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Drop the Woulda-Coulda-Shoulda Mentality and Live the Life of Your Dreams


It was a day that was supposed to be full of promises. A day of new beginnings. My beautiful white dress was ready. The flowers were ordered, the cake was being embellished, and the caterers were hard at work. Everything was ready for a meticulously planned celebration.

Sounds like my fairytale was about to come true, right?

It wasn’t. It was the day I made one of the biggest “mistakes” of my life. It wasn’t a “mistake” that I discovered in hindsight. Nope, I knew that day that I was making a “mistake.” I quote the word mistake because I truly don’t believe in mistakes, since they are situations that provide the foundation from which we grow and evolve. This “mistake” was a gift, since it was the impetus for profound learning and provided me with the three things I love most, my daughters. But on the morning of my wedding, I knew I didn’t truly love the man I was marrying in the way I should, that he didn’t treat me the way I wanted to be treated, and that there were many huge red flags. But, I was too scared to admit the truth and too committed to my “to-do list of life” to deviate from my plan. So, I kept myself distracted by focusing on the details of the wedding, instead of being honest with myself about what I was feeling and the true viability of this union.

Like many women I meet, I had always been a bit of a perfectionist. My life followed a long list of milestones I thought I should accomplish. Before my engagement, I had graduated from an Ivy League university (check!), attended law school (check!), and established a successful career as an attorney (check!). The next steps on my checklist were marriage, children, and that white-picket fence fantasy.

Even though I achieved every goal and milestone on my “to-do list of life” on time and on task, the truth is that I was never truly happy. Although I had moments of joy and fulfillment, they always felt fleeting. There was always that constant ache of wanting and knowing that “there had to be something more.” So, after each accomplishment, I would be back in the race, searching for “What’s next?”

Empty and exhausted, that is when I realized that my happiness would not come from checking off boxes on my to-do list and creating some picture of what I thought my life should look like on the outside. Instead, it would come from tuning into what was inside and living in alignment with my integrity; my deepest truths, grandest desires and fullest expression of my authentic self. It was time I stopped “shoulding” on myself!

Stop Shoulding Yourself

Our to-do lists are made up of a long list of “shoulds.” Some “shoulds” like, “I should exercise regularly, or spend quality time with my children or partner” can be positive and healthy. But, there is also a dark side to our “should” mentality. Masters at manipulation, our “shoulds” push us to live in accordance with societal norms, our need to fit in or “get it right,” or outdated, unrealistic, or non-serving expectations of ourselves or others. They can have us compromise our truth, disconnect from our vision, and overcommit to things that are not in alignment with our integrity.

Although successfully crossing items off our to-do list brings moments of happiness, they will generally be short-lived, since living from our “shoulds” seals in our fate of living less than satisfying lives. Before we know it, we will be back on that gerbil wheel, running as fast as we can, looking for the next thing we should be doing to prove to the world and ourselves that we are enough.

Turn your to-do list into your bucket list.

To move from your to-do list to your bucket list, instead of looking to the external world or other people for your truth or how you should be living your life, you must take a U-turn back to yourself. What are your dreams and visions? What is on your bucket list?

Creating a bucket list inspires you to think outside the confines of your day-to-day reality, connect with your passion, tap into your dreams and step into a world of possibilities. And here is the key in crafting your list of bucket list items… they do not have to make sense, and you don’t even need to know how you are going to make them happen or when. Bucket lists are often open-ended. Unlike the items on your to-do list, which can feel tedious and heavy, your bucket list inspires you. It lights you up from the inside out and act as a motivational force that will move you powerfully forward toward the future of your dreams.

Ultimately, living from your bucket list becomes a dynamic process. If you allow yourself to live in the magic of realizing what was once only a dream, you will feel turned on and excited about continuing to live on a trajectory of possibilities and passion.

This post was written by Kelley Kosow, author of The Integrity Advantage.

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