Ten Thousand Miles

Vic Pepe

The road to success is full of hard work and determination. It is never easy - you just learn to handle hard... Here, I interview people who "make it look easy" but leave it all on the field daily to do so.

  1. Sep 1

    Why You're Not Lucky Yet (and how to fix it!)

    Luck, success, leadership, career growth, resilience, relationships, preparation, and opportunity. Vic Pepe explains why “lucky” people may not actually have more luck. They build a bigger landing pad for it. In this episode, I pull a lesson from my first book, The Lucky 13: The Definitive Set of Core Competencies for Great Leadership, and dig into something I've thought about for most of my career: What if you could actually increase your chances of getting lucky? I used to call myself “the luckiest guy in technology.” And I've absolutely had breaks I couldn't manufacture. I met the right people. Opportunities appeared at exactly the right moment. Doors opened that I couldn't have predicted. But that's only half the story. I believe luck becomes powerful when it meets preparation, resilience, relationships, timing, choices and the willingness to act. I share how a failed career in the music business led me to an $11-an-hour technology job, how one relationship helped change the trajectory of my career, and how relentlessly learning and expanding my skills eventually helped put me in the CIO seat. We also talk about why maintaining relationships for decades matters, why you have to take calculated risks before you feel completely ready, and why some of the worst breaks of your career can eventually become the moments you're most grateful happened. I also give you an exercise I've used for years: identify the 13 moments that made you who you are today. Don't just list accomplishments. Include the people, failures, decisions, accidents, opportunities, wins, losses and turning points. Then look for the pattern. You may discover that some of the moments you once considered incredibly unlucky were actually responsible for getting you exactly where you needed to go. You can't control when opportunity knocks. You can control whether you're home to answer the door. If this episode gave you something to think about, please subscribe and leave a comment, and share it with someone who could use this message. And tell me in the comments: What's one moment in your life that felt unlucky at the time, but turned out to be a blessing later? The Lucky 13 by Vic Pepe is available on Amazon in paperback, hardcover and eBook. Chapters 00:00 - Please Subscribe + What Does It Mean to Be Lucky? 03:05 - The Black Hawk Theory: Build a Bigger Landing Pad 04:36 - The Lucky Break That Changed My Career 09:19 - How to Create More Opportunities for Luck 11:45 - Relationships, Risk and Playing the Long Game 14:00 - When Bad Luck Is Actually Redirecting You 19:48 - The 13 Moments That Made You Who You Are 23:00 - How to Become “Luckier” in Life

  2. Aug 25

    It’s Tough Out There – Keep Going!

    Vic and JD share personal stories from their own careers, including moments when success suddenly turned into uncertainty. They explore why we attach so much of our identity to our jobs, why losing a role can feel like losing our value, and how to separate a temporary setback from the bigger story of who we are. They also dig into the realities of today’s job market, from AI-driven resume screening and recruiter ghosting to the power of relationships, referrals, and having people willing to make a phone call on your behalf. Most importantly, this is a conversation about confidence. How do you rebuild it? How do you create new evidence that you’re still capable? When should you ask for help? And what does it actually look like to support someone who’s sitting on the bench? If you’ve been laid off, pushed out, passed over, rejected, or you’re simply questioning what comes next, this episode is for you. You lost a job. You didn’t lose your value. CHAPTERS 00:00 — When Your Career Knocks You Down 05:09 — Your Job Is Not Your Identity 11:00 — Surviving Setbacks & Owning Your Story 23:38 — Confidence Is Built, Not Given 29:59 — The Job Search Is Broken 40:11 — Stop Applying. Start Working Your Network. 46:57 — Asking for Help & Actually Helping Others 56:39 — Your Setback Might Be Your Next Beginning Whether you’re actively searching for your next opportunity or helping someone who is, remember this: One bad chapter doesn’t erase the entire story.

  3. Aug 18

    The Buy vs. Build Trap: What I Wish I Knew as a CIO (earlier).

    Everyone faces embarrassing moments when starting out, but these experiences often shape our future trajectory. This discussion focuses on reframing failure and finding the value in those awkward early career lessons. If you feel stuck comparing your beginning to someone else's middle, this perspective on professional growth will help you reset your expectations. We explore why adopting a progress over perfection attitude is essential for long-term success. By looking at how minor setbacks serve as building blocks, you can approach your daily work with more confidence. Whether you are navigating your first job or pivoting to a new industry, embracing these career lessons helps you move forward without the weight of past errors. Subscribe for weekly career advice breakdowns, and let me know in the comments: what is one mistake you made that taught you a valuable lesson? Chapters: 00:00 – Intro: The Embarrassing Story From My First Strategy Meeting 04:47 – Why CIOs Don't Need a Team — They Need an Army 09:32 – The Data Doesn't Lie: IT Project Failure Rates 13:58 – AI Is Becoming a Commodity — Stop Trying to Build It 18:32 – The Real Cost of Building In-House 24:07 – How to Buy Smart: A Framework for CIOs Referenced in this episode: Vic's LinkedIn paper, "What I Wish I Knew as a New CIO." https://www.linkedin.com/posts/vic-pepe_a-30-year-look-back-activity-7490739364658860032-XeFX?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAB0zZUB4hhw7iJ4uEsh5eZZF3GNL-u_kIo

Ratings & Reviews

5
out of 5
7 Ratings

About

The road to success is full of hard work and determination. It is never easy - you just learn to handle hard... Here, I interview people who "make it look easy" but leave it all on the field daily to do so.