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Aug. 7, 2026

Would You Want Your Kids to Live Your Life?

Issue 49

​

When Fear Starts Making the Decisions

Inside this issue

  • Pressure or Purpose?
  • Rocks, Pebbles, and Sand
  • Time To Sprint: Give Yourself Permission
  • What’s one “should” you’ve been carrying that no longer feels aligned with the life you want to build?
  • Connect with Andrew
  • Check out this week’s episode
  • The Last Laugh: Baby Review
  • But before we get to all that, here’s what’s…

On My Mind

video preview​

A lot of dads are carrying around fear and calling it responsibility. I don’t mean irrational fear or the kind of fear that shows up during a genuine crisis. I’m talking about the quieter version. The fear of not providing enough. The fear of falling behind. The fear of making a mistake that impacts the people you care about most.

The tricky part is that these fears often sound reasonable. In fact, they can look a lot like responsibility. They push us to work harder, stay later, and sacrifice more. Sometimes they even help us survive difficult seasons. The problem is that what helps us survive a season isn’t always what helps us build a meaningful life.

This week on Gap to Gig, I sat down with Andrew Poles to talk about dad identity, ambition, and the pressure to succeed. Andrew started his first business as a young single dad because he wanted the flexibility to be part of his daughter’s life. He worked long days in a retail store, spent nights building furniture, and did whatever he could to keep the business alive. Looking back, he realized something that many dads eventually discover: the thing driving him wasn’t always inspiration. Much of the time, it was fear.

At one point, Andrew said, “I was more afraid to fail as a father and to provide for my family than I was inspired to build something meaningful for my family.” I think that distinction is worth paying attention to because fear and responsibility can produce many of the same behaviors. Both can make us work hard. They can make us put our family’s needs ahead of our own. They can convince us to make sacrifices in the short term for something we hope will pay off in the long term. If you looked only at the actions, it would be difficult to tell the difference.

The distinction is happening underneath the surface. Responsibility is usually connected to something we’re moving toward. Fear is connected to something we’re trying to avoid. Responsibility says, “This matters, so I’m willing to do the work.” Fear says, “If I stop pushing, everything might fall apart.” Responsibility allows us to make decisions. Fear makes decisions for us. From the outside, those can look remarkably similar. From the inside, they feel very different.

One of the ideas Andrew kept returning to throughout our conversation was how easy it is to become trapped by a collection of “shoulds.” I should be earning more. I should be further along by now. I should be able to handle everything myself. I should always be available. Over time, those shoulds become so familiar that we stop questioning them. We assume they’re our goals when sometimes they’re just our anxieties wearing a different outfit. The result is that we can spend years building a life without ever stopping to ask whether it’s actually the life we want.

Fear rarely has a finish line. There is always another milestone to reach, another number to hit, another reason to keep pushing. It keeps moving the goalposts. That’s why fear can be such an effective short-term motivator and such a dangerous long-term strategy. No matter how much progress you make, fear has a way of convincing you that you’re still one step away from finally feeling secure.

None of this means hard work is bad. It doesn’t mean ambition is bad. It doesn’t mean sacrifice is bad. Every dad goes through seasons where more is required of him, and sometimes the right answer is to put your head down and do the work. The question is whether the work is being driven by something you genuinely value or by something you’re constantly trying to outrun.

Fear can be incredibly useful in the short term. It can help you survive uncertainty, navigate difficult circumstances, and push through challenges you didn’t think you were capable of handling. The problem is that fear was never designed to be a long-term strategy. Left unchecked, it has a way of turning every achievement into another obligation and every milestone into another moving target.

​

Pressure or Purpose?

Why it Matters

One of the most interesting ideas from my conversation with Andrew was how many of us spend years pursuing goals we never consciously chose. We inherit expectations from parents, coworkers, culture, social media, and previous versions of ourselves.

Over time, these expectations start to feel like facts. We stop asking whether they still make sense because we’ve repeated them so many times. That’s how “I want to” slowly becomes “I should.”

The problem is that “should” is often rooted in fear. Fear of falling behind. Fear of disappointing someone. Fear of not measuring up. When that happens, it becomes difficult to tell whether we’re pursuing something because we genuinely value it or because we’re afraid of the consequences of not pursuing it.

How to Do It

Think about the three biggest sources of pressure in your life right now. For each one, ask yourself:

  • Why does this matter to me?
  • Who taught me that it mattered?
  • If nobody else were judging me, would I still choose it?

Don’t rush the exercise. The goal isn’t to abandon responsibility. The goal is to separate your values from everyone else’s expectations.

Why it Works

Most people never stop long enough to examine the assumptions driving their decisions. Once you identify which pressures are rooted in values and which are rooted in fear, it becomes much easier to decide where your time, energy, and attention actually belong.

Pro Tip

If you find yourself using the word “should,” pause and replace it with “want to” or “choose to.” The difference can be surprisingly revealing. If neither replacement feels true, you may have found an expectation worth reexamining.

Rocks, Pebbles, and Sand

Andrew shared a framework during our conversation that has been around for years, but it’s one of those ideas that becomes more useful every time you revisit it. Imagine your life as a glass jar. The rocks are the things that matter most. The pebbles are important but flexible. The sand is everything else competing for your attention.

