The retirement announcement of ESPN’s mega NBA Insider, Adrian Wojnarowski, caught many off guard. It’s not often you see a headline about someone stepping away from a massive job, especially when it’s accompanied by the figure “$20 million.” But the reality behind this isn’t as shocking as it seems, and it hits close to home for me—because I get it. I understand the need to step off the hamster wheel and reclaim your life.
I hear from men in Woj’s position all the time. High performers on the cusp of something great, something big, something financially rewarding—and yet, inside, they feel depleted. Woj isn’t the anomaly here. He’s the exception only because he made the move so many others won’t or can’t. The truth is, most men don’t retire, don’t quit, and don’t step back—not because they don’t want to, but because they can’t see a way out. Walking away from $20 million? That’s not a decision society allows men to make lightly. For some, it’s a decision they can’t make at all.
Let’s break it down:
Men, especially in midlife, are expected to stay the course. There’s an unwritten rule that success—true success—means more money, more accolades, more work. It’s not enough to have achieved financial security or to have built a legacy. We’re programmed to keep grinding, pushing, and chasing more, as though our worth is tied directly to our salary and title. And for what? A headline that reads “walks away from $20 million”? Most men would rather die with a full bank account than risk that kind of public scrutiny.
Adam Schefter described Woj’s rationale perfectly: “He didn’t want to have to, as we had to do in the past, take a shower with your phone up against the shower door so you can see a text that’s coming in, or take your phone with you to the urinal and hold it in one hand while you take care of your business in the other. That’s the life we live. And that was the life he chose not to do any longer because it takes over your life. He wanted his life back. He didn’t want to have to work on holidays. He didn’t want to be away from more family gatherings.”
I’ve been there. I spent 14 years in the insurance business. I never saw myself in that industry, but I worked my way up to partner. I sold, and I kept selling. I built a book of business, and as it grew, I somehow felt smaller. When our firm was acquired, and I had a few million in cash and stock, I still didn’t have the courage to tell my partners, “I’m done.” I signed on and was supposed to stay for a year before being shown the door.
And what happened as soon as I was on my own? I felt this self-induced pressure to do something even bigger, to not be irrelevant, to not just be okay with being okay. That’s the strange thing about men and ambition. We feel this inherent need to appear constantly ambitious. Why isn’t it considered ambitious to not want to work? To put yourself in a financially stable position where you can do whatever you want, whenever you want, with whomever you want, for as long as you want?
I spent a few hundred grand after leaving our firm, trying to be “ambitious”—making investments just to get on cap tables with certain people, trying to look like a big shot, attempting to find my next big thing. When in reality, all I really wanted was time. I should’ve just stuck that money in the S&P 500 or a CD at a guaranteed 6% return and taken at least a year to do absolutely nothing but spend time with my wife and sons, work out, travel, read, and write.
That’s why Woj’s decision resonates with me. He’s walking away from all that. He’s choosing to live with purpose, happiness, and intention. He’s showing us that we don’t have to keep spinning plates, that we can step off the hamster wheel and live life on our own terms.
He’s choosing his life over money, and that takes real courage. It’s a move more men need to consider.
The societal expectations are clear: we’re supposed to work hard, earn more, and keep chasing success, even if it drains us. But what happens when we step away? Many men feel like they’re less than who they were without the job, the title, and the paycheck. But that’s the lie we’ve been sold. Woj is proving that we can reclaim our lives and choose happiness over societal pressure.
So, as we watch him take this bold step, let’s remember the real lesson here: you don’t have to keep chasing. You don’t have to keep proving. You can walk away, you can choose your life, and that’s worth more than any paycheck or title. Woj’s retirement isn’t just about leaving ESPN—it’s about stepping into a life he truly wants. And that’s a move we all can learn from.
In Health,
Greg
