Making Mischief, Navigating Self-Doubt & Cultivating Leadership with Andy Sparks

Lead through self-doubt by turning private threat into visible support and clean action

The practical answer from Jonny Miller’s conversation with Andy Sparks is this: self-doubt is not solved by waiting until you finally feel like a “real” leader. It becomes workable when you notice the body threat early, write down what you are afraid of, build a support network before crisis, and create leadership habits that keep your team from having to absorb your unprocessed fear.¹

Andy’s story is useful because it is not a polished founder myth. He talks about shutting down an early company, losing identity, feeling deeply depressed, working with an executive coach, learning to notice emotional triggers in meetings, and slowly building a different way to lead Holloway with his cofounder Josh.²³

Use this guide when you are:

• leading while quietly wondering whether you are qualified;
• reacting to conflict, criticism, or uncertainty faster than you can explain;
• trying to build trust with a cofounder, partner, team, or peer;
• lonely in a role where people expect you to look composed;
• ready to replace heroic self-reliance with a more intelligent support system.

✻1This is a leadership and nervous-system practice guide, not medical advice, crisis care, therapy, or a substitute for qualified support. Andy discusses depression and suicidal thoughts in the episode. If you are in immediate danger, thinking about harming yourself, or unable to stay safe, contact local emergency services or a crisis line now. If depression, anxiety, trauma symptoms, burnout, or substance use are persistent or destabilizing, involve a licensed professional and move slowly.

Convert self-doubt from an identity verdict into a named signal

After closing his first company, Andy describes a familiar founder collapse: “What skills do I have? What do I have to offer?” He had wanted meaningful work, independence, and proof that he could build something — then failure made the whole identity structure feel unstable.¹

The tactical move is to stop treating self-doubt as a global truth and translate it into a specific signal.

Self-doubt sentence	Likely signal underneath	Cleaner leadership response
“I’m not good at anything.”	Identity collapse after a setback	List actual skills, relationships, and next constraints separately.
“If this fails, I fail.”	Outcome and self-worth are fused	Define the experiment, the learning, and the support you need if it does not work.
“I need more authority.”	Fear of irrelevance or replacement	Ask where ownership is actually useful, not where status feels soothing.
“I should hide this from my team.”	Shame is trying to protect competence	Share the appropriate amount of uncertainty plus the next clear step.
“I should already be over this.”	Judgment layered on top of pain	Name the pattern without turning it into another reason to attack yourself.

This is where cautious self-compassion research is relevant. Kristin Neff’s work frames self-compassion as self-kindness, common humanity, and mindful awareness during difficulty.⁸ That does not mean bypassing accountability or pretending every leadership behavior is fine. It means the part of you that is scared does not become more trustworthy just because you shame it.

Try this sentence before making a big move from self-doubt:

“A threat signal is here. It may contain useful information, but it is not qualified to define my whole identity or choose the next step alone.”

Then ask three concrete questions:

1. What happened? Name the external event without interpretation.
2. What did my body do? Pulse, jaw, chest, belly, heat, collapse, numbness, urgency.
3. What support or action would be proportionate? A note, a conversation, a walk, a coach call, a decision memo, a night of sleep.

Notice the trigger before it becomes the meeting

Andy’s executive coach helped him learn a deceptively simple skill: notice when a meeting starts one way and your state suddenly changes. Maybe you entered relaxed, then your pulse rises, anger appears, and the body starts treating the room like an attack.²

That moment matters because a leader’s nervous system is contagious in ordinary, non-mystical ways: your tone, speed, defensiveness, silence, and urgency become part of the room. You do not need to be perfectly regulated. You do need enough awareness that your team is not forced to decode your unmanaged activation.

Use this trigger protocol in live conflict:

Stage	What to notice	What to do
Before	Baseline: relaxed, focused, rushed, hungry, already braced	Do one short reset before the meeting if you are already activated.
During	The state shift: pulse, heat, tunnel vision, urge to interrupt, sudden silence	Pause, breathe out longer, feel your feet, and buy time with one clarifying question.
After	The story: “they attacked me,” “I’m not respected,” “this always happens”	Write the story down, then separate data from interpretation.
Repair	Any impact your state had on others	Name only what is useful: “I got reactive there. Let me restate what I actually mean.”

Emotion-regulation research should be applied carefully, but James Gross’s work on reappraisal and suppression is a useful warning: looking calm by suppressing expression is not the same as being regulated.⁹ The aim is not to become blank. The aim is to create enough space that anger, shame, or fear can inform you without driving the whole conversation.

For a simple pre-meeting reset, use NSM’s Reset Your Nervous System guide before hard decisions, investor calls, or cofounder conversations.

Build a support network before you need one

Andy describes one of the most practical leadership maps in the episode: a support network with different people serving different roles — cofounder, coach, mentor, advisors, peers, friends, and people who simply understand the emotional texture of building something hard.⁴

The point is not to outsource responsibility. The point is to stop asking one person, one partner, one cofounder, or one team to be your entire village.

