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July 24, 2026

What If You’re Wrong About the Risk?

Issue 47

​

The Stories We Tell Ourselves

Inside this issue

  • The Fear Audit
  • Who Would You Be Without Your Concerns?
  • Time to Sprint: Does Your Calendar Agree?
  • What’s one area of your life where the story you’re telling yourself might be holding you back more than reality is?
  • Connect with Chris
  • Check out this week’s episode
  • The Last Laugh: Breath strips
  • But before we get to all that, here’s what’s…

On My Mind

video preview​

The older I get, the more I realize that fear changes its disguise.

When we’re younger, fear tends to be obvious. We worry about finding the right job, making enough money, proving ourselves, or figuring out what we want our lives to look like. But as we get older, those fears evolve. They often become quieter and harder to recognize.

This week’s guest, Chris Woods, spent years building a successful career that included leadership roles at Google before a near-death experience at age 40 forced him to examine what was really driving many of his decisions. What he discovered was something I think a lot of working dads will recognize. Fear wasn’t always showing up as fear. Sometimes, it showed up as ambition. Sometimes, it showed up as caution. And other times, it showed up as responsibility.

We talked about how many dads aren’t primarily afraid of failure anymore. We’re often afraid of losing what we’ve already built. Losing income. Losing momentum. Losing status. Letting people down. Those concerns are understandable. They’re part of carrying responsibility for a family.

The challenge is that when we never stop to examine those fears, they start making decisions for us. We assume the worst-case scenario is inevitable. We convince ourselves that a difficult conversation will end badly, that a new opportunity is too risky, or that one mistake will undo years of progress. As Chris pointed out, most of us never actually stop and ask whether those outcomes are likely or whether we’re simply filling in the blanks with our imagination.

Fear isn’t always the enemy. Sometimes it’s useful information. But when fear becomes the loudest voice in the room, it can keep us from becoming the person we’re capable of being. Maybe the goal isn’t eliminating fear. Maybe it’s learning to question it before we hand it the keys.

​

The Fear Audit

Why it Matters

Many fears become more powerful simply because they’re vague. When we never stop to examine them, our minds fill in the blanks with worst-case scenarios. Clarity doesn’t eliminate fear, but it often reduces its influence.

Why it Works

Our brains are wired to treat uncertainty as a threat. When a fear stays undefined, it’s easy to imagine endless negative outcomes. Naming it and walking through it forces the brain to replace assumption with evidence.

How To Do It

When a fear keeps showing up, stop trying to push it away and bring it into the light instead. Write down exactly what you’re worried about. Then ask yourself what happens next if that fear becomes reality. And then what happens after that? Keep going until you’ve worked through the actual consequences rather than the imagined catastrophe.

Chris shared that most people eventually discover the outcome isn’t nearly as devastating as the story they’ve been carrying around in their head.

Pro Tip

Try doing a pre-mortem instead of a post-mortem. Ask yourself: “If this fear became reality, what would have caused it?” You may uncover actions you can take today that dramatically reduce the chances of it ever happening.

Who Would You Be Without Your Concerns?

Chris shared a question that he credits to mindset coach Peter Crone. It’s deceptively simple, but it gets at something many of us rarely stop to consider:

“Who would you be in the absence of your concerns?”

Why it Matters

Most reflection exercises focus on what’s wrong, what needs fixing, or what problem needs to be solved. This question works differently. It temporarily removes the fears, doubts, and worries that often dominate our thinking and creates space to imagine what’s possible without them.

How to Do It

Set a timer for five minutes and write the question at the top of a blank page. Then start writing.

Don’t edit yourself. Don’t judge the answers. Don’t worry whether they’re practical, realistic, or achievable. Just keep writing until the timer runs out and see what appears on the page.

Pro Tip

Don’t focus on making the answer realistic. Focus on making it honest. The goal isn’t to create a five-year plan. The goal is to notice what shows up when fear isn’t making the decisions.

Time to Sprint: Does Your Calendar Agree?

Why it Matters

One of the ideas Chris returned to throughout our conversation was alignment. Not blowing up your life. Not reinventing yourself. Just making sure your time, energy, and attention are actually going toward the things you say matter most.

The challenge is that most of us don’t notice when we’ve drifted. Our priorities stay the same, but our calendars slowly start telling a different story.

How to Do It

Minutes 0–10: Write down the three most important things in your life right now.

Chris shared that many people answer with some version of family, work, and health. Your list may be different, but the exercise only works if you’re honest.

Minutes 10–15: Look at your calendar from the last two weeks.

Ask yourself:

  • Does my time reflect these priorities?
  • Where am I most aligned?
  • Where am I least aligned?

Minutes 15–20: Choose one area where your actions don’t match your priorities.

Identify one small adjustment you can make next week. Not next year, but next week.

Bonus 5 Minutes: Schedule that adjustment now.

Put it on the calendar before you move on to something else.

Why it Works

Most people don’t need a complete life overhaul. They need a small course correction. Alignment rarely comes from dramatic change. It comes from consistently making choices that reflect what matters most.

Pro Tip

Don’t try to fix everything at once. If you discover a gap between your priorities and your calendar, resist the urge to redesign your entire life this weekend. Pick one adjustment. One conversation. One boundary. One hour. Small changes are easier to sustain, and sustained changes are what create alignment over time.

Your Move

What’s one area of your life where the story you’re telling yourself might be holding you back more than reality is? Hit reply and let me know. I read every response.

Connect with Chris

Chris Woods helps people move from what he calls grinding to aligning.

After building a successful career that included leadership roles at Google, a near-death experience at age 40 pushed him to take a closer look at the fears and assumptions driving his decisions. That journey eventually led him into coaching, speaking, and writing.

Today, Chris works with people who want to stop operating from fear and start building lives that better align with their strengths, values, and priorities.

Follow Chris

On his website: https://chriswoodscoach.com/​

On Instagram: https://www.instagram.com/chriswoodscoach/​

On YouTube: https://www.youtube.com/@chriswoodscoach​

On TikTok: https://www.tiktok.com/@chriswoodscoach​

On LinkedIn: https://www.linkedin.com/in/chriswoods/​

​

Check out his book, Balls & Brains: https://amzn.to/4x7kzhD​

On the Show This Week

Continue the Conversation

This week on Gap to Gig, I sat down with Chris Woods for a conversation about fear, gratitude, strengths, and the stories we tell ourselves about what’s possible.

One thing I appreciated about Chris is that he doesn’t approach personal growth as a dramatic reinvention. He believes most people don’t need a revolution. They need a thoughtful evolution.

We get into:

  • Why successful people are often driven by fear
  • The difference between failure anxiety and fear of loss
  • How catastrophic thinking quietly shapes decisions
  • The role gratitude plays in changing perspective
  • Why strengths matter more than weaknesses
  • The question that can reveal who you really want to become

If you’ve ever felt stuck between responsibility and possibility, this conversation will give you plenty to think about.

Check it Out

🎧 Chris Woods on Overcoming Fear as a Working Dad

​Watch on YouTube​

​Listen on your favorite podcast platform​

The Last Laugh

Chris isn’t the only who understands the magic of those old Listerine PocketPaks.

TikTok logoPlay button

tim collins

Ngl i still love a listerine pocket pack 🤣🤣🤣 #childhoodmemories #nostalgia #millennialsoftiktok #2000sthrowback #zillennial #comedy #listerinepocketpack #millennialcore #skit

♬ original sound - tim collins

​

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