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Why Dating An Entrepreneur Is Very Different To The Norm

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We entrepreneurs are a very different breed. Some might say we are almost like aliens with the way we think and the way we act. Maybe we are, who knows. Entrepreneurs like me are not so much driven by material possessions or the “what” and “how” behind every idea.

Entrepreneurs are obsessed with the “why” and turning it into a vision that gives themselves and everyone around them goosebumps. There’s no sense of ego behind this way of thinking; it’s more about creating positive change when it’s so easy to get lost in this negative world.

Dating an entrepreneur can be a bumpy ride if you haven’t read the map beforehand. My job is to help you understand us crazy entrepreneurs so that you can date one if you so choose. It’s a wild ride, but it’s one you will never forget. It’s a journey of giving, contribution, gratitude, and respect.

Entrepreneurs can teach you so much about life and help you discover things inside yourself that you were never aware of. They can help you find your why and get you following your same passion with a bizarre sense of momentum and energy. It’s time to fall in love.

Below are 12 reasons why dating an entrepreneur is very different:

1. Everyone’s talking about what they had for lunch – we’re thinking about changing the world

In a normal society, it’s common to talk about the simple things in life, like what we had for lunch, and describing it in tremendous detail like it’s a shiny crystal that you’ve never seen before. If an entrepreneur is present in a conversation like this, you might find them looking distracted or not paying attention to the conversation.

Entrepreneurs are distracted because while everyone is thinking about everyday things, we entrepreneurs are thinking about changing the world. Instead of having a chip on our shoulder about the traffic coming to work in the morning, our mind is off thinking about how we can contribute something unforgettable to humankind.

While everyone’s chasing Friday afternoon at the local pub, we’re thinking about what we can do over the weekend to ultimately inspire us further towards our purpose. We want to take a journey into nature to find something within ourselves that may unlock the next big idea or the next problem to be solved.

“Entrepreneurship is an obsession, but it comes from a beautiful place”

2. We’re looking for purpose not looks

It may seem strange, but we entrepreneurs are not solely focused on looks like the rest of our Instagram culture. We’re focused on a sense of purpose in our prospective partner. We’re looking for a gorgeous somebody who not only lights us up with their smile but makes us connect to a purpose that is bigger than ourselves.

Purpose is better than any chest or abs, and it makes us go wild. It makes our inner world crumble and helps us let our guard down. It makes us feel like we are not the only wild person living on this planet. A sense of purpose aligns to our entrepreneurial nature.

Looks come and looks go with age, but a sense of purpose is everlasting. A sense of purpose overpowers any other physical form that could tempt us away from our true entrepreneurial mindset.

3. We’re 100% focused on mindset

It can feel like a math test when you date an entrepreneur. This is because every question we ask a prospective partner is designed to help us uncover the other person’s mindset. We want them to believe, as we do, that anything is possible.

We’re secretly hoping that they don’t waste their precious energy on fretting the small stuff, such as how the supermarket sold out of their favorite bread this morning and it ruined their day.

For entrepreneurs, mindset is such a sticking point because our one true love can deeply affect our own mindset. We guard our mindset like buried treasure, and we’re not willing to allow it to be overcome by negativity at any cost.

We’re stubborn in some ways but it’s all for a good cause: our purpose.

4. We won’t settle for second best

While it’s the norm to settle for comfortable and mediocre, you’ll very rarely meet an entrepreneur that will be happy to settle for this way of living. Entrepreneurs want the best and they demand high standards. We believe we can influence any outcome, and convince anyone to give us what we want.

We believe that we’ve spent years of our life grinding and hustling away at our craft, and we’re not about to give up all that hard work to take second place. It’s not so much about perfection, but more about maintaining high standards that give us the rewards we need to stay motivated.

It’s a philosophy of always pushing the boundaries, and not accepting what we’re told just because everyone else accepted the same answer. It’s our rebel nature coming alive for the greater good. Deep down we’re lions ready to pounce on our prey.

5. We want to do the impossible

It’s rare that you will find an entrepreneur who is not talking big things. That’s because we want to achieve the impossible. We don’t want to “sort of” fix the world with software, we want to transform it and make everyone’s life better.

We want to help those who are less fortunate realize their own entrepreneurial dream so that they can do what we have done, and what we’re about to do. It’s a sense of belonging to the same human cause, and knowing that nothing in life worth achieving is going to be easy.

Small goals with minimal impact don’t get us entrepreneurs excited. We want more and we demand more. Not because we’re schmucks – we want more because it’s possible. The moment we meet someone who lets all the small problems overcome them is generally the moment that we run in the opposite direction.

