Free Time with Jenny Blake

229: How (and When) to Trust Yourself and Others with Ilise Benun


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When we say trusting ourselves, which self are we talking about? Which parts of ourselves can’t be trusted?

That’s what we’re exploring today with returning guest, Ilise Benun. We discuss how confidence is a byproduct of action, what made her so angry that she decided to start her own business 35 years ago, building tolerance for silence and small experiments, and why she puts her phone number in her newsletter, on her website, and in the “from” line of her emails.

If you haven’t already, check out our previous conversation in episode 165: Are your clients bringing out the best in you? Engineering the Evolution of Your Business with Ilise Benun and episode 467 of Marketing Mentor on How to Free Your Time.

More About Ilise: Ilise Benun is the founder of Marketing-Mentor.com, the go-to online resource for creative professionals who want better projects with bigger budgets, through which she offers business coaching. She is also a national speaker and author of 7 books, including "The Creative Professional's Guide to Money," three online courses via CreativeLive and Domestika.org, and The Simplest Marketing Plan – all tailored to the needs of creative professionals. She has also been hosting the Marketing Mentor Podcast since 2008, with over 465 episodes at the time of this recording.


🌟 3 Key Takeaways
  • Drop the belief that “I need to know” — what I’m doing, what my niche is, have all the ducks in a row. Approach life and business as an experiment. You’ll know what’s not working much earlier than what is.
  • Absence blindness: we don’t see what’s not there, but in the silence things are happening
  • Be careful about taking advice from someone who has too much at stake in terms of the decisions you’re making.

    📝 Permission

    To listen to someone else. Find someone you trust, and just try something that they suggest—then see what happens.


    ✅ Do (or Delegate) This Next

    Make a list of various selves; for example, the old self vs. the new self; rational self vs. the irrational self; the critical self vs. the compassionate self; the morning self vs. the afternoon self. Note who you trust most with business decisions, and which ones might be better to sideline.


    🔗 Resources Mentioned
    • Ilise on the webTwitterLinkedInYouTube
    • Ilise’s Quick Tips newsletter (with Magic Money Formula)
    • PeopleTerri TrespicioJenn Lederer
    • Jenny’s Substack
    • ToolsVocaroo.com, LinkedIn mobile app, How to add LinkedIn’s audio intro (10 sec)

      📚 Books Mentioned
      • The Creative Professional's Guide to Money: How to Think About It, How to Talk About it, How to Manage It
      • Unfollow Your Passion by Terri Trespicio
      • Atomic Habits by James Clear
      • Free Time: Lose the Busywork, Love Your Business
      • Pivot: The Only Move That Matters Is Your Next One
      • Life After College

      • 🎧 Related Episodes
        • Ilise’s podcastMarketing Mentor
        • Free Time165: Are your clients bringing out the best in you? Engineering the Evolution of Your Business with Ilise Benun
        • 223: The Confidence Trap: Why You Don’t Need It to Do Big Things (SPARKED Crossover)
        • 133: Hire People Who Are Better Than You with Terri Trespicio
        • 185: How Licensing Helps Serve the Queen Bee Role + Stop Keeping up with the EntrepreJoneses with Mike Michalowicz
        • Pivot269: How to Stand Out When Everyone is Peddling the Same Sh*t with Terri Trespicio
        • 294: Confidence Conundrums and Attention Budgets with Terri Trespicio
        • 319: Who’s Sitting in the Board Room of Your Brain? With Adrian Klaphaak
        • 328: Accessing Your True Self Through IFS (Part One) and 332: IFS Part(s) Two—Understanding Our “Not Enough” Exiles with Adrian Klaphaak


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