UpTrajectory Review

Jerry Colonna, the executive coach who built his reputation guiding founders through the psychological wreckage of startup culture, returns to familiar territory: the moment when ambition curdles into something destructive. His Inc. column takes on the performance pressure that founders and CEOs not only endure but often weaponize against themselves and their teams. Colonna's argument, drawn from decades of coaching sessions with venture-backed leaders, is that the very drive that propels people into entrepreneurship can become a blind spot that hollows out organizations from within. The piece lands at a moment when founder mental health has finally entered mainstream business conversation, though solutions remain thin on the ground.

For small-business operators without venture capital cushions or boards of directors, Colonna's framing carries particular weight. The pressure to perform in a small business is rarely about hitting growth metrics for investors; it is about making payroll, retaining employees who could earn more elsewhere, and justifying the personal financial risk that founders and their families absorbed. When that pressure becomes identity-defining, decision-making suffers in ways that are harder to mask than at larger companies. A founder who cannot separate self-worth from quarterly results will delay necessary pivots, avoid difficult conversations, and model unsustainable behavior for a team that has nowhere else to look for cultural cues. Colonna's lens suggests that the damage starts earlier and runs deeper than most operators acknowledge.

What distinguishes this piece from the growing genre of founder-wellness content is Colonna's refusal to treat pressure as an external force to be managed. He frames it as a leadership problem precisely because leaders actively construct and reinforce it, often unconsciously. This is where skepticism is warranted: the column's brevity leaves underexamined the structural conditions that make performance pressure feel mandatory. Small-business owners operate in environments where one lost contract or delayed payment can trigger cascading consequences. The advice to examine one's relationship with pressure risks sounding like individual therapy substituting for systemic support, especially when access to quality executive coaching remains economically out of reach for most operators.

The downstream effects of unexamined performance pressure reshape organizations in predictable patterns. Teams learn to prioritize visibility over value, producing work that signals effort rather than solves problems. Middle managers in growing small businesses absorb the founder's anxiety and transmit it downward, creating retention problems that are rarely traced to their source. Customer relationships suffer when every interaction becomes a transaction to be optimized rather than a relationship to be built. Perhaps most insidiously, the founder's inability to model sustainable behavior becomes a ceiling on the business's growth; investors and acquirers increasingly diligence leadership team stability and cultural health, factors that are difficult to retrofit.

Operators should watch for the specific symptoms Colonna identifies: the redefinition of exhaustion as virtue, the conflation of busyness with effectiveness, and the reflexive dismissal of rest as indulgence. More practically, this piece suggests an actionable audit. Examine the last five decisions where speed was prioritized over deliberation; how many were genuinely time-constrained, and how many reflected an unexamined assumption that faster equals better? The question of what to do next is harder. Colonna's work consistently points toward peer support structures and professional coaching, but small-business operators might start with more accessible interventions: structured feedback from direct reports about decision-making pace, explicit permission-giving to team members about sustainable work patterns, and the difficult practice of measuring output rather than hours visible.

“Pressure makes performers of us all — leaders included.” — Inc. Magazine

Takeaway: Audit your last five rushed decisions to distinguish genuine urgency from unexamined performance anxiety.