In 2018 I was Group CISO at a major bank, running cybersecurity across dozens of countries, and I was also quietly building my first real business on the side. Cyber Leadership Institute started as an idea I tested in the margins of my week: early mornings, weekends, the occasional lunch hour spent writing course material instead of eating at my desk. Within two years it was generating seven figures, and I was still employed full-time when it crossed that line.
I am not telling you that story to impress you. I am telling you because the single biggest misconception about starting a business is that you need to quit your job first. You do not. In fact, quitting before you have built anything is one of the riskiest moves you can make, especially if you are a senior executive with a mortgage, a family, and a lifestyle built around a salary that took decades to reach.
What follows is the 90-day framework I now teach to executives who want to build something of their own while still collecting a pay cheque. I need to be upfront about what 90 days actually delivers: a tested foundation, not a cash-flowing business. Anyone who tells you that you can go from zero to profitable in three months while working a demanding corporate role is either lying or selling you something. But 90 days is enough to know whether your idea has legs, whether people will pay for it, and whether you actually want to do this, which is more progress than most people make in years of thinking about it.
Why most people never start (and why that is actually rational)
Most people fail to escape corporate not because they lack ambition but because they lack the financial foundation to do so safely. That is not a character flaw. It is a planning problem.
When you earn $300,000 or $400,000 a year, the gap between what you earn and what you could earn from a brand-new business feels enormous. So you keep waiting. You wait until you have "enough" saved, until the idea is "fully formed," until you feel "ready." And that wait stretches from months into years, because none of those conditions are ever perfectly met.
The fix is not to be braver. The fix is to treat starting a business as a process rather than a single event, and to run that process while you still have the safety net of a salary underneath you.
Before you build anything: know your number
Kristy Shen calls it the freedom number, and it is the single most important calculation you will do before any business planning starts. Your freedom number is not what you want to earn or aspire to have. It is the minimum you actually need to cover your life without a corporate salary.
Start with your annual burn rate: total household expenses minus any passive income you already have (rental income, dividends, a partner's salary if that is part of your joint plan). That gap is what your business eventually needs to fill, and knowing the exact figure changes everything about how you think about this project.
If your burn rate is $180,000 a year and you have $60,000 in passive income, your freedom number is $120,000. That is a very different target from the $400,000 salary you are currently earning, and it is a much more achievable one for a new business in its first few years.
Most executives skip this step because it feels too simple. But without it, you are building towards a vague idea of "enough" that keeps shifting every time you look at it.
The 90-Day Freedom Formula
This framework splits 90 days into three distinct phases. Each one has a specific output, and you should not move to the next phase until the current one is done. The temptation will be to jump straight to building a product. Resist it. Foundation work is not exciting, but it is the difference between a business that lasts and one that burns out in six months.
Days 1 to 30: The foundation
The first month is entirely about clarity and financial reality. No product building, no branding, no website. Just honest answers to the questions that matter.
- Calculate your freedom number. Run the burn rate exercise above. Write it down. Put it somewhere you will see it every day.
- Audit your time. Track how you actually spend your hours for two weeks. Most executives discover they have more recoverable time than they thought, usually in the form of low-value meetings, excessive email, and evening screen time that could be redirected.
- Define what you are building and for whom. This is the Concept and Hypothesis stage of my CHAOS framework. What specific problem are you solving? Who has that problem? Why would they pay you, specifically, to solve it? If you cannot answer those three questions in plain language, you are not ready to build anything yet.
- Set your weekly build schedule. Block out the actual hours you will dedicate to this project each week. Be realistic. Five focused hours per week is more productive than a vague intention to "work on it when I can."
Days 31 to 60: The prototype
Dan Koe said something that stuck with me: "The only way to control your income, and therefore your life, is to create a product." He is right, but the product you create in month two should be the minimum viable version, not the polished final thing.
This is what I call the Minimum Viable Exit. You are not trying to build a perfect business. You are trying to answer one question with real evidence: will someone pay for this?
- Build the simplest version of your offer. If it is a consulting service, outline the engagement and find one person to test it with. If it is a digital product, create a landing page that describes it and see if anyone signs up. If it is a course, teach the material live to a small group before you record anything.
- Talk to your audience. This is the Audience stage of CHAOS. Have ten genuine conversations with people who fit your target market. Not surveys, not social media polls. Actual conversations where you listen more than you talk. What you learn in those ten conversations will reshape your offer in ways you cannot predict from your desk.
- Make your first offer. Before the end of month two, put a price on something and offer it to someone. It does not need to be expensive. The point is to cross the psychological line from "thinking about a business" to "running a business."
Days 61 to 90: Validation and systems
The final month is about turning early signals into a repeatable process. You are still employed, so everything you build needs to run without you being available eight hours a day.
- Evaluate what happened. Did people pay? Did they respond well? What feedback did you get? Be honest with yourself here. If nobody wanted what you offered, that is valuable information, not failure. Adjust the concept and test again.
- Build your first systems. Identify the tasks you do repeatedly and create simple processes for them. This could be an email template for enquiries, a scheduling system for calls, or a content calendar for building visibility. The goal is to protect your productive hours, because you will have fewer of them than a full-time entrepreneur.
- Set your next 90-day target. Based on what you learned, decide what the business needs to look like at the six-month mark. This is where most people either recommit with better information or pivot to a different idea, and both outcomes are perfectly fine.
The time problem (and why it is smaller than you think)
Every senior executive I work with raises the same objection: I do not have time. And when I look at their calendars, they are right. They are packed from 7am to 7pm with meetings, travel, and the kind of operational work that fills every available minute.
But time is not really the constraint. Priority is. When I was building CLI alongside my CISO role, I did not find extra hours in the day. I made different choices about how I used the hours I already had. I stopped watching television most evenings. I got up at 5am three days a week. I said no to social commitments that did not matter to me. None of that was heroic. It was just a decision about what I wanted more.
You need somewhere between five and ten hours a week to make meaningful progress in the first 90 days. If you genuinely cannot find that after auditing your time, the problem is not your schedule. The problem is that you are not ready to start, and that is fine too. Better to know now than to start and abandon it three weeks in.
What 90 days will not give you
I want to be direct about this because too many people sell the fantasy of quick results. After 90 days of disciplined work alongside your job, you will have clarity on your business concept, early evidence of whether it works, basic systems to keep it running, and a realistic plan for the next phase.
What you will not have is a business that replaces your salary. That takes longer, typically 12 to 24 months of consistent building, and it depends entirely on the type of business, your market, and how much time you can invest. The 90-day framework builds the foundation that makes everything after it possible. Skipping the foundation is how you end up six months in with no customers, no clarity, and a growing pile of regret about time wasted.
The real risk is doing nothing
I am not here to tell you that corporate careers are bad. Thirty years in corporate built everything I have today: the expertise, the network, the credibility, the leadership skills that made CLI possible and that now make my coaching business possible. Corporate gave me all of that, and I am grateful for it.
But depending entirely on a single salary with no assets underneath it is a vulnerable position, and it is getting more vulnerable every year as AI reshapes industries and eliminates roles that seemed untouchable. The question is not whether you should quit. The question is whether you are building anything outside your job that would catch you if the job disappeared tomorrow.
Ninety days is enough to start answering that question with action instead of anxiety. You do not need to quit, you do not need permission, and you do not need to have it all figured out before you begin. You just need a clear framework, a few hours a week, and the honesty to test your idea against reality instead of letting it live forever as a daydream.