My company InVision is a sponsor of Within, a unique retreat for women in senior design roles. Which is how I found myself, like Charlie Bucket with his golden ticket, headed to Palm Springs recently for an adventure with 60 other women in design.

Despite many years in the field, this would be my first time in a large gathering comprised exclusively of women peers. I didn’t know what to expect, and the agenda only hinted at what was to come. Exploring leadership values, discussions about authenticity, resilience, and belonging. Group coaching. Hikes, yoga, meditation. I had high expectations for networking, for digging into some nagging professional questions, and for recouping some energy that’s been lost in the daily grind.

On the bumpy flight into Palm Springs, as my stomach rose and fell, I knew something interesting was about to happen. I just wasn’t sure what.

Career

Here’s the deal. I am forty-one years old. I have been in this field in one form or another for twenty years. I have had stints in seven different companies, both agency and in-house, as well as time as a sole proprietor. Along the way, I’ve been an engineer, a designer, a researcher, a strategist, an analyst, and a writer. I’ve led large, strategic projects for many companies. I’ve published my work (including a book), I’ve given countless talks at conferences, and I’ve taught dozens of workshops.

And yet, despite much professional good fortune, I sometimes feel kind of stuck. I’ve never been a formal manager. I only added the title of director for the first time last year. I frequently encounter people who say that my book or one of my workshops helped them when they were just starting out — and these people have more senior titles and more responsibility than me.

I did have a chance to start managing early in my career, with oversight of one team member. I was so nervous about meeting expectations and so untrained in how to coach others that I ended up crushing her with high expectations and terrible guidance. To her credit, she quit.

If you’re reading this, I’m sorry Jocelyn.

While I’ve led big efforts, I remain, basically, a high performing individual contributor. Through it all, I’ve watched people who were my peers early on take off in their careers, now VPs or heads of design in big organizations with big teams.

This is what I’ve come to this retreat hoping to learn: how to get my career unstuck — or at least clarity on why it feels stuck — when others around me seem to be on a rocket ship.

Belonging

As I approach the hotel for the retreat, I realize that I’m anxious. More anxiety as I walk into the opening dinner. A patio full of women seem accomplished and easy with each other. Over a meal, I speak with a woman who leads a big team of 100+ designers. Talking with her, I felt distinctly the difference between people who have big jobs versus me. Later, I meet another woman who is head of a new business unit in her company after leading design teams for 20 years. She’s seriously impressive. She’s conscious of the sexism that she encounters in her work (e.g. men assuming she is the assistant of a man who reports to her) but seems too busy getting work done to give it much pause. I walked away from my conversations with these women feeling, I’ll admit, like a bit of a fraud.

Conveniently built into the program is a panel discussion about belonging, with panelists from Google, Auttomatic, and Salesforce. Right away the conversation goes somewhere tangled and important.

The first question is “can you recall a time when you felt belonging?”

One woman talked about her experience with breast cancer, and the love and support she got from other women. And I thought, uh oh, what’s my belonging story? Do I ever really feel belonging? Another test that I have failed: being the kind of person who achieves meaningful belonging.

But the next woman to speak debunks the whole sham premise, admitting that she’s never really felt belonging and these days she just tries to belong to herself. After her, another woman shares her thoughts: belonging is by its nature a binary concept. She conceded that there are a few versions of herself that aren’t always in communication, and they’re not even in agreement about what it means to belong.

I can relate to this idea, that there are different parts of yourself, and they have different ideas, definitions and goals about belonging, some in conflict.

For instance, a significant factor in my career has been having kids.

I have a six year old and a two year old, two amazing little people. Over the past seven years — prime earning and career growth years, basically most of my 30s — I’ve spent about three years pregnant, on leave, or under-employed to accommodate child rearing. I’ve changed and selected jobs three times to better fit my role as a mom. (Admittedly, even having that option is a luxury that I cannot and do not take for granted.) Over these years, I have deconstructed and reconstructed my personal parameters for a productive work day to include hard bookends with complex handoffs of two highly dependent human beings to or from other people.

I’m able to be at this retreat because my husband is home taking care of our kids. But he’s not particularly happy about it, and neither are our kids. Being here, working on my professional belonging, puts a definite strain on my belonging in my family. And if I’m honest, even belonging in this community of women still feels elusive and unattainable, even though I am here, at this privileged event in a privileged field.

