So you want to be an entrepreneur?
The question I hear most from people thinking about leaving their jobs to start their own business is:
“What does it take to make the transition?”
For many, there seems to be an invisible wall separating the world of employment from entrepreneurial life. And, of course, the grass always looks greener on the other side. What they really want to know is how to climb over this wall, land on the other side—and survive.
Having transitioned from a long corporate career to starting my own software company, I’ve learned that making this leap requires major mental shifts.
To help you prepare, let’s explore the questions you need to ask yourself before taking the plunge.
“Can you handle peak emotional states?”
Entrepreneurship is a mental rollercoaster. Extreme highs and crushing lows are part of the game, and you need to be able to navigate them.
In traditional employment, emotions tend to stay within a predictable range. A 10% raise after a performance review feels good, but you’ll never double your income overnight. If you make a mistake, you might feel bad, but your paycheck still arrives on time. It’s a stable emotional landscape.
Entrepreneurship is the opposite. If your idea fails, you don’t just feel bad—you feel devastated. If you struggle to gain traction, the financial stress can make you question everything. But when things go exceptionally well, and you triple your revenue in a month, you’ll feel an exhilarating high that no employee ever experiences.
These peak emotions make you feel truly alive, but not everyone can handle them. Can you?
“Can you handle family and peer pressure?”
Even if you can manage the emotional swings, there’s another challenge: the people around you.
Entrepreneurs experiment, pivot, and adjust constantly. There’s no clear-cut process, no standard operating procedure. To outsiders, this can look like you have no idea what you’re doing. Family and friends may question your decisions, making you doubt yourself just when you need confidence the most.
This kind of pressure can be demotivating, especially in the early days when quitting still feels like an option. Can you push through despite it?
“Can you let go of the idea of working 9 to 5?”
Entrepreneurs work when work needs to get done. If a customer in a different time zone wants a call at 5 AM, you take it. There’s no HR department setting your work hours.
Over time, you can build a system that allows for more structured hours, but in the beginning, that’s rarely an option. Success in entrepreneurship demands flexibility. Are you ready for that?
“Do you work for passion or for security?”
For many, life’s primary goal is stability—raising a family, buying a home, and saving for retirement. They treat each paycheck as a step toward long-term security. And that’s perfectly fine.
Entrepreneurs, however, are driven by passion. They have a calling to create something new, whether big or small. Their happiness—and even their sense of purpose—depends on bringing their vision to life.
Professional athletes train every day, pushing their limits to compete at the highest level. Entrepreneurs do the same. If security is your top priority, this path may not be for you. But if passion drives you, what is your calling? If you’re not sure, figure it out before you take the leap.
“Are you able to let go of the idea of biweekly paycheques?”
Once you step into entrepreneurship, no one owes you a paycheck. Instead, you have to generate consistent cash flow to cover expenses, pay your team, and pay yourself.
In the early stages, your income may be irregular. There are no guarantees. Your ability to secure loans, mortgages, or credit may take a hit. Even if you have savings as a financial runway, that only buys you time—it doesn’t guarantee success.
Are you ready to work without the security of a steady paycheck?
“What is your tolerance for ambiguity?”
When you’re employed, everything is clear. Your tasks are defined, and as long as you deliver, you get paid.
Entrepreneurship is different. No one tells you what to do next. If you can’t figure it out yourself, everything stalls. You must have the discipline to keep moving forward—even when the next step is unclear.
This applies to your co-founders as well. If someone on your founding team constantly asks what they should do next, that’s a red flag. Entrepreneurs must be proactive problem-solvers.
How well do you handle uncertainty?
“Are you willing to do what it takes to get paying customers?”
Many aspiring entrepreneurs are stuck in motion—reading books, watching videos, and attending seminars—but never taking action. Why? Because the fear of quitting their job never goes away.
The only way to overcome this fear is to prove to yourself that you can generate paying customers. That’s it. If you can sell something before quitting your job, the decision to leave becomes an afterthought.
No one is waiting for another app. Your idea isn’t needed—yet. Have you validated it? If you’re not willing to sell, you can’t build a business. It’s that simple.
“Are you process-oriented?”
Corporate jobs train employees to follow processes. Large companies rely on processes to ensure consistency. As a result, employees are rewarded for following rules and punished for deviating from them.
Entrepreneurs, however, challenge processes. They innovate by breaking old habits and finding better ways to do things. Processes create overhead, slowing things down. When you’re in control of your own time, you realize how much more you can accomplish without unnecessary bureaucracy.
If you hate rigid processes, that’s a sign entrepreneurship might be right for you.
“Are you willing to let go of a promising career?”
A job and a career are not the same. Careers follow an upward trajectory within organizations. Ambitious professionals can achieve their goals faster within a structured career path than by going solo. They understand office politics, work the system, and climb the corporate ladder effectively.
Jobs, on the other hand, go nowhere. If your job doesn’t offer growth, entrepreneurship might be your best option for getting ahead.
Are you willing to walk away from a promising corporate career to build something of your own?
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If you’ve reflected on these questions and still feel ready to take the leap, my advice is simple: start by finding someone who is willing to pay you for something you will do or make. That’s your first step. Then learn the art of making offers.
And remember—no one is born an entrepreneur. It’s a skill you develop and a muscle you train.
Good luck!