👋 Hello, innovators!

Like it or not, we live in interesting times, where personal decisions are intertwined with systemic shifts. This newsletter answers a reader question that explores my recent transition from corporate leadership to entrepreneurship, a move driven by both personal ambition and a recognition of the changing nature of work. I’ll also delve into the ‘Humans Need Not Apply’ debate, examining the line between automation and abstraction, and how we, as humans, can maintain relevance in an increasingly algorithmic world.

Let’s explore the practical steps of a career pivot, while confronting the existential questions posed by the rise of AI!

Ask the Author: Navigating the Leap

👉 Have a question for me? Hit up my Questions Inbox or message me on LinkedIn and I’ll address it in an upcoming newsletter issue! You’ll also get a shout-out. 😊

This question comes from Nick Korte, Co-host of Nerd Journey Podcast, who has been extremely supportive and shared his network of podcasters with me back during the January announcement. I’ve summarized his questions into this singular question:

“Reflecting on your decision to leave Slalom, how did you navigate the emotional and practical aspects of resigning, specifically in terms of your boss, your team, and the transition to entrepreneurship?”

Excellent question! Here’s a breakdown of how I approached it.

The Resignation Conversation

Be classy when it comes to leaving a job. I wrote a one-page document with everything I wanted to say, then I met with my people leader (boss) to discuss my decision at length and make sure we both aligned on the talking points. I gave 5 weeks notice to be sensitive to my position in the company and the disruption my departure would cause. Once the conversation had concluded, I sent a summation via email to officially resign.

The document contained:

• Appreciation for the work and experiences, including examples and details
• Intentional focus to finish my last project fully and successfully, which had 5 weeks remaining to the end date
• Unwavering devotion to continue to serve my people by completing annual performance reviews (due the same month I was resigning) and official company-filed feedback for everyone on my team (people remember how you make them feel)
• Availability to subcontract for a short period upon my departure to avoid putting the team in a lurch (if needed, which it was not)
• Leaving the door open to return in the future should my plans go awry (don’t burn a bridge)

I was straight forward about my plans to take some time off, along with a “plan to make a plan” over the next 6 months while I started something of my own. There didn’t seem to be any reason to hide this. Plus, I wanted to share in the excitement of building something new with my colleagues, many of whom are also friends! 😊

Informing the Team

I let my team and trusted colleagues know shortly after. Reactions were a mixture of sadness in seeing me go combined with excitement to see what I would go build. As the news spread, leaders across the company came up to shake hands or give me some advice. Many other leaders have taken breaks to reset, plan, and recharge. Some come back, some don’t. They understood where I was coming from and reassured me that their doors (and the company’s doors) would remain open. It felt really nice!

If I had instead been hired by another company, instead of going solo, I would have kept the news of my destination to myself because I don’t feel it wise to share that sort of thing until I actually start the next job. You never know what might happen between leaving one job and starting the next and karma is a bitch.

I set up a quarterly lunch with my team so we can go eat 🌮 tacos and be nerds together on a recurring basis. The last was one was in February and was super fun! There’s not a bad bone among the group and everyone was welcoming and asked a million questions about how things were going.

People Leadership

When I joined Slalom, I was pretty adamant about not being a people leader for the first year or so. I was burned out from the past 6 years of leading entire departments filled with managers and individuals. However, due to the rapid growth of my consulting group, I hired 4 individual contributors before the first year was over. The alternative was overloading my boss with direct reports. I was one of the few folks with leadership experience in a rapidly growing team, so I stepped up out of necessity. Sometimes you just have to be the adult in the room.

I don’t mind being a people leader or manager but it’s not my first love. Due to the way consulting works, I rarely worked on projects directly with my team, making it extremely hard to influence their growth and adequately judge their performance. I would much prefer to work with my team. I want to see how they think, how they respond to situations, and how they perform and react in meetings with clients. That’s the part I’m passionate about, and it balances against all the “HR stuff” that is much less fun (but entirely necessary) to do.

I am VERY happy about leaving people leadership behind, I really NEED the break. It’s extremely important and HEALTHY to pendulum between being a people leader and being an individual contributor from time to time.

I still mentor a handful of folks. Being a people leader is not required for being a mentor and positively influencing the hearts and careers of others. At least as a solo entrepreneur, I know for certain that I can now finally take the break I’ve wanted and remain as an individual contributor until I’m ready to hire.

The Shift to Entrepreneurship

The origin of my desire to go solo came from two places.

The first is my wife, Nella. She’s been an entrepreneur for most of her adult life, and is my most trusted source of guidance. I was working late one evening last Fall when my wife came into my home office as I was ranting about the financial tracking work I was doing. I owned everything about my projects – staffing plans, timecard tracking, invoicing, maintaining margin, designing the solution, leading the delivery team, status reports. Everything. Nella commented that I was already running my own small business. That’s when it dawned on me – duh, she’s right!

Add to that the second source, which is Slalom’s “business builder” mindset. Slalom wanted all Director titles and above to feel like entrepreneurs inside the company building their own businesses. This meant that I already had a taste of the Kool-Aid in the form of formal training in executive leadership, financial management, program management, solution ownership, emotional communications, change management, contracting vehicles, and other “scary hard stuff” from some of the best in the business. People with 30+ years of experience on billion dollar programs. Slalom builds leaders for breakfast, lunch, and dinner – it was part of why I was so attracted to the organization.

Given Nella’s inspiration and my Slalom training and experience running a mini-business, I asked myself: why not do that for myself, instead of for others? The rest is history.

