Was It Worth It?

Welcome to the Recovery of an Insecure Overachiever newsletter! I will try my best to share a new article every week. As you pave your own path and overcome challenges, you are not alone. Together, we can support each other on our empowerment journeys.?Thank you for joining me in this conversation.

In an earlier post, I disclosed my deep identity as a recovering insecure overachiever, perfectionist, and workaholic. I also have the great honor of coaching many leaders who share these identities and work at elite organizations. In the safety of confidential coaching conversations or established learning programs, I regularly have conversations with extremely driven and accomplished leaders, who are so stressed out and unhappy. We need to talk about our challenges more often and more publicly. This is my attempt to do so.

In two days, on 2/13/24, I will be commemorating the five year anniversary of my father's death. Six weeks after he received a terminal cancer diagnosis, he died. I was incredibly fortunate to have had incredibly powerful conversations with him in those last days of his life. We discussed so many topics, but perhaps what has stuck with me most is his regret over prioritizing his work over his personal life and time with his family.

My father was the greatest source of unconditional love I have ever had in my life. He was my biggest fan. I absolutely would not have been able to accomplish what I have without his support. He instilled in me a deep sense of hard work and moreover the capacity to dream big. I am forever grateful to him.

Yet at the same time, he only role modeled being an extreme workaholic. During much of my childhood, he was absent working late hours and on the weekends. He had no healthy boundaries or any sense of work-life balance. As his child, I took on these patterns, with significant negative consequences for my personal and professional life, as well as my physical and mental health. It has taken me over a decade to begin to unlearn these behaviors and create a new healthy relationship to ambition, my identity, and my career. I am still a work in progress.

On his death bed, as he was reflecting on his work life with me, he explicitly told me that it was not worth it. He said he should have stopped working on the weekends and spent more time with us. Even in the hospital after he was given a terminal diagnosis, he still worried about checking his work email. I had to gently encourage him that officially no longer mattered anymore.

In exactly five months from now, I will be turning forty. I have lots of mixed feelings about this, but I am trying to reframe them and embrace this new chapter of my life. As I look back on my past decades, and in this moment, contemplate my next steps in my career, I ponder, has it been worth it? Will it be worth it? What does that even mean to me? I want to be successful and happy. My career is such a huge part of my identity, but it is no longer my entire sense of self-worth.

Our words become our thoughts which become our actions which become our habits. The big choices are actually just thousands of small choices we make. Every step of my career journey, there are risks I have chosen to take, or not to take. So far, they mainly have been worth it.

At the end of my life, whenever that may be, I pray the choices I made for my life and career, for my pursuit of success and happiness, may they be worth it. I invite you to explore what it means for you to be worth it. Whenever your time to depart this earth comes, I truly hope you will say yes, it was absolutely worth it.