Stretch With an Anchor
Take the role that will hurt you into growth — but only if one or two things in it are already in your wheelhouse.
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 89%
Lovinsky's answer to career selection is that predicting which company will succeed is nearly impossible, but predicting which role will stretch you is entirely possible — so optimize for growth and learning, and accept the pain that comes with it. The guardrail that keeps this from becoming self-destruction is an anchor: at least one or two important dimensions of the job where you can honestly say 'I got this,' giving you a foundation to stand on while you learn the rest.
Origin
Noam Lovinsky, on his career selection heuristic across YouTube, Thumbtack, Facebook and Grammarly. Lenny Rachitsky adds the Joseph Campbell line 'the cave you fear contains the treasure you seek,' and the flow-channel model (challenging but not too challenging) as related framings.
Core principles
- 01You cannot sniff out success with any degree of certainty — but you can develop a nose for people, and you can reliably identify what will stretch you.
- 02Growth and learning are painful, and the promised land is on the other side of the pain.
- 03Be wary of situations that are too net new — some competence anchor is what makes the pain survivable.
- 04Balance the stretch dimensions against the wheelhouse dimensions deliberately, not by luck.
How to run it
- 1
Stop trying to pick winners
Accept that predicting which company or product will hit is low-confidence. Redirect the energy you'd spend forecasting outcomes into two things you can actually assess: the calibre of the people and the size of the stretch.
Pro tip Develop the nose for talent deliberately — Lovinsky credits a strong first job out of school with teaching him what a high-functioning team feels like, a calibration hard to get any other way.
- 2
Find the situation that will force you to do things you haven't done
Actively seek roles that will stretch you and cause significant growth and learning. This is the primary selection criterion, and over the arc of a career it compounds better than optimizing for the safe fit.
Watch out Expect real pain. Growth and learning are not comfortable, and treating discomfort as a sign of a bad choice will make you exit exactly when the learning starts.
- 3
Decompose the role into stretch dimensions and wheelhouse dimensions
Break the job into its components — scale of team, product domain, required craft (design sense, analytical thinking, recommendation systems) — and mark each as 'stretch' or 'I got this.' Lovinsky's example: inheriting a very large team for the first time is fine, if the product area is one you know deeply.
Pro tip Two or three genuine 'I got this' components are enough. The anchor's job is to keep you standing, not to make the role easy.
Watch out A role where every dimension is net new has no foundation to keep you going while you learn — that is the specific configuration Lovinsky warns against.
- 4
Use the anchor to manage the pain, and know your limit
Lean on the strong dimensions to stay effective and grounded while you learn the rest. The anchor is what converts an unbearable role into a challenging one — and when there is no anchor left to lean on, that is the signal the discomfort has passed from productive to damaging.
Pro tip The flow-channel model applies: challenging, but not so challenging that mental and physical health take the hit.
Watch out Careers do end in burnout here. If you are losing health with nothing you can honestly say you're good at in the job, the stretch was miscalibrated, not insufficiently endured.
- 5
Weight it toward what actually fills you up
Lovinsky's overriding advice: do what you like, because you will simply be better at the things that genuinely fill you up. He declines to build a public presence — no newsletter, no tweeting — because it isn't authentic to him, and reasons that authentic strengths beat prescribed ones.
Pro tip Run an energy audit: track what gives you energy and what drains it, then bias your next role toward more of the former.
In the wild
Reporting to the CEO in the Creator role, Lovinsky was being asked questions that felt like they came from a different planet — a scale of strategic thinking he had not yet developed. Everything about the role was stretch and nothing was anchor.
→ He restructured the role rather than enduring it, moving under Hunter Walk, where he had the support to grow into the thinking he'd been missing — then eventually took on the viewer PM organization.
Despite advising Substack and operating at CPO level, Lovinsky doesn't tweet, write a newsletter or post — and openly wonders whether he's doing something wrong. His conclusion is that it just doesn't come authentically to him; he gets to know the industry by working with people and doing coffees instead.
→ A career spanning YouTube, Thumbtack, Facebook and CPO of Grammarly, built entirely on the work rather than on distribution — and, in Lenny's framing, a proof point that the best people are often the ones not spending their time posting.
Common mistakes
Taking a role where everything is net new
With no dimension you're already strong in, there is no foundation to keep you going while you learn the rest, and the stretch turns into a health-damaging grind rather than growth.
Optimizing for predicted company success
You cannot sniff out success with high certainty. Spending the decision on a forecast you can't make means neglecting the two variables you can actually read: the people and the stretch.
Doing the prescribed career activity instead of the authentic one
Chasing the tweeting/newsletter/networking playbook because it's supposed to lead to success is a poor trade if it doesn't fill you up. You'll be mediocre at it, and life is short.
Is it for you?
Best for
Mid-to-senior operators choosing their next role who can't predict which company will win and want a selection rule that compounds regardless.
Not ideal for
Anyone in a season where stability matters more than growth (health, family, financial constraint) — this framework deliberately buys pain in exchange for learning.
From the transcript
“And growth and learning can be very painful.”
“So just be be wary of situations that are like too net new.”
“There should be like a couple of those things where you're like, I got this.”
“You're you're generally going to be a lot better at the things that like really fill you up”
From the episode
The happiness and pain of product management
Noam Lovinsky (Grammarly, Facebook, YouTube, Thumbtack)