I'm not a therapist. I'm not an expert on depression. I'm just someone who, about two years ago, was so consumed by it that I made a plan to end my life.
I'm writing this for Chasing Red Flags because this is a community built on honest conversations, and because November opens with gratitude. I've learned that gratitude isn't just a feeling you have when things go right. Sometimes it's the thing you find on the other side of the worst season of your life, once you're finally willing to look at what got you there.
THE LIFE THAT LOOKED LIKE “ENOUGH”
Shortly before that period of depression, I had sold TOMS. From the outside, it looked like the finish line. I'd built a company around a simple idea, given away over a hundred million pairs of shoes, written a bestselling book, and sold the business for more money than I ever imagined having.
I did what a lot of people do when they "make it. "I built the house, took up bigger hobbies, kept traveling, chasing one adventure after another.
And none of it touched the thing I actually needed.
I kept thinking a change in circumstance would finally make the discomfort go away. I moved, changed relationships, stayed busy, gave away tens of millions of dollars. I tried nearly everything except the one thing I was avoiding, which was sitting still long enough to ask why none of it was working.
Eventually my body and mind forced the question on me anyway, in the most dramatic way they could. I became so depressed that I wanted to die.
WHERE GRATITUDE ACTUALLY STARTED
Thankfully, I reached out instead of acting on that plan. My friends, my family, and a therapist helped me get into treatment. While I was there, I read a book that became something of a map for me, one that reframed depression not as something broken in me, but as a signal. A call to change how I was living.
That work led me to a single belief sitting underneath almost every decision I'd made since I was a kid: I am not enough.
I'd built my entire identity on top of that wound without ever naming it. From junior tennis to my first business to TOMS, I kept chasing the next thing that might finally prove I'd made it.
Every achievement was, in some quiet way, an attempt to finally earn the right to feel okay. I'm starting to think you can't outrun a belief like that. I don't think I'm done healing it, honestly.
I committed to a forty-day meditation practice built around that belief. It was the hardest thing I've done, and also the most transformational. In the stillness of that practice, I heard something clear and unmistakable: use your story and your resources to help others not feel this way. It didn't arrive like an idea I could take or leave. It felt like a responsibility.
That's where ENOUGH came from. A hand-beaded bracelet, green for mental health awareness, sold in pairs so one can be kept and one can be given away, with a hundred percent of profits going to mental health organizations. It's a small object built to carry a simple reminder: you are enough, and you always have been.
WHAT “ENOUGH” MEANS TO ME NOW
My definition of success used to be almost entirely external: what I'd built, what I'd achieved, what other people saw. Today it's much quieter than that. It's whether I'm living in a way that actually matches who I am, rather than performing a version of myself I think other people expect.
That shift didn't come from a single breakthrough. It came from being willing to keep asking uncomfortable questions long after the easy answers ran out, and from people around me who were willing to have honest conversations with me even when I wasn't in a place to hear them well.
That's why I think what Chasing Red Flags is doing matters so much. ENOUGH exists to remind people they're already enough, but reminding someone and helping them actually believe it are two different jobs. That second job happens in the slower work of self reflection and real conversation, whatever form that takes for you. You can't think your way to believing you're enough. You have to sit with it, write it down, say it out loud to someone, and practice it.
WHAT I’M GRATEFUL FOR TODAY
I'm grateful I didn't act on that plan eighteen months ago. I'm grateful for the people who showed up for me when I couldn't ask clearly for help. I'm grateful, strange as it sounds, for the depression itself, not for the pain of it, but for what it forced me to finally see.
And I'm grateful that "enough" turned out not to be a place I had to arrive at through one more achievement, but something I get to practice, imperfectly, one day at a time.
If you're in a season where nothing you've built or achieved seems to be closing the gap inside you, I'd gently ask you to consider that the gap might not be waiting on your next accomplishment. It might be waiting on you to stop and finally listen to what it's actually asking for.
Carpe Diem,
Blake Mycoskie
You can find ENOUGH and learn more about our mission at WeAreEnough.co, and hear
more of these conversations on https://www.youtube.com/@NoMagicPillwithBlakeMycoskie.