I Got a Seat at the Table and Failed. Twice.
The story of how I climbed, crashed, and learned the hard way what real leadership requires.
TL;DR:
- Twice, I was given a seat at the proverbial table.
- Trusted with leading strategic efforts at a multi-million-dollar company the first time.
- Trusted with an entire UX org the second.
- Both times — I blew it.
Why?
- Not because I wasn’t capable.
- But because I was unprepared, prideful, impatient — and unwilling to grow through the friction.
- The first time, I was green.
- The second, I was worn out.
- Both times, I made it about me.
This is a story about:
- Leadership.
- Failure.
- And the hard lessons you won’t find in books or conference talks.
It’s about the cost of unchecked expectations — and what it really takes to stay at the table once you finally get there.
The Seat
Everyone wants the seat. The figurative table where strategy gets shaped, direction gets decided, and influence flows freely.
We fight to be seen.
We advocate.
We ask for the invite.
And when it finally comes? Some of us fumble it.
I know from experience.
This isn’t a post about theory. It’s not about “earning your voice” in some thinkpiece kind of way. It’s about the two moments in my career where I had the most influence, the biggest voice, and the most responsibility.
I’ve had a seat at the table before and since. But these two moments were different. The stakes were higher. The trust was deeper. And I’ve had to reckon with why it didn’t go the way it should have.
Not because I was forced out. Because I blew it.
So here’s the story. It’s a little messy. Super embarrassing. But it’s real. And if you’re aiming for the table, you should sit down and hear it.
The First Rise
Back in 2012, I was hired by as a UX practitioner at Covenant Eyes. Not a strategist. Not a manager. Not a leader. Just a hands-on designer trying to figure things out.
I touched everything:
- The CE Mac App
- MyAccount (Account management web app)
- Signup
- Marketing pages
- Support (Member support articles, videos, etc.)
- Reports
- Communities
- Anything that moved, clicked, or broke
For four years, I was a generalizing specialist – someone who knew enough to be dangerous in a lot of areas and halfway decent in a few others. I dabbled in everything, but leaned hard into a few core strengths.
UI design and visual design were my strongest areas. Right behind that were interaction design and information architecture. And I was quickly leveling up in strategy and user research.
But truthfully, I touched it all: content strategy, information design, usability testing, behavioral design, user psychology, writing — if it fell under the UX umbrella, I probably had my hands on it at some point.
I wasn’t just making things look good — I was learning how people think, how systems behave, and how design could bridge the gap.
And eventually, it clicked: I wasn’t just shipping screens — I was solving real problems.
Then I got the chance to overhaul our entire signup process — not just redesign it, redefine it.
I worked closely with Davin on this project — he extended a lot of trust, brought me into strategic conversations, and helped me grow through it. Together with leadership, we rethought how CE served families from the ground up: family accounts, family pricing, a unique sign up expereince for families, and smart defaults that actually made sense for real people with multiple users.
The result? A huge increase in acquisitions.
It was a win. A big one. And suddenly, I wasn’t just in the room — I was invited to lead the next big initiative.
I called it CEV2 — Covenant Eyes Version 2. A total transformation of the business, the product, and the model.
It introduced a clear customer focus shift, an image-based rating system powered by AI (yes, in 2016), and a modular, multi-platform app architecture. It prioritized behavior-change techniques and proposed deep integration of educational content and resources — all aimed at reshaping how we served individuals and families.
New features. New structure. New strategy. New everything.
I pitched it. Leadership bought in.
I got promoted. I got a team. I got a seat at the table.
But not just any team — this was a hand-picked crew of leaders from across the company. Marketing. Customer Service. Development. Product. And — a fantastic UX leader (and now a close friend) — was leading the UX side.
This wasn’t some scrappy little task force. This was a cross-functional dream team of experts and decision-makers from every corner of the org.
And me? I was at the helm — leading strategy and shaping the direction for all of it.
