profile

đź’ˇ The Lightbulb

A daily email about monetizing and visualizing your corporate expertise. Give me ~1 minute a day, and I'll help you turn what you know into your most differentiated and lucrative asset.

Wes Wheless Pia Silva No BS Podcast Nov 2026

đź’ˇ"Wow, I'm the expert in the room"

I’ve been working with some objectively amazing Parachute Plan clients over the past few months: A seasoned Big Tech software engineer watching the shape of his role become unrecognizable, and now has his eye on advising, speaking and teaching A jack-of-all-trades VP of biz ops for a regional homebuilder ready to offer his lens to other trades businesses independently, while building a new side-hustle business of his own A sharp-eyed, tenured product designer feeling soul-sucked and hamstrung...

đź’ˇ My 'forgotten' layoff

Pondering that 'forgotten' layoff on Pink Slip Pavilion I talk a lot about the two consecutive tech layoffs that led me to the solo path. But there was a third one, early in my career, that I often fail to mention or give enough credit. I'll set the scene. It was late 2008, Lehman had just failed, markets were unraveling, and there I was -- 24 years old, hitting my two-year mark at one of the big consulting firms, thinking none of the outside noise had anything to do with me and my budding...

đź’ˇ Two strangers on a train

I’m not particularly precious when it comes to approving connections on LinkedIn. I’ll do a semi-subconscious screen for leading indicators of future nuisance (e.g. lead gen services, VAs, book marketers)… ...or those obviously just beefing up their follower count (if someone with 50k followers was actually interested in engaging with me, they’d have emailed or left a note). But otherwise, I tend to approve and simply ask: “Thanks for connecting, did one of my posts catch your eye?” This does...

đź’ˇ You're learning a language

I’m back at my desk in Seattle today after two weeks abroad — a week in London where I was still doing some writing and book promo, then down to the Canary Islands with a friend, where I was really able to disconnect and recharge. The Canaries are a Spanish territory off the coast of Western Africa with a pretty stunning mix of beach, mountains, forest and desert all in one place. It’s sometimes easy to forget the islands are Spanish given the diversity of tourists visiting from all over...

đź’ˇ Nine experts walk into a restaurant...

It’s 6:30pm in London, and one by one, they start to arrive. “They” are nine sharp, motivated fellow alums from my business school, each with impressive corporate backgrounds and representing many industries: Insurance, fintech, shipping, talent sourcing, public health, aviation tech. So. Much. Domain expertise. All gathered around one table in the private dining room of a posh Sri Lankan restaurant in Shoreditch. All here to hear my take on leaving corporate and going solo. And while the...

đź’ˇ [LISTEN] My convo with a CFO for soloists

Brooke Koeninger is a fractional CFO for consultants, coaches and creative services founders. As someone who also serves soloists, I was excited to join her podcast, Scale With Clarity, to talk about — as cliché as it sounds — designing the work life you want. After all, that’s the overarching umbrella, right? The dream? Across the board, I hear from those who have made the leap solo to those who are just testing the water that they (we!) are simply seeking to make a living with freedom,...

đź’ˇ Finally, some space to rethink this email thing

A change of scenery for some quiet reflection Hello! And happy Labor Day to those in the US & Canada. I’m writing from London this morning — a multipurpose trip of visiting old friends, a book dinner tomorrow night, and my first vacation since New Year’s. (Interestingly, I’m finding that a self-designed work life gives me enough personal freedom in a normal week that perhaps a full-blown weeks-long getaway isn’t as necessary for me as it once was.) But alas, I’m here, “off the clock” in my...
brown eggs in a box

đź’ˇ "I think you're overthinking this."

“I think you’re overthinking this.” It’s something I’ve heard a lot in my life. But this specific time was about three years ago, from my then-business coach Melisa. It was my last session with her in our 3-month cycle, and I’d decided to spend a good chunk of it having her talk me off the ledge about, of all things, posting on LinkedIn. For my entire first year solo, I hadn’t posted a single time. I could say it was because I didn’t “need” to put myself out there — I’d been fortunate with a...

đź’ˇ The fear of corporate exile

Earlier this month, I officially kicked off my book tour for The Expert’s Privilege by hosting a “Can I Go Solo?” dinner with the Wharton Alumni Club of Seattle. I'm building this tour around small gatherings, intentionally. After all, we’re talking about a major career pivot, one that elicits that wild combination of curiosity and excitement, but also self-doubt and vulnerability. Given the intimate size of the dinner, we were able to explore a lot of that in depth. What was most surprising...

đź’ˇ Leaving the block party early

This morning was noticeably quiet. Not my calendar - that was pretty busy. But rather, the actual noise level was so minimal compared to the craziness of the weekend. See, there’s a massive “block party” in my neighborhood every summer. I used scare quotes because this party isn’t just a few dozen neighbors gathering around a BBQ grill and a Bluetooth speaker. No, this party is a full-blown, ticketed, four-stage music festival held directly on five densely-populated city blocks. In past...

A daily email about monetizing and visualizing your corporate expertise. Give me ~1 minute a day, and I'll help you turn what you know into your most differentiated and lucrative asset.