I’ve had moments recently (more recently now that I’ve turned 40) where it hits me. 

This is it. This is life. It’s happening right now, and there’s no slowing it down. 

I’m getting older. My friends are getting older. My parents are getting older.

One day, they’re taking care of you… driving you to practice, packing your lunch, making sure you don’t burn down the house. Then, suddenly, you are driving to practice, packing lunches, and trying to learn the meaning of Skibidi and Rizz (I’m still slightly confused).

At some point, you stop thinking of them as just your parents and start seeing them as people. People with the same thoughts, worries, and fears you have now. People who once looked at their parents and thought the same thing.

It’s wild. The perspective shift that happens when you go from being someone’s kid to being someone’s parent. The realization that they were never all-knowing. 

The realization that we are all getting older. Whew… sorry to hit you with this on a Sunday night.

It happens slowly. A little less energy. A few more complaints about aches and pains. They stop wanting to drive at night. They move a little slower.

Then, one day, it hits you: they won’t be here forever.

I’ve been thinking about this a lot lately, and it came up in my conversation with Shali Reed on the most recent episode of the Revenue Diaries. She lives with her parents and sees it happening in real-time. She calls it anticipatory grief—knowing what’s coming but not knowing when.

It’s strange to think about. The people who once seemed invincible were just figuring it out, just like we are. And now, here we are… doing exactly the same. 

I wish I had a fix… a tool… some guidance… the secret to understanding how to make the most of the time, to slow it down, but I don’t. This is only a reminder that time moves forward, whether we’re ready for it or not.

❤️ kyle

On the 80/20 Rule of Loving Your Work (And Knowing When It’s Time to Go)

Y’all know the Pareto Principle. 20% of customers drive 80% of revenue, 20% of efforts create 80% of results. But what if the same applies to your career satisfaction?

This might sound crazy but what if you need to love your job 80% of the time to power through the hardest 20%?

That 20% is where the real growth happens. It’s where you struggle, fail, and succeed. It’s the board meeting that makes you sweat. The cross-functional project that keeps you up at night. The challenge that makes you rethink how you lead your team. 

It’s hard, but it’s where you get better.

But here’s the kicker: if you don’t enjoy or find meaning in the other 80%, that sh*tty 20% can drain you. Instead of pushing you forward, it burns you out. Believe me, I’ve experienced it.

God, I love a good 80/20 rule to start the week off right. So here’s the question: how do you know if you’re in the right place or if it’s time for a change?

You need to distinguish between growth and drain.

Not all challenges are created equal. Some build your career. Some make you a better practitioner. Others drain the life out of you. Here’s how to tell the difference:

✅ You learn something valuable. Even when it’s tough, you build skills, confidence, or experience to serve you long-term.
✅ It aligns with your goals. The challenge is part of a bigger picture—whether it’s career growth, leadership, or a skill you want to master.
✅ There’s a clear path forward. You can see how pushing through leads to improvement or opportunity.
✅ It’s hard, but you feel accomplished. Even if it sucks at the moment, you come out on the other side feeling stronger.

❌ No real learning. The challenge feels repetitive, pointless, or like busywork.
❌ It’s outside your control. The problem stems from poor leadership, bad culture, or broken systems that won’t change.
❌ It doesn’t align with your goals. You’re struggling for something you don’t care about or see value in.
❌ You feel stuck, not stretched. Instead of a sense of progress, you feel like you’re spinning your wheels with no real wins.

And here’s the most important thing… are you ready? You are going to deal with drain. You are going to feel like things are outside of your control. You are going to experience instances where the work doesn’t align with your goals.

There will be times when you just do not care. That’s when the 80% matters.

If your job energizes you 80% of the time, the tough 20% is worth it. But if you’re miserable 80% of the time, no amount of growth in the last 20% will make up for it.

That’s when burnout kicks in. That’s when you wake up every day dreading your calendar. That’s when the hardest 20% feels pointless, and that’s not the way this should work.

I try to follow this rule in my career and I’ve had multiple occasions where I’ve wanted to quit, but before I make any rash decision I ask myself these questions:

• Do I feel challenged in a good way or just overwhelmed?

• Is the hard part helping me grow, or just making me miserable?

• Do I see a clear future here where I feel engaged and valued?

• If nothing changed, would I be happy here in six months? A year?

If the answer to those last two is no, it might be time for something new.

Life’s too short to spend 80% of your time resenting the work you do. Find something where the hardest 20% is worth it… where the challenges help you grow instead of just breaking you down.

And if you’ve been ignoring that gut feeling? Maybe it’s time to listen.

On Leadership Habits to Earn Respect

I love simple and easy-to-understand leadership advice, especially from people who have done the job. And Sterling Snow is one of those people. 

He recently decided to share his thoughts about the simple things leaders can do to earn respect. I agreed with every. single. word of this post. 

It’s a great gut check for anyone leading a team. 

1. Do what you say you’ll do. Always.

2. Keep your action-to-talk ratio at least 2x.

3. Communicate problems early—but always with a proposed solution.

4. Be quick and dependable in your responses.

5. Have a consistent routine others can digest and work with.

6. Personally produce meaningful and regular momentum-generating results.

7. Always have action items and owners for every decision.

8. Accept responsibility and clearly articulate changes made when things go wrong.

These are gold. Words to live by. Copy it. Print it out. Save it on your phone. But before you do, there are a few I would add to the list: 

9. Give direct, honest feedback early and often.

10. Recognize and celebrate wins, both big and small.

11. Share all work before ready. Do not deliver a finished project without stakeholder involvement.

Most importantly, it’s easy to fall short. Sterling admits it. And I’m similar, and I fail to meet my expectations almost weekly. Many leaders have a hard time living up to the habits above for many reasons, so instead of focusing on the habits, let’s spend some precious minutes on a Sunday night looking at some of the fixes.