They don’t need to be at the same level us as when it comes to believing in the impossible, but they do need to share this way of thinking to some degree.

6. Everything has to be simpler than it is

There is a lot of money to be made in consulting and in business by making problems seem way more complex than they are. If a problem were easy to solve, then everyone would do it and I couldn’t charge you hundreds of thousands of dollars to solve it for you.

Nobody would solve the issue because it would be perceived to be impossible, thus blocking out any potential competition and allowing me to charge an exorbitant amount of money for the solution. Dating an entrepreneur will teach you that we believe things are simple.

We believe that while everyone is describing a problem as hard, it’s actually straight forward when you chunk it down and remove all the associated myths. We want things to be simple because we know that the only way to get mass adoption in any business is through simplicity.

If consumers can’t understand your solution in a 60-second Facebook video, then you’ve probably lost them for life.

7. We’d rather be inspired than stuff our face

As soon as the weekend rolls around, it’s tempting for non-entrepreneurs to want to stuff their faces and drown out their depressing week of nothingness and lack of purpose. The difference with entrepreneurs is that we would rather seek inspiration than a food coma.

We want to find meaning in everything that we do, and we don’t like to waste our time on something that doesn’t give us momentum towards our vision.

“We’re not trying to block out the world, we are trying to understand it. We’re not trying to numb the pain; we’re trying to use it to motivate us forward and understand the cause”

We’re like life scientists always looking for what’s holding us back, and always trying to take the game up a notch.

8. We are prepared to work harder than everyone else

While our friends are often enjoying themselves after work, we’re locked in our office prepared to work harder than anybody else. We’re up early (some of us at 4am), and we’re ready to get a head start on our dream.

Our lives are somewhat dominated by our calendar because we know that we have to put in the hours and do the work to achieve the impossible. We know that we want unreasonable results, so we have to put in an unreasonable amount of time towards our life’s work.

When pain sets in from exhaustion, we find something deep down that helps us go beyond our pain threshold. Even when we don’t feel inspired, we find a way to draw inspiration from an external source. It’s a relentless, unstoppable hunger, to just get on with the job and keep moving forward at all costs, that fuels our day.

9. We don’t care what anyone thinks

Most of the time our vision seems totally off the charts. To the average person, we seem like mad scientists trying to invent teleportation. Our ideas only seem mad until we have a breakthrough and we start generating revenue. Then we look less mad but still a bit nuts.

As our revenue grows further and we raise some VC money, all of a sudden perception shifts. This whole process happens and we know that it’s how business works. While everyone’s hating we just ignore them because we know they don’t think like us. We know that some people create the vision and other people follow our vision.

10. Reading equals TV to us

Decompressing after you get home for an entrepreneur is all about reading. Instead of TV that serves no real purpose, reading allows us to unwind and still learn at the same time. We entrepreneurs know that we need to model the greats, and understand the strategies that others have used to win.

So yes, we read a lot, and that’s our way of relaxing while still getting meaningful work done. We struggle as an entrepreneurial species to waste a single moment on something that doesn’t serve our vision, with the exception of time with our family and loved ones.

11. We ask quality questions a lot

Dating an entrepreneur is like dating Larry King; we’re always asking questions. We’ll often ask the same question multiple times in different ways. This is because we believe that questions are our secret weapon. The way you ask a question can determine the answers you will have at hand.

Questions are how we model people who have done things similar to what we want to achieve. The art of the question helps us see beyond the answers that everyone else chooses to accept.

12. We care about people more than you will ever understand

You’ll notice that we entrepreneurs care about people almost more than anything else. This is no coincidence. The reason we care about people is because we understand that to have a massive vision with wild, audacious goals, we need people to help us win.

We know that we can’t do anything by ourselves, and we have to bring people along the journey with us. This relationship with people is somewhat of a passion that we have, and it never stops. We learn to love and respect people.

We know that to get what we want (achieve our vision), we have to help the people that follow us get what they want. As entrepreneurs, we are primarily nothing more than leaders that attract people to our ideas, and are prepared to think that the world can be so much more.

We want to use our love for the planet that we all share to do the impossible. We want to unite nations rather than tear them down. We want to do what nature tells us and grow as a movement.

What do you think about dating an entrepreneur? Let me know on my website timdenning.net or my Facebook.
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The Entrepreneur’s Reading List That Transforms Ideas Into Empires

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

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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

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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:

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  • 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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