Each November and December, I relive a difficult period in my life. This year was especially difficult. For two months: I unplugged to meditate, pray, fast, reflect, purge, assess my life, and write my way through what I learned about myself. Over that time, I placed everything on the back burner: my work, my fitness, my recreation, text messages, e-mail, social media, and some of my most meaningful friendships.
What I revealed in myself were countless failures and an inadequacy. I learned how little I appreciated those who deserved it most, how often I failed to show others the respect they deserved, and how little I showed people what they really meant while I had the opportunity. The rest of my time is devoted to trying to make up for those shortcomings.
Over the last 16 years, I have teetered on the brink of self-destruction. I have battled through multiple evictions, joblessness, addictions, and a post traumatic stress that I wouldn’t wish on my worst enemy. After 16 years of running up hill at full speed, I am not really sure how I am still here.
I have battled severe depression and bouts of self-sabotage. I have often lived at the mercy of friends, partners, society, luck, and the grace of each. I have appreciated my friends and peers too little. I have listened to some who meant most the most to me tell me that I was horrible to them. Typically, the closer you are to me, the more that you have to deal with this sort of thing. I’d been given a second lease on life but it’s like I held it against myself. And by doing so, I began to fracture the opportunity I had.
This is a stream of work that I am deeply devoted to publishing, not just the writing but the reflections that follow. Over two months, I wrote a collection of over 150 letters to people who changed my life over the last 16 years. In most cases, I plan to send these letters privately. In some cases, I will post letters of gratitude, regret, and acknowledgment to this Substack. By the end of this project, some of those 150+ letters and attached addendums will be published here. My hope is to revisit some of these letters with updates, resolution, or closure of any sort. They will tell a story that I gritted my teeth through for nearly two decades.
In reality, 150 entries isn’t nearly enough to account for the gratitude, apologies, lessons, or recognitions to cover every interaction of note in my years between 22 and 38. Those who don’t know me as well will also better understand why this reset began at 22. At times, it can feel as though I am stuck in that 22nd year, incapable of graduating from that crucible.
This isn’t a vanity project, I expect that some may leave this with a worse impression of me than they had before but at least it will be honest. Some of the lessons that I have reflected on over the last few months were hard to hear and even harder to process. In some of the published letters of gratitude, recognition, or apology: names are changed to maintain decorum. In some cases, we may no longer be friends, partners, peers, or family but in each case - the impact that they have had on my life is written about in a positive manner.
While I have survived in many ways and succeeded in others, I have failed in almost every way imaginable. In the process of running a business to build a life for two exceptional children, I have been quietly working to avoid breaking. In doing so, I often lost sight of what was most important: the people around me. My hope is that there can be a bright side to this. If I do get through this period, you will see something different in me than what existed before. And if I don’t, I hope that by the end of 150 public or private sends, each person will finally know what their impact meant to me.
I am a veteran of the newsletter business but this is my first Substack. The letters will flow every few days until completion. Thank you for reading and I hope that you appreciate the candor, self-criticism, honesty, and sense of optimism.
By Web Smith