Lenny RachitskyModify

2026-08-31 23:01:58

How I turned Claude into a self-improving PM assistant | Daniel Blum (PM, Melio)

Brought to you by:

• Optimizely—Your AI agent orchestration platform for marketing and digital teams

• Jira AI SDLC—Get your tokens’ worth with Jira

Daniel Blum is a product manager at Melio who has built a self-improving AI system that now handles 70% to 80% of his workday. In this episode, he breaks down how Claude and Cowork manage his Notion board, prepare him for the week, scan Slack and email for important context, and learn from his edits without waiting for explicit feedback. He explains how he turned the system into a 15-minute onboarding experience for other Melio employees, why the first few weeks of building with AI can feel painfully slow, and how the payoff eventually helped him accomplish a week’s worth of PM work in a single day.

Biggest takeaways:

1. The architecture matters more than the AI tool itself. Daniel believes a system becomes genuinely powerful when it can update its own core files and connect to the tools someone already uses. Once those pieces are in place, the system can improve and become more useful over time, whether it is built in Cowork, Codex, ChatGPT, or something else. He created a transformative setup using the tools Melio had already licensed, proving that the underlying architecture matters more than choosing the perfect platform.

2. Context isn’t something you set up once; it requires an ongoing system. Daniel spent months giving Claude voice memos, links, decks, and verbal brain dumps to build detailed context files for every area of his work. He then created recurring updates that refresh those files every few weeks. This keeps the gap between what Claude knows and what is actually happening inside the company as small as possible.

3. The most impressive part of Daniel’s morning brief is that it identifies what it does not know. Each day, Claude reviews his Slack, email, and notes for unfamiliar terms, projects, or goals that do not appear in its context files. It then asks Daniel targeted questions to fill those gaps. When it encountered the phrase “settlement cap,” for example, it had already read the relevant thread and understood the general idea. It only needed Daniel to confirm the meaning before saving it.

4. The value of a personalized AI system builds slowly, then becomes enormous. Daniel is candid about how frustrating the first few weeks can feel. The system does not know enough yet, its work is slightly off, and nearly everything requires a second look. But once someone pushes through the work of centralizing information and building context, the payoff can be difficult to overstate. He can now accomplish in one focused day what previously took him an entire week.

5. Self-improvement loops learn from the difference between what the AI drafted and what the person actually sent. Daniel built a weekly skill that compares Claude’s original drafts with his final versions, then uses those differences to improve future work. It resembles Alex Lieberman’s “write like me” loop, but it relies less on explicit feedback. Instead, it observes Daniel’s actual behavior and learns from the small edits he makes instinctively.

6. Feedback telemetry turns personal AI workflows into products that can improve themselves. Every one of Daniel’s skills captures moments of friction. If he says something is not working or requests a correction during a session, the system logs that signal. Once a week, his improvement loop identifies the most common problems and recommends updates. It is essentially analytics for his internal tools, and it gives him a structured way to refine the system based on how it performs in real life.

7. The Workstation plugin addresses one of the biggest barriers to adopting AI inside a company: personalization. Daniel watched several product managers struggle with Spectacular, his spec-writing gem, because it had been designed entirely around his own working style. He responded by building an onboarding flow that connects each employee’s tools, maps their colleagues, and learns their voice in about 15 minutes. Instead of starting from scratch with a generic system, every Melio employee now begins with a strong shared foundation personalized to their needs.

8. The biggest remaining limitation of today’s AI systems is persistence, not intelligence. Daniel estimates that Claude already handles 70% to 80% of his workday. What it still cannot reliably do is continue working in the cloud while his computer is off. He is already preparing for that future by teaching Claude how to recognize the “closed state” of different tasks. If a drafted Slack message is no longer saved, for example, the system can infer that it was probably sent. When truly autonomous operation becomes available, Daniel’s system will already understand what completion looks like.

If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.

Catch you next week,
Lenny

P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.

2026-08-31 20:04:18

Daniel Blum is a product manager at Melio, a B2B payments company, and one of the most systematic thinkers I’ve had on the show when it comes to personal AI infrastructure. He’s spent the past year building a Claude- and Cowork-based productivity system that manages his Notion board, processes his Slack and email, and runs self-improvement loops every week without needing to be prompted. Beyond his own workflow, Daniel built and scaled a “Workstation” onboarding plugin that gets any Melio employee up and running with a personalized Claude setup in about 15 minutes.