BONUS: I will also use tenets from Do Better Work by Max Yoder. Max was my boss at Lessonly, and is still a friend. His advice has helped me become a better leader and person. 

Why Leaders Fail the Habits

1. You are a slave to your schedule. Busyness can’t be an excuse.

You know how it is. Many of you get so caught up in the deluge of meetings, emails, and context switching between pain and glory that you let the fundamentals slide. The intent is to be reliable, responsive, and proactive but the chaos takes over. 

Prioritize clarity over certainty. As Max puts it in Do Better Work, “People need to understand your logic, not just your decisions.” Instead of letting busyness become a crutch, communicate often, delegate better, and don’t overcomplicate things.

2. You lack self-awareness. 

Some leaders don’t even realize they’re failing in these areas. They think they’re great communicators, but their teams feel in the dark and even worst, downtrodden. They believe they give strong feedback, but their employees are guessing at expectations.

Make space for others to challenge you. Ask for feedback and actually listen. Self-aware leaders create an environment where people feel safe to be honest.

3. You have a strong fear of discomfort

Okay. Welcome to being human. Giving feedback, admitting mistakes, and addressing underperformance isn’t fun. So, some leaders dodge hard conversations and let problems fester.

Normalize feedback and have difficult conversations. Back to Do Better Work! Max argues that feedback should be like brushing your teeth—frequent, expected, and a natural part of how a team operates.

And one of the biggest pieces of feedback avoidance? Not having difficult conversations. Leaders often avoid difficult discussions because they fear damaging relationships, making someone uncomfortable, or dealing with emotions. But avoiding these conversations compounds the problems. 

Don’t let that sh*t fester! Embrace the discomfort. Strong leaders prepare for tough conversations with empathy, clarity, and focus on solving the problem. Max puts it best: "We cannot change what we do not discuss." Great leaders create environments where honesty isn’t feared… it’s expected. 

4. Your work is inconsistent. 

People follow what leaders do, not just what they say. If a leader is unpredictable—one day communicative, the next totally unavailable—trust erodes.

Show, don’t tell. Create rhythms and habits that make you a steady, reliable presence.

5. You let your ego and insecurity shadow your work.

This is the silent killer of great leadership. Because, let’s be honest, you have to have a little big of ego and insecurity to be successful. But many of us refuse to admit when we are wrong, hesitate to credit others, or resist feedback because it threatens their self-image.

Lead with vulnerability. Max emphasizes that great leaders aren’t the ones who “always have the answer.” They’re the ones who say, “I don’t know, but let’s find out together.” Owning your mistakes and asking for help doesn’t weaken your leadership… it strengthens it. 

Here’s the straight story… it’s not about perfection, it’s about consistency. The best leaders just keep showing up, making improvements, and being intentional.

So here’s a challenge: Look at Sterling’s list (and the additions above), pick one thing, and commit to doing it better. 

I know I sound like Grandpa Bill Robertson when I type this but, “Because respect isn’t given… it’s earned.” And the best way to earn it? Do the work.

On Blending Cultures, Parenting, and Watching Your Parents Get Older

Listen on Spotify and YouTube

Okay. I wrote about this in the intro, but it was too important not to mention again. One of the biggest surprises of adulthood isn’t the career shifts, the house payments, or even the am I doing this right? moments. It’s realizing your parents were just figuring it out, too.

That hit me hard in my conversation with Shali Reed, who grew up in a traditional Indian household but now raises two daughters in a home that blends cultures, traditions, and perspectives.

Her four-year-old is creative and thoughtful, and her two-year-old is a wrecking ball. Every day is a mix of “Mom, I made you a cake!” and destruction.

Watching kids grow up forces you to rethink what matters.

Faith, Family, and the Weight of Tradition

Shali grew up in a Hindu household, surrounded by religious ceremonies and expectations. Her husband, Devon Reed (yes, the LinkedIn guy), grew up in a Christian home where Sundays meant church and community.

Their approach to parenting? It’s not about religion. It’s about values.

Instead of forcing a belief system, they expose their kids to everything—Diwali, Christmas, Holi, Easter—so they can decide what resonates. The focus is on education, not doctrine.

It got me thinking about the traditions we inherit. Some we embrace. Some we reject. And some—like Pop-Tarts mysteriously appearing in the pantry—never go away.

The Reality of Watching Your Parents Get Older

The part of our conversation that stuck with me was anticipatory grief—realizing your parents won’t be around forever.

Shali’s parents, now in their 60s, live with her family. On one hand, it’s great. Her kids get to be raised by their grandparents, and she gets more time with them. But it also means facing their aging head-on. They’re moving slower. They’re not as active. And now, she’s the one taking care of them.

At some point, the roles flip. The people who once seemed invincible need your help.

It made me think about my own parents—the habits they hold onto, the ways they’ve changed over time, and the subtle ways they try to make up for things they didn’t know how to express when I was younger.

And it reminded me that, at the end of the day, they were just figuring it out too.

Check out Episode 5 for a real conversation about family, identity, and how we see the people closest to us.