Why Most Leaders Get Stuck (And How to Break Free)

Leadership requires consciousness and courage. Lots of folks have talent. Yet, it's rare to see a leader with 360-degree awareness who has the courage to stand in the dark places where leadership is often required to go. This is why for years I've shouted from the rooftops that comfort doesn't change the world. (I even have a shirt in the Upside store that has it printed on the back.) Because no matter how many gifts you've been given, or how much raw talent you possess, you can't erase the struggles of the human experience. You can numb. You can follow. Or, you can choose to step up and lead. And doing the latter is the hardest. All day long I'd much rather have all of the autonomy with little to no responsibility. Yet I understand to do that is copping out on the full usage of my divine gifts, abilities, talents, and experiences. I was built to lead. And that means being responsible ... when things go right, and when they don't. Over the years, I've numbed out on mindless TV shows, and unhealthy fast food only to get me further off-course from my divine mission and purpose. Gaining weight and feeling tired were just symptoms of an unhealthy system, and a socially acceptable way to numb. Leadership takes strength and discipline that are rooted in consciousness and courage. Because most folks don't want to be accountable at that level, they'll opt out and choose to follow someone else's lead. That's never been my style. I've learned more from going through hard times than I ever did sitting on Easy Street. The best piece is that you get to choose for yourself. ACTION: The Upside Challenge for the week is to choose one thing the future you, the one fully walking in your divine assignment, would do. You already know what it is, that nudge you’ve been feeling. That quiet pull from God asking you to move. Maybe it’s making the call, saying no, saying yes, clearing space to think, or finally following through on what you said mattered. Whatever it is, stop numbing around it. Take the step.

Every so often, I read something that inspires me to be better. After a month of giving to clients at two retreats and working privately with a client through a one-on-one VIP leadership retreat at Summit Hills Farm, this story touches me in a very deep way. Sometimes folks ask me if it's possible to overgive. This story answers that question beautifully. "I asked the leaf whether it was frightened because it was autumn and the other leaves were falling. The leaf told me, "No. During the whole spring and summer, I was completely alive. I worked hard to help nourish the tree, and now much of me is in the tree. I am not limited by this form. I am also the whole tree, and when I go back to the soil, I will continue to nourish the tree. So I don’t worry at all. As I leave this branch and float to the ground, I will wave to the tree and tell her, 'I will see you again very soon'." That day, there was a wind blowing and, after a while, I saw the leaf leave the branch and float down to the soil, dancing joyfully, because as it floated it saw itself already there in the tree. It was so happy. I bowed my head, knowing that I have a lot to learn from the leaf." ~ Thich Nhat Hanh Reading that story reminded me of the leaders I encounter. The ones who give deeply, love fiercely, and show up fully, even when no one’s watching. You may not always see the impact you’re having. You may wonder if it’s too much, or if it even matters. What I know to be true is... Nothing is ever wasted. ~ Every act of service… ~ Every moment of generosity… ~ Every time you choose love over fear… ... It all lives on. Just like the leaf, your presence remains long after the moment passes. What you’ve built and what you’ve become—it stays on. So if you’ve been wondering whether it’s okay to rest, to pause, to let go… It is. Because your leadership is already rooted in what you've poured yourself into. This is the holy space between what was and what’s next. And you, leader, are right on time. ACTION: The Upside Challenge for the week is to write one truth you know about leadership or legacy on a sticky note or card. Make it simple and true for you. Maybe it’s… “My presence changes the room.” “I was created to lead with love.” “What I build matters.” And then place it somewhere you’ll see it—your mirror, your journal, the dashboard of your car. Let it meet you in the in-between moments. And let it serve as a reminder of who you are.

For years, Valentine’s Day has been my 2nd favorite holiday after Thanksgiving. Every year, I notice people talking about love and being loving, equating it to what they got from their partner. One year, I wrote a post where I joked around about asking Jim for toilets — which was true. And some folks were horrified. Valentine's Day hasn't been one of my favorite holidays for 4 decades because of the gifts I've received, although I have gotten some spectacular ones. Rather, Valentine's Day offers folks a reminder to see through the lens of love, no matter where they're at or what they're experiencing. LOVE is the vibration I want to operate on 365 days throughout the year. It’s how I want to be REMEMBERED. In a few days, Jim and I will celebrate 21 years of marriage. Yes, 21 years. That kind of time gives you a deeper understanding of what love really is. And it’s not always grand or visible. Being loving and kind isn’t hard to do. And it's not easy, either. It does require intentional choice in every circumstance and situation. Once you set your mind that’s who you want to be, you’ll see opportunities to be loving and kind all day long. Researchers have discovered that you also get what’s called the ‘helper’s high’ when you operate this way… …because acts of altruism trigger the same endorphins as a ‘runner’s high.' What does this look like? Smile. At people you’ve never met. Hold the door open for a stranger. Give BIG hugs to the people you care about most. Say “please” – and say “thank you”. You’d be surprised at how few people actually do. Surprise a friend with a phone call or a gift of appreciation … for no reason other than they were on your mind. Give back and volunteer your time at a colleague’s event, local animal shelter, or soup kitchen. (Yes, they still have those.) Pay for someone’s cup of coffee at the drive-thru or the person standing behind you in line at Starbucks. When I lived in New Jersey, I used to pay for people’s tolls before EZPass came along and took away the fun of it. Go through your closet and donate the clothing you still love, yet haven’t worn in a long time. Look for opportunities to pay someone a compliment – and then do it. You just may make their day. Text or call a loved one just to say, “I’m thinking about you…” Bring your neighbors flowers. Loving-kindness is just a way of being. You don’t need a special day or any holiday for LOVE to show up. And the best leaders get this. So if you want to be the kind of leader who leaves a legacy... Start there. Lead with love. Even when no one’s watching. ACTION: The Upside Challenge for the week is to practice one unseen act of loving-kindness. Choose one person in your world — a colleague, neighbor, team member, or friend — and do something kind without telling them it was you. It can be a handwritten note, a small gift, a thoughtful gesture, or an act of service. Then notice how it shifts you — because powerful leadership begins in the places no one else sees.