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Learn from this investor’s $100m mistake

In 2010, a Grammy-winning artist passed on investing $200K in an emerging real estate disruptor. That stake could be worth $100+ million today.

One year later, another real estate disruptor, Zillow, went public. This time, everyday investors had regrets, missing pre-IPO gains.

Now, a new real estate innovator, Pacaso – founded by a former Zillow exec – is disrupting a $1.3T market. And unlike the others, you can invest in Pacaso as a private company.

Pacaso’s co-ownership model has generated $1B+ in luxury home sales and service fees, earned $110M+ in gross profits to date, and received backing from the same VCs behind Uber, Venmo, and eBay. They even reserved the Nasdaq ticker PCSO.

Invest for $2.90/Share

_{Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.}

Few moments rattle a manager quite like the sudden resignation of a valued team member. One day, everything seems business as usual, and the next, there’s an email in your inbox that starts with “I’ve really enjoyed my time here, but…”

While it may feel sudden, departures rarely happen overnight.
The decision to leave is often a slow burn—an accumulation of frustrations, unmet needs, or simply the lure of a better opportunity. By the time an employee hands in their notice, they’ve often been mentally and emotionally disengaged for weeks or even months.

The tricky part? These warning signs aren’t always loud.
They can be subtle—masked behind politeness, routine work, and an “I’m fine” smile.
But if you know what to watch for, you can spot the early indicators and intervene before it’s too late.

Let’s walk through four of the most telling signs that someone on your team may already have one foot out the door—and what you can do when you see them.

4 signs to be aware of

1. Disengagement and withdrawal

2. Spike in absenteeism and reduced responsiveness

3. Behavioral shifts

4. Evidence of job search activity

Disengagement and withdrawal
In healthy teams, people don’t just do the work—they bring energy, curiosity, and connection. So when someone who used to contribute ideas, joke in Slack, or stay engaged in meetings starts pulling back, take note.

Withdrawal often begins small:
•They stop volunteering for new projects.
•They avoid social moments like coffee breaks or team lunches.
•Their updates become minimal and transactional.

Over time, the disengagement becomes harder to miss. They might turn cameras off during virtual meetings, skip optional gatherings, or contribute only when directly asked.

Why it happens: This could be burnout, a mismatch of role and skills, a conflict with colleagues, or simply a loss of faith in the organization’s direction.
It’s also possible they’ve mentally committed to leaving and see no benefit in deepening bonds they’ll soon break.

What to do:
•Check in privately—not to accuse, but to understand. A simple “I’ve noticed you seem quieter lately. How are you feeling about your work?” can open the door.
•Look for re-engagement opportunities—perhaps they need a fresh challenge, more recognition, or a role adjustment.

Disengagement is rarely random; it’s usually a symptom of an unmet need.
Addressing it early can turn a “goodbye” into a renewed “I’m in.”

Spike in absenteeism and reduced responsiveness
If someone’s calendar suddenly fills with “private” appointments, they’re leaving early more often, or sick days creep up, it’s worth asking why.
While legitimate life events happen, a noticeable pattern of absence can point to job interviews, networking events, or simply a growing detachment from the team’s daily rhythm.

Reduced responsiveness is another tell. That person who used to reply quickly to emails now takes hours—or days. Meeting invites are declined more often.
Updates are shorter and less detailed.

Why it happens: An employee who’s in “exit mode” may be prioritizing external commitments over internal ones.
They might also feel less urgency to respond because they’re no longer emotionally invested in outcomes.

What to do:
•Avoid jumping to conclusions—ask first if something personal is affecting their availability.
•If patterns persist, frame the conversation around impact:
“I’ve noticed it’s been harder to reach you lately, and it’s affecting the team’s ability to move forward.”
•Offer flexibility if there’s a genuine need—but be transparent about performance expectations.

Remember: an employee who’s already disengaged mentally will naturally become less present physically.

Behavioral shifts
A sudden change in how someone shows up—both literally and figuratively—is a classic signal. This can look like:
•A consistently punctual person now arriving late.
•A usually meticulous employee making careless errors.
•A once-polished team member showing up with less attention to dress or presentation.

But it’s not just about surface-level appearance. Attitude shifts are often more revealing. Someone who used to take pride in ownership might start doing the bare minimum. They may avoid committing to long-term projects (“Let’s see where things are in a few months”) because they know they won’t be there to see them through.

Why it happens: When someone’s sense of belonging or purpose is gone, so is the motivation to uphold their best habits. They’re less concerned about impressions because they’ve mentally detached from future evaluations or promotions.

What to do:
•Treat changes as a signal to explore—not to reprimand.
•Revisit their workload—sometimes what looks like apathy is actually exhaustion.
•Make space for honest dialogue: “You’ve always taken such pride in your work, but lately I’ve noticed some changes. What’s been going on?”

Sometimes, this conversation reveals fixable frustrations.
Other times, it confirms the employee is already past the point of return—but at least you’ll know.

Evidence of job search activity
Some signs are subtle. This one isn’t.

If an employee’s LinkedIn profile suddenly gets a professional glow-up, they’re connecting with recruiters, or you catch them taking calls in the parking lot, it’s a strong hint they’re preparing to move on.

Even less obvious signs—like signing up for new professional certifications or attending unrelated industry webinars—can indicate preparation for the next chapter.

Why it happens: Employees seek change for many reasons—career advancement, better pay, relocation, or simply the desire for a new challenge.
Once they’re actively preparing, they’ve already started detaching from your organization.

What to do:
•If you value their contribution, don’t wait—have a career development conversation now. Ask: “What would make this role more aligned with your goals?”
•If you can’t offer what they’re looking for, it may be wiser to support a respectful transition than try to block it.

It’s not always possible—or wise—to compete with a better opportunity.
But knowing early allows for smoother succession planning.

In conclusion

Spotting the signs is only the first step.

What you do next matters even more:
1. Stay curious, not confrontational. Jumping to accusations can damage trust with someone who may still be on the fence.
2. Open communication channels. Regular, honest one-on-ones make it easier to surface issues before they become resignation letters.
3. Invest in retention proactively. Recognition, career development, and a healthy culture aren’t just nice-to-haves—they’re your best defense against turnover.
4. Plan for graceful exits. Even when retention fails, handling departures respectfully maintains your reputation and leaves the door open for boomerang hires.

Losing a good employee is expensive—not just in recruitment costs, but in lost expertise, team disruption, and cultural impact.
Yet in most cases, the warning signs were there all along.
By learning to spot disengagement, absenteeism, behavioral shifts, and signs of active job hunting, you give yourself a chance to change the story. Sometimes, that means re-engaging the employee and helping them rediscover purpose. Other times, it means preparing for a smooth, respectful handover.

Either way, the goal is the same: be an attentive, proactive leader who sees the road ahead—not one who’s left wondering, “Why didn’t I see this coming?”

Thank you for reading.