Role	What they are for	What they are not for
Coach or therapist	Pattern recognition, crisis reflection, emotional work, hard questions	Guaranteeing business outcomes or making decisions for you
Mentor	Long-context guidance over time	Daily execution or constant availability
Advisor	Focused expertise on a specific domain	Emotional holding for every founder fear
Peer friend	Mutual honesty, normalization, “you’re not alone”	Professional treatment or strategic certainty
Cofounder / partner	Shared reality, trust, clean conflict, mutual accountability	Absorbing every unprocessed wound without limits
Team	Feedback, execution, truth from the work	Becoming your emotional regulation system

Andy’s Friday conversations with a close founder friend are a good example: they are not primarily about solving each other’s problems. They are about being known by someone with enough shared context that the week can metabolize.⁴

This also links to loneliness. Andy calls loneliness a profound, often unnamed problem and connects it to the need to deliberately assemble a village.⁵ That does not mean friendship cures depression or removes business risk. It does mean isolation is not a neutral leadership strategy.

A practical audit:

1. Who can hear the truth without immediately fixing, flattering, or panicking?
2. Who is allowed to challenge you when you are about to betray your values?
3. Who has enough domain context to advise, but not so much entanglement that they need a specific answer?
4. Who helps you remember your body, relationships, and life outside the company?
5. Where are you asking one person to be five different kinds of support?

For adjacent NSM conversations, see Leadership, Belonging, and the Art of Growing Up with Jerry Colonna and Full Aliveness and Conscious Leadership with Jim Dethmer.

Practice

Run the 20-minute self-doubt support map

Use this when self-doubt has become repetitive, private, and global — especially before a hard conversation, fundraise, launch, hiring decision, or relationship repair.

1. Name the live doubt. Write one sentence: “The doubt I keep looping on is ___.” Keep it specific.
2. Locate the threat. Ask what feels at risk: belonging, competence, money, status, freedom, love, control, reputation, or safety.
3. Separate signal from story. Write two columns: “Real data I need to address” and “Identity story my nervous system is adding.”
4. Pick the right support role. Do you need a coach, therapist, mentor, advisor, peer, cofounder, friend, or doctor? Do not send everything to the same person by default.
5. Make one clean ask. Examples: “Can you listen for ten minutes?” “Can you challenge my assumptions?” “Can you help me think through options?” “Can you remind me what I value?”
6. Choose one proportionate action. Write the memo, ask for input, repair the comment, schedule the call, sleep before deciding, or take the first small step.
7. Review the residue. After the support or action, ask: am I clearer, more connected, and more adult — or still performing, hiding, and spiraling?

The goal is not to eliminate self-doubt. The goal is to stop making private threat choose public behavior.

Turn trust into repeatable leadership mechanics

The most useful part of Andy’s leadership evolution is how unglamorous it becomes. He writes more. He clarifies decisions. He notices repeated concerns. He keeps a leadership page. He thinks about the job of a CEO as being the calmest person in the room, running toward hard things, making as few decisions as possible, encouraging important ideas to be written down, and using a consultative decision-making model when appropriate.⁶

That is the opposite of vague “be more resilient” advice. It gives the nervous system rails.

Leadership problem	Mechanic that helps	Why it regulates the system
People feel unheard	Collect input before the decision; reflect what changed and what did not	Reduces ambiguity and hidden resentment
Cofounders trigger each other	Share personal patterns, biases, and “what sets me off” before conflict	Makes activation less mysterious and less personal
Remote teammates feel transactional	Begin with human contact; schedule informal walks or Zoom lunches	Builds trust before urgency consumes the relationship
Founder urgency spreads	Model time off, avoid performative holiday work, reduce Slack pressure	Shows the team what is actually permitted
Important ideas vanish in meetings	Write them down for asynchronous consumption	Gives people time to think without live threat dynamics

Andy also names a subtle cofounder repair sentence: “I am not mad at you right now. I am just mad at this situation.”³ That sentence is powerful because it separates relational threat from problem intensity. The problem can be hard without the relationship becoming the battlefield.

Psychological safety research is relevant here, with caution. Amy Edmondson defined team psychological safety as a shared belief that a team is safe for interpersonal risk-taking and found it related to learning behavior in work teams.¹⁰ That does not mean every workplace should become emotionally unbounded. It means people need enough safety to offer input, name mistakes, and challenge assumptions without fearing humiliation or punishment.

Three leadership habits to install this week:

1. Decision preface: “I want input before I decide. I may still choose differently, but I want to understand what you see.”
2. Trigger transparency: “I notice I’m getting reactive. I’m going to slow down so I do not make this about you.”
3. Remote human opening: “Before we get into tasks, how are you actually doing after the break / weekend / launch?”

For more on leadership as initiation rather than performance, read Wilderness, Rites of Passage, and Leadership with Brooks Barron.