What you’ll learn:

1. Why Daniel says the two rules that make any AI system powerful aren’t about the tool you pick

2. How his weekly prep automation fills an entire Notion board from scratch every Sunday, without his touching it

3. The morning brief feature that teaches Claude new internal terms on its own, so company jargon never slows it down

4. Why he describes Notion as “read-only” now, and what that says about how PM workflows are changing

5. The self-improvement loop that watches Daniel’s edits, spots recurring friction, and suggests new skills to build

6. How he uses a skill called “Improve” to filter the endless flood of AI tips without drowning in them

7. What he built to scale his personal system to every PM at Melio, and the UX lesson he learned the hard way

8. The capability gap that’s still keeping him from running 100% of his work through Claude

Brought to you by:

Optimizely—Your AI agent orchestration platform for marketing and digital teams

Jira AI SDLC—Get your tokens’ worth with Jira

In this episode, we cover:

(00:00) Daniel’s background and the PM overhead problem he needed to solve

(03:30) His AI stack at Melio

(05:00) The two rules that make any AI system genuinely powerful

(06:00) The Notion board Cowork built for him (and manages on his behalf)

(07:30) How he contextualizes Claude with voice memos, links, and recurring updates

(09:00) His weekly prep automation

(11:00) His morning brief

(15:00) How Claude flags unknown internal terms and saves them to context

(17:30) Running 70% to 80% of his workday through Cowork

(19:00) Chrome connector vs. MCPs for tools without integrations

(20:00) The real ROI question: why the early weeks feel slow, and why you push through anyway

(25:00) Scaling the system to the team with the Workstation plugin

(26:30) The self-improvement loop

(31:00) How the Improve skill separates actually useful AI tips from the hype

(32:00) The Workstation onboarding flow, and the UX lesson from distributing “Spectacular”

(38:00) The 20% Claude still can’t do, and what changes when it can

(41:00) What Daniel spends his reclaimed time on

(42:30) Claude rage

Tools referenced:

• Claude: https://claude.ai

• Notion: https://notion.so

Other references:

• From a $6.90 newsletter to $3M API: How a non-coder built Memelord | Jason Levin: https://www.lennysnewsletter.com/p/from-a-690-newsletter-to-3m-api-how?utm_source=publication-search

• How the founder of Morning Brew built a Claude content machine that never runs out of ideas and never sounds like slop | Alex Lieberman: https://www.lennysnewsletter.com/p/how-the-founder-of-morning-brew-built?utm_source=publication-search

Where to find Daniel Blum:

LinkedIn: https://www.linkedin.com/in/blumd/

Website: https://www.imdanielblum.com

Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

2026-08-30 20:31:30

Tara Seshan leads product for ChatGPT Work at OpenAI (alongside previous podcast guest Andrew Ambrosino, who’s her engineering manager). Before OpenAI, Tara spent over six years at Stripe, where she joined as one of the first five product managers. She went on to lead product for Watershed, which Time magazine named one of the best inventions of 2022, and she is also a founder and Thiel Fellow. Most personally meaningful to me: Tara is one of the three inaugural Lenny’s Newsletter Fellows, a program I ran a couple of years ago to spotlight the most exciting up-and-coming product leaders.

In our in-depth conversation, we discuss:

1. The shift from “rowing” to “steering,” and why human judgment and ambition will become differentiators as AI takes on execution

2. How OpenAI thinks about building for model capabilities two to three months out

3. OpenAI’s best internal memes, such as “Is this maximally accelerated?” and “Are you mainlining it yet?”

4. Why ambition is the new bottleneck for companies, and why elevating others’ ambitions is now the key part of the PM job

5. Writing as thinking vs. writing as reporting

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

Where to find Tara Seshan:

• X: https://x.com/tarstarr

• LinkedIn: https://www.linkedin.com/in/tarstarr

• Newsletter: https://substack.com/@taraseshan

Referenced:

• Codex: https://chatgpt.com/codex

• ChatGPT Work: https://openai.com/chatgpt-work

• Stripe: https://stripe.com

• Watershed: https://watershed.com

• Thiel Fellowship: https://thielfellowship.org

• Meet your Lenny’s Newsletter Fellows: https://www.lennysnewsletter.com/p/meet-your-lennys-newsletter-fellows

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir

• The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennysnewsletter.com/p/the-nature-of-product-marty-cagan

• Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty

• Patrick Collison’s examples of fast projects: https://patrickcollison.com/fast

• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Andrew Ambrosino on X: https://x.com/ajambrosino

• Tyler Cowen’s website: https://tylercowen.com

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• “Chop wood, carry water” quote: https://buddhism.stackexchange.com/questions/15921/what-is-the-meaning-of-the-zen-quote-before-enlightenment-chop-wood-carry-wat

• 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live

• Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay

• Brie Wolfson on X: https://x.com/zebriez

• The playbook for building high-talent-density teams | Adam Ward, Head of Talent at Cursor: https://www.lennysnewsletter.com/p/the-playbook-for-building-high-talent

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• Sutter Hill Ventures: https://shv.com

• Snowflake: https://www.snowflake.com

• Mike Speiser on LinkedIn: https://www.linkedin.com/in/mikespeiser

• Footnotes and Tangents: https://footnotesandtangents.substack.com

• The Power Broker Book Club: https://www.robertcaro.org/copy-of-six-books-six-ny-times-book

• The Odyssey: https://www.imdb.com/title/tt33764258

• Rashomon: https://www.imdb.com/title/tt0042876

• Akira Kurosawa: https://en.wikipedia.org/wiki/Akira_Kurosawa

• Kevin Kwok on LinkedIn: https://www.linkedin.com/in/kevinakwok

• The Work You Do, the Person You Are: https://www.newyorker.com/magazine/2017/06/05/toni-morrison-the-work-you-do-the-person-you-are

• Ari Weinstein on X: https://x.com/AriX

• Sky: https://sky.app

• Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config

Recommended books:

• Barbarian Days: A Surfing Life: https://www.amazon.com/dp/0143109391

• Anna Karenina: https://www.amazon.com/Anna-Karenina-LEO-TOLSTOY/dp/8175993421

• The Power Broker: https://www.amazon.com/dp/0394720245

• War and Peace: https://www.amazon.com/War-Peace-Leo-Tolstoy/dp/8175992832

• Wolf Hall: https://www.amazon.com/dp/0312429983

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

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2026-08-30 02:59:48

👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.

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2026-08-25 21:04:15

👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Jobs | Lenny’s Podcast | Lennybot | How I AI | Become an AI-Native Builder and my other favorite AI/PM courses

Subscribe now

P.S. Get a full free year of Cursor, Notion, Replit, Lovable, Wispr Flow, Linear, ElevenLabs, Factory, PostHog, Granola, Brain.fm, Waking Up, and more, by becoming an Insider subscriber (while supplies last). Learn more.

Building on last week’s very exciting launch of Lenny’s Jobs (that’s a lot of likes!), I’m thrilled to bring you a companion post that will help you clarify what job to look for in the first place.

Cliff Maxwell teamed up with the legend Bobby Moesta (co-creator of the Jobs to Be Done framework and a two-time guest on Lenny’s Podcast) to build Vocation, a career navigation platform that helps professionals figure out their next step. Cliff’s own career has spanned building CPUs, education research, product management, venture capital, and serving as Chief of Staff to the late Clayton Christensen. Based on insights from over 1,000 interviews with professionals changing jobs and hundreds of one-on-one coaching clients, this hands-on guide will help you take a step back and connect with what you truly want from your work—and life.

Let’s get into it.

It’s a disorienting time to work in tech right now. For some, the rise of AI is a thrilling adventure, but for others, it’s a source of existential dread. No matter how you’re feeling, change is coming. The World Economic Forum reports that by 2030, 39% of today’s skills will change or become obsolete, and more than 90 million jobs will be displaced even as 170 million new jobs will be created.

Every generation of workers in tech has lived through recessions, layoffs, and technological change, but AI’s impact on work will be fundamentally different. It won’t just require new skills. It is redrawing the boundaries between roles and changing the day-to-day responsibilities inside them. Work may feel unstable now, but this will likely be the most stable it feels for a long time.

With this much uncertainty on the horizon, it is imperative that you develop the ability to navigate change. As your responsibilities shift and new opportunities emerge, the durable career advantage will come from knowing what kinds of problems, people, and environments bring out your best work—and having a repeatable process for identifying your next step even when the ultimate destination is unclear.

For the past year I have been building career navigation infrastructure with Bobby Moesta, one of the creators of the Jobs to Be Done framework and a two-time guest on Lenny’s Podcast. Bobby brings a product-oriented lens to career change: you are the customer, and the right next career move is the product you are looking to purchase.

