How Much Is a Year of Your Life Worth?
Uncovering the Emotional and Mental Costs of Holding On
Earlier this week, I spent time with a prospective client, an executive who had dedicated the past decade to building a wildly successful company. In 2022, the business was acquired, but now he’s locked into a lucrative earn-out that stretches until 2027.
"Just three more years," he said, the weight of those years clear in his voice.
His gaze drifted to the window, as if trying to picture the next few years, but I could sense all he saw was more of the same. Then he said something that stopped me:
“I’m incredibly bored at work, just going through the motions. I’m using only 20% of my brain and 10% of my heart. I don't know if I can do this much longer.”
It was such a raw statement of disconnection and exhaustion. This man, who had helped build something extraordinary, wasn’t physically or contractually trapped—he could walk away at any time. But he felt the weight of responsibility: the need to ensure the business continued to thrive and the pull of financial security. These inner dynamics kept him in a role that no longer inspired him.
I let the silence hang for a moment, then asked, “How much is a year of your life worth?”
It’s a question we rarely stop to ask ourselves. We often think about the payoffs—what we’ll earn or achieve if we just keep going. But how often do we weigh those against the costs?
The real cost of perpetuating a career that drains us isn’t just a void of inspiration—it’s the slow erosion of our soul. We lose energy, creativity, and the sense of purpose that once fueled us. Over time, we begin to operate on autopilot, and the work we once cared about and believed in becomes something we merely endure. And that doesn’t just affect our careers—it seeps into our relationships, our health, and our overall sense of fulfillment. The longer we stay, the harder it becomes to remember who we were before the disconnection set in and the aliveness we once felt.
We tell ourselves we’re being responsible by sticking it out, but at what cost? How much joy, flow, meaning, and connection are we sacrificing to stay in a situation that no longer serves or energizes us?
It’s a tough question, one that cuts to the heart of our conditioning and the choices we make when we defer alignment for some future payoff. And it’s not always about money. It could be the promise of a promotion, a step change in influence, or the allure of accolades—all the things the ego craves to feel safe and secure.
But the longer we wait, the more we bleed vitality, joy, and creativity. We lose our sense of purpose, connection, and authenticity. Slowly, we become disconnected from our passion, our energy fades, and the richness of living fully slips away—until we’re left navigating life on autopilot, far from the alignment we crave.
And yet, we often stay. Sometimes it’s the fear of missing out—the anxiety that if we leave, we might miss an opportunity or success just around the corner, something we’ve worked so hard to be a part of. Other times, it’s the weight of all the years we’ve already sacrificed, trapped by the feeling that we can’t turn back now. Those sunk costs keep us anchored, even when we know deep down it’s time to move on.
Then there’s the fear of the unknown. Even when we know we’re misaligned, the uncertainty of what’s next can be paralyzing. The thought of leaving behind what’s familiar—even if it’s draining—feels safer than stepping into the unknown. We might ask ourselves, "What if things get worse? What if I make a mistake?" The fear of taking a leap without a clear landing spot often keeps us stuck. In the absence of guarantees, the discomfort of staying can feel more manageable than the risk of pursuing something uncertain, even if it might lead to a life of greater fulfillment.
We might stay because of the expectations of others—feeling the weight of social or familial pressure to keep going. Sometimes, it just feels easier to stick with the routine, even when it no longer fulfills us. There’s also the pull of loyalty—the fear of letting someone down if we leave—or the lingering hope that things might still improve, despite the evidence suggesting otherwise. Together, these forces can keep us anchored in place, even when just about every part of us knows it’s time to move on.
But how often do we find ourselves caught in this trap? Scores of professionals endure these periods of misalignment, telling ourselves we’ll hold on just a little longer. We believe that something will eventually click into place. Yet, as months turn into years, that waiting becomes a pattern. The erosion of our energy, enthusiasm, and sense of self doesn’t stop until we make the choice to step away.
I went through this for nearly three years when I was in venture capital—holding on, waiting for my carry to vest, convincing myself that making partner would solve all my issues. I kept going, even as I felt increasingly misaligned and burnt out. Toward the end, I stayed in the game because it was all I knew, and I couldn’t see a bright future beyond it.
The truth is, the cost of continuing down a path out of alignment is much higher than we realize. It’s easy to stay comfortable, to let time pass, and to convince ourselves that holding on is the responsible thing to do. But what’s the real price of that comfort? What’s the value of a year spent living at 20% of your capacity—using just a fraction of your brain and barely touching your heart?
I could see the weight of this question beginning to settle in the conversation. It wasn’t just an abstract idea anymore—it was personal, something he had to face. So I asked him again, “How much is a year of your life worth, continuing in this way?”
He paused, looked down, and mumbled under his breath, "A lot."
“What did you say? I didn’t quite hear you,” I asked with a gentle smile.
“A lot,” he repeated, this time a little louder. We locked eyes, both smiled and knew, in that moment, that a year of life is priceless.
As we wrapped up the call, I could see in his eyes that the question was working its way through him. Maybe for the first time, he was allowing himself to consider it.
We often think the unknown is the most terrifying thing, but in truth, staying the same might be even more painful. Slowly, we erode who we are by holding on, by waiting. So, is it worth it? Is the price of comfort worth the slow burn of losing yourself? Only you can decide when the cost becomes too high.
If you’re finding yourself in a similar place—unsure whether to stay or go—it can help to pause and ask yourself some honest questions:
What is the real cost of staying where I am?
What am I losing by holding on?
Am I choosing comfort over growth?
What might I gain by stepping into the unknown, even if it feels uncertain?
What am I really longing for?
Sometimes, the answers aren’t immediate, but sitting with these questions can help you start to untangle what you truly want from what you’re afraid to leave behind.
In the end, it’s not always about the future payoff—it’s about the richness of today. Every year, every moment spent out of alignment is a moment we can never get back. The cost of waiting is higher than any reward the future might promise. The real reward is living a life where we are fully engaged, present, alive, and in tune with what truly matters.
I know this feeling all too well. Toward the end of my venture capital career, I held on—hoping that the next deal, raise, or promotion would reignite my spark, telling myself it was only a matter of time. But the truth is, no payout, no future role, was worth the price I was paying in real time. The longer I waited, the more it cost me, and the clearer it became that I had to make a change. I'm so grateful I did.
And so I ask again: How much is a year of your life worth? Because the longer we wait, the more it costs us—not just in money, but in the vitality, joy, and passion that make life worth living.
Dude this post is FIRE. I was right there, suffering profoundly, when I made the decision to put a CEO in charge of my last startup. Given the stage, I had to give up massive equality. It was super frightening to share the decision with investors, my team, and my community. And it was the best decision I ever made. Priceless. Thanks for writing this! I sense it’s going to help a lot of people.
Oh man, this one cuts deep...
I was right there too, waiting for options to vest over YEARS! Every day was a slog and I kept doing the math on whether it was worth it to step away now or wait.
You can picture the benefits of more money with pure clarity. The benefits of stepping away, however, are fuzzy and unknown.
In retrospect, I'm grateful that I powered through to get to a certain threshold. And I'm also grateful I stopped and took a leap of faith to get out.
Ironically, WHILE making the decision, I was fraught with doubt. AFTER making the decision, I've never once regretted my choice.