How Not To F*ck Up Your Startup

REALITY CHECK 

If you’re a founder reading this, ask yourself honestly: 

• What changed in me when the money hit the account?Did I feel safer? More pressure? 

• What pace am I moving at and who’s setting it? Is it driven by my vision or by investor expectations, comparison, or fear?

• Have I confused urgency with importance?What big-picture priorities have I sidelined in favor of short-term wins?

• If the money disappeared tomorrow, what part of this company would I still fight for? What do I still believe in underneath the pressure?

• What parts of this vision still feel unfinished but I’m pretending they’re done? What are we calling “launch ready” just to meet expectations or deadlines? 

• Do I expect the team to execute at full capacity without giving them a clear, stable foundation? What systems or clarity am I withholding (intentionally or unintentionally)?

• Is the urgency I’m creating rooted in real deadlines or in my own anxiety about proving this idea works?Who set the timeline and why? Would the work improve if we slowed down 10 percent? What am I afraid will happen if this takes longer?

• Have I made room for ambiguity, or am I punishing people for not having answers I don’t have either? Am I modeling curiosity or control?

• Do I regularly invite perspective from the people closest to the actual work? Who are we overlooking because they don’t have power, but they have insight?

• How honest am I being with my team about where we really are? What am I not saying out loud because I’m trying to protect morale or my reputation?

REALITY CHECK

If you’re a founder reading this, ask yourself honestly: 

• Is your team building toward today’s problem or yesterday’s idea? What data, patterns, or feedback are you using to define today’s problem? 

• Are you making space for iteration, or are all roads still required to lead back to the original concept? What ideas or prototypes have you recently green-lit that veered from your original solution? 

• When was the last time you asked your team what they’re seeing, not just how they’re executing your vision? What’s one insight a team member shared that surprised you or challenged your assumptions?

• Is your original solution serving your mission, or has it become the mission? If your current product or program disappeared tomorrow, could your mission still live on? Are you spending more energy defending the original idea or advancing the actual problem-solving?

• Could your founding idea become a philosophy that guides instead of a structure that constrains? What core belief from your early days still feels resonant and flexible? 

• What part of your solution are you most emotionally attached to? Would letting go of that part feel like failure, even if it made your impact more effective?

• Are you still trying to prove that your original idea was “right”? What would it mean to shift from being “right” to being useful?

• What would we build if we started fresh today with everything we know now? What part of the old plan would we feel relieved not to carry forward?

• If the solution we’re using was invented by someone else, would we still choose it?Are we sticking with it because it works, or because it’s ours?

REALITY CHECK 

If you’re a founder reading this, ask yourself honestly: 

• When was the last time your charisma was enough? What happened in that moment? How did people respond to you? What part of you felt most alive or affirmed?

• When did you sense it no longer was? Was there a moment when your usual spark didn’t land the same way? How did you feel? Confused? Dismissed? Exposed? What did you do next?

• Are you using your charisma to serve the mission or to secure your place in it? What story are you telling yourself about your role in the organization? 

• Where are you being rewarded for charisma in ways that make character harder to prioritize? What external praise are you receiving that keeps you from slowing down and doing the inner work? 

• Where in your leadership do you feel most misaligned with your values? What pressure, expectation, or fear is driving that misalignment, and what would alignment actually look like in that space?

• Are you still trying to impress people who only know your curated self? What would it cost you to show them who you really are?

• What parts of you are built for the first half of the journey? And what parts are trying to grow for the second? Are there parts of your leadership that feel outdated or misaligned?

REALITY CHECK

If you’re a founder reading this, ask yourself honestly: 

• Are you trying to be the exception or build something sustainable? What common founder patterns (burnout, micromanagement, team churn, identity fusion) have I assumed won’t apply to me? 

• Where do I believe my passion, intellect, or intuition will “outsmart” reality? What’s something I’ve witnessed in other founder-led orgs that I’m secretly afraid is true in mine too?

• Have you fused your identity with your company’s survival? If the company stalled or failed tomorrow, who would I be? In what ways have I made decisions to protect my sense of self rather than serve the actual mission?

• Are you waiting for a savior or building real capacity? Who or what am I currently putting unrealistic hope in to “solve” our biggest problems? 

• How often do I redirect energy away from actual work to chase “the next big thing” that might rescue us? What’s one hard, unglamorous thing I’m avoiding while I wait for rescue?

• Are you the system or are you leading one? Where am I the sole decision-maker by default? How have I unintentionally made myself the bottleneck by being the rescuer? Who on my team has the skill or insight to lead something I’ve been holding on to?

