My 5 Pillars of Meaningful Happiness

After celebrating my 40th birthday in December with close friends in Los Angeles, I hopped on a plane to fly solo to Rio De Janeiro. On the flight, I reflected on my life and the amazing twists and turns that have come my way.

A few years ago, I established my four pillars of happiness—goals that I aspire to--after learning what people regret right before they pass away: working too much, not staying in touch with friends and family, and not letting yourself be happier.

My recent birthday provoked deep thoughts about whether I was living a meaningful life infused with happiness. While working hard comes with the territory as an entrepreneur, and I love what I do, I re-examined my goals for living a regret-free life.  

Here are my new and improved five pillars of meaning and happiness:

1. Gratitude
2. Friends and family
3. Do and experience more
4. Helping others
5. Health and mental wellness

1) Gratitude

I believe this principle is the most important because it enables an appreciation for the other pillars. Maintaining gratitude can be difficult, however, I’ve developed an appreciation for how unique and special life is.  

The more I consider the course of my life, the more I’m convinced that luck played the largest part because I never chose to be born me … I just was. While I’ve worked very hard to build my company, I feel lucky that I was born into a situation in which hard work can lead to such success.   

When I visit other countries, I’m reminded that many people are born into scenarios in which any amount of hard work or effort may not yield the same results. Gratitude is my state of mind.

2) Friends and family

I’ve always cherished friends and family and realized how important they are in my life, so I’ve increased my commitment to fostering these relationships.   

Fortunately, both my brothers and parents live locally in the Chicagoland area, so I see them frequently. I try to spend as much time as possible with my nieces and nephew to maintain “favorite uncle” status. I’m on the road a lot, and make it a priority to visit extended family as I travel.

Friendship is also extremely important: Last year I was a part of weddings in Pittsburgh, Chicago, New York, and Seville, Spain. My goal is to say yes to every invitation that comes my way.

3) Do and experience more

Around five years ago, I realized that I hadn’t left the US for the prior 7 years! I committed to traveling more, both domestically and internationally, and have since visited around 30 countries. I’ve learned about many cultures and grown tremendously as a result.   

The way I travel and what I gain from each trip has evolved. To minimize time away from work, I schedule 10-day trips, visiting three counties for an average of three nights each.  

I no longer worry about doing or seeing everything my destination has to offer; I focus on enjoying my time with an understanding that if I fall in love with a place, I can always return.   

I also prioritize meeting people and making friends while traveling. In our digital age, it’s easy to find photos, videos or even virtually walk down specific streets almost anywhere on the planet. However, meeting locals and embracing a culture requires an in-person experience.

4) Helping others

I’ve listened as motivational experts share how important helping others is to our own happiness and embraced the idea. It doesn’t necessarily require a lot of time, just a little effort.

I’m involved in a Chicago-based charity, StreetWise, which offers homeless individuals employment selling magazines and working toward self-sufficiency with dignity.

I find other small daily opportunities, from holding a door for someone to making an introduction to spark a relationship, I try to give to others whenever possible.  

5) Health and mental wellness

My understanding of how important this aspect of my life is grows with every birthday. Although I struggle to get to the gym and find mental peace, I’m optimistic that I will continue my pursuit of wellness.  

I’ve enjoyed phases of extreme motivation: Two years ago I practiced yoga twice a week and shifted to a completely vegetarian diet. I discovered that allocating time toward good health is the most valuable use of that time.

Today, I work out a couple of times a week and continue to eat healthfully. I’ve dabbled with meditation, but admittedly need a stronger commitment to developing this habit.

Most recently, I’ve begun minimizing the importance of material possessions in my life. I’ve reduced the amount of clothing I bring on trips, and my current wardrobe consists of jeans, a Perfect Search t-shirt, and a hoodie or blazer, depending on the environment. It’s rewarding to experience the freedom that shedding material possessions brings.

I’m stoked that I’ve made strides in establishing meaningful happiness in my life, but still have significant room to continue to learn and grow.