Through more than 1,000 in-depth interviews with professionals changing jobs (some by choice, some by necessity)—and hundreds more people we have coached since—we identified what helps people make a successful job transition, and built a process to support them.

This is not a laundry list of LinkedIn hacks, resume tips, or ideas for how to automate your recruiting efforts. This is a step-by-step formula for designing a system that allows you to understand yourself, your context, and your best next steps when you’re in a state of change.

In this post, I’ll help you answer six fundamental questions that will instill confidence and focus anytime you are navigating a transition at work. Each question comes with exercises and tools to help you build understanding.

1. What kind of career progress do I want?

2. What career quest am I on?

3. Which work brings out my best?

4. What possible moves should I explore?

5. Which tradeoffs am I willing to make?

6. Can I get what I need without leaving?

Once you know your answers, you’ll be equipped to find your bearings now and every time the labor market throws you a curveball.

1. What kind of career progress do I want?

About a year ago, we coached an individual who, after spending several years at a startup that was running out of funding, assumed his next step was another early role in a venture-backed company.

After evaluating his core motivations and reflecting on his growing desire for impact, he found an opportunity to lead the entrepreneurship center at a local university, a job that he previously would have avoided and that none of his peers would have recommended. When he met with the administration, they effectively hired him on the spot, telling him, “You are exactly who we were looking for.” He’s now crushing it in his new role.

This story demonstrates the difference between career “progress” and “progression,” a distinction that is critical to understand when you are at a transition point in your career.

Progression is the philosophy that underpins most people’s mental model of careers. You start as an IC, get promoted, and up and up you go on the imaginary career ladder. This mindset will become increasingly less relevant as AI continues its march through knowledge work. Job boundaries and job titles will continue to blur, new job titles will emerge, and companies will struggle to neatly map job descriptions and career pathways into their org chart or KPIs.

Progress, on the other hand, is contextual and dynamic. It is ultimately a question of what your professional Job to Be Done is, and allows you to chart your own course rather than follow a single, narrow path of progression. Depending on your context, progress may be about autonomy and flexibility, preparing for the future, respect and recognition, or simply collecting a paycheck during a time of instability. It can look like a more traditional step up, but it may also look like a lateral move or even like a step back from the perspective of others—while it solves the most important problem in your life and gives you space and time to move forward later on.

A focus on progress is an active commitment to putting yourself in environments that will bring out your best. It helps you stand out amid the army of applicants all reaching for the same rung on the career ladder. Progress gives you the freedom to see your career in chapters and create space to be emergent rather than assuming you have to write one linear story all at once. To do this, you have to define the progress you’re seeking right now.

A 10-minute progress exercise

Take a blank page (or, if you’d like a live template, we made one for you here) and complete the sentence: I want to leave or change my current situation because…

Write down every friction or negative force you’re experiencing right now, or that you last experienced at work. We call these pushes. Do not polish the language. “My manager changes priorities every three days, and it’s getting exhausting” is more useful than “I want better leadership.” Unpack each one of these, and ask yourself “why” until you get to the root cause.

Then complete this sentence: I want my next chapter to give me…

List the desired outcomes you wish were true right now. We call these pulls. Again, make them concrete. “Control over when I do focused work” is more useful than “flexibility.”

Now circle the two or three pushes and two or three pulls that carry the most emotional weight. When you see the forces together, you can start to assemble what progress means for you, not for anyone else. For example, two people may both feel overburdened by new management, but one wants to join a more supportive team while the other is seeking more autonomy to work alone. Your unique combination of pushes and pulls forms the basis for your career quest, or the core motivation guiding your desire for change.

Below is an example of how this might look for someone seeking a new role:

2. What career quest am I on?

When you are seriously considering a job change, or when change is forced upon you, it’s easy to label and hold onto your most immediate feeling, whether that’s burnout, the excitement of something new, frustration, or disrespect. But underlying these emotions, less-obvious and subconscious factors are working together in a unique combination to animate your core motivation for change. This is your career quest.

Your quest for progress should inform every aspect of your job search, but most people skip this diagnosis and go directly to job boards, answer the recruiter’s call, or ask their network about job openings. They are halfway out the door before deciding what they even need this move to accomplish.

For example, I once coached an individual who was frustrated by the lack of leadership opportunities in his product role at a large tech company. When he was recruited to lead and grow the analytics function at a nearby startup, he felt excited and flattered to finally have the opportunity to grow a team.

