why are you still working?

i often meet professionals—high-level executives, hedge fund managers, senior engineers at top firms—who have spent over a decade in their roles but feel uninspired, exhausted, or simply stuck. when i ask why they’re aren’t pursuing something more fulfilling, i often hear:

  • "what do you mean? you have to work."

  • "i can’t afford to retire—i’m just keeping up with my lifestyle."

  • "kids are expensive. i have no choice."

  • "if i stop working, what will i even do?"

what i’ve found is that these fears are often not financial—but psychological. they’re about being trapped in a cycle of obligation rather than choosing your path. when some of these professionals actually pause to do the math, they realize something shocking: they could have stepped away years ago. in a few cases, after a single conversation, they retired within weeks—sometimes to travel, sometimes to launch passion projects, sometimes just to breathe.

but what’s really holding you back?

many people assume they can’t leave their careers because of financial obligations, but when we dig deeper, we often find something else: a deep-seated belief that work is an obligation rather than a choice. they feel they should be working, even if they’re miserable, even if the money isn’t truly necessary, even if they no longer know why.

if i push on this, they say they need the money for big purchase or some variant of "my $5m+ house" or "no one with kids can retire". sometimes i get answers like “i enjoy collecting art and spend $500k a year on it,” or ‘i love expensive food.’ this hypothetically makes sense, but i rarely get these answers.

the house thing confuses me. is living in a $4m house instead of a $3m house worth 40+ hours of unhappiness each week? it seems odd. when people say making $500k a year is barely middle class due to house prices, it doesn’t seem like a personal preference—it seems like a lack of imagination.

and the last one, “my life would have no meaning if i wasn’t working for a tech company or a financial firm,” is a bit depressing. isn’t the idea that your life’s meaning is tied to working at one of these places worse than just saying life has no meaning?

i am not against people working because they enjoy it or because they’re buying something they want, but i meet a lot of people who seem unhappy with their jobs and keep working not because they need the money, but because they can’t imagine not working.

i’m not here to tell you to quit your job, but i am here to challenge you to think differently. if you’re successful but unfulfilled, if you’re working without a clear purpose, or if you haven’t deep dived into asking, what do i actually want?—then we should talk.

for those who interested approaching the next chapter of their lives with the same rigor and strategic focus as their work, i offer the highest signal-to-noise process you will find. click below to schedule a conversation.

what people are saying

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what people are saying *

‘i feel (conceptually) outgunned.’ - co-founder of $75b marketcap company

"this isn’t traditional coaching—it’s a methodical, high-impact program that is unlike anything i’ve seen.” - non profit executive

"he made me see the bigger picture in ways i hadn’t before."
– managing director, global bank

frequently (and infrequently asked questions)

1. who are you?

i’m danilo. i’ve built and scaled companies at the intersection of ai and venture capital—raising funds from khosla ventures and greylock, founding a y combinator-backed startup, and hiring c-level executives. beyond that, i’ve completed a the equivalent of a phd on human coordination and have worked with the same coaches as fortune 500 executives and high growth startup founders..

see highlights of my work: coordination theory of everything, the goal of your platform, minimum viable definitions of life, creativity, risk, complexity and god.

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2. who do you work with?

the typical client is a senior executives, typically with a decade of experience within an organization. i work with no more than eight clients at a time. i typically work with only about 20% of the individuals i engage with. a rule of thumb i have is that i only want to work with someone i’d be excited to invite to sound-swim.com.

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3. what is this service about?

it’s a guided program designed to help you develop clear thinking towards the next chapter in life. the approach is paradoxical — equally parts engineering and art, precise and open-ended, rigor-intuitive. i offer three engagement levels based on the client challenge:

  • 1-month package – an intensive sprint for rapid insights.

  • 6-month package – 12–15 hours of coaching with bi-weekly sessions.

  • 12-month package – 30–40 hours of coaching, with monthly sessions and a focus on long-term strategy.

i operate as a combination of a mirror and structured sparring partner—someone who challenges and refines your thinking as you navigate. i operate like a conceptual co-founder, applying the same rigor as karl weick’s what theory is not, theorizing is.

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4. what happens after i start this process?
we begin with a comprehensive 360 assessment and a proprietary method called a meta profile to understand where you are in your career, what motivates you, and what you’re seeking in life. i draw from concepts from across disciplines to guide you through reflection and practical exercises to identify key areas for change. the work is ongoing email/texts threads, supplemented by 1:1 calls lasting one-three hours every week(s) based on the tempo of the challenges. by the end, most individuals have a clear, actionable plan for your next step.

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5. how do i know if i’m in the right place for this?
if you believe that your life is your most valuable asset and you’re committed to investing time in understanding it—whether that means embracing serendipity or exploring deeper layers of meaning—this may be the right fit. you don’t need to make drastic changes immediately; the goal is to help you think differently about both your work and your life. through guided self-reflection, we’ll help you clarify your true aspirations—whether that’s advancing your career, making a shift, or achieving a more fulfilling balance between work and personal life.

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6. what makes this different from traditional career coaching?
traditional career coaching typically focuses on advancing within your current role or securing a new position. in contrast, this service takes a more holistic approach, while operating within a rigorous, engineering-driven framework. we go beyond just career advancement, helping you strategically align both your professional and personal goals for long-term fulfillment and success.

"a game-changer in how i view life and work"

before working with danilo, i was a partner at a technology infrastructure company, stuck in a cycle of long hours and diminishing returns. i had everything society tells you to want—financial success, a beautiful home —but i felt unfulfilled and exhausted. i didn’t know how to get off the treadmill, and i convinced myself i had to keep going.

danilo’s approach was unlike anything i’d ever encountered. instead of pushing me towards a quick fix or a career change, he helped me shift my perspective on what truly mattered. the process was incredibly structured yet deeply reflective. we worked together to assess my values, my motivations, and where i truly wanted to go next—not just professionally, but in every aspect of my life.

after just a few sessions, i started making decisions with clarity and purpose. the tools he provided helped me see that i didn’t need to keep sacrificing my happiness for an arbitrary standard of success. in fact, i realized i could retire within a few months if i wanted to—and i was finally free to pursue passions i’d long put on hold.

danilo’s program gave me more than insights; it gave me confidence in taking control of my life. i can now approach my next chapter with the same focus and intentionality i applied to my career, but this time, for me.

if you’re feeling stuck or unfulfilled, i can’t recommend danilo enough. this isn’t just career coaching—it’s a transformative journey into how you can live life on your terms.

— former manager director, douglas elliman