The Best Career Decisions Often Start as Bad News

The Best Career Decisions Often Start as Bad News

by | Aug 6, 2026 | 0 comments

Episode 257 | Watch on YouTube | Listen on Buzzsprout

Last week, I got bad news on a virtual call: my university is cutting summer teaching, which means losing about $50,000 a year in income. And instead of panic, my first reaction was relief.

This isn’t a leadership-failure story — I’m part of that leadership. The real issue was that other stakeholders needed to be in the room before the decision could be made well. Once they were, the meeting moved fast, and something unexpected happened: within twenty minutes, the conversation went from bad news to opportunities we’d been ignoring, or hadn’t had the resources to pursue — and whether resources could be reallocated toward the parts of the business with a real future.

That pivot is built on a question I borrowed from Dan Miller: What does this make possible? It doesn’t pretend bad news isn’t bad. It just refuses to stop there. I apply the same question to an unrelated situation my organization is dealing with right now — a legal dispute with the power company — and find real opportunity even inside a frustrating, costly process. I tie the idea back to Romans 8:28: even hard things can be pointed somewhere useful.

This shows up anywhere change is happening — a reorganization, AI reshaping your work, an industry that’s stopped growing, or just losing the excitement you used to feel on Monday mornings. Most people already know more than they admit. The real question isn’t whether change is coming. It’s whether you’ll build options before someone else decides for you.

Key Points

  • This is not a leadership-failure story — the real gap was other stakeholders not being involved soon enough.
  • Bad news, once it’s finally out in the open, can free a group to move fast toward real opportunities.
  • The question, “What does this make possible?” (credit: Dan Miller) shifts a conversation from loss to opportunity without denying the loss.
  • I apply the same question to any hard situation, and I give a live example with an ongoing legal dispute with my power company.
  • The hardest part of a career change is usually the waiting, not the news itself.
  • The real question is whether you build options before someone else decides for you.

Three Questions to Sit With

  • If nothing changed over the next three years, would you honestly be happy?
  • What could you begin building today that would give you more options tomorrow?
  • If bad news arrived next month, what would you wish you had already started?
  • Whatever situation you’re in right now — what does this make possible?

Next Step

If this episode has you thinking about what you’d want to have started, grab the free Moving Past Obstacles resource below. It’s built to help you take the first concrete step.

Listen to the episode above or find it on your favorite podcast app.



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About the Author

Dale Callahan

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