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Are You Ready to Chase Your Entrepreneurial Dream? 5 Questions to Help You Decide

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As a techie in your 30s, you may feel you’re past the age for your entrepreneurial adventure. Perhaps sometimes you debate if  you should give it a shot after all – for if not now, then when? But are you ready to give up the stability offered by your high-paying tech job? How do you know if the time is right? 

Here are 5 questions which will help you answer if you are truly ready to be an entrepreneur?

1. Every Thanksgiving, ask yourself:  “Am I excited about next year?”

Leaving a fat, stable paycheck to jump into the unpredictable, unknown world of entrepreneurship is hard! So, when do you know it’s time? Make it a rule to ask yourself every thanksgiving – in my current role, am I truly looking forward to next year? Am I excited?

If your answer is anything other than “Hell, yeah”. You need to move. You are ready for a change. And its probably time you seriously consider your entrepreneurial dream. Follow Jeff Bezos’s famous regret-minimization-framework which begs the simple question – In X years, will I regret not doing it?

As Bezos himself puts it: “I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed, I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried.”

2. Do you have financial and emotional support?

We often think that if we get married, we may not be able to accomplish our entrepreneurial dream. The truth is the opposite. A partner can be the biggest support you can have in the lonely journey of an entrepreneur. Not to mention how much of a financial support they can be during the tough times.

Your closest friends are not to be underestimated either. When nothing goes your way, all you want is a shoulder to lean on and someone to motivate you. Make sure you have your social-support system. Network with other entrepreneurs. Only they truly understand what you are going through.

3. Are you ready to put your money at stake and maybe lose it all?

Scroll through LinkedIn and you will constantly read about startups getting funded with millions of dollars. You start to believe that all you need is an idea and you will raise money. But, speak to any entrepreneur who has raised money and they will tell you about the time and money they poured into the business to get traction before they got any attention from investors. So, are you ready to put your hard-earned money at stake and in the worst case, lose it all? 

4. Are you ready to get your hands dirty?

As an entrepreneur, you will be a one-person-army. And for a long time! As a tech entrepreneur, you may very well be an engineer one day and a salesperson making cold calls the next. If you are a food entrepreneur, then you are the cook, the manager, the server, and the dishwasher. Whatever your venture is, you need to get your hands dirty. You own your business and you may need to do it all. You may eventually find help and build a team but when push comes to shove, you don’t say – that’s not my job. Do you envision yourself doing it all?

5. Do you have an exit plan?

On your entrepreneurial journey, you could lose sight and forget to evaluate when it’s time to cut your losses. Remember, a startup is both highly rewarding and risky. Have an exit plan before you jump in and each thanksgiving, re-evaluate if its time to change direction or call it quits.

There is absolutely no shame in changing direction or quitting if the data suggests so. Remember how Netflix used to be a DVD Rental service before they pioneered to online streaming? Sprig, a meal-kit business, called it quits after 5  years of business. Their business model wasn’t sustainable.

Moral of the story – listen to your data and be ready to make major changes if need be.

Did you answer yes to all five? Congratulations, you are now all set to jump onto the entrepreneurial boat. Meet you at sea! It’s going to be a one, fun, bumpy exciting ride. 

Shilpi Gupta is the founder of Edizeven - a job portal for restaurants.  She is a self proclaimed startup addict. After spending nearly a decade at Amazon, she ran a food business called Kukree before launching her current venture Edizeven.

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The Entrepreneur’s Reading List That Transforms Ideas Into Empires

These must-read titles and writing insights reveal how entrepreneurs turn bold ideas into empire-level success.

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top entrepreneurship books for business growth
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Entrepreneurship is powered by stories—of accomplishment, failure, and decision moments that define businesses. Books are maps, providing insight from individuals who’ve traversed the road ahead. (more…)

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Entrepreneurs

The Leadership Shift Every Company Needs in 2025

Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

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Bridging the gap between employees and employers
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In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”

While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.

Why This Gap Exists

Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.

What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.

Tools and Techniques to Bridge the Gap

Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.

1. Practice Mutual Empathy

Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.

2. Maintain Professional Boundaries

Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.

3. Follow the Golden Rule

Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.

4. Avoid Micromanagement

Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.

5. Empower Employees to Grow

Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.

6. Communicate in All Directions

Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.

7. Overcome Insecurities

Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.

8. Invest in Coaching and Mentorship

True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.

9. Eliminate Favoritism

Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.

10. Recognize Efforts Promptly

Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.

11. Conduct Thoughtful Exit Interviews

When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.

12. Provide Leadership Development

Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.

13. Adopt Soft Leadership Principles

Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.

The Bigger Picture: HR’s Role

Mercer’s global research highlights five key priorities for organizations:

  • Build diverse talent pipelines

  • Embrace flexible work models

  • Design compelling career paths

  • Simplify HR processes

  • Redefine the value HR brings

The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.

Treat Employees Like Associates, Not Just Staff

When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.

Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.

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Entrepreneurs

What Makes an Entrepreneurial Leader? Traits of the World’s Best Innovators

Inside the mindset of entrepreneurial leaders who transform risk, passion, and vision into world-changing results.

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entrepreneurial leadership skills and traits
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When you think of Richard Branson (Virgin Group), Bill Gates (Microsoft), Steve Jobs (Apple), Rupert Murdoch (News Corporation), and Ted Turner (CNN), one thing becomes clear: they are not just entrepreneurs, they are entrepreneurial leaders. (more…)

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Entrepreneurs

Building a Business Empire: Lessons from the World’s Boldest Entrepreneurs

Learn essential lessons, success strategies, and mindset shifts every aspiring entrepreneur needs to overcome challenges and build a thriving business.

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Back in July 2017, I attended a business seminar on entrepreneurship in India. With my appetite for learning and meeting new people, I wanted to explore the latest developments in the entrepreneurial world. (more…)

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