Are You Getting Too Comfortable?

I was often annoyed when my cross-country coach would tell me to just believe in myself and envision crossing the finish line. “You’ve just got to believe in yourself.” Really?!? That’s it?!? If it were that simple, everyone would be doing it. And yet… it is that simple. Simple doesn’t mean easy. True belief in oneself takes effort and energy. It demands commitment and discipline. It’s not a quick fix or a motivational phrase you tape to the mirror and forget about the next day. It’s a muscle, a spiritual one and an emotional one that has to be exercised over and over again. There’s a reason most people give up before they ever reach the vision they once felt called to pursue. Somewhere along the way, their belief in themselves got buried beneath fear, fatigue, or comparison. When I look back at everything I've accomplished in my life, it was never complicated to get to the finish line. What it did require was consistent, often uncomfortable action, especially when I felt like I had very little left in my tank. I had to get quiet and reconnect with the vision. I had to remind myself why it mattered and I had to move forward even when the circumstances didn’t look favorable. ~ Some days I doubted my book would ever get published. (I’ve written 7.) ~ Some days I doubted if anyone would ever buy a ticket to one of my events. (I’ve hosted the Upside Summit for 18 years—and people kept coming back.) ~ Some days I doubted whether I'd ever get another client. (And yet, I’ve worked with over 100,000 leaders in the past 20 years.) It’s easy to look at the outcome and assume the path was certain. In each milestone, it was preceded by a moment of doubt—a moment that required me to choose belief over fear. The doubts were real. So was the belief that somehow, some way, the pieces would come together. Some days, it was my faith in God that pulled me through. Other days, it was a conversation with a friend, a coach, or a mentor. Truthfully, sometimes I needed all three. Because every great leader knows that no one goes it alone. And you do have to believe in yourself—and believe that where you're going is worthwhile to keep going. ACTION: The Upside Challenge for the week is to identify where you need more belief in yourself right now. Is there a decision you’ve been avoiding because doubt is louder than faith? Is there a dream you’ve shelved because the finish line feels far away? Whether it’s making a call, saying yes to help, or simply declaring out loud what you truly want… Do it. Remember, simple isn’t easy. Yet it is possible. And it’s worth it.

Have you ever been stuck in a long line, wishing you could just march right up to the front? When I was in my 30s, that’s exactly what my friends did at a local nightclub. At the time, I was mortified. Yet, deep down inside I thought it was the coolest thing. They carried themselves like they belonged, like they didn’t need anyone’s permission to take up space. I remember thinking… maybe that’s what leadership looks like. Take the risk. Be bold. Do what it takes to get ahead. It felt like confidence. It looked like power. And I'll admit ... there are times in my life when I made decisions based on how cool I thought something would make me vs. whether I thought it was the right thing to do. Over time, I’ve learned that what’s cool rarely aligns with what’s truly lasting. Cool fades. Purpose endures. It’s easy to be drawn to what turns heads or makes a strong impression and harder to stay anchored in what’s true, especially when it means standing alone. Leadership asks something deeper from you. It requires a willingness to listen for what’s real. To live with alignment. To walk forward even when no one’s clapping. And that's one of the hardest lines to walk in leadership. Every day you'll be confronted with decisions that will challenge you in ways that you never imagined. They will put your moral and ethical code on trial or out for bid to the highest buyer. If you make your decisions based on what you see others around you doing, or what the media says is "normal", you'll always fall short from what God has in store for you. When I first started my career in Federal law enforcement, I saw the world through a lens of good and evil. There was no middle or grey area. And then, over time, I watched colleagues make decisions that didn't sit well with me. Behaviors that left me questioning what the "right" thing to do, has challenged my moral fiber. We all carried the same badge. We all have the same set of credentials that read, " This officer possesses integrity. " Yet one of my closest partners made choices that eventually landed him in jail and serving time for his choices. Leadership will reveal what’s underneath. This is why the people around you deeply matter. When things get uncomfortable (and they will), you need to be surrounded by people who call you higher. People who see you for who you are and who you're becoming. That’s the sacred space we’re creating at the Upside Retreats. So here’s the invitation: Is it time to pause and look at the decisions you’ve been making? Is it time to notice who’s around you and whether those voices are helping you stay grounded in truth? Is it time to re-commit to who you are, what you want, and why that matters? Because life has never needed more cool leaders. It needs more aligned ones. ACTION: The Upside Challenge for the week is to step back from chasing what looks shiny and start leaning into what’s actually meaningful. Begin by making a list of three things you’ve recently said “yes” to because they sounded impressive or exciting. Then, identify the one that feels least aligned with your values or your calling and take one clear step back from it. That might mean turning down the next opportunity, rescheduling a commitment, or resetting expectations. Use the time and energy you free up to invest in something that may not be flashy yet fuels your deeper purpose.

I consulted with a potential client who had started a business and was making gobs of money. He shared with me that the downside was he has to deal with folks who don't do the right thing morally and ethically in running their business. Because he knew it and it didn't align with who he was, he was struggling and it was keeping him up at night. He was conflicted and wanted to talk it out with me. While I understood the struggle he was having between his mind and his Soul, I'm not an answer machine. I don't tell folks what to do. What I did tell him was that there are 6 Leadership Stepping Stones that lead to mastery. Make a misstep, and it may cost you your livelihood. That's the best way I can explain the importance of listening to your Soul's deepest wisdom. Years ago, I got myself in a jam not heeding this piece of advice. Someone I knew through a friend of a friend wanted to sponsor my annual leadership conference. Every time we got on the phone, I had a sinking feeling in the pit of my stomach that what they were saying just didn't add up. Some folks would say this is intuition. I've known it to be the voice of the Holy Spirit trying to give me direction. Even though I knew something was off, I said yes to the money. And it ended up costing me. How many times have you made mistakes like that... just because the money seemed too good to pass up? Listening isn't something that is always easy to do. You've got to be clear about who you are, what you want, and why it matters. After making one too many costly mistakes on my leadership journey, I decided that I was done trying to do it all on my own. The level of clarity I now have is perplexing to most folks. Yet this internal compass guides me throughout each day. When you're connected to this type of wisdom, you don't waste your time making decisions that take you off course, even for a split second. You move forward steadily with an ease that is hard to put into words. And the money always follows. There’s a cost to ignoring what you know deep down to be true. Whether it’s a gut instinct, your inner voice, or the prompting of the Holy Spirit, when you override it, you pay. I’ve paid. So has the leader I consulted with. Success without alignment will always leave you restless. And real clarity doesn’t come from grinding harder or checking more boxes. It comes when you stop long enough to listen to what your Soul is trying to say. It’s why I no longer walk alone. Because every leader needs space to sort through what matters most. ACTION: The Upside Challenge for the week is to notice where you're choosing based on money and take one step toward alignment instead. Maybe it’s a client you’ve outgrown, yet you keep them because they pay on time. Maybe it’s an offer that feels off, even if it looks impressive. Maybe it’s a deal you’re rushing into just to hit a number. Pause. Check in. Then choose the path that brings clarity and is aligned, not just cash. Notice what opens up when you trust alignment over urgency.