But as we explored other pushes and pulls acting on him, a more nuanced story emerged. Despite the lack of leadership opportunities, he fundamentally liked his job. He was also in the middle of renovating his home, he wanted to be able to spend more time with his two young kids, and he wasn’t all that excited about leaving product for analytics.

The new role solved his most immediate and apparent problem, but it wouldn’t offer him the progress he needed both personally and professionally.

In our work with professionals looking to make a change, we have identified four common quests for progress that emerge again and again.

These quests are not mutually exclusive; you can be on multiple quests simultaneously, though one usually dominates. Even if you have been laid off and the immediate goal is “I need a job,” reflecting on these quests can help you decide which opportunities deserve your attention, and which you can avoid.

Quest 1: Get out

You have hit a wall you cannot fix from where you stand. Something about the manager, culture, leadership, or environment has made it hard to succeed or remain healthy. The dominant feeling is escape, and the desire to get out is usually quick, not something you stew on for months at a time.

Common pushes:

• Feeling disrespected or not trusted to do great work

• Working for a manager who is wearing you down

• Losing trust or respect in leadership and/or your peers

• Not seeing a place to grow in your current organization

Common pulls:

• The pulls are often vague: a fresh start, a healthier environment, or simply “anywhere but here.”

• When someone is looking to get out, they often accept the first available escape but run the risk of landing in the same conditions at a different company.

Quest 2: Regain control

Work has swallowed too much of your life, even if you still enjoy the work itself.

This quest often follows a change outside work: a new child, caregiving responsibilities, a health issue, or a shift in what you want your life to look like. It can also emerge when a previously manageable role becomes chaotic, or when the way your manager or company leadership is running things no longer works for you.

Common pushes:

• Feeling worn down by management

• Work is dominating your life and you’re starting to make sacrifices

• Unpredictable demands, or feeling challenged beyond your ability

• Little control over your schedule or priorities

• A workload that no longer feels sustainable

Common pulls:

• More time to spend with others

• A job location that fits better into your personal life

• An employer who properly values your experience and credentials

• A scope of responsibility you can sustain

Quest 3: Regain alignment

Your job has drifted away from what you do best, what you value, or what you originally agreed to do. You may still be performing well. In some cases, that is part of the problem: you have become useful for work that does not fit you, and you don’t feel respected.

Common pushes:

• Being underused or miscast

• Watching your responsibilities move away from your strengths

• A growing gap between your values and the company’s

• Feeling unchallenged or bored

• Not seeing a clear place to grow inside the organization

Common pulls:

• Work that uses your full capabilities

• Greater alignment with your values

• Recognition that matches your contribution

• A role built around the things you do unusually well

Quest 4: Take the next step

You have completed something meaningful, mastered the role, or reached a point where the work no longer stretches you. Alternatively, you’ve hit a personal milestone (baby, move, etc.) and want a change. You are not necessarily unhappy. You are simply ready to be challenged and get the support you need to grow.

Common pushes:

• Hitting a personal or professional milestone

• Feeling unchallenged or bored

• Not seeing a clear place to grow

• Needing to provide more support for family or loved ones

Common pulls:

• Feeling like a job is a clear step forward

• Joining a tight-knit team you can count on

• Developing new skills as part of a stepping stone to something else

A quick quest diagnostic

Finish this sentence: More than anything, I need my next move to…

• Get me away from a situation I can no longer tolerate.

• Give me control over my time, workload, or life again.

• Let me do work that fits my strengths and values.

• Give me a new challenge or chapter.

How you finish the sentence will not capture every part of your situation, but it will usually reveal which quest you may be on—and also help you label what you don’t need right now.

3. Which work brings out my best?

Most professionals know their skills better than they know the conditions that allow them to do their best work. You take on responsibilities, become known for certain outcomes, develop valuable skills, but are often too busy doing the job to understand the circumstances you need to be successful and feel fulfilled.

Then a shiny title or compensation increase appears, and you accept a role that actually makes you miserable—an outcome common to ICs-turned-managers who realize too late how much they hate management.

You need to figure out what you need before you switch jobs (or are compelled to switch), not figure it out by switching. This is what building your energy profile is all about: it provides a blueprint for evaluating new opportunities, along with a starting point for questions you can ask a hiring manager or peer as you explore open roles.

