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Welcome to the jesse.blog audio
edition.

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I'm Jesse Friedman, and here I

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read my essays, leadership

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reflections, travel experiences,

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frameworks I'm building, and the

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ideas shaping my next book on the
open web.

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Let's get into today's essay.

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The hidden drags that undermine
team leadership effectiveness.

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In 2026, the difference between

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thriving and surviving will come

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down to efficiency, and I'm not

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referring to the obligatory

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mechanical kind powered by

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automation, which we are all going

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to have to adopt, but the human

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kind, the ability to lead a

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lightweight, focused team that

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cuts through challenges and adapts
to challenges on the fly.

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Yet most of us are unknowingly

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sailing with anchors that we don't

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even know we're dragging that

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undermine team leadership
effectiveness.

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The obvious disruptions are almost
comforting in their clarity.

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A key team member leaves,

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priorities get reshuffled up from

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above, a client crisis demands all
hands on deck.

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These feel like sudden dropping of
an anchor on a moving ship.

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Jarring certainly, but impossible
to ignore.

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You see them coming, you address
them head-on, you move forward.

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These burdens may be heavy, but

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they aren't subtle, and their very

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visibility makes them less
dangerous.

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It's the light, subtle

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distractions living in the shadows

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that will kill your momentum like

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plaque slowly forming on
artery walls.

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You won't notice how dangerous

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these distractions have become

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until they manifest in a major

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way: missed deadlines, burnt-out

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team members, or that creeping

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sense that despite everyone

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working harder than ever, you're
somehow accomplishing less.

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The half-knot of team leadership
effectiveness.

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Bruno Gianelli, the fictional

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character from West Wing,

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sometimes has difficulty talking

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to people who don't race sailboats

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because they lack substantive
experience with efficiency.

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In this clip, which is totally

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worth listening to, it's only a

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few minutes long, Bruno describes

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dragging kelp on a boat's hull,

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how that tiny bit of drag might
only cost you a half-knot of speed.

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Half-a-knot, barely noticeable,

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but in a race, you can't afford to
give up that half-knot.

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The ironic part of the story, and

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frankly why it's worth watching,

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is that he learned the hard way

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that the cr- he created more drag

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trying to remove the kelp than the
kelp was causing on its own.

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This is the job of a leader who

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runs an efficient team: not to be

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the one rowing, not to be the one

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adjusting the sails, but to be the

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one who notices and then corrects
the drag without overreacting.

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Your role is to empower your team

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to be the best versions of

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themselves, to combine their

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individual strengths into

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something greater than the sum of
its parts.

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But you can't do that if you're

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constantly compensating for hidden
imbalances and you haven't...

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that you haven't even identified.

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An imbalance that takes
you off course.

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Nearly 2,000 years ago, Seneca,

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Roman Stoic philosopher,

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statesman, and advisor to the

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emperors, wrote a series of
letters to his friend.

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These weren't abstract

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philosophical treaties, but

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practical wisdom from one leader
to another.

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In his 28th letter, Seneca wasn't

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writing about team dynamics, but
the metaphor translates cleanly.

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"How can you wander your travels,

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do you no good, when you carry

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yourself around with you? You are

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saddled with the very thing that

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drove you away." While Seneca was

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addressing personal emotional

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baggage, his next obs- observation
extends perfectly to team dynamics.

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"Like the cargo in a ship, which

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does not weigh her down unduly so

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long as it does not shift. But if

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it rolls more to one side than the

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other, it is liable to carry that

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side on which it settles down into

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the water. Whatever you do is bad

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for you, the very movement in

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itself being harmful to you since

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you are in fact shaking up a sick

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man." A slight imbalance forces
constant course correction.

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Over time, you stop taking
advantage of the wind entirely.

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Worse, if you require constant

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heading adjustments and something

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gets in the way of making those

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adjustments, before long, you're

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going to find yourself heading

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straight for treacherous rocky

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shores, and you won't even notice
until it's too late.

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It's not the weight of the ship
that endangers the ship.

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If it were, it wouldn't
get out of port.

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It's the imbalance.

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It's not the sudden dropping of
anchor, it's the subtle drag.

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These hard-to-see, hard-to-notice,

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hard-to-improve challenges to your

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efficiency are dangerous because

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they take you off course and slow
you down without your knowledge.

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And before you have time to

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compensate for it, you're deep

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into quarterly goals and
far off course.

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What to look for: Let me share

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three types of drag and imbalance

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I've encountered repeatedly, but

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I'm sure you have your own
examples.

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Please share your experience in

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the comments below where we can

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all share and benefit from group
experience.

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All right.

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The compulsive caller of all hands.

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This shipmate means well.

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They believe in transparency,

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collaboration, inclusion, but they

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call all hands on deck for every
minor course correction.

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Too many team meetings aren't just

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time sinks, they're momentum
killers.

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Shoot for less frequent meetings.

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My team does a morning- Monday
morning standup.

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In and out in 15 minutes.

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If we don't have a quorum, we
switch to async Slack update.

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Instead of recurring one-on-ones,

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try text-based check-ins and leave
space for video only when needed.

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However, the solution isn't just

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fewer meetings, but an emphasis on
strategic presence.

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When I bring a technical expert to

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a client meeting, I explicitly

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tell them, "Focus on your work. If

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a technical question arises, I'll

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reframe it and loop you in."They

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can be present without being

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constantly attentive, ready to

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engage when truly needed, but

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otherwise protected from the drag
of unnecessary contact switching.