More than the title or the spotlight, I had something deeper: Real influence. A chance to make a meaningful difference. And I cared — deeply — about the mission of Covenant Eyes. This wasn’t just another project. It was a chance to help reshape the future of the company for the better.
It was everything I thought I wanted. The trust. The responsibility. The opportunity to lead something that mattered.
And I blew it.
The First Fumble
Let’s be clear: I didn’t fail because I didn’t care. I failed because I was underprepared, overwhelmed, and too proud to admit either.
Leadership believed in me. They saw potential — something in me I hadn’t even fully seen in myself. They gave me a shot. A real one. But I didn’t know where I needed to grow. I didn’t even know what my actual strengths were.
I was placed in a position where I could either rise or fall — and I fell. Hard.
At that point, I was five years into UX. Before that, I’d spent five years in graphic and web design. And now, here I was — leading a multi-million dollar transformation, sitting across from execs with decades of experience and actual decision-making authority.
I was not ready.
I was constantly frustrated. I couldn’t understand why people didn’t just do what I said. I was impatient. Impulsive. Prideful.
And I was territorial. There was someone on the team with some experience in strategy — someone I could’ve learned from. But I didn’t. I saw him as a threat, not a teammate. I guarded my turf. I clung to control. I let insecurity masquerade as leadership — and it cost me.
Every compromise felt like betrayal. Every delay felt like sabotage. And worst of all — I didn’t understand the business nearly as well as I thought I did.
I’ve learned to give some grace to the younger version of myself. I was 29, trying to lead through complexity while my brother was fighting cancer. Most days, I bounced between high-stakes meetings and hospital waiting rooms – carrying more than I knew how to hold.
I was in over my head. And it showed.
But in the end, none of that excuses what I did.
I gave up.
Not with maturity. Not with growth.
I didn’t say, “This is hard, but I’ll get better.”
I didn’t say, “This is hard, and I need help.”
I said, “This is hard, so I’m out.”
I walked away from the team I was leading.
I left strategy behind.
I went back to “just being a designer.” Not because I didn’t care — but because I didn’t want the pressure anymore.
I had been handed the ball on the goal line — and I just dropped it and walked off the field.
The Return
Less than a year later, it was clear: the company I left for was a sinking ship. I tried to stay — out of principle, out of loyalty. But by the time I looked around, most of the team had already jumped — including all the design leaders. The vision was gone. The structure was crumbling. And I was trying to hold it together in a place that had already let go.
To make it even heavier, my brother passed away during that season.
Grief. Instability. Exhaustion. It all hit at once. I was navigating loss and questioning everything I thought I wanted.
So I reached out to Davin — not for a job, just for a familiar voice. Someone who had believed in me when I barely believed in myself.
He listened — patiently, kindly. And then said something like, “Jon and I have been talking. We’re looking for a manager. You’d be a great fit — for the team, for the mission. And you won’t have to worry about strategy this time.”
No pressure. No grand vision. Just a steady role where I could lead, support, and rebuild — from a healthier place.
And honestly, it made sense. I’d been in management before. I’d always loved mentoring — guiding, developing, helping others grow. This wasn’t a step back. It was a better way forward. A way to serve the mission through a team — not just through myself.
So I said yes. This time, I wasn’t climbing. I wasn’t proving. I was ready to lead differently.
From day one, Jon and I were co-leading UX. There was no official director — just the two of us, each owning different parts of the org. We both reported directly to Davin.
And Davin didn’t just give us oversight — he helped us grow. He challenged us, coached us, and together, we shaped what UX leadership looked like at the company.
We laid the foundation — not just for the products, but for the people behind them. Design systems. Career frameworks. Skills assessments. Salary baselines. Budget planning. Hiring. All the behind-the-scenes work that turns a design team into a design organization.
Years passed, and CEV2 still hadn’t shipped. Aside from the AI-powered screen detection, most of it had been quietly shelved – lost in the shuffle of shifting priorities.
