A conversation with Whitney Hess, on careers, whispers, and where to plant yourself
Photo by Bob Bowie on UnsplashSome questions sound administrative but are not, and “why do you want to switch jobs?” turns out to be one of them. I asked it on a mentoring call in the way you would ask about notice periods or portfolio order, one practical item among several, and the designer on my screen began to cry. Neither of us expected it. We sat with it for a moment, the way you do when a video call suddenly contains something real, and when she tried to answer, the answer had very little to do with jobs.
I brought this moment to Whitney Hess, who spent a decade as one of the most visible independent UX consultants of that era, based in New York for much of it with clients around the world, before consciously shifting her business from consulting to coaching, and who has therefore listened to more designers talk about their careers than almost anyone alive. She was not surprised. Long before people can say out loud that the work no longer fits, she told me, they hear it as a whisper: a quiet, dismissible sense that this is not what they want. The whisper is patient. Left unanswered it does not fade but grows, until one day it has become a daily shout, and a person finds herself crying on an ordinary mentoring call without quite knowing how she got there.
Whitney HessI have been interviewing designers who left the craft, or reshaped it into something new, for a book I am slowly writing about what is happening to our profession. Whitney is firmly in the second camp, and she will correct you if you suggest otherwise: she has never left UX, and she keeps her identity as a UX designer today. What she changed was the shape of the work, and she changed it while everything was still going up: the clients were blue-chip, the blog was widely read, the field itself was ascendant. That is what makes her worth listening to now. Most of us only examine what we really want when circumstances force the question, and she examined it voluntarily, at the height of a thriving practice, while the whisper was still at whisper volume. Since it is the quiet season, and half the industry is out of office with more time to think than usual, her story seems worth telling at length.
What the whisper actually says
Whitney’s move out of consulting was not a leap, and it did not begin with dissatisfaction. She registered her company in 2005, went fully independent about three years later, and built the kind of practice most designers would consider a destination: Scientific American, WNYC, the United States Holocaust Memorial Museum. The trouble, when it arrived, arrived inside the work rather than around it. “I wasn’t really addressing the systemic problems” she told me. A project would end, the deliverable would be good, and the organization that received it would remain exactly the organization it had been before. So she began pulling her clients’ own teams deeper into the work, partly for better outcomes and partly because, as she put it, it “felt weird not leaving the company in a better place.”
It is worth noticing what the whisper was actually saying, because it was not saying quit; it was saying something more precise. It was telling her which part of the work was hers: less the solving than the facilitating, less the deliverable than the people gathered around it. The signs were public long before she acted on them. In 2012 she wrote on her blog that her consulting role had become “kind of like that of a group-therapist,” which reads today like a diagnosis published in plain sight; within eight months of writing it she had enrolled in a yearlong coaching training. The certification did not change what she was. It caught up with what she had already become.
The biggest challenge is how you design your career.
The economics of listening
The economics deserve to be told plainly, because this is the part that career-change stories usually leave out, and because Whitney, it turns out, has crossed twice.
The first crossing was the raw one. In 2008, after three years of running her consulting business on the side, she left her full-time job to make it her whole livelihood, and the numbers underneath that decision were thin: about three months of savings, in New York, with no institutional net. “It was terrifying,” she told me, and she meant it concretely enough that she had decided she would work at Starbucks if that was what staying independent required. What she had instead of a cushion was a track record of a particular kind. “I’ve always trusted my ability to figure it out,” she said. “I knew I was going to be resourceful.” Designers will recognize that sentence, because it describes the psychological posture of every project we have ever started: a new domain, unclear requirements, stakeholders we have never met, and a working assumption that within a few weeks we will understand the problem better than the people who handed it to us. It is a strange kind of confidence, empirical rather than temperamental, assembled from having been dropped into the unknown many times and having found the shape of it each time. Whitney’s real innovation was pointing that confidence at her own livelihood.