Speaking of my kids, I go back to my hotel room to FaceTime them. My six year old son is completely disinterested, off playing with legos. My two year old daughter holds the phone into her face and chats about Daniel Tiger and going potty. But soon she becomes weepy and upset. She keeps repeating “mama sit with me” as she wails into the phone. My husband finally comes and picks her up and takes the phone away from her and abruptly hangs up on me. That’s the first and last time I see them while I’m at Within. My husband makes the executive call that it’s simpler not to attempt it.

After that, I felt really rotten. Stuck in an in-between place where I feel bad about who I am at work and also guilty, inadequate, negligent at home.

So I went for a swim.

I floated on my back, sealed my ears with water, and looked up at the blue sky. At the end of the first full day, despite all my expectations that this would be an uplifting and transformative experience, it seems to have tapped into a well of sadness.

It sinks in that it’s possible to be both extremely fortunate professionally, and yet scraped raw from what it took to get there.

Values

The program includes a group writing activity about our personal values as a leader. I find myself writing about wanting to work with other people, be a reliable leader, and basically bust through all the gunk that I feel prevents me from advancing my career. It all seems true in the moment, but afterwards I realize it’s all stuff that I feel I ought to do — not necessarily what I really value.

When it comes down to it, I guess I value things that inherently keep me a little apart from other people: I value my inner life, I value my independence, I value getting to be curious about questions and follow them perhaps too deeply to bring others along with me at times.

On the second day of Within, we went for a hike that ended, fittingly, in a place called seven sisters falls. As a Barnard alum, this felt like a special omen.

As I prepared for this trip, I saw that there was a hike, followed by a pool party, in the agenda. I felt guilty. I would be leaving work and my family behind for these fun things that I could only describe as indulgences. But once we started hiking, the genius of the programming revealed itself. I suddenly understood that the hike and the pool party and the indulgences are the real programming, the real networking, the reason you come here. For while we hiked, we shared stories, and perspectives, and advice. We all marched along, lost in conversation, occasionally looking up to see the pretty vistas: desert covered in yellow wildflowers, lone cactuses in the middle of scrubby fields. As we walked single file, women shifted up and down the line, and conversations naturally shifted too.

The trail ended in a dusty, sun-baked spot beside a stream. Everyone stopped and looked around. It seemed anti-climactic. But then I decided to get my feet wet. I took off my shoes and waded in, the first one. Then I waded further upstream. A large boulder blocked the stream, making it hard to get any further. I tried to climb up it but it was slippery with moss. Another woman wanted to try, so I offered to give her a boost, which got her up the rock. Then someone offered to boost me. I tried again, and failed. I watched on as another woman tackled it like bouldering, looking for the cracks and bumps to dig her fingers and toes into. She succeeded. I tried her method, and I succeeded too. Several of us persevered further upstream and lo and behold: a waterfall, thundering into a little pool. We dunked ourselves. The sound and the rhythms and the shivers after bobbing back up felt baptismal. It was the perfect metaphor for who I hope I am professionally: when the trail seems to have ended, I’d like to think that I don’t sit around panting in the dusty sun. Instead, I get into the water, help others get up the rock, seek the waterfall. There is joy and pride and camaraderie in all of that. Those are real values for me.

We came back to a pool party. What a brilliant touch. There’s just something about soaking in the water, lazing, quietly chatting, that makes time stretch out and so effortlessly meanders between light stuff and hard-to-get-to-but-what-really-matters stuff.

Time

Time comes up obliquely in many ways at the retreat. I realize that for women in our field, time is both a liability and an asset. The big success stories of women at the retreat seemed to come from those who had put in the time in one organization. Several talked about what they’ve been able to accomplish in their companies because they’ve been there for a while. One said, “after 5 years you have a pretty good idea of what you can get away with in a company. After 10 years, you know exactly what you can get away with.” And yet, paradoxically, two separate women told me that the best things in their careers happened after they got pissed off enough to quit.

If I reflect on my own career, I fear I haven’t used time well.

The longest I ever stayed in one spot was four years. Rather than ask for promotions, I’ve moved around. As the scope of my work has grown, I’ve mostly just learned to pack more in. What’s my secret? Sleep. I steal from sleep. If you have encountered anything I’ve produced for public consumption, odds are good it was produced in the hours between 12am and 4am. It’s how I’ve been able to get a lot done in my career. I didn’t mind when I was younger — I even relished the feeling of flow. But I’m older now and the midnight hours come at a cost to my family. As a strategy for doing quality work, it’s debatable. As a strategy for scaling your work, it’s a dead end.

