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2020’s Top 10 Love Lessons Working With The World’s Most Successful Single Entrepreneurs, Influencers and Celebrities

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While many people are happily waving Goodbye to 2020, and I’m reading countless social media updates about 2020 being the WORST year ever, I believe this past year has brought invaluable life and business lessons. At the height of the pandemic, most of the world was in fear, disbelief and operating in survival mode. In these times, how you handle news of this kind and your perspective towards unexpected challenges will impact how resilient you are. 

Once the dust settled, with forced isolation and social distancing mandated, I experienced more phone calls, more questions and more clients contacting our agency for help with their love life. The search and want for companionship during any significant life or world crisis quickly rise with the thought of having to endure utter global catastrophe alone, and worsen, as a single person. 

The pandemic has escalated problems and highlighted weaknesses in your life and business. As a matchmaker to some of the world’s most successful entrepreneurs, influencers, CEOs, and celebrities, I’ve had the privilege to learn what truly matters [to them] when finding love and their future life partner. 

Here are the top 10 Love Lessons working with some of the world’s most successful single entrepreneurs and celebrities—quotes taken from actual matchmaking clients.

1. A healthy partnership begins with self-care and self-love. 

Every time your flight attendant goes through their safety protocols before take-off, you’re reminded that you must always place the oxygen mask on yourself BEFORE you can help anyone else. Will Smith said, “You cannot make a person happy. I thought that was a real deep idea. You can make a person smile. You can make a person feel good. You can make a person laugh. But, whether or not a person is happy is deeply and totally and utterly out of your control.” The foundation of any healthy partnership begins with your own care, healing and mental wellness. A common concern for single entrepreneurs is they are introduced to someone who can meet them at their level. They have done the work to be ready mentally, emotionally, spiritually and physically to commit to a life partner.

2020’s Top 10 Love Lessons Learned From Successful Entrepreneurs | Will Smith

I have spent the last year or so really mapping out who and what I want. I am in one of the best shapes of my life… eat healthily and have a healthy workout regimen. I want to find someone that is both mentally and physically stimulating. Someone that enjoys deep conversations is open-minded about the world/life, and who can energize me. 

John 44 – Entrepreneur | Writer | Author | Speaker | Utah, USA

I’m spiritual and continue to practice spirituality in every area of my life. When you invest in yourself (mind, body, spirit), you start the journey to discover your most authentic self. And, in turn, your old beliefs evolve and change based on your journey of becoming. Becoming the best version of myself every day is my faith. 

Julie 34 | Head of Creative Development – Major entertainment brand 

2. Accountability is vital.

Most successful entrepreneurs subscribe to personal accountability or work with coaches to keep them accountable. Accountability is a willingness to accept responsibility for your actions 

2020’s Top 10 Love Lessons Learned From Successful Entrepreneurs | Sheryl Sandberg

The most important career choice you’ll make is who you marry.

Cheryl Sandberg | COO Facebook | California, USA

The pandemic has been an eye-opening year that has helped me realize valuable and important things to me. I tend to get so caught up in my work and career pursuits that I realized the importance of mindfully building the type of life I want to live. 

Melissa 34 | Ghost Writer | Copywriter | Toronto, Canada

3. Your word is your bond. 

I cannot recall how many times I’ve heard singles share how vital their partner be true to their word. The most common values entrepreneurs and high-level executives value in romantic partnership as similar to those they seek in professional relationships and partnerships. They value honesty, integrity, and trust, and all showcased in your ability to be your word.

2020’s Top 10 Love Lessons Learned From Successful Entrepreneurs | Oprah

If a man wants you, nothing can keep him away. If he doesn’t want you, nothing can make him stay. Stop making excuses for a man and his behaviour. Allow your intuition (or spirit) to save you from heartache.

Oprah Winfrey | Entrepreneur | Philanthropist | TV Personality

I am seeking a woman who is passionate, classic, healthy, open-minded, spiritual and aware. 

Darrell 53 | Executive Vice President | Major Bank | Toronto, Canada

I’m driven. Loyal. I’m focused on spending more time on appreciating life’s moments. Family, honesty and integrity are essential to me. 