The second crossing, into coaching in 2013 and 2014, looked nothing like the first, and the difference is the lesson. By then she had significantly more savings, and she kept taking UX consulting projects while the coaching practice ramped up, winding one income down as the other grew. The first crossing she survived on nerve; the second she designed. In time the coaching revenue found its footing, and the consulting decade turned out not to be a sunk cost at all. Those years were what allowed her to sit credibly across from the senior leaders she now coaches, which is to say the practice she wound down kept working for her inside the practice she built.
The people who arrive
It would be easy to file what Whitney does now under career services, and the label would miss most of it. People rarely bring a career to a coach because everything is fine, and the field she serves keeps producing a particular kind of trouble. It is full of accidental leaders, she observes: craft people promoted into managing others because that was the only ladder on offer, now spending their days in meetings, mourning the work their hands used to do. Designers at large, she has noticed, see themselves as problem solvers and business growers and are received as people who make nice things, and they extend endless empathy to their users and almost none to their own kind, or to themselves. “We take a lot of responsibility on our shoulders,” she said of her profession.
So the coaching rarely stays inside the career, because the career is rarely where the trouble actually lives. Her question for clients is not what the next role should be but something quieter and harder: what is their best self, and what would work look like if it were built around it? It is the same instinct that surfaced in her consulting days, the group-therapist tendency she once joked about on her blog, matured into the job itself. It also explains her list of interests better than any career-services framing could. A coach who follows her clients’ troubles all the way down will end up talking about money, about grief, about what remains when the title is gone, which is to say she ends up coaching a life, and the career only as the part of it that happens between nine and five.
In defence of detours
The part of our conversation I have thought about most came when I asked what is next for her. Instead of an answer about deepening the coaching practice, she gave me a list: she is interested in financial advising, in training as an end-of-life doula, and, she added with a smile, in private investigation.
The list sounds eccentric until you trace where each item comes from. The interest in finance grew out of twenty years of running her own business, and out of the money questions her clients keep carrying into sessions, since you cannot coach someone about their career for very long without talking about what the career is for. The doula interest grew out of grief. She lost a few people close to her in recent years, accompanying those endings at close range, and emerged knowing something she could offer other people in the hardest passage of their lives. Even the private investigator idea, the one that made us both laugh, is her day job wearing a trench coat: she is paid to read systems, incentives, and decision makers, and to notice what everyone in the room is leaving unsaid.
None of these are exits, in other words. They are continuations, experiences she already owns waiting for a context that wants them. Underneath them sits a view of careers that is quietly radical: a working life is not a ladder within one profession but a body of accumulated experience that can be recombined, more than once, into new work. “The decisions that we make now become the legacy that we leave,” she said at one point, and the word legacy is doing real work in that sentence. She thinks about careers on the scale of a whole life, endings included, which may be why becoming a doula does not strike her as a change of subject.
Held up to that light, your own history gets interesting quickly. The banking designer who has spent five years inside compliance reviews is, whether she thinks of it this way or not, becoming an expert in regulated systems. The design lead who has survived three reorganizations has learned things about organizations that consultants charge for. We rarely see this in ourselves, because we are looking at our job titles, and a job title is a summary written by someone else, for a purpose that was never ours.
Where you plant yourself
None of this means growth is purely a matter of will, and the sentence that gave this piece its title was about the limits of it. “You can’t grow roses in a cornfield” Whitney said. Your ability to grow depends to an uncomfortable degree on the environment you are planted in. A cornfield is not hostile; it is optimized for corn. An organization that understands design as decoration will not, through any effort of yours, come to understand it as systems thinking, and the career path available to you inside any company is a function of how mature its design practice is, rather than of what your ambition deserves. Careers, in her telling, transfer no better than components do. “You cannot design one widget and expect it to work in every app in the app store,” she said.
The biggest decision they need to make is where they plant themselves.
Her practical advice follows from the metaphor. “The biggest decision they need to make is where they plant themselves,” she said of the designers she coaches, and she talks about that decision the way people talk about buying property: “I wouldn’t buy a house without doing my research on the neighborhood.” Designers, meanwhile, routinely join companies knowing less about the design culture than they would insist on knowing about a place they were going to live. Who does design report to? What happened to the last three senior designers? Does the career ladder exist anywhere outside the recruiting deck, and has anyone actually climbed it? These are questions you can ask in an interview, and asking them tells the company something about you that works in your favor.