Another thing that comes up a few times in the conversation: many senior women in this career face a crisis around 50 — not sure what kind of work they’ll be able to do next, feeling like they have to pivot outside of design. It didn’t occur, or seem likely, to anyone that they could just keep moving up the ladder. This should trigger alarm bells for executives at companies that claim to want to be “design led” or “design influenced” or even just “design capable.” Mid-career women leaders in design — professionals with the experience and expertise to create customer-centric, desirable products — don’t see a growth path in many companies, maybe yours.

Growth

On the last day of the retreat, we did coaching circles. The organizers spent a bit of time explaining the principles of coaching: the premise is that everyone has the potential and resources to solve her own problems. To help you explore your challenge, you share your issue, and others listen, and ask thoughtful questions. (There’s also a little time set aside to offer advice.)

This felt like my moment to finally dig into the questions that I came here with.

How do I advance my career, grow a team, get past my blockage about being not just an informal leader but also a formal manager?

When it was my turn to be coached, I talked about having acceptance and success professionally but feeling like I haven’t achieved the obvious thing, which is to be a big manager. I talked about looking around and seeing so many people — so many men, let’s be honest — who don’t seem better than me, who have achieved that, and feeling confused and frustrated by it. I talked about knowing that if I’m going to manage, I’ll need to be more accessible and less crushing in my standards of others. But I also talked about my anxiety and ambivalence about letting other people in. I talked about my interest in the big ideas, and how making sense of big questions gives me energy. I talked about the waterfall. I talked about wanting to have the support and the ability to explore bigger things together with people that I can trust, and also how important it is for me to be inspired and drawn toward the big ideas of others.

That last part was an important revelation for me: it’s not just about finding my power by looking down (at the people I might manage) but also about finding my power by looking up and around (to the people who might inspire and motivate me). My coaching circle asked me what my intuition tells me. My intuition said that none of that is as far away as it seems, and it’s probably just a matter of making small adjustments, to which my coaching circle nodded in agreement.

When the time came to give advice, what my circle said surprised me. All around the table, like a Greek chorus, they said that I’ve got to stop comparing myself to others. Comparing my successes to those of men around me. My version of success doesn’t have to look like other people’s. I have conflicting feelings about this. Why not compare myself to men? They’re the standard, and it seems unfair that if my work exceeds the standards, my career should be anything less.

Recently, I have begun to wonder whether, despite few incidents of overt sexism in my career, the shape of my career is a woman’s career. Would it be different if I were a man? Or non-binary? Or non-white? Or disabled? Of course it would. It’s not a question of if, but how. And while these realities are vital to question systemically, the advice of my coaching circle makes me consider that on a personal level — whether it’s unfair or not, whether I am privileged or disadvantaged — that’s all beside the point. My career simply is what it is. And the reality is that my career and my life are far from compromised. They’re full, and interesting, and overflowing with kindness and good will. They just look different than the path well trodden.

My coaching circle also said that it’s ok to try and fail. And that I’m great already, no matter what happens. And hearing this gave me all the feelings, some that are complex and sad but also some that are happy and light and hopeful.

The last session was a panel/group discussion about resilience with panelists from LinkedIn, InVision (holla), and Spotify. The big impression for me was how important it is, especially if you’re a manager or leader, to care for the mental health and whole heart of the people you work with. Needless to say, it’s also important to take care of yourself, and make sure you’re not constantly operating from a depleted place.

To quote Her Majesty Lizzo, “if I’m shiny, everybody gonna shine.”

It made me think about my husband and my kids. They’re my real team. If I am to be a manager of anything, I have to start with them, which is to say, caring for their health and whole hearts.

Dreams

I’ll end with this. I had strange dreams while I was there. In my dreams, I was back in my real life, but I kept encountering people from the retreat. I visited one of the more senior women at the retreat in her office. She was in charge, but she was also the receptionist. I visited another in her office, and found myself taking out the trash, as people piled more trash next to the garbage can. I ran into another woman from the retreat and she told me that she had just been laid off. And then in my dream I realized, oh hey, you’re still at the retreat. You get to go back there, where none of this shit is happening. And I felt relieved to wake up and return to this soft, brief paradise, which felt like a truer reality.

What does it all mean?

The day to day truth for women in design isn’t always glamorous. Imposter syndrome, inequity, and the practicalities of our private lives are a noxious brew that makes a hard job harder. But we’re not alone. As a collective force, we make each other stronger, we make our teams stronger, and we make the work stronger — whether we’re conscious of it or not.

