5 Things Holding You Back from Entrepreneurial Success (and How to Let Them Go)

Last October Graham and I had the pleasure of visiting Toronto, and everything you’ve heard about Fall in the Northeast is true. The changing trees are a sight to behold - brilliant shades of red, gold, and orange everywhere you look. One of the highlights of the trip was escaping the city for the day to explore the stunning fall foliage. Our friend took us to the Rattlesnake Point Conservation Area, about an hour outside the city. As someone who has always appreciate the beauty of nature, I thought I knew what to expect, but the experience exceeded every expectation.

The day was perfect for a hike - crisp, cool air, and skies clear for miles of visibility. When we made it to the Buffalo Crag lookout the view took my breath away. Below us the entire landscape seemed to unfold in a majestic sweep - rolling hills, forests painted in the vibrant colors of Fall. The trees seemed to be in full celebration of change, shedding their vibrant leaves to make way for rest before the next season of growth.

There’s something about being in a place like that, where the beauty of creation surrounds you and the vastness of the world feels so immediate, that brings a sense of peace and clarity. As I stood there, taking in the view, I couldn’t help but reflect on the power of letting go. The trees around us were in the midst of shedding their leaves, releasing what they no longer needed in preparation for winter. I realized how much this process mirrors our own lives.

Just as the trees know when it’s time to let go and make room for new growth, there are undoubtedly things in your life that you’ve been holding on to - things that no longer serve you. It could be that you’re gripping old projects, past mistakes, and commitments that have long since lost their meaning. My friend, I have been there too. Trust in the process of release. Only by letting go can you create the space for new opportunities, new growth, and new beginnings.

What is holding you back in your own life? Here are some areas to consider:

Let Go of the Past

The past can be a comforting place, but when it holds you captive, it prevents you from living fully in the present. It’s easy to get stuck in cycles of regret or to focus on mistakes that you wish you could change. Yet, constantly revisiting these moments robs you of the joy and opportunity that exists today. Instead of ruminating over past missteps, take a moment to reflect on the lessons they have taught you. Be grateful for the growth they’ve spurred in you. Each challenge has shaped you into who you are now and is a building block for the success story you are still writing.

However, at some point, you have to let go. The past is unchangeable, and no amount of wishing can alter it. What you can control is the story you choose to write today. Acknowledge the lessons, then release the pain, regret, or disappointment that may be lingering. By doing so, you create space for new experiences and opportunities, and more importantly, you allow yourself to be fully present in the life you’re living right now. Remember, you are the author of your own story, and every new day is a blank page waiting for you to fill it.

Let Go of What Is Finished

Sometimes, you know deep down that something has come to its natural end, yet you continue to hold on. Whether it’s a project that no longer excites you, a job that has run its course, or a commitment on your calendar that feels more like an obligation than a joy, it’s essential to recognize when it’s time to move on. I’ve found in my own life that I often resist letting go because my identity becomes intertwined with the things I’m doing. It feels safer to stay in the routine, even when the spark is gone.

But just like the trees that shed their leaves to conserve energy for new growth, we too must make room for the next chapter. Holding on to what’s finished only drains your energy, leaving little room for the new opportunities that are waiting to emerge. Growth is a continuous process, and part of that growth is knowing when to gracefully step away from what no longer serves you.

Trust that by letting go of what is finished, you are making space for something better to take its place. You’re meant to evolve, to try new things, and to embrace new challenges. Trust yourself to know when it's time to release something and move forward with confidence.

Let Go of Perfectionism

For many driven entrepreneurs, perfectionism can be both a motivator and a hindrance. The desire to do things well is admirable, but when the pursuit of perfection becomes overwhelming, it can stifle progress. Perfectionism often leads to unnecessary delays, anxiety, and a fear of failure. We may hesitate to launch a project or make a decision because it isn’t quite “perfect” yet. However, in business, waiting for perfection can be detrimental. The true is, nothing will ever be flawless, and striving for perfection can prevent you from moving forward.

Instead, focus on progress over perfection. Aim for excellence, but release the need for everything to be perfect before you take action. Growth happens through iteration and learning from experiences, even when they don’t go as planned. By letting go of perfectionism, you free yourself to experiment, innovate, and take bold steps that propel your business forward. Remember, done is often better than perfect, and the courage to act will yield far more than endlessly polishing an idea that never sees the light of day.

Let Go of Unhealthy Relationships

The people you surround yourself with have a profound impact on your life. As Jim Rohn famously said, “You are the average of the five people you spend the most time with.” Whether you realize it or not, those closest to you influence your mindset, your habits, and even your sense of what’s possible. When you are surrounded by people who uplift, encourage, and support you, you are more likely to reach your goals and step into your fullest potential.

However, there are times when we hold on to relationships that no longer serve us. Whether out of comfort, habit, or even a sense of obligation, we keep certain people in our lives long after the relationship has turned toxic or stagnant. It’s important to evaluate your inner circle regularly and to recognize when it’s time to let go of unhealthy relationships. This doesn’t mean cutting people out of your life without reason, but rather being mindful of the energy they bring into your life. Are they supportive? Do they challenge you to be your best self? Or do they drain your energy and hold you back?

When you make the courageous decision to release unhealthy relationships, you create space for the right people to enter your life—those who will inspire you, challenge you to grow, and support you on your journey. It’s not always easy, but it is necessary for your personal and professional growth.

Let Go of Bad Behaviors

Sometimes, the greatest obstacle to our success is not the people around us, but our own behaviors. We all have blind spots—those unhelpful habits or patterns that hold us back from reaching our true potential. Whether it’s procrastination, self-doubt, or even the tendency to overcommit, these behaviors can sabotage your success if left unchecked.

The first step to overcoming these patterns is to become aware of them. Take an honest look at your daily habits and routines. Are there behaviors that consistently lead to negative outcomes? Do certain habits cause you to fall short of your goals? If so, it’s time to address them head-on. Recognize that these behaviors don’t define you; they are simply habits that can be changed with intentional effort.

Once you’ve identified the behaviors that are holding you back, make a plan to change them. Start small and be patient with yourself. Remember, growth is a process, and change takes time. But as you begin to let go of these unhelpful behaviors, you’ll notice that new opportunities start to emerge. You’ll become more productive, more confident, and more aligned with the person you are truly meant to be.

The Power of Letting Go

As you reflect on these areas, ask yourself: What am I holding on to that no longer serves me? By letting go, you create space in your life for something better. You free yourself to embrace new opportunities and to step into the next season of your life with clarity and purpose. Just like the trees that release their leaves in the Fall, you too can let go, trusting in God’s plan for you and the new growth just around the corner.