Four Lessons from Four Years as a Product Marketing Coach

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Four Lessons from Four Years as a Product Marketing Coach

Happy New Year, everyone!  I hope 2026 is off to a gentle, grounding start for you. 🥰

The end of a year/beginning of a new one always puts me in a reflective mood. It is one of the few moments when time feels slow enough to pause and really take stock. I think about what worked, what didn’t, what surprised me, and what I learned the hard way.

This year marks my fourth year running my own product marketing coaching and advisory business (or 5th year if you count my side-hustle year). It has been an incredible journey. There have been real highs, plenty of challenges, and constant learning. I feel deeply grateful that I get to wake up every day doing work I care about, working with thoughtful, driven people, and building something that supports my family. 

But that doesn’t mean it has been easy or linear. 

I’m sharing this reflection because I’m often asked how I started my business or how I built what I do today. From the outside, things can look smooth or “figured out.” The reality is a lot messier and slower. And to me, there’s nothing more encouraging than hearing how things went “behind the scenes” when people share their success stories. 

Because our career successes are not magic, and that means whatever you want to achieve, it can happen for you, too.  

So here we go. 

Lesson 1: Mastery beats motivation 

Many people are familiar with parts of my story, but for those who aren’t, here’s the short version. I started my career as a transportation engineering consultant and later made a hard pivot into product marketing. It was intense and challenging, but it worked. After becoming a newbie PMM, I was promoted three times in three years to become a Director of Product Marketing. 

After building several PMM teams from scratch, I decided to go out on my own.

I’m sure I looked confident from the outside – but I did not feel ready at all.

During COVID, I helped several laid-off friends land new jobs, and that’s when I started to notice that I was exceptionally good at helping people make sense of their experience and turn it into a clear, high-impact story. It was the same skill I had relied on to change my own career.

These friends pushed me to take the work more seriously, which eventually grew into my 1:1 coaching programs.

At some point, as my business grew, I wanted to reach more people, so I decided to build a job search course. I spent a huge amount of time on it, creating the curriculum, recording videos, and so on. But when I launched it, only five people signed up.

I remember feeling embarrassed and disappointed. I thought that the idea was never gonna work and pretty much gave up. But after sulking for a week, I decided I couldn’t quit yet.  I knew from plenty of people that my process worked…. So why didn't anyone sign up? 

Instead of giving up, I got curious. I paid close attention to those five people. Where did they get stuck? What actually helped? I also talked to people who had considered signing up but didn’t.

As I collected feedback, one insight immediately stood out: job search support cannot be purely self-paced. People need accountability, real examples, feedback, and community. That realization changed everything and helped me launch the PMM Job Search System in December 2024. 

Over the past year, more than 75 people have gone through the program, with an average of 1 person per week landing a new job. None of this would exist if I had treated those first five sign-ups as failures instead of information.

This was a huge lesson for me that I will carry forward: 

The most meaningful things rarely look impressive at the beginning. Mastery is built through repetition, humility, and a willingness to keep going.

Lesson 2: Clarity beats noise

When you are building anything, whether it’s a business or a career, it’s like rowing a boat. If you don’t know where you’re going, all that effort just moves you in circles.

Early on, I spent a lot of time thinking about what kind of business I actually wanted to build. I was raised by a single mom with very strong values, and I’ve always had to reconcile two things that can feel at odds: creating real value for people and being paid fairly for my work. I wanted to help people generously, but I also needed to support my family and build something sustainable.

What became clear to me quickly is that I didn’t want to build a business optimized purely for short-term revenue. I wanted something enduring: a business grounded in impact, trust, and long-term relationships. I believed that if I focused on that, the money would follow. Not the other way around.

That clarity made some decisions harder in the moment. I had to learn to turn away clients. I said no to opportunities that looked good on paper and ignored paths that promised faster growth but didn’t feel aligned with my true goals.

I see this tension most clearly on LinkedIn. There are moments when I spend days creating a post, only to watch it land with 20 likes. Then I see a meme rack up thousands of likes. I’d be lying if I said that never stung or made me question my approach. The comparison mentality is real. 

But I always come back to the same question: what am I actually trying to build?

That question has helped me ignore noise and focus on signals that matter more to me. Not just revenue growth, though that’s important. What I care most about are repeat clients and word of mouth. Those are indicators of trust and durability.

Last year, nearly 40% percent of my work came from repeat clients across my programs, along with a steady stream of referrals from people who know me and my work. Those results have given me a deeper kind of confidence that comes from knowing this: 

Sticking to my values will always lead to the right results.

