Navigating Setbacks
Setbacks in your career can take all kinds of forms – a layoff, a job that wasn’t the right fit, a missed opportunity, or a role that ended before you were ready. Often, you don’t realize it’s a misstep until it’s behind you. And once it is, you’re left to wrestle not only with what happened, but how it feel – and how others might see it.
But these experiences, as painful as they are, can become inflection points. The key is taking responsibility, learning what you can, and building habits or systems to keep you growing in the right direction.
In this part of The Orbit advice for navigating what comes after things don’t go as planned – from career detours and disappointments to second or third or fourth tries – and the lessons that only come from falling down and figuring out how to move forward.
Resilience Over Perfection
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Forget the glossy “bounce-back” clichés. Real resilience is messy, public, and rooted in curiosity. Sarah George-Waterfield interviews Tim Hanson, Nikki Galloway, and Emily Holdman about the moments that rattled their confidence – and how they used honesty, vulnerability, and a learn-on-the-fly mindset to emerge stronger. From a playwright-turned-investor to a perfection-prone CPA in public office, they reveal why credentials don’t guarantee success, perfectionism is exhausting, and progress often starts with the words: “I don’t know, but I’ll figure it out.”
Listen For …
Why majors ≠ destinies and how side-learning can outrun formal credentials
The link between vulnerability & trust, and how saying “I don’t know” accelerates growth
A practical framework for processing failure without losing confidence
Handling layoffs, tariffs, or any external hit by strengthening identity outside your title
How to teach (and model) resilience for teams, kids, and yourself
Timestamps
0:00 Intro — Gritty vs. Buzzword Resilience
1:04 Tim Hanson — Curiosity over credentials; liberal-arts detours; learning on nights & weekends
1:41 Nikki Galloway — From public auditor to PE CFO: vulnerability, imperfect days, and ditching exhausting perfectionism
6:25 Emily Holdman — Rebuilding confidence after stumbles, teaching her daughter (and team) to focus on “points on the board,” and coping when setbacks aren’t your fault
18:29 Closing Takeaways — Resilience as becoming, not bouncing backResources & Links
Article: When Plans Don't Work Out
Tim’s Newsletter: Unqualified Opinions
The Orbit Talent Network, Personality Test, & Roles: The Orbit
Feedback Loops & Friction Points
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Feedback isn’t failure – it’s data. In this episode, Sarah George-Waterfield explores the moments when work feels stuck, egos smart, and “What now?” hangs in the air. Danny Gray,Holly Grajera, and Emily Holdman break down how to invite critique before you want it, survive the sting, and build teams where mistakes are expected (and mined for insight). From a deal that fizzled to a cold-call grill-session gone sideways, they show why the right culture turns friction into forward motion.
Listen For …
“Seasonal” feedback: why the times you least want critique are when you need it most
How a humiliating first call became a career-long learning engine
Building shared-risk cultures where ideas are judged on merit, not ego
Practical scripts for asking targeted feedback right after a project – while details are fresh
Guardrails that let early-career talent experiment without wrecking trust
Timestamps
0:00 Intro — Friction Moments & Feedback Loops
0:58 Danny Gray — Permission, timing, and why “not wanting feedback” is a red flag
2:19 Holly Grajera — The grilled cold-call, learning to trust critique, and embracing gray areas
7:40 Emily Holdman — Early failures, idea-safe cultures, and keeping risk alive without wreckage
18:33 Closing Takeaways — Feedback as clarity, not condemnationResources & Links
The Orbit Talent Network, Personality Test, & Roles: The Orbit
Listen For …
Why majors ≠ destinies and how side-learning can outrun formal credentials
The link between vulnerability & trust, and how saying “I don’t know” accelerates growth
A practical framework for processing failure without losing confidence
Handling layoffs, tariffs, or any external hit by strengthening identity outside your title
How to teach (and model) resilience for teams, kids, and yourself
Timestamps
0:00 Intro — Gritty vs. Buzzword Resilience
1:04 Tim Hanson — Curiosity over credentials; liberal-arts detours; learning on nights & weekends
1:41 Nikki Galloway — From public auditor to PE CFO: vulnerability, imperfect days, and ditching exhausting perfectionism
6:25 Emily Holdman — Rebuilding confidence after stumbles, teaching her daughter (and team) to focus on “points on the board,” and coping when setbacks aren’t your fault
18:29 Closing Takeaways — Resilience as becoming, not bouncing backResources & Links
Article:When Plans Don't Work Out
Tim’s Newsletter:Unqualified Opinions
The Orbit Talent Network, Personality Test, & Roles:The Orbit
The Problem with Expectations
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Unspoken expectations are silent saboteurs. Sarah George-Waterfield talks Brent Beshore about the hidden gap between what we assume and what is. From cross-functional misfires to career-long “messy middles,” they share practical ways to surface assumptions early, press pause when collaboration derails, and treat surprises – good and bad – as feedback on your mental map.
Listen For …
Brent’s test: Where did reality deviate from my expectations and why?
Patience tactics for slow, grindy seasons when nothing seems to move
Timestamps
0:00 Intro — Expectations: the Invisible KPI
1:31 Brent Beshore — Living in the messy middle, patience vs. push, the email-fail apology
8:27 Closing Takeaways — Update your map before reality forces it
Resources
The Orbit Talent Network, Personality Test, & Roles: The Orbit
Feedback as a two-way street
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Everyone says they want feedback; few know how to make it land. Host Sarah George-Waterfield talks with Bryce Murray and Brent Beshore about building rhythms that make feedback normal, filtering signal from noise, and becoming the kind of teammate leaders want to be honest with. From monthly “anything I should apologize for?” check-ins to Brent’s goal of being “the easiest person on earth to critique,” this episode demystifies feedback culture for small-business teams.
Listen For …
Bryce’s taxonomy: content vs. personality feedback, and how to wear only what fits
Brent’s friction test: if people won’t tell you hard truths, you’ve already lost
Timestamps
0:00 Intro — Feedback: Easy in Theory, Messy in Real Life
1:09 Bryce Murray — Coding feedback type, owning what’s useful, discarding the rest
4:01 Brent Beshore — Lowering friction, earning permission, and the danger of “cobra incentives”
7:44 Closing Takeaways — Culture first, filters second, action third
Resources
The Orbit Talent Network, Personality Test, & Roles: The Orbit
“No plan panned out perfectly, but in almost all cases, negative surprises resulted in new opportunities and invaluable insights.”
“Pain grows in darkness and flees from light. We’re all battling something and battles aren’t won alone.”
— From Brent Beshore’s 2022 Annual Letter