The vision was still alive. Just waiting.
The Second Rise
So here I was back at CE. Jon and I were co-leading UX. When I first returned to Covenant Eyes, I was part of leading the launch of Screen Accountability — the AI-powered screen detection that had been part of CEv2. It was a major shift, a major win, and something I was proud to apart of.
After that, the team kept growing.
The product got better.
Momentum returned.
Jon and I were co-leading UX. There was no official director — just the two of us, each holding down different parts of the org. And alongside us, Jason Walker was overseeing all of Communication Design.
Together, we were the three-headed monster of Design Leadership.
So here I was — back at Covenant Eyes. Jon and I were co-leading UX. There was no official director — just the two of us, each holding down different parts of the UX org. And alongside us, was overseeing all of Communication Design.
Together, we were the three-headed monster of Design Leadership.
It was far from polished. But it worked.
Over time, things began to shift. Davin was promoted again, and Nicole Morris stepped in as our new VP of Product. Under her leadership, Product became more clearly defined as a discipline — and UX, which sat within Product, started to feel that shift.
Sometimes we worked in parallel. Other times, we were expected to follow. The lines got blurrier, and the balance of influence started to shift. Titles shifted. Roles evolved. Mine changed two or three times during that stretch.
But through it all, we kept building.
One of the most important things I built during this time was something we’d never had before: a formal UX Strategy discipline.
Not just a buzzword or an aspirational concept — an actual function inside UX focused on upstream thinking and business alignment.
I brought in John Parkinson as our lead strategist — someone sharp, thoughtful, and relentless in his pursuit of clarity. And we paired him with Aaron Stites, a powerhouse researcher with a gift for uncovering what really matters.
Together, Strategy and Research became a single, integrated discipline — one that didn’t just validate ideas after the fact, but helped shape them before they ever reached the roadmap.
We created processes for evaluating ideas early — lightweight, structured, and rooted in evidence. We partnered more deeply with Product. We brought rigor to the front of the pipeline. We made UX not just a delivery arm — but a strategic driver.
Eventually, Jon moved on to new opportunities. And when he did, I took on full leadership of the UX org.
Design. Research. Strategy. I was overseeing the full experience — from first idea to final delivery. It was mine to steward.
Not because I played politics. Not because I chased titles. But because I kept showing up — consistently, imperfectly, relentlessly.
And somehow, I found myself in a bigger seat at the table again.
The Second Fumble
I wish I could say I nailed it. That I had learned everything from the first failure. That I came back stronger — led with humility, wisdom, and clarity — and crushed it.
But here’s the thing about pride: It doesn’t die easily. It just learns how to wear a nice blazer.
By this point, I was about four years into my second stint at Covenant Eyes. More experienced. More confident. But also more tired.
And pride doesn’t care how seasoned you are.
This time around, things were even less simple. A lot had changed over the past four years — mostly for the better. But change is hard. And we were feeling it — not just in UX, but across the board.
Product. UX. Strategy. Development. Marketing
The lines were blurry. The roles were unclear.
And we were wrestling with big, foundational questions:
What should we build?
Why are we building it?
How do all these pieces fit together?
There were disagreements. Dysfunction. Frustration from every angle.
And in the middle of it all, I felt powerless.
Even with the title. Even with the influence.
Even as the person overseeing UX, Research, and Strategy.
Ironically, it was the Strategy discipline I had built that started to shift things. As we deepened our research and tested ideas, we kept uncovering areas of opportunity — unmet needs, broken journeys, untapped potential. And one by one, those insights began pointing in a familiar direction.
They aligned — almost perfectly — with the vision behind CEV2. Not because we set out to revive it, but because the problems hadn’t changed — and the solutions we once imagined were still the right ones.
And this time? We weren’t alone. There was shared vision across the org — a growing alignment that this was the right direction.
We called it Victory.
