Expectations, Second Chances, and What They Really Mean
This week, in my nonprofit work, we had a couple of participants who had to be let go from the jobs that we helped place them in.
It wasn’t a surprise, if I’m being honest. It was disappointing, sure—but not unexpected.
There had been warnings. Patterns. Gaps in soft skills that eventually turned into chronic lateness, taking breaks that stretched way past policy, lying about it, and finally—cursing at a supervisor.
It was one of those moments where the employer called us and, with a tone that balanced frustration and regret, said, “We just can’t keep them on anymore.” And they were right.
But here’s the thing: when you’re working with justice-impacted individuals—especially those under 25, those who’ve never had a job before, or those carrying the scars of childhood trauma—you can’t just hope for professionalism to appear fully formed. That’s not how this works.
Stealth Expectations vs. Realistic Ones
Brené Brown, in Rising Strong and Atlas of the Heart, talks about “stealth expectations”—those unspoken, often unconscious hopes or assumptions we have of people that we never actually communicate. Then when they’re not met, we’re shocked. Disappointed. Even hurt.
In reentry work, this can show up as expecting someone to just “know” how to act at work, how to regulate their frustration, how to respond to correction, or how to take accountability for mistakes.
But let’s be honest—where would they have learned it?
From the school system that pushed them out? From a family structure fractured by incarceration, addiction, or poverty? From prison, where following the “rules” often means something very different than in the workplace?
What Do We Really Mean by Second Chances?
We throw around phrases like “second chances” and “fresh starts,” but what do they mean when put to the test?
Does a second chance mean unlimited grace? Does it mean we ignore behavior that makes someone unemployable? Or does it mean we set realistic expectations, open doors, and walk with people long enough for them to build the muscles they never had a chance to develop?
To me, second chances look like this:
We teach. We don’t assume people know what “be on time” means. We show what it looks like, we practice it, we explain the why.
We re-teach. When someone slips, we don’t throw up our hands. We circle back. We have the hard conversation. We hold space for growth and for failure.
We support. Not just emotionally, but practically. Rides to work. A call before shift. A reminder about break limits. We scaffold success until it can stand on its own.
We let natural consequences happen. If someone is fired for cursing out a supervisor, that’s a real-world consequence. It’s not punishment—it’s preparation for life. And when that happens, we don’t shame. We reflect. We plan. We try again.
It’s Not About Lowering the Bar
Realistic expectations are not the same as low expectations. The difference is context.
We’re not asking less of our participants—we’re just recognizing how far they may have to travel to get there. And that journey isn’t always linear.
We build expectations on what we know: about brain development (hello, under-25 prefrontal cortex!), about trauma, about systems that have failed our participants long before they walked through our doors.
So when someone falls short, it doesn’t mean we were wrong to invest. It means the work continues.
We expect growth. We expect accountability. And we expect ourselves—as educators, mentors, employers, and advocates—to show up with both structure and compassion.
The Long Game
This work isn’t tidy. And it’s not quick.
But it’s worth it. Because sometimes, the participant who cursed out their supervisor today is the one who learns, grows, and leads others tomorrow—because someone saw the stumble, not as an end, but as a turning point.
Let’s stop being surprised by the hard moments. Let’s start being ready for them.
That’s what second chances really look like.
