From Burnout Boardroom to Async Empire: How I Reclaimed 20 Hours/Week as a Second-Act CTO

November 9, 2025

At 2:17 AM I was still on my laptop, fine-tuning a board deck for a $6B transformation. Six hours later I was expected to walk directors through regulatory milestones, delivery risk, and a cross-continent engineering program. This was supposed to be the season where I advised as a fractional CTO, not relive the calendar chaos of Big 5 consulting. Yet there I was—living in meetings again, reacting to “quick syncs,” and sacrificing the strategic thinking my clients actually needed.

The wake-up call wasn’t loud—it was a steady nudge on a worn-out heart: If I keep working like this, I’ll miss the good life that was entrusted to me.

So I tore down the way I worked and rebuilt it around one idea: run a seven-figure fractional CTO practice without surrendering my calendar or my health. That meant creating an async operating system that delivers enterprise-grade outcomes with almost zero standing meetings.

Today I deliver 92% of engagements on time, do deep technical work I enjoy, and finish most days before dinner. This is the operating system I install for second-act founders who value legacy, leverage, and their sanity.

When Winning Started to Feel Like Losing

Corporate technologists—especially the second-act executives I partner with—carry a specific tension: you know how to scale, but the operating model you inherited thrives on status meetings, shadow PMOs, and reactive fire drills. You crave strategic space yet keep whispering “just one quick sync” to unblock finance, security, or compliance.

I broke down every recurring touchpoint across the transformation. It turned out I wasn’t directing the program; I was hosting a never-ending set of rituals that gave everyone optics but me the oxygen to architect real change.

Every pattern screamed the same thing: I was still designing my workday around other people’s urgency, not around the outcomes my clients were actually buying—clarity, technical leadership, and reliable execution.

Designing the Async Operating System

I rebuilt the business with three promises that now anchor every engagement in Rewired’s service architecture:

1. Outcome over presence. Clients buy completed roadmaps, provable velocity, and clean architecture—not my attendance in meetings.
2. Transparent systems beat real-time status. Share dashboards, Looms, and narratives people can consume on their schedule.
3. Deep work deserves a moat. Protect four-hour creation blocks so code, strategy, and hiring decisions are thoughtful, not reactive.

Here’s how those promises show up in enterprise reality:

Net: 20 hours/week restored—and more importantly, creative headspace returned.

Five Levers Every Second-Act Founder Gets

1. The Monday Loom Brief

Seven minutes. Recorded once. It answers three questions: What shipped? What’s next? What decisions do I need from you? Founders watch on their schedule—often during a walk, not in a gridlocked Zoom.

2. Quality Guardrails Without The Grind

Automated checks, compliance gates, and playbooks replace daily engineering huddles. You still get a clear readout of health and risk, but intervention is saved for strategic inflection points—not syntax disputes.

3. The “No Surprises” Control Tower

A living Notion hub tracks momentum, regulatory dependencies, and executive-ready metrics. When treasury or security moves the goalposts, the dashboard reflects it instantly—no “jump on for five minutes” required.

4. The Monthly Strategic Deep Dive

The only standing live session: 90 minutes of roadmap and portfolio risk, 30 minutes of Q&A. It’s recorded, summarized, and annotated so finance, operations, and product stay aligned without dragging you back live.

5. The Founder Off Switch

Monitoring and on-call coverage keep the program steady when you focus on capital raises or customer councils. Structured runbooks and weekly health summaries turn absence into a feature, not a liability.

Proof the System Works

Build Your Async Empire

If you’re a second-act founder who wants a product you’re proud of and a calendar you actually own, start here:

1. Cancel every recurring technology meeting for the next 30 days.
2. Stand up a Loom + Notion cadence for status, decisions, and dashboards.
3. Automate your quality guardrails so you only weigh in on strategic decisions.
4. Share this framework with your leadership team so expectations align.

Download the full Async Playbook → Async Empire Kit (Playbook)

Ready to Reclaim Your Calendar?

Let’s sketch your async operating system in 15 minutes. We’ll map the levers, pick the right retainer tier, and decide how quickly you want it running.