Introduction
For first-time entrepreneurs, making the leap from the perceived safety of a corporate job to running your own business can feel like stepping off a cliff into the unknown. Uncertainty. Fear of failure. Fear of looking foolish. A thousand “what ifs” flood your mind, making you feel like you’re drowning in quicksand. And often, those around you—family, friends, colleagues—unintentionally amplify these doubts by projecting their own fears onto you.
I’ve been reflecting on this a lot lately as I mentor several first-time entrepreneurs, as well as someone who’s still contemplating whether to take the plunge. For some, entrepreneurship feels like a natural calling. For others, it’s an enormous and intimidating step. In my case, I was hungry for it. I yearned for it. But I was also scared to go at it alone.
I had a split influence growing up—one parent who was comfortable with entrepreneurship and another who was terrified of it. The latter believed in job security, a guaranteed salary, and the predictability of a 9-to-5. Anything outside that structure was, to them, reckless and irresponsible. Naturally, their advice reflected those fears. But here’s the interesting part: rather than absorbing that mindset, I rebelled against it. The thought of staying in the same job, in the same location, doing the same work until retirement filled me with more fear than taking a risk ever could. That fear became my fuel.
It drove me to live in six countries, launch four startups, and transition across three industries. I look back and feel deeply satisfied with my choices—not just in my career but in life. I feel like I’ve maximized every single day, and when my career eventually comes to an end, I’ll be able to say with confidence: I didn’t just tick the employment box. I truly lived.
Having Someone in the Trenches Helps
The first startup I built wasn’t on my own—I did it with a mate. And that made all the difference. Having someone in the trenches with me meant I wasn’t facing every challenge alone. The late nights, the problem-solving, the near-burnouts—it was all a little easier when there was someone else on the journey with me.
But what if you don’t have a co-founder or a like-minded friend ready to jump in? Get a mentor. Not just any mentor, but someone who’s ready to be there side by side with you. A mentor can’t make your decisions for you, but they can offer guidance, help you avoid unnecessary mistakes, and give you the confidence to keep going when doubt creeps in.
Your Life Vision Drives Your Entrepreneurial Vision
People often think entrepreneurship is the goal. But for me, it has always been part of a bigger picture—my life vision.
I never wanted a predictable, comfortable 9-to-5 that steadily ticks over. I wanted to live all over the world. I wanted adventure. I wanted to push my limits, explore new industries, meet fascinating people, and make sure that when I looked back, I had a life filled with experiences, not just work achievements.
My entrepreneurial journey is just one piece of that bigger puzzle. My life vision allows me the mental freedom to be an entrepreneur in different settings. It reassures me that I’m always working toward something meaningful. That, in itself, brings a huge sense of satisfaction.
Work is not the primary driver. My life vision is.
Entrepreneurship, for me, isn’t just about building businesses—it’s about building a life that aligns with my values, my goals, and my ambitions. My career is an enabler. It’s a tool to help me achieve my life vision. And that shift in mindset has been incredibly liberating.
The Path You Take is Yours to Define
Yesterday, I went on a 20km hike with some friends, trekking through forests and climbing steep hills. We had Google Maps to guide us, with its perfectly defined blue line marking the route. We also had another app, AllTrails, which shows paths taken by other hikers—more varied, sometimes more adventurous, but still routes that others had mapped out before us.
And then there was my route—what my wife jokingly calls “the Ben route.” At times, I ignored both Google Maps and AllTrails, choosing instead to carve my own path through the wilderness. It wasn’t always the easiest route, and sometimes I hit dead ends, but I loved the challenge of figuring it out as I went.
This, I think, is a perfect analogy for transitioning from corporate life to entrepreneurship.
• Corporate life is like the Google Maps route—clear, structured, and predictable.
• Entrepreneurship, with the support of experienced mentors, is like AllTrails—you still have guidance, but there’s far more variety and flexibility.
• And then there’s your route—completely your own, full of unknowns, but also full of possibilities that no one else has explored.
Sometimes you’ll take a wrong turn. But you can always backtrack, adjust, and move forward again. And if you need guidance, there’s no shame in tapping into the knowledge of those who’ve walked similar paths before you.
Entrepreneurship Isn’t a Straight Line—And That’s the Beauty of It
One of the biggest misconceptions about startups is that you need to go all-in on a single venture. That’s not true. In fact, I believe in always having three things on the go:
1. The primary business—your main focus and potential big success story.
2. A complementary income stream—something that leverages your network or knowledge (for me, that’s business development consulting).
3. A monetization of your learning—turning the experience you gain into something valuable for others (for me, that’s mentoring).
Diversifying your income streams helps mitigate risk and eases some of the anxiety that comes with entrepreneurship. If your startup isn’t generating revenue yet, having a side gig or a consulting service can keep you financially stable while still allowing you to pursue your main vision.
Managing Time as an Entrepreneur
Many first-time entrepreneurs worry about time. They assume that running a startup means working insane hours indefinitely. While you will put in a lot of hours at the beginning—partly because of passion, partly out of necessity—it’s not a never-ending grind.
In reality, you manage your time.
Here’s an example of my typical day (but I change this up regularly. I need variety not just in my work but also in my day. Routines need to be broken to keep me alive and inspired.)
• 6:30 AM: Start the day by checking emails and messages over breakfast.
• 7:30 AM: Hit the gym for about an hour—sometimes I use this time to brainstorm, sometimes I completely switch off.
• 9:00 AM: Begin focused work—this could be at home, a coworking space, or a coffee shop.
• 12:00 PM: Take my dog for a walk and make important calls.
• 1:00 PM: Have lunch with my wife.
• 1:30 PM - 5:00 PM: Back to work. Except Fridays. Fridays, I finish at 12 noon and spend the afternoon with my wife.
• 5:00 PM: Pick up my son from school and be a parent and husband.
• 8:00 PM: If needed, I do a bit more work, usually from the sofa or home office. This doesn’t always mean sitting in front of a laptop. It can be thinking things over, mulling ideas, or pinging my business partner on WhatsApp.
Thursdays and Fridays are flexible—sometimes normal days, sometimes early starts if I have calls with Asia. On Saturdays, I often write blog posts or brainstorm business ideas while at the gym.
And if I need time off? I take it.
That’s the beauty of this life—it’s dynamic. I constantly change up my routine to stay fresh and engaged.
Quarterly Rewards: Taking Time to Reset
Another thing that keeps me motivated is having quarterly rewards—holidays with family or friends.
These don’t need to be extravagant or long. It could be:
• A long weekend getaway.
• A staycation.
• A camping trip.
• Or even a big, well-deserved vacation.
The point is to have something every quarter to break the routine, reset, and just enjoy life with the people who matter most. It’s easy to get lost in the hustle of entrepreneurship, but taking time to step back, reflect, and enjoy life makes it all the more worthwhile.
Do You Really Want a Straight Line?
At the end of the day, ask yourself: Do I really want my life to follow a straight, predictable path?
If your answer is yes, then corporate life may be the right fit for you. But if you’re reading this and feeling a flicker of curiosity—if there’s even a small part of you that’s thinking maybe no—then entrepreneurship, or at least working in a startup, might be something worth exploring.
It’s not always easy. It comes with challenges, setbacks, and moments of doubt. But it’s also exciting, fulfilling, and, above all, yours to define.
So, if you’re standing at the edge of that metaphorical cliff, wondering whether to take the leap, know this:
There’s no perfect time.
There’s no perfect plan.
There’s just the decision to start.
And once you do, you might just find that the path you carve for yourself is far more rewarding than any predefined route ever could be.