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The boundary bender.

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The shipmate can't be, bear to
disappoint.

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When a, when a self-serve customer

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asks a question outside your SLA,

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your support SLA, they answer it

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anyway just this once, because
it's easy, because they care.

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Noble intentions, but possibly a
real drag.

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The reality is that other clients

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rarely suffer from this
over-extension.

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What happens instead is that your

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support person burns out trying to

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provide more than your system is
built to deliver.

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The cargo hasn't gotten heavier,
but it's shifted.

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Now your ship lists to one side

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and you're constantly correcting
course instead of moving forward.

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The key here is to be open and

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transparent with your clients, to

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be so abundantly obvious in what

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your SLA covers so it's never a

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surprise when you turn them

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towards documentation rather than
a bespoke response.

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Our team has extracted the most

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important points from our

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self-serve clients, for our

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self-serve clients to fully

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understand out of our TOS and into

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checkboxes that they have to
manually check.

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There are a half dozen of them,

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outlining their responsibility to

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the product, our brand, and their

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use of the product, making it very
clear to them.

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The omniscient observer.

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This ship nate- needs to know

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everything happening across the
entire fleet.

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Every product update, every

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strategic decision, every rumbling
from other departments.

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They attend every optional

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meeting, read every update,
subscribe to every newsletter.

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When someone at a conference asks

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about an unrelated product, they
feel obligated to have an answer.

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But here's what I've learned.

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Ignorance by design isn't just

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helpful for focus, it's a
superpower.

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When someone asks about a product

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I'm not involved in, I simply say,

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"I'm not close to that one, but I

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know who is." The key isn't
knowing all the things.

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It's knowing all the people.

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When you focus on building

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relationships with stakeholders

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rather than understanding the

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nuances of their projects, you
become more valuable, not less.

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You're moments away from any

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answer you need, but you're not

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carrying the weight of every
product or project on your ship.

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Plus, you have the added benefit

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of making connections between the

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people who are interested in the

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product or project with the person
who is most passionate about it.

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The captain's dilemma.

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Here's what makes these subtle
distractions so insidious to us.

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As captain, you'll find yourself

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constantly adjusting the helm to
compensate for the imbalance.

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A little to port here, a little to
starboard here.

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You might even get good at it, so

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good that you don't realize you're
doing it anymore.

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But this perpetual fine-tuning

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means you can never put the boat
on autopilot.

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You become afraid to take a real

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break, to fully unplug on

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weekends, to take that vacation
you've been postponing.

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After all, who else knows exactly

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how to compensate for that

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specific list your ship has
developed?

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This is how efficient teams slowly
become inefficient.

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Not through dramatic failure, but

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through the slow accumulation of
small compensations.

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And without time to rest and

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reflect, you become less aware of

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the growing drift, perpetuating

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the cycle until you find yourself

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in a tre- in treacherous waters,

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wondering h- wondering
how you got there.

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Rebalancing the load.

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The solution isn't to throw
everything overboard in a panic.

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It's to recognize that control,

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true control, comes from balanced

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distribution, not from personally
managing every compensation.

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When cargo appears on your ship,

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it's usually because someone
trusts you to carry it.

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They've seen your experience, your
wisdom, your capability.

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But being the best person for a

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job doesn't mean you should do it,

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especially if it's distracting you
from your main mission.

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You have three options.

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One, accept and rebalance.

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If this cargo truly belongs on

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your ship, find the right
place for it.

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Distribute the weight evenly so

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you can return to efficient
sailing.

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Two, decline with clarity.

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Some cargo simply doesn't belong
on your vessel.

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Say no clearly and kindly before
it unbalances everything else.

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Three, teach and transfer.

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This is a multiplier move.

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That cargo arrived on your ship

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because someone trusts your
expertise, so share it.

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Teach someone else to
carry this load.

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You'll be lifting all the ships in

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the port, and that person will be

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grateful not just for the

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knowledge, but for the trust and

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responsibility you've
placed in them.

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The art of efficient leadership.

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In the end, leading an efficient

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team isn't about moving faster or
working harder.

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It's about recognizing and

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eliminating the subtle drag that
keeps you from your natural speed.

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It's about having the wisdom to

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see not just the obvious anchors,

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but the hidden kelp, the shifted

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cargo, the small imbalances that
compound over distance.

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Seneca knew that we cannot escape

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what we carry with us, but we can

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choose how we carry it, where we

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place it, and when to hand it off

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to others who are ready to grow

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stronger by bearing their share,
their share of the load.

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The next time you find yourself

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constantly adjusting the helm,

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stop and ask, "What cargo has

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shifted? What drag am I

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compensating for instead of

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eliminating?" Because in the race

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to build something meaningful in

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2026, the winners won't be those
who row the hardest.

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They'll be those who sail the
cleanest.

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Your team is ready to fly across
the water.

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Our job is to cut loose everything

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slowing them down, even half a
knot, especially half a knot.

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Over the distance you're

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traveling, that half a knot is the
difference.

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This has been the
jesse.blog audio edition.

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I'm Jesse Friedman and thanks for
exploring these ideas with me.

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You can subscribe@jesse.blog and

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00:12:36,480 --> 00:12:38,603
join the monthly book club where

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we dive deep into a monthly topic

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and talk about how it shapes our
thinking.

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If this episode resonated with

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00:12:45,524 --> 00:12:47,726
you, feel free to subscribe to the

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podcast so you don't miss
the next essay.

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And as always, thanks for being

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here and for thinking
deeply with me.