Build your energy profile

To get started, grab some Post-it notes or spin up a Miro board, and make a simple timeline of roles you’ve held and the title, company, and duration for each role (including your current role if employed). If you want a pre-built template, we’ve got one here. The steps below will show you how to fill this out, and I’ve included an example of the beginnings of my own energy profile:

Step 1: Audit your calendar

Pull up the past month of your work calendar and list what you actually did, hour by hour.

Do not use the language of your job description. Describe the activity:

• Collaborative planning meeting

• Individual research

• Customer call

• Writing a strategy document

To help you through this, you can integrate your calendar with an AI agent of your choice (via a simple connection or MCP) and use this simple prompt:

“For the past month, make a list of core meetings and time blocks on my calendar and ask me 1-2 questions about each to uncover what I actually did during those blocks of time. For example, if you see a ‘team meeting,’ ask me briefly what my role was and how I contributed. Then produce a list of the 8-10 core activities in my work life.”

Step 2: List your energizers

Which tasks energized you?

Look for work where you lost track of time, volunteered extra effort, or kept thinking after the meeting ended. Include the tasks that left you with more energy afterward.

Step 3: List your drainers

Which tasks did you avoid, postpone, rush through, or perform adequately just to get them over with?

Include work you are good at but dislike. Competence and energy are not the same thing. Many careers get built around things a person does well but does not want to keep doing.

Step 4: Repeat the exercise across previous jobs

Review your last job, then the one before that. You can’t go hour by hour, but for each role there were likely six to eight core responsibilities or tasks you engaged in on a regular basis.

As you complete this, you will begin to see a history of your career written in the language of energy instead of titles or responsibilities.

Step 5: Identify themes among your energizers and drainers

Revisit the activities you collected in the last step and see if you can identify broader themes or clusters that emerge from tasks that energize and drain you. As you do this, clarity is key. “Working with others” is not a clear theme. Neither is “heads-down work.” Working with whom? On what? Under which conditions? Similarly, “office politics” is not a clear theme for what drains you. What relationship dynamics are problematic? What decision-making processes don’t work for you?

To help you do this, you can ask questions like:

• What is this more like?

• What is this less like?

• Which conditions need to be present?

Below is an example of unpacking a theme that emerged when I built my own energy profile: “environments that allow me to become an expert at the intersection of people and technology.”

As your themes begin to emerge, you’ll realize where you shine, where you check out, and what you want out of your next role. This is the foundational work necessary to begin prototyping potential opportunities.

4. What possible moves should I explore?

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2026-08-24 23:02:23

Grok Bot + Grok 4.6—what’s great (and what’s still hype)

Brought to you by:

Bolt.new—Turn your idea into a real product

Jira AI SDLC—Get your tokens’ worth with Jira

In this solo episode, Claire tests Grok Bot, Cursor Origin, and Grok 4.6 to figure out what’s genuinely useful and what’s still mostly hype. She shares the Grok Bot feature that immediately won her over, why she isn’t ready to replace GitHub with Origin, and how Grok 4.6 performed against GPT-5.6, Claude Sonnet 5, and Opus 5 in her own blind evaluations.

Biggest takeaways:

1. Grok Bot’s multi-account connectors solve a problem every other agent platform seems to ignore. Most platforms assume each person has one Gmail account and one Slack workspace. Claire has four email addresses and seven Slack workspaces. Grok Bot lets her connect all of them to a single bot, which made it genuinely useful from day one in a way that Codex and Claude still have not matched.

2. Grok Bot’s simplicity is both its greatest strength and its biggest limitation. Setup is fast, the iMessage-style interface is clean, and the built-in plugins actually work. But people who enjoy customizing their agents, choosing models, shaping personalities, and tinkering with every detail may find it almost too polished. Claire loves her OpenClaw agents partly because they are chaotic and high-maintenance. So far, Grok Bot has not given her much to wrestle with.

3. Cursor Origin is a compelling vision that is not quite ready for prime time. An agent-native alternative to GitHub makes a lot of sense, especially one where Bugbot, Cursor, and the entire pull request workflow are designed around how coding agents actually work. Today, though, Origin still feels like a more attractive version of GitHub with fewer features. Teams that rely heavily on GitHub Actions, code owners, and existing automations will need a much stronger reason to migrate.

4. Grok 4.6 is a genuine frontier-model competitor. That conclusion did not come from someone else’s leaderboard. Claire runs her evaluations blind, grades the outputs herself, and gives her own judgment 70% of the final weight. Grok 4.6 finished alongside GPT-5.6 Sol at the top of the Claire Index, ahead of both Sonnet 5 and Opus 5.

