1:1 Coaching
Six sessions that change how you see yourself -
and how others see you.
Deep 1:1 coaching for designers and tech professionals navigating a transition. We do the inner work and the outer work together, because one without the other doesn't hold.
The approach
Most coaching fixes the resume. We start somewhere else.
I spent 20+ years leading design teams and sitting in hiring rooms. I watched talented people get passed over - not because the work was weak, but because they couldn't articulate who they were becoming. You can optimize a resume in an afternoon. But if you don't know what you want, every bullet point is a guess. If you don't trust yourself, every interview is a performance. So we start with the identity work. The positioning follows.
The outer work
Strategy
- Portfolio critique and positioning strategy
- Resume and LinkedIn, rebuilt around who you're becoming
- Interview prep grounded in self-trust, not rehearsed answers
- Narrative work: how you talk about your career, your gaps, your pivot
The inner work
Coaching
- Values clarification: what actually matters to you, not what should
- Naming the saboteur voices keeping you stuck
- Connecting to the part of you that already knows what to do
- Building the self-trust to act from clarity instead of fear
Where people get stuck
Three places people get stuck.
Almost everyone who comes to me is stuck in one of three places. Knowing which one changes everything about what to do next.
01
Clarity
You don't actually know what you want next. Not what you should want - what would energize you. If I asked you to describe your ideal next role in two sentences, could you? Most people can't. Every decision downstream of that is a guess.
02
Confidence
You know what you want, but there's a voice in your head with opinions about whether you deserve it. "Who am I to call myself a leader." "I haven't done enough yet." That voice is running the show, and no amount of portfolio polish quiets it.
03
Presentation
You're clear and you believe it - but the way you show up doesn't match. Your LinkedIn, your portfolio, how you talk about your work. It's telling the story of who you were, not who you're becoming.
On a free call, figuring out which of these is yours takes about ten minutes. That alone is usually worth the call.
The path
What the six sessions look like.
Every engagement follows the same arc, because the order matters. Clarity first, then the inner work, then the positioning. Skip a step and the next one doesn't hold.
Sessions 1 & 2
Get Clear
Looking at what energizes you, what's been draining you, and identifying your path.
- Values work and what actually fulfills you
- Honest audit of what's working and what isn't
- Define what you want - not what you think you should
Sessions 3 & 4
Go Deeper
See where you are on the path, and bring back the self-trust.
- Identify the saboteur voices keeping you stuck
- Connect to your Inner Leader - the part that already knows
- Build the self-trust to act from clarity, not fear
Sessions 5 & 6
Navigate What's Next
Learn how to tell your story. Start positioning yourself as who you want to be.
- High-stakes decisions with tools to hear your own signal
- Closing the gap between who you are and how you show up
- Leave with a clear direction and the confidence to own it
How I'll support you
What's included in every engagement.
6 x 60-min coaching sessions
Deep 1:1 work where we get to the real stuff, not just the surface problem.
2 async deep-dive reviews
Real feedback on your portfolio, resume, or LinkedIn - not a checklist.
Between-session email support
For when you're spiralling or need a reality check.
Homework
To deepen the work and keep momentum between sessions. Inquiry, not busywork.
A complete engagement, start to finish
From alignment to agency
Sarah - not her real name, details adjusted - came to me with over a decade in UX and design operations and a pattern she'd been living for five years: every role started strong, and within months she was pursuing something the role couldn't give her. She was analytical, results-driven, and exhausted in a way she'd stopped mentioning to anyone.
Here's what made her interesting: she could articulate her own patterns with total precision. She could name the problem without feeling it. Her self-awareness had become armor.
In our first sessions, we found the structure underneath. Her professional standards - the thing she was proudest of - were doing two jobs. They protected quality, and they protected her. If the standards were high enough, disappointment could be predicted and controlled. She'd built an identity where output came first and the human stuff was optional, and she hadn't noticed.
The middle of the engagement was saboteur work. She named her inner critic - precise, disappointed, certain nothing would ever be good enough - and discovered it wasn't an enemy. It was a frightened protector. That reframe ended the internal war and made room for the other voice, the curious one, the one that already knew what she wanted to do and hadn't been allowed to say it out loud.
By session four, she said it: financial planning. Not my idea - I'd have never suggested it. By the time she said it in a session, she'd already started building a personal finance tool and cold-messaging people in the field. The coaching didn't give her the answer. It created the conditions where she could stop overriding her own.
She closed the engagement having left design, secured a mentor, completed six informational interviews, and mapped her certification path. Her words: from "foggy and lost" to "energetic tired with a destination." From "I hate myself when I'm not delivering value" to "I bring perspective, curiosity, and depth. That alone has value."
And here's the honest part: not everything resolved. She's in a season of delayed gratification - studying, logging hours, waiting. The worth-equals-output voice still shows up. We do monthly check-ins. The work isn't a finished product and I won't sell it as one.
One more thing, because you're probably a designer reading this: yes, she left the field. Most of my clients don't. The point was never the destination - it's that she stopped guessing.
What people say
Chris was very insightful. He started the session by asking questions to better understand my situation, and gave me advice tailored to what I'm looking for. He told the possibilities of different paths I could take in my career, and gave me some recommendations on what I can do next.
