👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence for Senior ICs and Managers.

✨ Course update: I opened the new May 2025 cohort a few weeks ago, and it’s already 40% full. This cohort will be the only opportunity to take the course this spring (the next time the course will be offered will be in the summer). To learn more, here are the course details.

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We all know comparison is the thief of joy, but for most of my life, I was very skilled at comparing myself to others. I could describe in great detail and specificity exactly where I was lacking, and why someone else was better than me.

I was proud of my intellectual honesty. Weaker operators might make themselves feel better, but not me. I was committed to staring my weaknesses in the eye.

Having an unvarnished view of myself was useful, to a point. On the one hand, the paranoia fueled me to work extremely hard. I wasn’t delusional about where I stood, and I was constantly learning from others around me.

On the other hand, most of the time, I felt shitty about not making enough progress vis-a-vis my peers.

When a friend would compliment me or be impressed at something I accomplished, I was quick to point out a bigger fish.

One day, I realized: The urge to put myself down is an invented obligation.

The good news was this was all in my own head.

The bad news was this was all in my own head.

If I wanted to stop being in a rat race, it dawned on me that I could…choose not to enter another race race. But I had to consciously choose to stop participating in this imaginary competition.

I wrote the below on LinkedIn in October 2023, when I had just left my startup, Maven. This was the first time popping my head up after three intense years of company building, and I spent that summer taking stock of where I was and reflecting on what I wanted to do more/less of. Could I be a more hospitable, friendly voice to myself? Yes, I realized.

Here’s the post below.

There’s always another rat race if you want to be a rat in a race. When I graduated from UC Berkeley, I thought, “Now I’m no longer in the Haas student rat race.”

When I left the fashion industry and joined a startup, I thought, “Now I’m no longer in the corporate retail rat race.”

When I moved from SF to New York and bootstrapped a company, I thought, “Now I'm no longer in the Silicon Valley tech operator rat race.”

When I started growing my audience as a creator, I thought, “Now I’m no longer in the FTE rat race.”

When I was a solopreneur in between my two companies, I thought, “Now I'm no longer in the CMO path rat race.”

When I started a VC-backed company with Tier 1 investors, I thought, “Now I’m no longer in the solopreneur rat race.”

When I left my startup and started working on my own, I thought, “Now I'm no longer in the tech founder rat race.”

Each time, I just joined a new race, with new rats.

I thought I was out of the race, until I looked up and found myself suspiciously comparing myself to others without realizing it was happening.

Now, I want to break the cycle. It's enough racing. I've raced since I was 16 years old, and I'm 37 now. I'm actively breaking the cycle, and it will take effort. It's moving a battleship in the opposite direction than the one it's been sailing in for years.

“Already” is the word for this spring.

I want to remind myself of what I already have, how I’m already achieving my goals, and how I’m already the person I want to be.

Flash forward to March 2025, and I’m proud to say I’ve made a lot of progress. I definitely still catch myself feeling jealous of others, but on most days, I feel pretty motivated by my work and think less about what other people are doing.

If you are prone to beating yourself up for not being as “far along” as you should be, let this be a sign that you can change how you think too.

Obviously, I’m not saying you should stop improving or get complacent. Like many things, the answer is not one or the other: You can recognize how you’re already the person you want to be in some ways AND continue working towards being more of that person. You can acknowledge how you’re already doing some things right AND continue sharpening your skills.

What you can do today

If you are someone who is too hard on themselves, you may need to actively train your brain to see through a different, more positive lens.

No, you won’t lose your edge or get soft. You are probably too high strung to ever be so relaxed that you lose your edge.

The risk is actually that when you’re overly focused on the negative, you develop a warped view of your abilities. You become under-confident compared to your actual skills. This negatively impacts the way you communicate with others, the way you advocate for your ideas, and how willing you are to make bold moves.

It warps your ability to see clearly. For example, you might think your situation is futile when it’s not. You might see a bigger gap than what’s actually there, and give up when you didn’t need to.

Meanwhile, focusing on ways that you are already doing well, already winning, already doing great, is a way to have a more ACCURATE view of your situation. When you are overly anchored on the negative, you need to reset by swinging the pendulum to be overly positive to have a chance at landing someplace neutral.

I call this type of thought experiment a “rubber band exercise”: You stretch the rubber band so you when you release the tension, the rubber band is a bit looser.

So here’s a rubber band exercise for you. Ask yourself:

• In what ways am I already the person I want to be?

• How am I already achieving my goals?

• How am I already becoming who I want to be?

Remember: You can choose to run your own race. You can choose to celebrate what you’re doing right, and how you’re already the person you want to be.

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Do you tend to compare yourself to others to a point where it becomes counterproductive? More importantly, how are you already on your way to doing the things you want to do or being the leader you want to be?

Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

Course update: Executive Communication & Influence for Senior ICs and Managers

Since last fall, I’ve been focused on 1:1 executive coaching with a select group of clients, and on making my course the best communication and influence course for hands-on builders.

Every cohort, I meet the most interesting, sharp, thoughtful operators and I’m pretty much constantly in awe that I get to support leaders this like this.

We wrapped up the February cohort a few weeks ago, and I’m thrilled to share the latest student reviews:

“Wes’ course is a short, 2-day commitment that is packed with actionable advice and frameworks that you can put into practice immediately. This course changed the way I approach communication with my stakeholders.”

- Caro Galvin, Senior Product Manager @ GitHub

“I can't say enough good things about this course. Wes is so approachable and professional, and she offers an absolute treasure trove of resources, tips and frameworks that will change the way you approach your work and your life. If you're wondering if this course is worth the investment of time and money - the answer is a resounding yes.”

- Helen Jerman, Global Digital Content Manager @ ADI Global Distribution

“Great course! I appreciated Wes's actionable recommendations and the ability to practice tactical skills like rewriting communications of our own.”

- Cameron Langford, Founder & Principal Consultant @ First Principles Communications

“This was excellent. The course modules were cohesive and useful. The take-home materials we got have already been helpful to me in my day-to-day. Wes is a brilliant instructor and I particularly appreciated her feedback on the live exercises (rewrite this email, draft a script, etc.) for how targeted and direct it was.

It was also clear during the lessons that Wes was applying her own principles (signposting, right amount of context, etc.) to the course material itself. This made the lessons more effective, of course, but it was also a cool demonstration that ‘hey, this works’ that we could see for ourselves on the spot.”

- Tushar Chandra, Software Engineer @ Loop

“This course is a MUST, and one of the best learning experiences of my career. I can confidently say I would recommend this to anyone who is starting to interact more with leadership, or who wants to be prepared for when they do. (So…. Everyone.) I will probably never shut up about how much I loved this course and how immediately I am using the skills from it.”

- Desirae Odjick, Product Marketing Lead @ Shopify

The April cohort is full, but the May 2025 cohort is now open. The course dates are May 15 & 16 at 12:00 - 3:30pm ET with an optional Q&A afterward. If you’ve been thinking about joining, you’ll be in good company. I hope to see you in class.

→ Reserve your spot in the May 2025 cohort

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