more serious injuries over time.
Enter, our hero, stage left: Gratitude.
First, there’s the tactical side: I write almost every day in a gratitude journal, and I take every opportunity to tell, text, or email someone when I’m feeling grateful for them. Even seemingly trivial things like LinkedIn endorsements or sending a postcard can trigger a little dopamine rush that makes you feel like life is just fucking awesome.
This leads to the second level: gratitude as a state of being.
Things happen in this headspace that are tough (for me) to explain. It’s like when you’re fit, how your body goes to work keeping you fit: your heart rate is lower, your resting metabolic rate higher, you sleep better, you crave healthier foods.
After making (and, yes, at first, forcing) a habit of expressing gratitude, I became grateful. I appreciated so much more the things I love that the rest…well, they just kinda stopped bothering me so much. I’m not saying I achieved nirvana, but I definitely feel more calm, centered, and balanced than ever before.
There’s an ancillary benefit, too: acknowledging the people and things in my life for which I’m grateful makes eminently clear the things for which I’m not. It’s how I ended up with a wardrobe consisting only of identical black, V-neck T’s: I just couldn’t muster up the gratitude for my other clothes, so I unburdened myself of them. I have fewer hobbies now and they’re collectively more fulfilling, and I have meaningful relationships with the most amazing friends in the world, but only a few superficial acquaintances. I’ve found gratitude to be a great equalizer, revealing truths of which I was previously unaware.
Spoiler alert: you’re getting married in a couple years. And I couldn’t plan five million weddings and not share some advice about yours. But I’ll keep it simple, so you don’t forget:
First, don’t argue with the moms. It’s their party, too. Look, I know. I know. Just shut up and trust me on this one.
Secondly, your wedding is going to be perfect despite the awkwardly short the ceremony, the disappearing photographer, the mosquito attack, or the band’s long breaks. So just bask in the love of your friends and family, and enjoy the best party of your life.
Tomorrow, and every tomorrow after that, is going to be amazing. Just roll with it, buddy.
There’s a ton more — like reading more poetry, pushing yourself harder at rock climbing, and not sending emails drunk or after 9pm — but I’m out of time and way out of room. So I’ll let Yesterday Chris figure out the rest on his own — I have on good authority it works out pretty well either way.
Thanks for reading, and best of luck to you.