Recently, I read something that felt less like a quote and more like a wake-up call.
“Don’t let your past failures bankrupt your future victories.”
If you’re anything like me, you’ve had nights where you replayed old mistakes like a highlight reel — the missteps, the regrets, the “should haves.” And instead of protecting you, those replays drain you. They rob you of energy and confidence. They chain your future to your past.
Yalom’s Bigger Truth
Psychiatrist and existential psychotherapist Irvin D. Yalom believed that too much of traditional therapy was just symptom management — soothing the anxiety without addressing its roots.
Instead, he argued that our real suffering comes from avoiding what he called the four ultimate concerns of being human (Existential Psychotherapy, 1980):
Death
We don’t like to think about it — yet the idea of death can be life-saving. Remembering that our time is finite forces us to live with urgency and gratitude. Every moment matters.
Freedom
Freedom isn’t about having no constraints; it’s about choosing. Yalom reminds us to replace “I have to” with “I choose to.” This moves us in our brains from our amygdala to our prefrontal cortex. Entrepreneurs who embrace this unlock ownership and agency, even in tough situations.
Isolation
Being human means we are ultimately separate. And yet, connection is what keeps us alive. For entrepreneurs, this is especially true: an entrepreneur alone is an entrepreneur at risk. Leadership without community is a dangerous road.
Meaninglessness
Success for success’s sake leaves us empty. Yalom warns that without meaning, achievement is hollow. The real shift is going from success to significance — from money and metrics to impact and legacy.
My Own Story of Facing the Concerns
When my staffing firm was $600,000 in debt, I carried every failure on my shoulders. I feared the “death” of my company. I avoided asking for help — isolating myself. I told myself, “I have to fix this.” I tried to fix it alone, out of shame, guilt and embarrassment. And as I fought to survive, the meaning of why I started the business in the first place got blurry.
What saved me wasn’t ignoring those fears, but facing them:
- Accepting that the company might die forced me to live and lead differently.
- Choosing to hire a coach reframed “I have to” into “I choose to.”
- Breaking isolation, and sharing deeply with my EO Forum, gave me the courage to keep going.
- And reconnecting to meaning of figuring out the “WHY” and purpose of Diversified Industrial Staffing, turned debt into a mission — one that ultimately landed us on the Inc. 5000 list six times.
Three Shifts to Free Yourself
If you feel weighed down by yesterday, try this today:
- Name the fear you’re avoiding — Which of the four ultimate concerns is knocking at your door? Death, freedom, isolation, or meaninglessness? Call it out.
- Reclaim your freedom — Replace one “I have to” with an “I choose to.” Watch how it changes your posture.
- Reconnect to significance — Ask: Am I chasing success or creating meaning?
Why It Matters
Every time you avoid these ultimate concerns, you play defense. But when you face them head-on, you unlock freedom. You lead not from fear of the past but from responsibility for the future.
As Yalom wrote: “Though the physicality of death destroys us, the idea of death saves us.”
Your Invitation
Grab a piece of paper today. Write down one regret or fear that still lingers. Then ask yourself: Which of Yalom’s four concerns is it tied to? And how can I use that awareness to choose differently moving forward?
That’s how you stop your past from bankrupting your future victories. That’s how you step into freedom.
Here’s to leading with courage,