I hope this gives you some insight into my journey. It was a complex decision with many layers, but ultimately, it felt like the right step for me.

Avoiding Anti Patterns

I very intentionally did NOT do several things:

• I did NOT post some long sob story on LinkedIn about the job change with a million people tagged to garner attention and likes that do not matter. I kinda hate these posts.
• I did NOT update my profile to say “Chris has a new job doing X” because, again, it doesn’t matter – there is no substance to that in my mind. I made the change silently.
• I did NOT send out a massive communication internally at Slalom with my departure. I let people close to me know, and that’s it, because it really wasn’t anyone else’s business what I was doing.

As Tom Holland said: “If you have a problem with me, text me. If you don’t have my number then you probably don’t know me well enough to have a problem with me.”

When I finally did post something about the change, it was because I had something to share – the new podcast! And I didn’t even post this until I had 4 episodes in the can. You do you, boo, but I think actions speak louder than words, and results speak louder than intentions.

Thoughtfully Critical Podcast Update

I continue to try and level up my video editing game. The most recent episode focuses on my usage of AI tools and their impact on my small business.

YouTuber CPG Grey published a video 10 years ago titled Humans Need Not Apply. This resurfaced in my subscription feed as the advent of AI tools and agents are once again bringing this topic and existential questions into light.

This is a hard time for many people. My LinkedIn feed is filled with people looking for jobs after being let go from tech companies. Several US stock markets are headed into the red, decimating retirement savings. The price of basic staples like food (🥚eggs!), housing, rent, and automobiles are sky high. It’s hard not to let the whirlwind of negatively pick you up and toss you around a bit. I try to stay informed without getting too caught up in the bad vibes, but the bad vibes exist.

Let me offer a few data points to help counter these feelings, if even for a moment.

Keep Calm and Carry On

I recently attended the 22nd annual SCaLE (Southern California Linux Expo) down in Pasadena, California. It was my first one, and is now an event that I will DEFINITELY attend again in the future. Family friendly, great speakers, minimal vendor bullshit, and game nights – hell yes! In a word: AMAZING. I’ll talk more on this in the next Thoughtfully Critical podcast, don’t worry.

A familiar face was part of the speaking crowd, the infamous Kelsey Hightower. I sat in during his hour long Q&A session and later in a panel on the chaos of software development. The man drops gold nuggets of wisdom like a gumball machine. He was asked opinions on AI and impact on the job market in both forums. Kelsey says that he advises startups and helps perform due diligence for investors of said startups.

I’m paraphrasing a bit, but his POV was:

“Will AI replace your job? Well, what is your job? Think about abstraction vs. automation. You’re a human, be one.”

And another one:

“Growth by any means is insane. Grow forever equals die. Focus on purpose and clarity. You don’t need a better paintbrush to be a better painter; you need to learn to think.”

There’s a lot of low level, repetitive tasks out there. These tasks are ripe for automation. But the abstraction layers, the cognitive layers, and the creative juices must still flow – and that’s where humans can and will remain. Other speakers likened today’s AI to having 4 year-olds with vast knowledge but little to no context, and I’d agree – the context matters (it always has). And humans are pretty damn good at context.

By the way, I HIGHLY recommend reading this article from luminary Ash Pembroke (one of my favorite people) titled GenAI: Are Humans Horses? I first met Ash years ago while at Slalom as part of a collaboration with Slalom’s S2 (Slalom Strategy) team, the research / strategy arm of the organization. Come for the deep dive, stay for the #horsegirlsunite.

Taking Action

So what can you do about it and how can you take action? Another YouTuber named Productive Peter offers some advice on the Wisdom Tax. I’d suggest watching this video. I’d suggest doing what he says by really digging deep into how you operate, how you think, what value you perceive to offer the world, and how to trade in willpower for better systems design.

As my Mom always told me:

“Don’t sweat the small things. And everything is a small thing.”

Interesting Links

Here are some fun, interesting, and educational links that I’ve gathered to share with you.

Pour a little 🍷 out for Skype. Love it or hate it, this was the same platform I first started using when recording podcast episodes over a decade ago – everyone had a local recording going, plus the Skype recording, and then we mixed them all together manually to produce the mp3 file.

This article from The Technium on Class 1 and Class 2 problems was fascinating to me. I’m late to the game on this one.

Arvid Lunnemark, Co-founder of Anysphere (maker of Cursor), wrote It Is Time to Move Beyond End-to-End Encryption back in 2021. I found this while I was doing research on the company and really enjoyed the way he explains both encryption and metadata.

It’s finally becoming cheaper to move to Austin, as Bloomberg reports Austin Rents Tumble 22% From Peak on Massive Home Building Spree. I guess if you build more rental properties, the balance of supply and demand shifts. Imagine that! 😜

Reader Lothilus shared a Hugging Face Agents Course that he’s taking. Looks cool, I’m tempted to carve out time to go through this myself.

Infamous YouTuber Technology Connections published Algorithms are breaking how we think. Get off my lawn you dirty hippies! Jokes aside, I’m one of those very few who actually use the YouTube subscription feed, generally avoids the algorithmic recommendations (I feel this just leads to doom scrolling and information bubbles), and uses Unhook to clean up my YouTube page in Chrome.

Reader Lior shared this GitHub Issue Forms link. You can define different input types, validations, default assignees, and default labels for your issue forms. Note: Issue forms are currently in public preview and subject to change.

That’s it for this issue! Let’s talk again soon. ✌️& 💙