REALITY CHECK

If you’re a founder reading this, ask yourself honestly: 

• What signals has my body been sending me that I’ve ignored or minimized? If someone on my team reported these symptoms, would I tell them to rest? Why do I think I’m the exception?

• What am I doing out of fear rather than clarity or conviction? Is my urgency grounded in reality or scarcity?

• Is the way I’m working today sustainable three months from now? If not, what’s one thing I can shift this week?

• What needs to change so the mission can survive me, not just survive because of me? Am I scaling systems that can live without me or just scaling effort? 

• Am I more focused on how things look than how things actually are? Have I ever used a marketing refresh, rebrand, or comms push as a way to soothe internal panic or distraction? Is my team clear on what the true priorities are, or are they chasing my preferences?

• If preservation of the mission meant I had to loosen my grip, rest more, or even step back for a season, could I do it?What version of myself does this season require? What version of myself is still trying to be?

Click here for a clear comparison chart showing the differences between self-preservation and mission preservation in organizational behavior → Chapter 5 Table.

REALITY CHECK

If you’re a founder reading this, ask yourself honestly: 

• Am I demanding decisions be made before I’m willing to move forward?What am I avoiding by insisting on the certainty and decisiveness of others?

• Where am I sabotaging possibility because I don’t control it? What version of the future feels threatening, and why?

• Do I really want a partner to share the load with me? Am I willing to trust someone else and acknowledge I can’t do everything needed to progress the mission?

• Do I see imagination as a threat to my role? What would it take for me to let my team dream without interruption?

• What paradox am I refusing to live in? What two truths am I trying to resolve that might need to be held instead?

• Who around me is offering wise resistance, and am I listening? What kind of truth am I actually willing to hear?

Click here for the tables and assessments for founders and their number twos → Chapter 6 assets.

REALITY CHECK

If you’re a founder reading this, ask yourself honestly: 

• When was the last time our actions under stress contradicted our stated values? What behaviors consistently surface when things get hard? Are they aligned with who we say we are?

• If our team had to describe our culture in three words, would those match the three words we use in external messaging? Would I be comfortable if every internal Slack message and meeting transcript were made public tomorrow?

• What do we promise to customers that our employees don’t actually get to experience? Where are we overrelying on marketing spin instead of operational integrity?

• In our last crisis, what story did our actions tell about us that our brand never would have wanted to share publicly? Do we have a plan for how to communicate with our employees first—not just our audience—when the next crisis hits?

• In what areas are our values still aspirational instead of operational? How do we measure staff performance through the lens of our values—not just metrics or output?

• What’s the story our team is telling themselves about who we are right now? Does that story inspire commitment, or is it draining their sense of purpose?

Click here for a case study of leaders who prove integrity is scalable → Chapter 7 case study.

REALITY CHECK

If you’re a founder reading this, ask yourself honestly: 

• Where am I confusing speed with progress? What decision am I rushing right now just to relieve my own anxiety?

• If all external validation was muted for ninety days, who would I be as a leader? Am I tying my worth to control and answers, or to becoming the kind of leader who can hold uncertainty?

• What am I doing for appearance’s sake that doesn’t actually serve transformation? Where am I tempted to rebrand, restructure, or pivot prematurely instead of letting current work mature?

• What needs to end (an old system, habit, or identity) before the new can emerge? Am I willing to acknowledge what’s dying, or am I clinging to it under the guise of “stability”?

• Where do I need to deliberately stop—Sabbath, rest, solitude—to allow imagination to return? What practices remind me that waiting is not passivity, but strategy?

Click here for comparison tables on strategic waiting → Chapter 8 tables.

REALITY CHECK 

If you’re a founder reading this, ask yourself honestly: 

• Am I allowing myself to fully let go of what is ending? Where am I trying to shortcut or control the process? What feelings or losses have I been avoiding?

• What old structures, habits, or assumptions am I holding on to? How are these attachments limiting my ability to imagine the future? What would happen if I let go of them, even temporarily?

• How am I modeling letting go and curiosity for my team? Are there rituals or practices I can introduce to make endings visible and honored? What messages am I sending about the value of patience and reflection?

• Am I noticing moments of awe or wonder in the midst of challenge? How can I cultivate more experiences that spark curiosity and creativity? What small daily practices could anchor me in presence and imagination?

• How is my grief shaping the vision I want to offer others? Does my current vision reflect imagination born from loss, or reaction to fear? What is the raw material of possibility I might be overlooking?

• What have I believed about letting go? Do I think it’s a sign of weakness? Am I afraid that it will bury me if I am open to it? 