Thank you Within and InVision for opening my eyes to that.

I am joining InVision as a Director of Design Education, working with the esteemed Aarron Walter, whose work I have admired for years.

Why the change?

In a sense, it’s not a change but a continuation. My career has been devoted to design. First, doing it. And in more recent years, trying to understand and help establish the case for why doing it is a good thing. In that time I have looked at the design space from many different angles. My book The User Experience Team of One was an attempt to provide tools and moral support for individual design practitioners. More recently, I have sought to understand design’s contributions at a macro level, analyzing the state of the design field more broadly.

Throughout all this, one company has caught my attention again and again. It’s InVision. I have been an eager fan of Clark Valberg’s cheeky emails hitting my inbox every week with great design tips and case studies. I was inspired when InVision brought the documentary Design Disruptors to the world — and then put it on the pedestal that it deserved, screening at swanky movie theaters like San Francisco’s Castro Theater. And by creating and sharing best practices through projects like DesignBetter.co and the Design Genome Project, it’s clear that InVision is earnestly working to create a deep body of knowledge that can be a resource for everyone who wants to do better design.

So when Aarron Walter said, “Hey, let’s talk about how we could maybe work together more,” I was interested. Aarron’s team, at its heart, is about researching and sharing the stories of amazing design-forward companies in order to advance our whole community through shared knowledge. That’s exactly what I’m about, too. And now, with Aarron and the rest of the Design Education team, I’m doing it at InVision.

There’s also a selfish reason I am joining InVision.

It’s because I think they’re on to something really smart. My time as an analyst at Forrester opened my eyes to the massive software platforms that are available for the marketing and tech communities. It also highlighted for me how the design tooling landscape, for the most part, is still a rogues’ gallery of point solutions and up-and-comers. But it won’t be forever. With the growing importance of design in business, and the expansion of design processes throughout organizations, integrated design platforms that properly support how organizations work are inevitable.

InVision’s evolution of its product suite and its smart acquisitions have made it clear that Clark and team think about the design process not in terms of point solutions but platforms. They understand that design isn’t a discrete activity walled off in a single software program. It’s a dynamic, organic, sometimes messy collaboration that mobilizes a whole organization (and its customers too, when done right). InVision is moving far beyond its origins as a prototyping tool, and I want a front-row seat. Put me in coach, I’m ready to play. That’s a horse I want to bet on. [Please supply your own bad sporting analogy.]

In short, InVision believes in design’s future, and I believe in InVision’s future.

Here’s what this means for you, friend of design.

I will be continuing to research, synthesize and share how the best of the best are doing design. If you think that there’s a gap out there in our collective knowledge about how to do great design, please call my attention to it. That will help me and the rest of the Design Education team know where to focus our efforts to best help you in the design community.

The first two things I’ll be working on are further contributions to the Design Genome project, and an upcoming workshop in San Francisco on June 13 on communicating the value of design. (Come one, come all!)

Here’s where my head was at the time: I felt that I had seen how organizational dynamics affect design work both on the agency side and in-house. But I also sensed that my experiences were shaped by questions about the role of design that I not only could not answer, I could not even see.

I was simply too embedded within the system. Doing the daily work of experience design was an absorbing puzzle that sucked me in and consumed all my attention and made me forget to stop and step back and ask whether the puzzle was even worth solving. My vantage point was all projects and politics and the dulling comfort of daily routines, and that made it hard to fully see a movement in which I was a very active participant. Fish. Water. That old problem.

I found myself questioning whether the importance of UX, which I took for granted, had simply become a matter of faith in my professional echo chamber, or if people who really run the world (of business, at least) believed it, too. I wanted to challenge my own hyperbole. Test my own faith. I wanted to see what really mattered when it comes to experience design, what kind of results it produces, who really does it right.

So I went to Forrester to work as an analyst.

And Forrester did not disappoint.

There, I fielded research with hundreds of practitioners and service providers. I mined their data for industry-wide themes. I interviewed scores of user experience and customer experience professionals about their work. I mucked around in academic research. And best of all, I took questions from lots of companies. Lots. And lots. Of companies. I took hundreds of inquires from different organizations asking questions as basic “what is design thinking?” to those as complex as “what’s the future of mobile experience design for the hospitality industry?”

It was fascinating and educational and humbling. I learned so much.