Speaking as someone who runs a design team inside a large bank, I can confirm the information is not hidden. People will tell you how design really lives in their organization, sometimes proudly, sometimes bitterly, usually within ten minutes. We run more discovery for a two-week feature than most of us run for a five-year employment decision, and there is no good reason for that asymmetry.
Running discovery on yourself
What I take from Whitney’s story, and what I would like to hand to the designer from my mentoring call and to everyone quietly carrying some version of her whisper, is not reassurance. The market is hard at the entry level, unstable in the middle, and strange at the top, and reassurance would be a kind of lie. What her story offers instead is a method, and it is one designers already practice daily on other people’s problems.
It begins with discovery, pointed inward. The research question is not which job titles you could plausibly get. It is which moments of the past five years felt like yours, and what people keep bringing to you that appears nowhere in your job description. Whitney’s whisper named the facilitator inside the problem solver. Yours is likely to be similarly specific, if you give it the kind of patient attention you would give a user interview.
It continues with an inventory. Somewhere in your history is experience that feels off-topic: the failed side business, the caregiving years, the community you moderate, the domain you absorbed by accident. On the ladder model of a career this is clutter. On Whitney’s model it is material, and some of it is closer to becoming work than you think.
Then comes the audit of the soil, which is the uncomfortable step, because it can return the finding that nothing is wrong with you while something is wrong with the field you are planted in. The move that follows is not necessarily out of design. Sometimes it is only out of the cornfield.
And then you prototype, cheaply and early, the way she did both times. The consulting business ran for three years on the side before she trusted it with her livelihood, and the coaching practice ramped up while consulting still paid the bills. The jumps were real, but each was the last step of a long prototype rather than the first step of a plan. Mentoring one person, taking one course, writing one essay: these are the paper prototypes of a next career, and they cost about as much as paper.
What holds it together is the kickoff feeling, that trained confidence in your own resourcefulness. It is not Whitney’s private gift. It belongs to the profession, built into all of us by every project that started in fog and ended in shipping. UX has always attracted people who want their work to mean something, and that appetite survives any particular job, which is exactly why it aches when the job stops feeding it.
A question for a slow afternoon
Near the end of our call Whitney said she wants to keep developing her skills “over the arc of my career,” and it was clear she meant the arc of a working life, forty-some years across however many professions those years turn out to contain. She likes variety, she told me: “I like having every day feel different.” “Life happens,” she reminded me. “All your life plans go out the window. Covid happens.” What survives is the why underneath, the boundaries you will not trade away, and a flexibility about nearly everything else, so that when an opening appears you are able to recognize it and move.
We need to be connected with our WHY.
I think about my mentee often. The tears were not a breakdown, as far as I can tell. They were information arriving, a whisper that had been ignored long enough to find another channel, and the kindest thing that moment did was make the question impossible to postpone any further.
So, in the spirit of the season, and with whatever slow afternoon you can find: what do you actually love doing? Not what you are good at, which is a different list, and not what pays, which is a third. If you trusted yourself the way you trust yourself at every kickoff, what would you scope first? Somewhere inside the job you have is the work you want, and finding it is not a leap of faith. It is a design problem, and you have been training for it your whole career.
Whitney Hess coaches creative leaders at whitneyhess.com. Her 2012 essay “Designing the Company, Not the Product” is where this story quietly begins.
This conversation is part of a series of interviews with designers who left the craft or reshaped it into something new, for a book in progress.
If the soil audit above left you wondering where you actually stand, I built a tool for that step: a free, scenario based self assessment, about ten minutes, and the output is a profile, not a grade. Treat it as a private room. You can take it at designlevel.io/assessment
And if you think I am wrong about any of this, tell me. The strongest corrections to my thinking have come from readers.
You can’t grow roses in a cornfield was originally published in UX Collective on Medium, where people are continuing the conversation by highlighting and responding to this story.