Valley of Doubt
On nonlinear growth in startups.
Startups are weird places, and the roles within them are often ill-defined and porous. For me, this weirdness isn’t a turnoff; it’s the reason I prefer working in startups to more calcified environments. I don’t want to be a corporate peon, one of hundreds of Google or Apple communicators climbing a preordained ladder of titles. I want to be a part of building something. I want my contribution to matter, for things to break if I don’t do my job well.
Basically, I’m bought the fuck into the idea of nonlinear growth that startups promise.
A box? I don’t know her.
During my first few months at a startup, I got to work across a ton of cool projects. I helped an executive prep for a major industry conference. I worked with our privacy team on our narrative around our government work. And for one particularly memorable two-month stretch, I flew to Copenhagen and Munich week after week to work on an overhaul of our website with our most senior leaders.
The hallowed promise of nonlinear growth was coming true!
Still, something nagged at me. I'd done some interesting things, sure. I'd managed to both impress and concern my parents one Friday by having a jet-lagged Manhattan dinner with them after flying back from Europe. “Sorry, I was working on a project with our CEO,” I said, feeling at once fabulous and out of my mind with exhaustion.
But I wasn't really sure what it all added up to. When friends asked what I did at the startup, they didn't want a laundry list of different projects; they wanted to know what I was in charge of, what I was responsible for, what I owned.
“So you do policy comms?” they’d ask, after I talked about writing a blog post about our government work.
“Not exactly....”
“Oh, you do internal comms,” another would say, after I talked about working on an update to our travel and expense policy.
“Well...”
Five months into this job, I heard myself saying to my then-manager, "I'm not having an existential crisis, but...."
I call this phase the Valley of Doubt. It’s the lull that hits after the first few months or weeks of excitement into a new startup job.
Because at first, startups just throw you into the fire. It’s overwhelming, but it also means you get to immediately add value. And that’s really exciting!
Maybe you get a blog post out the door, or manage your first ad campaign. Maybe you’re given little-to-no direction on something and are completely terrified, and then someone tells your boss you crushed it and you realize…you kind of did!
But eventually, you may also wonder what it all adds up to. You may see other people around you doing totally different things than you — things that seem higher impact, or higher visibility, or like a sexier bullet for a resume.
There isn't one way through the Valley of Doubt. Or if there is, I didn't find it; truthfully, I flailed a bit on my way out. So here are a few strategies I DON'T recommend, learned through sometimes-painful trial and error...
Muscling for ownership.
At first, I went for more breadth over more depth, popcorning around projects, looking for something I could really and truly own. I don’t recommend this strategy. For starters, my frame was wrong. Ownership is a tricky thing to measure. Startups are very decentralized, so there should be LOTS of opportunities for ownership, right? Surprise — paradoxically decentralization sometimes results in more owners of a thing, not fewer.
Even when there is a single owner of a thing, almost no one in a startup is just handed the reins. As a mentor once told me, sweat outlives mandates. You earn the creds by doing the work — often quietly, often thanklessly, often alongside others.
Put another way, adding value is the cause; ownership is the effect. (And even then, “ownership” may look different at startups than at other places.)
Try to model the crazy.
I’m not sure how common this is, but in my first year at a startup, I tried to decomp EVERYTHING. Oh, our Comms and Marketing function is a joint effort of a bunch of different teams? Well, let me try to map who does what and what our strategy is.
I’ve seen others do this to a less extreme extent, trying to map their new company onto their understanding of how normal companies function. Guess what? Every startup is different, and it’s going to break your mental models for org charts, division of labor, and more. Even if you come from another chaotic, lawless place (I did!).
Compare yourself to others.
It’s true: Comparison really is the thief of joy. That’s especially true in a startup, where there are as many paths for growth as there are employees.
In my first months at a startup, every time I started to form a semi-coherent idea of what I did, I’d look over and see a coworker crushing it on business development or adding tremendous value on product marketing. And then I’d feel like my blob of internal/privacy/recruiting/executive comms was not just unintelligible but less than.
To be clear, it’s not a bad thing to constantly reassess whether you’re doing the most impactful thing. But remember that your impact is the intersection of business needs and your own strengths. I don’t have my coworkers’ strengths. But I have my own, and my ability to add value depends on my ability to lean into them.
...and here are a few strategies I DO recommend for getting through the ole Valley of Death:
Love the questions.
I’m about to quote Rilke at you, which is basically the equivalent of hanging a Live Laugh Love sign at my desk. Bear with me. (Yes, I also like Peloton and Alison Roman, why do you ask?)
“Be patient toward all that is unsolved in your heart and to try to love the questions themselves like locked rooms and like books that are written in a very foreign tongue.”
Despite the #yearbookvibes, I think this quote captures the only real way to thrive in a startup. Love the questions. Live in them. Stew in them! Marinate in them!! (Should I not be watching Alison Roman videos as I write this?)
The same goes for the many, many paradoxes you’ll encounter working in startups. If you hear two things that seem contradictory, sit with that. There will be some truth in both perspectives.
First principles, not best practices.
There’s no faster way to get a startup employee to shut down than to (try to) implement a “best practice.” We’re allergic to them. We think our company is a special snowflake onto which you cannot possibly map the restrictive models of other, lesser companies.
Sometimes this is contrarians taking contrarianism to a ridiculous extreme. Still, it’s important to work backward from the actual problem at hand, with all its nuances, to a possible solution. It’s almost always useful to imagine defending your idea without using the logic of best practices. If your idea is only defensible because it’s “best practice,” it’s not actually defensible.
Best practices should be arrows in your quiver, not one-size-fits-all solutions.
Untreated, the Valley of Doubt can metastasize into the Valley of Death. (My theory is that when anyone quits in their first year or two at a startup, it's because they never really emerged from the Valley of Doubt.)
I don't say that to scare you; I say it to reinforce that these questions are both really fucking hard and really fucking important.
I hope this post provides at least the comfort that you are not alone in these doubts, and at most a few useful tips to help you succeed in the startup world.