5. For sharp, enjoyable agent conversations, Sonnet 5 is still the model to beat. When Claire wants an OpenClaw agent that is concise, responsive, and fun to talk with, Sonnet 5 continues to win. It has a conversational rhythm that feels more like working with a strong collaborator than issuing commands to a tool. Grok 4.6 does not yet compete in that category.

6. Cursor and xAI are assembling a surprisingly coherent enterprise stack. Grok Bot serves knowledge workers, Origin handles code hosting, Grok 4.6 provides a capable default model, and the Cursor IDE already sits at the center of many developers’ workflows. None of the pieces is perfect on its own, but together they are beginning to look like a credible enterprise platform. Large companies often prefer one vendor that can own the entire experience, and Cursor is increasingly positioned to become that vendor.

I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)

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Ryan Carson is a five-time founder and the solo founder of Untangle, a B2B SaaS platform for family law firms. In this episode, he breaks down how he manages up to 15 AI agents at once, ships as many as 40 pull requests a day, and uses Devin, Codex, and Claude Code to handle everything from engineering and QA to customer success and investor updates. He also shares why more AI output doesn’t necessarily lead to a better product, how a handwritten priority list keeps his agents focused, and why talking to one real customer changed the direction of his entire company.

Biggest takeaways:

1. The most important skill for a solo founder may be managing agents, not writing code. Ryan runs 10 to 15 Devin threads at once, organized into P0, P1, P2, and Bugs folders. He treats each thread the way a good manager treats a direct report: give it a clear goal, set the right priority, and avoid unnecessary hand-holding. That organizational discipline is what separates founders who gain real leverage from AI from those who simply accumulate open tabs.

2. A piece of paper can still be the best tool for protecting attention. Despite working across eight screens, Ryan keeps a handwritten list of his weekly priorities beside him. The simplicity is intentional. When agents are constantly generating updates, questions, and decisions, that physical list keeps him anchored to the three things that matter most before he gets pulled into whatever Devin surfaced overnight.

3. Ryan built an AI playbook that functions like a customer success team. His Watchdog workflow reviews every law firm account, pulls recent activity and errors from Sentry and internal logs, identifies the three most important problems, and checks whether a recent pull request has already fixed each one. Everything appears in a single Devin thread. Whenever Ryan feels the familiar anxiety of not knowing what is happening across his customer base, he runs Watchdog and quickly gets back up to speed.

4. Producing more with AI does not automatically lead to a better product. Both Ryan and Claire are skeptical of letting agents work without constraints overnight. Frontier models can generate an enormous amount of output, but they do not know what customers actually need. Product ideas, priorities, and market judgment still have to come from a human who talks to users. Ryan found product-market fit for Untangle not by shipping more code but by landing one meeting with family law attorney Renee Bauer and listening carefully.

5. Cloud agents may handle most engineering work, but Codex still shines when the frontend requires close attention. Ryan uses Devin for cloud-based work across bugs, pull requests, investor updates, and customer triage. He turns to Codex when a feature is visually complex and he needs to stay close to the implementation. The distinction is not about loyalty to a particular tool. It comes down to latency, browser access, and the ability to inspect and refine the interface in real time.

6. Coding agents can operate far beyond the codebase. Claire uses Devin for deal desk, custom quotes, and customer triage. Ryan uses it to prepare investor updates through a reusable skill. Both approach these agents with a broader question: What could someone accomplish if they understood the entire codebase and could write software to solve almost any problem? That framing reveals business uses that would never emerge from treating an agent as a simple coding assistant.

7. The best engineering interview may be a screen recording of the actual work. Ryan asks candidates to record themselves building a feature inside an existing application, with the entire screen visible and no introductory meeting required. In the next stage, he gives them access to Devin and reviews the replay of how they worked with it. This shows him how candidates think, build, and manage an agent under realistic conditions, which he finds far more revealing than a typical behavioral interview.

8. The strongest design workflow pairs Claude’s system thinking with Codex’s implementation ability. Claire used Claude Design to break a Figma file into reusable design tokens and a design.md specification. She then gave that specification to Codex, which created shared components across a monorepo. Claude is particularly good at translating a visual system into a portable spec. Codex is better at turning that spec into working, interconnected code. The workflow succeeds because each model is assigned the part it does best.

If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.

Catch you next week,
Lenny

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