Keep mischief in the system without letting chaos drive

Andy names “mischief” as one of the values he had been trying to articulate: a little rowdy, unruly, and willing to make useful trouble.⁷ This matters because self-doubt often makes leaders either rigid or performative. They become very serious, very strategic, very polished — and slowly less alive.

Mischief is not recklessness. It is a regulated form of creative irreverence.

Mischief is useful when it…	Mischief becomes avoidance when it…
loosens seriousness enough for truth to appear	dodges accountability or repair
helps the team question stale assumptions	humiliates people or creates confusion
brings play into hard work	masks fear of committing
keeps values alive under pressure	becomes an identity costume
allows honest experiments	refuses adult constraints

A good leadership question is: What would add 5% more mischief without reducing trust?

Examples:

• Name the obvious tension with warmth.
• Write the weird first draft before the polished memo.
• Ask the question everyone is politely avoiding.
• Create a ritual that makes hard work feel more human.
• Let the team see appropriate uncertainty, humor, and sincerity together.

The deeper move is to pair mischief with responsibility: enough play to keep the organism alive, enough structure to keep the work trustworthy.

Key takeaways

• Self-doubt is more workable when translated into a specific threat signal rather than treated as a verdict on your identity.
• Leaders need to notice state shifts early because unprocessed activation becomes part of the room.
• Support networks should be role-diverse; one person should not have to be coach, therapist, mentor, advisor, peer, and village.
• Trust is built through repeatable mechanics: written clarity, input before decisions, repair sentences, human contact, and explicit norms.
• Mischief can be a leadership value when it brings play, honesty, and creative trouble without undermining trust.
• Depression, suicidal thoughts, trauma symptoms, and severe burnout require qualified support. Do not turn leadership practices into a substitute for care.

Free assessment

Take the free nervous system assessment.

If self-doubt, reactivity, loneliness, or leadership pressure make it hard to tell clean action from threat-driven effort, the assessment can help you map your current nervous-system patterns and choose a steadier next experiment.

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Continue exploring

• Read Leadership, Belonging, and the Art of Growing Up for a deeper conversation on founder identity, belonging, and adult responsibility.
• Read Full Aliveness and Conscious Leadership for another practical lens on reactivity, presence, and conscious leadership.
• Read Wilderness, Rites of Passage, and Leadership for a guide to leadership thresholds, initiation, and maturity.
• Read Reset Your Nervous System for simple regulation practices before hard conversations or decisions.

References

1. Andy Sparks and Jonny Miller, Making Mischief, Navigating Self-Doubt & Cultivating Leadership with Andy Sparks, 05:35–16:30. Andy describes being fired, moving to California, shutting down his first company, feeling out of money and unsure of his skills, and later recognizing how much identity and confidence were involved. ↩
2. Sparks and Miller, Making Mischief, 17:08–19:33. Andy describes working with executive coach Christina Harbridge and learning to notice feelings, pulse, anger, and reactivity as they arise in meetings and relationships. ↩
3. Sparks and Miller, Making Mischief, 27:34–30:47 and 55:15–58:16. Andy discusses working with his cofounder Josh, using coaching to build trust, and learning to talk about the personal patterns and triggers each person brings to work. ↩
4. Sparks and Miller, Making Mischief, 32:24–35:16. Andy describes a support-network diagram with roles including cofounder, coach, mentor, advisors, and peer friends with shared founder context. ↩
5. Sparks and Miller, Making Mischief, 39:30–40:18 and 1:19:04–1:22:03. Andy names loneliness as a major issue, encourages finding people to talk to, and suggests vulnerability and explicit friendship-building as part of creating support. ↩
6. Sparks and Miller, Making Mischief, 58:54–1:07:17. Andy describes writing more as a leader, his Notion leadership page, the job of a CEO, consultative decision-making, decision input, and remote-team practices. ↩
7. Sparks and Miller, Making Mischief, 36:31–38:02. Andy describes “mischief” as a value: being a little rowdy, unruly, and willing to make useful trouble rather than becoming overly serious. ↩
8. Kristin D. Neff, “Self-Compassion: An Alternative Conceptualization of a Healthy Attitude Toward Oneself,” Self and Identity 2, no. 2 (2003): 85–101. This supports a cautious distinction between mindful self-kindness and self-attack; it does not imply that self-compassion alone treats depression, trauma, anxiety, or burnout. ↩
9. James J. Gross, “Antecedent- and Response-Focused Emotion Regulation: Divergent Consequences for Experience, Expression, and Physiology,” Journal of Personality and Social Psychology 74, no. 1 (1998): 224–237, https://doi.org/10.1037/0022-3514.74.1.224. Gross’s work is a cautious bridge for distinguishing regulation strategies; it should not be reduced to a universal rule that one technique is always best in leadership conflict. ↩
10. Amy Edmondson, “Psychological Safety and Learning Behavior in Work Teams,” Administrative Science Quarterly 44, no. 2 (1999): 350–383, https://doi.org/10.2307/2666999. This supports the importance of interpersonal risk-taking for learning behavior; it does not mean teams should have no boundaries, standards, or accountability. ↩