Chris was very insightful and had an interesting perspective on the industry. He's been helping me through a difficult market, and I always value his thoughts!
When I was chatting with Chris about the problems I was facing, he was extremely helpful in guiding my next steps and how to approach presenting my work and how to better lean on my strengths!
I've had a few sessions with Chris and will definitely continue booking more - each session has been incredibly productive and encouraging. Chris not only shares valuable insights about the industry, but also provides consistent feedback and support throughout.
One of these is enough.
Who this is for
Mid-career and at a crossroads
5-15 years in, and the path that made sense at the start doesn't anymore. You're not early-career lost - you're later-career stuck.
You want a real shift
Not a better CV. A different relationship with your work, your ambition, and how you show up for both.
Ready for the inner work
You're willing to look at the patterns underneath - not just optimize the surface. You suspect the block isn't tactical.
Passed over and can't figure out why
The work is strong. The promotions and senior roles aren't coming. Something in how you're showing up - or being seen - isn't landing.
Navigating a real transition
Layoff, pivot, burnout, or a role that stopped fitting. The uncertainty goes deeper than just finding the next job.
Who this isn't for
This probably isn't the right fit if you want someone to hand you the answers, you're looking for a quick fix, or you're not quite ready to question some of what you think you know about yourself. If you mainly need tactical feedback on your portfolio or resume, start with mentorship instead.
Investment
1:1 engagements start from $1,500 and range to $3,000+ depending on scope and structure. Payment plans available. We'll land on the right structure together on the call - that's part of what the call is for.
Frequently Asked Questions
How much time does this take?
One hour a week for the sessions, plus homework between them. The homework is inquiry, not busywork - most of it happens while you're walking the dog. If you don't have an hour a week for the thing that's keeping you stuck, that's probably part of what we'd talk about.
How do the sessions actually work?
Over video, an hour a week. I work across time zones - most of my clients aren't in my city, and plenty aren't in my country. Between sessions you've got email access and a piece of homework built to keep the thread going, not to grade you.
Is this coaching or therapy?
Coaching, not therapy. Therapy mostly looks backward - healing what happened. Coaching looks forward - what you want, and what's in the way of going after it. The premise I work from is that you're not broken and don't need fixing. You're capable and a little stuck, and my job is to help you hear your own signal. If something comes up that's better served by a therapist, I'll say so. The two sit well alongside each other.
What are your qualifications?
Twenty-plus years in design leadership - Director of Design and Design Operations roles at companies like Wayfair, Interac, and Wattpad - plus CTI training in the Co-Active model and Top 1% mentor status on ADPList. The short version: I've run the hiring loops you're walking into, and I've made the same transition I'm helping you make.
I've done coaching before and it didn't stick.
Ask yourself what kind it was. Most career coaching is tactical - fix the resume, rehearse the interview. That work matters, but it doesn't hold if you haven't done the identity work first. If your last coach skipped that part, that's likely why it didn't stick.
Can I just get help with my portfolio?
Yes - that's what mentorship is for, and it's a fine place to start. Some people do the tactical work first and come back for the deeper work later. See mentorship options →
What if the investment is a stretch right now?
Engagements start at $1,500, and there are payment plans - we sort out the structure on the call. Worth naming the other side of it, though: every month spent stuck carries a cost that never shows up on an invoice. Energy, confidence, time you don't get back. If money is the thing standing between you and doing this work, say that on the call. I'd rather find a structure that works than have cost be the reason you stay where you are.
Can my employer cover the cost?
Often, yes. A lot of companies have professional development or L&D budgets that cover exactly this, and most people don't think to ask. I can put together an invoice or a short proposal you can take to your manager. If that's a route you want to explore, raise it on the call and I'll make the paperwork easy.
I'm between jobs. Is now even the right time?
Often it's exactly the right time. A layoff or a forced pause is when the clarity work matters most, even though it's the moment money feels tightest. I keep some flexibility for people navigating a transition without a safety net - not as charity, but because that's frequently when the work does the most. If that's where you are, tell me honestly on the call and we'll see what's possible.
What if it doesn't work?
Fair question. Here's how I think about it: the work only doesn't work if you don't show up for it. Do the sessions, do the homework, bring your real stuff to the table, and something shifts - I've seen it too many times for it to be a coincidence. And I'll be honest with you in both directions. If partway through I don't think I'm the right person for what you need, I'll tell you. I'm not interested in coaching you just to keep coaching you.
What happens after the six sessions?
You leave with direction, positioning, and tools to keep working with on your own. Many clients move to monthly check-ins. Some come back when the next transition hits. There's no upsell treadmill - the engagement is designed to make you not need me.
How do I know if I need coaching or mentorship?
Ten minutes into a free call, you'll know. Roughly: if the problem is how your work is presented, mentorship. If the problem is that you're not sure what you want or don't trust yourself to go get it, coaching.
Not ready for the deep engagement? If you mainly need sharp eyes on your portfolio, resume, or interview prep, mentorship is the tactical slice of this →
Ready to figure out what's actually in the way?30 minutes. A real
conversation.
My calendar is open. Let's figure out where you're stuck.
My calendar is open. Let's talk.Or email me directly if that feels easier.