Fast forward 18 months. I have decided to leave Forrester. Why? Partly for some personal reasons — too much travel, etc. But also, in a way, because of what I’ve learned. May I share?

Lesson 1—Companies Are Desperate For The Kind of Help That Designers Can Provide (But Many Don’t Know It)

What I learned at Forrester is that companies are deeply concerned that they need to improve their customer experience. (They do.) That they need to ready themselves for digital. (They do.) That they need to create a more customer-centric culture. (They do.) And there now streams forth a rush of potential advisors to help with this challenge. UX comes into this conversation sometimes — usually when organizations are trying to improve their digital customer experience — but in many cases, the management consultancies and advertising agencies and branding agencies and IT outsourcers and business systems integrators who are leading the conversation frame the challenge as something much, much bigger.

With so many people in the conversation—and some of them, frankly, much better at speaking in compelling business terms—the in-house UX teams and the specialized UX service providers are, too often, marginalized as mere UI design while the big work goes to the big kids.

Lesson 2—Design Drives Change and Value (No Duh, Right? But What A Relief To Confirm It)

I learned that the companies that have the kind of customer experience practices and digital readiness and customer-centric cultures that others envy take user experience seriously. They have high expectations for it and they dedicate resources that reflect that.

Indeed, what remains so interesting about the practice of UX is that, when done right, it is a locus of the kind of culture change, the kind of pro-customer operations, the kind of integrated digital thinking, that companies are trying to develop. It turns out that how a company approaches UX can have a pretty significant impact on how it readies itself for a host of other big challenges.

I also learned (re-learned? confirmed?) that experience design is absolutely an economic lever. At its most modest, it reduces engineering and maintenance costs by identifying requirements more accurately early on. It lowers support costs, because it makes it easier for people to self serve in digital channels. It drives desirable user behaviors that have direct financial impact and engender loyalty. And for companies with disruptive ambitions, it can help stake out new market opportunities in the experience gaps neglected by old-model industries.

Lesson 3—Still, Too Many Designers Suffer From Poor PR Of Their Own Making

But I also realized why I had needed to explore these questions more deeply in the first place — because designers, it turns out, are not so good at talking about the benefits of design. I am sorry to say it, but I found that UX people were often the least precise in explaining and conveying their own value. (Sorry boo, you know I love you.) Too many UX professionals still don’t have a clear and quantifiable explanation of the benefit of UX, still haven’t rationalized how their source of customer insights squares with the other kinds of customer-focused work that organizations do, and still approach UX in entirely too territorial a fashion. The people who told the story of design best? Often, it was marketers, channel managers, product managers, even operations folks.

UX practitioners desperately need to start absorbing, and then skillfully retelling, the kind of thinking that we’ve been seeing in John Maeda’s annual design in tech report, in the kind of writing coming from McKinsey Digital Labs—and hopefully in the kind of research that I did at Forrester.

Lesson 4—You Don’t Have To Be At An Analyst Firm To Take An Analytical View On Design

Above all, what I learned at Forrester is that insight about where an industry is headed isn’t locked up inside analyst firms. It’s distributed in the heads and experiences of all of you. The challenge is just how to gather and organize it. And wouldn’t it be progressive and communal if that kind of analysis could be shared as freely as we share insight about methods and techniques? No paywalls, no citations. Just our own information reflected back at us, a little more orderly. I think it’s possible.

So, I’m excited to share that I am officially hanging out my shingle. Open for business. Taking the leap.

My plan is to offer design consulting services to help organizations examine how effective their current experience design practices are, and work with them to make them stronger. But with a cherry on top. Because I really don’t want to stop doing analysis. I actually don’t think the UX field can afford to stop doing analysis. So, I’m not stopping. While I’ve decided to leave Forrester, I’m not leaving the pursuit of research and analysis on experience design.

But to do that, I need your help.

So — you saw this coming, right? — I am asking for your help in my first official post-Forrester research effort: a survey on the state of user experience in 2016.

(It asks questions about UX in your organization, and takes about 10 minutes to complete.)

My goal with this survey is to address several questions that we talk about a lot as a community but for which we lack good data. Questions like, where does (and should) UX it sit? What does (and should) it entail? What do we spend on it (and what should we)? And most important, what kind of benefits does great UX make possible?

I’ll be sharing the analysis openly; ETA is sometime this summer. And if you complete the survey, I’ll send you a copy of the raw data.

Lessons On Design From A Once And Future Analyst was originally published in Leading Design on Medium, where people are continuing the conversation by highlighting and responding to this story.