Most people fill the jar with sand first. Emails. Meetings. Notifications. Errands. Requests. Small tasks. Minor obligations. Then they try to squeeze the rocks in afterward and wonder why they never seem to fit.

Why it Matters

Most dads don’t have a prioritization problem. They already know what matters most. The challenge is protecting those priorities when life gets busy.

It’s easy to assume that family time, exercise, sleep, friendships, and personal growth will naturally find space in our schedules. In reality, they often get crowded out by whatever feels most urgent in the moment.

How to Use It

Identify your rocks. For many dads, those might include:

  • Family time
  • Sleep
  • Exercise
  • Meaningful work
  • Time to think
  • Relationships
  • Activities that genuinely recharge you

Put those on the calendar first. Everything else gets scheduled around them.

Why it Works

Every calendar is a reflection of what receives protection and what receives leftovers. When you put the rocks in first, you’re making a conscious decision about what deserves your best energy instead of hoping it survives whatever remains.

Pro Tip

One of your rocks should be something that refills your cup. As Andrew said during our conversation, you can’t give away what you don’t have.

Time to Sprint: Give Yourself Permission

One of the themes that kept surfacing during my conversation with Andrew was permission. Not permission from a boss, a spouse, or a parent. Permission from ourselves.

Many dads become so focused on responsibilities that they stop paying attention to curiosity. They get very good at solving problems, meeting expectations, and doing what’s required. Over time, that can create a life that works on paper but feels increasingly disconnected from the person living it.

Why it Matters

The goal of this sprint isn’t to make a major life change. It’s simply to reconnect with something that interests you before your inner critic has a chance to explain why it’s impractical.

How to Do It

Minutes 0–10: Answer

Grab a sheet of paper and answer this question:

“What have I been curious about lately?”

Don’t worry about whether it’s productive, profitable, realistic, or useful. Just make a list. Maybe it’s learning a skill. Starting a project. Exploring a career path. Taking a class. Reconnecting with an old hobby. Having a conversation you’ve been putting off.

The only rule is that it has to be something that genuinely interests you.

Minutes 10–15: Identify

Look at your list and circle the item that has shown up more than once in your thinking over the past few months. Then ask yourself a second question: “What makes this interesting to me?”

Keep writing until you get past the obvious answer. Very often, the thing we’re curious about isn’t actually the thing we’re curious about. Sometimes a desire to start a business is really a desire for autonomy. Sometimes a desire to change careers is really a desire for growth. Sometimes a new hobby is really a desire to create, connect, or challenge ourselves again.

Minutes 15–20: Take the first step

Take one concrete step toward exploration. Not commitment. Exploration.

Read the article. Buy the book. Send the email. Sign up for the class. Schedule the coffee. Listen to the podcast.

You’re not deciding your future today. You’re simply gathering information.

Why it Works

Many of the biggest changes in our lives don’t begin with certainty. They begin with curiosity. We rarely think our way into clarity. More often, we act our way into it.

Giving yourself permission to explore something doesn’t obligate you to pursue it. It simply creates the opportunity to learn something you didn’t know before.

Pro Tip

If you’re struggling to identify what you’re curious about, think back to the last time you lost track of time while doing something. Curiosity often leaves clues long before we’re willing to acknowledge them.

Your Move

What’s one “should” you’ve been carrying that no longer feels aligned with the life you want to build? Hit reply and let me know. I read every response.

Connect with Andrew

Andrew Poles is an entrepreneur, executive coach, and leadership advisor who helps founders and leaders build organizations that can grow without consuming every ounce of their time and energy.

What I appreciated most about this conversation was Andrew’s willingness to talk openly about topics many dads feel but rarely discuss. Fear. Self-worth. Identity. The pressure to provide. The challenge of figuring out whether you’re building a life you actually want or simply responding to a life you feel obligated to pursue.

Follow Andrew

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

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

On Facebook: https://www.facebook.com/andrewpolescoach/​

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

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

On the Show This Week

Continue the Conversation

This week’s conversation explores what happens when ambition, fatherhood, and identity become intertwined.

Andrew shares lessons from building businesses while raising his daughter as a single dad, how fear influenced many of his decisions, and why so many men struggle to separate their self-worth from their achievements. We also discuss curiosity, meaning, emotional honesty, and the role those things play in building a life that feels successful from the inside, not just the outside.

In this episode, we discuss:

  • Why fear often disguises itself as responsibility
  • How “should” becomes a prison
  • The hidden relationship between identity and overwork
  • Why curiosity is often a better guide than certainty
  • The difference between building from fear and building from joy

Check it Out

🎧 Andrew Poles on Dad Identity, Ambition, and the Pressure to Succeed

​Watch on YouTube​

​Listen on your favorite podcast platform​

The Last Laugh

If kids were reviewed like tech products…

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Corp

Product review of my 4 month old son.

♬ original sound - Corp

​

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Gap to Gig

Gap to Gig is for working dads navigating the life in between who we are, what we do, and the life we want to build. Through honest conversations, practical ideas, and grounded perspective, we help dads build meaningful work, stay present for the people who matter most, and make more intentional choices about the life they’re building.

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