Why the Best Mentors Don’t Make Things Safer
It’s mentorship in the moments that matter.
Most people think mentorship is about advice. It’s not.
Mentors don’t make your path easier. They help you move forward faster and remain calm when the outcome is uncertain.
A mentor is a partner in your own growth, facing uncertainty with certain support.
I saw this clearly while mentoring a female executive through a salary negotiation.
She had been recommended for a new role by a former colleague. He shared the expected salary range and bonus structure. When the offer came, it was $30,000 lower, with half the bonus.
The good news? I was with her on vacation when she got the offer.
She knew what compensation was on the table. (Imagine if she hadn’t.)
What she didn’t know (yet) was how grounded she could be while asking for it.
She was uncomfortable—not just with asking, but with what came after.
The waiting.
The second-guessing.
The urge to soften her ask or simply accept less.
That’s where mentorship mattered most.
Not in telling her what to say, but in helping her hold her ground for what she knew she deserved.
She was thrilled the moment she got all of the salary, part of the bonus, and something harder to quantify: pride.
Pride in self-advocating, the same way she would for a direct report, a friend, or a colleague.
Pride in not standing in her own way.
These moments shape more than compensation.
They shape self-concept.
That’s the part people miss about mentorship.
A great mentor doesn’t remove risk; they push you toward it and help you stay steady while the outcome is uncertain.
Those experiences (asking, waiting, holding the line) change how people lead, how they show up, and how they see themselves over time.
Why Mentorship Still Matters (More Than Ever)
I’m grateful for the mentors who supported me as I try to pay it forward whenever I can.
Through mentoring senior HR leaders with Chicago SHRM, supporting founders and operators in growth environments through the University of Chicago/Alchemist Accelerator, and staying connected to former students as they navigate early-career crossroads, I see the same patterns show up in moments that matter:
Executives and founders carrying decisions where the cost of getting it wrong is high—and isolation is real
HR leaders holding both business risk and people impact, often without space to think
Early-career professionals navigating negotiations, job searches, and inflection points where one conversation can change confidence and outcomes
What connects all of this isn’t title or tenure, it is the uncertainty.
Mentorship moves people forward because it creates space to think clearly, test assumptions, and move with more confidence as we expand our comfort zone.
And when something doesn’t work? You recover smarter, not smaller.
That’s not a “nice-to-have”. That’s where you find your full potential.
See You in Austin
I’ll be mentoring at SXSW, and if you’re going (or know someone who is) I’m opening time for mentoring sessions.
This is a generous space to:
reflect on a real challenge
talk through something you’ve been avoiding
pressure-test a decision
or get some perspective on the way forward
A thoughtful conversation—with some Texas-sized clarity.
Schedule a mentoring session here:
SXSW booking
If you’re reading this after SXSW, mentoring and coaching sessions are available year-round, so reach out here instead.
Because sometimes one conversation can change the trajectory.