Dean 64 CEO | Entrepreneur & Business Owner | Ottawa, Canada

4. An attitude of gratitude.

2020’s Top 10 Love Lessons from Successful Entrepreneurs | Joel Olstein

Kind people are my kind of people. 

Elicia 40 | Elite Wardrobe Stylist | Public Speaker | Media Guest | Edmonton, Canada

Travelling, learning, great conversation, my F45 class, karaoke and game nights, binge watching a great Netflix series, playing with my nieces, a book I can’t put down, oh and crossword puzzles. 

Michelle Female | Producer | 43 Toronto, Canada

Fierce + Grace, powered by compassion and humility. This is me.

Julie 34 | Head of Creative Development | Entertainment Industry | Beverly Hills, USA

5. Key Life Values outweigh possessions

2020’s Top 10 Love Lessons from Successful Entrepreneurs | Tony Robbins

Your values are the things you believe are essential in the way you live and work. They (should) determine your priorities and behaviours to reflect your values. The things that you do and the way you behave is a reflection of your values. And when these don’t line up with your value system, things feel out of alignment. It is a real source of unhappiness and anxiousness.

Looking for a kind life partner, a gentleman, ambitious, financially sound, loves to travel, affectionate, honest, respectful, good communicator, good sense of humour, adventurous/spontaneous at times. He takes care of his appearance, confident but not arrogant and makes time for a stable relationship as my top Love Language is quality time. Chemistry and looks are essential, but they don’t need to be a model lol (however I won’t complain if I get to date a model). Other qualities, along with some initial physical attraction, can make them even more attractive. 

Sophia 40 – Top Realtor | Toronto, Canada

I have a strong faith and value system and believe that you treat all individuals with respect and always understand perspectives that differ from yours. I am incredibly empathic, sometimes to a fault and will always give individuals the benefit of the doubt.

Olivia 44 | Neuropsychologist | Psychologist | Clinic Owner. Toronto, Canada

Organically connect, deep mutual respect, enlightening and honest conversation, shared interests, common values and goals, believe in love and romance……mature adults, share a healthy lifestyle that has both adventure, and cosy peacefulness.

Jennifer 41 Vice President | Financial Executive | Toronto, Canada

6. You are who you choose to surround yourself with.

In 2019, before the pandemic, I had the opportunity to attend the Genius Network, one of the largest professional conferences led by one of “the most connected men” on the planet, Joe Polish. At this conference, I was able to meet hundreds of the world’s leading entrepreneurs and mentors who shared what they believed to be the most important traits to find in a romantic partner and some of their secrets to living a happy life. 

2020’s Top 10 Love Lessons from Successful Entrepreneurs – Joe Polish

Every bit of money, every bit of progress in life comes through the connections that you actually make.

Joe Polish | Genius Network | Phoenix, Arizona

Dining and socializing with friends. I’m not into big parties and galas and nightclubs. I prefer more quality of time. I like to curl up and read or write in a notebook. I love being able to be physically active and break a sweat.

Amanda 35 | Writer & Marketer | Toronto, Canada

I am determined, disciplined, goal-oriented and focused. I’m an achiever who has a successful career and is now ready to focus on a romantic life with the right partner. I am well-travelled, classy, and prefer a close circle of friends. 

Lina 50 | Senior Vice President | Major Airline | North America

7. Family is everything.

Paul Carrick Brunson is a mentor, colleague and someone I consider to be a trusted friend. We met in 2008 at his first matchmaking conference and I’ve had the pleasure of traveling with him to a number of places including a mastermind in Barbados with his lovely wife and amazing business partner Jill, Brunson. Paul is a family man and prioritizes quality time he spends with sons and his wife. The life of an entrepreneur is not an easy one, and many sacrifices are made when you’re pursuing your dreams and making a difference in the world.

Top 10 Love Lessons Learned from Successful Entrepreneurs | Paul Brunson

I’m on the planet to be self-expressed, serve with joy, help alleviate suffering; to create a passionate partnership and joyous family — which has a lot to do with supporting my son’s creative gifts and building community; to be VITAL. ALIVE. PRESENT. PASSIONATE. 

Danielle 51 | Entrepreneur | Author | Speaker | Vancouver B.C

I am a kind, loyal person who is looking for my life partner. I am seeking a real connection with a woman who values family life and has high integrity. 

