As an entrepreneur, you've likely had a conversation with yourself or with a partner that sounds something like this: "Why am I doing this? The ambiguity is killing me." We all wrestle with some version of these questions. While there are plenty of possible triggers for these thoughts of doubt, their impact affects something precious--our happiness.

The version of happy that I'm writing about is not one that you might experience after winning the lottery. It's not the happiness you feel when eating your favorite food. The question, "Are you doing what makes you happy?" is asking something more profound. Another way to interpret the question is to ask yourself, "Does my work fulfill me?"

Researchers have categorized happiness in two ways: hedonic and eudaimonic happiness. Hedonic happiness is fleeting and often triggered by some external event or experience. Eudaimonic happiness is about human flourishing. Linked to eudaimonia are beliefs that you have meaning in your life, vitality, wisdom, and intrinsic motivation. It's the latter version of happiness that matters most.

Are you doing work that brings meaning to your life? Makes you feel alive? The answer to these questions is the one I want you to know. To help you dig in and answer these questions, I've put together insights and tips from experts and CEOs. Their collective wisdom will likely hold a nugget of truth or reveal a pearl of wisdom that will make a difference for you.

Expert Advice for More Happiness in Life

To encourage you to examine what can bring you more happiness, the following insights are from various experts, including me, on how to get more of the good stuff in your life.

The Happiness Matrix from Mike Steib, CEO

Mike Steib is the CEO of the XO Group Inc. Steib's company is the mastermind behind favorite websites like The Knot, The Bump, and The Nest. His epiphany about how the residual effects of his work unhappiness colored his personal life led him to create the Happiness Matrix.

Taken from Steib's book, The Career Manifesto, the Happiness Matrix exercise has you identify critical areas of impact in your life--family, work, community, for example. You then answer three prompts for each of the impact areas:

  • "Things I truly enjoy or would truly enjoy."
  • "Things I hate."
  • "Things it would be difficult to be happy without."

By answering the above prompts, you position yourself to make decisions about bringing more meaning into your life. Steib's book is full of great exercises no matter your role at work: founder, owner, employee, intern, temp.

Meaningful Relationships from author, professor David Burkus

As an entrepreneur, it is easy to put off building relationships within your industry and outside it, too. We are wired to seek out relationships. To deny ourselves time to connect with others will undermine our health and life satisfaction. Consider picking up David Burkus's new book Friend of a Friend for cutting-edge insights on using the network.

Define Your Personal Values from the non-profit InnerWill

Happiness is linked to living a life that aligns with what you believe. I find that most leaders have an intuitive sense of their values. Likely, though, they are top-of-mind: integrity, family, health, for example. There is nothing wrong with these values. I find, however, that when leaders spend time reflecting on their experiences, more personal values surface.

One of my favorite companies, Luck Companies, has a non-profit named InnerWill. Their focus is to help spread values-based leadership to companies. Check out their online tool Igniter. It's free and will guide you through a series of exercises to identify values that will lead to more meaningful insights.

What's Your Purpose-Orientation from Aaron Hurst's company, Imperative         

Another great way to know what calls you is to take Imperative's Purpose Assessment.  It's worth knowing which purpose-centered habits are central to your purpose.

Evaluate Your Work Practices from yours truly

The last tip is perhaps the hardest one. When you are the Chief Everything Officer, it is hard to stop working. Continuously working 100+ hours a week is not sustainable. I know Gary V and Daymond John advocate for the "rise and grind" mindset. While putting in the time to grow your business is a non-negotiable for success, it does not mean that you compromise your physical and mental health. Sleep is key to success. So, be sure you are blocking time in your calendar to decompress from work. Do something for yourself, with your kids, with your significant other. Stop sending emails after 6 pm. Do your one-on-ones as Walk and Talks.

You need to be slow to be fast.

A more profound sense of happiness comes from being your best. It comes from knowing that you're doing what you are meant to be doing. You'll experience these insights through reflection and exploration, both of which are unending inquiries that span the breadth of your life.