The Radio Free Hillsdale Hour

Episode: Dana Perino Shares Life and Career Advice
Host: Scott Bertram
Guest: Dana Perino (Fox News Host, Former White House Press Secretary, Author)
Release Date: April 25, 2025

Episode Overview

In this episode, Scott Bertram interviews Dana Perino about her new book I Wish Someone Had Told Me: The Best Advice for Building a Great Career and a Meaningful Life. The conversation explores themes of mentorship, curiosity, adaptability, time management, and authentic networking in professional and personal development. Dana shares anecdotes from her White House days, advice from her book’s contributors, and practical wisdom for listeners at any stage of their career.

Key Discussion Points & Insights

Origins and Purpose of Dana Perino’s Book

• Genesis of the Book
  • Dana’s book evolved from a popular FoxNews.com feature “Short Questions with Dana Perino,” which highlighted the personal and professional lives of her colleagues.
  • Over time, she shifted focus to deeper questions about the best advice people have received or their lucky breaks ([02:16]).
  • She tapped over 40 friends and colleagues, including both well-known personalities and lesser-known but influential figures.
• Inclusive Audience
  • Inspired by her mother’s wish—“I wish someone had told me all of this”—the book is not limited to young women but meant for everyone seeking guidance ([03:56]).

The Joy and Power of Mentorship

• Dana emphasizes the personal fulfillment she receives from mentoring young people.

• She reflects on the importance of expressing gratitude to mentors from early in her life (including her first-grade teacher), and the unexpected impact mentors have ([05:11]).

  “Sometimes you mentor people and don’t even realize it…to see a little bit of worry taken away from their shoulders after they leave my office, that does make me feel really good.” — Dana Perino [06:47]

• Career-focused mentoring often turns personal, as mentees seek guidance on finding meaning beyond work ([06:10]).

Cultivating Curiosity and Lifelong Learning

• Dana identifies curiosity as a key differentiator in success and stresses “ABL—Always Be Learning” ([07:44]).
  • She provides practical advice: leverage podcasts, YouTube, reading, and everyday conversations to spark learning.
  • Curiosity is repeatedly highlighted by contributors like Mike Rowe and Bill Hemmer as vital to career growth.

  “Somebody who is curious is always more likely to get the job or the promotion than people who aren’t.” — Dana Perino [08:50]

Navigating Mixed Career Advice & Pursuing Passions

• The book features contrasting advice:
  • John Roberts: “Don’t let anyone tell you you can’t achieve what you are passionate about.”
  • Greg Gutfeld: “Do not follow your dreams. That’s terrible advice.” ([09:06])
• Dana shares her own pivot from aspiring gymnast to championing communication through speech and debate, illustrating that dreams can evolve and new passions discovered through skills development ([09:41]).

  “Dreams can change…finding a skill that did help me achieve something else that I wanted to do, which was communication and journalism—being on the speech team was a big part of that.” — Dana Perino [10:56]

Discovering Your “Secret Sauce”

• Dana, pressed for her own unique differentiator, admits to being skilled at “managing up”—anticipating a boss’s needs and earning trust ([12:56]).

  “Learning how to manage up and anticipating your boss’s needs and getting ahead of problems for them, making their life easier, setting them up for success…I am really good at that and I take a lot of pride in it.” — Dana Perino [13:12]

• She recalls President Bush’s confidence in her briefing skills during her White House tenure.

Careers in Transition and Embracing Change

• The episode addresses today’s norm of career mobility and “job-hopping.”
• Dana shares stories of colleagues and friends whose winding career paths (e.g., Martha MacCallum’s shift from aspiring actress to news anchor) showcase the value of transferable skills ([14:57]).

  “All the skills that you have in your life build upon each other.” — Dana Perino [15:13]

• Sometimes, persistence through adversity (“staying for a turnaround”) can be rewarding, as in the story of Lauren Fritz at WeWork ([16:46]).

Intentionality and Time Management

• Both Dana and Scott stress the necessity of “planning to be busy” ([17:39]).
  • Dana advocates for technique: scheduling even personal time, booking exercise in advance, and following a rule of “only one weeknight engagement per week” to foster balance ([18:18]).

  “Human beings actually do like a routine…I have to be super intentional about my time.” — Dana Perino [19:25]

  • She encourages students interested in media or politics to study broadly, not just in their intended field.

Authentic Networking

• Dana discusses post-COVID networking challenges, advocating for intentional socializing to offset isolation ([21:11]).
  • Making connections by being genuinely curious about others’ backgrounds (travel, education) helps keep networking authentic and mutually beneficial.
  • She notes the importance of following up and offering help, not just seeking favors ([22:41]).

  “As your career grows, you find that it helps you help others...Making connections like that is super satisfying.” — Dana Perino [22:47]

Notable Quotes & Memorable Moments

• On the importance of gratitude and mentorship:

  “One of the things I realized in this book is that I should have thanked more of my mentors along the way.” — Dana Perino [05:24]

• On being intellectually nimble:

  “I listen a lot while I’m walking, while I’m doing the laundry... I’m always learning.” — Dana Perino [08:08]

• On the myth of a single lifelong career:

  “There are so many different ways to change careers...all these things can happen within a corporation.” — Dana Perino [15:45]

• On the discipline of time management:

  “I wanted for so long to be a person who could be more laissez-faire about my schedule. But one, it’s just not in my nature.” — Dana Perino [18:55]

• On improving networking:

  “You really have to be intentional...to make networking feel like it’s not so stifled, be curious about other people...” — Dana Perino [21:11]

Important Segment Timestamps

| Timestamp | Segment/Topic | |-----------|-----------------------------------------------------------| | 01:27 | Introduction to Dana Perino & her new book | | 02:16 | How “I Wish Someone Had Told Me” came together | | 05:11 | Dana on the joy of mentorship and importance of gratitude | | 07:44 | The role of curiosity and lifelong learning | | 09:06 | Navigating mixed career advice about passion vs. pragmatism| | 12:56 | Dana’s “secret sauce” — the value of managing up | | 14:57 | Advice for a generation anticipating frequent job changes | | 17:39 | Balancing ambition with life: time management insights | | 21:11 | Best practices and philosophy for authentic networking |

Tone & Style

Throughout the conversation, Dana Perino combines humility and humor with practicality and encouragement. She draws from her own formative experiences as well as offering the shared wisdom gathered from a diverse array of mentors and colleagues. The tone is energetic, approachable, and retains Dana’s self-effacing wit and optimism.

For Listeners

This episode is a rich resource for students, new graduates, professionals navigating career change, and anyone interested in actionable advice on building a gratifying career and life. Dana’s stories and gathered advice offer inspiration and concrete strategies, all delivered with the perspective of someone who’s been at the very top—and still values learning from everyone she meets.