1:1 career coaching
for the people in tech.

People Problems is coaching, support, and “work therapy” from veteran designer, founder, and manager Jay Fanelli. For modern workers at all levels of tech and creative fields: designers, engineers, product managers, researchers, marketers, recruiters, and more.

People Problems is 1:1 coaching for modern workers at all levels of tech and creative fields: designers, engineers, product managers, researchers, marketers, recruiters, and more.

Let's Chat, Our First Session Is Free Let's Chat, Our First Session Is Free Let's Chat, Our First Session Is Free Let's Chat, Our First Session Is Free Let's Chat, Our First Session Is Free Let's Chat, Our First Session Is Free Let's Chat, Our First Session Is Free Let's Chat, Our First Session Is Free

How we work together.

Our first session is free.

Not “free” with a sales pitch attached. Just free: a half-hour conversation, no obligation. We'll figure out together whether I'm someone who can help. If you walk away, no sweat. Book your free intro session today and let’s find out.

We talk whenever you need.

If you decide to work together, it's up to you how often we chat. Looking for a regular cadence? Quarterly, monthly, weekly...I can do all that. Just need help through a tough stretch or a specific situation like a promotion or performance season? I can do that too. You set the pace.

Pricing at your level.

$150/session for early-career, $250/session for mid-career, and $500/session for executives and above. Sessions are 50 minutes, booked at your convenience. If we end up talking regularly, I'm happy to negotiate a friendlier rate.

Work is broken.

Something is broken with work. Maybe you know exactly what it is. Maybe you can’t quite put your finger on it. Either way, it’s making you miserable, and nothing you’ve tried has made it better.

Your therapist is great, but they don't know what OKRs are. Your manager might be new, or overwhelmed, or gone in the last round of layoffs. Your family and friends love you but honestly they're a little tired of hearing about it. And the career advice on LinkedIn is either toxic positivity or dystopian panic, and none of it is actually useful. Who do you turn to?

What you need is someone who’s actually been in the room. Someone who understands the machine—the hiring criteria, the performance reviews, the reorgs, the internal politics, the nonstop change, the ratcheting pressure—and can help you see it clearly.

Hi, I’m Jay.

Hi, I’m Jay Fanelli. I’m a designer, founder, and manager. Nice to meet you. I started People Problems because, well, I’ve done a lot of stuff in the 25+ years I’ve been working. I’ve navigated the chaos of agency life, the pressure of startup life, and the politics of big tech. I’ve hired and managed dozens of people. I’ve quit jobs and I’ve been fired. I’ve been laid off and I’ve laid people off. I’ve left work to go back to school and I’ve left school to go back to work. I’ve bootstrapped businesses and raised VC money. I’ve made digital products and physical products and even started a couple restaurants.

My last stop was Duolingo, where I spent nearly 5 years as the company’s first-ever Design Manager, growing the team 6x and managing them through COVID, a successful IPO, and massive product and company growth. I also led product design for the Monetization area during Duolingo’s first 2+ years as a public company, during which revenue more than doubled. (Fun fact: I named Super Duolingo.)

Though my title at Duolingo was “Senior Design Manager,” I earned a reputation company-wide as something closer to “Work Therapist” or “Design Dad” or “The Manager You Wish You Had.”

People from all levels and all corners of the company sought my advice—designers, engineers, product managers, researchers, marketers, recruiters, junior, mid-level, and senior folks—not because I had all the answers, but because I could quickly put their experience into context, explain the invisible forces that act upon all of us in the workplace, and hopefully give them actionable advice. More than two years after leaving Duolingo, former colleagues are still calling. Let’s chat and see if I can help you.

Why you need a career coach.

You want to shift your mindset and get unstuck.
You want to get promoted, or you just got promoted and don’t know what to do now.
You’re prepping for your performance review, or you just got it and need to make sense of the feedback.
You want to switch roles, industries, or careers, or you want to go back to being an IC after managing.
You’ve been told you need to “build more resilience,” but you’re already at your breaking point.
You’ve been told you need to “have more impact,” but you don’t know how.
You’re being told to use AI in your job at the same time as you’re worrying about getting replaced by AI. AI, AI, AI.
You’re worried about getting crushed by late-stage capitalism.
Your therapist doesn’t know what OKRs or KPIs are, and you’re struggling connecting your therapy to the workplace.
Your job has become all metrics, shareholder value, and looking good for the next board meeting.
Your manager was cut in the last round of layoffs, or your manager is new, or drowning, or busy worrying about their own performance.
Someone “onboarded” you but never actually trained you.
You got feedback that doesn’t make sense and your manager can’t explain it.
You’re stuck in the same narrative at work and can’t figure out how to break out of it.
You’re trying to figure out if you should quit or stay.
You’re about to have a difficult conversation and need to think through how to handle it.
You’ve been at the same level for years and don’t know why you’re not advancing.
You just survived a layoff and now you’re doing three people’s jobs.
You’re supposed to “do more with less” and it’s breaking you.
You’re good at your job but terrible at the politics (and it’s holding you back).
You’re burnt out but can’t afford to quit.
You’re being PIP’d or managed out and need to figure out your next move.
The career advice on LinkedIn is either toxic positivity or dystopian panic and none of it is actually useful.
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Questions? Comments? Get in touch.