I've spent a decade coaching high-performers who seem to "have it all." They're the ones who hit every milestone ahead of schedule, from their Ivy League degrees to their seven-figure exits. From the outside, they're crushing it - promotions, investments, picture-perfect families on Instagram. But when we dig deeper in our sessions, there's almost always this gnawing emptiness that shows up. And the scariest part is that more achievement, more wealth, and more status seem to make that emptiness grow larger, not smaller.

Here's what I noticed after leaving my Managing Director role at BlackRock. The higher you climb, the more you outsource every friction point in your life - from grocery shopping to managing your calendar. You start spending money to buy back tiny moments of rest, convincing yourself it's the only way to stay sane. Your spending ratchets up as you justify $14 cold-pressed juices and $90 "recovery" sessions because you "deserve it" after working so hard. The ultimate irony is that this increased spending locks you into needing to make even more money, creating a hamster wheel of your own design.

The Real Price We Pay

I see this pattern play out in three distinct stages with my clients:

  1. First, you lose your ability to experience joy in simple things
  2. Then your relationships start to decay as you bring home a shell of yourself
  3. Your creative problem-solving atrophies because you throw money at everything
  4. Finally, you forget how to relax without feeling guilty

The pattern becomes especially clear when working with tech founders and Wall Street executives. They've mastered what I call "offensive optimization" - the relentless pursuit of efficiency, productivity, and leverage. But they're completely blind to "defensive optimization" - protecting space for rest, play, and genuine human connection. Each time they hit a new milestone, instead of feeling fulfilled, they just move the goalposts.

Breaking Free From The Cycle

My own journey taught me some uncomfortable truths about ambition and happiness. I used to measure everything through the lens of my personal "scoreboard" - comparing myself to peers on salary, title, and status. Even after walking away from Wall Street, I caught myself recreating the same patterns as an entrepreneur. It wasn't until I started doing the deeper inner work that I realized how much of my striving was rooted in avoiding feelings rather than pursuing genuine fulfillment.

The path forward usually involves some combination of these elements:

  • Learning to separate your identity from your achievements
  • Developing a relationship with "enough"
  • Creating space for non-optimized time
  • Building genuine connections that aren't transactional
  • Practicing the art of receiving without earning

When my coaching clients ask what success looks like on the other side, I tell them it's less about arriving at some destination and more about changing their relationship with time. You start noticing the small moments again - like when my daughter grabs my hand walking to school or when I catch a perfect wave during a dawn patrol surf session. You rediscover the ability to waste time without feeling guilty. The constant mental chatter about optimizing and achieving starts to quiet down.

The ultimate paradox is that letting go of the relentless pursuit of more often leads to getting what you actually wanted in the first place. But it requires confronting something that terrifies most high-achievers: the possibility that you've been optimizing for the wrong things all along. When you finally slow down enough to ask yourself what "enough" looks like, you might be surprised to find you passed it a long time ago. The real question then becomes not "what else can I achieve?" but rather "what am I willing to give up to reclaim what matters most?"