It wasn’t a sequel. It wasn’t a reboot. It was mostly CEV2, reborn — smarter, sharper, more grounded, and trimmed down with room to grow.
And John Parkinson was taking point under me — leading with clarity, strategy, and relentless focus. He made sense of the chaos. He carried the vision. And he delivered.
And somehow — in spite of the dysfunction, the blurry roles, the tension between teams — we shipped it. Victory did what CEV2 never could: It launched. It stuck. It moved the company forward.
But even in that success, I was starting to come apart.
The work was moving forward, but I was running on empty. It felt like walking through mud — every step heavy, every win hard-fought. Progress came slowly, if at all. And over time, it stopped feeling like leadership and started feeling like survival.
It was exhausting.
It was discouraging.
And the truth is — I wasn’t strong enough.
The win with Victory felt both sweet and bitter. Yes, it launched. Yes, it moved the company forward. But deep down, I knew: we were five years behind where we should’ve been. We had finally reached a destination I’d seen years earlier — but we arrived late, worn down, and carrying the scars of everything it took to get there.
That truth was hard to swallow. And it made the success feel smaller than it should have.
So why did I fumble?
Pride? Most likely. Okay — yes. Absolutely.
Exhaustion? No question.
I had expectations — for how things ought to work.
For how my UX team should be structured.
For how research and strategy should be leveraged.
For the direction the company should be heading.
For how quickly things should change.
I had vision — but I didn’t fully respect the work, the patience, or the alignment it would take to bring that vision to life. I had expectations — for how things should work, how fast they should change, and how others should respond.
And when those expectations weren’t met, I didn’t adapt.
I got frustrated.
I got tired.
And eventually — I gave up.
I had an agenda. And when it didn’t play out the way I thought it should, I let that frustration simmer. I was doing the work of a director — without the title, the recognition, or the compensation. It wasn’t the reason I gave up — but it was the final straw. The quiet ache that made everything else feel heavier than it already was.
But in the end, none of that justifies what I did.
Because when things got hard, I didn’t press in — I pulled away. I abandoned my team. And in doing so, I made myself unworthy of the seat I had been trusted with.
Not all at once.
Not in a blaze of drama.
But slowly. Quietly. Emotionally. Gradually.
I let the weight of unmet expectations turn into resentment. I let my disappointment chip away at my leadership. And instead of fighting for clarity, or building the bridge, or doing what real leaders do…
I left.
Because that’s the truth behind this second fall:
It wasn’t the dysfunction.
It wasn’t the structure.
It wasn’t even the company.
It was me. I gave up. I failed.
What I Didn’t Know
Both times, I thought I was ready.
Both times, I believed I deserved to be heard.
Both times, I wanted control more than I wanted collaboration.
And both times, I missed the most important truth: The table is not about you. It’s not about being the smartest voice in the room. It’s about serving something bigger than your agenda.
It’s not where your ideas get built unchallenged — It’s where your ego gets tested in real time. Where influence doesn’t come from title or talent, but from the ability to align, adapt, and deliver — not just dream.
What I didn’t know then — but see more clearly now — is that leadership isn’t about being right. It’s about being ready when it counts.
So Learn From Me
If you’re fighting to get to the table — I get it. But if and when you get there?
Don’t make it about you.
Don’t confuse passion for wisdom.
Don’t walk out when it stops feeling good.
Stay.
Lead.
Build bridges.
Fight for clarity — not control.
If you get tired, don’t let it harden into burnout.
Rest. Step back. Take a breath. Take a vacation.
But don’t disappear.
Lead with vision — but hold it loosely.
Lead with confidence — but carry humility.
And lead through the friction — not around it.
Because the seat isn’t a reward. It’s a responsibility.
The table doesn’t need another hero. It doesn’t need another visionary. It needs someone who can stay steady when it gets messy.
I wasn’t that person.
Not the first time.
Not the second.
But I can tell you this: if I ever get this kind of seat again — I won’t waste it. The real question is… will you?