Lesson 3: Focus, but leave room to experiment 

I’ve always believed deeply in focus. As product marketers, we know this instinctively. If you try to do everything, no one knows you for anything. Focus is what allows mastery to form.

For most of my career, I leaned very hard into that principle. And it served me well. What I learned more recently is that focus alone isn’t enough.

Over the past year, I started thinking about my work through an 80/20 lens. 80% of my time went into refining and deepening my core offerings. The remaining 20% I treated as R&D. This 20% was uncomfortable by design because I needed to put myself out there, to try things I wasn’t sure would work, and to be willing to face rejection. In a world that’s changing as fast as ours, doing only what has worked in the past is one of the fastest ways to become irrelevant.

And not surprisingly, about 90% of those experiments failed. I was ghosted after proposals. Conversations that felt promising went nowhere. Ideas I thought had potential turned out to have no real product-market fit. But those failures were incredibly informative. They taught me what not to pursue and sharpened my instincts.

The remaining 10% did surprise me. For instance, I helped an AI startup create their positioning and messaging for expansion into the US market, I trained a team of 70 PMs and PMMs to align on how to work together (yay!), and I built a recruiting agency! 

So by putting myself out there, I got opportunities that kept me sharp, exposed me to new problems and perspectives, and opened up new business ideas.

Lesson 4: Getting help > going at it alone 

One of the most important lessons I’ve learned is that growth gets much harder when you try to do it entirely on your own. Not because you don’t know what to do, but because the most meaningful problems require new perspectives and support.

I’m actually introverted, even though people often assume otherwise. Writing has always been my most natural way to connect, which is probably why you’re reading this newsletter. 😀 But introversion can also turn into isolation if I am not careful.

This year, I pushed myself to change that. I reached out to people I admired and deepened relationships I already had. Those small actions led to some of the most meaningful relationships I’ve built so far: mentors, collaborators, peers, and partners who challenged my thinking and expanded what I thought was possible.

For instance, I deepened my relationship with my mentor - the amazing Martina Launchengco, whom I met on LinkedIn through one cold outbound message. She has been a huge collaborator and inspiration since then.  

But support doesn’t just show up in professional settings.

I’m often told I’m a “super mom” for running a business while raising young kids. The truth is, I couldn’t do this alone. I have an incredibly supportive partner and a strong support system at home. There is real, invisible labor behind everything I’m able to build, from help with childcare, logistics, and the emotional weight of day-to-day life.  

The more honest I’ve become about needing help, at work and at home, the more sustainable my life and business have become. Growth has accelerated not because I worked harder, but because I stopped pretending I had to – or could – do everything myself.

As I look ahead to 2026, one of the biggest bets I’m making is on people. Who I work with. Who I learn from. Who I partner with. Who supports me behind the scenes. Even as a one-person business, nothing I build is truly solo.

Looking ahead to 2026

As I reflect on the past four years, I feel deeply grateful. Not just for the growth of the business, but for the life it has allowed me to build. My oldest daughter is four and a half. My youngest is ten months old. This work has supported my family, stretched me as a person, and given my days meaning.

It hasn’t been easy. It still isn’t. But it has been worth it.

If I can leave you with one thought as you step into 2026, it’s this: get honest about what you really want to build in your life.  Then ask yourself what one small step you can take right now to move toward it. 

There is a saying I love, which is “too small too fail”. If you take a small enough step forward, even if it’s absurdly small, then you can’t fail (and will only move forward). 

So take that step. May be that is getting clarity about what you want. May be it’s leaving something bad behind to pursue something new. Or may be it’s simply asking for help.  

That belief is at the heart of everything I do at Courageous Careers. I hope some of what I shared was helpful to you.  I’m glad you’re here.

Thank you for reading. I’m rooting for you this year!!

Yi Lin

P.S. If this newsletter has resonated with you, and you’d like to build an intentional career with the right support in 2026, here are all the ways I can help you: 

• Looking to land a new PMM role? → Join the PMM Job Search System (Q1 enrollment opens today!) or check out my 1-1 coaching program

  
  

• Starting a new PMM job and want to ramp fast? → Check out my 1-1 PMM Onboarding Program

  
  

• Want to thrive, get promoted, or gain clarity in your role? → Check out my 1-1 Leadership Coaching Program

  
  

• Need support for your PMM team or company? → check out my advisory, consulting, and training services