I’ve Worked With Dozens of Highly Successful — But Unfulfilled — Entrepreneurs. Here’s How I Helped Them Find Their Purpose.


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If I asked you, “What is your legacy?” What would you say? Is it your family, your wealth, a foundation you launched, or, if you’re an entrepreneur or business owner, the company you created that defines who you are and how you will be remembered?

For many in the business world, this is a question they don’t start asking themselves until later in life. Early in our professional lives, we tend to focus on short-term outcomes, hard work and doing whatever it takes to make our business profitable. Often, this stage of life requires managing the daily challenges of running a business while also starting or raising a family.

In my experience, few of us ever take the time to look forward at where we want to be in the long-term future and what our legacy will be. But I believe it’s just as important to examine those questions early in life – not just when we’re older, and after our children have grown up and left home.

Ultimately, it’s a question of finding fulfillment. But too often, we focus on fulfillment as an end goal: selling your business after decades of hard work, ensuring a comfortable retirement and having the means to support your family after you’re gone. Most of our long-term goals are anchored in financial success. While those are certainly important objectives, I’ve worked with dozens of successful entrepreneurs who have achieved tremendous levels of business and financial success but remain fundamentally unfulfilled.

Many of those same entrepreneurs I have worked with go through life checking boxes, from starting and selling a business to buying a second (or third or fourth) house, acquiring the real-life sports car they had once had on their bedroom wall as a poster growing up, or traveling to East Africa to see the “Big-Five.” Many of these actions or acquisitions are under the guise of seeking happiness, certainty or significance.

Related: Unlock the Key to a More Fulfilled Life in 3 Simple Steps

Best-selling author and Harvard professor Arthur Brooks calls this “the bucket list trap.” We all know about the bucket list; many of you may have one. This is the list of all the things you want to see, do and acquire before you die.

As Brooks writes in From Strength to Strength: Finding Success, Happiness and Deep Purpose in the Second Half of Life, there is a risk your sense of purpose and meaning can fall by the wayside as you chase the items on your list for the sake of saying you did it, not for the fulfillment they’ll bring you or the impact they’ll create in the world.

To be clear, there’s nothing wrong with the pleasure of chasing a bucket list. If you dream of hiking to Machu Picchu or buying your dream car, go for it! Just don’t do it for the sake of ticking boxes, as, in my experience, it rarely leads to fulfillment.

Finding fulfillment can seem like an intangible goal — is it providing for your family, creating wealth, being a philanthropist or protecting the environment? It is such a broad and nebulous subject that when I work with clients, I try to break it down into two parts: inner purpose and outer purpose.

In their simplest forms, inner purpose refers to living as the best version of yourself, and outer purpose is about living for something greater than yourself.

Inner purpose: Authentic self-alignment

Inner purpose is about living as the best and most authentic version of you. It involves aligning your mental, physical, spiritual and emotional well-being. When these four areas of your life are balanced, you create a foundation for self-awareness and self-connection, which are essential components of fulfillment. For business owners and entrepreneurs, the focus should be on:

  1. Mental well-being: Cultivate a mindset of growth and resilience. Engage in continuous learning and personal development. Try to manage the constant stresses of running a business and managing your life through mindfulness practices and a focus on maintaining a positive outlook.
  2. Physical well-being: We can never really focus enough on our physical health. It truly is the most important thing that underpins our ability to meet our purpose and find fulfillment. Regular exercise, a healthy diet and adequate rest are all crucial but often the first things we sacrifice in busy times. A healthy body supports a healthy mind, enabling you to perform at your best in all areas of life.
  3. Spiritual well-being: Connect with your core values and beliefs. This could involve meditation, reflection or engagement with a community that shares your values. It doesn’t have to involve yoga retreats or vision quests — it can be as simple as being part of a golf club or going to church. Spiritual well-being provides a sense of purpose and direction, often anchored by a connection to a community.
  4. Emotional well-being: Foster emotional intelligence by understanding and managing your emotions. Build strong relationships with friends, family and even peers in the business world and seek their advice and support when needed. Emotional health is key to maintaining balance and making informed, thoughtful decisions.

Related: 10 Ways to Be an Authentic Entrepreneur and Sell Your Best Self

Outer purpose: Connecting and contributing

Outer purpose is about living for something greater than yourself. It involves fostering connections and making meaningful contributions to your family, friends, community and the world. For business owners and entrepreneurs, this should be anchored in:

  1. Family: Ensure that your business supports and enhances your family life — not the other way around. Building a successful business or organization often requires us to sacrifice time with our family. In small amounts, that can work, but over the long term, there has to be a balance between your professional and personal responsibilities. It’s a balance I struggled to achieve for years, but it’s essential for personal fulfillment and business success.
  2. Friends: Build a network of supportive friends and colleagues. Share your journey with them and offer support in return. Strong relationships provide a unique level of fulfillment and build networks that can support and grow your business. Beyond my immediate family, it’s my friends who continue to inspire and motivate me.
  3. Community: Be an active member of your local community – whether that’s connecting to your home state, city or your own neighborhood. Participate in local events sporting and charitable events, support community projects, and give back through volunteer work or sponsorships. Be visible in your community, which will help both your personal and business bottom lines.
  4. World: Consider your business’s broader impact on the world. Is it contributing to a better planet and a better future, or is it extracting more than it contributes? Implement sustainable practices, support social causes, and aim to create products or services that contribute positively to society. A business with a strong outer purpose can attract loyal customers and partners who share your values.

The cycle of positive reinforcement

When you live authentically and take care of your well-being, you are better equipped to connect and contribute to the world around you. These external connections and contributions, in turn, reinforce your internal sense of purpose and well-being.

I strongly believe that if you incorporate the concepts of inner purpose and outer purpose into your personal and business lives, you will create a positive cycle of reinforcement that creates a legacy anchored in personal fulfillment while making a meaningful impact on the world. What could be a better legacy than that?



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