Eric 48 | Pharmacist | Entrepreneur | Pharmaceutical Industry | Humanitarian. Boston, USA

She is the centre of her social circle and has lots of friends. She has the personality of a small-town girl. She has a good, solid background, her parents are still married, and she is easy going with a good sense of humour. She is down to earth and open to self-improvement, is natural and healthy and enjoys spending time with family and friends. She is independent and ok with my travelling for business. 

Chad 45 Entrepreneur | Writer | Business Coach | Vancouver 

8. Time is both your enemy and your ally.

How do you feel about time? Do you see it as something on your side or as an obstacle to your success? Does it feel like you have plenty of time, there’s never enough of it or somewhere in between? I’ve interviewed many entrepreneurs who understand the finiteness of time and the importance of not wasting it when pursuing their passions and making the most of it. 

Top 10 Love Lessons Learned from Successful Entrepreneurs | Lewis Howes

“Get clear on what you want. Then find the people to support you to get it. Lewis Howes “

I believe that timing is truly everything. I was investing a lot in myself, growing spiritually and emotionally. I’m seeking the same in a life partner.

Julie 34 | Head of Creative Development | Major entertainment brand | Beverly Hills, California

I am blessed with a beautiful life, have been single and work focussed for long enough; it is time to share my life with someone special.

Olivia 44 | Neuropsychologist | Psychologist | Clinic Owner | Toronto, Canada

9. Reputation matters

2020’s Top 10 Love Lessons from Successful Entrepreneurs | Chris Rock

Many of my clients will Google someone and look at their social media accounts to gauge your reputation. I have found clients to decline a match or have concerns about your reputation when something reflects a lousy character, impaired judgment, or unwelcome news. 

They are socially connected, has a strength of character, intent to serve with compassion, light hearted fun & adventurous. 

Mark 38 | Executive Producer | Los Angeles, USA

I am seeking someone honest, thoughtful, ambitious, kind, generous, and reliable.

James 43 | Partner | Consultant | Ottawa, Canada

10. Sharing is caring. Life is better shared with someone special.

Every single entrepreneur I’ve had the chance to recruit for believes their life, success and failures are better when shared with someone special. As they say, a house is not a home until you make it one. Selfishness, narcissism, or self-centredness are not traits anyone has ever asked me to find in a life partner. So many of the entrepreneurs and millionaires I’ve interviewed did not achieve their goals for the sole purpose of financial freedom. Instead, they intend to help, share, support and empower others and their significant other.

2020s Top 10 Love Lessons Learned From Successful Entrepreneurs | Dr. Ramani
Relationships, like all human experiences, are transient; they change every day and are meant to be enjoyed in the present. When I hear people say you need to “work” at a relationship, what that often really means is just seeing through the day-to-day; listening to another person, listening to yourself, not getting stuck on hurts from the past, and not getting lost in what might come. To be in a relationship with someone you respect, care about and value is a gift, and when you take that in the day-to-day, you honor yourself and your partner each day. Eating is no different in that you can honor yourself at each meal. So much time in relationships is spent hashing the past, and arguing about things that haven’t yet happened. A relationship cannot be “hoarded”, just like a meal cannot be prolonged by taking home the leftovers.
― Ramani Durvasula, You Are WHY You Eat: Change Your Food Attitude, Change Your Life

I have always strived for quality and excellence in anything and anyone I involve myself with. I value kindness and feels it’s important to give back. 

Eric 49 | CEO | Entrepreneur | Boston, USA

Quality Time is my Love Language. Nothing says “I love you” like your full, undivided attention. I believe being there for my partner is critical, and being present. Turn the TV off, put your fork and knife down, and all chores and tasks on pause when you’re together spending quality time, however brief. Your partner makes you feel special and loved. Relationship distractions, postponed activities, and the failure to listen can be incredibly hurtful. Spending uninterrupted time talking, doing activities together, will deepen your connection through sharing valuable time.

Paul 44 | Firefighter | Business Owner | Niagara Falls, Canada

As we reflect on all of the life lessons 2020 brought, I look forward to brighter days and developing meaningful connections for myself and our clients. If you’re ready to allow love and resiliency be your theme for 2021, contact us to learn more about how we can support your journey to better love. 

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