I build systems executives use to decide. Writing on career & meetings. Ex Starbucks & Accenture. Seattle.
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Joined August 2006
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Your boss isn’t responsible for your career.
HR isn’t responsible for your growth.
Your mentor isn’t responsible for your next promotion.
Nobody cares about your success as much as you do. Act accordingly.
Folks who are better at representing their impact and the perception of that impact win.
Talent opens the door. Relationships invite you in.
When reaching out to people at your target company, drop the generic "can I pick your brain?"
Instead, lead with specific curiosity:
"Saw your post on the new project—curious how you entered that space."
Keep messages short, relevant, and focused on opening an actual conversation.
ALT Person holding a blue Mead 1-subject spiral notebook
Amazing resource
Announcing: Public compensation benchmarks for the most in-demand tech roles, now available for free on LennysJobs.com 💥
Pick a role and location, and get detailed base salary and new-hire equity benchmarks, from entry-level IC to Sr. Director. Data updated monthly.
To make this happen, I’ve partnered with @pavecomp, home to the world’s largest real-time compensation dataset, which pulls directly from the HR, payroll, and equity systems of 9,000+ companies (e.g. OpenAI, Databricks, Ramp, Cursor).
This is the first time Pave has opened up this data to everyone, and I’m excited to help more people get the comp they deserve.
Find it here: lennysjobs.com/comp
What's the difference between quitting and stopping?
Quitting is the abandonment of effort toward a result. A resignation. An end.
Stopping is a pause.
Restarting is implied. A break. A moment to recharge.
Then we begin again.
Informational interviews aren't just about getting a job. They're about genuine curiosity and building lasting relationships.
The main goal of an informational interview isn't to ask for an opening. It's to learn about the team, the culture, and the real problems they are trying to solve.
When you focus on understanding their challenges instead of pitching yourself, doors open naturally.
Waiting passively when you feel uncertain is a weak move.
The fix isn't to overthink or wait until you feel ready. The fix is to act.
Pick the smallest act you can control:
1. Run a tiny test
2. Note the results you get
3. Adjust and repeat
When you feel like you don't know, you need to take action and find out.
When I committed to writing every single day, the goal wasn't perfection.
It was three specific outcomes:
• Getting real-world feedback
• Creating a body of work
• Using a daily forcing function to build speed and consistency
Consistency in shipping is something you practice, not wait for.
ALT Vintage mechanical typewriter with paper loaded on wooden table
What's the difference between quitting and stopping?
Quitting is the abandonment of effort toward a result. A resignation. An end.
Stopping is a pause.
Restarting is implied. A break. A moment to recharge.
Then we begin again.
This is crazy work
seattletimes.com/business/mi…
"Microsoft is offering buyouts to about 60,000 employees, or roughly a quarter of its workforce, as the company tries to control its head count while avoiding layoffs."
Am I misunderstanding this or is the greater Seattle area cooked 😳
Strategic thinking comes down to connecting your daily tasks to the bigger picture.
See how your current work fits into the larger puzzle. Treat it like a map and actively explore the spaces that feel less familiar.
Don't just spot patterns—use what you notice to make one proactive adjustment.
Clarity comes from intentional focus.
Three things I hate at work:
- The ever-shrinking WFH days
- Group chats I never opted into
- In-person meetings canceled at the last minute
None of it is evil. All of it is one-way.
Take any situation you describe with "I'm not sure if..." and immediately run a test that challenges the assumption:
"I'm not sure I have enough experience." Try.
"I don't think I'd like it." Sample a bit.
"What if they say no?" Ask.
The trick is starting with the smallest act you can control. Pick a tiny test, note the results, and repeat.
Moving beats mulling.
Lead with curiosity, then follow up with value.
I once chatted with a PM about a challenge they mentioned. A week later, I sent an article addressing their issue. A month later, they referred me.
Authentic networking isn't a transaction. It's a conversation where you offer help before you ask for anything.
Most people treat AI like a magic button: enter a prompt, cross fingers, and wonder why the output is mediocre.
The technology isn't the bottleneck. The bottleneck is second-order thinking.
Most people react to what's in front of them, but rarely ask "What happens next?"
High leverage with AI isn't about prompt hacks. It's about mental clarity and asking better follow-up questions.
ALT Sean Oliver working at his desk looking at a monitor
