Congratulations, you're in can-do Groundhog Day

The unofficial survival guide for helpful engineers and over-accommodating leaders.

There’s a particular kind of person every team praises, engineers, tech leads, managers alike.

The can-do ones.

The people who jump in, fix the thing, patch the gap, keep the train moving.
They’re helpful, resourceful, fast. They don’t just solve problems, they radiate competence while doing it.

“Be useful” is the motto.
“Be helpful” the identity.

And it works beautifully… until it doesn’t.

The trouble starts when you’re held responsible for consequences you never had the authority to prevent. Suddenly your can-do and your how-you-do matter far more than your willingness to help.

This isn’t just an engineer problem. Leaders fall into the trap even faster.

We MacGyver our way through broken processes, duct-taping loopholes just to keep people unblocked, and before long, we’ve been promoted to elite arsonist-firefighters, bravely extinguishing flames we never started… but somehow kept alive through sheer helpfulness.

That’s where the loop begins.

Because every time you rescue the system, the system learns it can hand you the same kind of problem again.
And again.
And again.

Just like Groundhog Day, nothing changes until the person inside the loop changes how they respond.

If you haven’t seen the movie: Groundhog Day is a story about a guy reliving the same day on repeat until he responded differently — a near-perfect metaphor for what happens when systems keep handing you the same problems.

Where the helpfulness trap begins

You get a message into your DMs:

“Any chance you could squeeze this in? It shouldn’t take long.”

You already know it won’t fit, it’s not scoped and that the timeline is fantasy.

But you also know this:

You want to be supportive.
You want to be collaborative.
You want to avoid becoming “that engineer,” or “that leader“, the one who always pushes back.
You want to be seen as the person who gets things done.

So you say yes.

Not because the work fits, but because you’re trying to keep the team moving.

That’s where the trap tightens:

Saying yes feels like progress, but it often creates the very problems you later have to clean up.

That’s the myth of being helpful: the belief that saying yes makes you a good teammate or a strong leader.

But in reality, saying yes when you shouldn’t is the exact thing that undermines your reliability and trust.

Why we fall into the trap

We don’t over-accommodate because we like suffering. We do it because the incentives reward it.

The internal pressures:

• We want to be seen as collaborative.

• We don’t want to disappoint anyone.

• We want to be “easy to work with.”

• We don’t want to escalate small things.

• We’ve been rewarded your entire career for stepping up.

The external pressures:

• Everything feels urgent because nothing is truly prioritized.

• Work gets handed off without context.

• Multi-team projects create invisible dependencies.

• Fire drills and heroics earn more praise than disciplined planning.

• Being a “team player” quietly becomes synonymous with “absorbs chaos”.

Somewhere along the way, we start believing:

If I don’t say yes, I’m failing the team.

That belief is powerful.
It’s also wrong.

That belief drives a quiet erosion of boundaries.

Underneath all of that is the skill almost no one is taught:
assertiveness.

👉 Read more here Assertiveness: The survival skill

The hidden cost of being helpful

No one tells you this early in your career, but it’s true:

Helpfulness becomes harmful the moment it becomes invisible.

Over-helping produces a predictable set of failures:

1. You become unpredictable.

You say yes to things that shouldn’t fit, and now your commitments don’t match reality.

2. You burn trust.

People forget the request was impossible. They remember it slipped.

3. You train others to avoid prioritization.

If stretching always works, they assume capacity magically appears.

4. You take responsibility without authority.

You inherit work you had no power to renegotiate.

5. You inch toward burnout.

Quietly. Incrementally. One “sure, I can take that” at a time.

Systems route work toward the path of least resistance.
If you never resist, the system assumes you can hold infinite load.

And when concerns stay in private DMs, every tradeoff you’ve been swallowing stays invisible.

Cue the loop.

The Groundhog Day effect

Over-helping creates a loop: the system hands you the same kind of problem again because last time, you solved it without complaint.

Nothing changes because you keep rescuing the moment.

The cycle only breaks when the behavior changes — yours, not the system’s.

The 20/20 hindsight problem

A familiar pattern appears once something breaks, a bug, failed release, or a timeline slip that embarrasses someone one or two levels up.

Eventually someone asks:

“How did this get this far?”

Suddenly every risk becomes obvious.
Every late addition becomes a thing we shouldn’t have taken on.
Every fuzzy requirement becomes something we should have clarified.

And your quiet warnings?
The ones buried in a one-off DM?
Forgotten.

The pressure you were under?
Invisible.

The missing context?
Still missing.

The post-mortem question shifts from:

“How did we miss this?”
to
“Why didn’t YOU stop this?”

You’re judged on the outcome, not the conditions.

This is why boundaries, and especially public redirects, matter. They create shared accountability instead of private blame.

Private decisions → private accountability.
Public decisions → shared responsibility.

Why this is a system problem, not a personal flaw

It’s easy to blame yourself:

“I should have said no.”
“I should have pushed back.”
“I should have raised the alarm harder.”

But the trap is systemic:

• Work follows the path of least resistance.

• Capacity stays invisible if you never name it.

• People optimize around whoever absorbs the most without friction.

• Silence is interpreted as acceptance.

• A pressured yes is misunderstood as informed judgment.

No one intentionally overloads you. The system simply routes work to whoever doesn’t resist.

The shift: from helpful to reliable

Reliable people don’t say yes to everything. They say yes to the right things.

They:

• Show constraints early

• Ask what should move to make room

• Offer options instead of objections

• Surface risk before it becomes a thing on the retrospective

• Use public channels

• Document decisions cleanly

• Protect quality

• Choose clarity over temporary harmony

This is the shift from being liked to being trusted.

Reliability requires boundaries and boundaries require discomfort.

You do not become senior by absorbing more work. You become senior by making the work clearer, safer, and more predictable.

How to break the groundhog loop

1. Replace the reflexive yes with clarifying questions

• “What should we move to make room for this?”

• “Is this higher priority than X?”

Questions shift responsibility back to where it belongs: the decision-maker.

2. Don’t say no — redirect

Offer paths. Let them choose the cost they’re comfortable with.

Options A, B, C + your recommendation.

3. Make risk visible early

Say the uncomfortable thing before it becomes the expensive thing.

4. Move the conversation to a public channel

If it affects scope, timeline, quality, or another team, it belongs in public.

5. Document the decision

A single sentence is enough:

“We agreed to do X by date Y, understanding risk Z.”

It protects everyone and it demonstrates judgment. That’s how you build trust and a paper trail.

6. Redefine helpfulness

True helpfulness is clarity, not self-sacrifice.

The paradox of helpfulness

Saying yes keeps people happy in the moment.
Saying no keeps the work healthy in the long run.

The people who set boundaries become the ones everyone relies on.
The people who say yes to everything become the ones people worry about.

Groundhog Day doesn’t end when the world changes.
It ends when you change how you show up in it.

Your goal isn’t to be endlessly helpful.
Your goal is to be dependable.
To be trusted.
To be clear.

Because in the end:

Your yes only matters when your no exists.