• When was the last time I grieved well?If I didn’t grieve, how did I distract myself, and where do I notice myself doing that again? If I did grieve, what was my experience?

REALITY CHECK 

If you’re a founder reading this, ask yourself honestly: 

• When was the last time you felt awe? Where were you, and what were you doing? What shifted in your thinking or priorities as a result?

• What is competing for your attention right now that doesn’t deserve it? Who or what benefits from you giving your attention to it?

• What’s one way you can expose yourself (and your team) to beauty this week? What’s a small, low-cost version you can repeat regularly?

• Where are you operating at a pace that’s unsustainable, and what would slowing down look like? What is driving that pace—fear, ambition, expectation, or habit? If you slowed down, what is the worst-case scenario? What is the best-case scenario?

• What ritual can you commit to that will consistently reconnect you to awe, both personally and as a team? How will you safeguard it from being eroded by busyness? How can the team share in both the planning and the reflecting?

•  If your leadership vision moved at nature’s pace instead of a quarterly sprint, what would you do differently? What would you stop doing immediately? 

• How would that pace change the way you think about success? What would you double down on, knowing results would take longer?

Click here for a table on moving from the pace of business to the pace of nature → Chapter 10 table.

REALITY CHECK 

If you’re a founder reading this, ask yourself honestly: 

• Where are you still trying to systematize your way out of natural chaos instead of moving through it? What would it look like to stop reengineering and start reordering?

• When you encounter dysfunction in your organization, is your first instinct to look outward (“it’s them”) or inward (“what am I fueling”)? Who have you been blaming who might be mirroring something you need to work out in yourself?

• What black-and-white thinking are you starting to unhook from? Where are you now holding paradoxes you couldn’t hold six months ago?

• How are you treating the people right in front of you—your team, your neighbors, the barista? If this is a mirror of the society you’re trying to build, what does that reflection show you?

• What does your ambition look like now compared to a year ago? Are you still measuring momentum by how important it makes you feel, or by how much connection and possibility it creates?

• Where are you still clenching when you see challenges ahead instead of letting the river take you? What would it look like to loosen your grip and trust the process?

• What old standards, metrics, or version of yourself are you still comparing yourself against?What becomes possible when you stop measuring new work with old rulers?

REALITY CHECK 

If you’re a founder reading this, ask yourself honestly: 

• When was the last time the “ground gave way” under your old definitions of success? What unraveling did you notice? How did you resist the urge to run back to old metrics or personas?

• What false binary have you been living inside that no longer serves you? How has this binary shaped your leadership decisions? What paradox might you need to hold instead?

• Where in your leadership are you practicing paradox instead of certainty? How does it feel to sit in that discomfort? What new imagination has emerged because of it?

• What is the state of the “micro” in your leadership: the people, spaces, and relationships directly in front of you? Do they leave interactions with you depleted or energized? How might nurturing them change the larger “macro” culture you’re trying to build?

• Where is ambition still driving you at the expense of your soul? What small, human-scale practices could help you reclaim pace, presence, and connection? How might letting ambition unravel open up room for something truer?

REALITY CHECK 

If you’re a founder reading this, ask yourself honestly: 

• Where in your leadership are you tempted to confuse vague optimism with real hope? What’s the difference between the two in your current context? How could accountability turn that optimism into something concrete?

• Who do you currently trust enough to hold you accountable? Are you actually giving them access to the full truth? What’s one invitation you could extend this week to deepen that trust?

• What harm are you responsible for that still needs naming? Who has carried the weight of that harm? What step could you take to repair trust or mitigate damage?

• Where are you avoiding responsibility by hiding behind metrics or “good intentions”? What story (from someone impacted) could serve as a more honest mirror? What practice could you build to keep that story in front of you?

• When you imagine the future you’re working toward, how do you keep yourself tethered to reality? What guardrails prevent you from sliding into denial or fantasy? Who shares that responsibility with you?

REALITY CHECK 

If you’re a founder reading this, ask yourself honestly: 

• When was the last time you laughed so hard you lost track of time? What conditions made that possible?

• Do you believe fun is irresponsible? Where did that belief come from?

• How do you signal to your team that it’s safe to be human, not just productive?

• Where do you confuse anxiety with caring deeply? What might shift if you let go of that script?

• What activities make you forget the clock, loosen your shoulders, or hear yourself laugh out loud? And what keeps you from giving yourself permission to do them more often?

• How might joy in your leadership make your vision more magnetic? Who on your team would benefit most from seeing you enjoy the work, not just carry it?

• What would it look like this week to deliberately choose fun, not as escape, but as a practice of trust? How will you notice the difference between numbing out and truly coming alive?